CN116964031A - Antiparasitic compounds - Google Patents
Antiparasitic compounds Download PDFInfo
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- CN116964031A CN116964031A CN202280016464.4A CN202280016464A CN116964031A CN 116964031 A CN116964031 A CN 116964031A CN 202280016464 A CN202280016464 A CN 202280016464A CN 116964031 A CN116964031 A CN 116964031A
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- alkyl
- haloalkyl
- group
- cycloalkyl
- alkoxy
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 129
- 230000002141 anti-parasite Effects 0.000 title description 5
- 239000003096 antiparasitic agent Substances 0.000 title description 5
- 241001465754 Metazoa Species 0.000 claims abstract description 49
- 206010061217 Infestation Diseases 0.000 claims abstract description 26
- 238000011282 treatment Methods 0.000 claims abstract description 7
- 230000003071 parasitic effect Effects 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 1330
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 915
- 229910052731 fluorine Inorganic materials 0.000 claims description 603
- 229910052739 hydrogen Inorganic materials 0.000 claims description 540
- 125000001188 haloalkyl group Chemical group 0.000 claims description 478
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 393
- 229910052740 iodine Inorganic materials 0.000 claims description 378
- 125000003342 alkenyl group Chemical group 0.000 claims description 306
- 125000000304 alkynyl group Chemical group 0.000 claims description 302
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 290
- 125000003545 alkoxy group Chemical group 0.000 claims description 282
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 251
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 242
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 167
- 125000004429 atom Chemical group 0.000 claims description 149
- 125000001424 substituent group Chemical group 0.000 claims description 139
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 108
- 229910052801 chlorine Inorganic materials 0.000 claims description 101
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 101
- 125000001425 triazolyl group Chemical group 0.000 claims description 96
- 150000003839 salts Chemical class 0.000 claims description 94
- 125000004076 pyridyl group Chemical group 0.000 claims description 85
- 125000000335 thiazolyl group Chemical group 0.000 claims description 85
- 125000002883 imidazolyl group Chemical group 0.000 claims description 84
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 84
- 125000001544 thienyl group Chemical group 0.000 claims description 84
- 229910052757 nitrogen Inorganic materials 0.000 claims description 78
- 238000000034 method Methods 0.000 claims description 57
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 51
- -1 halocycloalkenyl Chemical group 0.000 claims description 48
- 150000001204 N-oxides Chemical class 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 47
- 239000013078 crystal Substances 0.000 claims description 47
- 150000002148 esters Chemical class 0.000 claims description 47
- 239000012453 solvate Substances 0.000 claims description 47
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 45
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 45
- 125000002971 oxazolyl group Chemical group 0.000 claims description 45
- 125000005843 halogen group Chemical group 0.000 claims description 42
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 40
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 40
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 40
- 244000045947 parasite Species 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 244000078703 ectoparasite Species 0.000 claims description 12
- 241000238876 Acari Species 0.000 claims description 8
- 241001481703 Rhipicephalus <genus> Species 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 241000283690 Bos taurus Species 0.000 claims description 6
- 230000003442 weekly effect Effects 0.000 claims description 4
- 241000251468 Actinopterygii Species 0.000 claims description 3
- 201000001064 tick infestation Diseases 0.000 claims description 3
- 241000282465 Canis Species 0.000 claims description 2
- 241000282324 Felis Species 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims description 2
- 241000282849 Ruminantia Species 0.000 claims description 2
- 230000000895 acaricidal effect Effects 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 239000007972 injectable composition Substances 0.000 claims description 2
- 208000028454 lice infestation Diseases 0.000 claims description 2
- 230000000699 topical effect Effects 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 claims 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims 3
- 229930195729 fatty acid Natural products 0.000 claims 3
- 239000000194 fatty acid Substances 0.000 claims 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 2
- FZTHHIGKHFQAKY-UHFFFAOYSA-N 1-octanoyloxypropan-2-yl decanoate Chemical compound CCCCCCCCCC(=O)OC(C)COC(=O)CCCCCCC FZTHHIGKHFQAKY-UHFFFAOYSA-N 0.000 claims 1
- YHKPUGAKEKXNDC-UHFFFAOYSA-N 2-octanoyloxypropyl decanoate Chemical compound CCCCCCCCCC(=O)OCC(C)OC(=O)CCCCCCC YHKPUGAKEKXNDC-UHFFFAOYSA-N 0.000 claims 1
- PWEOPMBMTXREGV-UHFFFAOYSA-N decanoic acid;octanoic acid;propane-1,2-diol Chemical compound CC(O)CO.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCCCC(O)=O.CCCCCCCCCC(O)=O PWEOPMBMTXREGV-UHFFFAOYSA-N 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- 150000004665 fatty acids Chemical class 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000003961 penetration enhancing agent Substances 0.000 claims 1
- 150000005691 triesters Chemical class 0.000 claims 1
- AVNRGMVELRMJLJ-UHFFFAOYSA-N 2-cyclopropylprop-2-enamide Chemical class NC(=O)C(=C)C1CC1 AVNRGMVELRMJLJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 17
- 239000003814 drug Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 7
- 125000003386 piperidinyl group Chemical group 0.000 description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 6
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 6
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 6
- 241000238680 Rhipicephalus microplus Species 0.000 description 5
- 244000000054 animal parasite Species 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 4
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical class NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 3
- 229920006235 chlorinated polyethylene elastomer Polymers 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000000590 parasiticidal effect Effects 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 235000019688 fish Nutrition 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 108700012359 toxins Proteins 0.000 description 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 206010004194 Bed bug infestation Diseases 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000006004 Flea Infestations Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241001390651 Micropus Species 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 229910018503 SF6 Inorganic materials 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000000136 cloud-point extraction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- 230000009340 pathogen transmission Effects 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 244000000040 protozoan parasite Species 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- SFZCNBIFKDRMGX-UHFFFAOYSA-N sulfur hexafluoride Chemical compound FS(F)(F)(F)(F)F SFZCNBIFKDRMGX-UHFFFAOYSA-N 0.000 description 1
- 229960000909 sulfur hexafluoride Drugs 0.000 description 1
- 125000005458 thianyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Abstract
The present invention relates to cyclopropylacrylamide compounds useful in the treatment of parasitic infestations in animals. The compound has the formula (I).
Description
Technical Field
The present invention relates to the use of cyclopropylamide compounds, compositions and methods for controlling parasite infestations of animals.
Background
Many parasites are known to develop on animals. These parasites pose a significant hazard to animals and their owners.
It is therefore important to treat animals to prevent infestation by parasites, or to reduce or control the reproduction of these parasites, in particular ectoparasites of animals, such as ticks in animals.
Compounds currently available for controlling parasites, especially ectoparasites and ticks, do not always show good results, fast enough onset of action or long duration of action.
Ectoparasites tend to irritate animals and can also cause clinical diseases and adverse sub-clinical conditions by themselves or by pathogens transmitted through the carrier.
In particular, ticks are parasitic on wild animals, domestic animals and humans, and are known or suspected to be the cause of transmission of pathogens, including bacteria, viruses and protozoan parasites. Ticks also release toxins, which cause inflammation or paralysis in the host. Occasionally, these toxins are lethal to the host.
On the other hand, such ectoparasites severely affect the productivity of animal husbandry by reducing weight gain or milk production, leading to poor quality of hides, wool and meat, and in some cases death. Ectoparasites are also part of the cause of pathogen transmission as a vehicle and cause animal and companion animal discomfort, affecting animal welfare.
For example, parasites commonly found in domestic animals such as cattle are ticks of the genus rhipicephalus, especially rhipicephalus (r. Microplus) (tropical cattle ticks), depigmenting rhipicephalus (r. Decolouratus) and rhipicephalus circulans (r. Annulus). Ticks such as rhipicephalus (original rhipicephalus) are difficult to control because they lay eggs in pastures where animals eat grass.
Such limitations include toxicity and safety of the existing compounds to animals and users/owners, limited efficacy (potency, onset and duration of activity), narrow range of parasiticidal action, bioavailability, pharmacokinetic and pharmacodynamic challenges, and resistance issues. In addition, certain aspects of the present invention overcome at least some limitations in the use of existing parasiticides, particularly in providing effective long-term, safe control of parasites that are known to be difficult to treat.
International patent applications WO 2016/168856, WO 2016/168858, WO 2016/168859 and WO2018/071327 disclose that certain cyclopropylamide compounds have insecticidal and acaricidal activity and are therefore useful for controlling agricultural plant pests. Although veterinary uses are briefly mentioned, none of these references exemplifies or describes the use of the claimed compounds of the present application, which at least meets some of the needs for using such compounds as veterinary medicaments as described above. Furthermore, only a small fraction of the compounds described in these cited documents were found to actually act on veterinary parasites.
Disclosure of Invention
The present application relates in a first aspect to compounds of formula (I)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein A is 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 Wherein no more than 3 of the N groups are N or n=o;
R 1 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl group、S(C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl Phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl group,NH(C 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 11 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) Alkyl group
H、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) A haloalkyl group;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
Suitably, the compounds of the application and any embodiments thereof are used in a method of treating or controlling parasite infestations of an animal,
suitably, the compounds and uses according to the application and/or any embodiment thereof
R 1 Selected from H, F and Cl;
R 2 selected from H, F and Cl;
R 3 selected from H, F and Cl;
R 4 selected from H, F and Cl;
R 5 selected from H, F, cl, br and I;
R 6 selected from H, F and Cl, br and CH 3 ；
R 7 Selected from H, F, cl, br and I;
R 8 selected from H, F, cl, and Br and CH 3 ；
R 9 Selected from H, F, cl, br and I;
R 11 is H;
R 12 selected from H, F, CL, CH 3 、CF 3 ；
R 13 Selected from H, F, cl, CF 3 And CH (CH) 3 ；
R 14 Is H or F;
R 15 selected from H and CH 3 。
Suitably, the compounds and uses according to the application and/or any embodiment thereof
R 1 Is H;
R 2 selected from H, F and Cl;
R 3 selected from H, cl, F and Br;
R 4 is H, F, cl;
R 5 selected from H, F and Cl;
R 6 selected from H, F and Cl and CH 3 ；
R 7 Selected from H, F and Cl;
R 8 selected from H, F, cl and CH 3 ；
R 9 Selected from H, F and Cl;
R 11 is H;
R 12 selected from H, F and Cl;
R 13 selected from H, F and Cl;
R 14 is H;
R 15 selected from H and CH 3 。
Surprisingly, it has been found that the compounds described in the present application are useful as medicaments, in particular as veterinary antiparasitic medicaments for the treatment or control of parasite infestations of animals.
The present application is to be understood as embracing the compounds of the application described in the present application and/or embodiments thereof for use as a medicament, in particular a veterinary medicament, more preferably an antiparasitic veterinary medicament.
The present application is also to be understood as including the use of the compounds of the application described in the present application and/or embodiments thereof in the manufacture of a medicament for the treatment or control of parasite infestations in an animal.
The present application is also to be understood as including the use of the compounds of the application described in the present application and/or embodiments thereof in the manufacture of a medicament for protecting animals from parasite infestations.
The compounds of the present application and/or embodiments thereof are suitable for use in methods of treating or controlling ectoparasite infestations.
Suitably, the compounds of the present application and/or embodiments thereof are used in methods wherein the parasite infestation is a tick infestation or a flea infestation. The compounds are suitable for use in tick infestations.
The compounds of the application and/or embodiments thereof are suitably used against parasites, wherein the parasite is a single host tick or a multi-host tick. Suitably, the compounds of the application are useful against rhipicephalus minutissima.
In a suitable use or method of the application and/or any embodiment thereof, the animal is a warm-blooded animal, such as a mammal. Suitably, the compound is also active in livestock (e.g. ruminants, bovine or bovine). The compounds were also found to have activity against sea lice infestations in fish. The compounds have also been found to be active in companion animals (e.g., canine or feline, particularly dogs or cats).
In a suitable use or method of the invention and/or any embodiment thereof, the animal is protected from parasite infestations. Preferably, the existing parasite infestations of the animal are treated or controlled.
In a suitable use or method of the invention and/or any embodiment thereof, the method comprises administering the compound to the animal weekly, biweekly, monthly, 6 weekly, 2 monthly, or 3 monthly.
The present invention also relates to a veterinary composition comprising an effective amount of a compound of formula (I) - (XCII) as defined in any of the embodiments described herein and an inert carrier or formulation adjuvant. The compositions are useful for treating and controlling parasite infestations in animals, as described herein.
Suitably, the veterinary composition is a topical composition, an oral composition or an injectable composition.
Drawings
Fig. 1 shows plasma concentrations of an oily solution (composition a) and a volatile solution (composition B) of compound 453.
Figure 2 shows a comparison of the concentration of compound 453 in bovine blood without CPE (composition C) and with three different CPEs (compositions D, E and F), showing no significant improvement in inclusion of any CPE.
Figure 3 shows the onset of >90% efficacy against rhipicephalus microplus for a duration of >90% efficacy against rhipicephalus microplus and >90% efficacy against rhipicephalus microplus micropus for composition G, H and the composition of example 1.
Fig. 4: structure of compounds 1-480.
Detailed Description
The detailed description of the preferred embodiments is merely intended to familiarize others skilled in the art with applicant's invention, its principles, and its practical applications so that others skilled in the art may modify and apply the invention in various forms as they may be best suited to the requirements of a particular use. The detailed description and specific examples, while indicating the preferred embodiments of the invention, are given for illustration purposes only.
Therefore, the present invention is not limited to the preferred embodiments described in the present specification, and various modifications are possible. In addition, for purposes of brevity and readability, only a few combinations of embodiments are explicitly described, but it should be understood that other combinations of embodiments are also contemplated.
Briefly, the present invention relates to compounds that are generally useful as active ingredients in medicaments for animals. The compounds of the present invention and/or embodiments thereof are suitable for use in methods of treating or controlling ectoparasite infestations and/or protecting animals from parasite infestations.
Surprisingly, it has been found that the compounds of the invention and/or embodiments thereof described herein exhibit an excellent broad spectrum efficacy against harmful parasites more rapidly and over a long duration of time when administered to animals in need thereof, compared to other similar compounds known in the art. Thus, these compounds may be used in the methods or uses of the present invention and/or embodiments thereof.
Hereinafter, when disclosed as a compound per se or as a compound used in the method according to the present invention, a compound used according to the present invention and/or its embodiments is described as "a compound of the present invention" or "a compound of the present invention and/or its embodiments (including a compound of formula (I)") or "a compound of formula (I)".
The unexpectedly broad parasiticidal properties of these compounds used in accordance with the present invention and/or embodiments thereof are of considerable importance, as there are few agrochemicals that can be effectively used against ectoparasites of animals, let alone against a broad range of animal parasites and in a variety of target species.
In addition, it has been found that a single administration of such compounds, using the relevant routes of administration, generally provides effective activity against a wide range of ectoparasites, including parasite infestations that are difficult to treat, while also tending to provide a rapid onset of activity and/or a long duration of activity, and/or a desirable safety profile, therefore, these compounds have proven useful as medicaments, especially anti-parasitic veterinary medicaments.
The compounds of the application and/or embodiments thereof show desirable beneficial properties, which make their use in animal medicine suitable, and further show very advantageous resistance blocking properties of such compounds.
The examples demonstrate that the compounds of the present application and/or embodiments thereof, including compounds of formula (I), have a wide range of activity in vitro and in vivo against a wide variety of veterinary-related parasites affecting animals, such as single and multi-host ticks, fleas, bed bugs and sea lice, which belong to a wide variety of biological organisms of veterinary-related parasites. It is further shown in the examples that existing parasite infestations of this type of parasite in different animals (cattle, dogs, fish, guinea pigs) can be successfully treated while being safe for the animals.
Furthermore, the examples demonstrate that the compounds of the present application and/or embodiments thereof act on a variety of animal parasites, particularly ectoparasites, when administered to a variety of target animals using a variety of routes of administration.
Thus, by using the compounds of the application and/or embodiments thereof described herein, the disadvantages of the prior art may be avoided, as convenient, safe administration of the cyclopropylamide compounds will be sufficient to achieve the desired effect.
In a first aspect, the present invention relates to a compound of formula (I)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
and wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N or n=o;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
Found therein from C-A 1 -A 2 -A 3 -A 4 -A 5 Compounds in which the ring formed is substituted by at least one halogen, which compounds are active against animal ectoparasites. This is the same as in the case of C-A 1 -A 2 -A 3 -A 4 -A 5 Compounds in which the ring formed is not substituted by halogen are in contrast.
The following comparative examples show that similar compounds have been tested against a range of agrochemically related parasites in prior art documents WO 2016/168859 and WO 2018/071327. Many of the compounds of WO 2016/168859 and WO2018/071327 that were active in plant protection assays were not active against animal parasites in the assays described in example 1. Found therein by A 1 -A 5 The compounds which form rings without halogen substitution are active against agrochemical parasites but not against animal parasites. Wherein is represented by A 1 -A 5 The compounds in which the ring formed is substituted by at least one halogen are active against animal parasites.
In a first aspect, the compounds according to the invention are further defined as follows
R 1 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl (C)Radical), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may optionally be one or more selected from the group consisting ofThe following substituents are substituted: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Halogenated compoundsAlkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl,N((C 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 11 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) Alkyl group
H、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) A haloalkyl group;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, R 1 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy groups.
In one embodiment of the invention and/or embodiments thereof, R 1 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Haloalkoxy groups.
In one embodiment of the invention and/or embodiments thereof, R 1 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 1 -C 6 ) Haloalkyl selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group.
In one embodiment of the invention and/or embodiments thereof, R 1 Is H.
In one embodiment of the invention and/or embodiments thereof, R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, ((C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 。
In one embodiment of the invention and/or embodiments thereof, R 2 Is selected from H, F, cl, br, I, CN%C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy and S- (halo) 5 。
In one embodiment of the invention and/or embodiments thereof, R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Haloalkoxy and S- (halo) 5 。
In one embodiment of the invention and/or embodiments thereof, R 2 Selected from H, F, cl, br, CN, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl and S- (halo) 5 。
In one embodiment of the invention and/or embodiments thereof, R 2 Selected from H, F, cl, br, CN, CH 3 、CHF 2 、CF 3 、OCHF 2 And S- (halo) 5 。
In one embodiment of the invention and/or embodiments thereof, R 2 Selected from H, F, cl.
In one embodiment of the invention and/or embodiments thereof, R 2 Selected from F and Cl.
In one embodiment of the invention and/or embodiments thereof, R 2 Is Cl.
In one embodiment of the invention and/or embodiments thereof, R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups.
In one embodiment of the present invention and/or the present inventionIn one embodiment, R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) Halogenated alkenyl groups.
In one embodiment of the invention and/or embodiments thereof, R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group.
In one embodiment of the invention and/or embodiments thereof, R 2 Selected from H, F, cl and Br.
In one embodiment of the invention and/or embodiments thereof, R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, ((C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 。
In one embodiment of the invention and/or embodiments thereof, R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups.
In one embodiment of the invention and/or embodiments thereof, R 3 Selected from H, F, cl, br, I, CH 3 、CF 3 、CHF 2 、OCF 3 、OCH 3 、CH＝CHF、C≡C、CH＝CH 2 。
In one embodiment of the invention and/or embodiments thereof, R 3 Selected from H, F, cl, br and I.
In one embodiment of the invention and/or embodiments thereof, R 3 Selected from H, F, cl, br.
In one embodiment of the invention and/or embodiments thereof, R 3 Selected from H, F and Cl.
In one embodiment of the invention and/or embodiments thereof, R 3 Is H or F.
In one embodiment of the invention and/or embodiments thereof, R 3 Is H.
In one embodiment of the invention and/or embodiments thereof, R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups.
In one embodiment of the invention and/or embodiments thereof, R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups.
In one embodiment of the invention and/or embodiments thereof, R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups.
In one embodiment of the invention and/or embodiments thereof, R 3 Selected from H, F, cl, br and I.
In one embodiment of the invention and/or embodiments thereof, R 4 Selected from H, F, cl, br, I, CN, NH, NO 2 、(C 1 -C 6 ) Alkyl, ((C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 。
In one embodiment of the invention and/or embodiments thereof, R 4 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy and S- (halo) 5 。
In one embodiment of the invention and/or embodiments thereof, R 4 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl (C) 1 -C 6 ) Alkoxy, (C) 2 -C 6 ) Haloalkenyl and S- (halo) 5 。
In one embodiment of the invention and/or embodiments thereof, R 4 Selected from H, F, cl, br, CH 3 、CF 3 、OCH 3 、CH＝CHF、C≡C、CH＝CH 2 And SF (sulfur hexafluoride) 5 。
In one embodiment of the invention and/or embodiments thereof, R 4 Selected from H, F, cl and Br.
In one embodiment of the invention and/or embodiments thereof, R 4 Selected from H, F and Cl.
In one embodiment of the invention and/or embodiments thereof, R 4 Is Cl.
In one embodiment of the invention and/or embodiments thereof, R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups.
In one embodiment of the invention and/or embodiments thereof, R 4 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) Halogenated alkenyl groups.
In one embodiment of the invention and/or embodiments thereof, R 4 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group.
In one embodiment of the invention and/or embodiments thereof, R 4 Selected from H, F, cl, br.
In one embodiment of the invention and/or embodiments thereof, R 5 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl、C(＝O)O(C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl group 2 、NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl.
In one embodiment of the invention and/or embodiments thereof, R 5 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) O (C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH-C (=o) O (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 5 Selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 5 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group.
In one embodiment of the invention and/or embodiments thereof, R 5 Selected from H, F, cl, br, I, CH 3 、OCH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, R 5 Selected from H, F, cl, br and I.
In one embodiment of the invention and/or embodiments thereof, R 5 Selected from H, F and Cl.
In one embodiment of the invention and/or embodiments thereof, R 5 Is H or F.
In one embodiment of the invention and/or embodiments thereof, R 5 Selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 5 Selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 。
In one embodiment of the invention and/or embodiments thereof, R 5 Selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 5 Selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl group 2 、NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl.
In one embodiment of the invention and/or embodiments thereof, R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) O (C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH-C (=o) O (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 6 Selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 6 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl group sum (C) 2 -C 6 ) Halogenated alkenyl groups.
In one embodiment of the invention and/or embodiments thereof, R 6 Selected from H, F, cl, br, I, CH 3 、OCH 3 Ch=chf, ch=ch, and CF 3 。
In one embodiment of the invention and/or embodiments thereof, R 6 Selected from H, F, cl, br, I, CH 3 、OCH 3 Ch=chf, ch=ch, and CF 3 。
In one embodiment of the invention and/or embodiments thereof, R 6 Selected from H, F, cl, br and CH 3 。
In one embodiment of the invention and/or embodiments thereof, R 6 Selected from H, F, cl and CH 3 。
In one embodiment of the invention and/or embodiments thereof, R 6 Is H or F.
In one embodiment of the invention and/or embodiments thereof, R 6 Selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 。
In one embodiment of the invention and/or embodiments thereof, R 6 Selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 。
In one embodiment of the invention and/or embodiments thereof, R 6 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 7 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl group 2 、NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl.
In one embodiment of the invention and/or embodiments thereof, R 7 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) Halogenated compoundsAlkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) O (C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH-C (=o) O (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 7 Selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 7 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl group sum (C) 2 -C 6 ) Halogenated alkenyl groups.
In one embodiment of the invention and/or embodiments thereof, R 7 Selected from H, F, cl, br, I, CH 3 、OCH 3 Ch=chf, ch=ch, and CF 3 。
In one embodiment of the invention and/or embodiments thereof, R 7 Selected from H,F、Cl、Br、I、CH 3 、OCH 3 Ch=chf, ch=ch, and CF 3 。
In one embodiment of the invention and/or embodiments thereof, R 7 Selected from H, F, cl, br and I.
In one embodiment of the invention and/or embodiments thereof, R 7 Selected from H, F and Cl.
In one embodiment of the invention and/or embodiments thereof, R 7 Is H or F.
In one embodiment of the invention and/or embodiments thereof, R 7 Selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group.
In one embodiment of the invention and/or embodiments thereof, R 8 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl group 2 、NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl.
In one embodiment of the invention and/or embodiments thereof, R 8 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) O (C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH-C (=o) O (C) 1 -C 6 ) An alkyl group.
In the present invention andin one embodiment of/or embodiments thereof, R 8 Selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, C 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 8 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl group sum (C) 2 -C 6 ) Halogenated alkenyl groups.
In one embodiment of the invention and/or embodiments thereof, R 8 Selected from H, F, cl, br, I, CH 3 、OCH 3 Ch=chf, ch=ch, and CF 3 。
In one embodiment of the invention and/or embodiments thereof, R 8 Selected from H, F, cl, br, I, CH 3 、OCH 3 Ch=chf, ch=ch, and CF 3 。
In one embodiment of the invention and/or embodiments thereof, R 8 Selected from H, F, cl, br and CH 3 。
In one embodiment of the invention and/or embodiments thereof, R 8 Selected from H, F, cl and CH 3 。
In one embodiment of the invention and/or embodiments thereof, R 8 Is H or F.
In one embodiment of the invention and/or embodiments thereof, R 8 Selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 9 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl group 2 、NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl.
In one embodiment of the invention and/or embodiments thereof, R 9 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) O (C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH-C (=o) O (C) 1 -C 6 ) An alkyl group.
The compound and use according to any one of the preceding claims, wherein R 9 Selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, C 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group.
In one implementation of the invention and/or embodiments thereofIn the scheme, R 9 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Alkenyl group sum (C) 2 -C 6 ) Halogenated alkenyl groups.
In one embodiment of the invention and/or embodiments thereof, R 9 Selected from H, F, cl, br, I, CH 3 、OCH 3 Ch=chf, ch=ch, and CF 3 。
In one embodiment of the invention and/or embodiments thereof, R 9 Selected from H, F, cl, br, I, CH 3 、OCH 3 Ch=chf, ch=ch, and CF 3 。
In one embodiment of the invention and/or embodiments thereof, R 9 Selected from H, F, cl, br and I.
