CN110536891A - 用作杀虫剂的介离子咪唑并吡啶 - Google Patents
用作杀虫剂的介离子咪唑并吡啶 Download PDFInfo
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- CN110536891A CN110536891A CN201880025909.9A CN201880025909A CN110536891A CN 110536891 A CN110536891 A CN 110536891A CN 201880025909 A CN201880025909 A CN 201880025909A CN 110536891 A CN110536891 A CN 110536891A
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- Prior art keywords
- alkyl
- alkoxy
- halogenated
- carbonyl
- base
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- 239000002917 insecticide Substances 0.000 title abstract description 6
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 108
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 41
- 241001465754 Metazoa Species 0.000 claims abstract description 28
- 241000244206 Nematoda Species 0.000 claims abstract description 24
- 241000238631 Hexapoda Species 0.000 claims abstract description 19
- 241000239223 Arachnida Species 0.000 claims abstract description 8
- -1 C (R5a)(R5b)(R5c) Chemical group 0.000 claims description 420
- 125000001424 substituent group Chemical group 0.000 claims description 177
- 229910052736 halogen Inorganic materials 0.000 claims description 124
- 150000002367 halogens Chemical class 0.000 claims description 117
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 101
- 125000000217 alkyl group Chemical group 0.000 claims description 94
- 125000001072 heteroaryl group Chemical group 0.000 claims description 83
- 125000003118 aryl group Chemical group 0.000 claims description 78
- 239000001257 hydrogen Substances 0.000 claims description 77
- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- 125000003545 alkoxy group Chemical group 0.000 claims description 72
- 239000011737 fluorine Substances 0.000 claims description 68
- 229910052731 fluorine Inorganic materials 0.000 claims description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 66
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 60
- 239000000460 chlorine Substances 0.000 claims description 59
- 229910052801 chlorine Inorganic materials 0.000 claims description 59
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 51
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 49
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 48
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 45
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 38
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 37
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 29
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 229910052794 bromium Inorganic materials 0.000 claims description 24
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 21
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 230000036541 health Effects 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 17
- 238000006467 substitution reaction Methods 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 11
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 241000534944 Thia Species 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 9
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 8
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 7
- 239000005864 Sulphur Substances 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000005493 quinolyl group Chemical group 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 150000005071 1,2,4-oxadiazoles Chemical class 0.000 claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- AMFYRKOUWBAGHV-UHFFFAOYSA-N 1h-pyrazolo[4,3-b]pyridine Chemical compound C1=CN=C2C=NNC2=C1 AMFYRKOUWBAGHV-UHFFFAOYSA-N 0.000 claims description 4
- FJRPOHLDJUJARI-UHFFFAOYSA-N 2,3-dihydro-1,2-oxazole Chemical compound C1NOC=C1 FJRPOHLDJUJARI-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
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- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 3
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- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- IHNSIFFSNUQGQN-UHFFFAOYSA-N tioxazafen Chemical compound C1=CSC(C=2ON=C(N=2)C=2C=CC=CC=2)=C1 IHNSIFFSNUQGQN-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 210000003371 toe Anatomy 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- HRINTZHMQJJUME-UHFFFAOYSA-N trichloro(nitro)methane Chemical compound [O-][N+](=O)C(Cl)(Cl)Cl.[O-][N+](=O)C(Cl)(Cl)Cl HRINTZHMQJJUME-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- VRNFXUOQGOAQBZ-DYXAMGHASA-N veratrin Chemical compound C1[C@@H](C)CC[C@H]2[C@](O)(C)[C@@]3(O)[C@@H](O)C[C@@]4(O)[C@@H]5CC[C@H]6[C@]7(C)CC[C@H](OC(=O)C(\C)=C/C)[C@@]6(O)O[C@@]75C[C@@]4(O)[C@@H]3CN21.C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 VRNFXUOQGOAQBZ-DYXAMGHASA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000012873 virucide Substances 0.000 description 1
- 229940006076 viscoelastic substance Drugs 0.000 description 1
- 239000003190 viscoelastic substance Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- Pest Control & Pesticides (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
公开了适用于防治动物害虫的式(I)的化合物,所述动物害虫包括节肢动物且特别是昆虫、蛛形纲动物和线虫,且其中结构元素R1、p、T和G具有说明书中所示的含义。还公开了用于合成所述化合物的方法以及其作为杀虫剂的用途。
Description
本发明涉及新的介离子咪唑并吡啶衍生物,其制备方法及其用于防治动物害虫、尤其是节肢动物且特别是昆虫、蛛形纲动物和线虫的用途。
某些介离子咪唑并吡啶衍生物是已知的,参见例如J.Chem.Soc.Perkin Trans I,1984,69-73;Tetrahedron 1990,46,6033-6046;Can.J.Chem.1971,49,668-671;Tetrahedron 1986,42,1169-1177;Tetrahedron2009,65,7591-7596;Tetrahedron 1998,54,9689-9700;Acta Crystallographica,Section E:Structure Reports Online(2011),67(10),2814。在所述出版物中没有描述生物学作用。
本发明的目的是提供在各个方面拓宽农药谱和/或改善其活性的化合物。
出乎意料地,现已发现特别的新的介离子咪唑并吡啶衍生物具有显著的杀虫特性,且同时被植物很好地耐受并且具有有利的恒温动物毒性和良好的环境相容性。迄今尚未公开本发明的新的化合物。
因此,本发明提供通式(I)的化合物,
其中(构型1-1):
T代表氢、C(R5a)(R5b)(R5c)、C2-C8-烯基、C3-C8-炔基或C3-C8-环烷基,其中C2-C8-烯基、C3-C8-炔基和C3-C8-环烷基可各自任选地被单取代至三取代且取代基彼此独立地选自卤素和/或可各自任选地被单取代且取代基选自氰基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-环烷基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、芳基、杂芳基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基,其中芳基、杂芳基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,或
T代表芳基、C1-C6-亚烷基二氧基芳基、杂芳基、C3-C8-杂环基、C3-C8-氧代杂环基或C3-C8-二氧代杂环基,其中上述基团可各自任选地被单取代至五取代且取代基彼此独立地选自卤素、硝基、氨基、氰基、SF5、SCN、C1-C6-烷基氨基、二-(C1-C6-烷基)氨基、羟基、COOH、C1-C6-烷基、C3-C6-环烷基、C3-C6-杂环基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C3-C6-卤代环烷基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、SH、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、三-(C1-C6-烷基)甲硅烷基、芳基、杂芳基、杂环基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基,其中芳基、杂芳基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,或
T代表N(R7a)(R7b)或N(R8)-N(R11a)(R11b),或
T代表C(=W)R12或C(=O)OR13,
W代表O或N-OR15,
G代表C1-C6-烷基或C2-C6-烯基,其中上述基团各自被卤素单取代至五取代和/或被以下基团单取代至二取代:氰基、C1-C4-烷氧基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、C1-C4-羰基-C1-C4-烷氧基或C1-C4-烷氧基亚氨基-C1-C4-烷基,
R1在每种情况下代表氢、卤素、氰基、硝基、SF5、SCN、氨基、C1-C6-烷基氨基、二-(C1-C6)-烷基氨基、羟基、COOH、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C3-C6-卤代环烷基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C2-C6-烯氧基、C3-C6-炔基、C3-C6-炔氧基、SH、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷硫基、C1-C6-卤代烷基亚磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基亚氨基-C1-C6-烷基、C1-C6-烷氧基羰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、芳基、杂芳基、芳基-C1-C6-烷基或杂芳基-C1-C6-烷基,
其中芳基、杂芳基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基可各自任选地被单取代或多取代且取代基彼此独立地选自卤素、氰基、硝基、羟基、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基和C1-C6-烷硫基,
或
两个基团R1一起形成5元或6元脂族环、芳族环、杂芳族环或杂环,所述环可任选地含有1至2个选自O、S和N的原子且其可任选地被单取代或多取代,其中取代基彼此独立地选自卤素和C1-C4-烷基,
p代表0、1、2或3,
R5a和R5b彼此独立地代表氢、卤素、氰基、C1-C6-烷基、C1-C6-卤代烷基或C1-C6-烷氧基,
R5c代表氢、氟、氯、溴、氰基、C1-C6-烷氧基羰基、C1-C6-烷基、C1-C6-烷氧基、C3-C8-环烷基、C2-C6-烯基或C2-C6-炔基,其中C1-C6-烷基、C3-C8-环烷基、C2-C6-烯基和C2-C6-炔基可各自任选地被单取代至五取代且取代基彼此独立地选自卤素和/或可各自任选地被单取代且取代基选自硝基、氰基、C1-C6-卤代烷基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基羰基氨基、C1-C6-烷基氨基羰基、二-(C1-C6-烷基)氨基羰基、C1-C6-烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷氧基亚氨基-C1-C6-烷基、芳基、杂芳基和杂环基,其中芳基、杂芳基和杂环基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、C1-C6-烷硫基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、C1-C6-烷基羰基氨基、芳基和杂芳基,其中芳基和杂芳基本身可各自任选地被单取代或多取代且取代基彼此独立地选自卤素、氰基、硝基、羟基、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基和C1-C6-烷硫基,或
R5c代表芳基、C-键合的杂芳基、N-键合的杂芳基、C3-C8-杂环基、C3-C8-氧代杂环基或C3-C8-二氧代杂环基,其中上述基团可各自任选地被单取代至五取代且取代基彼此独立地选自卤素、硝基、氨基、氰基、SF5、SCN、C1-C6-烷基氨基、二-(C1-C6-烷基)氨基、羟基、COOH、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C3-C6-卤代环烷基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、SH、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6-烷基)氨基羰基、C1-C6-烷基羰基氨基、三-(C1-C6-烷基)甲硅烷基、芳基、杂芳基、杂环基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基,其中芳基、杂芳基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、羟基、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-卤代烷基、C1-C6-烷氧基和C1-C6-卤代烷氧基或C1-C6-烷硫基,
R13和R15彼此独立地代表氢,或
代表C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C3-C6-环烷基-C1-C6-烷基、杂环基、杂环基-C1-C6-烷基、芳基、杂芳基、芳基-C1-C6-烷基或杂芳基-C1-C6-烷基、C3-C6-氧代杂环基或C3-C6-二氧代杂环基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自硝基、氰基、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-烷基羰基、C1-C6-烷氧基亚氨基-C1-C6-烷基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、芳基和杂芳基,其中芳基和杂芳基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
R7a和R11a彼此独立地代表氢、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C6-烷基、C1-C6-烷氧基羰基、C1-C6-烷基羰基或C1-C6-烷基磺酰基,
R7b和R11b彼此独立地代表氢、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基或C3-C6-杂环基,其中C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基和C3-C6-杂环基可各自任选地被单取代至五取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自硝基、氰基、羟基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、芳基、杂芳基、杂环基和氧代杂环基,其中芳基、C3-C6-环烷基、杂芳基、杂环基和氧代杂环基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、C1-C6-烷硫基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、C1-C6-烷基羰基氨基、芳基和杂芳基,其中芳基和杂芳基本身可各自任选地被单取代或多取代且取代基彼此独立地选自卤素、氰基、硝基、羟基、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基和C1-C6-烷硫基,或
R7b和R11b彼此独立地代表芳基或杂芳基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氨基、氰基、SF5、SCN、C1-C6-烷基氨基、二-(C1-C6)-烷基氨基、羟基、COOH、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C3-C6-卤代环烷基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、SH、C1-C6-烷硫基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基和三-(C1-C6-烷基)甲硅烷基,
或
R7a和R7b可以通过2至6个碳原子彼此连接并形成环,所述环可任选另外地含有选自O、S和N的其他原子并且可任选地被单取代至四取代且取代基彼此独立地选自C1-C2-烷基、卤素、氰基、氨基和C1-C2-烷氧基,或
R11a和R11b可以通过2至6个碳原子彼此连接并形成环,所述环可任选另外地含有选自O、S和N的其他原子并且可任选地被单取代至四取代且取代基彼此独立地选自C1-C2-烷基、卤素、氰基、氨基和C1-C2-烷氧基,或
R8代表氢、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C1-C4-烷氧基-C1-C6-烷基、C1-C6-烷氧基羰基或C1-C6-烷基羰基,
且
R12代表氢、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基或C3-C6-杂环基,其中C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基和C3-C6-杂环基可各自任选地被单取代至五取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自硝基、氰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、芳基、杂芳基、杂环基和氧代杂环基,其中芳基、杂芳基、杂环基和氧代杂环基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、C1-C6-烷硫基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、C1-C6-烷基羰基氨基、芳基和杂芳基,其中芳基和杂芳基本身可各自任选地被单取代或多取代且取代基彼此独立地选自卤素、氰基、硝基、羟基、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基和C1-C6-烷硫基,
或
R12代表芳基或杂芳基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氨基、氰基、SF5、SCN、C1-C6-烷基氨基、二-(C1-C6)-烷基氨基、羟基、COOH、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C3-C6-卤代环烷基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、SH、C1-C6-烷硫基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基和三-(C1-C6-烷基)甲硅烷基。
式(I)的化合物同样涵盖所存在的任何非对映异构体或对映异构体和E/Z异构体,以及式(I)的化合物的盐和N-氧化物,及其用于防治动物害虫的用途。
取代的介离子咪唑衍生物通常由式(I)定义。下文给出了在上下文中指定的式的优选基团定义。
优选的(构型2-1)为式(I)的化合物,其中
T代表氢、C(R5a)(R5b)(R5c)、C2-C6-烯基、C3-C6-炔基或C3-C6-环烷基,其中C2-C6-烯基、C3-C6-炔基和C3-C6-环烷基可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基,
或
T代表芳基、C1-C6-亚烷基二氧基苯基、杂芳基或C3-C6-杂环基,其中上述基团可各自任选地被单取代至五取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C4-烷基、C3-C6-杂环基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C2-C4-烯基、C3-C4-炔基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基羰基、C3-C6-环烷基羰基、C2-C4-烯基羰基、C1-C4-卤代烷基羰基、C1-C4-烷氧基羰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基磺酰基、芳基、杂芳基、杂环基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基,其中芳基、杂芳基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基本身可各自被单取代至三取代且取代基彼此独立地选自卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
或
T代表N(R7a)(R7b)或N(R8)-N(R11a)(R11b),
或
T代表C(=W)R12或C(=O)OR13,
W代表O或N-OR15,
G代表C1-C6-烷基或C2-C6-烯基,其中上述基团各自被卤素单取代至五取代和/或被以下基团单取代至二取代:氰基、C1-C4-烷氧基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、C1-C4-羰基-C1-C4-烷氧基、C1-C4-烷氧基亚氨基-C1-C4-烷基,
R1代表氢、卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基,
p代表1或2,
R5a和R5b彼此独立地代表氢、卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基,
R5c代表氢、氟、氯、溴、氰基、C1-C4-烷氧基羰基、C1-C4-烷基、C1-C4-烷氧基、C3-C6-环烷基、C2-C6-烯基或C2-C6-炔基,其中C1-C4-烷基、C3-C6-环烷基、C2-C6-烯基和C2-C6-炔基可各自任选地被单取代至五取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自硝基、氰基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷基羰基和C1-C4-烷氧基羰基,
或
R5c代表芳基或C-键合的杂芳基,其中上述基团可各自任选地被单取代至五取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷氧基羰基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基,
或
R5c代表Y,
Y代表基团Y-1至Y-23之一,
Xb代表卤素、硝基、氰基、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、C1-C6-烷硫基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、C1-C6-烷基羰基氨基、芳基或杂芳基,其中芳基和杂芳基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、羟基、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基和C1-C6-烷硫基且其中Y-13、Y-14和Y-16中的环氮原子不被以下基团取代:卤素、硝基、氰基、C1-C4-烷氧基、C1-C4-卤代烷氧基或C1-C4-烷氧基-C1-C4-烷基氧基,
m代表0、1或2,
R13和R15彼此独立地代表氢,或
代表C1-C4-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C3-C6-环烷基-C1-C4-烷基、C3-C6-杂环基、C3-C6-杂环基-C1-C4-烷基、C3-C6-氧代杂环基、C3-C6-二氧代杂环基、苯基、吡啶基、苯基-C1-C4-烷基或吡啶基-C1-C4-烷基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C3-C6-环烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-烷氧基羰基、芳基和杂芳基,其中芳基和杂芳基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
R7a和R11a彼此独立地代表氢、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷氧基羰基或C1-C6-烷基羰基,
R7b和R11b彼此独立地代表氢,或
彼此独立地代表C1-C6-烷基或C3-C6-环烷基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可任选地被单取代且取代基选自氰基、硝基、羟基和C1-C4-烷氧基、C3-C6-环烷基、芳基和杂芳基,其中芳基、C3-C6-环烷基和杂芳基本身可被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
或
R7b和R11b彼此独立地代表芳基或杂芳基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基,或
R7a和R7b可以通过2至6个碳原子彼此连接并形成环,所述环可任选另外地含有选自O、S和N的其他原子并且可任选地被单取代至四取代且取代基彼此独立地选自C1-C2-烷基、氟、氯、溴和C1-C2-烷氧基,或
R11a和R11b可以通过2至6个碳原子彼此连接并形成环,所述环可任选另外地含有选自O、S和N的其他原子并且可任选地被单取代至四取代且取代基彼此独立地选自C1-C2-烷基、氟、氯、溴和C1-C2-烷氧基,或
R8代表氢、C1-C6-烷基、C3-C6-环烷基、C1-C6-烷氧基羰基或C1-C6-烷基羰基,
并且
R12代表C1-C6-烷基,其可任选地被单取代至五取代且其中取代基彼此独立地选自卤素,和/或其可任选地被单取代且其中取代基选自硝基、氰基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
或
R12代表芳基或杂芳基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基。
进一步优选的(构型3-1)为式(I)的化合物,其中
T代表氢、C(R5a)(R5b)(R5c)、C2-C4-烯基、C3-C4-炔基或C3-C6-环烷基,其中C2-C4-烯基、C3-C4-炔基或C3-C6-环烷基可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基,
或
T代表苯基、C1-C4-亚烷基二氧基苯基、萘基、呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,5-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、苯硫基(thiophenyl)、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、苯并呋喃基、吲哚基、苯并噻唑基、苯并噁唑基、苯并咪唑基、吡唑并吡啶基、喹啉基、异喹啉基、噌啉基、氮杂环丁烷基(azetidinyl)、氮杂环戊基(azolidinyl)、氮杂环己基(azinanyl)、氧杂环丁基(oxetanyl)、氧杂环戊基(oxolanyl)、氧杂环己基(oxanyl)、二氧杂环己基(dioxanyl)、硫杂环丁基(thiethanyl)、硫杂环戊基(thiolanyl)、硫杂环己基(thianyl)或二氢异噁唑基,其中上述基团可各自任选地被单取代至四取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代至二取代且取代基彼此独立地选自溴、硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基磺酰基、苯基、吡啶基和吗啉基,其中总共存在最多五个上述取代基且其中苯基和吡啶基本身可另外地各自被单取代至三取代且取代基彼此独立地选自卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
或
T代表N(R7a)(R7b),
或
T代表C(=W)R12或C(=O)OR13,
W代表O或N-OR15,
G代表C1-C4-烷基或C2-C4-烯基,其中上述基团各自被卤素单取代至三取代和/或被氰基单取代,
R1代表氢、氟、氯、甲基、乙基、甲氧基或乙氧基,
p代表1,
R5a和R5b彼此独立地代表氢、卤素、C1-C4-烷基或C1-C4-烷氧基,
R5c代表氢、氟、氯、溴、氰基、C1-C4-烷氧基羰基、C1-C4-烷基、C1-C4-烷氧基或C3-C6-环烷基,其中C1-C4-烷基和C3-C6-环烷基可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自氰基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-烷氧基羰基,
或
R5c代表苯基或C-键合的吡啶基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷氧基羰基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基,
或
R5c代表Y,
Y代表代表基团Y-2、Y-3、Y-4、Y-5、Y-6或Y-7之一,
Xb代表卤素、氰基、甲基、乙基、三氟甲基、二氟甲基、甲基氨基羰基、甲基羰基氨基、甲氧基、乙氧基、三氟甲氧基、甲硫基、乙硫基、甲基亚磺酰基、甲基磺酰基或甲氧基羰基,
m代表0、1或2,
R13和R15彼此独立地代表氢,或
代表C1-C4-烷基、C3-C6-环烷基、C3-C6-杂环基或C3-C6-二氧代杂环基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自氰基、C1-C4-烷基、C1-C4-卤代烷基、C3-C6-环烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-烷氧基羰基、苯基和吡啶基,其中苯基和吡啶基本身可各自被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
R7a代表氢或C1-C4-烷基,
R7b代表氢,或
代表C1-C6-烷基或C3-C6-环烷基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可任选地被单取代且取代基选自C3-C6-环烷基和苯基,其中C3-C6-环烷基和苯基本身可被单取代至三取代且取代基彼此独立地选自卤素、C1-C4-烷基、C1-C4-卤代烷基和C1-C4-烷氧基,