In one embodiment of the invention and/or embodiments thereof, R 9 Selected from H, F and Cl.
In one embodiment of the invention and/or embodiments thereof, R 9 Is H or F.
In one embodiment of the invention and/or embodiments thereof, R 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -ch=, =ch-, -n=, =n-, -NH-, and-O-.
In one embodiment of the invention and/or embodiments thereof, R 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -ch=, =ch-, -n=, =n-and-NH-.
In one embodiment of the invention and/or embodiments thereof, the R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN.
In one embodiment of the invention and/or embodiments thereof, the R 6 And R is 7 The ring formed is optionally covered withOne or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl.
In one embodiment of the invention and/or embodiments thereof, the R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl.
In one embodiment of the invention and/or embodiments thereof, the R 6 And R is 7 The ring formed is unsubstituted.
In one embodiment of the invention and/or embodiments thereof, R 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -ch=, =ch-, -n=, =n-, -NH-, and-O-.
In one embodiment of the invention and/or embodiments thereof, R 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -ch=, =ch-, -n=, =n-and-NH-.
In one embodiment of the invention and/or embodiments thereof, the R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN.
In one embodiment of the invention and/or embodiments thereof, the R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl.
In one embodiment of the invention and/or embodiments thereof, the R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl.
In one embodiment of the invention and/or embodiments thereof, the R 7 And R is 8 The ring formed is unsubstituted.
In one embodiment of the invention and/or embodiments thereof, R 10 Selected from H、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl (thianyl), phenyl and (C 1 -C 6 ) An alkylphenyl group.
In one embodiment of the invention and/or embodiments thereof, R 10 Selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl.
In one embodiment of the invention and/or embodiments thereof, R 11 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy and (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 。
In one embodiment of the invention and/or embodiments thereof, R 11 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 And (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, R 11 Selected from H, F, cl, br, I and CH 3 。
In one embodiment of the invention and/or embodiments thereof, R 11 Selected from H, F, cl and CH 3 。
In one embodiment of the invention and/or embodiments thereof, R 11 Is H.
In one embodiment of the invention and/or embodiments thereof, R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy and (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 。
In one embodiment of the invention and/or embodiments thereof, R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl groups; (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups.
In one embodiment of the invention and/or embodiments thereof, R 12 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group.
In one embodiment of the invention and/or embodiments thereof, R 12 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, R 12 Is H or F.
In one embodiment of the invention and/or embodiments thereof, R 12 Is H.
In one embodiment of the invention and/or embodiments thereof, R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And triazolyl.
In one embodiment of the invention and/or embodiments thereof, R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups.
In one embodiment of the invention and/or embodiments thereof, R 13 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group.
In one embodiment of the invention and/or embodiments thereof, R 13 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group.
In one embodiment of the invention and/or embodiments thereof, R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, R 13 Is Cl or F.
In one embodiment of the invention and/or embodiments thereof, R 13 Is Cl.
In one embodiment of the invention and/or embodiments thereof, R 14 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy and (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 。
In one embodiment of the invention and/or embodiments thereof, R 14 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups.
In one embodiment of the invention and/or embodiments thereof, R 14 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group.
In one embodiment of the invention and/or embodiments thereof, R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, R 14 Selected from H and F.
In one embodiment of the invention and/or embodiments thereof, R 14 Is H.
In one embodiment of the invention and/or embodiments thereof, R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl and (C) 1 -C 6 ) A haloalkyl group.
In one embodiment of the invention and/or embodiments thereof, R 15 Selected from H, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group.
In one embodiment of the invention and/or embodiments thereof, R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, R 15 Is H.
In one embodiment of the present invention and/or embodiments thereof,
R 1 selected from H, F and Cl;
R 2 selected from H, F and Cl;
R 3 selected from H, F and Cl;
R 4 selected from H, F and Cl;
R 5 selected from H, F, cl, br and I;
R 6 selected from H, F and Cl, br and CH 3 ；
R 7 Selected from H, F, cl, br and I;
R 8 selected from H, F, cl and Br and CH 3 ；
R 9 Selected from H, F, cl, br and I;
R 11 is H;
R 12 selected from H, F, CL, CH 3 、CF 3 ；
R 13 Selected from H, F, cl, CF 3 And CH (CH) 3 ；
R 14 Is H or F; and
R 15 selected from H and CH 3 。
In one embodiment of the present invention and/or embodiments thereof,
R 1 is H;
R 2 selected from H, F and Cl;
R 3 selected from H, cl, F and Br;
R 4 is H, F, cl;
R 5 selected from H, F and Cl;
R 6 selected from H, F and Cl and CH 3 ；
R 7 Selected from H, F and Cl;
R 8 selected from H, F, cl and CH 3 ；
R 9 Selected from the group consisting ofH. F and Cl;
R 11 is H;
R 12 selected from H, F and Cl;
R 13 selected from H, F and Cl;
R 14 is H;
R 15 selected from H and CH 3 。
In one embodiment of the present invention and/or embodiments thereof,
R 1 is H;
R 2 selected from H, F and Cl;
R 3 selected from H, cl, F and Br;
R 4 is H, F, cl;
R 5 selected from H, F and Cl;
R 6 selected from H, F and CH 3 ；
R 7 Selected from H, F and Cl;
R 8 Selected from H, F and CH 3 ；
R 9 Selected from H, F and Cl;
R 11 is H;
R 12 selected from H and F;
R 13 selected from F and Cl;
R 14 is H;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, R 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br.
In one embodiment of the invention and/or embodiments thereof, R 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, R 5 、R 6 、R 7 、R 8 、R 9 At least one of them is F。
In one embodiment of the invention and/or embodiments thereof, R 5 、R 6 、R 7 、R 8 、R 9 At least two of which are substituents selected from the group consisting of: F. cl and Br.
In one embodiment of the invention and/or embodiments thereof, R 5 、R 6 、R 7 、R 8 、R 9 At least two of which are substituents selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, R 5 、R 6 、R 7 、R 8 、R 9 At least two of which are F.
In one embodiment of the invention and/or embodiments thereof, R 5 、R 6 、R 7 At least one of which is a substituent selected from the group consisting of: F. cl and Br.
In one embodiment of the invention and/or embodiments thereof, R 5 、R 6 、R 7 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, R 5 、R 6 、R 7 At least one of which is F.
In one embodiment of the invention and/or embodiments thereof, R 5 、R 7 At least one of which is a substituent selected from the group consisting of: F. cl and Br.
In one embodiment of the invention and/or embodiments thereof, R 5 、R 7 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, R 5 、R 7 At least one of which is F.
In one embodiment of the invention and/or embodiments thereof, R 5 And R is 7 Each is a substituent selected from the group consisting of: F. cl and Br.
In one embodiment of the invention and/or embodiments thereof, R 5 And R is 7 Each is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, R 5 And R is 7 Each is F.
In one embodiment of the invention and/or embodiments thereof, A 1 、A 2 、A 3 、A 4 、A 5 0, 1 or 2 of which are N.
In one embodiment of the invention and/or embodiments thereof, the compound is a prodrug and a 1 、A 2 、A 3 、A 4 、A 5 Is n=o.
In one embodiment of the invention and/or embodiments thereof, A 1 、A 2 、A 3 、A 4 、A 5 0, 1 or 2 of (a) are n=o.
In one embodiment of the present invention and/or embodiments thereof,
A 1 Is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N.
In one embodiment of the present invention and/or embodiments thereof,
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 Wherein 0 or 1 is N.
In one embodiment of the present invention and/or embodiments thereof,
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N
A 3 Is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (II)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof, wherein R 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I, wherein R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 12 、R 13 、R 14 、R 15 、A 1 、A 2 、A 3 、A 4 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (II)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof, wherein
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl group,(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached form a ring containing 5 or 6 atoms, whereThe ring atoms are selected from: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) Alkyl group
H、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) A haloalkyl group;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, brI。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (II)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof, wherein
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N,
A 2 is CR (CR) 6 N=o or N
A 3 Is CR (CR) 7 N=o or N
A 4 Is CR (CR) 8 N=o or N
A 5 Is CR (CR) 9 N=o or N
Wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (II)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H,F、Cl、Br、I、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of:-CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (II)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (II)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (III)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 13 、R 14 、R 15 、A 1 、A 2 、A 3 、A 4 And A 5 As defined elsewhere in this specification,
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (III)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein A is 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
Wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl group),NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl group、S(O)(C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Halogen-free foodAlkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) Alkyl group
H、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) A haloalkyl group;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (III)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl group、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N,
A 2 is CR (CR) 6 N=o or N
A 3 Is CR (CR) 7 N=o or N
A 4 Is CR (CR) 8 N=o or N
A 5 Is CR (CR) 9 N=o or N
Wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl groupsC(＝O)-O-(C 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) Alkyl group-C(＝O)lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (III)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (III)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (III)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H,F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl;
R 14 is H;
R 15 is H;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (IV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 12 、R 13 、R 14 、A 1 、A 2 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (IV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl radicals、(C 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiaThe phenoyl and triazolyl groups may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached form a group containing 5 orA 6 atom ring wherein the ring forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) Alkyl group
H、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) A haloalkyl group;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (IV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N,
A 2 Is CR (CR) 6 N=o or N
A 3 Is CR (CR) 7 N=o or N
A 4 Is CR (CR) 8 N=o or N
A 5 Is CR (CR) 9 N=o or N
Wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (IV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (IV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (IV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (V)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 12 、R 13 、R 15 、A 1 、A 2 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (V)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N or n=o;
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy group,(C 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Halogenated compoundsAlkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenesRadical (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl,Cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) Alkyl group
H、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) A haloalkyl group;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (V)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I、CN、NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (V)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (V)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (V)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 13 、A 1 、A 2 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N or n=o;
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, and pyriOxazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogen-free foodCycloalkenyl group (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of the alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, and ringAlkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group)(C(＝O)(C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) Alkyl group；
Or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl (C)Radical, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Naphthene Radical), (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N or n=o;
R 5 selected from H, F, cl, br,I、CN、NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more members selected from the group consisting ofIs substituted by a substituent of (a): (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 No more than 3 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-,wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VI)
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And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 Selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 、R 3 、R 4 、R 12 、R 13 、R 14 、R 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H,F、Cl、CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 I。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 、R 3 、R 4 、R 12 、R 13 、R 14 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy radicalRadical (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl group sum [ ]C 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (VIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (IX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 、R 3 、R 4 、R 12 、R 13 、R 14 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (IX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated ringAlkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) HaloalkanesRadical (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (IX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (IX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (IX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (IX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (X)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 12 、R 13 、R 14 、R 15 、A 2 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (X)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 2 Is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 3 、A 4 And A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O)) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogen-free foodSubstituted cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, haloringAlkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl (C)radical-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl)、N((C 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy group-(C 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Halogen-free foodSubstituted alkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group;
wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f (F)Cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (X)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 3 、A 4 And A 5 Wherein no more than 2 of the N groups are N or n=o;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 Selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (X)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 3 、A 4 And A 5 Not more than 2 of which are N;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl groups、(C 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (X)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 3 、A 4 And A 5 0 or 1 of (a) is N;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 ；
Wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (X)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
Wherein A is 2 0 or 1 of (2) is N;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H;
wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 12 、R 13 、R 14 、R 15 、A 1 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 3 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) Halogen-free foodSubstituted alkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: f (F) 、Cl、Br、I、CN、OH、NH(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl,Br、I、H、CN、CHO、NHOH、NO、NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group;
wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 3 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XI)
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And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 3 、A 4 、A 5 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 Selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 3 、A 4 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkene (E)Radical (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 ；
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
Wherein A is 1 0 or 1 of (2) is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H;
wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 13 、R 14 、R 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl group(C 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 2 、R 3 、R 4 、R 13 、R 14 、R 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl group、S(O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 13 、R 14 、R 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 13 Selected from H,F、Cl、Br、I、CN、NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H,(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 7 、R 8 、R 9 、R 13 、R 14 、R 15 、A 2 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein A is 2 Is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
Wherein A is 2 、A 3 、A 4 And A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl andthe triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl (C)Radical) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) Alkyl (C)A base;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached form a chain containing 5 or 6 atoms A ring, wherein the ring-forming atoms are selected from: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 、N＝CH-Phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group;
wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 3 、A 4 And A 5 Wherein no more than 2 of the N groups are N or n=o;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN,(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 3 、A 4 And A 5 Not more than 2 of which are N;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally covered with one or moreA substituent selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 3 、A 4 And A 5 0 or 1 of (a) is N;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached form a group containing 5 or 6A ring of atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 ；
Wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
R 6 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H;
wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 7 、R 8 、R 9 、R 13 、R 14 、R 15 、A 1 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 3 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN,CHO、NHOH、NO、NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O)O(C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy group, alkyl group,Haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O)(C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group;
wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 3 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 3 、A 4 、A 5 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-, -n=, =n-, and-NH-, where R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 3 、A 4 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 Selected from H and CH 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
R 5 Selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl;
R 14 is H;
R 15 is H;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 12 、R 13 And R is 14 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from the group consisting ofH、F、Cl、Br、(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 12 is H;
R 13 is Cl;
R 14 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 12 、R 13 、R 14 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl group,(C 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 12 selected from H, F、Cl、CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 12 is H;
R 13 is Cl;
R 14 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 12 、R 13 And R is 14 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy radicalRadical (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 12 is H;
R 13 is Cl;
R 14 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XX)
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And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 7 、R 8 、R 9 、R 12 、R 13 、R 14 、A 2 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 2 Is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 3 、A 4 And A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Halogenated alkenyl group,(C 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Halogen-free foodSubstituted alkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
Wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridyl, and the like,S(＝NCN)((C 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) Alkyl (C)base-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl group,S(O)(＝NCN)((C 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
Wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 3 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C%＝O)lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 3 、A 4 And A 5 Not more than 2 of which are N;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 Is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 3 、A 4 And A 5 0 or 1 of (a) is N;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more members selected from the group consisting ofSubstituent substitution: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
R 6 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 7 、R 8 、R 9 、R 12 、R 13 、R 14 、A 1 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 3 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy groups、(C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O)O(C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 With atoms to which they are attachedAnd forming a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl group、S(O)(C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 3 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 3 、A 4 、A 5 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 Selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 3 、A 4 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
R 5 Selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 2 、R 3 、R 4 、R 12 、R 13 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) Haloalkyl-S(O) 2 NH 2 And S- (halo) 5 ；
R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 15 selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl group、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 12 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 12 is H or F;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 12 is H;
R 13 is Cl;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 12 、R 13 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 15 selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) HaloalkanesAn oxy group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br,I、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 12 is H or F;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 12 is H;
R 13 is Cl;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 12 、R 13 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 15 selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 12 is H or F;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 12 is H;
R 13 is Cl;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 7 、R 8 、R 9 、R 12 、R 13 、R 15 、A 2 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 2 Is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
Wherein A is 2 、A 3 、A 4 And A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl group, N (-), N)C 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from the group consisting ofF、Cl、Br、I、H、CN、CHO、NHOH、NO、NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy group、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=NCN)((C 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 15 selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group;
wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 3 、A 4 And A 5 Wherein no more than 2 of the N groups are N or n=o;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 3 、A 4 And A 5 Not more than 2 of which are N;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 3 、A 4 And A 5 0 or 1 of (a) is N;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 15 selected from H and CH 3 ；
Wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
R 6 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 15 is H;
wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 2 、R 3 、R 4 、R 5 、R 7 、R 8 、R 9 、R 12 、R 13 、R 14 、R 15 、A 1 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 3 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenylPyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 15 selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group;
wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 3 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, Cl、CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 3 、A 4 、A 5 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 3 、A 4 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 12 is H or F;
R 13 is Cl or F;
R 15 selected from H and CH 3 ；
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
R 5 Selected from H, F,Cl, CN and (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 15 is H
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 And R is 13 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 13 is Cl or F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 13 is Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 And R is 13 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl group、S(C 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Halogenated olefinsRadical (C) 1 -C 6 ) Haloalkoxy groups;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 13 is Cl or F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 13 is Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 And R is 13 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl group、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 13 is Cl or F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 13 is Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 7 、R 8 、R 9 、R 13 、A 2 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 2 Is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 3 、A 4 And A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) Haloalkanesbase-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br、I、CN、OH、NH(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
Each of alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 And they are connected withThe attached atoms together form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 3 、A 4 And A 5 Wherein no more than 2 of the N groups are N or n=o;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein consists ofR 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
Wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 3 、A 4 、A 5 Not more than 2 of which are N;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
Wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 3 、A 4 And A 5 0 or 1 of (a) is N;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝(N), =ch-, -n=, =n-, and-NH-, where R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
R 6 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl;
wherein R is 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 7 、R 8 、R 9 、R 13 、A 1 、A 3 、A 4 And A 5 As defined elsewhere in this specification and wherein R 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 3 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) HaloalkanesBase, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH((C 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, whereinFrom R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 3 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy radicalRadical (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl and Br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 3 、A 4 、A 5 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 Selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
Wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXI)
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And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 3 、A 4 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 13 is Cl or F;
wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
R 5 Selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl;
wherein R is 5 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: f and Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 2 、R 3 、R 4 、R 6 、R 7 、R 8 、R 9 、R 13 、R 14 、R 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl group、S(C 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxyHaloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
Wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl (C)Oxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of:-CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl groups、(C 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkyl (C)Oxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and FCl；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 6 、R 8 、R 9 、R 13 、R 14 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl group),NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
Wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl group、S(O)(C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F.Cl、Br、I、CN、OH、NH(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N%(C 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIII)
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And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 2 、R 3 、R 4 、R 6 、R 8 、R 9 、R 13 、R 14 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O)) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl group),NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 7 、R 8 、R 9 、R 12 、R 13 And R is 14 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl radical, (C 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy group, alkyl groupHaloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl group) (C ]＝O)(C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl group, N (C 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl,(C 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group) 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally covered withOne or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 6 、R 8 、R 9 、R 12 、R 13 And R is 14 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl (C)Radical), imidazolyl radical, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl group,NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl group、(C 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl group、(C 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) Alkyl group-C(＝O)lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl (C)Radical, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 Is H;
R 13 is Cl;
R 14 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 8 、R 9 、R 12 、R 13 And R is 14 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl radicals、NH(S(O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN,(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVIII)
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And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 7 、R 8 、R 9 、R 12 、R 13 、R 15 、A 1 、A 2 、A 3 、A 4 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl radicals, (-)C 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl,thiazolyl, thienyl and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O))O(C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 With atoms to which they are attachedAnd forming a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl group、S(O)(C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 15 selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from The following substituents are substituted: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl group、NHC(＝O)R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached form a ring containing 5 or 6 atomsWherein the ring-forming atoms are selected from: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 6 、R 8 、R 9 、R 12 、R 13 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O)(C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkyl (C)Phenyl and NH (S (O)) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazoleThe base group of the modified polyester resin is a modified polyester resin,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 15 selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=O)lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl group,((C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Halogen-free foodSubstituted alkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XL)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 2 、R 3 、R 4 、R 6 、R 8 、R 9 、R 12 、R 13 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XL)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl、(C 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C(=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl (C)Radical, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl group,(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 15 selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XL)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl (C)
Radical, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XL)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XL)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XL)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 7 、R 8 、R 9 And R is 13 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN,Thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl group,CH(＝NO(C 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group)、N((C 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=O)O-(C 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Halogen-free foodSubstituted alkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 6 、R 8 、R 9 And R is 13 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Halogen-free foodSubstituted alkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O)(C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=NCN)((C 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may optionally be substituted with one or moreA plurality of substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 8 、R 9 And R is 13 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloAlkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 2 、R 3 、R 4 、R 6 、R 7 、R 8 、R 9 、R 12 、R 13 、R 14 、R 15 、A 2 、A 3 、A 4 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 2 Is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 3 、A 4 And A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl (C)Radical (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl group, S(C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl,Phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. Cl、Br、I、CN、OH、NH(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I, CN;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-, -NH-and-O-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F, cl, br, I and CN;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 3 、A 4 And A 5 Not more than 2 of which are N;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and (C) 1 -C 6 ) A haloalkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 8 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl, F and Cl;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 3 、A 4 And A 5 0 or 1 of (a) is N;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 7 Selected from H, F and Cl;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -, -CH=, =CH- -n=. =n-and-NH-, wherein R is represented by 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: CH (CH) 3 F and Cl;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 Selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 2 is CR (CR) 6 Or N;
A 3 is CR (CR) 7 ；
A 4 Is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
R 6 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 7 selected from H and F;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 6 、R 8 、R 9 、R 12 、R 13 、R 14 、R 15 、A 1 、A 2 、A 4 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group-O(C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -
R 8 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Halogenated olefinsRadical (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl group, imidazoleRadical, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 4 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=O)lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 4 、A 5 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl,NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Halogen-free foodAlkyl substituted;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 4 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 Is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 4 is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 8 、R 9 、R 12 、R 13 、R 14 、R 15 、A 2 、A 4 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 2 Is CR (CR) 6 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 4 、A 5 No more than 2 of which are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy compoundsRadical, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxaOxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynylThe halo alkenyl, cycloalkenyl, cycloalkyl, halo cycloalkenyl, halo cycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl groups may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 4 、A 5 No more than 2 of which are N or n=o;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 2 is CR (CR) 6 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 4 、A 5 No more than 2 of which are N;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 2 is CR (CR) 6 Or N;
A 4 is CR (CR) 8 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 4 、A 5 0 or in (B)1 is N;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 2 is CR (CR) 6 Or N;
A 4 is CR (CR) 8 ；
A 5 Is CR (CR) 9 ；
R 6 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 Selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or of its embodiments, the invention relates to a compound of formula (XLVIIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLVIIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XLIXa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (L)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to a compound of formula (La)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or of its embodiments, the invention relates to compounds of formula (LI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LIIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LIIIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LIVa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LIVb)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LVa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LVIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or of its embodiments, the invention relates to a compound of formula (LVIIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LVIIIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXIIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXIIIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXIVa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In a particular embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 8 、R 12 、R 13 、R 14 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl groups, NH (S)(O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
Wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 )alkyl。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 .