或
R7b代表苯基、吡啶基或吡唑基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基,或
R7a和R7b可以通过2至6个碳原子彼此连接并形成环,所述环可任选另外地含有选自O、S和N的其他原子并且可任选地被单取代至四取代且取代基彼此独立地选自甲基、乙基、氟、甲氧基和乙氧基,
并且
R12代表C1-C4-烷基,其可任选地被单取代至五取代基且其中取代基彼此独立地选自卤素,
或
R12代表苯基,其可任选地被单取代至三取代基且其中取代基彼此独立地选自卤素。
特别优选的(构型4-1)为式(I)的化合物,其中
T代表氢、C(R5a)(R5b)(R5c)、乙烯基、丙烯基、环丙基、环丁基、环戊基或环己基,其中乙烯基、丙烯基、环丙基、环丁基、环戊基和环己基可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代且取代基选自氰基、甲基、乙基、三氟甲基和甲氧基,
或
T代表苯基、吡啶基、嘧啶基、苯硫基、呋喃基、吡咯基、噻唑基、异噻唑基、噁唑基、异噁唑基、吡唑基、咪唑基、吡唑并吡啶基、苯并噻唑基、苯并呋喃基、苯并噁唑基、喹啉基、氧杂环戊基或二氢异噁唑基,其中上述基团可各自任选地被单取代至四取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代至二取代且取代基彼此独立地选自溴、氰基、甲基、乙基、二氟甲基、三氟甲基、三氟乙基、五氟乙基、三氟丙基、甲氧基、乙氧基、三氟甲氧基、甲硫基、甲基亚磺酰基、甲基磺酰基、吗啉基和苯基,
或
T代表N(R7a)(R7b),
或
T代表C(=W)R12或C(=O)OR13,
W代表O或N-OR15,
G代表氰基甲基、2-氰基乙基、2,2,2-三氟乙基或3,3,3-三氟丙基,
R1代表氢或甲基,
p代表1,
R5a和R5b彼此独立地代表氢、氟、氯、甲基、乙基、甲氧基或乙氧基,
R5c代表氢、氟、氯、溴、氰基、甲氧基和甲氧基羰基,或代表甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、环丙基或苯基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代且取代基选自氰基、甲氧基、甲氧基羰基和三氟甲基,其中总共存在最多三个上述取代基,
或
R5c代表Y,
Y代表基团Y-2,
Xb代表氟、氯、溴、氰基、甲基、乙基、甲氧基、乙氧基、甲硫基、二氟甲基或三氟甲基,
m代表0或1,
R13和R15彼此独立地代表氢,或
代表C1-C4-烷基、环丙基、环丁基、环戊基、环己基、氧杂环己基或1,1-二氧代硫杂环己基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代且取代基选自氰基、甲基、甲氧基、三氟甲基,或
R13和R15彼此独立地代表环丙基甲基,或
代表苯基甲基或吡啶基甲基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代且取代基选自氰基、甲基、甲氧基、三氟甲基,其中总共存在最多三个上述取代基,
R7a代表氢,
R7b代表C1-C4-烷基、环丙基、苄基或环丙基甲基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,
或
代表苯基、吡啶基或吡唑基,其中上述基团可任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可任选地被单取代且取代基选自氰基、甲基、甲氧基、三氟甲基、甲硫基、甲基亚磺酰基和甲基磺酰基,其中总共存在最多三个上述取代基,并且
R12代表甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基或苯基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯。
还特别优选的(构型4-2)为式(I)的化合物,其中
T代表氢、C(R5a)(R5b)(R5c)、乙烯基、丙烯基、环丙基、环丁基、环戊基或环己基,其中乙烯基、丙烯基、环丙基、环丁基、环戊基和环己基可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代且取代基选自氰基、甲基、乙基、三氟甲基和甲氧基,
或
T代表苯基、吡啶基、嘧啶基、苯硫基、呋喃基、吡咯基、噻唑基、异噻唑基、1,3-噁唑基、1,2-噁唑基、吡唑基、咪唑基、1,2,4-噁二唑基、吡唑并吡啶基、苯并噻唑基、苯并呋喃基、苯并噁唑基、喹啉基、氧杂环戊基或二氢异噁唑基,其中上述基团可各自任选地被单取代至四取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代至二取代且取代基彼此独立地选自溴、氰基、甲基、乙基、二氟甲基、三氟甲基、三氟乙基、五氟乙基、三氟丙基、甲氧基、乙氧基、三氟甲氧基、甲硫基、甲基亚磺酰基、甲基磺酰基、吗啉基和苯基,
或
T代表N(R7a)(R7b),
或
T代表C(=W)R12或C(=O)OR13,
W代表O或N-OR15,
G代表氰基甲基、2-氰基乙基、2,2,2-三氟乙基或3,3,3-三氟丙基,
R1代表氢或甲基,
p代表1,
R5a和R5b彼此独立地代表氢、氟、氯、甲基、乙基、甲氧基或乙氧基,
R5c代表氢、氟、氯、溴、氰基、甲氧基和甲氧基羰基,或代表甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、环丙基或苯基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代且取代基选自氰基、甲氧基、甲氧基羰基和三氟甲基,其中总共存在最多三个上述取代基,
或
R5c代表Y,
Y代表基团Y-2,
Xb代表氟、氯、溴、氰基、甲基、乙基、甲氧基、乙氧基、甲硫基、二氟甲基或三氟甲基,
m代表0或1,
R13和R15彼此独立地代表氢,或代表C1-C4-烷基、环丙基、环丁基、环戊基、环己基、氧杂环己基或1,1-二氧代硫杂环己基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代且取代基选自氰基、甲基、甲氧基、三氟甲基,或
R13和R15彼此独立地代表环丙基甲基或环丁基甲基,或
代表苯基甲基或吡啶基甲基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代且取代基选自氰基、甲基、甲氧基、三氟甲基、其中总共存在最多三个上述取代基,
R7a代表氢,
R7b代表C1-C4-烷基、环丙基、苄基或环丙基甲基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,或
代表苯基、吡啶基或吡唑基,其中上述基团可任选地被单取代至三取代且取代基彼此独立地选自氟、氯和甲基,和/或可任选地被单取代且取代基选自氰基、甲基、甲氧基、三氟甲基、甲硫基、甲基亚磺酰基和甲基磺酰基,其中总共存在最多三个上述取代基,
和
R12代表甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基或苯基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯。
非常特别优选的(构型5-1)为式(I)的化合物,其中
T代表C(R5a)(R5b)(R5c)、环丙基、苯基、3-三氟甲基苯基、噁唑-2-基或1-甲基吡唑-4-基,
或
T代表N(R7a)(R7b),
或
T代表C(=W)R12或C(=O)OR13,
W代表O,
G代表2-氰基乙基或2,2,2-三氟乙基,
R1代表氢或甲基,
p代表1,
R5a和R5b彼此独立地代表氢或氟,
R5c代表氢、氟、甲氧基或4-氯吡唑-1-基,
R7a代表氢,
R7b代表环丙基、2,6-二氯苯基、3-氟吡啶-2-基、3-三氟甲基吡啶-2-基、2,4-二氯吡啶-3-基或1-甲基吡唑-5-基,
R12代表甲基,并且
R13代表甲基、乙基、2,2,2-三氟乙基或环丁基。
还非常特别优选的(构型5-2)为式(I)的化合物,其中
T代表C(R5a)(R5b)(R5c)、环丙基、苯基、3-三氟甲基苯基、1,3-噻唑-2-基、1,3-噁唑-2-基、1,2-噁唑-5-基、3-苯基-1,2,4-噁二唑-5-基、5-三氟甲基呋喃-2-基、1-甲基吡唑-3-基或1-甲基吡唑-4-基,
或
T代表N(R7a)(R7b),
或
T代表C(=W)R12或C(=O)OR13,
W代表O或甲氧基亚氨基,
G代表2-氰基乙基或2,2,2-三氟乙基,
R1代表氢或甲基,
p代表1,
R5a和R5b彼此独立地代表氢或氟,
R5c代表氢、氟、氯、甲氧基、三氟甲基或4-氯吡唑-1-基,
R7a代表氢,
R7b代表环丙基、2,6-二氯苯基、2,6-二氟苯基、2,6-二甲基苯基、2-氯-6-氰基苯基、3-氟吡啶-2-基、3-三氟甲基吡啶-2-基、2,4-二氯吡啶-3-基或1-甲基吡唑-5-基,
R12代表甲基,并且
R13代表甲基、乙基、2,2,2-三氟乙基、环丁基、环丁基甲基、1-甲基环丙基。
在另一个优选的实施方案中,本发明涉及式(I-1)的化合物
其中结构元素R1、G和T具有构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)中给出的含义。
在另一个优选的实施方案中,本发明涉及式(I-1a)的化合物
其中,特别优选下文所示的构型:
在另一个优选的实施方案中,本发明涉及式(I-1b)的化合物
其中,特别优选下文所示的构型:
同样优选的本发明的化合物是表1中所示的通式(I)的化合物。
上文给出的一般性或优选的基团定义或说明适用于所有式(I)的化合物并且相应地适用于原料和中间体。这些基团定义可以根据需要相互组合,即包括各个优选范围之间的组合。
根据本发明优选的是式(I)的化合物,其中存在上文给出的优选定义的组合,并且上文所述的各优选构型构成独立的组合,特别是如构型2-1中所述的组合。
根据本发明更优选的是式(I)的化合物,其中存在上文给出的更优选的定义的组合,并且上文所述的更优选的各构型构成独立的组合,特别是如构型3-1中所述的组合。
根据本发明特别优选的是式(I)的化合物,其中存在上文给出的特别优选的定义的组合,并且上文所述的特别优选的各构型构成独立的组合,特别是如构型4-1中所述的组合。
根据本发明非常特别优选的是式(I)的化合物,其中存在上文给出的非常特别优选的定义的组合,并且上文所述的非常特别优选的各构型构成独立的组合,特别是如构型5-1中所述的组合。
除非在适当的地方另有规定,任选取代的基团可以是单取代或多取代的,其中在多取代的情况下取代基可以是相同的或不同的。因此,结构元素上取代基的最大数目取决于该具体结构元素中可用于取代基的最大位置数。
式(I)的化合物为介离子内盐。内盐,也称为两性离子,是电学上不带电荷的分子,其形式上在不同原子上带有正电荷和负电荷。式(I)的化合物在形式上可由在不同原子上带有正电荷和负电荷的各种结构表示。下图示出了4种可能的表示形式,不排除其他可能的表示形式。所有的结构表示都是等效的。出于简化的原因,在本文中在每种情况下仅选择一种可能的结构表示。这种表示应理解为在每种情况下代表所有的价键结构表示。
根据取代基的性质,式(I)的化合物还可以是立体异构体的形式,即几何异构体和/或光学异构体或不同组成的异构体混合物的形式。本发明提供纯的立体异构体和任何所需的所述异构体的混合物,尽管通常仅为本文所述的式(I)的化合物。
然而,根据本发明,优选使用式(I)的化合物及其盐的光学活性的立体异构体形式。
因此,本发明涉及纯的对映异构体和非对映异构体及其混合物,用于防治动物害虫,包括节肢动物,特别是昆虫。
如果合适的话,式(I)的化合物可以以各种多晶型形式或作为各种多晶型形式的混合物存在。纯的多晶型物和多晶型物混合物由本发明提供并且可以根据本发明使用。
在本发明的上下文中,除非另有不同定义,术语“烷基”——本身或与其他术语组合例如卤代烷基——应理解为是指饱和脂族烃基基团,其具有1至12个碳原子并且可以是支链的或非支链的。C1-C12-烷基的实例为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基、1-甲基丁基、2-甲基丁基、1-乙基丙基、1,2-二甲基丙基、己基、正庚基、正辛基、正壬基、正癸基、正十一烷基和正十二烷基。在这些烷基中,特别优选C1-C6-烷基。特别优选C1-C4-烷基。
根据本发明,除非另有不同定义,术语“烯基”——本身或与其他术语组合——应理解为是指具有至少一个双键的直链或支链的C2-C12-烯基,例如乙烯基、烯丙基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1,3-丁二烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1,3-戊二烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基和1,4-己二烯基。其中,优选C2-C6-烯基,且特别优选C2-C4-烯基。
根据本发明,除非另有不同定义,术语“炔基”——本身或与其他术语组合——应理解为是指具有至少一个三键的直链或支链的C2-C12-炔基,例如乙炔基、1-丙炔基和炔丙基。其中,优选C3-C6-炔基,且特别优选C3-C4-炔基。炔基还可以含有至少一个双键。
根据本发明,除非另有不同定义,术语“环烷基”——本身或与其他术语组合——应理解为是指C3-C8-环烷基,例如环丙基、环丁基、环戊基、环己基、环庚基和环辛基。其中,优选C3-C6-环烷基。
根据本发明,除非另有不同定义,术语“芳基”应理解为是指具有6至14个碳原子的芳族基团,优选苯基、萘基、蒽基或菲基,更优选苯基。
除非另有不同定义,术语“芳基烷基”应理解为是指根据本发明定义的基团“芳基”和“烷基”的结合,其中所述基团通常通过烷基连接。其实例为苄基、苯乙基或α-甲基苄基,特别优选苄基。
除非另有不同定义,“杂芳基”表示碳原子和至少一个杂原子的单环、双环或三环杂环基团,其中至少一个环为芳族的。优选地,杂芳基含有3、4、5或6个碳原子,其选自呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,5-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、苯并呋喃基、苯并异呋喃基、苯并噻吩基、苯并异噻吩基、吲哚基、异吲哚基、吲唑基、苯并噻唑基、苯并异噻唑基、苯并噁唑基、苯并异噁唑基、苯并咪唑基、2,1,3-苯并噁二唑、喹啉基、异喹啉基、噌啉基、酞嗪基、喹唑啉基、喹喔啉基、萘啶基、苯并三嗪基、嘌呤基、蝶啶基和吲嗪基(indolizinyl)。
除非另有不同定义,“杂环基”表示碳原子和至少一个在环中的杂原子的饱和或部分饱和的4、5、6或7元单环。优选地,杂环基含有3、4、5或6个碳原子和1或2个选自氧、硫和氮的杂原子。杂环基的实例为氮杂环丁烷基、氮杂环戊基、氮杂环己基、氧杂环丁基、氧杂环戊基、氧杂环己基、二氧杂环己基、硫杂环丁基(thietanyl)、硫杂环戊基、硫杂环己基和四氢呋喃基。
除非另有不同定义,“氧代杂环基”和“二氧代杂环基”表示在环中的至少一个位置中含有分别被一个和两个(=O)基团取代的环原子的杂环基。优选地,杂原子(例如硫)被一个或两个(=O)基团取代,分别得到-S(=O)-和-S(=O)2-基团,其中硫原子是环的构成成分。
在本发明上下文中,卤素取代的基团,例如“卤代烷基”应理解为是指被卤素单取代或多取代至最高达最大可能的取代基数的基团。在多卤代的情况下,卤素原子可以相同或不同。本文的“卤素”是氟、氯、溴或碘,优选氟或氯。
在本发明中,术语“烷氧基”——本身或与其他术语组合例如卤代烷氧基——应理解为是指O-烷基,其中术语“烷基”如上文所定义。
方法和中间体的描述
式(I)的化合物可以例如通过方案1中指定的方法合成。在本文中,除非另有说明,否则式中给出的基团R1、p、T、G、R7a和R7b各自具有构型(1-1)至(5-1)中给出的含义。
方案1
可以如方案1所示获得其中T不代表NR7aR7b的式(Ia)的化合物。在这里,首先,将式(II)的氨基化合物与式(III)的酰氯在碱如三乙胺的存在下反应得到式(IV)的羧酸酯,其中Alk代表C1-C4烷基。随后将式(IV)的化合物用碱例如氢氧化锂水解而得到羧酸,然后通过与酸H-Y(其中Y-代表无机酸的阴离子,例如F-、Cl-、Br-、I-、NO3 -、SO4 -、ClO4 -或BF4 -)反应进行脱羧而得到式(V)的化合物。式(V)的化合物是新的且(其为用于合成式(I)的化合物的重要中间体)也形成本发明主题的一部分。或者,首先可将式(II)的化合物与氯乙酰氯(VIII)反应而得到式(IX)的氯甲基酮,然后,以类似于已知的方法,通过式(IX)的氯甲基酮与四氟硼酸的反应而获得式(V,Y=BF4 -)的化合物(参见,Tetrahedron 65(2009),7591-7596)。然后,可将式(V)的化合物与其中L1代表Cl、Br或-O(=O)T的式(VI)的化合物(例如酰氯或酸酐)在碱如三乙胺的存在下进行反应而得到式(Ia)的化合物。
其中T代表NR5aR5b的式(Ib)的化合物可如方案1所示的方法获得。在这里,将式(IV)的酯与式(VII)的胺以类似于通常已知的方法进行反应。对于与某些胺的反应而言,如果需要,需要使用活化剂,例如三甲基铝。
式(II)的化合物是文献已知的(参见例如WO 2016171053、WO 2009099929)或可以以类似于文献已知的方法获得。式(III)的化合物是文献已知的或可以以类似于已知的方法制备(参见Tetrahedron 1993,49,9447-9452)。式(VI)和(VII)的化合物为市售可得的、文献已知的或可以以类似于已知的方法合成。
通常,式(I)的化合物可通过上述方法制备。如果个别化合物不能通过上述方法制备,则可以通过其他式(I)的化合物的衍生化,或通过个别修改所述方法来合成。例如,由其他式(I)的化合物例如通过水解、酯化、酰胺形成、还原、醚化、氧化、烯化、卤化、酰化、烷基化等制备某些式(I)的化合物可能具有优势。
本发明的用于制备新的式(I)的化合物的方法优选使用稀释剂进行。除了水之外,用于实施本发明方法的有用稀释剂为所有的惰性溶剂。实例包括:卤代烃(例如氯代烃,例如tetraethylene、四氯乙烷、二氯丙烷、二氯甲烷、二氯丁烷、氯仿、四氯化碳、三氯乙烷、三氯乙烯、五氯乙烷、二氟苯、1,2-二氯乙烷、氯苯、溴苯、二氯苯、氯甲苯、三氯苯),醇(例如甲醇、乙醇、异丙醇、丁醇),醚(例如乙基丙基醚、甲基叔丁基醚、苯甲醚、苯乙醚、环己基甲基醚、二甲醚、乙醚、二丙醚、二异丙醚、二正丁醚、二异丁醚、二异戊醚、乙二醇二甲醚、四氢呋喃、1,4-二噁烷、二氯二乙基醚和环氧乙烷和/或环氧丙烷的聚醚),胺(例如三甲胺、三乙胺、三丙胺和三丁胺、N-甲基吗啉、吡啶和四亚甲基二胺),硝基烃(例如硝基甲烷、硝基乙烷、硝基丙烷、硝基苯、氯硝基苯、邻硝基甲苯);腈(例如乙腈、丙腈、丁腈、异丁腈、苄腈、间氯苄腈),四氢噻吩二氧化物,二甲基亚砜,四亚甲基亚砜,二丙基亚砜,苄基甲基亚砜,二异丁基亚砜,二丁基亚砜,二异戊基亚砜,砜(例如二甲基砜、二乙基砜、二丙基砜、二丁基砜、二苯基砜、二己基砜、甲基乙基砜、乙基丙基砜、乙基异丁基砜和五亚甲基砜),脂族烃,脂环族烃或芳族烃(例如戊烷、己烷、庚烷、辛烷、壬烷和工业级烃),以及含有沸点为例如40℃至250℃的组分的“石油溶剂油(white spirit)”,伞花烃,沸点为70℃至190℃的汽油馏分,环己烷,甲基环己烷,石油醚,轻石油,辛烷,苯,甲苯,氯苯,溴苯,硝基苯,二甲苯,酯(例如乙酸甲酯、乙酸乙酯、乙酸丁酯和乙酸异丁酯,碳酸二甲酯、碳酸二丁酯和碳酸亚乙酯);酰胺(例如六亚甲基磷三酰胺、甲酰胺、N-甲基甲酰胺、N,N-二甲基甲酰胺、N,N-二丙基甲酰胺、N,N-二丁基甲酰胺、N-甲基吡咯烷、N-甲基己内酰胺、1,3-二甲基-3,4,5,6-四氢-2(1H)-嘧啶、辛基吡咯烷酮、辛基己内酰胺、1,3-二甲基-2-咪唑啉二酮、N-甲酰基哌啶、N,N′-二甲酰基哌嗪)和酮(例如丙酮、苯乙酮、甲基乙基酮、甲基丁基酮)。
当然也可以在所述溶剂和稀释剂的混合物中进行本发明的方法。
当进行本发明的方法时,反应温度可以在相对宽的范围内变化。通常,所述方法在-30℃至+150℃、优选在-10℃至+100℃的温度下进行。
本发明的方法通常在标准压力下进行。然而,也可以在升高或降低的压力下——通常在0.1bar至15bar的绝对压力下——进行本发明的方法。
为了进行本发明的方法,起始材料通常以近似等摩尔的量使用。然而,也可以相对大过量地使用组分之一。反应通常在反应助剂存在下、任选还在保护气体气氛下(例如在氮气、氩气或氦气下)在合适的稀释剂中进行,并且反应混合物通常在需要的温度下搅拌数小时。通过常规方法进行后处理(参见制备实施例)。
用于进行本发明方法的碱性反应助剂可以为所有适合的缚酸剂。实例包括:碱土金属或碱金属化合物(例如锂、钠、钾、镁、钙和钡的氢氧化物、氢化物、氧化物和碳酸盐),脒碱或胍碱(例如7-甲基-1,5,7-三氮杂二环[4.4.0]癸-5-烯(MTBD);二氮杂二环[4.3.0]壬烯(DBN)、二氮杂二环[2.2.2]辛烷(DABCO)、1,8-二氮杂二环[5.4.0]十一碳烯(DBU)、环己基四丁基胍(CyTBG)、环己基四甲基胍(CyTMG)、N,N,N,N-四甲基-1,8-萘二胺、五甲基哌啶);和胺,尤其是叔胺(例如三乙胺、三甲胺、三苄胺、三异丙胺、三丁胺、三环己基胺、三戊胺、三己胺、N,N-二甲基苯胺、N,N-二甲基甲苯胺、N,N-二甲基-对-氨基吡啶、N-甲基吡咯烷、N-甲基哌啶、N-甲基咪唑、N-甲基吡唑、N-甲基吗啉、N-甲基六亚甲基二胺、吡啶、4-吡咯烷基吡啶、4-二甲基氨基吡啶、喹啉、α-甲基吡啶、β-甲基吡啶、嘧啶、吖啶、N,N,N′,N′-四亚甲基二胺、N,N,N′,N′-四亚乙基二胺、喹喔啉、N-丙基二异丙基胺、N-乙基二异丙基胺、N,N′-二甲基环己胺、2,6-二甲基吡啶、2,4-二甲基吡啶或三乙基二胺(triethyldiamine))。
可用于进行本发明方法的酸性反应助剂包括所有无机酸(例如氢卤酸,如氢氟酸、氢氯酸、氢溴酸或氢碘酸,以及硫酸、磷酸、亚磷酸、硝酸),路易斯酸(例如氯化铝(III)、三氟化硼或其醚合物、氯化钛(IV)、氯化锡(IV))和有机酸(例如甲酸、乙酸、丙酸、丙二酸、乳酸、草酸、富马酸、己二酸、硬脂酸、酒石酸、油酸、甲磺酸、苯甲酸、苯磺酸或对甲苯磺酸)。
此外,本发明还提供式(IV)的中间体
其中结构元素R1、p和G具有构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)中给出的含义且其中Alk代表C1-C4-烷基,优选甲基和乙基且特别优选甲基。
在一个优选的实施方案中,它们为式(IV-1)的中间体
其中结构元素R1和G具有构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)中给出的含义且其中Alk代表C1-C4-烷基,优选甲基或乙基。
本发明还提供式(V)的中间体
其中结构元素R1、p和G具有构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)中给出的含义且其中Y-代表F-、Cl-、Br-、I-、NO3 -、SO4 -、BF4 -或ClO4 -,优选F-、Cl-、Br-、I-或BF4 -且特别优选Br-、Cl-或BF4 -。
在一个优选的实施方案中,它们为式(V-1)的中间体
其中结构元素R1和G具有构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)中给出的含义且其中Y-代表F-、Cl-、Br-、I-或BF4 -,优选Br-、Cl-或BF4 -。
异构体
根据取代基的性质,式(I)的化合物可为几何异构体和/或光学活性异构体或相应的具有不同组成的异构体混合物的形式。这些立体异构体为例如对映异构体、非对映异构体、阻转异构体或几何异构体。因此,本发明包括纯的立体异构体和任何所需的这些异构体的混合物。
方法和用途
本发明还涉及用于防治动物害虫的方法,其中式(I)的化合物可作用于动物害虫和/或其生境。动物害虫的防治优选在农业和林业中、以及在材料保护中进行。这优选排除用于人体或动物体的外科或治疗处理的方法以及在人体或动物体上进行的诊断方法。
本发明还涉及式(I)的化合物作为农药的用途,尤其是作为作物保护组合物的用途。
在本申请的上下文中,术语“农药”在每种情况下通常还包括术语“作物保护组合物”。
式(I)的化合物由于具有良好的植物耐受性、有利的恒温动物毒性和良好的环境相容性而适用于:保护植物和植物器官抵抗生物和非生物胁迫因素、提高采收产率、改善采收材料的品质以及防治在农业、园艺业、畜牧业、水产养殖业、林业、园林和休闲设施、储存产品和材料的保护以及卫生领域中遇到的动物害虫,尤其是昆虫、蛛形纲动物、蠕虫,尤其是线虫和软体动物。
在本专利申请的上下文中,术语“卫生”应被理解为意指旨在预防疾病、特别是感染性疾病并且用于保护人类和动物健康和/或保护环境和/或保持清洁的任何和所有措施、方法和过程。根据本发明,这尤其包括用于清洁、消毒和灭菌如纺织品或硬质表面,特别是由玻璃、木材、水泥、瓷器、陶瓷、塑料或金属(多种金属)制成的表面,以保证它们免于卫生害虫和/或其分泌物的措施。在这方面,本发明的保护范围优选排除用于人体或动物体的外科或治疗处理方法以及在人体或动物体上实施的诊断方法。
术语“卫生领域”包括其中这些卫生措施、方法和过程是重要的所有区域、技术领域和工业应用,例如在厨房、面包房、机场、浴室、游泳池、百货商店、酒店、医院、马厩、动物饲养等中的卫生。
因此,术语“卫生害虫”应理解为意指一种或多种这样的动物害虫:其在卫生领域中的存在是有问题的,特别是出于健康原因。因此,主要目的是避免卫生害虫的存在和/或避免在卫生领域中暴露于这些害虫,或将它们限制在最小的程度。这尤其可以通过使用既可以用于预防感染也可以用于预防已存在的感染的农药来实现。还可以使用预防或减少暴露于害虫的制剂。例如,卫生害虫包括下文提及的生物体。
因此,术语“卫生保护”涵盖维持和/或改善这些卫生措施、预防措施和方法的所有行为。
式(I)的化合物可优选用作农药。其对于通常敏感性和抗性的物种以及对于发育的全部或特定阶段均具有活性。上述害虫包括:
节肢动物门(Arthropoda)、特别是蛛形纲(Arachnida)的害虫,例如粉螨属(例如粗脚粉螨(Acarus siro)、枸杞瘤瘿螨(Aceria kuko)、柑橘瘤瘿螨(Aceria sheldoni))、刺皮瘿螨属(Aculops spp.)、针刺瘿螨属(Aculus spp.)(例如佛氏刺瘿螨(Aculusfockeui)、苹果刺瘿螨(Aculus schlechtendali))、花蜱属(Amblyomma spp.)、山楂叶螨(Amphitetranychus viennensis)、锐缘蜱属(Argas spp.)、牛蜱属(Boophilus spp.)、短须螨属(Brevipalpus spp.)(例如紫红短须螨(Brevipalpus phoenicis))、蚜苔螨(Bryobia graminum)、苜蓿苔螨(Bryobia praetiosa)、刺尾蝎属(Centruroides spp.)、皮螨属(Chorioptes spp.)、鸡皮刺螨(Dermanyssus gallinae)、欧洲屋尘螨(Dermatophagoides pteronyssinus)、美洲屋尘螨(Dermatophagoides farinae)、革蜱属(Dermacentor spp.)、始叶螨属(Eotetranychus spp.)(例如核桃始叶螨(Eotetranychushicoriae))、梨上瘿螨(Epitrimerus pyri)、真叶螨属(Eutetranychus spp.)(例如班氏真叶螨(Eutetranychus banksi))、瘿螨属(Eriophyes spp.)(例如梨瘿螨(Eriophyespyri))、家甜食螨(Glycyphagus domesticus)、红足海镰螯螨(Halotydeus destructor)、半跗线螨属(Hemitarsonemus spp.)(例如茶半跗线螨(Hemitarsonemus latus)(=侧多食跗线螨(Polyphagotarsonemus latus)))、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodesspp.)、毒蛛属(Latrodectus spp.)、斜蛛属(Loxosceles spp.)、秋收恙螨(Neutrombiculaautumnalis)、Nuphersa属、小爪螨属(Oligonychus spp.)(例如跗线螨(Oligonychuscoffeae)、Oligonychus coniferarum、冬青小爪螨(Oligonychus ilicis)、甘蔗小爪螨(Oligonychus indicus)、芒果小爪螨(Oligonychus mangiferus)、草地小爪螨(Oligonychus pratensis)、石榴小爪螨(Oligonychus punicae)、樟小爪螨(Oligonychusyothersi))、钝缘蜱属(Ornithodorus spp)、禽刺螨属(Ornithonyssus spp.)、全爪螨属(Panonychus spp.)(例如柑桔全爪螨(Panonychus citri(=Metatetranychus citri))、苹果全爪螨(Panonychus ulmi(=Metatetranychus ulmi)))、柑桔锈螨(Phyllocoptrutaoleivora)、多趾宽叶螨(Platytetranychus multidigituli)、侧多食跗线螨(Polyphagotarsonemus latus)、痒螨属(Psoroptes spp.)、扇头蜱属(Rhipicephalusspp.)、根螨属(Rhizoglyphus spp.)、疥螨属(Sarcoptes spp.)、中东金蝎(Scorpiomaurus)、狭跗线螨种(Stenotarsonemus spp.)、稻细螨(Steneotarsonemus spinki)、跗线螨属(Tarsonemus spp.)(例如乱跗线螨(Tarsonemus confusus)、樱草狭跗线螨(Tarsonemus pallidus))、叶螨属(Tetranychus spp.)(例如加拿大叶螨(Tetranychuscanadensis)、朱砂叶螨(Tetranychus cinnabarinus)、土耳其斯坦叶螨(Tetranychusturkestani)、二斑叶螨(Tetranychus urticae))、阿氏真恙螨(Trombiculaalfreddugesi)、Vaejovis属、番茄斜背瘤瘿螨(Vasates lycopersici);
唇足纲(Chilopoda)的害虫,例如,地蜈蚣属(Geophilus spp.)、蚰蜓属(Scutigera spp.);
弹尾目或弹尾纲(Collembola)的害虫,例如,武装棘跳虫(Onychiurus armatus);绿圆跳虫(Sminthurus viridis);
倍足纲(Diplopoda)的害虫,例如,千足虫(Blaniulus guttulatus);
昆虫纲的害虫,例如蜚蠊目(Blattodea),如东方蜚蠊(Blattaorientalis)、亚洲蜚蠊(Blattella asahinai)、德国小蠊(Blattella germanica)、马德拉蜚蠊(Leucophaeamaderae)、Loboptera decipiens、家屋斑蠊(Neostylopyga rhombifolia)、古巴蠊属(Panchlora spp.)、木蠊属(Parcoblatta spp.)、大蠊属(Periplaneta spp.)(例如美洲大蠊(Periplaneta americana)、澳洲大蠊(Periplaneta australasiae))、蔗蠊(Pycnoscelus surinamensis)、棕带蜚蠊(Supella longipalpa);
鞘翅目(Coleoptera)的害虫,例如,条纹南瓜甲(Acalymma vittatum)、菜豆象(Acanthoscelides obtectus)、喙丽金龟属(Adoretus spp.)、小蜂窝甲虫(Aethinatumida)、杨树萤叶甲(Agelastica alni)、长吉丁属(Agrilus spp.),例如(白蜡窄吉丁(Agrilus planipennis)、Agrilus coxalis、Agrilus bilineatus、Agrilus anxius)、叩甲属(Agriotes spp.)(例如直条叩头虫(Agriotes linneatus)、小麦叩头虫(Agriotesmancus))、黑菌虫(Alphitobius diaperinus)、马铃薯鳃角金龟(Amphimallonsolstitialis)、家具窃蠹(Anobium punctatum)、星天牛属(Anoplophora spp.)(例如光肩星天牛(Anoplophora glabripennis))、花象属(Anthonomus spp.)(例如棉铃象甲(Anthonomus grandis))、圆皮蠹属(Anthrenus spp.)、梨象属(Apion spp.)、阿鳃金龟属(Apogonia spp.)、隐食甲属(Atomaria spp.)(例如甜菜隐食甲(Atomaria linearis))、毛皮蠹属(Attagenus spp.)、Baris caerulescens、恶条豆象(Bruchidius obtectus)、豆象属(Bruchus spp.)(例如豌豆象(Bruchus pisorum)、蚕豆象(Bruchus rufimanus))、龟叶甲属(Cassida spp.)、菜豆莹叶甲(Cerotoma trifurcata)、龟象属(Ceuthorhynchusspp.)(例如白菜籽龟象(Ceutorrhynchus assimilis)、甘蓝茎龟象(Ceutorrhynchusquadridens)、白菜龟象(Ceutorrhynchus rapae))、跳甲属(Chaetocnema spp.)(例如甘薯跳甲(Chaetocnema confinis)、美国齿跳甲(Chaetocnemadenticulata)、荒地玉米跳甲(Chaetocnema ectypa))、Cleonus mendicus、宽胸叩头虫属(Conoderus spp.)、根颈象属(Cosmopolites spp.)(例如香蕉根颈象甲(Cosmopolites sordidus))、褐新西兰肋翅鳃角金龟(Costelytra zealandica)、叩甲属(Ctenicera spp.)、象虫属(Curculio spp.)(例如美核桃象(Curculio caryae)、大栗象(Curculio caryatrypes)、美洲榛子象(Curculioobtusus)、小栗象(Curculio sayi))、锈赤扁谷盗(Cryptolestes ferrugineus)、长角扁谷盗(Cryptolestes pusillus)、杨干隐喙(Cryptorhynchus lapathi)、芒果果核象甲(Cryptorhynchus mangiferae)、细枝象属(Cylindrocopturus spp.)、密点细枝象(Cylindrocopturus adspersus)、洋松细枝象(Cylindrocopturus furnissi)、大小蠹属(Dendroctonus spp.)(例如中欧山松大小蠹(Dendroctonus ponderosae))、皮蠹属(Dermestes spp.)、叶甲属(Diabrotica spp.)(例如带斑黄瓜条叶甲(Diabroticabalteata)、北方玉米根叶甲(Diabrotica barberi)、南方十一星瓜叶甲(Diabroticaundecimpunctata howardi)、南方十一星瓜叶甲亚种(Diabrotica undecimpunctataundecimpunctata)、西方玉米根叶甲(Diabrotica virgifera virgifera)、墨西哥玉米根叶甲(Diabrotica virgifera zeae))、蛀野螟属(Dichocrocis spp.)、水稻铁甲(Dicladispa armigera)、Diloboderus属、Epicaerus属、食植瓢虫属(Epilachna spp.)(例如瓜食植瓢虫(Epilachna borealis)、墨西哥豆瓢虫(Epilachna varivestis))、毛跳甲属(Epitrix spp.)(例如黄瓜跳甲(Epitrix cucumeris)、茄子跳甲(Epitrix fuscula)、烟草跳甲(Epitrix hirtipennis)、美国马铃薯跳甲(Epitrix subcrinita)、块茎跳甲(Epitrixtuberis))、钻孔虫属(Faustinus spp.)、裸蛛甲(Gibbium psylloides)、阔角谷盗(Gnathocerus cornutus)、菜心野螟(Hellula undalis)、黑异爪蔗金龟(Heteronychusarator)、寡节鳃金龟属(Heteronyx spp.)、Hylamorpha elegans、北美家天牛(Hylotrupesbajulus)、紫苜蓿叶象(Hypera postica)、蓝绿象(Hypomeces squamosus)、咪小蠹属(Hypothenemus spp.)(例如咖啡果小蠹(Hypothenemus hampei)、苹枝小囊(Hypothenemusobscurus)、毛竹小蠹(Hypothenemus pubescens))、甘蔗大褐齿爪鳃金龟(Lachnosternaconsanguinea)、烟草甲(Lasioderma serricorne)、长头谷盗(Latheticus oryzae)、波缘薪甲属(Lathridius spp.)