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, Br、(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 8 、R 13 、R 14 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl group,(C 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) NaphtheneRadical CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl、NH((C 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl radicals, (-)C 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 8 、R 12 、R 13 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenesRadical (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H,CN、CHO、NHOH、NO、NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl group, NH-C(＝O)O(C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 15 selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXIX)
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And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl group,(C 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H,F、Cl、CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) Alkyl (C)A base;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 12 is H;
R 13 is Cl;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 8 、R 12 、R 13 And R is 14 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) Haloalkyl-S(O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl group,S(O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) Alkyl (C)A phenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 8 And R is 13 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Halogenated compoundsAlkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl group),NHC(＝O)R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl group、S(O)(C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl (C)Radical- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl,NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 8 Selected from H and F;
R 13 is Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 8 、R 9 、R 12 、R 13 、R 14 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridyl, S(＝NCN)((C 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of the alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkylHalo cycloalkenyl, halo cycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O)(C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl group,(C 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl (C)Radical, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) Alkyl group-C(＝O)lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F；
R 13 Is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 2 、R 3 、R 4 、R 5 、R 8 、R 9 、R 13 、R 14 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) CycloolefinsRadical (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazoleThe groups, pyridinyl, thiazolyl, thiophenyl and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy groupAnd C (=O) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl group,(C 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 14 selected from H and F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl;
R 14 is H;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 8 、R 9 、R 12 、R 13 And R is 14 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy group,
(C 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) NaphtheneRadical (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, and,Pyridyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenesRadical (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl,Cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group)(C(＝O)(C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl radicals, (-/-, etc.)C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Ring(s)Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkyl group；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 14 Selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 5 selected from H, F, Cl、CN、NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 14 selected from H and F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 14 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 8 、R 9 、R 12 、R 13 And R is 15 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Halogen-free foodSubstituted alkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) NaphtheneRadical (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of alkoxy, alkyl, haloalkoxy, haloalkyl,alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 15 selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 12 is H or F;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 12 is H;
R 13 is Cl;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 8 、R 9 And R is 13 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Halogen-free foodSubstituted alkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached form a group containing 5 orA 6 atom ring wherein the ring forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) NaphtheneRadical (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl (C)
Radical, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 8 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 8 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 Is Cl or F.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 8 selected from H and F;
R 9 selected from H and F;
R 13 is Cl.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 5 、R 6 、R 9 、R 13 、R 15 、A 1 、A 2 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein A is 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Halogen-free foodSubstituted alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynylThe halo alkenyl, cycloalkenyl, cycloalkyl, halo cycloalkenyl, halo cycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl groups may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 5 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from the group consisting of(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 Selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 3 、R 5 、R 6 、R 9 、R 13 、R 15 、A 1 、A 2 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein A is 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 3 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Halogenated compoundsAlkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl group,NH(C 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 5 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydroFuryl and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br and I;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 3 、R 6 、R 9 、R 13 、R 15 、A 2 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 2 Is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl group,(C 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thiopheneA group and a triazole group, wherein the triazole group,
Wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 5 Not more than 2 of which are N;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 2 Is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 5 0 or 1 of (a) is N;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) Alkyl-)C(＝O)lR 10 ；
R 9 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br and I;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 ；
R 5 Selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 2 、R 4 、R 5 、R 6 、R 9 、R 13 、R 15 、A 1 、A 2 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Halogen-free foodSubstituted alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) Alkyl group-C(＝O)lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 5 Not more than 2 of which are N;
R 5 Selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 4 、R 6 、R 9 、R 13 、R 15 、A 2 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 2 Is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidineRadicals, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 5 Not more than 2 of which are N;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 5 0 or 1 of (a) is N;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 4 selected from H, F, cl, br;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 ；
R 6 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 2 、R 4 、R 5 、R 6 、R 13 、R 15 、A 1 And A 2 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
wherein A is 1 、A 2 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O)) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
wherein A is 1 、A 2 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
wherein A is 1 、A 2 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 10 Selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) HaloalkanesA base;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
wherein A is 1 、A 2 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 10 Selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 4 、R 6 、R 13 、R 15 And A 2 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein A is 2 Is CR (CR) 6 N=o or N;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO、NHOH、NO、NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O)O(C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 N=o or N;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 2 is CR (CR) 6 Or N;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 10 Selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 2 is CR (CR) 6 Or N;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 10 Selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 4 selected from H, F, cl, br;
A 2 is CR (CR) 6 Or N;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 4 、R 5 、R 13 、R 15 And a is as defined elsewhere in the specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl、S(O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of the alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, haloalkenylThe groups, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Ring(s)Alkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothiophenyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 10 Selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 Selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 4 selected from H, F, cl, br;
A 1 Is CR (CR) 5 Or N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 4 、R 5 、R 9 、R 13 、R 15 、A 1 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl group,(C 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl group),Imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) HaloalkanesRadical (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 5 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXV)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXV)
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And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 5 is CR (CR) 9 ；
R 5 Selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 3 、R 5 、R 6 、R 9 、R 13 、R 15 、A 1 、A 2 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 3 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy radicalRadical (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of the alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, haloalkenylThe groups, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridyl, thiazolyl, thienyl and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl group、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 5 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVI)
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And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br and I;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 3 、R 5 、R 9 、R 13 、R 15 、A 2 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 2 Is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl group((C 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
Wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinylThiazolyl, thienyl and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -an alkaneRadical (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 5 Not more than 2 of which are N;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 2 Is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 5 0 or 1 of (a) is N;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br and I;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 ；
R 6 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 2 、R 3 、R 4 、R 6 、R 9 、R 13 、R 15 、A 2 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 2 Is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 2 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 6 Selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl group,S(O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
Wherein A is 2 、A 5 Not more than 2 of which are N;
R 6 selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
R 3 selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 2 、A 5 0 or 1 of (a) is N;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXVIII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 2 Selected from H, F, cl, br;
R 3 selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 ；
R 6 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 3 、R 4 、R 5 、R 6 、R 9 、R 13 、R 15 、A 1 、A 2 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 3 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl、C(＝O)O(C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl (C)Base group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 5 Not more than 2 of which are N;
R 5 Selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (LXXXIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XC)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 3 、R 4 、R 5 、R 6 、R 9 、R 15 、A 1 、A 2 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XC)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 3 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl group,C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl (C)Radical, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl (C)Radical (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl group, S(C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XC)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XC)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 5 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XC)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 2 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 Selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XC)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
A 5 is CR (CR) 9 ；
Wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XCI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein R is 3 、R 5 、R 6 、R 13 、R 15 、A 1 And A 2 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XCI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
wherein A is 1 、A 2 Wherein no more than 2 of the N groups are N or n=o;
R 3 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl (C)Radical, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo of、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o)lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XCI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
wherein A is 1 、A 2 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XCI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
wherein A is 1 、A 2 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 6 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 10 Selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XCI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
wherein A is 1 、A 2 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F, NH (C) 1 -C 6 ) Alkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 10 Selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XCI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br and I;
A 1 is CR (CR) 5 Or N;
A 2 is CR (CR) 6 Or N;
wherein A is 1 Or A 2 Wherein 0 or 1 is N;
R 5 selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 6 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XCII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein R is 3 、R 4 、R 5 、R 9 、R 13 、R 15 、A 1 And A 5 As defined elsewhere in this specification.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XCII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
A 1 Is CR (CR) 5 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 3 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Halogenated compoundsAlkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl (C)Group, oxazolyl, phenyl, pyrazolyl, pyridyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, heterocycle, aryl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, Br、I、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) A haloalkyl group;
R 15 selected from H, (C) 1 -C 6 ) An alkyl group.
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XCII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 1 -C 6 ) Haloalkoxy groups;
A 1 is CR (CR) 5 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 5 Wherein no more than 2 of the N groups are N or n=o;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl group、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F, cl, br, I, CN, NO 2 、NH 2 、＝O、NH(C 1 -C 6 ) Alkyl, N ((C) 1 -C 6 ) Alkyl group 2 、(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、C(＝O)(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Haloalkenyl and C (=o) -O- (C) 1 -C 6 ) An alkyl group;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, ((C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, piperidinyl, pyrrolidinyl, tetrahydrothienyl, tetrahydrothiopyranyl, phenyl and (C) 1 -C 6 ) An alkylphenyl group;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XCII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
Wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 selected from H, F, cl, br, I, CN, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl and (C) 2 -C 6 ) A haloalkenyl group;
A 1 is CR (CR) 5 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 5 Not more than 2 of which are N;
R 5 selected from H, F, cl, br, I, CN, NO 2 、NH(C 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, NHC (=o) R 10 And N (C) 1 -C 6 ) alkyl-C (=o) lR 10 ；
R 9 Selected from H, F, cl, NH (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 selected from H, F, cl, CH 3 And CF (compact F) 3 ；
R 15 Selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XCII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br, I, (C) 1 -C 6 ) Haloalkyl and (C) 1 -C 6 ) Haloalkoxy groups;
R 4 Selected from H, F, cl, br, (C) 1 -C 6 ) Alkyl and (C) 1 -C 6 ) A haloalkyl group;
A 1 is CR (CR) 5 Or N;
A 5 is CR (CR) 9 Or N;
wherein A is 1 、A 5 0 or 1 of (a) is N;
R 5 selected from H, F, cl, CN, NO 2 、NH(C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H, F and NH (C) 1 -C 6 ) An alkyl group;
R 10 selected from (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Cycloalkyl, tetrahydrofuranyl, and phenyl;
R 13 is Cl or F;
R 15 selected from H and CH 3 。
In one embodiment of the invention and/or embodiments thereof, the invention relates to compounds of formula (XCII)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
wherein the method comprises the steps of
R 3 Selected from H, F, cl, br and I;
R 4 selected from H, F, cl, br;
A 1 is CR (CR) 5 Or N;
A 5 is CR (CR) 9 ；
R 5 Selected from H, F, cl, CN and (C) 1 -C 6 ) An alkyl group;
R 9 selected from H and F;
R 13 is Cl or F;
R 15 is H.
In one embodiment of the invention and/or embodiments thereof, the parasite infestation is an ectoparasite infestation.
In one embodiment of the invention and/or embodiments thereof, the parasite infestation is a tick infestation or a flea infestation, preferably a tick infestation.
In one embodiment of the invention and/or embodiments thereof, the parasite is a single host tick.
In one embodiment of the invention and/or embodiments thereof, the parasite is a rhipicephalus minitans.
In one embodiment of the invention and/or embodiments thereof, the parasite is a multi-host tick.
In one embodiment of the invention and/or embodiments thereof, the parasite is a mite parasite.
In one embodiment of the invention and/or embodiments thereof, the animal is a warm-blooded animal, especially a mammal.
In one embodiment of the invention and/or embodiments thereof, the animal is a domestic animal, in particular a bovine animal, in particular a ruminant animal, in particular a domestic bovine animal.
In one embodiment of the invention and/or embodiments thereof, the animal is a fish and the parasite infestation is sea lice infestation.
In one embodiment of the invention and/or embodiments thereof, the animal is a companion animal, particularly a canine or a feline, particularly a dog or cat.
In one embodiment, the compounds of the invention are effective in treating existing and providing protection
In one embodiment of the invention and/or embodiments thereof, the existing parasite infestations of animals are treated or controlled.
Suitably, the compounds of the present invention and/or embodiments thereof are used in methods wherein the parasite infestation is a tick infestation or a flea infestation. The compounds are suitable for use in tick infestations.
The compounds of the invention and/or embodiments thereof are suitable for use against parasites, wherein the parasite is a single host tick or a multi-host tick. Suitably the compounds of the invention are useful against rhipicephalus minutissima.
In a suitable use or method of the invention and/or any embodiment thereof, the animal is a warm-blooded animal, such as a mammal. However, the compounds of the invention and/or embodiments thereof are also active in livestock animals, such as ruminants, bovine animals or cattle. It has also been found that the compounds of the invention and/or embodiments thereof have activity in fish against sea lice infestation. Moreover, the compounds of the present invention and/or embodiments thereof are found to be active in companion animals, such as canine or feline, particularly dogs or cats.
Salts, solvates, N-solvates and prodrugs
A salt of a compound of formula (I) or another compound may be advantageous due to one or more physical properties of the salt, such as pharmaceutical stability at different temperatures, humidity, crystallinity and/or desired solubility in water, oil or other solvents. In some cases, salts may be used as an aid in the isolation, purification and/or isolation of compounds. Acid and base salts can generally be formed, for example, by mixing the compound with an acid or base, respectively, using various methods known in the art. Insofar as salts of the compounds are intended to be administered in vivo (i.e., to animals) to obtain therapeutic benefits, the salts are pharmaceutically acceptable.
Salts may also be advantageous in the synthesis of compounds according to the invention and/or embodiments thereof. For example, certain intermediates may be advantageously used in the preparation of compounds according to the invention and/or embodiments thereof in the form of salts thereof.
Generally, the acid addition salts can be prepared by reacting the free base compound with about stoichiometric amounts of an inorganic or organic acid. Non-limiting examples of mineral acids that are generally suitable for use in preparing the (pharmaceutically acceptable) salts include hydrochloric acid, hydrobromic acid, hydroiodic acid, nitric acid, carbonic acid, sulfuric acid, and phosphoric acid. Non-limiting examples of organic acids generally suitable for use in preparing the (pharmaceutically acceptable) salts generally include, for example, organic acids such as aliphatic acids, cycloaliphatic acids, aromatic acids, araliphatic acids, heterocyclic acids, carboxylic acid groups, and sulfonic acids. Specific examples of generally suitable organic acids include cholic acid, sorbic acid, lauric acid, acetic acid, trifluoroacetic acid, formic acid, propionic acid, succinic acid, glycolic acid, gluconic acid, digluconic acid, lactic acid, malic acid, tartaric acid, citric acid, ascorbic acid, glucuronic acid, maleic acid, fumaric acid, pyruvic acid, aspartic acid, glutamic acid, aryl carboxylic acids (e.g., benzoic acid), anthranilic acid, methanesulfonic acid, stearic acid, salicylic acid, p-hydroxybenzoic acid, phenylacetic acid, mandelic acid, methylenepamoic acid, alkylsulfonic acid (e.g., ethanesulfonic acid), arylsulfonic acid (e.g., benzenesulfonic acid), pantothenic acid, 2-hydroxyethanesulfonic acid, sulfanilic acid, cyclohexylsulfamic acid, β -hydroxybutyric acid, mucic acid, galacturonic acid, adipic acid, alginic acid, butyric acid, camphoric acid, cyclopentanic acid, dodecylsulfonic acid (dodecylspline), glucoheptoic acid, glycerophosphate, heptanoic acid, caproic acid, nicotinic acid, 2-naphthalenesulfonic acid, oxalic acid, pamoic acid, pectic acid, 3-phenylpropionic acid, picric acid, pivalic acid, tosic acid, and undecanoic acid. For example, in some such embodiments, the salt comprises trifluoroacetate, mesylate, or tosylate. In other embodiments, the salt comprises the hydrochloride salt.
By way of non-limiting example, the amine functionality may form a salt with hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, acetic acid, benzoic acid, citric acid, malonic acid, salicylic acid, malic acid, fumaric acid, oxalic acid, succinic acid, tartaric acid, lactic acid, gluconic acid, ascorbic acid, maleic acid, aspartic acid, benzenesulfonic acid, methanesulfonic acid, ethanesulfonic acid, hydroxy-methanesulfonic acid, and hydroxyethanesulfonic acid. Further, by way of non-limiting example, the acid functionality may form salts, including those derived from alkali or alkaline earth metals and those derived from ammonia or amines. Examples of preferred cations include sodium, potassium and magnesium.
In general, base addition salts can be prepared by reacting the free acid compound with about stoichiometric amounts of an inorganic or organic base. Examples of the base addition salt may include, for example, metal salts, organic salts. For example, metal salts include alkali metal (group Ia) salts, alkaline earth metal (group IIa) salts, and other physiologically acceptable metal salts. Such salts may be prepared from aluminum, calcium, lithium, magnesium, potassium, sodium, zinc. For example, the free acid compound may be mixed with sodium hydroxide to form such a base addition salt. Organic salts can be prepared from amines such as trimethylamine, diethylamine, N' -dibenzylethylenediamine, chloroprocaine, ethanolamine, diethanolamine, ethylenediamine, meglumine (N-methylglucamine) and procaine. Basic nitrogen-containing groups can be quaternized with agents such as C1-C6-alkyl halides (e.g., methyl, ethyl, propyl, and butyl chlorides, bromides, and iodides), dialkyl sulfates (e.g., dimethyl, diethyl, dibutyl, and diamyl sulfates), long chain halides (e.g., decyl, dodecyl, myristyl, and stearyl chlorides, bromides, and iodides), aralkyl halides (e.g., benzyl and phenethyl bromides).
The compounds of formula (I) may be formulated into stable complexes with solvents such that the complex remains intact after the non-complexed solvents are removed. These complexes are often referred to as "solvates". However, the formation of stable hydrates with water as solvent is particularly desirable.
The compound of formula (I) or a solvate of another compound may be formed by aggregation of the compound with a solvent molecule such as water, an alcohol (e.g. ethanol), an aromatic solvent (e.g. toluene), an ether, a halogenated organic solvent (e.g. dichloromethane), preferably in a defined weight ratio.
The compounds of formula (I) containing acid functionality can be made into ester derivatives. These ester derivatives can then be applied in the same manner as the compounds disclosed herein are applied.
The compounds of formula (I) may be prepared as various crystalline polymorphs. Polymorphism is important in the development of veterinary products because different crystal polymorphs or structures of the same molecule may have distinct physical and biological properties.
The N-oxide of the compound of formula (I) or another compound may be formed by oxidizing the N atom in an amine or N-heterocycle with an oxidizing agent such as hydrogen peroxide, a peracid, or an inorganic oxidizing agent such as potassium peroxymonosulfate (oxone).
The invention also includes prodrug derivatives of the compounds of formula (I). The term prodrug refers to a compound that is converted to the parent compound of formula (I). Transformation generally occurs in vivo. By in vivo is meant that, for example, in the case of treatment of parasite infestations, such transformation may occur in the host organism and/or parasite. Various forms of prodrugs are well known in the art. For example, if the group of formula (I) represents pyridine, it is possible to form pyridinium salts, such as acyloxyalkylpyridinium salts, which may offer the advantage of higher solubility for parenteral dosage forms, as described in S.K. Davidsen et al, J.of Med.chem.37 4423-4429 (1994).
The compounds of formula (I) may be prepared using different isotopes. Of particular importance is the use of 2 H (also known as deuterium) or 3 H (also known as tritium) is substituted 1 Division of HAnd (5) a seed. The molecules of formula I may be prepared from different radionuclides. It is particularly important to have 14 Molecules of C (also known as radioactive carbon). Containing deuterium, tritium or 14 The molecules of formula (I) of C can be used in biological studies, allowing for tracking in chemical, physiological processes and half-life studies, as well as MoA studies.
Isomers of
The compounds of formula (I) may exist in different geometric or optical isomers or tautomeric forms. One or more chiral centers may be present, in which case the compounds of formula (I) may be present as pure enantiomers, mixtures of enantiomers, pure diastereomers or mixtures of diastereomers. One skilled in the art will appreciate that one stereoisomer may be more active than the other stereoisomers. The individual stereoisomers may be obtained by known selective synthetic methods, by conventional synthetic methods using resolved starting materials or by conventional resolution methods. Double bonds may be present in the molecule, in which case the compounds of the formula (I) may be present as single geometric isomers (cis or trans, E or Z) or as mixtures of geometric isomers (cis and trans, E and Z). Tautomeric centers may exist. The present disclosure encompasses all such isomers, tautomers, and mixtures thereof in all ratios.
In some embodiments, such compounds may have two or more isomers, such as optical isomers or conformational isomers. For example, the compound may be at-CXR 3 ＝CR 1 R 2 The double bond has the (E) or (Z) configuration, as in the alkenyl or alkynyl substituents of the ring formed by A1 to A5. In some preferred embodiments, such compounds have the (E) configuration, in other embodiments, the compounds have the (Z) configuration. In a preferred embodiment, the compound has the (E) configuration.
Unless otherwise indicated, a structure of a compound that does not indicate a particular conformation is intended to encompass all possible conformational isomers of the compound, as well as less than all possible conformational isomers. There are four isomers of compounds with two chiral centers: RR-, SS-, RS-, and SR-isomers. These compounds can exist in various forms, i.e. as pure RR or SS or RS or SR isomers or as mixtures, hereinafter referred to as "enantiomer pairs" of RR/SS or RS/SR. The compounds may also exist as a racemic mixture of all four isomers (rr+ss+rs+sr) or enantiomer pairs (RR/SS) or (RS/SR). Isomers (RR) and (SS) are mirror images of each other and are thus enantiomers, which have the same chemical properties and melting point. (RS) and (SR) are similarly enantiomer pairs. However, the mirror images of (RR) and (SS) are not superimposed on (RS) and (SR). This relationship is called diastereoisomerism, and (RR) is the diastereomer of (RS).
Although structurally identical, isomers may have different roles in biological systems: one isomer may have a particular therapeutic activity, while another isomer may not have a therapeutic activity or may have a completely different form of biological activity.
In the compounds of the invention, cyclopropane contains 2 chiral centers, one bonded to the phenyl group and the other bonded to the carboxamide group.
It has now surprisingly been found that by administering pure or substantially pure RR-isomers of the compounds according to the invention and embodiments described herein, pharmaceutically acceptable salts thereof, parameters such as efficacy can be greatly improved, while side effects can be substantially avoided. Thus, applicants have discovered that by administering a therapeutically effective amount of a pure or substantially pure RR-isomer of a compound according to any of the embodiments and embodiments described herein, a pharmaceutically acceptable salt thereof.
The terms "pure RR-compounds according to the invention and embodiments described in any embodiment", "pure RR-isomers according to the invention and embodiments described in any embodiment", etc., refer to compounds according to the invention and embodiments described in any embodiment having an optical purity of 98 wt.% or more of RR-compounds according to the invention and embodiments described in any embodiment, which means that the RR-isomers are present in a concentration of 98 wt.% or more, whereas the total concentration (i.e. the sum) of the corresponding RS-, SR-, SS-isomers is 2 wt.% or less based on the total amount of compounds according to the invention and embodiments described in any embodiment.
The terms "substantially pure RR-compounds according to the invention and embodiments described in any embodiment", "substantially pure RR-isomers of compounds according to the invention and embodiments described in any embodiment", etc., refer to an optical purity of the substantially pure RR-compounds according to the invention and embodiments described in any embodiment of 80 wt.% or more, which means a concentration of 80 wt.% or more and a sum of 20 wt.% or less of the corresponding RS-, SR-and SS-isomers of the RR-compounds according to the invention and embodiments described in any embodiment, based on the total amount of compounds according to the invention and embodiments described in any embodiment. In a more preferred embodiment, the "substantially pure RR-compound according to the invention and embodiments described in any embodiment" contains 90% by weight or more of the sum of the RS and SR and SS-isomers of the RR-compound according to the invention and embodiments described in any embodiment and 10% by weight or less of the compound according to the invention and embodiments described in any embodiment.
In a suitable embodiment, the compounds of formula (I), formamide and phenyl (which is bonded to cyclopropane) are in the R, R configuration. This embodiment may be combined with R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 And R is 15 Used in combination with any other embodiment of (c).
In one embodiment of the invention and/or embodiments thereof, the parasite infestation is an ectoparasite infestation.
In one embodiment of the invention and/or embodiments thereof, the parasite infestation is a tick infestation or a flea infestation, preferably a tick infestation.
In one embodiment of the invention and/or embodiments thereof, the parasite is a single host tick.
In one embodiment of the invention and/or embodiments thereof, the parasite is a rhipicephalus minitans.
In one embodiment of the invention and/or embodiments thereof, the parasite is a multi-host tick.
In one embodiment of the invention and/or embodiments thereof, the parasite is a mite parasite.
In one embodiment of the invention and/or embodiments thereof, the animal is a warm-blooded animal, especially a mammal.
In one embodiment of the invention and/or embodiments thereof, the animal is a domestic animal, in particular a bovine animal, in particular a ruminant animal, in particular a domestic bovine animal.
In one embodiment of the invention and/or embodiments thereof, the animal is a fish and the parasite infestation is sea lice infestation.
In one embodiment of the invention and/or embodiments thereof, the animal is a companion animal, particularly a canine or a feline, particularly a dog or cat.
In one embodiment of the invention and/or embodiments thereof, the animal is protected from parasite infestations.
In one embodiment of the invention and/or embodiments thereof, the existing parasite infestations of animals are treated or controlled.
In one embodiment of the invention and/or embodiments thereof, the method comprises administering the compound to the animal weekly, biweekly, monthly, every 6 weeks, every 2 months, or every 3 months.
In one embodiment of the invention and/or embodiments thereof, parasite infestation of the animal is prevented for at least one week.
The invention also relates to a veterinary composition comprising an effective amount of a compound of formula (I) as defined in any of the embodiments described herein and an inert carrier or formulation adjuvant. The composition is suitable for use in the treatment and control of animal parasite infestations as described herein.
In one embodiment of the invention and/or embodiments thereof, the veterinary composition is a topical composition.
In one embodiment of the application and/or embodiments thereof, the veterinary composition is an oral composition.
In one embodiment of the application and/or embodiments thereof, the veterinary composition is an injectable composition.
The method according to the application
The compounds of the application and/or embodiments thereof described herein, as well as pharmaceutically acceptable solvates, N-oxides, salts and prodrugs thereof, as applicable, are generally useful as medicaments for animals, wherein one or more, preferably one, of the compounds according to the application and/or embodiments thereof is administered to an animal for the treatment or control of parasitic infestations.
The compounds of the application and any of their embodiments are useful in methods of treating or controlling parasite infestations of animals.
Another aspect of the application is a composition for treating and/or protecting animals from parasites, comprising such a compound and a veterinary or pharmaceutically acceptable excipient.
"infestations" refer to a large number of parasites at risk of harm or injury to animals. Such presence may be in the environment, on the skin or coat of an animal or in the blood, organs or tissues of an animal, etc.
The term "(parasitic) infestation" includes conditions associated with or caused by one or more (parasitic) pathogens; such disorders include clinical disorders (parasitic diseases) and subclinical disorders.
Thus, the term "treatment of parasitic infestation" includes treatment of parasitic diseases and treatment of subclinical disorders. Treatment of parasite infestations generally means that the parasite burden of the animal is suppressed below the level at which economic losses occur. By "treating (parasitic) infestation" is meant partially or completely inhibiting the occurrence of (parasitic) infestation in animals susceptible to (parasitic) infestation, reducing or completely eliminating the symptoms of infestation in animals with infestation, and/or partially or completely curing the infestation in animals with infestation. This can be achieved by reducing or eliminating the number of pathogens (e.g., parasites in or on an animal).
Subclinical disorders are generally disorders that do not directly result in parasites invading the animal's clinical symptoms, but result in economic losses. Such economic losses may be, for example, by growth inhibition of young animals, reduced feed efficiency, reduced weight gain in meat producing animals, reduced milk production in ruminants or reduced wool production in sheep.
The term "treatment" and like terms, as used herein, "treatment" or "treatment" refers to the administration of an effective amount of at least one of the compounds for use in the present invention to an animal having infestation (of severity or high or low) by parasites of one or more species.
The term "control" as used herein with respect to the field of animal health means that the compound acts by reducing the occurrence of the parasite to harmless levels in or on animals that have been infested by or are at risk of being infested by the parasite. Control of parasites is the medical care given to animals infested by or at risk of being infested by such parasites. This means that the number of parasites in and/or on the animal body is reduced or eliminated and/or the occurrence of parasite infestations in and/or on the animal body is partially or completely inhibited. This may be accomplished by, for example, killing, repelling, expelling, disabling, preventing, eliminating, alleviating, or minimizing parasite infestation.
Thus, controlling means improving or eliminating the current parasite infestation and/or preventing or reducing future infestation or re-infestation of the animal or animal population.
In the context of the present invention, the term "control" includes in particular the prophylactic treatment of animals against parasite infestations/infections. Prophylactic treatment of an animal against a disease or disorder refers to treatment prior to exposure or exposure of the animal to a pathogenic agent of the disease or disorder (e.g., parasite, particularly the stage of infection by the parasite), or after such exposure/exposure but prior to the occurrence of a detrimental disorder (e.g., loss of production in a subclinical disorder (e.g., loss of production in livestock) (e.g., reduction in milk production, reduction in weight gain, loss of wool), prior to the occurrence of clinical symptoms, or early stages of disease progression).
More specifically, "controlling" as used herein means that the compound kills the parasite, retards its growth, or inhibits its reproduction.
The effect may be, for example, ovicidal, larvicidal, and/or imago-cidal, or a combination thereof. The effect may be directly manifested, i.e. killing the parasite immediately or after a period of time (e.g. upon molting), or by destroying its eggs, or indirectly manifested (e.g. reducing the number of eggs laid and/or the hatching rate).
Thus, controlling means improving or eliminating the current parasite infestation and/or preventing or reducing future infestation or re-infestation of the animal or animal population.
Control of parasites may also help prevent the parasite from spreading infectious agents to animals (vector control). The compounds of formula (I) are also useful for vehicle control. In the context of the present invention, vectors, in particular arthropods, in particular insects or arachnids or crustaceans, are capable of transmitting pathogens, such as viruses, worms, unicellular organisms and bacteria, from a reservoir (plant, animal, human, etc.) to a host animal.