、负泥虫属(Lema spp.)、马铃薯甲虫(Leptinotarsadecemlineata)、潜叶蛾属(Leucoptera spp.)(例如咖啡潜叶蛾(Leucopteracoffeella))、Limonius ectypus、稻根象(Lissorhoptrus oryzophilus)、Listronotus(=Hyperodes)属、筒喙象属(Lixus spp.)、Luperodes属、黄胸寡毛跳甲(Luperomorphaxanthodera)、粉蠹属(Lyctus spp.)、Megacyllene spp.(例如Megacyllene robiniae)、美洲叶甲属(Megascelis spp.)、梳爪叩头虫属(Melanotus spp.)(例如Melanotus longulusoregonensis)、油菜花露尾甲(Meligethes aeneus)、鳃金龟属(Melolontha spp.)(例如欧洲鳃金龟(Melolontha melolontha))、Migdolus属、墨天牛属(Monochamus spp.)、象甲(Naupactus xanthographus)、隐跗郭公虫属(Necrobia spp.)、Neogalerucella属、黄蛛甲(Niptus hololeucus)、椰蛀犀金龟(Oryctes rhinoceros)、锯谷盗(Oryzaephilussurinamensis)、Oryzaphagus oryzae、耳喙象属(Otiorrhynchus spp.)(例如苹果耳喙象(Otiorhynchus cribricollis)、苜蓿耳喙象(Otiorhynchus ligustici)、草莓耳喙象(Otiorhynchus ovatus)、粗糙草莓耳喙象(Otiorhynchus rugosostriarus)、黑葡萄耳喙象(Otiorhynchus sulcatus))、负泥虫属(Oulema spp.)(例如橙足负泥虫(Oulemamelanopus)、稻负泥虫(Oulema oryzae))、小青花金龟(Oxycetonia jucunda)、辣根猿叶虫(Phaedon cochleariae)、食叶鳃金龟属(Phyllophaga spp.)、鳃金龟(Phyllophagahelleri)、黄条跳甲属(Phyllotreta spp.)(例如辣根条跳甲(Phyllotreta armoraciae)、西方黑跳甲(Phyllotreta pusilla)、美条纹跳甲(Phyllotreta ramosa)、黄曲条跳甲(Phyllotreta striolata))、日本弧丽金龟(Popillia japonica)、象甲属(Premnotrypesspp.)、大谷蠹(Prostephanus truncatus)、跳甲属(Psylliodes spp.)(例如马铃薯跳甲(Psylliodes affinis)、油菜兰跳甲(Psylliodes chrysocephala)、忽布跳甲(Psylliodespunctulata))、蛛甲属(Ptinus spp.)、暗色瓢虫(Rhizobius ventralis)、谷蠹(Rhizopertha dominica)、隐喙象属(Rhynchophorus spp.)、红棕象甲(Rhynchophorusferrugineus)、棕榈象甲(Rhynchophorus palmarum)、小蠹属(Scolytusspp.)(例如欧洲榆小蠹(Scolytus multistriatus))、Sinoxylon perforans、谷象属(Sitophilus spp.)(例如谷象(Sitophilus granarius)、罗望子象(Sitophiluslinearis)、米象(Sitophilus oryzae)、玉米象(Sitophilus zeamais))、尖隐喙象属(Sphenophorus spp.)、药材甲(Stegobium paniceum)、茎干象属(Sternechus spp.)(例如豆茎象(Sternechus paludatus))、宽幅天牛属(Symphyletes spp.)、纤毛象属(Tanymecusspp.)(例如双宽隆突纤毛象(Tanymecus dilaticollis)、印度纤毛象(Tanymecusindicus)、红豆草灰象甲(Tanymecus palliatus))、黄粉虫(Tenebrio molitor)、大谷盗(Tenebrioides mauretanicus)、拟谷盗属(Tribolium spp.)(例如美洲黑拟谷盗(Tribolium audax)、赤拟谷盗(Tribolium castaneum)、杂拟谷盗(Triboliumconfusum))、斑皮蠹属(Trogoderma spp.)、籽象属(Tychius spp.)、脊虎天牛属(Xylotrechus spp.)、距步甲属(Zabrus spp.)(例如玉米距步甲(Zabrustenebrioides));
革翅目(Dermaptera)的害虫,例如,肥螋(Anisolabis maritime)、欧洲球螋(Forficula auricularia)、溪岸蠼螋(Labidura riparia);
双翅目(Diptera)的害虫,例如,伊蚊属(Aedes spp.)(例如埃及伊蚊(Aedesaegypti)、白纹伊蚊(Aedes albopictus)、叮刺伊蚊(Aedes sticticus)、骚扰伊蚊(Aedesvexans))、潜蝇属(Agromyza spp.)(例如苜蓿斑潜蝇(Agromyza frontella)、美洲黍潜蝇(Agromyza parvicornis))、按实蝇属(Anastrepha spp.)、按蚊属(Anopheles spp.)(例如四斑按蚊(Anopheles quadrimaculatus)、冈比亚按蚊(Anopheles gambiae))、瘿蚊属(Asphondylia spp.)、果实蝇属(Bactrocera spp.)(例如瓜实蝇(Bactroceracucurbitae)、东方果实蝇(Bactrocera dorsalis)、油橄榄果实蝇(Bactrocera oleae))、花园毛蚊(Bibio hortulanus)、天青丽蝇(Calliphora erythrocephala)、红头丽蝇(Calliphora vicina)、地中海实蝇(Ceratitis capitata)、摇蚊属(Chironomus spp.)、金蝇属(Chrysomya spp.)、斑虻属(Chrysops spp.)、高额麻虻(Chrysozona pluvialis)、锥蝇属(Cochliomya spp.)、康瘿蚊属(Contarinia spp.)(例如葡萄瘿蚊(Contariniajohnsoni)、甘蓝瘿蚊(Contarinia nasturtii)、梨实康瘿蚊(Contarinia pyrivora)、向日葵瘿蚊(Contarinia schulzi)、高粱康瘿蚊(Contarinia sorghicola)、麦黄康癭蚊(Contarinia tritici))、人皮蝇(Cordylobia anthropophaga)、环足摇蚊(Cricotopussylvestris)、库蚊属(Culex spp.)(例如尖音库蚊(Culex pipiens)、致乏库蚊(Culexquinquefasciatus))、库蠓属(Culicoides spp.)、脉毛蚊属(Culiseta spp.)、黄蝇属(Cuterebra spp.)、橄榄大实蝇(Dacus oleae)、叶瘿蚊属(Dasineura spp.)(例如油菜叶瘿蚊(Dasineura brassicae))、地种蝇属(Delia spp.)(例如葱蝇(Delia antiqua)、麦种蝇(Delia coarctata)、毛跗地种蝇(Delia florilega)、灰地种蝇(Delia platura)、甘蓝地种蝇(Delia radicum))、人肤蝇(Dermatobia hominis)、果蝇属(Drosophila spp.)(例如黑腹果蝇(Drosphila melanogaster)、樱桃果蝇(Drosophila suzukii))、稻象属(Echinocnemus spp.)、Euleia heraclei、厕蝇属(Fannia spp.)、胃蝇属(Gastrophilusspp.)、舌蝇属(Glossina spp.)、麻虻属(Haematopota spp.)、毛眼水蝇属(Hydrelliaspp.)、大麦毛眼水蝇(Hydrellia griseola)、黑蝇属(Hylemya spp.)、虱蝇属(Hippoboscaspp.)、皮蝇属(Hypoderma spp.)、斑潜蝇属(Liriomyza spp.)(例如菜斑潜蝇(Liriomyzabrassicae)、南美斑潜蝇(Liriomyza huidobrensis)、美洲斑潜蝇(Liriomyza sativae))、绿蝇属(Lucilia spp.)(例如铜绿蝇(Lucilia cuprina))、罗蛉属(Lutzomyia spp.)、曼蚊属(Mansonia spp.)、家蝇属(Musca spp.)(例如家蝇(Musca domestica)、舍蝇(Muscadomestica vicina))、狂蝇属(Oestrus spp.)、瑞典麦秆蝇(Oscinella frit)、拟长跑摇蚊属(Paratanytarsus spp.)、Paralauterborniella subcincta、泉蝇属(Pegomya或Pegomyia spp.)(例如甜菜泉蝇(Pegomya betae)、天仙子泉蝇(Pegomya hyoscyami)、悬钩子泉蝇(Pegomya rubivora))、白蛉属(Phlebotomus spp.)、草种蝇属(Phorbia spp.)、伏蝇属(Phormia spp.)、酪蝇(Piophilacasei)、Platyparea poeciloptera、Prodiplosis属、胡萝卜茎蝇(Psilarosae)、绕实蝇属(Rhagoletis spp.)(例如东部樱桃实蝇(Rhagoletiscingulata)、核桃绕实蝇(Rhagoletis completa)、黑樱桃实蝇(Rhagoletisfausta)、西部樱桃实蝇(Rhagoletis indifferens)、越桔实蝇(Rhagoletismendax)、苹果实蝇(Rhagoletis pomonella))、麻蝇属(Sarcophaga spp.)、蚋属(Simulium spp.)(例如南方蚋(Simulium meridionale))、螫蝇属(Stomoxys spp.)、虻属(Tabanus spp.)、根斑蝇属(Tetanops spp.)、大蚊属(Tipula spp.)(例如欧洲大蚊(Tipula paludosa)、牧场大蚊(Tipula simplex))、Toxotrypana curvicauda;
半翅目(Hemiptera)的害虫,例如Acizzia acaciaebaileyanae、Acizziadodonaeae、木虱(Acizzia uncatoides)、长头蝗(Acridaturrita)、无网长管蚜属(Acyrthosipon spp.)(例如豌豆长管蚜(Acyrthosiphon pisum))、Acrogonia属、Aeneolamia属、隆脉木虱属(Agonoscena spp.)、刺粉虱属(Aleurocanthus spp.)、欧洲甘蓝粉虱(Aleyrodes proletella)、蔗粉穴粉虱(Aleurolobus barodensis)、棉粉虱(Aleurothrixus floccosus)、植莲木风(Allocaridara malayensis)、芒果叶蝉属(Amrasca spp.)(例如小绿叶蝉(Amrasca bigutulla)、小叶蝉(Amrasca devastans))、圆尾蚜(Anuraphis cardui)、肾圆盾蚧属(Aonidiella spp.)(例如红肾圆盾蚧(Aonidiellaaurantii)、黄肾圆盾蚧(Aonidiella citrina)、苏铁肾盾蚧(Aonidiella inornata))、梨瘤蚜(Aphanostigma piri)、蚜属(Aphis spp)(例如绣线菊蚜(Aphiscitricola)、黑豆蚜(Aphis craccivora)、甜菜蚜(Aphis fabae)、草莓根蚜(Aphis forbesi)、大豆蚜(Aphisglycines)、棉蚜(Aphi sgossypii)、常春藤蚜(Aphis hederae)、葡萄藤蚜(Aphisillinoisensis)、Aphis middletoni、鼠李马铃薯蚜(Aphis nasturtii)、夹竹桃蚜(Aphisnerii)、苹果蚜(Aphis pomi)、卷叶蚜(Aphis spiraecola)、Aphisviburniphila)、葡萄叶蜂(Arboridia apicalis)、Arytainilla属、小圆盾蚧属(Aspidiella spp.)、圆盾蚧属(Aspidiotus spp.)(例如常春藤圆盾蚧(Aspidiotus nerii))、Atanus属、茄沟无网蚜(Aulacorthum solani)、烟粉虱(Bemisia tabaci)、澳大利亚木虱(Blastopsyllaoccidentalis)、Boreioglycaspis melaleucae、李短尾蚜(Brachycaudushelichrysii)、微管姆属(Brachycolus spp.)、甘蓝蚜(Brevicoryne brassicae)、喀木虱属(Cacopsylla spp.)(例如梨木虱(Cacopsylla pyricola))、小褐稻虱(Calligyponamarginata)、Capulinia属、丽黄头大叶蝉(Carneocephala fulgida)、甘蔗绵蚜(Ceratovacunalanigera)、沫蝉科(Cercopidae)、蜡蚧属(Ceroplastes spp.)、草莓钉蚜(Chaetosiphon fragaefolii)、蔗黄雪盾蚧(Chionaspistegalensis)、茶绿叶蜂(Chloritaonukii)、台湾大蝗(Chondracrisrosea)、核桃黑斑蚜(Chromaphis juglandicola)、黑褐圆盾蚧(Chrysomphalus aonidum)、黑褐圆盾蚧(Chrysomphalus ficus)、玉米叶蝉(Cicadulina mbila)、Coccomytilus halli、软蚧属(Coccus spp.)(例如褐软蚧(Coccushesperidum)、长椭圆软蚧(Coccuslongulus)、桔软蜡蚧(Coccus pseudomagnoliarum)、咖啡绿蚧(Coccusviridis))、隐瘤蚜(Cryptomyzus ribis)、Cryptoneossa属、梳木风属(Ctenarytaina spp.)、黄翅叶蝶属(Dalbulus spp.)、Dialeurodeschittendeni、柑橘粉虱(Dialeurodes citri)、柑橘木虱(Diaphorinacitri)、白背盾蚧属(Diaspis spp.)、Diuraphis属、Doralis属、履绵蚧属(Drosicha spp.)、西圆尾蚜属(Dysaphis spp.)(例如锈条蚜(Dysaphis apiifolia)、车前草蚜(Dysaphis plantaginea)、百合西圆尾蚜(Dysaphis tulipae))、灰粉蚧属(Dysmicoccus spp.)、小绿叶蝉属(Empoasca spp.)(例如西部马铃薯叶蝉(Empoasca abrupta)、蚕豆小叶蝉(Empoasca fabae)、苹果小绿叶蝉(Empoasca maligna)、茄微叶蝉(Empoasca solana)、Empoasca stevensi)、绵蚜属(Eriosoma spp.)(例如美洲绵蚜(Eriosoma americanum)、苹果绵蚜(Eriosomalanigerum)、梨根绵蚜(Eriosoma pyricola))、斑叶蝉属(Erythroneura spp.)、Eucalyptolyma属、褐木虱属(Euphyllura spp.)、殃叶蝉(Euscelisbilobatus)、拂粉阶属(Ferrisia spp.)、Fiorinia属、Furcaspis oceanica、咖啡地粉蚧(Geococcus coffeae)、Glycaspis属、银合欢木虱(Heteropsylla cubana)、颊木虱(Heteropsylla spinulosa)、假桃病毒叶蝉(Homalodisca coagulata)、梅大尾蚜(Hyalopterus arundinis)、桃大尾蚜(Hyalopterus pruni)、吹绵蚧属(Icerya spp.)(例如吹绵蚧壳虫(Icerya purchasi))、Idiocerus属、扁喙叶蝉属(Idioscopus spp.)、灰飞虱(Laodelphax striatellus)、蜡蚧属(Lecanium spp.)(例如水土坚蚧(Lecanium corni)(=Parthenolecanium corni))、盾蚧属(Lepidosaphes spp.)(例如榆蛎盾蚧(Lepidosaphes ulmi))、萝卜蚜(Lipaphiserysimi)、日本长白蚧(Lopholeucaspis japonica)、斑衣蜡蝉(Lycorma delicatula)、长管蚜属(Macrosiphum spp.)(例如马铃薯长管蚜(Macrosiphum euphorbiae)、百合长管蚜(Macrosiphum lilii)、蔷薇长管蚜(Macrosiphum rosae))、二点叶蜂(Macrostelesfacifrons)、沫蝶属(Mahanarva spp.)、高粱蚜(Melanaphis sacchari)、Metcalfiella属、Metcalfa pruinosa、麦无网蚜(Metopolophium dirhodum)、黑缘平翅斑蚜(Monelliacostalis)、Monelliopsis pecanis、瘤蚜属(Myzus spp.)(例如冬葱瘤蚜(Myzusascalonicus)、梅瘤蚜(Myzus cerasi)、女贞瘤蚜(Myzus ligustri)、堇菜瘤蚜(Myzus ornatus)、桃蚜(Myzus persicae)、烟蚜(Myzusnicotianae))、莴苣衲长管蚜(Nasonovia ribisnigri)、Neomaskellia属、黑尾叶蝉属(Nephotettix spp.)(例如黑尾叶蝉(Nephotettix cincticeps)、二条黑尾叶蝉(Nephotettix nigropictus))、Nettigoniclla spectra、褐飞虱(Nilaparvata lugens)、Oncometopia属、Ortheziapraelonga、中华稻蝗(Oxya chinensis)、Pachypsylla属、杨梅粉虱(Parabemisiamyricae)、虱啮属(Paratrioza spp.)(例如马铃薯木虱(Paratrioza cockerelli))、片盾蚧属(Parlatoria spp.)、瘿绵蚜属(Pemphigus spp.)(例如囊柄瘿绵蚜(Pemphigusbursarius)、Pemphigus populivenae)、玉米蜡蝉(Peregrinus maidis)、Perkinsiella属、绵粉蚧属(Phenacoccus spp.)(例如美地绵粉蚧(Phenacoccus madeirensis))、杨平翅绵蚜(Phloeomyzus passerinii)、忽布疣蚜(Phorodon humuli)、葡萄根瘤蚜属(Phylloxeraspp.)(例如Phylloxera devastatrix、警根瘤蚜(Phylloxera notabilis))、苏铁褐点并盾蚧(Pinnaspis aspidistrae)、臀纹粉蚧属(Planococcus spp.)(例如橘臀纹粉蚧(Planococcus citri))、Prosopidopsylla flava、梨形原绵腊蚧(Protopulvinariapyriformis)、桑白盾蚧(Pseudaulacaspis pentagona)、粉蚧属(Pseudococcus spp.)(例如柑栖粉蚧(Pseudococcus calceolariae)、康氏粉蚧(Pseudococcus comstocki)、拟长尾粉蚧(Pseudococcus longispinus)、葡萄粉蚧(Pseudococcus maritimus)、暗色粉蚧(Pseudococcus viburni))、Psyllopsis属、木虱属(Psylla spp.)(例如黄杨木虱(Psyllabuxi)、苹木虱(Psylla mali)、梨木虱(Psyllapyri))、金小蜂属(Pteromalus spp.)、桃绵蜡蚧(Pulvinaria spp.)、Pyrilla属、笠圆盾蚧属(Quadraspidiotus spp.)(例如胡桃园盾蚧(Quadraspidiotus juglansregiae)、杨笠圆盾蚧(Quadraspidiotus ostreaeformis)、梨笠盾蚧(Quadraspidiotus perniciosus))、Quesada gigas、平刺粉蚧属(Rastrococcusspp.)、缢管蚜属(Rhopalosiphum spp.)(例如玉米蚜(Rhopalosiphum maidis)、苹草缢管蚜(Rhopalosiphum oxyacanthae)、稻麦蚜(Rhopalosiphum padi)、红腹缢管蚜(Rhopalosiphum rufiabdominale))、黑盔蚧属(Saissetia spp.)(例如咖啡黑盔蚧(Saissetia coffeae)、Saissetia miranda、Saissetia neglecta、黑蜡蚧(Saissetiaoleae))、葡萄带叶蝉(Scaphoideus titanus)、麦二叉蚜(Schizaphis graminum)、苏铁刺圆盾蚧(Selenaspidus articulatus)、Sipha flava、麦长管蚜(Sitobion avenae)、长唇基飞虱属(Sogata spp.)、白背飞虱(Sogatella furcifera)、稻飞风属(Sogatodes spp.)、Stictocephala festina、树粉虱(Siphoninus phillyreae)、Tenalaphara malayensis、Tetragonocephela属、长斑蚜属(Tinocallis caryaefoliae)、广胸沫蝉属(Tomaspisspp.)、声蚜属(Toxoptera spp.)(例如小桔蚜(Toxoptera aurantii)、大桔蚜(Toxopteracitricidus))、温室粉虱(Trialeurodes vaporariorum)、尖翅木虱属(Trioza spp.)(例如柿木虱(Trioza diospyri))、小叶蝉属(Typhlocyba spp.)、尖盾蚧属(Unaspis spp.)、葡萄根瘤蚜(Viteusvitifolii)、么叶蝉属(Zygina spp.);
异翅亚目(Heteroptera)的害虫,例如,Aelia属、南瓜缘蝽(Anasatristis)、拟丽蝽属(Antestiopsis spp.)、Boisea属、土长蝽属(Blissus spp.)、俊盲蝽属(Calocorisspp.)、斑腿微剌盲蝽(Campylommalivida)、异背长蝽属(Cavelerius spp.)、臭虫属(Cimexspp.)(例如Cimex adjunctus、热带臭虫(Cimex hemipterus)、温带臭虫(Cimexlectularius)、蝠臭虫(Cimex pilosellus))、白辧麦寄蝇属(Collaria spp.)、绿盲蝽(Creontiades dilutus)、胡椒缘蝽(Dasynus piperis)、Dichelops furcatus、厚氏长棒网蝽(Diconocoris hewetti)、棉红蝽属(Dysdercus spp.)、美洲蝽属(Euschistus spp.)(例如英雄美洲蝽(Euschistus heros)、褐美洲蝽(Euschistus servus)、三色美洲蝽(Euschistus tristigmus)、三点美洲蝽(Euschistus variolarius))、菜蝽属(Eurydemaspp.)、扁盾蝽属(Eurygaster spp.)、茶翅蝽(Halyomorpha halys)、盲蝽属(Heliopeltisspp.)、Horcias nobilellus、稻缘蝽属(Leptocorisa spp.)、异稻缘蝽(Leptocorisavaricornis)、西部喙缘蝽(Leptoglossus occidentalis)、叶缘缘蝽(Leptoglossusphyllopus)、丽盲蝽属(Lygocoris spp.)(例如原丽盲蝽(Lygocoris pabulinus))、草盲蝽属(Lygus spp.)(例如灰豆草盲蝽(Lygus elisus)、豆荚草盲蝽(Lygus hesperus)、美国牧草盲蝽(Lygus lineolaris))、蔗黑长蝽(Macropes excavatus)、Megacopta cribraria、Miridae、金光绿盲蝽(Monalonion atratum)、绿蝽属(Nezara spp.)(例如稻绿蝽(Nezaraviridula))、Nysius属、稻蝽属(Oebalus spp.)、Pentomidae、方背皮蝽(Piesmaquadrata)、璧蝽属(Piezodorus spp.)(例如盖德拟壁蝽(Piezodorus guildinii))、盲蝽属(Psallus spp.)、Pseudacysta persea、红猎蝽属(Rhodnius spp.)、可可褐盲蝽(Sahlbergella singularis)、Scaptocoris castanea、黑蝽属(Scotinophora spp.)、梨冠网蝽(Stephanitis nashi)、Tibraca属、锥猎蝽属(Triatoma spp.);
膜翅目(Hymenoptera)的害虫,例如,顶切叶蚁属(Acromyrmex spp.)、菜叶蜂属(Athalia spp.)(例如黄翅菜叶蜂(Athalia rosae))、美切叶蚁属(Atta spp.)、弓背蚁属(Camponotus spp.)、Dolichovespula属、松叶蜂属(Diprion spp.)(例如类欧松叶蜂(Diprion similis))、实叶蜂属(Hoplocampa spp.)(例如樱实叶蜂(Hoplocampa cookei)、苹叶蜂(Hoplocampa testudinea))、毛蚁属(Lasius spp.)、阿根廷蚁(Linepithema(Iridiomyrmex)humile)、小家蚁(Monomorium pharaonis)、立毛蚁属(Paratrechinaspp.)、Paravespula属、Plagiolepis属、树蜂属(Sirex spp.)(例如云杉蓝树蜂(Sirexnoctilio))、红火蚁(Solenopsis invicta)、臭蚁属(Tapinoma spp.)、白足狡臭蚁(Technomyrmex albipes)、大树蜂属(Urocerus spp.)、胡蜂属(Vespa spp.)(例如黄边胡蜂(Vespa crabro))、小火蚁(Wasmannia auropunctata)、黑树蜂属(Xeris spp.);
等足目(Isopoda)的害虫,例如,鼠妇(Armadillidium vulgare)、栉水虱(Oniscusasellus)、球鼠妇(Porcellio scaber);
等翅目(Isoptera)的害虫,例如,家白蚁属(Coptotermes spp.)(例如台湾乳白蚁(Coptotermes formosanus))、堆角白蚁(Cornitermes cumulans)、堆砂白蚁属(Cryptotermes spp.)、楹白蚁属(Incisitermes spp.)、木白蚁属(Kalotermes spp.)、稻麦小白蚁(Microtermes obesi)、鼻白蚁属(Nasutitermis spp.)、土白蚁属(Odontotermesspp.)、Porotermes属、散白蚁属(Reticulitermes spp.)(例如黄肢散白蚁(Reticulitermes flavipes)、美国散白蚁(Reticulitermes hesperus));
鳞翅目(Lepidoptera)的害虫,例如,小蜡螟(Achroia grisella)、桑剑纹夜蛾(Acronicta major)、褐带卷蛾属(Adoxophyes spp.)(例如棉褐带卷蛾(Adoxophyesorana))、烦夜蛾(Aedia leucomelas)、地老虎属(Agrotis spp.)(例如黄地老虎(Agrotissegetum)、小地老虎(Agrotis ipsilon))、波纹夜蛾属(Alabama spp.)(例如棉叶波纹夜蛾(Alabama argillacea))、脐橙螟(Amyelois transitella)、条麦蛾属(Anarsia spp.)、干煞夜蛾属(Anticarsia spp.)(例如大豆夜蛾(Anticarsia gemmatalis))、条小卷蛾属(Argyroploce spp.)、苜蓿银纹夜蛾属(Autographa spp.)、甘蓝夜蛾(Barathrabrassicae)、苹髓尖蛾(Blastodacna atra)、籼弄蝶(Borbo cinnara)、棉潜蛾(Bucculatrix thurberiella)、松尺蠖(Bupalus piniarius)、蛀褐夜蛾属(Busseolaspp.)、卷叶蛾属(Cacoecia spp.)、茶细蛾(Caloptilia theivora)、烟卷蛾(Capuareticulana)、苹果小卷蛾(Carpocapsa pomonella)、桃蛀果蛾(Carposina niponensis)、冬尺蛾(Cheimatobia brumata)、禾草螟属(Chilo spp.)(例如Chilo plejadellus、二化螟(Chilo suppressalis))、Choreutis pariana、色卷蛾属(Choristoneura spp.)、Chrysodeixis chalcites、葡萄果蠹蛾(Clysia ambiguella)、纵卷叶野螟属(Cnaphalocerus spp.)、稻纵卷叶野螟(Cnaphalocrocis medinalis)、云卷蛾属(Cnephasia spp.)、茶枝尖细蛾属(Conopomorpha spp.)、球颈象属(Conotrachelusspp.)、Copitarsia属、小卷蛾属(Cydia spp.)(例如豆荚小卷蛾(Cydia nigricana)、苹果蠹蛾(Cydia pomonella))、Dalaca noctuides、绢野螟属(Diaphaniaspp.)、Diparopsis属、小蔗杆草螟(Diatraea saccharalis)、梢斑螟属(Dioryctria spp.)(例如Dioryctriazimmermani)、钻夜蛾属(Earias spp.)、Ecdytolopha aurantium、南美玉米苗斑螟(Elasmopalpus lignosellus)、甘薯杆螟(Eldana saccharina)、粉斑螟属(Ephestiaspp.)(例如烟草粉斑螟(Ephestia elutella)、地中海斑螟(Ephestia kuehniella))、叶小卷蛾属(Epinotia spp.)、苹淡褐卷蛾(Epiphyas postvittana)、Erannis属、亚洲胡桃蛾(Erschoviella musculana)、荚斑螟属(Etiella spp.)、Eudocima属、棕卷蛾属(Euliaspp.)、女贞细卷蛾(Eupoecilia ambiguella)、毒蛾属(Euproctis spp.)(例如黄毒蛾(Euproctis chrysorrhoea))、切夜蛾属(Euxoa spp.)、脏切夜蛾属(Feltia spp.)、大蜡螟(Galleria mellonella)、细蛾属(Gracillaria spp.)、小食心虫属(Grapholitha spp.)(例如梨小食心虫(Grapholita molesta)、杏小食心虫(Grapholita prunivora))、甘蔗螟属(Hedylepta spp.)、铃夜蛾属(Helicoverpa spp.)(例如棉铃虫(Helicoverpaarmigera)、玉米夜蛾(Helicoverpa zea))、实夜蛾属(Heliothis spp.)(例如烟芽夜蛾(Heliothis virescens))、褐织蛾(Hofmannophila pseudospretella)、同斑螟属(Homoeosoma spp.)、长卷蛾属(Homona spp.)、苹果巢蛾(Hyponomeuta padella)、柿举枝蛾(Kakivoria flavofasciata)、亮灰蝶属(Lampides spp.)、贪夜蛾属(Laphygma spp.)、蠹食心虫(Laspeyresia molesta)、茄白翅野螟(Leucinodes orbonalis)、纹潜蛾属(Leucoptera spp.)(例如咖啡潜叶蛾(Leucoptera coffeella))、潜叶细蛾属(Lithocolletis spp.)(例如苹果斑幕潜叶蛾(Lithocolletis blancardella))、绿果冬夜蛾(Lithophane antennata)、花翅小蛾属(Lobesia spp.)(例如葡萄花翅小卷蛾(Lobesiabotrana))、豆白隆切根虫(Loxagrotis albicosta)、毒蛾属(Lymantria spp.)(例如舞毒蛾(Lymantria dispar))、潜蛾属(Lyonetia spp.)(例如桃潜叶蛾(Lyonetiaclerkella))、黄褐天幕毛虫(Malacosoma neustria)、豆荚野螟(Maruca testulalis)、甘蓝夜蛾(Mamstra brassicae)、稻暮眼蝶(Melanitis leda)、毛胫夜蛾属(Mocis spp.)、Monopis obviella、粘虫(Mythimna separata)、橡长角蛾(Nemapogon cloacellus)、水螟属(Nymphula spp.)、Oiketicus属、楸属(Omphisa spp.)、Operophtera属、麦秆夜蛾属(Oria spp.)、瘤丛螟属(Orthaga spp.)、秆野螟属(Ostrinia spp.)(例如欧洲玉米螟(Ostrinia nubilalis))、小眼夜蛾(Panolis flammea)、稻弄蝶属(Parnara spp.)、红铃虫属(Pectinophora spp.)(例如棉红铃虫(Pectinophora gossypiella))、潜跳甲属(Perileucoptera spp.)、茄麦蛾属(Phthorimaea spp.)(例如马铃薯麦蛾(Phthorimaeaoperculella))、桔潜蛾(Phyllocnistis citrella)、小潜细蛾属(Phyllonorycter spp.)(例如金纹小潜细蛾(Phyllonorycterblancardella)、山楂潜叶蛾(Phyllonoryctercrataegella))、粉蝶属(Pieris spp.)(例如菜粉蝶(Pieris rapae))、荷兰石竹小卷蛾(Platynota stultana)、印度谷斑螟(Plodia interpunctella)、金翅夜蛾属(Plusiaspp.)、菜蛾(Plutella xylostella)(=钻石背蛾(Plutella maculipennis))、Podesiaspp.(例如Podesia syringae)、小白巢蛾属(Prays spp.)、斜纹夜蛾属(Prodenia spp.)、烟草天蛾属(Protoparce spp.)、粘虫属(Pseudaletia spp.)(例如一星粘虫(Pseudaletiaunipuncta))、大豆尺夜蛾(Pseudoplusia includens)、玉米螟(Pyrausta nubilalis)、薄荷灰夜蛾(Rachiplusia nu)、禾螟属(Schoenobius spp.)(例如三化螟(Schoenobiusbipunctifer))、白禾螟属(Scirpophaga spp.)(例如稻白螟(Scirpophaga innotata))、黄地老虎(Scotia segetum)、茎夜蛾属(Sesamia spp.)(例如大螟(Sesamia inferens))、长须卷蛾属(Sparganothis spp.)、灰翅夜蛾属(Spodoptera spp.)(例如Spodopteraeradiana、甜菜夜蛾(Spodoptera exigua)、草地贪夜蛾(Spodoptera frugiperda)、Spodoptera praefica)、展足蛾属(Stathmopoda spp.)、Stenoma属、花生麦蛾(Stomopteryx subsecivella)、透翅蛾属(Synanthedon spp.)、安第斯马铃薯块茎蛾(Tecia solanivora)、异舟蛾属(Thaumetopoea spp.)、大豆夜蛾(Thermesiagemmatalis)、木塞谷蛾(Tinea cloacella)、袋谷蛾(Tinea pellionella)、幕谷蛾(Tineola bisselliella)、卷蛾属(Tortrix spp.)、毛毡衣蛾(Trichophaga tapetzella)、粉夜蛾属(Trichoplusia spp.)(例如粉纹夜蛾(Trichoplusia ni))、三化螟(Tryporyzaincertulas)、番茄斑潜蝇(Tuta absoluta)、灰蝶属(Virachola spp.);