Examples of vectors and diseases or pathogens transmitted thereby are ticks that transmit tick-borne encephalitis, Q-fever (Coxiella berkovich), borrelia disease (Lyme disease caused by borrelia, e.g., boehmeria, babesia disease (or Piropriosis caused by Babesia), and Rickettsia disease (e.g., chikukikura zebra fever).
The term "parasitic diseases" relates to pathological conditions and diseases of clinical manifestations associated with or directly caused by the infestation of one or more parasites, such as anemia and flea allergic dermatitis. It also includes pathological conditions or diseases associated with or caused by one or more vector-transmitted pathogens, such as lyme disease, ehrlichiosis (particularly canine ehrlichiosis) and vector tick-induced fever of the hikura.
"treating a parasitic disease" refers to partially or completely inhibiting the development of a parasitic disease in an animal, alleviating or completely eliminating symptoms of a parasitic disease in an animal, and/or partially or completely curing a parasitic disease in an animal.
In general, parasite infestation, including parasites, is controlled by the administration of an effective amount of one or more, preferably one, of the compounds of the present invention.
The term "preventing", "preventing" or "prophylactic treatment" is intended to mean the administration of a compound of the invention to an animal prior to the occurrence of a parasitic infection or infestation, to prevent the occurrence of such infection or infestation. The administration of the compound at recommended regular intervals is effective to prevent neoparasite infestation or infection in the animal by killing the neoparasite of the challenged animal prior to its reproduction to form the infestation or infection.
Furthermore, in connection with an animal population, the term "prophylactic treatment" refers to treatment of all members of the animal population to limit or avoid its transmission and contamination to other members of the animal population, even after a disease or disorder (e.g., parasite infestation) is detected in only some animals.
The compounds according to the invention act on animal parasites, in particular ectoparasites and/or endoparasites. Ectoparasites are parasites that live on the outer surface of host animals. Endoparasites are parasites that live in the internal organs or tissues of their hosts.
Ectoparasites are parasites that live on the outer surface of host animals.
Endoparasites are parasites that live in the internal organs or tissues of their hosts.
Ectoparasites are usually and preferably arthropods, in particular insects, such as flies (biting and licking), parasitic fly larvae, lice, fleas, etc.; or mites such as ticks, e.g., hard or soft ticks, or mites such as itch mites, scabies or demodex mites, etc. Important ectoparasites of fish are crustaceans parasites, for example aquatic ectoparasites such as sea lice.
Ectoparasites tend to irritate animals and can also cause clinical diseases and adverse sub-clinical conditions either alone or through pathogens transmitted by the carrier medium.
In particular, ticks are parasitic on wild animals and domestic animals, and are known to cause the transmission of pathogens, including bacteria, viruses and protozoan parasites. Ticks also release toxins, which cause inflammation or paralysis in the host. Occasionally, these toxins are lethal to the host.
On the other hand, such ectoparasites severely affect the productivity of animal husbandry by reducing weight gain or milk production, leading to poor quality of hides, wool and meat, and in some cases, death. Ectoparasites are also part of the cause of pathogen transmission as a vehicle and cause discomfort to livestock and companion animals, thereby affecting animal health.
In one embodiment of the invention and/or embodiments thereof, the ectoparasite is selected from the group consisting of fly, parasitic fly larvae, lice, fleas, ticks, mites and sea lice.
In one embodiment of the invention and/or embodiments thereof, the ectoparasite is an insect or mite. Suitably, the insect is not a mosquito. Suitably, the ectoparasite is a mite.
Suitably, the mite ectoparasite is a hard tick, a soft tick or a mite.
Suitably, the ectoparasite is a sea lice.
For example, parasites common in domestic animals (e.g., cattle) are ticks of the genus rhipicephalus, especially those of the species rhipicephalus micropus (tropical cattle ticks), rhipicephalus depigmentus, and rhipicephalus circulans. Ticks such as rhipicephalus (original rhipicephalus) are difficult to control.
Such tick species are considered single host ticks and live in an animal in immature and adult stages, after which females satiate (engorge) and leave the host to spawn in the environment. The tick life cycle is about three to four weeks. In addition to cattle, rhipicephalus microplus can infest buffalo, horses, donkeys, goats, sheep, deer, pigs and dogs.
Veterinary related ectoparasites (typically insect and mite pests) of warm-blooded animals include:
insects. These are parasitic stages of flies, fleas, lice, bed bugs, including, for example, transitional biptera larvae (diptera larve) in cattle, such as, for example, fly, peproma in horses, yellow fly in rodents; flies which bite humans, for example, adult flies which suck blood (for example, horn flies (Horseradish), horse flies (Tabanus), stings flies (stable stings flies), black flies (gnats), deer flies (hermetia), lice flies (sheep lice flies), tsetse flies (glossaria), parasitic fly larvae, for example, skin flies (caprine flies and Huang Ying), blowflies (green flies), spiny fly larvae (trichina, cow flies (dermatophagoides) and trichina, suitably mosquitoes, which are not mosquitoes.
Lice. These include, for example, the species luffa, such as the species bird luffa and cattle luffa; and sucking lice such as genus Xuezus, genus Trichinella and genus Pediculus.
Fleas. These include, for example, chlamydia, such as, for example, dog fleas (Chlamydia canis) and cat fleas (Chlamydia felis); the genus daphnia, such as the species Oriental murine fleas (Porphyra tenera); fleas (Pulex spp.), such as, for example, human fleas (Pulex iritans); hedgehog fleas (Archaeopsylla erinacei); and avian fleas (chicken fleas).
Stinkbugs. These include, for example, the family of bugs or ordinary bugs (temperate zone bugs); and the subfamily echinococci, such as triatomid insects (also known as hunter bugs) (e.g., echinocgus lucorum and echinocgus).
Mites. These include:
i. the order of the medium-valve, such as mesostingmatids, includes chicken mites (dermatophagoides pteronyssinus).
Lie. there are no valve sub-orders, such as itch mites (itch mites) or scabies, including scabies (e.g., scabies); and mange mites, which include the family of itch mites (e.g., itch mites of cow leather and sheep).
Iii. front valve subgenera, such as chiggers, which include the families of chiggery (e.g., north America chiggers, armillaria tsutsugamushi).
Iv. Demodex.
Ticks. These include, for example, soft ticks, such as the cryptorhizus family (e.g., sharp and dull ticks); and hard ticks such as hard ticks of the family hard ticks (e.g., rhizus, sanguinea, leather reticulata, leather variant ticks, chlorpyrifos americanus, and rhizus (bovine).
In one embodiment, the ectoparasites are ticks of the genus leather, hard ticks, chlorpyrifos, sanguinea, phophagous, especially rhipicephalus (bovine), especially those of the species bovine ticks.
The rhipicephalus minutissimus, rhipicephalus depigmentus and rhipicephalus circulans are single-host ticks, meaning that all three phases of the life cycle live on the same animal.
Multi-host ticks land after ingestion of the animal at each stage and reattach to another host after molting. The host species may vary between stages. Representative of multi-host ticks are, for example, chlorpyrifos, holocycle hard ticks, i.e., paralyzed ticks: the feed comprises long angle blood ticks, additional rhipicephalus and Hibernation chlorpyrifos, bai Wenge ticks, blackia maculata, amblyomma andersoni, rigid ticks of castor bean and Aleuropaea marginalis.
The main reasons for tick control in livestock are protection of the host from irritation and loss of production, formation of lesions that can become secondary infections, hide and breast damage, poisoning, paralysis, and most importantly, avoidance of infection by a wide variety of pathogens.
Ectoparasite infestations of animals treated with the compounds include, but are not limited to, fleas, ticks, mites, flies, lice, blowflies, and co-infestations with more than one species.
In a preferred embodiment, the compounds of the invention are used for the treatment or protection of animals against parasitic infections and infestations of companion animals, especially dogs and cats, especially control of fleas and/or ticks or mites, especially Chlamydia felis, rhizocephalus hemsleyanus, hard castor ticks, aleurites variegatus, america, hard shoulder ticks, aleurites, gloiopelus and/or hard full loop ticks.
In another preferred embodiment, the compounds of the invention are useful for treating or protecting parasitic infections and infestations of dogs and cats, particularly for controlling infestation by Demodex mites.
The compounds are useful for the treatment of tick infestations (Aleurites anilox, aleurites hexagonus, aleurites castor and Aleurites sanguinea) in dogs and/or cats. The compounds have sustained tick killing activity immediately and for at least 5 weeks. For the treatment of flea infestations (Chlamydia felis and Chlamydia canis), the compounds have sustained flea killing activity for immediate and at least 5 weeks against the new infestations. The compounds are useful as part of a therapeutic strategy for controlling Flea Allergic Dermatitis (FAD). The compound can be used for treating scabies (scabies). The compounds are useful for the treatment of ear mite infestations (Dermatophagoides pteronyssinus). The compounds are useful for the treatment of Demodex disease (Demodex canine).
The compounds are useful for killing adult fleas and for the treatment and prevention of flea infestations (Chlamydia felis) and for the treatment and control of black leg ticks (hard shoulder ticks), american dog ticks (leather variation ticks), solitary ticks (Americana) and brown dog ticks (Rhizocephalus glabra) infestations in companion animals, dogs and/or cats.
In another preferred embodiment, the compounds of the invention are used for the treatment or protection of domestic animals, in particular ruminants such as cattle or sheep, against parasitic infections and infestations. The compounds are particularly effective against rhipicephalus (microcattle), hornfly (horn fly), stable flies (stings fly) and myiasis such as lucilia sericata (European green fly), aerugo (Narcissus trichina or Australian sheep green fly called green maggot disease in Australia, new Zealand and south Africa), chrysomya rubra ((Chrysomya rufifacies)) (Mao Juying), chrysomya varipes (microcephas), calliphora stygia (Common brown blowfly), mantis fly (lesser brown blowfly (eastern)), calliphora novicia (lesser brown blowfly (western)).
The sucking lice engulf the host's blood food and are more important in transmitting pathogens. The feather or biting lice ingest coat and skin from the host, sometimes sucking blood; important lice parasites are cattle lice (cattle feather lice), long nose lice (Niu Eshi), small blue lice (buffalo coat lice (Solenopotes capillatus)), short nose lice (cattle blood lice), tail lice (Haematopinus quadripertusus) and sheep and goat lice (sheep lice).
In one embodiment, the compounds of the invention are useful for the treatment or protection against parasitic infections and infestations by mange mites such as itch mites of cow, scab and sheep.
The above list is not exhaustive and other ectoparasites are known in the art to be harmful to animals, especially domestic animals, especially ruminants, more especially cattle or sheep. These include, for example, transitional bipteran larvae.
Surprisingly, it has been found that the compounds or compositions of the present invention are effective in controlling one or more of these parasites.
An important ectoparasite for cold-blood animals such as fish is sea lice. Sea lice are ectoparasites that feed on the mucous membranes, epidermal tissues and blood of the host marine fish, especially salmon. Sea lice belong to the subclass of the copepods. The term "sea lice" as used herein refers to all members of the family fish lice; it includes, inter alia, salmon scab lice (Lepeophtheirus salmonis), caligus rogercresseyi, c.elongatus and Caligus clemensi, or humanoid fish lice (leranthridae); which includes Lernanthropus kroyeri.
Sea lice can cause serious injury to host fish, in particular they can cause severe fin damage, skin erosion, bleeding and open wounds. In addition, sea lice can cause chronic stress reactions in fish, which in turn predisposes the fish to other diseases. Sea lice infestation is a major problem in fish farming and can lead to significant economic losses.
The term "endoparasites" includes in particular helminths, such as cestodes, nematodes or trematodes, and protozoa, such as coccidia. Endoparasites include nematode pests that typically infect animals, and include their eggs, larvae, and adult stages. Such pests include worms (roundworms, hookworms, tapeworms, heartworms) and are of great commercial interest because they cause serious diseases in animals.
In some embodiments of the invention, particularly where the compound is combined with another active ingredient, the composition may also be used to treat endoparasites, such as those caused by one or more worms selected from a) cestodes, such as the genus anoplophala spp; cestode (Dipylidium spp.); the genus schizocephalum (Diphyllobothrium spp); echinococcus (echinococcus spp.); a tenia (Moniezia spp.); taenia (Taenia spp.); b) Flukes, for example, the genus dichocoelium (spp.); schistosoma (Fasciola spp.); homofasciola (paramphism spp.); the genus fasciola (Schistosoma spp.); or c) nematodes, such as ancystoma spp; anecator spp; avian roundworm (ascaria spp.); ascaria (Ascaris spp.); brucella (Brugia spp.); the genus rennet (Bunostomum spp.); capillaria spp; xia Bai nematode (Chabertia spp.); the genus cooper (cooper spp.); c. Calico (Cyathostomum spp.); the genus cyclonematoda (cylicomyces spp.); the genus meloidogyne (cylicodontophosphorus spp); meloidogyne (cylicosphagnus spp.); prayer nematode (cratertostom spp.); the genus reticulata (Dictyocailus spp.); bivalve nematode (Dipetalonema spp.); dirofilaria (Dirofilaria spp.); dragon's (Dracocuus spp.); pinworm (enterobias spp.); filarial (filariales spp.); mollusch genus (Habronema spp.); haemonchus spp; the genus heterodera (heteroaia spp.); the genus strongylos (hyotrungmus spp.); metastrongylus spp; meullerius spp; aphelenchus (neccator spp.); the genus Nematodirus (Nematodirus spp.); round-the-sun nematode genus plate (nippostungylus spp.); tuberous nematodes (oemophagogostomum spp.); onchocercias (Onchocerca spp.); ostertagia spp); the genus meloidogyne (Oxyuris spp.); ascaria (paraascaris spp.); reniform (stephanus spp.); round nematode (Strongylus spp.); pythonema (Syngamus spp.); toxoplasma (Toxocara spp.); round-like wireworm (Strongyloides spp.); the genus caenorhabditis (teladorsigia spp.); toxoplasmosis (tophana spp.); trichinella spp; dinoflagellate (Trichuris spp.); trichostrongylosis (trichostrongylos spp.); triotonophorus spp; hookworm (Uncinaria spp.); and/or evodia (Wuchereria spp.).
In a suitable use of the invention and/or any embodiment thereof, the animal is protected from parasite infestations. In one embodiment, the existing parasite infestation of the animal is treated or controlled. In another embodiment, the animal is treated or controlled for an existing parasite infestation and protected from parasite infestation
Another embodiment is a method of protecting an animal at risk of infestation by parasites comprising administering to the animal an effective amount of at least one compound of the invention and/or embodiments thereof using a single administration.
In one embodiment, the invention provides a composition comprising an effective amount of a compound of the invention and/or embodiments thereof, when used to treat and/or protect an animal from parasitic infestation, wherein the composition is administered to an animal diagnosed or suspected of being infested by a parasite. In one embodiment, the composition is administered to an animal at risk of infestation by parasites to protect it from parasites.
In a suitable use of the invention and/or any embodiment thereof, the method comprises administering a compound of the invention and/or embodiments thereof to an animal weekly, biweekly, monthly, 6 weekly, 2 months, 3 months, 4 months, 6 months or 9 months.
Surprisingly, a variety of compounds of the present invention and/or embodiments thereof are also capable of protecting a variety of animal species from parasite infestations.
In one embodiment of the invention and/or embodiments thereof, the animal is protected from parasite infestations.
In one embodiment of the invention and/or embodiments thereof, ruminants, preferably bovine animals, are protected, preferably from ticks. In one embodiment, the tick is a single host tick. In another embodiment, the tick is a multi-host tick.
In one embodiment of the invention and/or embodiments thereof, companion animals, preferably dogs or cats, are protected, preferably from ticks and/or fleas, preferably ticks and fleas.
In one embodiment of the invention and/or embodiments thereof, the method comprises administering the compound to the animal weekly, biweekly, monthly, 6 weekly, 2 months, 3 months, 6 months, or 9 months.
Another aspect of the invention is a composition for treating and/or protecting animals from parasites comprising a compound of the invention and/or embodiments thereof and a veterinarily or pharmaceutically acceptable excipient.
"protection or protection" refers to preventing new infestations or re-infestations of animals or groups or herds by killing adult parasites and any developmental/juvenile stages that can infest the host, or by killing or inhibiting parasites or preventing the production of parasite offspring, e.g., reducing the number of eggs laid and/or hatchability, when the parasites infest animals treated with the compound.
For use in the present invention, "preventing re-infestations" includes the situation where an animal is exposed to a new infestation by a parasite, as it either lives in the presence of a living parasite or is in intimate contact with the animal (or human) infested by the parasite, thus having a "risk of being infested.
Re-infestations are secondary or subsequent infestations of parasites. This means that at some point animals that are (substantially) free from parasite infestations are (again) infested with parasites from external sources. The compounds or compositions of the present invention kill these newly emerging parasites before they can infest the animal, or limit irritation and damage to the animal by allowing a non-significant number of parasites to reduce the number of parasites.
"protective period" refers to the time, expressed as days or weeks after treatment, that a veterinary test article prevents re-infestation by ectoparasites in an animal host. Sometimes referred to as the preventive or sustained efficacy period (WAAVP guidelines, 2006)
For example, the protective period may be useful when the treated animal is contacted with an untreated animal, or when the treated animal and untreated animal are mixed.
The frequency of administration depends on a variety of factors and may be a single dose administered once a day, or may be once a week, once a month, once every two months, three months, four months or six months, or once nine months, or once a year, depending on the period of protection. In some embodiments, the frequency of administration may be, for example, weekly, biweekly, monthly, bi-monthly, 3-monthly, 4-monthly, 5-monthly, 6-monthly, 9-monthly, or 12-monthly, or an equivalent frequency of administration expressed in days or weeks approaching the frequency.
In one embodiment, the compositions comprising the compounds of the invention and/or embodiments thereof exhibit sustained efficacy and provide protection against parasites in animals, particularly domestic animals, for at least one month.
In another embodiment, the compounds of the invention and/or embodiments thereof exhibit a very long lasting efficacy against ticks of at least 50% for at least 1 month, at least 2 months, at least 3 months, or at least 4 months or at least 5 months, at least 6 months, or 9 months.
In another embodiment, the compounds of the invention and/or embodiments thereof exhibit a very sustained efficacy against ticks of at least 70% for at least 1 month, at least 2 months, at least 3 months, or at least 4 months or at least 5 months, at least 6 months, or 9 months.
In another embodiment, the compounds of the invention and/or embodiments thereof exhibit a very long lasting efficacy against parasites (e.g., ticks) of at least 90% for at least 1 month, at least 2 months, at least 3 months, or at least 4 months, or at least 5 months, at least 6 months, or 9 months.
In another embodiment, the compounds of the present invention and/or embodiments thereof exhibit a very long lasting efficacy against parasites (e.g., fleas) of at least 90% for at least 1 month, at least 2 months, at least 3 months, or at least 4 months, or at least 5 months, at least 6 months, or 9 months.
In one embodiment of the invention and/or embodiments thereof, parasite infestation of the animal is prevented for at least one week, preferably at least 10 days, at least two weeks, 3 weeks, 4 weeks, 6 weeks, 8 weeks, 10 weeks, 12 weeks, 16 weeks, 26 weeks or 36 weeks.
In one embodiment of the invention and/or embodiments thereof, parasite infestation of the animal is prevented or controlled for at least two weeks, 3 weeks, 4 weeks, 6 weeks, 8 weeks, 10 weeks, 12 weeks, 16 weeks, 26 weeks or 36 weeks.
In one embodiment of the invention and/or embodiments thereof, parasite infestation of the animal is prevented or controlled for at least one month, two months, three months, six months or nine months.
A single administration of a compound of the invention and/or embodiments thereof is generally sufficient to protect an animal from parasites. While such a single dose is generally preferred, it is contemplated that multiple doses may be used for a single treatment.
Another embodiment is a method of treating an animal that has been diagnosed or suspected of being infested by a parasite comprising administering to the animal an effective amount of at least one compound of the invention and/or embodiments thereof using a single administration.
In one embodiment of the invention and/or embodiments thereof, the existing parasite infestations of animals are treated or controlled.
In one embodiment of the invention and/or embodiments thereof, existing parasite infestations of companion animals (preferably dogs or cats) are treated, preferably ticks and/or fleas, preferably ticks and fleas infestations.
In one embodiment of the invention and/or embodiments thereof, the present parasite infestations of ruminants, preferably cattle, are treated, preferably ticks infestations. In one embodiment, the tick is a single host tick. In another embodiment, the tick is a multi-host tick.
A single administration of the compounds of the invention and/or embodiments thereof is generally sufficient to treat parasitic infestations. While such a single dose is generally preferred, it is contemplated that multiple doses may be used for a single treatment.
The compounds according to the invention are useful in medicine, in particular in medicine for the treatment and control of such parasite infestations in animals. In such medicaments, the concentration of the compound of the invention and/or embodiments thereof is present in an effective amount to an animal in need thereof.
An "effective amount" is the amount or quantity of a compound required to cause a significant reduction in and/or to inhibit, in whole or in part, parasite infestation by animals, by an ectoparasite population of the infested animal. Alternatively, this may mean that the amount, dosage or number of parasites present in or around the animal's house (e.g., house, building, pasture, etc.) may be effectively controlled and/or reduced.
This amount can be readily determined by observing or detecting the number of parasites in the animal before and after contact with the compound. When the compound exhibits an effect by feeding/ingestion by the parasite, the effective amount typically constitutes an amount that results in a generally toxic tissue and/or blood concentration when ingested by the parasite of interest.
To determine that an effective reduction of animal infestation, or an effective control and/or reduction of parasites in the surrounding environment, has occurred, and thus: factors that constitute this effective amount can be readily determined by comparing the number of parasites on or in the animal's environment before and after administration of the compounds described herein.
Detection may be accomplished, for example, by counting the number of parasites visible on the animal, or by counting parasites in the surrounding environment using traps or other detection means.
The difference in the number of counts performed before and after treatment indicates the efficacy of the administered dose, e.g., the parasite count is reduced by an amount of 5% to about 100% after the first administration.
Thus, although a 100% or nearly 100% reduction is targeted, a reduction in parasite count of about 50% may already constitute a significant reduction. This is because even such modest reductions have reduced certain symptoms of the affected animal and/or may restore the animal to an increased economic production level.
In one embodiment, an effective amount of the active agent achieves at least about 80% or at least about 90% effectiveness against the target parasite. In a particularly preferred embodiment, the efficacy is at least about 95%.
In preferred embodiments, reduced or achieved control and/or reduction of infestation on an animal means that the number of parasites of a particular type is reduced by at least 50, 60, 70, 75, 80, 85, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99 or even 100% in order of preference.
The duration of activity or potency (i.e. "knockdown", onset and/or sustained effect of activity) may be a major consideration in the selection of antiparasitic products. The evaluation of the product is based on its immediate and residual kill rate and efficacy duration. When trying to reduce the likelihood of a parasite-transmitted pathogen, a rapid residual kill rate (sometimes referred to as onset of activity/efficacy) is critical. The duration of time that the compound is effective against the various ectoparasites is important for the desired interval of treatment. This is particularly important, especially in view of the long activity that can be obtained when low doses are used that are non-toxic to the target animal.
In another embodiment, the compounds of the invention have an efficacy against ectoparasites of at least 95.0% or more for about 3 months or more.
In other embodiments, the compounds of the present invention have at least about 90% efficacy against ectoparasites (including, but not limited to, fleas, ticks, mites, and parasitic flies) for about 7 months or more, about 8 months or more, or about 9 months or more.
In other embodiments, the compounds of the present invention have an efficacy of at least about 90% of the antibody ectoparasites (including, but not limited to, fleas, ticks, mites, and parasitic flies) for about 10 months or more, about 11 months or more, or even about 12 months or more.
Thus, one embodiment of the invention is a method wherein the compound is administered monthly.
Thus, in another embodiment of the invention, the compound is administered every 6 weeks.
Thus, in another embodiment of the invention, the compound is administered every 2 months.
Thus, in another embodiment of the invention, the compound is administered every 10 weeks.
Thus, in another embodiment of the invention, the compound is administered every 3 months.
Thus, in another embodiment of the invention, the compound is administered every 6 months.
Thus, in another embodiment of the invention, the compound is administered every 9 months.
In one embodiment, an effective dose of the compound protects animals, particularly cattle, from infestation or infestation by parasites (e.g., ticks, mites, lice and/or stings flies) for at least 48 days.
Thus, in one embodiment of the invention, the compound is administered every 6 weeks (about 1.5 months), 7 weeks, 8 weeks (about 2 months), 9 weeks, or 10 weeks (about 2.5 months).
In another embodiment of the invention, it has surprisingly been found that the compounds of the invention provide 80% efficacy as early as 3 days after administration and provide a long lasting efficacy. For many compounds, this early onset of action against ticks was observed even after topical application.
In still other embodiments of the invention, the compound provides an early onset of activity, meaning efficacy as early as 3 days or less, such as 2 days or 1 day, 80% or more, after administration.
The rapid action and long lasting control afforded by the compounds of the present invention is unexpected.
Thus, in a further aspect, the present invention provides a pharmaceutical composition comprising an effective amount of one or more, preferably one, compounds according to the invention and one or more pharmaceutically acceptable excipients.
The compounds according to the invention are useful for controlling parasite infestations of animals. One of ordinary skill in the art can generally determine an "effective" dose by, for example, observing or detecting a change in the clinical condition or behavior of the host animal, and by observing or detecting a relative change in the number of parasites following the treatment.
An "effective amount" is an amount or quantity of a compound that is required to cause a significant reduction in the number of ectoparasites that infest an animal and/or to inhibit, in whole or in part, the occurrence of parasitic infestation in an animal. Alternatively, this may refer to an amount, dose or quantity effective to control and/or reduce the presence of parasites in an animal's house or its surroundings (e.g., house, building, pasture, field, etc.).