直翅目(Orthoptera)或跳跃目(Saltatoria)的害虫,例如,家蟋蟀(Achetadomesticus)、Dichroplus属、蝼蛄属(Gryllotalpa spp.)(例如欧洲蝼蛄(Gryllotalpagryllotalpa))、蔗蝗属(Hieroglyphus spp.)、飞蝗属(Locusta spp.)(例如飞蝗(Locustamigratoria))、黑蝗属(Melanoplus spp.)(例如迁飞黑蝗(Melanoplus devastator)、Paratlanticus ussuriensis)、沙漠蝗(Schistocerca gregaria);
虱目(Phthiraptera)的害虫,例如,例如畜虱属(Damalinia spp.)、血虱属(Haematopinus spp.)、毛虱属(Linognathus spp.)、虱属(Pediculus spp.)、根瘤蚜(Phylloxera vastatrix)、阴虱(Ptirus pubis)、啮毛虱属(Trichodectes spp.);
啮虫目(Psocoptera)的害虫,例如,粉啮虫属(Lepinatus spp.)、书虱属(Liposcelis spp.);
蚤目(Siphonaptera)的害虫,例如,角叶蚤属(Ceratophyllus spp.)、栉头蚤属(Ctenocephalides spp.)(例如犬栉头蚤(Ctenocephalides canis),猫栉头蚤(Ctenocephalides felis))、跳蚤(Pulex irritans)、穿皮潜蚤(Tunga penetrans)、印鼠客蚤(Xenopsylla cheopis);
缨翅目(Thysanoptera)的害虫,例如,玉米黄呆蓟马(Anaphothrips obscurus)、稻蓟马(Baliothrips biformis)、Chaetanaphothrips leeuweni、葡萄镰蓟马(Drepanothris reuteri)、Enneothrips flavens、花蓟马属(Frankliniella spp.)(例如烟褐蓟马(Frankliniella fusca)、西花蓟马(Frankliniella occidentalis)、苏花蓟马(Frankliniella schultzei)、麦花蓟马(Frankliniella tritici)、越桔花蓟马(Frankliniella vaccinii)、威廉期花蓟马(Frankliniella williamsi))、蓟马属(Haplothrips spp.)、阳蓟马属(Heliothrips spp.)、温室条篱蓟马(Hercinothripsfemoralis)、卡蓟马属(Kakothrips spp.)、葡萄蓟马(Rhipiphorothrips cruentatus)、硬蓟马属(Scirtothripsspp.)、小豆蘧带蓟马(Taeniothrips cardamomi)、蓟马属(Thripsspp.)(例如棕榈蓟马(Thrips palmi)、烟蓟马(Thrips tabaci));
衣鱼目(Zygentoma)(=缨尾亚目(Thysanura))的害虫,例如,栉衣鱼属(Ctenolepisma spp.)、衣鱼(Lepisma saccharina)、盗火虫(Lepismodes inquilinus)、家衣鱼(Thermobia domestica);
综合纲(Symphyla)的害虫,例如,幺蚰属(Scutigerella spp.)(例如无斑点幺蚰(Scutigerella immaculata));
软体动物门(Mollusca)的害虫,例如双壳纲(Bivalvia)的害虫,如饰贝属(Dreissena spp.),
以及腹足纲(Gastropoda)的害虫,如阿勇蛞蝓属(Arion spp.)(例如黑红阿勇蛞蝓(Arion ater rufus))、双脐螺属(Biomphalaria spp.)、小泡螺属(Bulinus spp.)、野蛞蝓属(Deroceras spp.)(例如田灰蛞蝓(Deroceras laeve))、土蜗属(Galba spp.)、椎实螺属(Lymnaea spp.)、钉螺属(Oncomelania spp.)、福寿螺属(Pomaceaspp.)、琥珀螺属(Succinea spp.);
线虫纲(Nematoda)的植物害虫,即植物寄生性线虫,尤其是野外垫刃线虫属(Aglenchus spp.)(例如居农野外垫刃线虫(Aglenchus agricola))、粒线虫属(Anguinaspp.)(例如小麦粒线虫(Anguina tritici))、滑刃线虫属(Aphelenchoides spp.)(例如花生滑刃线虫(Aphelenchoides arachidis)、草莓滑刃线虫(Aphelenchoides fragariae))、刺线虫属(Belonolaimus spp.)(例如细小刺线虫(Belonolaimus gracilis)、长尾刺线虫(Belonolaimus longicaudatus)、诺顿刺线虫(Belonolaimus nortoni))、伞滑刃线虫属(Bursaphelenchus spp.)(例如椰子红环腐线虫(Bursaphelenchus cocophilus)、荒漠伞滑刃线虫(Bursaphelenchus eremus)、松材线虫(Bursaphelenchus xylophilus))、坏死线虫属(Cacopaurus spp.)(例如瘟疫坏死线虫(Cacopaurus pestis))、小环线虫属(Criconemella spp.)(例如弯曲小环线虫(Criconemella curvata)、刻线小环线虫(Criconemella onoensis)、装饰小环线虫(Criconemella ornata)、畸形小环线虫(Criconemella rusium)、薄叶小环线虫(Criconemella xenoplax(=环腐线虫(Mesocriconema xenoplax))))、轮线虫属(Criconemoides spp.)(例如Criconemoidesferniae、Criconemoides onoense、Criconemoides ornatum)、双垫刃属(Ditylenchusapp.)(例如续断双垫刃线虫(Ditylenchus dipsaci))、锥线虫属(Dolichodorus spp.)、球异皮线虫属(Globodera spp.)(例如马铃薯白线虫(Globoderapallida)、马铃薯金线虫(Globodera rostochiensis))、螺旋线虫属(Helicotylenchus spp.)(例如双宫螺旋线虫(Helicotylenchusdihystera))、半轮线虫属(Hemicriconemoides spp.)、鞘线虫属(Hemicycliophora spp.)、异皮线虫属(Heterodera spp.)(例如燕麦胞囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heteroderaschachtii))、Hirschmaniella属、纽带线虫属(Hoplolaimus spp.)、长针线虫属(Longidorus spp.)(例如非洲长针线虫(Longidorus africanus))、根结线虫属(Meloidogyne spp.)(例如哥伦比亚根结线虫(Meloidogyne chitwoodi)、伪根结线虫(Meloidogyne fallax)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyneincognita))、瓢线虫属(Meloinema spp.)、珍珠线虫属(Nacobbus spp.)、拟茎线虫属(Neotylenchus spp.)、拟长针线虫属(Paralongidorus spp.)、拟滑刃线虫属(Paraphelenchus spp.)、拟毛刺线虫属(Paratrichodorus spp.)(例如次拟毛刺线虫(Paratrichodorus minor))、针线虫属(Paratylenchus spp.)、短体线虫属(Pratylenchusspp.)(例如穿刺短体线虫(Pratylenchus penetrans))、Pseudohalenchus属、平滑垫刃属(Psilenchus spp.)、斑皮胞囊线虫属(Punctodera spp.)、五沟线虫属(Quinisulciusspp.)、穿孔线虫属(Radopholus spp.)(例如柑桔穿孔线虫(Radopholus citrophilus)、香蕉穿孔线虫(Radopholus similis))、肾状线虫属(Rotylenchulus spp.)、盘旋线虫属(Rotylenchus spp.)、盾线虫属(Scutellonema spp.)、亚蛇形线虫属(Subanguina spp.)、毛刺线虫属(Trichodorus spp.)(例如短粗根毛刺线虫(Trichodorus obtusus)、原始毛刺线虫(Trichodorus primitivus))、矮化线虫属(Tylenchorhynchus spp.)(例如饰环矮化线虫(Tylenchorhynchus annulatus))、麦线虫属(Tylenchulus spp.)(例如柑桔根线虫(Tylenchulus semipenetrans))、剑线虫属(Xiphinema spp.)(例如标准剑线虫(Xiphinema index))。
在一定的浓度或施用率下,还可视情况地将式(I)的化合物用作除草剂、安全剂、生长调节剂或改善植物特性的试剂,用作杀微生物剂或杀配子剂,例如用作杀真菌剂、抗霉菌剂、杀细菌剂、杀病毒剂(包括对抗类病毒的试剂)或用作对抗MLO(类支原体生物)和RLO(类立克次氏体生物)的试剂。视情况,还可将其用作用于合成其他活性化合物的中间体或前体。
制剂
本发明还涉及作为农药的包含至少一种式(I)化合物的制剂和由其制备的施用形式,例如浇灌、滴注和喷洒液体。任选地,施用形式包含其他农药和/或改善作用的佐剂,例如渗透剂,例如植物油(如油菜籽油、向日葵油)、矿物油(如石蜡油)、植物脂肪酸的烷基酯(如油菜籽油甲酯或大豆油甲酯)、或烷醇烷氧基化物;和/或展着剂(spreader),例如烷基硅氧烷和/或盐(如有机或无机铵盐或鏻盐,例如硫酸铵或磷酸氢二铵);和/或保留促进剂,例如磺基丁二酸二辛酯或羟丙基瓜尔胶聚合物;和/或湿润剂,例如甘油;和/或肥料,例如含铵、含钾或含磷的肥料。
常规的制剂为,例如水溶性液体剂(SL)、乳液浓缩剂(EC)、水包乳剂(EW)、悬浮浓缩剂(SC、SE、FS、OD)、水分散性颗粒剂(WG)、颗粒剂(GR)和胶囊浓缩剂(CS);这些制剂和其他可能的制剂类型例如被国际作物生命组织(Crop Life International)记载并在以下文献中描述:《农药标准》、《联合国粮农组织(FAO)和世界卫生组织(WHO)农药标准制订和使用手册》、《联合国粮农组织(FAO)植物生产与保护文件-173》(由联合国粮农组织(FAO)/世界卫生组织(WHO)农药标准联席会议编写,2004,ISBN:9251048576)。除了一种或多种式(I)的化合物外,所述制剂还任选地包含其他农用化学活性化合物。
优选的是包含下述物质的制剂或施用形式:助剂,如增量剂、溶剂、自发性促进剂、载体、乳化剂、分散剂、防冻剂、杀生物剂(biocide)、增稠剂;和/或其他助剂,如佐剂。在本发明的上下文中,佐剂是增强制剂的生物功效的组分,而该组分本身不具有任何生物功效。佐剂的实例为促进保留、铺展、附着到叶面或渗透的试剂。
这些制剂以已知方式制备,例如通过将式(I)的化合物与助剂如增量剂、溶剂和/或固体载体和/或其他助剂如表面活性剂混合而制备。所述制剂在合适的设备中制备或在施用前或施用过程中制备。
所用助剂可为适于向式(I)的化合物的制剂或由所述制剂制备的施用形式(如即用型农药,如喷雾液体或拌种剂产品)赋予特定特性(例如某些物理、技术和/或生物特性)的物质。
合适的增量剂为例如水、极性和非极性有机化学液体,例如选自:芳族烃和非芳族烃(如石蜡、烷基苯、烷基萘、氯苯)、醇和多元醇(如果合适的话,其还可被取代、醚化和/或酯化)、酮(如丙酮、环己酮)、酯(包括脂肪和油)和(聚)醚,简单和取代的胺、酰胺、内酰胺(如N-烷基吡咯烷酮)和内酯、砜和亚砜(如二甲基亚砜)。
如果所用的增量剂是水,则还可使用例如有机溶剂作为助溶剂。有用的液体溶剂主要为:芳族化合物,如二甲苯、甲苯或烷基萘;氯代芳族化合物或氯代脂族烃,如氯苯、氯乙烯或二氯甲烷;脂族烃,如环己烷或链烷烃,如石油馏分、矿物油和植物油;醇,如丁醇或乙二醇及其醚和酯;酮,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,如二甲基甲酰胺和二甲基亚砜;以及水。
原则上,可使用所有合适的溶剂。合适的溶剂的实例为:芳族烃,如二甲苯、甲苯或烷基萘;氯代芳族烃或氯代脂族烃,如氯苯、氯乙烯或二氯甲烷;脂族烃,如环己烷、链烷烃、石油馏分、矿物油和植物油;醇,如甲醇、乙醇、异丙醇、丁醇或乙二醇及其醚和酯;酮,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,如二甲基亚砜;以及水。
原则上,可使用所有合适的载体。更具体而言,合适的载体包括以下物质:例如铵盐和精细研磨的天然岩石,如高岭土、氧化铝、滑石、白垩、石英、绿坡缕石、蒙脱石或硅藻土;和精细研磨的合成岩石,如高度分散的二氧化硅、氧化铝和天然或合成的硅酸盐;树脂;蜡;和/或固体肥料。同样可使用这些载体的混合物。用于颗粒剂的有用载体包括:例如,压碎并分级的天然岩石,如方解石、大理石、浮石、海泡石、白云石;以及无机粉和有机粉的合成颗粒;以及有机材料的颗粒,如锯屑、纸、椰壳、玉米穗轴和烟草茎。
还可使用液化的气体增量剂或溶剂。特别合适的增量剂或载体是在标准温度和大气压下为气态的那些,例如,气溶胶推进剂(aerosolpropellant),如卤代烃,以及丁烷、丙烷、氮气和二氧化碳。
具有离子或非离子性质的乳化剂和/或发泡剂(foam former)、分散剂或润湿剂、或这些表面活性物质的混合物的实例为:聚丙烯酸的盐;木质素磺酸的盐;苯酚磺酸或萘磺酸的盐;环氧乙烷与脂肪醇或与脂肪酸或与脂肪胺、与取代的酚(优选烷基酚或芳基酚)的缩聚物;磺基丁二酸酯的盐;牛磺酸衍生物(优选牛磺酸烷基酯);聚乙氧基化醇或酚的磷酸酯;多元醇的脂肪酸酯;以及含硫酸根、磺酸根和磷酸根的化合物的衍生物,例如烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐、蛋白质水解产物、木质素亚硫酸盐废液和甲基纤维素。如果式(I)的化合物之一和/或惰性载体之一不溶于水并且如果施用在水中进行时,则表面活性剂的存在是有利的。
可存在于制剂和由其获得的施用形式中的其他助剂包括:染料,例如无机颜料,如氧化铁、氧化钛和普鲁士蓝;和有机染料,如茜素染料、偶氮染料和金属酞菁染料;以及营养物和微量营养物,如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
可以存在的其他组分为稳定剂,如低温稳定剂、防腐剂、抗氧化剂、光稳定剂或其他提高化学和/或物理稳定性的试剂。还可存在发泡剂(Foam generator)和消泡剂。
此外,制剂和由其获得的施用形式还可包含下述物质作为另外的助剂:粘着剂,如羧甲基纤维素;以及呈粉末、颗粒或胶乳形式的天然和合成的聚合物,如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯;和天然磷脂,如脑磷脂和卵磷脂;和合成磷脂。其他助剂可为矿物油和植物油。
如果合适的话,在制剂和由其获得的施用形式中还可以存在其他助剂。这些添加剂的实例为香料、保护胶体、粘合剂、胶粘剂、增稠剂、触变剂、渗透剂、保留促进剂、稳定剂、螯合剂、络合组合物、润湿剂、展着剂。通常,式(I)的化合物可与通常用于制剂目的的任何固体或液体添加剂组合。
有用的保留促进剂包括所有那些降低动态表面张力的物质(如磺基丁二酸二辛酯)或增加粘弹性的物质(如羟丙基瓜尔胶聚合物)。
在本发明的上下文中,有用的渗透剂为所有那些通常用于改善农用化学活性化合物向植物内渗透的物质。在本发明的上下文中,渗透剂通过这样的方式定义:其从(通常水性)施用液体和/或从喷洒涂层渗透到植物的表皮,从而增加活性化合物在表皮中的移动性的能力。文献(Baur等人,1997,Pesticide Science 51,131-152)中记载的方法可用于测定这种特性。实例包括:醇烷氧基化物,如椰子脂肪乙氧基化物(10)或异十三烷基乙氧基化物(12);脂肪酸酯,如油菜籽油甲酯或大豆油甲酯;脂肪胺烷氧基化物,如牛油胺乙氧基化物(15);或铵盐和/或鏻盐,如硫酸铵或磷酸氢二铵。
所述制剂优选包含0.00000001重量%至98重量%的式(I)的化合物,更优选0.01重量%至95重量%的式(I)的化合物,最优选0.5重量%至90重量%的式(I)的化合物,基于所述制剂的重量计。
在由制剂制备的施用形式(尤其是农药)中,式(I)的化合物的含量可在宽的范围内变化。在使用形式中,式(I)的化合物的浓度通常可为0.00000001重量%至95重量%的式(I)的化合物,优选为0.00001重量%至1重量%,基于施用形式的重量计。以适合于施用形式的常规方式进行施用。
混合物
式(I)的化合物还可与一种或多种合适的如下物质混合使用:杀真菌剂、杀细菌剂、杀螨剂、杀软体动物剂、杀线虫剂、杀昆虫剂、微生物剂、有益生物体、除草剂、肥料、驱鸟剂、phytotonic、止繁殖剂、安全剂、化学信息素和/或植物生长调节剂,从而例如拓宽作用谱、延长作用时间、提高作用速率、防止排斥或防止抗性发展。另外,这类活性化合物组合可以改善植物生长和/或对非生物因素的耐受性,如对高温或低温、对干旱或对高水含量或土壤盐度的耐受性。还可改善开花和结果性能、优化发芽能力和根系发育、促进采收和提高产量、影响熟化、改善采收产品的品质和/或营养价值、延长储存期和/或改善采收产品的可加工性。
此外,式(I)的化合物可与其他活性化合物或化学信息素如引诱剂和/或驱鸟剂和/或植物活化剂和/或生长调节剂和/或肥料混合存在。同样地,式(I)的化合物可用于改善植物性能如采收材料的生长、产量和品质。
在本发明的一个特别的实施方案中,式(I)的化合物与其他化合物(优选下文所述的那些化合物)混合存在于制剂或由这些制剂制备的施用形式中。
如果下文提到的化合物之一可以以不同的互变异构形式存在,则这些形式也被包括在内,即使在各种情况下没有被明确提及。视情况,如果所提及的所有混合组分基于其官能团能够形成盐,则还可与合适的碱或酸形成盐。
杀昆虫剂/杀螨剂/杀线虫剂