This amount can be readily determined by observing or detecting the amount of a pathogen (e.g., parasite number) directly and/or indirectly (e.g., by contacting an article, surface, branch, or animal) before and after contacting a pathogen (e.g., parasite) sample (including stages thereof) with a compound according to the invention. When the compound exhibits an effect by feeding/ingestion by the parasite, the effective amount typically constitutes an amount that results in a generally toxic tissue and/or blood concentration when ingested by the parasite of interest.
To determine that an effective reduction of animal infestation, or an effective control and/or reduction of parasites in the surrounding environment, has occurred, and thus: factors that constitute this effective amount can be readily determined by comparing the number of parasites on or in the animal's environment before and after administration of the compounds described herein.
Detection may be accomplished, for example, by counting the number of parasites visible on the animal, or by counting parasites in the surrounding environment using traps or other detection means.
The difference in the number of counts performed before and after treatment indicates the efficacy of the administered dose, e.g., the parasite count is reduced by an amount of 5% to about 100% after the first administration.
Thus, although a 100% or nearly 100% reduction is targeted, a reduction in parasite count of about 50% may already constitute a significant reduction. This is because even such modest reductions have reduced certain symptoms of the affected animal and/or may restore the animal to an increased economic production level.
In one embodiment, an effective amount of the active agent achieves at least about 80% or at least about 90% effectiveness against the target parasite. In a particularly preferred embodiment, the efficacy is at least about 95%.
In preferred embodiments, a reduction in animal infestation or control and/or reduction achieved means a reduction in the number of parasites of a particular type by at least 50, 60, 70, 75, 80, 85, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99 or even 100% in order of preference.
Animals to be treated
The compounds or compositions are useful for controlling parasite infestations in a range of animals, particularly domestic animals.
The term "livestock" as used herein includes any animal that is raised by humans as a companion animal, pet, work animal, or as livestock for food, fur, leather, wool, or other animal products; or an animal found to be related to humans and in need of control of ectoparasites of the animal.
In one embodiment, the animals are warm-blooded animals. Such warm-blooded animals include poultry animals (e.g., chickens and turkeys) and mammals, such as mammals. Mammals include, for example, farm or livestock mammals (e.g., pigs, cows, sheep, goats, etc.), laboratory mammals (e.g., mice, rats, gerbils, etc.), companion mammals (e.g., dogs, cats, horses, etc.), fur animals (e.g., mink, fox, chinchillas, rabbits, etc.), and wild and zoo mammals (e.g., buffalo, deer, etc.).
The compounds according to the invention are particularly suitable for use in livestock, for feeding meat and milk or wool, or as working animals, in particular ruminants, such as cattle, sheep, goats, deer, camels, alpacas.
In one embodiment, the animal is a bovine, such as a bovine. In this specification, bovine is a ruminant mammal of the genus bovine and includes, but is not limited to, cattle such as beef cattle, heifers, dairy cows (both lactating and non-lactating), calves, bulls, and buffalo. Especially preferred are beef cattle, i.e. bovine animals raised as meat or cows. In another embodiment, the animal is a sheep. In another embodiment, the animal is a goat.
In another preferred embodiment, the methods and compositions of the invention are used for the treatment and prevention of parasitic infections and infestations in ruminants, particularly domestic cattle or sheep. The methods and compositions are particularly effective for single host ticks, particularly rhipicephalus microplus (microplus) when treating livestock such as cattle or sheep,
in some embodiments, the compounds are used to treat companion animals, particularly canine or feline. In one embodiment, the composition is used to treat dogs (e.g., dogs). In other embodiments, the compounds are used to treat felines (e.g., domestic cats).
In preferred embodiments, the present invention provides methods and compositions for treating or preventing parasitic infections and infestations of companion animals, including, but not limited to, cats and dogs. The methods and compositions are particularly effective for preventing or treating infestation of cats and dogs by parasites such as fleas and/or ticks.
The compounds are also useful in the treatment of warm-blooded non-mammals such as poultry (e.g., turkeys, chickens, geese, ducks, parrots, etc.).
In one embodiment, the compounds are used to treat cold blood animals, such as fish (e.g., salmon, trout, sea bass, sea bream, or ornamental fish such as koi, etc.). Thus, in one embodiment, the animals are fish.
In a preferred embodiment, the fish treated is salmon. The term "salmon" within the scope of the present invention is understood to include all representatives of the salmonidae, in particular representatives of the salmonidae, and preferably atlantic salmon (Salmo salar), rainbow trout (Oncorhynchus mykiss), brown trout or sea trout (S.trutta).
The compounds used in the present invention may be provided to a single animal during treatment.
In particular for domestic animals it is more advantageous to treat a group of animals simultaneously, or all animals in a single stable, fence, nest, group, stable or pasture. For companion animals, it is preferred to treat all animals at risk of parasitic infestation simultaneously.
A single administration of a compound according to the invention or a compound corresponding to the use according to the invention is generally sufficient to treat parasitic infestations. While such a single dose is generally preferred, it is contemplated that multiple doses may be used.
The frequency of administration depends on a variety of factors, and may be once daily, once weekly, once monthly, every two months, three months, four months, or six months, or once annually, a single dose is administered. In some embodiments, the frequency of administration may be, for example, weekly, biweekly, monthly, bi-monthly, 3-monthly, 4-monthly, 5-monthly, 6-monthly, or 12-monthly, or an equivalent frequency of administration expressed in days or weeks approaching the frequency.
The duration of activity or potency (i.e., the "knockdown", onset of activity, and/or sustained effect) may be a major consideration in the selection of antiparasitic products. The evaluation of the product is based on its immediate and residual kill rate and efficacy duration. When attempting to reduce the likelihood of tick parasites transmitting pathogens, a rapid residual kill rate (sometimes referred to as activity/efficacy onset) is critical. The duration of time that the compound is effective against the various ectoparasites is important for the desired treatment interval. This is particularly important, especially in view of the long activity obtained when low doses are used which are non-toxic to the target animal.
In one embodiment, the composition exhibits durable efficacy and provides protection against parasites in livestock for at least one month.
In another embodiment, the compounds of the invention exhibit a very long lasting efficacy of at least 50% for ticks for at least 1 month, at least 2 months, at least 3 months or at least 4 months.
In another embodiment, the compounds of the invention exhibit a very long lasting efficacy of at least 70% for ticks for at least 1 month, at least 2 months, at least 3 months or at least 4 months.
In another embodiment, the compounds of the invention exhibit a very long lasting efficacy against parasites (e.g., ticks) of at least 90%, for example, for a period of at least 1 month, at least 2 months, at least 3 months, or at least 4 months.
Thus, one embodiment of the invention is a method wherein the compound is administered monthly.
Thus, in another embodiment of the invention, the compound is administered every 6 weeks.
Thus, in another embodiment of the invention, the compound is administered every 2 months.
Thus, in another embodiment of the invention, the compound is administered every 3 months.
In one embodiment, an effective dose of the compound protects animals, particularly cattle, from infestation or re-infestation by parasites (e.g., ticks, mites, lice and/or stings flies) for at least 48 days.
Thus, in one embodiment of the invention, the compound is administered every 6 weeks (about 1.5 months), 7 weeks, 8 weeks (about 2 months), 9 weeks, or 10 weeks (about 2.5 months).
In another embodiment of the present invention, it has surprisingly been found that the compounds of the present invention provide 80% efficacy as early as 2-6 days post-administration and provide a sustained efficacy. For many compounds, this early onset of activity was observed to be effective against ticks even after topical application.
In still other embodiments of the invention, the compounds provide early onset of activity, meaning efficacy of 80% or more as early as 3 days, 2 days, or 1 day after administration.
The rapid action and long lasting control afforded by the compounds of the present invention is unexpected.
The compounds used in the present invention may be provided to a single animal during treatment.
In particular for domestic animals it is more advantageous to treat a group of animals simultaneously, or all animals in a single stable, fence, nest, group, stable or pasture. For companion animals, it is desirable to treat all animals at risk of parasitic infestation simultaneously.
Generally, a dose of about 0.001 to about 100mg per kilogram of body weight will be used as a single dose, but of course there may be circumstances in which higher or lower dose ranges are indicated and such circumstances are within the scope of the invention.
In some embodiments, for example, about 0.01 to about 100mg/kg body weight is administered.
In other embodiments, for example, about 0.01 to about 50mg/kg body weight is administered.
In some such embodiments, for example, about 0.1 to about 40mg/kg body weight is administered.
In other such embodiments, about 1 to about 30mg/kg body weight is administered. Larger doses tend to provide longer duration of activity/potency.
Factors affecting the preferred dosage may include, for example, parasite species infestations and stages of parasite development to be treated, type of infected animal (e.g., species and breed), age, size, sex, diet, activity and condition; a route of administration; pharmacological considerations such as the activity, efficacy, pharmacokinetics and toxicological profile of the particular composition being administered; and whether the compounds according to the invention are administered as part of a combined active ingredient. Thus, the preferred amounts of the compounds according to the invention may vary and may therefore deviate from the typical dosages described above.
For many animals, the dosage and composition comprising the compound is selected to maintain a blood level of at least about 30ng/ml, more preferably about 40ng/ml, about 50ng/ml, or 60 ng/ml.
In some embodiments, the concentration of the compound in the plasma sufficient to achieve at least 80% anti-tick efficacy is less than or equal to about 60ng/ml.
Generally, a dose of about 0.001 to about 100mg per kilogram of body weight administered in a single dose or in divided doses over a period of 1 to 5 days will be satisfactory, but of course there may be circumstances in which a higher or lower dose range is indicated, and this is also within the scope of the invention.
When the compounds according to the invention are administered orally by oral administration, the total dose is generally greater than about 0.01mg/kg (i.e., milligrams of the compounds of the invention per kilogram of body weight of the treated animal). Oral administration of the compounds surprisingly demonstrates protection of animals from parasites, especially dogs from fleas and/or ticks, for an extremely long period of time.
Thus, in one embodiment, the compounds are administered orally to animals, particularly dogs, to protect the animals from parasites, particularly fleas and/or ticks, preferably from fleas and ticks.
In some such embodiments, the total dose is from about 0.01 to about 100mg/kg, from about 0.01 to about 50mg/kg, from about 0.1 to about 25mg/kg, or from about 1 to about 20mg/kg. For example, for sheep, the dosage is typically about 0.5 to about 15mg/kg, about 1 to about 10mg/kg. The same dosage range may be applicable to other routes of administration.
For example, in some embodiments, a higher dosage range is used for topical pour-on applications.
In one embodiment, the compound is administered by topical pour-on administration to animals, especially domestic cattle, to protect the animals from parasites, especially acarina parasites, preferably ticks.
For example, in some embodiments, the same dosage range is used for subcutaneous administration.
In one embodiment, the compound is administered by injection, in particular subcutaneously to animals, especially cattle, to protect the animals from parasites, especially mites, preferably ticks.
If the compounds according to the invention are administered parenterally by injection, in particular by subcutaneous administration, the concentration of the compounds according to the invention in the dosage form is preferably sufficient to provide the desired effective amount of the compounds according to the invention in a volume acceptable for parenteral administration. Furthermore, such injections should not result in severe injection site reactions.
In some embodiments, one or more, preferably one, of the compounds according to the invention is used for controlling infestation by parasites, in particular ectoparasites, in particular ticks, which are resistant to one or more of the commercially available and known parasiticidal compounds.
Thus, the compounds of the invention are useful in animals infested or at risk of being infested by parasites, particularly ticks that are resistant to any of the organophosphate, pyrethroid or benzoylphenylurea compounds, and will still provide effective treatment/protection.
Factors affecting the preferred dosage may include, for example, parasite species infestation and stage of parasite development to be treated, type of animal infested (e.g., species and breed), age, size, sex, diet, activity and condition; a route of administration; pharmacological considerations such as activity, efficacy, pharmacokinetic and toxicological profiles of the particular composition being administered; and whether the compounds according to the invention are administered as part of a combination of active ingredients. Thus, the preferred amounts of the compounds of the present invention may vary, and thus may deviate from the typical dosages described above.
For many animals, the dosage and composition comprising the compound is selected to maintain a blood level of at least about 30ng/ml, more preferably about 40ng/ml, about 50ng/ml, or 60ng/ml.
In some embodiments, the concentration of the compound in the plasma sufficient to achieve at least 80% anti-tick efficacy is less than or equal to about 60ng/ml.
Route of administration
When the compounds of the present invention are administered orally, the total dose is typically greater than about 0.01 mg/kg (i.e., milligrams of the compound of the present invention per kilogram of body weight of the subject animal).
In some such embodiments, the total dose is from about 0.01 to about 100mg/kg, from about 0.01 to about 50mg/kg, from about 0.1 to about 25mg/kg, or from about 1 to about 20. For sheep, for example, the dosage is typically about 0.5 to about 15mg/kg, about 1 to about 10mg/kg. The same dosage range may be applicable to other dosage routes.
For example, in some embodiments, higher dosage ranges are used when topically applied.
For example, in some embodiments, the same dosage range is used for subcutaneous administration.
If the compounds according to the invention are administered parenterally by injection, in particular by subcutaneous administration, the concentration of the compounds according to the invention in the dosage form is preferably sufficient to provide the desired therapeutically effective amount of the compounds according to the invention in a volume acceptable for parenteral administration. Furthermore, such injection should not lead to severe injection site reactions.
In some embodiments, one or more, preferably one, of the compounds according to the invention is used for controlling infestation of parasites, in particular ectoparasites, in particular ticks, which are resistant to one or more of the commercially available and known parasiticidal compounds.
Thus, the compounds of the invention are useful in animals infested by parasites or at risk of being infested by parasites (particularly ticks, which are resistant to any of the organophosphate, synthetic pyrethroid or benzoylphenylurea compounds) and still provide effective treatment/protection.
Dosage form
The compounds according to the invention can be administered in a variety of different dosage forms.
The term "dosage form" refers to a product in which a compound according to the invention is formulated to be suitable for administration to an animal by the envisaged route of administration. These dosage forms are sometimes referred to herein as formulations or pharmaceutical compositions.
In any event, the type of formulation selected for the dosage form will depend on the particular purpose envisaged and the physical, chemical and biological properties of the compound according to the invention.
The invention also relates to a veterinary composition comprising an effective amount of a compound of formula (I) as defined in any of the embodiments described herein and an inert carrier or formulation adjuvant. The compositions are useful for treating and controlling parasite infestations in animals, as described herein.
Suitably, the veterinary composition is a topical composition, an oral composition or an injectable composition.
The invention also relates to a veterinary composition comprising an effective amount of a compound of formula (I) as defined in any of the embodiments described herein and an inert carrier or formulation adjuvant. Suitably, the composition is for use in the treatment and control of parasite infestations of animals as described herein.
In one embodiment of the application and/or embodiments thereof, the veterinary composition is a topical composition.
In one embodiment of the application and/or embodiments thereof, the veterinary composition is an oral composition.
In one embodiment of the application and/or embodiments thereof, the veterinary composition is an injectable composition.
Thus, in a further aspect, the present application provides a pharmaceutical composition comprising an effective amount of one or more, preferably one, compounds according to the application and one or more pharmaceutically acceptable excipients.
The terms "excipient", "diluent" or "carrier" are used herein to describe any ingredient other than the compound of formula (I) or any additional antiparasitic agent in the dosage form. The choice of excipient, diluent, or carrier will depend in large part on factors such as the particular route and mode of administration, the effect of the excipient, carrier, or diluent on solubility and stability, and the nature of the dosage form.
Pharmaceutically acceptable, for example with respect to salts and composition components such as carriers, as used in the present application, include "dermatologically acceptable" and "veterinarily acceptable" for topical dosage forms, and thus independently include both human and animal applications.
Dosage forms useful in the present invention may be liquid, semi-solid or solid dosage forms.
The liquid dosage form of the compound is typically a solution, suspension or emulsion. Solutions are two or more components that form a single phase that is uniform at the molecular level. The suspension is composed of insoluble solid particles dispersed in a liquid medium, the solid particles comprising from about 0.5% to about 30% of the suspension. The liquid may be aqueous, oily or both. Emulsions are heterogeneous dispersions of one immiscible liquid in another; its stability depends on the emulsifier.
The dry powder (or particles) for reconstitution is reconstituted as a solution or suspension immediately prior to injection. The main advantage of the dosage form is that the instability problem of the solution or suspension is overcome.
One possible route of administration is the oral route, wherein the compounds according to the invention are administered orally. Oral dosage forms suitable for oral administration include liquids (e.g., drenching or drinking water formulations), semisolids (e.g., pastes, gels), and solids (e.g., tablets, capsules, powders, granules, chewable foods, pre-mixes, and pharmaceutical blocks (mediated blocks)).
Many veterinary compositions are known to be suitable for oral administration to animals, but they vary from animal species to animal species. For sheep, the pharmaceutically active ingredient is usually administered orally, either as a solid (e.g. tablets or boluses) or as a liquid, and via its feed or drinking water. In large sheep and cattle, the use of oral drenches is the most common oral dosage form, especially when the anthelmintic compound is administered.
Drenching refers to the oral administration of a liquid, potentially slightly viscous composition containing the compound and excipients into the throat of a sheep using a specific dispensing gun that dispenses the compound.
Drenching is a liquid oral formulation that is administered directly into the mouth/throat of an animal, particularly livestock, by a "drenching gun" or syringe or another suitable device. The use of solution or suspension formulations may be convenient when the composition is administered in the drinking water of the animal recipient or as a drench. The formulation may be, for example, a concentrated suspension mixed with water or a dry formulation mixed and suspended in water.
Semisolid oral formulations (pastes or gels) are usually applied directly into the animal's mouth by means of an applicator or mixed with feed.
The solid oral formulations may be administered directly to the animal (tablet, capsule, bolus) or may be mixed with feed or administered via pharmaceutical feed blocks.
When the oral formulation is administered by feed of a non-human animal, it may be fed, for example, as a separate feed or as a chewable food. Alternatively (or additionally), it may be, for example, intimately dispersed in the animal recipient's conventional feed, used as a top dressing, or in the form of solid particles, paste or liquid added to the finished feed. When the oral formulation is administered as a feed additive, it may be convenient to prepare a "premix" in which the oral formulation is dispersed in a liquid or solid carrier. The "premix" is then dispersed in the animal feed using, for example, a conventional mixer to ensure a more uniform distribution of the compounds in the feed.
Several modified release delivery systems have been developed that take advantage of the unique anatomy of the ruminant forestomach, i.e., for intra-ruminal administration. Intra-ruminal boluses are specific formulations for ruminants (cattle, sheep, goats, buffalo, camels, deer, etc.). It is a veterinary sustained release drug delivery system that remains within the rumen omentum sac (rumen-ocular sac) of ruminants for long periods of time, and wherein the therapeutically active substance has a predictable and delayed release pattern. Such intra-ruminal boluses are typically administered using a bolus tool or another suitable device.
Alternatively, the compounds according to the invention may also be administered by non-oral routes of administration, for example topically (e.g. by spray-dripping, pouring (pouron), spraying) or parenterally (e.g. subcutaneous injection, intravenous injection, intramuscular injection, etc.).
For example, the compounds according to the present invention may be topically applied using transdermal formulations (i.e., transdermal formulations).
Topical dosage forms suitable for topical application include liquids (e.g., bath, spray droplet), semisolids (e.g., cream, gel), and solids (e.g., patch, powder, collar). Typical topical formulations for animals are liquid or semi-liquid dosage forms.
Typical formulations for topical and transdermal administration include, for example, pour-on (pou-on) formulations, spray drops, infusion solutions, sprays, mousses, shampoos, powders, gels, hydrogels, lotions, solutions, creams, ointments, dusting powders, dressings, foams, films, skin patches, limb strips, collars, ear tags, wafers, sponges, fibers, bandages and microemulsions. When the liquid formulation is applied topically to the skin, it may be applied by, for example, pouring (pouring or spraying), painting, rubbing, spraying, sprinkling, dipping, bathing or washing.
For example, pour-on or spray-on methods include applying the formulation to a specific area of skin or fur, such as the neck or diaphysis of an animal. This may be accomplished, for example, by applying a cotton swab or drop of a pour-on or spray-on formulation to a relatively small area of the skin or coat of the recipient animal (i.e., typically no more than about 10% of the skin or coat of the recipient animal). In some embodiments, due to the diffuse nature of the components in the formulation and the movement of the animal, the compounds according to the invention are dispersed from the application site to a wider area of the pelt while being absorbed through the skin and distributed through the liquid and/or tissue of the animal recipient.
Parenteral formulations and delivery systems for non-oral routes include liquids (e.g., solutions, suspensions, emulsions, and dry powders for reconstitution), semisolids, and solids (e.g., implants). Most implants used in veterinary medicine are compressed tablet or dispersion matrix systems, in which the drug is homogeneously dispersed in a biodegradable or non-degradable polymer, or as an extruded product.
Pharmaceutical composition
The invention also relates to pharmaceutical compositions (or medicaments) comprising one or more, preferably one, of the compounds according to the invention. The composition may also (and preferably does) comprise one or more pharmaceutically acceptable excipients. The following subject matter regarding pharmaceutical compositions also applies to pharmaceutical compositions comprising compounds corresponding to the use according to the invention.
The pharmaceutical compositions of the invention may be manufactured, for example, by methods known in the art. These include, for example, various known mixing, dissolving, granulating, emulsifying, encapsulating, entrapping and lyophilizing processes. The optimal formulation depends on, for example, the route of administration (e.g., oral, parenteral by injection, topical).
For example, solid dosage forms may be prepared by intimately and homogeneously mixing the compound with fillers, binders, lubricants, glidants, disintegrants, flavoring agents (e.g., sweeteners), buffering agents, preservatives, pharmaceutical grade dyes or pigments, and controlled release agents, for example.
Oral dosage forms other than solids may be prepared by mixing the compound with, for example, one or more solvents, tackifiers, surfactants, preservatives, stabilizers, resins, fillers, binders, lubricants, glidants, disintegrants, co-solvents, sweeteners, perfumes, buffers, suspending agents and pharmaceutical grade dyes or pigments.
Contemplated binders include, for example, starch, gelatin, acacia, and carboxymethylcellulose.
Contemplated lubricants include, for example, magnesium stearate, stearic acid, and talc.
Contemplated disintegrants include, for example, corn starch, alginic acid, sodium carboxymethyl cellulose, and croscarmellose sodium.
Contemplated buffers include, for example, sodium citrate, and magnesium and calcium carbonates and bicarbonates.
Contemplated solvents include, for example, water, pyrrolidone solvents, vegetable oils, mineral oils, and synthetic oils such as medium chain triglycerides, for example Miglyol 812 or 840. Physiological saline solution or glycols (e.g., propylene glycol or polyethylene glycol) may also be included. The solvent is preferably of sufficient chemical nature and amount to allow the compound to remain dissolved at the temperature at which the composition is stored and used.
Contemplated tackifiers include, for example, polyethylene, methylcellulose, sodium carboxymethylcellulose, hydroxypropyl methylcellulose, hydroxypropyl cellulose, sodium alginate, carbomer, povidone, acacia, guar gum, xanthan gum, tragacanth, methylcellulose, carbomer gum, xanthan gum, guar gum, povidone, sodium carboxymethylcellulose, magnesium aluminum silicate, carboxyvinyl polymers, carrageenan, hydroxyethyl cellulose, laponite, water soluble salts of cellulose ethers, natural gums, colloidal magnesium aluminum silicate or finely divided silica, homopolymers of acrylic acid crosslinked with alkyl ethers of pentaerythritol or alkyl ethers of sucrose, and carbomers.
Contemplated surfactants include, for example, sodium lauryl sulfate, polyoxyethylene sorbitan fatty acid esters; polyoxyethylene monoalkyl ethers; sucrose monoesters; lanolin esters and ethers; alkyl sulfate; and sodium, potassium and ammonium salts of fatty acids.
Contemplated preservatives include, for example, phenol, alkyl esters of parahydroxybenzoic acid (e.g., methyl parahydroxybenzoate (or "methyl paraben") and propyl parahydroxybenzoate (or "propyl paraben"), sorbic acid, o-phenylphenol benzoic acid and salts thereof, chlorobutanol, benzyl alcohol, thimerosal, acetic acid and phenylmercuric nitrate, nitromerosal, benzalkonium chloride, and cetylpyridinium chloride.
Contemplated stabilizers include, for example, chelators and antioxidants.
The solid dosage form may also contain, for example, one or more excipients that control the release of the compound. For example, it is contemplated that the compound may be dispersed in, for example, hydroxypropyl methylcellulose. Some oral dosage forms (e.g., tablets and pills) may also be prepared with enteric coatings.
The topical route of administration uses, for example, concentrated liquid or semi-liquid solutions, suspensions (aqueous or non-aqueous), emulsions (water-in-oil or oil-in-water) or microemulsions comprising compounds dissolved, suspended or emulsified in a pharmaceutically acceptable liquid vehicle. In these embodiments, a crystallization inhibitor may generally optionally be present.
Such pour-on or spray-on formulations may be prepared by dissolving, suspending or emulsifying the compound in a suitable skin-friendly solvent or solvent mixture. Other excipients, such as surfactants, colorants, antioxidants, stabilizers, binders, and the like, may also be included. Contemplated solvents include, for example, water, alkanols, diols, polyethylene glycols, polypropylene glycols, glycerol, benzyl alcohol, phenethyl alcohol, phenoxyethanol, ethyl acetate, butyl acetate, benzyl benzoate, dipropylene glycol monomethyl ether, diethylene glycol monobutyl ether, acetone, methyl ethyl ketone, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, liquid paraffin, silicones, dimethylacetamide, N-methylpyrrolidone or 2, 2-dimethyl-4-oxo-methylene-1, 3-dioxolane.
In some embodiments, the topical formulation (particularly a pour-on or spray-on formulation) comprises a carrier that facilitates absorption or penetration of the compound through the skin into the blood stream, other body fluids (lymph), and/or body tissue (adipose tissue). Examples of contemplated skin penetration enhancers include, for example, dimethyl sulfoxide, isopropyl myristate, dipropylene glycol pelargonate, silicone oils, aliphatic esters, triglycerides, and fatty alcohols.
The topical formulation may also (or alternatively) comprise, for example, one or more dispersing agents. These materials serve as carriers that help distribute the active ingredient over the coat or skin of the animal recipient. They may include, for example, isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides and/or fatty alcohols. Various diffusion oil/solvent combinations may also be suitable, such as oily solutions, alcoholic solutions and isopropanol solutions (e.g. solutions of 2-octyldodecanol or oleyl alcohol), solutions of monocarboxylic acid esters (e.g. isopropyl myristate, isopropyl palmitate, oxalic acid ester of lauric acid, oleyl oleate, decyl oleate, hexyl laurate, oleyl oleate, decyl oleate and caproic acid esters of saturated fatty alcohols having carbon chains of 12-18 carbons), solutions of dicarboxylic acid esters (e.g. dibutyl phthalate, diisopropyl isophthalate, diisopropyl adipate and di-n-butyl adipate) or solutions of aliphatic acid esters (e.g. glycols). When the formulation comprises a dispersing agent, it may also advantageously comprise a dispersing agent, such as pyrrolidin-2-one, N-alkylpyrrolidin-2-one, acetone, polyethylene glycol or ethers or esters thereof, propylene glycol or synthetic triglycerides.
Injectable formulations may be prepared according to, for example, known techniques using suitable solvents, solubilisers, protectants, dispersants, wetting agents and/or suspending agents. Contemplated carrier materials include, for example, water, ethanol, butanol, benzyl alcohol, glycerol, 1, 3-butanediol, ringer's solution, isotonic sodium chloride solution, mild fixed oils (e.g., synthetic mono-or diglycerides), vegetable oils (e.g., corn oil), fatty acids (e.g., oleic acid), dimethylacetamide, surfactants (e.g., ionic and nonionic detergents), N-methylpyrrolidone, propylene glycol, and/or polyethylene glycols (e.g., polyethylene glycol 400). Contemplated solubilizing agents include, for example, polyvinylpyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan esters, and the like. Contemplated protectants include, for example, benzyl alcohol, chlorobutanol, parabens, n-butanol, and the like.
In some embodiments, the parenteral formulation is prepared, for example, from sterile powders or granules with one or more of the carrier materials described above for the other formulations. The compound is, for example, dissolved or suspended in a liquid comprising water, polyethylene glycol, propylene glycol, ethanol, corn oil, cottonseed oil, peanut oil, sesame oil, benzyl alcohol, sodium chloride, and/or various buffers. If necessary, the pH is generally adjusted with a suitable acid, base or buffer.
For further aspects on the formulation of drugs and various excipients see, for example, renaro, a.r. et al, edit "leimington: science and practice of pharmacy (Lippincott Williams & Wilkins, 20 th edition, 2000).
The concentration of the compounds according to the invention in the dosage form of application may vary greatly depending, for example, on the route of administration. Typically, the concentration in the dosage form is from about 1% to about 70% by weight. In some such embodiments, for example, the concentration is from about 1 to about 50 weight percent, or from about 10 to about 50 weight percent. In other embodiments, the concentration is about 35 to about 65 weight percent, about 40 to about 60 weight percent, about 45 to about 55 weight percent, or about 50 weight percent.
Thus, in a further aspect, the present invention provides a pharmaceutical composition comprising an effective amount of one or more, preferably one, compounds according to the invention and one or more pharmaceutically acceptable excipients.
In any event, the type of formulation selected for the dosage form will depend on the particular purpose contemplated as well as the physical, chemical and biological properties of the compounds of the present invention.
Topical pharmaceutical composition
In one embodiment, the compounds of formulae (I) - (XCII) according to the invention and/or embodiments thereof are topically applied to animals, preferably by pouring or spray-dripping.
In another aspect of the present invention and/or embodiments thereof, there is provided a use or method for protecting an animal from or treating parasitic infestation/infection of an animal comprising administering to the animal a topical composition comprising an effective amount of at least one compound of the present invention and a pharmaceutically acceptable carrier suitable for use on the skin of the animal.
In some embodiments of the invention, the topical compositions are formulated to control the permeation rate of the compound, thereby maintaining an effective level of active in the plasma over an extended period of time, and significantly extending the duration of efficacy.
In a specific embodiment, the present invention relates to a veterinary pharmaceutical composition comprising a compound of formula (I) according to the present invention and/or embodiments thereof and a pharmaceutically acceptable oily carrier.
The topical composition is administered to the animal in an amount of from about 0.5mg to about 10mg, even more typically from about 1mg to about 2.5mg of a compound of formula (I) - (XCII) according to the invention and/or any embodiment thereof, in particular a compound of formula (LIX), formula (LIXa), formula (LXI) or formula (LXIa), per kilogram of body weight of the animal being treated.
Compounds of formula (LIX)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
Compounds of formula (LIXa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
Compounds of formula (LXI)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
Compounds of formula (LXIa)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof.
However, it will be apparent to those skilled in the art that the effective amount to control a particular parasite in an animal will depend on a variety of factors including, for example, the particular compound of formula (I) in the composition, the animal species, the age, sex and health of the animal, the particular parasite infesting the animal, and the severity of the parasite infestation. For any given situation, the skilled artisan can readily determine an effective amount using standard techniques and routine experimentation.
The compositions of the present invention comprise an oily carrier that is pharmaceutically effective.
"pharmaceutically or veterinarily acceptable carrier" refers to a carrier that can be used to prepare a pharmaceutical composition that is generally safe, non-toxic, and biologically or otherwise undesirable, including carriers that are acceptable for veterinary or pharmaceutical use.
As used herein, "oily carrier" refers to a carrier that uses oil as a solvent for dissolving the compound, or otherwise as a medium for dispersing or suspending the compound in a powder form that is insoluble in the oil. This means that the oil comprises at least 50% by weight of the total amount of carrier and may include one or more additional non-volatile co-solvents.
In a preferred embodiment, the oil comprises at least 99% to 99.5% by weight of the total amount of carrier.
According to the present invention, the oil may be a solvent that dissolves, disperses and/or suspends the compounds of formulae (I) - (XCII) and/or embodiments thereof, and may include, for example; monoglyceride, diglyceride, triglyceride, medium Chain Triglyceride (MCT), sesame oil, peanut oil (peanut oil), castor oil, olive oil, corn oil, cottonseed oil, soybean oil, peppermint oil, coconut oil, palm kernel oil, safflower oil, and the like, but is not particularly limited thereto. These may be used alone or as a mixture of two or more thereof.
In a preferred embodiment, the carrier consists of a fatty acid ester. Fatty Acid Esters (FAEs) are a type of ester derived from a combination of fatty acids and alcohols. When the alcohol component is glycerol, the fatty acid ester produced may be a monoglyceride, diglyceride or triglyceride.
In an alternative embodiment, the oily carrier comprises a fatty acid ester.
Preferably, the fatty acid ester is a medium chain triglyceride. Medium Chain Triglycerides (MCT) have fatty acid chains of 6-12 carbon atoms and for pharmaceutical refining grade MCT oils, each chain has 8-10 carbon atoms.
The MCT oil may comprise C 8 -C 10 Triglycerides of fatty acids, or propylene glycol diesters of these fatty acids, or mixtures of both triglycerides and propylene glycol diesters. Preferably, these C8-C10 fatty acids are fully saturated, e.gSuch as n-octanoic acid and n-decanoic acid. These fatty acids can be conveniently prepared by commercially fractionating naturally occurring vegetable (e.g., coconut) oils to yield predominantly C8-10 fatty acids, and then esterifying these acids with selected alcohols.
Fractionated vegetable oils having the desired composition are commercially available. Specific examples of these MCT oils are as capric/caprylic triglyceridesAnd +.F. as propylene glycol dicaprylate/caprate >Most preferred is propylene glycol dicaprylate/caprate, such as Miglyol 840.
Preferred additional components are glycerol monocaprylate, e.g.asAre commercially available.
A specific group of MCT oils have been found to have a combination of low irritation and suitable solvency, and are particularly suitable for compositions for topical application of the topical compounds.
These medium chain fatty acid esters have the additional advantage of a low melting point and it has surprisingly been found that Miglyol 840 results in very high transdermal penetration levels of the compound of formula (I) according to the invention and/or any embodiment thereof.
In particular, the present invention relates to a composition according to the present invention comprising a compound of the above formula (LIX), formula (LIXa), formula (LXI) or formula (LXIa) dissolved in a mixture of glycerol and propylene glycol esters of fatty acids.
An example of a composition according to the invention consists of 1% w/v of a compound of formula (I) according to the invention and/or embodiments and 99% w/v of propylene glycol dicaprylate.
Another example of a composition according to the invention consists of 1% w/v of a compound of formula (I) according to the invention and/or embodiments thereof, 20% w/v of glycerol monocaprylate and 79% w/v of propylene glycol dicaprylate.
An example of a composition according to the invention consists of 1% w/v of a compound according to formula (LIX), formula (LIXa), formula (LXI) or formula (LXIa), preferably a compound of formula (LXI) or formula (LXIa), and 99% w/v of propylene glycol dicaprylate decanoate.
Another example of a composition according to the invention consists of 1% w/v of a compound according to formula (LIX), formula (LIXa), formula (LXI) or formula (LXIa), preferably a compound of formula (LXI) or formula (LXIa), 20% w/v of glycerol monocaprylate and 79% w/v of propylene glycol dicaprylate.
Examples show how, in contrast to many topical solutions (e.g. commercial pour-on product Dectomax from Zoetis), the composition of the invention does not require rapid evaporation of the solvent at the time of application to obtain good maximum absorption (C max ) And total Absorbency (AUC).
In certain compositions of the invention, C in the carrier 8-10 The glycol or glyceride of a fatty acid is present in an amount of from about 50% to about 99.9%, particularly from about 79% to about 99.5%, from about 85% to about 99% by weight of the composition.
Typically, the composition comprises from about 0.5% to about 10% w/v, preferably 1% of the compound of formula (I), b) from about 10% to about 40% w/v, preferably 20% of glycerol monocaprylate; and c) optionally from about 2% to about 50% w/v, preferably 79% propylene glycol dicaprylate decanoate.
In accordance with the present invention, it has been found that compositions in accordance with the present invention generally exhibit one or more beneficial technical characteristics, including desired transdermal bioavailability.
It has now been found that a single administration of such compositions generally provides effective activity against one or more ectoparasites, while also tending to provide the host animal and animal care provider with a rapid onset of activity, a long duration of activity and/or a desired safety profile. In addition, the composition is easy to administer to animals and has desirable transdermal bioavailability and coverage profile. Effective blood levels are preferably obtained by administering a composition according to the invention.
One example of a species in which the invention may be used to prevent parasites is cattle. It is known that cow leather is particularly difficult to administer transdermally, and it is surprising that such oily vehicles of the compound of formula (I) are very effective.
The transdermal liquid preparation according to the present invention has ideal absolute systemic bioavailability to promote such excellent and long-term efficacy against ectoparasites.
It has surprisingly been found that the topical compositions of the present invention comprising the compounds provide excellent anti-tick efficacy. In some embodiments, the topical compositions of the present invention comprising selected solvents and excipients produce effective active compound levels over an extended period of time.
Traditionally, pour-on compositions exhibiting systemic bioavailability require the presence in the composition of a permeation enhancer (also known as a permeation enhancer, adsorption enhancer, or accelerator) that permeates into the skin to reversibly reduce barrier resistance. Permeation enhancing activity of a variety of compounds has been evaluated, including sulfoxides (e.g., dimethyl sulfoxide, DMSO), azones (e.g., laurocapram), pyrrolidones (e.g., 2-pyrrolidone), alcohols and alkanols (ethanol or decanol), glycols (e.g., propylene glycol, PG, common excipients in topical application dosage forms), surfactants, and terpenes or fatty acids.
Thus, it is surprising that effective blood levels are obtained after pour-on administration of the compositions of the present invention without the need to include any such penetration or permeation enhancers.
It has been observed that the addition of a penetration/permeation enhancer does not provide any significant advantage for the effectiveness of the composition according to the present invention.
Unexpectedly, the pharmaceutical compositions produce bioavailability after transdermal administration, as well as therapeutic and prophylactic effects on the load of artificially obtained rhipicephalus similis.
Such effective blood levels have been achieved 2 days after administration and further maintained for a longer period of time, particularly over 70 days, at least 11 weeks or over 2.5 months.
In another embodiment, the composition exhibits a long term efficacy against ticks, mites or lice of at least 90% for a period of at least 6 weeks.
One embodiment of the invention is a method wherein the composition is administered monthly. In another embodiment of the invention, the composition is administered every six weeks. In another embodiment of the invention, the composition is administered every 2 months. In another embodiment of the invention, the composition is administered every 3 months.
The composition according to the invention is very suitable for parasite control or parasite prevention. Thus, the pharmaceutical compositions described herein are useful for treating or preventing parasite infestations, particularly for treating or preventing ectoparasites.
The composition according to the invention is particularly suitable for controlling or preventing ectoparasites, preferably ticks and/or mites, and/or flies or fly larvae, and/or lice, in non-human animals, particularly warm-blooded animals, preferably mammals. In a preferred embodiment, the non-human animal is a ruminant animal, such as a domestic cow, sheep and goat, especially a bovine animal, such as a cow, beef cow or sire.
According to a particularly preferred embodiment, the composition of the invention is used for controlling and/or preventing infestation or re-infestation of bovine ectoparasites, such as ticks, mites, lice and/or stings. In a preferred embodiment, the compositions of the invention comprising the compounds of formula (I) are administered by pour-on administration to bovine animals to control ticks, particularly rhipicephalus miniilis.
The pour-on composition according to the invention is liquid and has a sufficient viscosity to prevent leakage from the animal coat or skin by adhering sufficiently to the animal coat/skin after application, but can be easily applied, e.g. by expelling the correct amount from the container at various different temperatures.
The pour-on composition dries in a reasonable period of time without compromising the appearance of the animal, is gentle to the animal's coat, has acceptable irritation to the animal's skin, and retains its effectiveness on the animal through its normal activities (e.g., exposure to sunlight and water).
The inventors have also found that the composition according to the invention is also advantageously "rainproof", i.e. the composition is effective in controlling parasites in animals even when applied to wet animals, and in controlling parasites even when the animals are exposed to rain shortly after topical application of the composition of the invention.
This means that the therapeutic effect on the parasite is not affected by heavy rainfall (e.g. 25 mm) either before (20 min) or after (20 min and 40 min) administration to the animal.
Thus, in one aspect, the present invention relates to a veterinary pharmaceutical composition according to the invention, wherein the composition is rain-proof by showing a therapeutic effect on parasites that is not affected by heavy rainfall before or after treatment.
The topical composition should be viable as a spray or pour-on amount and appear to be safe and effective. Generally, the volume administered depends on the size and weight of the animal and the concentration of the active substance. It is preferred that the amount be administered to allow accurate dosing without causing loss of the composition, especially in the case of animal movement.
For pour-on versions of the composition, the volume applied may be on the order of about 0.3 to about 100ml. In other embodiments, the amount of pour-on composition applied may be from about 1ml to about 100ml or from about 1ml to about 50ml. In still other embodiments, the amount may be from about 5ml to about 50ml or from about 10ml to about 100ml.
Preferably, for bovine and ovine animals, 10ml or less of pour-on composition per animal is administered. Generally, pour-on compositions have a higher viscosity than compositions used for spray-drop application and, in one embodiment, comprise a tackifying component.
In one embodiment, the amount administered is 1ml of the composition per 10 kg of animal body weight. In another embodiment, the amount administered is 1ml of the composition per 20 kg of animal body weight.
Topical spray-drop compositions for external use are administered in a low volume of about 0.01 to 1ml/kg, preferably about 0.05 to 0.1ml/kg, depending on the target species, 0.3 to 100 ml/animal total volume.
The pour-on or spray-on compositions according to the invention may be applied using any manner known per se, for example using an applicator gun or metering bottle, a pipette, a syringe, a roller-on, a dropper, a capsule, a foil pack, a vial, a torque tip container (twist tip container), a metered dose aerosol or spray, and other single and multi-dose containers.
The composition according to the invention can be prepared by conventional methods.
Examples of contemplated combination therapies
The methods and pharmaceutical compositions of the invention include methods wherein the compounds according to the invention are the only active ingredient administered to a recipient animal. However, it is contemplated that the methods and pharmaceutical compositions also include combination therapies in which the compound is administered in combination with one or more other pharmaceutically acceptable active ingredients. The further active ingredient may be, for example, one or more further compounds according to the invention or one or more further compounds corresponding to the use according to the invention. Alternatively (or additionally), the other active ingredient may be one or more pharmaceutically acceptable compounds other than the compounds according to the invention or a compound corresponding to the use of the invention. Other active ingredients may be directed against the same and/or different parasites and conditions.
Contemplated active ingredients that may be administered in combination with the compounds include, for example, pharmaceutically acceptable anthelmintics, insecticides and acaricides, insect growth regulators, anti-inflammatory agents, anti-infective agents, antiprotozoal agents, hormones, dermal agents (e.g., bactericides and disinfectants), and immunological biologicals (e.g., vaccines and antisera) for disease prevention.
In one embodiment of the present description, an arylpyrazole compound such as phenylpyrazole may be included in the veterinary compositions of the present description. Arylpyrazoles are known in the art and may be suitable for combination with the compounds of formula (I) in the compositions of the specification. Examples of such arylpyrazole compounds include, but are not limited to, U.S. patent No. 6,001,384;6,010,710;6,083,519;6,096,329;6,174,540;6,685,954,6,998,131 and 7,759,381 (all of which are incorporated herein by reference). A particularly preferred arylpyrazole active agent is fipronil.
In another embodiment, the compositions of the present description may advantageously comprise one or more isoxazoline compounds known in the art. The isoxazoline active drug has high potency against a variety of ectoparasites and combination with the compound of formula (I) will expand the range of potency against these parasites.
Particularly useful isoxazoline active agents that can be combined with the compounds include afoxolaner (including substantially pure active enantiomer), sarolaner, fluralaner (including substantially pure active enantiomer), and lotilaner.
US patent No. 7,964,204, US 2010/0254960, al, US2011/0159107, US2012/0309620, US2012/0030841, US2010/0069247, WO 2007/125984, WO 2012/086462, US patent No. 8,318, 757, 8,466,115, 8,618,126, 8,822,466, 8,383,659, 8,853,186, 9,221,835, US 2011/0144349, US patent No. 8,053,452; US 2010/0137412, US patent No. 8,410,153, US 2011/152081, WO 2012/089623, WO 2012/089622, US patent nos. 8,119, 671;7,947,715; WO 2102/120135, WO 2012/107533, WO 2011/157748, US 2011/0245274, US 2011/0245463, US 2012/023296, US 2012/007765, US 2012/0035122, US 2011/0251247, WO 2011/154433, WO 2011/154434, US 2012/023817, US 2011/0166193, WO 2011/104088, WO 2011/104087, WO 2011/104089, US 2012/015946, US 2009/0143410, WO 2007/123855A2, US 2011/01018212, US patent No. 7,951,828& US patent No. 7,662,972, US 2010/01375372 Al, US 2010/0179194 A2, US 2011/0086886 A2, US 2011/00599 Al, US 2010/0179195 Al, US 2015/012623, WO 2010/003923, WO 2010/003877, WO 2010/003602, WO 2015/2014/20152, WO 2015607228, WO 20135 and WO 20135 are all incorporated herein by reference.
Another combination partner is 2-chloro-N- (1-cyanocyclopropyl) -5- [1- [ 2-methyl-5- (1, 2-pentafluoroethyl) -4- (trifluoromethyl) pyrazol-3-yl ] pyrazol-4-yl ] benzamide (CAS RN 1621436). This compound is known as tigollan.
In another embodiment, the compositions of the present disclosure may advantageously comprise one or more SLO-1 modulator compounds known in the art. SLO-1 modulator active agents are highly active against a variety of parasites and combination with compounds of formula (I) will expand the range of efficacy against these parasites. Particularly useful SLO-1 modulator active agents that may be combined with the compounds include the compounds disclosed in WO2017/178416, WO2018/087036, WO2018/197401, WO2019/002132, WO2019/025341, WO2019115768, WO2019/215182, WO2020/14068, WO2020/131629, WO2020/131631 and WO2020/083971, all of which are incorporated herein by reference in their entirety.
In another embodiment, the compositions of the present disclosure may advantageously comprise one or more SLO-1 depsipeptide compounds known in the art. SLO-1 depsipeptide active agents are highly effective against a variety of parasites, and combination with a compound of formula (I) will expand the range of efficacy against these parasites. Particularly useful SLO-1 depsipeptide active agents that may be combined with the compound include the compounds disclosed in WO2019/108591, WO 2019/217459, WO2016/187534, WO2017/116702, WO2018/093920, WO 1996/01945, WO 1995/007472, WO1994/019334, WO1993/019053, WO2014/089053, WO2018/187173, WO2013/187480, WO2015/093558, WO2012/077783, WO1997/002256, WO1997/011064, U.S. patent No. 5624897, WO1997/020547, AU2002/226415, JP03207870, DE594082812, all of which are incorporated herein by reference in their entirety.
The invention therefore also relates to the use of a combination comprising a) one or more compounds of the formula (I) according to the invention or one of the compounds, and b) one or more pharmaceutically acceptable active compounds which differ in structure from component a) as a medicament.
The active compound b) is preferably an anthelmintic compound, more preferably selected from SLO-1 depsipeptide compounds and SLO-1 modulators as described above, avermectins (e.g. ivermectin, siramectin, doramectin, avermectin and eplericin); milbemycins (moxidectin and Mi Erbi mycin oxime); pre-benzimidazoles (e.g., febantel, netoby amine, and thiophanate); benzimidazole derivatives, such as triclabendazole or thiazole benzimidazole derivatives (e.g. thiabendazole and candidazole) or carbamate benzimidazole derivatives (e.g. fenbendazole, albendazole (oxide), toldazole, oxfendazole, panbendazole, oxybenzozole, flubendazole); imidazothiazoles (e.g., levamisole and tetraimidazole); tetrahydropyrimidines (morantel and thiopyrimidine), organophosphates (e.g., trichlorfon, dermatopontin, dichlorvos, and napeptidphos); salicylanilides (e.g., clofentanyl, hydroxychlorozamide, rafoxanide, and niclosamide); nitrophenol compounds (e.g., nitrophenol nitrile and nitro thiocyanate); benzene disulfonamides (e.g., clorsulon); pyrazinoisoquinolines (e.g., praziquantel and exenatide); heterocyclic compounds (e.g., piperazine, ethanamine, dichlorophen, and phenothiazine); arsenicals (e.g., thioacetarsolamine, melorsamine, and thioacetarsolamine); cyclic octadepsipeptides (e.g., emodepside); paraherquamides (e.g., derquantel); and aminoacetonitrile compounds (e.g., monetel, AAD 1566); triphenyldiamidine (amidine compound); amidine compounds (e.g., amitraz and benzodiamidine) include all pharmaceutically acceptable forms, such as salts, solvates, or N-oxides.
Preferred combinations include a) a compound selected from the group of compounds of formula (I) as defined elsewhere in the specification, suitably compounds 1 to 480 (or enantiomers, salts, solvates, N-oxides or prodrugs thereof) in the table, and b) a compound selected from the group consisting of: anthelmintic avermectins (e.g., ivermectin, siramectin, doramectin, avermectin, and eplericin); milbemycins (moxidectin and Mi Erbi mycin oxime); pre-benzimidazoles (e.g., febantel, netoby amine, and thiophanate); benzimidazole derivatives such as thiazole benzimidazole derivatives (e.g., thiabendazole and candidazole), carbamate benzimidazole derivatives (e.g., fenbendazole, albendazole (oxide), mebendazole, oxfendazole, panbendazole, oxbendazole, flubendazole and triclosazole); imidazothiazoles (e.g., levamisole and tetraimidazole); tetrahydropyrimidines (morantel and thiopyrimidine), organophosphates (e.g., trichlorfon, dermatopontin, dichlorvos, and napeptidphos); salicylanilides (e.g., clofentanyl, hydroxychlorozamide, rafoxanide, and niclosamide); nitrophenol compounds (e.g., nitrophenol nitrile and nitro thiocyanate); benzene disulfonamides (e.g., clorsulon); pyrazinoisoquinolines (e.g., praziquantel and exenatide); heterocyclic compounds (e.g., piperazine, ethanamine, dichlorophen, and phenothiazine); arsenicals (e.g., thioacetarsolamine, melorsamine, and thioacetarsolamine); cyclic octadepsipeptides (e.g., emodepside); paraherquamides (e.g., derquantel); and aminoacetonitrile compounds (e.g., monetel, AAD 1566); triphenyldiamidine (amidine compound); and amitripter (amidine compounds), including all pharmaceutically acceptable forms, such as salts.
Preferred combinations comprise at least one compound selected from the group consisting of compounds of formula (I) as defined elsewhere in the specification, suitably compounds 1 to 480 of the table, and
avermectin, ivermectin, emamectin, eplericin, doramectin, moxidectin, mi Erbi mycin oxime; or alternatively
Chlorthalidomide, hydroxychlorozamide, rafoxanide, niclosamide; or alternatively
Nifiophenol nitrile, nitro-thiocyanate, chlorsultone; or alternatively
Praziquantel, exenatide; or alternatively
Emodepside, derquantel, monetel.
The compounds described herein may be combined with a pharmaceutically acceptable insecticide or acaricide. Such pharmaceutically acceptable insecticides and acaricides include, for example, acetamiprid, acetylchlorfenapyr, amitraz, sulfametofen, abamectin, azadirachtin, bifenthrin, bifenazate, buprofezin, bistrifluron, chlorfenapyr, chlorpyrifos, benfurazamine, clothianidin, chlorfenamide, cyflumetofen, beta-cyhalothrin, lambda-cyhalothrin, fenhexamine cypermethrin, cyromazine, deltamethrin, dimetryn, diafenthiuron, diazinon, diflubenzuron, tebufenpyrad, dinotebufenpyrad, emamectin, homofenvalerate, ethiprole, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrin, tau-flufenoxuron, halofenozide, tebufenozide, dimetrex triflumuron, imidacloprid, indoxacarb, lufenuron, metaflumizone, methoprene, methomyl, methoxyfenozide, nitenpyram, novaluron, permethrin, fenphos, profenothrin, fenpropithrin, prafenpyrad, pymetrozine, pyrifos, pyrethrin, pyridalyl, prafluquinconazole, pyraclostrobin, pyriproxyfen, rotenone, minoxidil, spinetoram, spirodiclofen, spirotetramat, sulfoxaflor, tebufenozide, tebufenpyrad, thiamethoxam, tolfenpyrad, tetrabromothrin, isoxazoline and triflumuron as described above. General references discussing antiparasitic agents such as insecticides and acaricides include, for example, the Pesticide Manual,13th Edition,C.D.S.Tomlin,Ed, british Crop Protection Council, farnham, surrey, U.K. (2003).
The compounds described herein may be combined with pharmaceutically acceptable insect growth regulators. Such pharmaceutically acceptable insect growth regulators include, for example, methoprene, pyriproxyfen, tetrahydronimbin, chlorfluazuron, cyromazine, diflubenzuron, fluzouron, flufenoxuron, lufenuron, ifen uron, tebufenozide and triflumuron. These compounds tend to provide initial and sustained treatment of parasite infestations in all stages of insect development (including eggs) on animal subjects, as well as in the environment of animal subjects.
The compounds described herein may be combined with pharmaceutically acceptable antiprotozoal agents. Such pharmaceutically acceptable antiprotozoal agents include, for example, triazinetriones (e.g., toltrazuril and patoglitazone) and triazinediones (e.g., clazuril, diclazuril and letrozuril).
In some contemplated embodiments, the compound is administered with a pyridylmethylamine derivative, such as the pyridylmethylamine derivative discussed in European patent application EP0539588 or International patent application publication WO 2007/115643.
In some contemplated embodiments, the compound is administered with nodulisporic acid (nodulisporicacid) and derivatives thereof, e.g., U.S. Pat. nos. 5,399,582;5,945,317;5,962,499;5,834,260;6,221,894; or 5,595,991; or the compounds discussed in WO 1996/29073.
In some contemplated embodiments, the compound is administered with a dihydroazole (dihydroazole) compound, such as the compound discussed in WO 2010/75591.
Other antiparasitic compounds contemplated for use in combination therapy with the compounds include, for example, imidazo [1,2-b ] pyridazine compounds discussed in U.S. patent application publication No. 2005-0182059; 1- (4-mono-and di-halomethylsulfonylphenyl) -2-amido-3-fluoropropanol compounds discussed in U.S. patent 7,361,689; the triflylanilide oxime ether compounds discussed in us patent 7,312,248; n- [ (phenoxy) phenyl ] -1, 1-trifluoromethanesulfonamide and n- [ (phenylsulfanyl) phenyl ] -1, 1-trifluoromethanesulfonamide compounds discussed in U.S. patent application publication 2006-0281695; and 2-phenyl-3- (1H-pyrrol-2-yl) acrylonitrile compounds discussed in U.S. patent application publication 2006/0128779; the isoxazoline compounds discussed in WO patent application publications 2005-085216, WO 2007/026965, WO 2007/070606, WO 2007/075459, WO 2007/079162, WO 2007/105814, WO 2007/125984, WO 2008/019760, WO 2008/122375, WO 2008/150393, WO 2009/002809, WO 2009/003075, WO 2009/022746, WO 2009/035004, WO 2009/045999, WO 2009/051956, WO 2009/035004.
In contemplated combination therapies, the compounds according to the invention may be administered before, simultaneously with and/or after the other active ingredients. In addition, the compounds according to the invention can be applied in the same composition as the other active ingredients and/or in a composition separate from the other active ingredients. Furthermore, the compounds according to the invention and the other active ingredients may be administered by the same and/or different routes of administration.
When the compounds according to the invention are administered in a combination therapy, the weight ratio of the active ingredients can vary widely. Factors affecting this ratio include, for example, the particular compound; identity of other active ingredients administered in combination therapy; routes of administration of the compounds and other active ingredients; conditions and pathogens of interest; the type (e.g., species and breed) of animal, age, size, sex, diet, activity, and condition; as well as pharmacological considerations such as the activity, efficacy, pharmacokinetics and toxicological profile of the compounds and other active ingredients. In some contemplated embodiments, for example, the weight ratio of the compound to the other active ingredients is, for example, from about 1:3000 to about 3000:1. In some such cases, the weight ratio is about 1:300 to about 300:1. In other such cases, the weight ratio is from about 1:30 to about 30:1.
It is contemplated that such compounds may be administered with one or more other compounds that beneficially affect (e.g., enhance or prolong) the activity (or other characteristics, such as safety) of the compound, among other active ingredients. For example, it is contemplated that the compound may be administered with one or more potentiators, such as Piperonyl Butoxide (PBO) and triphenyl phosphate (TPP).
The invention also relates to a kit suitable for carrying out the above-described method of treatment, for example. The kit comprises a therapeutically effective amount of one or more compounds of the invention and additional components. The additional component may be, for example, one or more of the following: another ingredient (e.g., an excipient or active ingredient), a device or diagnostic tool for combining a compound of the invention with another ingredient, and/or for administering a compound of the invention.
The compounds used according to the invention exhibit excellent activity in the treatment of parasitic infestations and are additionally acceptable for the animals treated.
The following table sets forth suitable compounds of the present invention. If racemates are indicated, but only one stereoisomer is depicted, the other stereoisomer is also included.
The following compounds are very suitable for use in the process of the invention:
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Examples
The following compounds were prepared.
The compounds were synthesized according to the methods as described in WO2016168059 and WO2018073127
See Table 1, below
TABLE I
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The structures of compounds 1-480 are shown in FIG. 4. If racemates are indicated, but only one of the stereoisomers is depicted, the other stereoisomer is also intended to be depicted.
In vitro test-ectoparasites
Example 1: tick larva contact test
Tick larvae (rhipicephalus) were immersed in decreasing concentrations of test compound (dissolved in DMSO-emulsifier-deionized water mixture) for about 3 minutes. Tick inhibition was assessed about 24 hours after contact exposure (damage +% dead ticks per test concentration). The viability of the parasites used was verified in the negative control group (i.e. untreated control and solvent control).
Results: at a test concentration of 388. Mu.M, compounds with an activity of > 80% inhibition were active.
(. Times.represents a compound whose activity is > 80% inhibited at a test concentration of 49. Mu.M)
Compounds 1, 3, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 30, 35, 39, 50, 51, 55, 59, 61, 63, 64, 65, 80, 87, 88, 89, 90, 91, 92, 94, 95, 99, 101, 107, 113, 114, 115, 117, 120, 126, 136, 137, 140, 145, 147, 151, 152, 160, 183, 165, 168, 170, 173, 185, 203, 207, 199, and 197.
The compounds with a tick activity > 80% inhibition at a test concentration of 25 μm were active, i.e.:
compounds 4, 19, 37, 51, 55, 56, 59, 63, 64, 65, 80, 87, 90, 91, 95, 99, 100, 114, 136, 145, 147, 149, 150, 160, 170, 173, 179, 185, 197, 209, 212, 215, 216, 221, 225, 227, 230, 252, 264, 265, 278, 281, 283, 284, 289, 292, 294, 302, 309, 310, 313, 321, 331, 333, 335, 352, 376, 379, 386, 423, and 432.
The compounds with tick activity > 80% inhibition at the test concentration of 100ppm were active, i.e.:
compounds 1, 2, 3, 4, 5, 6, 7, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 35, 37, 46, 49, 50, 51, 55, 56, 59, 63, 64, 65, 69, 80, 81, 86, 87, 88, 89, 90, 91, 95, 99, 100, 101, 107, 113, 114, 115, 126, 136, 145, 147, 149, 150, 160, 169, 171, 173, 179, 183, 184, 185, 197, 200, 203, 209, 212, 213, 215, 216, 220, 221, 223, 225, 227, 230, 233, 252, 264, 265, 281, 283, 284, 289, 292, 294, 302, 309, 310, 313, 321, 331, 352, 376, 379, 386, 432, 469, 470, 471, 475, 473, 478, 480, 479, and 479.
Example 2: flea contact test
Adult fleas (Chlamydomonas catus) are exposed to filter papers impregnated with decreasing concentrations of test compounds (dissolved in the DMSO-emulsifier-deionized water mixture). After a continuous contact time of about 48 hours, the inhibition (percent of dead + injured fleas per concentration tested) was evaluated. The viability of the parasites used was confirmed in the negative control group (i.e. untreated control and solvent control).
Results: the compounds that inhibit the flea activity by 80% or more at the test concentration of 1000ppm are active, namely: compounds 55, 65, 90, 91, 99, 100, 114, 115, 145, 147, 179, 185, 197, 289, 469, 470, 471, 472, 473, 474, 477 and 479.
Example 3: tick feeding test
Tick nymphs (stage III, blooming ticks) were raised on artificial membranes and blood was spiked with decreasing concentrations of test compound (dissolved in DMSO-emulsifier-blood mixture). The raised nymphs were incubated for about 2-3 weeks to allow the ticks to molt into the next stage. Inhibition of ticks (i.e., injury + dead ticks per test concentration ecdysis-evaluation) was assessed. The viability of the parasites used was confirmed in the negative control group (i.e. untreated control and solvent control).
Results: compounds whose tick activity is > 80% inhibited at a test concentration of 1ppm are active, namely: compounds 1, 2, 3, 4, 5, 6, 7, 8, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 469, 470, 471, 472, 473, 474, 475, 477, 478, 479, and 480.
Example 4: flea feeding test
Adult fleas of defined ages (Chlamydia felis) were fed onto the artificial membranes and blood was spiked with decreasing concentrations of test compound (dissolved in the DMSO-emulsifier-blood mixture). Inhibition of fleas (i.e., death +% injured fleas per concentration tested) was assessed after approximately 48 hours of continuous feeding. The viability of the parasites used was confirmed in the negative control group (i.e. untreated control and solvent control).
Results: it was found that compounds which inhibit greater than or equal to 80% of flea activity at the test concentration of 1ppm were active, namely: compounds 4, 15, 18, 19, 20, 21, 23, 24, 25, 64, 65, 80, 81, 86, 87, 88, 89, 90, 91, 95, 99, 100, 115, 145, 149, 150, 160, 173, 179, 183, 184, 185, 197, 200, 203, 209, 212, 213, 220, 221, 223, 227, 230, 252, 265, 278, 281, 289, 309, 313, 321, 331, 333, 335, 352, 376, 379, 386, 423, 432, 469, 470, 471, 472, 473, 474, 475, 477, 478, 479 and 480.
Example 5: fly larvae contact/feeding test
I (microcystis aeruginosa) was grown in medium spiked with decreasing concentrations of test compound (dissolved in DMSO-emulsifier-deionized water mixture). After a continuous exposure time of about 48 hours, the inhibition (%) of the development of fly larvae was evaluated. The viability of the parasites used was confirmed in the negative control group (i.e. untreated control and solvent control).
Results: the compounds found to be more than or equal to 80% inhibited in fly larvae activity at the tested concentration of 100ppm were active, namely: compounds 3, 4, 5, 6, 8, 14, 18, 19, 20, 21, 26, 46, 49, 50, 51, 55, 56, 59, 63, 64, 65, 69, 80, 81, 86, 87, 88, 90, 91, 95, 99, 100, 101, 107, 113, 114, 115, 136, 145, 147, 149, 150, 169, 171, 173, 179, 183, 184, 185, 197, 200, 203, 209, 212, 213, 215, 216, 220, 221, 223, 227, 230, 233, 252, 264, 265, 278, 281, 284, 289, 294, 309, 310, 313, 321, 331, 335, 352, 376, 379, 386, 423, 432, 469, 470, 471, 472, 473, 474, 475, 476, 477, 478, 479, and 480.
Example 6: young sea lice contact test
The copepodites (juvenile sea lice stage of Lepeophtheirus salmonis) were exposed to seawater incorporating decreasing concentrations of test compound (dissolved in DMSO sea water mixture). After a continuous exposure of about 24 hours, sea lice inhibition (death +% of damaged copepodites) was assessed. The viability of the parasites used was confirmed in a negative (solvent) control group.
Results: at a test concentration of 100nM, the following compounds showed inhibition of ≡80% (representing 100% inhibition): compounds 1, 4, 11, 27, 29, 48, 51, 63, 68, 70, 96, 98, 109, 111, 112, 124, 132, 187, 188, 189, 190, 218, 454, 328, 331, 335, 342, 347, 355, 364, 367, 369, 370, 371, 373, 375, 377, 386, 405, 432, 439, 461, 465, 467, 470, 473, 474, 480.
Furthermore, the following compounds showed ≡80% inhibition (×100% inhibition) at a test concentration of 10 nM: compound 9, 86, 89, 447, 449, 455, 456, 457, 458, 459, 460, 464, 469, 471, 472, 475, 477, 478, 479.
Furthermore, the following compounds showed ≡80% inhibition (×100% inhibition) at 1nM test concentration: compounds 197, 446, 451, 453, 463.
Example 7: adult sea lice contact test
The movement phase of sea lice (i.e., pupation, adults of Lepeophtheirus salmonis) was exposed to sea water incorporating decreasing concentrations of the test compound (dissolved in PEG sea water mixture). Sea lice inhibition (% of death+damage sea lice) was assessed after about 1 hour and 24 hours of continuous exposure compared to the negative (solvent) control group.
Results: EC of the following compounds 50 >10 nM.ltoreq.25 nM: compounds 4, 9, 197, 449, 464, 465.
In addition, EC of the following compounds 50 Less than or equal to 10nM: compounds 8, 86,89、446、447、451、453、454、455、456、457、458、459、460、463、466、469、471、473、474、475、477、478、479、480。
Example 8: adult Caligus rogercresseyi sea lice contact test
The movement phase of sea lice (i.e., pupation, adults of Caligus rogercresseyi) was exposed to seawater incorporating decreasing concentrations of test compound (dissolved in PEG seawater mixture). Sea lice inhibition (% of death+damage sea lice) was assessed after about 1, 24 and 48 hours of continuous exposure compared to negative (solvent) and untreated control groups.
Results: EC of Compound 453 50 0.072ppb after 24 hours and 0.035ppb after 48 hours.
Example 9: tick larva resistance assay
The tick resistance assay (i.e., larval immersion test, LIT) was performed using larvae of several micropin tick isolates with known resistance characteristics (i.e., complete sensitivity; resistance to Di's reagent, coumaphos, DDT, chlorpyrifos, cyhalothrin, cypermethrin, amitraz, acetamiprid).
Tick larvae (rhipicephalus micropus) were immersed in the test compound solution for about 3 minutes. Tick mortality was assessed about 24 hours after contact. The viability of the parasites used was confirmed in the negative control group (i.e. untreated control and solvent control).
Results: compounds 446 and 197 were equally effective against sensitive isolates as compared to all multi-drug resistant isolates tested.
Example 10: sea lice resistance test
Sea lice resistance tests were performed using the mobile sea lice stage (i.e., pupated, adult) with several Lepeophtheirus salmonis isolates having known resistance characteristics (i.e., complete sensitivity, p-methylparaben (OP), emamectin benzoate (ML), deltamethrin (SP)). Sea lice are exposed to seawater incorporating a decreasing concentration of the test compound (dissolved in the PEG 300/sea water mixture). Sea lice inhibition (% of death+damage sea lice) was assessed after sustained exposure for about 1, 24 and 48 hours compared to the negative (solvent) control group.
Results: compound 453 was sensitive to isolates (EC after 24 hours 50 1.20ppb, 0.29ppb after 48 hours) and multiple resistant isolates (EC after 24 hours 50 1.96ppb, 0.64ppb after 48 hours).
In vivo analysis-ectoparasites
Example 11: guinea pig-efficacy against ticks/bed bugs of the Cryptorhizus family (argaside)
Prior to the day of treatment (day 0), guinea pigs were locally co-infested with young soft ticks (white-hairtail ticks) and bed bugs (temperate zone bed bugs) (use of the infestation device on the shaved skin area) to provide baseline-negative control values. Guinea pigs were treated orally (by gavage) or subcutaneously with a dose of 5mg/kg body weight of test compound in a formulation of 10% DMF/emulsifier +90% Aqua ad injectabilia.
Repeated local infestations of both parasites were performed at different time points after treatment. Ten saturated ticks and ten saturated bed bugs were collected within about 45 minutes after each infestation, and the percent of dead and injured parasites per species was estimated about 24 hours after collection. Efficiency was calculated as% inhibition of "kill+injury" parasites in the treatment group compared to baseline-negative control (using the modified Schneider Orelli's formulation).
Results: the activity of the test compounds at the different evaluation time points (. Gtoreq.80% inhibition was found to be active):
tick nymph-oral administration
Compounds 4, 51, 86, 89, 197, 446, 447, 449, 451, 453, 454, 455, 456, 460, 466, 469, 470, 471, 472 and 475 showed immediate activity on day 0.
Compounds 4, 51, 86, 197, 447, 451, 453, 466, 469, 470, 471 and 475 showed activity after 7 days.
Compounds 4, 86, 451, 453, 466, 469, 470, 471 and 475 showed activity after 10 days.
Compounds 4, 466, 470, 471 and 475 showed activity after 14 days.
Compounds 470, 471 and 475 showed activity after 17 days.
Compound 471 showed activity after 21, 24, 28, 31 and 35 days.
Tick nymph-subcutaneous administration
Compounds 4, 51, 86, 89, 197, 446, 447, 449, 451, 453, 454, 455, 456, 460, 466, 469, 470, 471, 472 and 475 showed immediate activity on day 0.
Compounds 4, 51, 86, 197, 446, 447, 449, 451, 453, 454, 466, 469, 470, 471 and 475 showed activity after 7 days.
Compounds 4, 51, 86, 197, 446, 447, 451, 453, 454, 469, 470, 471 and 475 showed activity after 10 days.
Compounds 4, 51, 446, 447, 469, 470, 471 and 475 showed activity after 14 and 17 days.
Compounds 470, 471 and 475 showed activity after 21, 24, 28 and 31 days.
Compounds 471 and 475 showed activity after 35 days.
Bed bug oral administration
Compounds 4, 51, 86, 89, 197, 446, 447, 449, 451, 453, 454, 455, 456, 460, 466, 469, 470, 471, 472 and 475 showed immediate activity on day 0.
Compounds 4, 51, 86, 197, 446, 447, 451, 453, 460, 466, 469, 470, 471 and 475 showed activity after 7 days.
Compounds 4, 86, 451, 453, 466, 469, 470, 471 and 475 showed activity after 10 days.
Compounds 4, 466, 470, 471 and 475 showed activity after 14 days.
Compounds 466, 470, 471 and 475 showed activity after 17 days.
Compounds 470, 471 and 475 showed activity after 21, 24 and 28 days.
Compound 471 showed activity after 31 and 35 days.
Bed bug subcutaneous administration
Compounds 4, 51, 86, 89, 197, 446, 447, 449, 451, 453, 454, 455, 456, 460, 466, 469, 470, 471, 472 and 475 showed immediate activity on day 0.
Compounds 4, 51, 86, 197, 446, 447, 451, 453, 460, 466, 469, 470, 471 and 475 showed activity after 7 days.
Compounds 4, 51, 86, 197, 446, 447, 451, 453, 466, 469, 470, 471 and 475 showed activity after 10 days.
Compounds 4, 51, 446, 466, 469, 470, 471 and 475 showed activity after 14 and 17 days.
Compounds 446, 469, 470, 471 and 475 showed activity after 21 days.
Compounds 446, 470, 471 and 475 showed activity after 24 days.
Compounds 470, 471 and 475 showed activity after 28 and 31 days.
Compounds 470 and 471 showed activity after 35 days.
Conclusion: the compounds show efficacy against both parasites and are generally well tolerated in guinea pigs.
Compounds 4, 86, 451, 453, 466, and 469 were 100% effective against ticks and bed bugs using both routes of administration at least until day 10.
Compound 4, 470, 471, 475 was 100% effective for control ticks and bed bugs for at least one week using both routes of administration.
Subcutaneous administration resulted in longer duration of efficacy of compounds 4, 51, 197, 446, 447, 454 and 455.
Example 12: dog-anti-tick/flea efficacy
Two days prior to the treatment day (day 0), the beagle dogs (whole body) were infested with 80 cat Chlamydia and 50 red or oval ticks (Haemaphysalis elliptica) (sex ratio 1:1) and thereafter the infestations were repeated. Dogs in the treatment group were treated orally (compound weighed in gelatin capsules), topically (spray-drop, DMA 92%/DEET 8%) or subcutaneously (PEG 200%/water for injection 10%) with 10mg/kg body weight of test compound. Dogs of the negative control group received only empty gelatin capsules orally and received the spray-drip formulation vehicle topically.
The evaluation of efficacy in the treatment group was performed by counting live ticks/fleas on dogs about 48 hours after the power treatment (evaluation of therapeutic effect) or 48 hours after each post-treatment infestation (evaluation of prophylactic effect) compared to the live parasite count in the negative control group (efficacy calculation using Abbott's formula). The compounds with efficacy of 80% or more were found to be active.
Tick oral administration
Compounds 4, 197, 453 and 466 were active (therapeutic efficacy) on day 2.
Compound 466 was active until day 16. Compound 453 was active until day 70. Compound 197 was active until day 198.
Tick-topical application
Compounds 453 and 466 were active (therapeutic efficacy) on day 2.
Compound 466 was active up to day 30. Compounds 197 and 453 were active up to day 70/72.
Tick-subcutaneous administration
Compound 4 was active (therapeutic efficacy) on day 2.
Compound 4 was active until day 16.
Flea oral administration
Compounds 4, 197, 453 and 466 were active (therapeutic efficacy) on day 2.
Compounds 453 and 466 were active up to day 70. Compound 197 was active until day 227.
Flea topical application
Compounds 197, 453 and 466 were active (therapeutic efficacy) on day 2.
Compounds 453 and 466 were active up to day 70. Compound 197 was active until day 100.
Flea subcutaneous administration
Compound 4 was active (therapeutic efficacy) on day 2.
Compound 4 was active until day 86.
Conclusion: the compounds have both therapeutic and prophylactic effects on fleas and ticks. They are generally well tolerated in dogs. Compounds 4, 197, 453 and 466 showed therapeutic efficacy against fleas and ticks in dogs.
Compounds 466, 197 and 453 showed prophylactic efficacy against fleas for at least 10 weeks on topical and oral administration.
Compounds 197 and 453 showed prophylactic efficacy against fleas and ticks for at least 10 weeks on topical and oral administration.
Example 13: efficacy against single host ticks by cattle
Up to 3000 infestation of the larvae of rhipicephalus micropus are carried out twice or three times per week on cattle (whole body) before and after the treatment day (day 0). The cattle of the treatment group were then treated subcutaneously or topically (spray or pour-on) at a dose of 1mg/kg body weight of the test compound. As subcutaneous formulations, 2-pyrrolidone 50%/Tween 80 50% or NMP 60%/PEG 300% was used. As topical formulations, spray solutions (DMF/emulsifier 2%/tap water 98%) (compound 4) or DMA 92%/DEET 8% pour-on solutions (all other compounds) or pour-on solutions containing Imwitor988 (20%) +migllol 840 (QS) (compound 453 and compound 466) or migllol 840 (QS) (compound 453) were used. Cattle of the negative control group received only the formulation excipients of the corresponding route of administration.
Female ticks that fallen from cattle that were fully saturated with blood were collected daily after treatment and counted in the treatment and control groups. Efficacy was expressed using standard ADEQ analysis methods (ADEQ calculation is according to the WAAVP guidelines for evaluating efficacy against ticks on ruminants; veterinary parasitics 136 (2006) 29-43). The potent compounds were found to be active/potent. Onset refers to the first day when the efficacy is greater than or equal to 80%. Efficacy duration refers to the last day of efficacy of 80% or more.
Results: the efficacy of the test compounds at the various evaluation time points is as follows:
compound 4-onset of action on day 3 post-topical administration and day 2 post-subcutaneous administration.
Compound 446-onset on day 3 after topical administration.
Compound 447-was onset of action on day 4 after topical application.
Compound 197-onset on day 2 after topical administration and day 3 after subcutaneous administration.
Compound 453-was effective after topical administration (DMA 92%/DEET 8% pour-on solution) and subcutaneous administration on day 3.
Compound 453 formulated as a pour-on in Imwitor 988+miglyoyl 840-the topical formulation was active on day 1.
Compound 453 formulated as a pour-on in Miglyol 840-was effective on day 2 post-topical formulation.
Compound 466 formulated as a pour-on in Imwitor 988+Miglyol 840-onset of action on day 1 after topical application
Compound 4-duration of efficacy after topical application until day 58 (spray solution: DMF/emulsifier 2%/tap water 98%) and after subcutaneous application until day 38.
Compound 446-after topical application until day 47.
Compound 447-duration of efficacy at least until day 57 after topical application.
Compound 197-duration of efficacy after topical administration until at least day 47 and after subcutaneous administration until day 120.
Compound 453-duration of efficacy after topical application until day 63 and after subcutaneous application until day 82.
Compound 453 formulated as pour-on in Imwitor 988+miglyoyl 840-duration of efficacy up to day 77.
Compound 453 formulated as a pour-on in Miglyol 840-duration of efficacy up to day 84.
Compound 466 formulated as a pour-on in Imwitor 988+miglyoyl 840-duration of efficacy up to day 87.
Conclusion: the compounds showed therapeutic (against existing infestations) and prophylactic (against re-infestations) effects on bovine single host ticks. They are generally well tolerated in cattle.
Example 14: bovine-efficacy against multi-host ticks
Cattle are treated subcutaneously or topically (pour-on) at a dose of 5mg/kg body weight of test compound (day 0). As subcutaneous formulation, NMP 60%/PEG 300% was used, and as pour-on formulation, DMA 92%/DEET 8% was used. Cattle of the negative control group received only two formulation excipients of the formulation (SC, pour-on).
Cattle were locally infested with 30-40 additional raised rhipicephalus and adult ticks (Dermacenter variabilis) of the variant leather ticks (1:1 for both species sex ratio), each, by placing ticks at ear loops (additional rhipicephalus) or knitted patches (variant leather ticks) attached to the body side at different points in time before and after treatment. Free (i.e., non-adherent ticks) were removed from the ear muff/knitted patch two days after each intrusion and excluded from efficacy calculations.
Efficacy (for both tick substances) was assessed by comparing the number of live ticks collected from cattle in the treatment group with the number of live parasites in the negative control group (efficacy calculation using Abbott's formula) for two days after treatment (evaluation of prophylactic efficacy) or three days after each post-treatment infestation (evaluation of therapeutic efficacy). Compounds with efficacy of 80% or more were found to be active.
Results:variant leather tick-topical application
Compounds 197, 446, 447 and 453 showed therapeutic efficacy on day 2.
Compounds 197, 446, 447 and 453 showed prophylactic efficacy at re-infestation after 7 days.
Compounds 197, 446 and 453 showed prophylactic efficacy at re-infestation after 14 days.
Compounds 197, 446 and 453 showed preventive effects at re-infestation after 21 days.
Compounds 446, 447 and 453 showed prophylactic efficacy when re-infested after 28 days.
Compounds 446 and 453 showed prophylactic efficacy at re-infestation after 35 days.
Dermapyrifos variant subcutaneous administration
Compounds 197, 446, 447 and 453 showed therapeutic efficacy on day 2.
Compounds 197, 446, 447 and 453 showed prophylactic efficacy at re-infestation after 7 days.
Compounds 197, 446 and 453 showed prophylactic efficacy at re-infestation after 14 days.
Compounds 197, 446 and 453 showed prophylactic efficacy at re-infestation after 21 days.
Compounds 197, 446, 447 and 453 showed prophylactic efficacy at re-infestation after 28 days.
Compound 453 showed prophylactic efficacy at re-infestation after 35 days.
Additional rhipicephalus topical application
Compounds 197, 447 and 453 showed therapeutic efficacy on day 2.
Compounds 197, 446, 447 and 453 showed prophylactic efficacy at re-infestation after 7 days.
Compounds 197, 446, 447 and 453 showed prophylactic efficacy at re-infestation after 14 days.
Compounds 197, 446 and 453 showed prophylactic efficacy at re-infestation after 21 days.
Compounds 197, 446, 447 and 453 showed prophylactic efficacy at re-infestation after 28 days.
Compounds 197, 447 and 453 showed prophylactic efficacy at re-infestation after 35 days.
Additional rhipicephalus-subcutaneous administration
Compounds 197, 446, 447 and 453 showed therapeutic efficacy on day 2.
Compounds 197, 446 and 453 showed prophylactic efficacy at re-infestation after 7 days.
Compounds 197, 446 and 453 showed prophylactic efficacy at re-infestation after 14 days.
Compounds 197, 446, 447 and 453 showed prophylactic efficacy at re-infestation after 21 days.
Compounds 197 and 453 showed prophylactic efficacy when re-infested after 28 days.
Compounds 197 and 453 showed prophylactic efficacy at re-infestation after 35 days.
Conclusion: the compounds show therapeutic and prophylactic efficacy against multi-host ticks on cattle. They are generally well tolerated in cattle.
Compounds 197, 447 and 453 were 100% effective in treating existing tick infestations using both routes of administration.
Example 15: salmon-in vivo efficacy against sea lice using intragastric administration:
salmon (Salmosalar) was orally treated once by gavage at 5mg/kg body weight/fish (day 0). As a formulation, DMSO 5%/fish oil 95% was used. Salmon of the negative control group received only the vehicle of the formulation.
The fish were infested with leptophtheirussalmons copepoda larvae twice before treatment (i.e., about day-28 and day-3) and once after treatment (i.e., day 17).
On day 7, the examination was performed under fish sedation, and the (pupated) adult sea lice on each fish were counted and removed (evaluation of the efficacy of the (pupated) adult sea lice treatment since day-28 infestation).
On about day 28 (at the end of the animal phase), the fish were sacrificed and sea lice on each fish were classified ((pupated) adult or juvenile) and counted. The number of (pre-) corresponds to The number of (pupated) adult or juvenile parasite stages at The respective infestation time point for The efficacy calculation, i.e. The evaluation of The efficacy of The treatment against juvenile sea lice from day-3 infestation and The evaluation of The preventive efficacy from day 17. Efficacy was expressed as% reduction in sea lice in the treated group relative to the control group using the Abbott formula.
Results: the therapeutic effect of the following compounds on (pupated) adult sea lice is greater than or equal to 80% (xrepresents 100% efficacy): compounds 86, 89, 197, 449, 451, 453, 459, 460.
86*、89*、197、449、451、453*、455*、456、457、458*、459*、460*、463*、464*、466、478*、479*、480*。
The therapeutic effect of the following compounds on young sea lice is greater than or equal to 80% (xrepresents 100% efficacy): compound 86, 89, 449, 459, 460.
86*、89*、449、455*、456*、457*、458*、459*、460*、463*、464*、466、478、479、480*。
The prophylactic effect of the following compounds at day 17 re-infestation was ≡80% (xrepresents 100% efficacy): compound 453, 456, 458, 464.
Example 16: in vivo efficacy against sea lice administered in salmon-use feed
Four study groups of fish (one for assessing treatment efficacy and one for assessing prophylactic efficacy and their corresponding controls). Commercial fish feed pellets were coated with formulated test compounds. As a formulation, DMSO 5%/fish oil 95% was used. Salmon (Salmosalar) was treated orally by coating feed at a mass of 1mg/kg fish for 7 consecutive days. Salmon of the negative control group received only feed coated with the vehicle of the formulation.
The fish of the treatment group were infested with leptophtheirussalmons twice (about day-28 and day-3) prior to treatment. On about day 8, fish were examined under sedation and each fish was counted for (pupated) adult sea lice and removed (the efficacy of treatment against (pupated) adult sea lice was assessed from day-28 infestations). On about day 25, the fish were sacrificed and adult sea lice on each fish (pupated) were counted (about day-3 of the infestation was evaluated for efficacy of treatment against young sea lice).
The fish of the prophylaxis group were infested at several time points spaced 2 weeks after treatment. The fish were evaluated for adult sea lice about 3 weeks after each re-infestation (pupation). At each evaluation, all (pupated) adult sea lice were removed from the fish. The preventive efficacy calculation was performed using the number of sea lice on fish corresponding to the respective re-infestation time points. Efficacy was expressed as% sea lice reduction in the treated group relative to the control group using the Abbott formula.
Results: for compound 453, the therapeutic efficacy on (pupated) adult sea lice and young sea lice reached 100%. The prophylactic effect was 100% (day 14), 99.9% (day 28) and 86.0% (day 42) for re-infestation after treatment.
Example 17 localized pour-on
All formulations were prepared by weighing the required amount of compound 453 or compound 466 into a volumetric flask and adding about 80% of solvent 1 and any additional solvents used or other additives used. The flask was then heated with stirring to a temperature of 50 to 80 ℃ until the solution was free of any visible solids, and then allowed to cool to room temperature. Finally, the remaining solvent 1 was added to the filling line (fill line) of the volumetric flask.
The following table shows all the compositions used in examples 18 to 20:
And (3) injection: the numbers in brackets are the weight percent of the component. The components in column 1 of solvent are QS of 100% composition.
Example 18
Composition a and composition B were each applied to 4-headed cattle and their blood concentration of compound 1 (compound 453) was monitored for more than 91 days. Figure 1 shows that compound 1 (453) does not require rapid solvent evaporation at the time of application to achieve good maximum absorption (Cmax) and total Absorption (AUC), in contrast to many commercially available topical solutions.
Figure 1 shows that the Cmax and AUC values are higher for the oily solution (composition a) than for the volatile solution (composition B).
Example 19
Compositions C, D, E and F were each applied to 4-headed cattle and their blood concentration of compound 453 was monitored for more than 2 days. The data in fig. 2 below supports the conclusion that no chemical permeation enhancers are needed. It is clear that while some of these have slightly higher absorption and Cmax values, none of these are significant improvements and are insufficient to affect the overall performance of the compound.
Figure 2 shows a comparison of the concentration of compound 453 in bovine blood without CPE (composition C) and with three different CPEs (compositions D, E and F), demonstrating that there is no significant improvement in the inclusion of any CPE.
Example 20
Cattle (whole body) infested twice or three times a week with up to 3000 micropin larvae before and after the treatment day (day 0). Cattle in the treatment group were treated topically (pour-on) with compositions G, H, I and J disclosed in example 1. Cattle of the negative control group received only the formulation excipients of the corresponding route of administration.
Female ticks that were completely saturated with blood falling from cattle were collected daily after treatment and counted in the treatment and control groups. Efficacy was expressed using standard ADEQ assay methods (ADEQ calculation was used to evaluate efficacy of acaricides against ticks on ruminants according to the WAAVP guidelines; veterinary parasitology 136 (2006) 29-43). Compositions with efficacy greater than or equal to 80% were found to be active/effective. Onset of action refers to the first day with an efficacy of 80% or more. Duration of efficacy refers to the last day of efficacy greater than or equal to 80%.
Figure 3 shows the duration of >90% efficacy against rhipicephalus similis and the onset of >90% efficacy against rhipicephalus similis.
Example 21
In vitro test of rain resistance
In addition to good absorption, the compositions according to the invention have high water resistance. After a 5% solution of compound 453 in Miglyol 840 was applied to rabbit fur and allowed to stand for 4 hours, the sample was immersed in water for 30 minutes. Thereafter, the weight was reduced by 4%, and the determination of the presence of compound 453 in water indicated that it was below the detection limit.
Comparative example:
compounds exhibiting activity in prior art plant protection but not in animal health parasite assays
Compounds have been tested in prior art documents WO 2016/1688059=d1 and WO 2018/071327=d2 against a range of plant protection agrochemical related parasites. It was surprisingly found that the various compounds from D1 and D2 which show activity in plant protection assays do not show activity against animal healthy parasites in example 1 above, which is the most sensitive in the assay. The following table shows the activity of the compounds in example 1 (with reference numbers in these prior art documents) which are inactive against animal health parasites and as described below in plant protection bioassays. In particular, as can be seen, these comparative compounds are described in the above A 1 -A 5 The ring formed is halogen-free.
Plant protection test
Bioassays for asparagus caterpillar (Spodoptera exigua), cabbage loopers (Trichoplusia ni) are two good indicator species for a wide variety of chewing pests in plant protection. Yellow fever mosquito (aedes aegypti) bioassays are indicator species of piercing insect pests, including blood-sucking insect pests.
Bioassays for asparagus caterpillar BAW (Spodopteraexigua) ("test a") and cabbage loopers (Trichoplusia ni)) ("test B")
Bioassay of BAW: bioassays for BAW were performed using a 128 Kong Yinshi tray assay. 1 to 5 second-age BAW larvae were placed in each well (3 mL) of a diet tray previously filled with about 1.5mL of artificial diet, to which 50 μg/cm had been applied 2 Is dissolved in 50 μl of a 90:10 acetone-water mixture) (to each of the eight wells) and then allowed to dry. The tray was covered with a transparent self-adhesive cover, vented to allow gas exchange, and maintained at 25 ℃ for five to seven days under 14:10 light-dark conditions. The percent mortality of the larvae in each well was recorded; the activity of the eight wells was then averaged. The results are shown in the following table.
Bioassay of CL: CL bioassays were performed using 128-well diet tray analysis. 1 to 5 second instar CL larvae were placed in each well (3 mL) of a tray previously filled with 1mL of artificial diet, to which 50. Mu.g/cm had been applied 2 Is dissolved in 50. Mu.l of a 90:10 acetone-water mixture) and then dried. The trays were covered with a transparent self-adhesive cover, vented to allow gas exchange, and maintained at 25 ℃ for five to seven days under 14:10 light-dark conditions. The percent larval death for each well was recorded; the activity of the eight wells was then averaged. The results were obtained using the following A&The B rating table is shown in the following table.
Bioassay ("test C") on yellow fever mosquito (aedes aegypti, AEDSAE).
A master plate containing 400. Mu.g of molecules (equivalent to 4000-ppm solution) dissolved in 100. Mu.L of dimethyl sulfoxide (DMSO) was used. The master plate of the assembled molecule contained 15 μl per well. To the plate 135. Mu.L of a 90:10 water/acetone mixture was added. The robot was programmed to dispense 15 μl of aspirant from the motherboard into an empty 96 Kong Jianban ("daughter" board). Each motherboard creates 6 repetitions ("daughter" boards). The created "daughter" boards were immediately infested with YFM larvae.
The day before the plates were treated, the mosquito eggs were placed in Milipore water containing liver powder to begin hatching (in 4g to 400 mL). After the "child" plates were created using robots, they were 5 infested with 220 μl of liver powder/larval mosquito mixture (about 1 day old larvae). After infestation of the panels with mosquito larvae, the panels were covered with a non-evaporative cover to reduce dryness. The plates were kept at room temperature for 3 days before fractionation. After 3 days, each well was observed and scored based on mortality. The following table shows the results using the test C rating table below.
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Claims (29)
1. A compound of formula (I)
And N-oxides, veterinarily acceptable acid addition salts, salt derivatives, solvates, ester derivatives, crystal polymorphs, isotopes, stereoisomers and tautomers thereof,
for use in a method of treating or controlling parasite infestations in an animal, wherein
A 1 Is CR (CR) 5 N=o or N;
A 2 is CR (CR) 6 N=o or N;
A 3 is CR (CR) 7 N=o or N;
A 4 is CR (CR) 8 N=o or N;
A 5 is CR (CR) 9 N=o or N;
wherein A is 1 、A 2 、A 3 、A 4 、A 5 Wherein no more than 3 of the N groups are N or n=o;
R 1 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 2 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 3 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 4 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And S- (halo) 5 ；
R 5 Selected from H, F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 6 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl group、CH(＝NO(C 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 7 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 8 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no (C) 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may be optionally substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
R 9 selected from F, cl, br, I, H, CN, CHO, NHOH, NO, NO 2 、OH、NH 2 、＝O、(C 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkylphenyl (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) Haloalkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 、(C 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Cycloalkenyl, (C) 3 -C 6 ) Cycloalkyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 1 -C 6 ) Alkyl ((C) 1 -C 6 ) Alkyl) (=no(C 1 -C 6 ) Alkyl), C (=no (C) 1 -C 6 ) Alkyl) (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl, C (=o) NH (C 1 -C 6 ) Alkyl, C (=o) nhphenyl, C (=o) O (C 1 -C 6 ) Alkyl, CH (=no (C) 1 -C 6 ) Alkyl), imidazolyl, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) alkyl-O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl) (C (=O) (C 1 -C 6 ) Haloalkyl), N ((C) 1 -C 6 ) Alkyl) (C (=O) O (C) 1 -C 6 ) Alkyl group, N ((C) 1 -C 6 ) Alkyl group 2 、N(C(＝O)O(C 1 -C 6 ) Alkyl group 2 N=ch-phenyl, NH ((C) 1 -C 6 ) Alkyl C (=O) (C 1 -C 6 ) Alkyl), NHC (=o) R 10 、N(C 1 -C 6 ) alkyl-C (=o) lR 10 、NH(C 1 -C 6 ) Alkyl, NH (C) 1 -C 6 ) Alkenyl, NH (C) 1 -C 6 ) Alkynyl, NH (C) 1 -C 6 ) Alkylphenyl, NH (S (O) 2 (C 1 -C 6 ) Alkyl), NH-C (=O) O (C 1 -C 6 ) Alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S (=ncn) ((C) 1 -C 6 ) Alkyl), S (C) 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (=ncn) ((C) 1 -C 6 ) Alkyl), S (O) (C 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, SCN, thiazolyl, thienyl and triazolyl,
wherein each of alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thiophenyl, and triazolyl may optionally be substitutedIs substituted with one or more substituents selected from the group consisting of: F. cl, br, I, CN, OH, NH (C) 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Alkyl, NH (C) 3 -C 6 ) Cycloalkyl CH 2 O(C 1 -C 6 ) Haloalkyl, NHCH 2 (C 3 -C 6 ) Cycloalkyl, NH 2 、NO 2 Oxo, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkyl, (C) 1 -C 6 ) Alkoxy and C (=o) O- (C) 1 -C 6 ) An alkyl group;
or R is 6 And R is 7 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 6 And R is 7 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
or R is 7 And R is 8 Together with the atoms to which they are attached, form a ring containing 5 or 6 atoms, wherein the ring-forming atoms are selected from the group consisting of: -CH 2 -、-CH＝、＝CH-、-N＝、＝N-、-NH-、-O-、-S(O)-、-S(O) 2 -and-S-, wherein R 7 And R is 8 The ring formed is optionally substituted with one or more substituents selected from the group consisting of: (C) 1 -C 3 ) Alkyl group F, cl, br, I, CN, NO 2 And = O;
R 10 selected from H, (C) 1 -C 6 ) Alkyl, C 3 -C 6 ) Cycloalkyl), (C 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) -alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy- (C) 1 -C 6 ) Haloalkyl, C 1 -C 6 ) Alkoxy- (C) 2 -C 6 ) -alkenyl, (C) 1 -C 6 ) Alkyl- (C) 3 -C 6 ) Ring(s)Alkyl, heterocycle, aryl and (C 1 -C 6 ) An alkylphenyl group;
R 11 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 12 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 13 Selected from H, F, cl, br, I, CN, NH 2 、NO 2 、CHO、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 、(C 1 -C 6 ) haloalkyl-S (O) 2 NH 2 And triazolyl;
R 14 selected from H, F, cl, br, I, CN, NH 2 、NO 2 、(C 1 -C 6 ) Alkyl, (C) 3 -C 6 ) Cycloalkyl, (C) 2 -C 6 ) Alkenyl group (C) 3 -C 6 ) Cycloalkenyl, (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Alkoxy, (C) 1 -C 6 ) Haloalkyl, (C) 3 -C 6 ) Halogenated cycloalkyl, (C) 2 -C 6 ) Haloalkenyl, (C) 3 -C 6 ) Halogenated cycloalkenyl (C) 1 -C 6 ) Haloalkoxy, S (C) 1 -C 6 ) Alkyl, S (O) (C 1 -C 6 ) Alkyl, S (O) 2 (C 1 -C 6 ) Alkyl, S (C) 1 -C 6 ) Haloalkyl, S (O) (C 1 -C 6 ) Haloalkyl, S (O) 2 (C 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) alkyl-S (O) 2 NH 2 And (C) 1 -C 6 ) haloalkyl-S (O) 2 NH 2 ；
R 15 Selected from H, (C) 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) Haloalkyl, (C) 1 -C 6 ) Alkoxy (C) 1 -C 6 ) Alkyl, C (=o) (C 1 -C 6 ) Alkyl and (C) 1 -C 6 ) Alkoxy C (=o) (C 1 -C 6 ) Alkyl group
H、(C 1 -C 6 ) Alkyl, (C) 2 -C 6 ) Alkenyl group (C) 2 -C 6 ) Alkynyl, (C) 1 -C 6 ) A haloalkyl group;
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from the group consisting of: F. cl, br and I.
2. A compound or use according to any preceding claim, wherein R 5 、R 6 、R 7 、R 8 、R 9 At least two of which are substituents selected from F, cl, br and I, more preferably F or Cl.
3. A compound or use according to any preceding claim, wherein a 1 、A 2 、A 3 、A 4 、A 5 Wherein 1 is N, preferably A 1 Or A 2 Is N.
4. A compound or use according to any preceding claim, wherein R 12 Selected from H, F, CL, CH 3 、CF 3 。
5. A compound or use according to any preceding claim, wherein R 13 Selected from H, F, cl, CF 3 And CH (CH) 3 。
6. A compound or according to any preceding claimUse, wherein R is 15 Selected from H and CH 3 。
7. A compound or use according to any one of the preceding claims, wherein at least one of the following selections is made:
R 1 selected from H, F and Cl; and/or
R 2 Selected from H, F and Cl; and/or
R 3 Selected from H, F and Cl; and-
R 4 Selected from H, F and Cl.
8. A compound or use according to any one of the preceding claims, wherein at least one of the following selections is made:
R 5 selected from H, F, cl, br and I; and/or
R 6 Selected from H, F and Cl, br and CH 3 The method comprises the steps of carrying out a first treatment on the surface of the And/or
R 7 Selected from H, F, cl, br and I; and/or
R 8 Selected from H, F, cl, br and CH 3 The method comprises the steps of carrying out a first treatment on the surface of the And/or
R 9 Selected from H, F, cl, br and I.
9. A compound or use according to any preceding claim, wherein:
R 1 selected from H, F and Cl;
R 2 selected from H, F and Cl;
R 3 selected from H, F and Cl;
R 4 selected from H, F and Cl;
R 5 selected from H, F, cl, br and I;
R 6 selected from H, F and Cl, br and CH 3 ；
R 7 Selected from H, F, cl, br and I;
R 8 selected from H, F, cl, br and CH 3 ；
R 9 Selected from H, F, cl, br and I;
R 11 is H;
R 12 selected from H, F, CL, CH 3 、CF 3 ；
R 13 Selected from H, F, cl, CF 3 And CH (CH) 3 ；
R 14 Is H or F;
R 15 selected from H and CH 3 The method comprises the steps of carrying out a first treatment on the surface of the And
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from F, cl, br and I.
10. The compound and use according to any one of the preceding claims, wherein:
R 1 is H;
R 2 selected from H, F and Cl;
R 3 selected from H, cl, F and Br;
R 4 is H, F, cl;
R 5 selected from H, F and Cl;
R 6 selected from H, F, cl and CH 3 ；
R 7 Selected from H, F and Cl;
R 8 selected from H, F, cl and CH 3 ；
R 9 Selected from H, F and Cl;
R 11 is H;
R 12 selected from H, F and Cl;
R 13 selected from H, F and Cl;
R 14 is H;
R 15 selected from H and CH 3 The method comprises the steps of carrying out a first treatment on the surface of the And
wherein R is 5 、R 6 、R 7 、R 8 、R 9 At least one of which is a substituent selected from F, cl, br and I.
11. A compound for use according to any one of the preceding claims, wherein the parasite infestation is an ectoparasite infestation.
12. A compound for use according to any one of the preceding claims, wherein the parasitic infestation is a acaricidal infestation.
13. Compound for use according to any one of the preceding claims, wherein the parasite infestation is a infestation selected from ticks, fleas and/or flies, preferably a tick infestation.
14. A compound for use according to any one of the preceding claims, wherein the parasite is a single-host tick or a multi-host tick, preferably the parasite is rhipicephalus minutissimus.
15. The compound for use according to any one of the preceding claims, wherein the animal is a warm-blooded animal, especially a mammal.
16. The compound for use according to any one of claims 1-15, wherein the animal is a domestic animal, in particular a ruminant, in particular a bovine.
17. The compound for use according to any one of claims 1-15, wherein the animal is a fish and the parasite infestation is sea lice infestation.
18. The compound for use according to any one of claims 1-15, wherein the animal is a companion animal, especially a canine or a feline, especially a dog or cat.
19. The compound for use according to any one of the preceding claims, wherein the animal is protected from parasite infestation.
20. The compound for use according to any one of the preceding claims, wherein the animal's existing parasite infestation is treated or controlled.
21. The compound for use according to any one of the preceding claims, wherein the method comprises administering the compound to an animal weekly, biweekly, monthly, 6 weekly, 2 months, 3 months, 6 months or 9 months.
22. A veterinary composition comprising an effective amount of a compound of formula (I) as defined in any one of claims 1 to 10 and an inert carrier or formulation adjuvant.
23. The veterinary composition of claim 22, wherein the veterinary composition is a topical composition, an oral composition, or an injectable composition.
24. A veterinary composition according to claim 21 or 22 and a pharmaceutically acceptable oily carrier.
25. The veterinary composition according to claim 24, wherein the oily carrier comprises, preferably consists essentially of, a fatty acid ester.
26. The veterinary pharmaceutical composition of claim 25, wherein the fatty acid ester is C 8-10 Glycol di-or tri-esters of fatty acids, preferably propylene glycol caprate caprylate (e.g., miglyol 840).
27. The veterinary pharmaceutical composition of claim 25, wherein the oily carrier comprises a combination of glycerol monocaprylate and propylene glycol dicaprylyl decanoate.
28. The veterinary pharmaceutical composition of any one of claims 22 to 27, wherein the composition does not comprise a penetration enhancer.
29. The veterinary pharmaceutical composition according to any one of claims 22 to 28, comprising:
a) About 0.5% to about 10% w/v, preferably 1% of said compound of formula (I);
b1 About 90% to 99.9% w/v of the preferred propylene glycol caprylate caprate; or alternatively b 2) from about 10% to about 40% w/v, preferably 20% glycerol monocaprylate; and
c) Optionally from about 2% to about 50% w/v, preferably 99% propylene glycol dicapryl decanoate.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP21153638.8 | 2021-01-27 | ||
| US202163292561P | 2021-12-22 | 2021-12-22 | |
| US63/292,561 | 2021-12-22 | ||
| PCT/EP2022/051674 WO2022161972A1 (en) | 2021-01-27 | 2022-01-26 | Antiparasitic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN116964031A true CN116964031A (en) | 2023-10-27 |
Family
ID=88447765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202280016464.4A Pending CN116964031A (en) | 2021-01-27 | 2022-01-26 | Antiparasitic compounds |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN116964031A (en) |
-
2022
- 2022-01-26 CN CN202280016464.4A patent/CN116964031A/en active Pending
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