本文中以其“通用名称”提及的活性化合物是已知的,并且记载于例如“农药手册(The Pesticide Manual)”(第16版,British CropProtection Council 2012)中,或者可以在互联网(例如http://www.alanwood.net/pesticides)上检索到。该分类以提交该专利申请时适用的IRAC作用方式分类方案为基础。
(1)乙酰胆碱酯酶(AChE)抑制剂,例如氨基甲酸酯类,例如棉铃威(alanycarb)、涕灭威(aldicarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮砜威(butoxycarboxim)、胺甲萘(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、乙硫苯威(ethiofencarb)、仲丁威(fenobucarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混杀威(trimethacarb)、灭除威(XMC)和灭杀威(xylylcarb);或有机磷酸酯类,例如乙酰甲胺磷(acephate)、甲基吡噁磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、甲基谷硫磷(azinphos-methyl)、硫线磷(cadusafos)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、甲基毒死蜱(chloropyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、苯硫磷(EPN)、乙硫磷(ethion)、灭线磷(ethoprophos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟松(fenitrothion)、倍硫磷(fenthion)、噻唑磷(fosthiazate)、庚烯磷(heptenophos)、氰咪唑硫磷(imicyafos)、异柳磷(isofenphos)、O-(甲氧基氨基硫代磷酰基)水杨酸异丙酯、异噁唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、亚砜磷(oxydemeton-methyl)、对硫磷甲酯(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、肟硫磷(phoxim)、甲基吡啶磷(pirimiphos-methyl)、丙溴磷(profenofos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、丁基吡啶磷(tebupirimfos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(triclorfon)和蚜灭磷(vamidothion)。
(2)GABA-门控氯化物通道阻断剂,例如环戊二烯有机氯类,例如氯丹(chlordane)和硫丹(endosulfan);或苯基吡唑类(fiproles),例如乙虫腈(ethiprole)和氟虫腈(fipronil)。
(3)钠通道调节剂,例如拟除虫菊酯(pyrethroid)类,例如氟丙菊酯(acrinathrin)、丙烯除虫菊酯(allethrin)、d-顺式-反式丙烯除虫菊酯(d-cis-transallethrin)、d-反式丙烯除虫菊酯(d-transallethrin)、联苯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、生物烯丙菊酯S-环戊烯基异构体(bioallethrin S-cyclopentenylisomer)、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、β-氟氯氰菊酯(beta-cyfluthrin)、氯氟氰菊酯(cyhalothrin)、λ-氯氟氰菊酯(lambda-cyhalothrin)、γ-氯氟氰菊酯(gamma-cyhalothrin)、氯氰菊酯(cypermethrin)、α-氯氰菊酯(alpha-cypermethrin)、β-氯氰菊酯(beta-cypermethrin)、θ-氯氰菊酯(theta-cypermethrin)、ζ-氯氰菊酯(zeta-cypermethrin)、苯醚氰菊酯[(1R)-反式异构体](cyphenothrin[(1R)-trans isomers])、溴氰菊酯(deltamethrin)、右旋烯炔菊酯[(EZ)-(1R)异构体](empenthrin[(EZ)-(1R)isomers])、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、氰戊菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、τ-氟胺氰菊酯(tau-fluvalinate)、苄螨醚(halfenprox)、炔咪菊酯(imiprothrin)、噻嗯菊酯(kadethrin)、甲氧苄氟菊酯(momfluorothrin)、苄氯菊酯(permethrin)、苯醚菊酯[(1R)-反式异构体](phenothrin[(1R)-trans isomer])、炔丙菊酯(prallethrin)、除虫菊酯(pyrethrine、pyrethrum)、苄呋菊酯(resmethrin)、氟硅菊酯(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、胺菊酯[(1R)异构体)](tetramethrin[(1R)isomers])、四溴菊酯(tralomethrin)和四氟苯菊酯(transfluthrin);或DDT;或甲氧氯。
(4)烟碱乙酰胆碱受体(nAChR)竞争调节剂,例如新烟碱类(neonicotinoids),例如啶虫脒(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、噻虫啉(thiacloprid)和噻虫嗪(thiamethoxam)或尼古丁(nicotine)或氟啶虫胺腈(sulfoxaflor)或氟吡呋喃酮(flupyradifurone)。
(5)烟碱乙酰胆碱受体(nAChR)变构调节剂,例如多杀菌素类(spinosyns),如乙基多杀菌素(spinetoram)和多杀菌素(spinosad)。
(6)谷氨酸门控氯化物通道(GluCl)变构调节剂,例如,阿凡曼维菌素类/米尔倍霉素类(avermectins/milbemycins),例如阿巴克丁(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectin benzoate)、雷皮菌素(lepimectin)和灭螨菌素(milbemectin)。
(7)保幼激素模仿物,例如,保幼激素类似物如烯虫乙酯(hydroprene)、烯虫炔酯(kinoprene)和烯虫酯(methoprene)或苯氧威(fenoxycarb)或蚊蝇醚(pyriproxyfen)。
(8)其他非特异性(多位点)抑制剂,例如烷基卤化物,例如甲基溴化物和其他烷基卤化物;或氯化苦(chloropicrin)或硫酰氟或硼砂或吐酒石(tartar emetic)或异氰酸甲酯生成剂,如棉隆(diazomet)或威百亩(metam)。
(9)弦音器官调节剂,例如吡蚜酮(pymetrozine)或氟啶虫酰胺(flonicamide)。
(10)螨生长抑制剂,例如四螨嗪(clofentezine)、噻螨酮(hexythiazox)和氟螨嗪(diflovidazin)或乙螨唑(etoxazole)。
(11)昆虫肠膜的微生物干扰剂,例如苏云金芽孢杆菌以色列亚种(Bacillusthuringiensis subspecies israelensis)、球形芽孢杆菌(Bacillus sphaericus)、苏云金芽胞杆菌鲇泽亚种(Bacillus thuringiensis subspecies aizawai)、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subspecies kurstaki)、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subspecies tenebrionis)和B.t.植物蛋白:Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、VIP3A、mCry3A、Cry3Ab、Cry3Bb、Cry34Ab1/35Ab1。
(12)线粒体ATP合成酶的抑制剂,例如ATP干扰剂,例如丁醚脲或有机锡化合物,例如三唑锡、三环锡和苯丁锡(fenbutatin oxide)或快螨特(propargite)或四氯杀螨砜(tetradifon)。
(13)通过阻断质子梯度的氧化磷酸化的解偶联剂,例如虫螨腈(chlorfenapyr)、二硝甲酚(DNOC)和氟虫胺(sulphluramid)。
(14)烟碱乙酰胆碱受体通道阻断剂,例如杀虫磺(bensultap)、杀螟丹盐酸盐(cartap hydrochloride)、杀虫环(thiocyclam)和杀虫双(thiosultap-sodium)。
(15)几丁质生物合成抑制剂,0型,例如双三氟虫脲(bistrifluron)、定虫隆(chlofluazuron)、二氟苯隆(diflubenzuron)、氟环脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氯芬奴隆(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、氟苯脲(teflubenzuron)和杀铃脲(triflumuron)。
(16)几丁质生物合成抑制剂,1型,例如噻嗪酮(buprofezin)。
(17)蜕皮干扰剂(特别是对于双翅目(Diptera)),例如灭蝇胺(cyromazine)。
(18)蜕皮激素受体激动剂,例如环虫酰胺(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)和虫酰肼(tebufenozide)。
(19)章鱼胺受体激动剂,例如双甲脒(amitraz)。
(20)线粒体复合物III电子传递抑制剂,例如氟蚁腙(hydramethylnone),或灭螨醌(acequinocyl),或嘧螨酯(fluacrypyrim)。
(21)线粒体复合物I电子传递抑制剂,例如METI杀螨剂,例如喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨灵(pyridaben)、吡螨胺(tebufenpyrad)和唑虫酰胺(tolfenpyrad);或鱼藤酮(rotenone)(鱼藤)。
(22)电压依赖型钠通道阻断剂,例如茚虫威(indoxacarb)或氰氟虫腙(metaflumizone)。
(23)乙酰基CoA羧化酶的抑制剂,例如特窗酸(tetronic acid)和特特拉姆酸(tetramic acid)衍生物,例如螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)和螺虫乙酯(spirotetramat)。
(24)线粒体复合物IV电子传递抑制剂,例如膦类,如磷化铝、磷化钙、膦和磷化锌;或氰化物,如氰化钙、氰化钾和氰化钠。
(25)线粒体复合物II电子传递抑制剂,如β-酮腈衍生物,例如腈吡螨酯(cyenopyrafen)和丁氟螨酯(cyflumetofen)和甲酰苯胺,如pyflubumide。
(28)鱼尼丁受体调节剂,例如二酰胺类,如氯虫苯甲酰胺(chlorantraniliprole)、溴氰虫酰胺(cyantraniliprole)和氟虫双酰胺(flubendiamide);
其他活性化合物,例如afidopyropen、阿福拉纳(afoxolaner)、印楝素(azadirachtin)、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、broflanilide、溴螨酯(bromopropylate)、灭螨锰(chinomethionat)、chloroprallethrin、冰晶石(cryolite)、环溴虫酰胺(cyclaniliprole)、环氧虫啶(cycloxaprid)、氯氟氰虫酰胺(cyhalodiamide)、dicloromezotiaz、三氯杀螨醇(dicofol)、ε-甲氧苄氟菊酯(epsilonmetofluthrin)、epsilon momfluthrin、flometoquin、三氟咪啶酰胺(fluazaindolizine)、氟噻虫砜(fluensulfone)、嘧虫胺(flufenerim)、氟菌螨酯(flufenoxystrobin)、丁虫腈(flufiprole)、fluhexafon、氟吡菌酰胺(fluopyram)、氟雷拉纳(fluralaner)、fluxametamide、呋喃虫酰肼(fufenozide)、戊吡虫胍(guadipyr)、右旋七氟甲醚菊酯(heptafluthrin)、氯噻啉(imidaclothiz)、异菌脲(iprodione)、κ-联苯菊酯(kappabifenthrin)、κ-七氟菊酯(kappa tefluthrin)、lotilaner、氯氟醚菊酯(meperfluthrin)、哌虫啶(paichongding)、三氟甲吡醚(pyridalyl)、氟虫吡喹(pyrifluquinazon)、嘧螨胺(pyriminostrobin)、spirobudiclofen、四氟醚菊酯(tetramethylfluthrin)、氟氰虫酰胺(tetraniliprole)、氟氰虫酰胺(tetrachlorantraniliprole)、tioxazafen、硫氟肟醚(thiofluoximate)、triflumezopyrim和碘甲烷(iodomethane);以及基于坚强芽孢杆菌(Bacillus firmus,I-1582,BioNeem,Votivo)的制品,以及下列化合物:1-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯基}-3-(三氟甲基)-1H-1,2,4-三唑-5-胺(由WO2006/043635已知)(CAS885026-50-6)、{1'-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]-5-氟螺[吲哚-3,4'-哌啶]-1(2H)-基}(2-氯吡啶-4-基)甲酮(由WO2003/106457已知)(CAS637360-23-7)、2-氯-N-[2-{1-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]哌啶-4-基}-4-(三氟甲基)苯基]异烟酰胺(由WO2006/003494已知)(CAS872999-66-1)、3-(4-氯-2,6-二甲基苯基)-4-羟基-8-甲氧基-1,8-二氮杂螺[4.5]癸-3-烯-2-酮(由WO 2010052161已知)(CAS 1225292-17-0)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-2-氧代-1,8-二氮杂螺[4.5]癸-3-烯-4-基乙基碳酸酯(由EP 2647626已知)(CAS-1440516-42-6)、4-(丁-2-炔-1-基氧基)-6-(3,5-二甲基哌啶-1-基)-5-氟嘧啶(由WO2004/099160已知)(CAS792914-58-0)、PF1364(由JP2010/018586已知)(CAS登记号1204776-60-2)、N-[(2E)-1-[(6-氯吡啶-3-基)甲基]吡啶-2(1H)-亚基]-2,2,2-三氟乙酰胺(由WO2012/029672已知)(CAS 1363400-41-2)、(3E)-3-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-1,1,1-三氟丙-2-酮(由WO2013/144213已知)(CAS 1461743-15-6)、N-[3-(苄基氨基甲酰基)-4-氯苯基]-1-甲基-3-(五氟乙基)-4-(三氟甲基)-1H-吡唑-5-甲酰胺(由WO2010/051926已知)(CAS 1226889-14-0)、5-溴-4-氯-N-[4-氯-2-甲基-6-(甲基氨基甲酰基)苯基]-2-(3-氯-2-吡啶基)吡唑-3-甲酰胺(由CN103232431已知)(CAS1449220-44-3)、4-[5-(3,5-二氯苯基)-4,5-二氢-5-(三氟甲基)-3-异噁唑基]-2-甲基-N-(顺式-1-氧-3-硫杂环丁基)苯甲酰胺、4-[5-(3,5-二氯苯基)-4,5-二氢-5-(三氟甲基)-3-异噁唑基]-2-甲基-N-(反式-1-氧-3-硫杂环丁基)苯甲酰胺和4-[(5S)-5-(3,5-二氯苯基)-4,5-二氢-5-(三氟甲基)-3-异噁唑基]-2-甲基-N-(顺式-1-氧-3-硫杂环丁基)苯甲酰胺(由WO 2013/050317 A1已知)(CAS 1332628-83-7)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亚磺酰基]丙酰胺、(+)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亚磺酰基]丙酰胺和(-)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亚磺酰基]丙酰胺(由WO 2013/162715 A2、WO2013/162716 A2、US 2014/0213448 A1已知)(CAS 1477923-37-7)、5-[[(2E)-3-氯-2-丙烯-1-基]氨基]-1-[2,6-二氯-4-(三氟甲基)苯基]-4-[(三氟甲基)亚磺酰基]-1H-吡唑-3-甲腈(由CN 101337937 A已知)(CAS1105672-77-2)、3-溴-N-[4-氯-2-甲基-6-[(甲基氨基)硫代甲基]苯基]-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺、(Liudaibenjiaxuanan,由CN103109816A已知)(CAS 1232543-85-9);N-[4-氯-2-[[(1,1-二甲基乙基)氨基]羰基]-6-甲基苯基]-1-(3-氯-2-吡啶基)-3-(氟甲氧基)-1H-吡唑-5-甲酰胺(由WO 2012/034403 A1已知)(CAS 1268277-22-0)、N-[2-(5-氨基-1,3,4-噻二唑-2-基)-4-氯-6-甲基苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺(由WO 2011/085575 A1已知)(CAS 1233882-22-8)、4-[3-[2,6-二氯-4-[(3,3-二氯-2-丙烯-1-基)氧基]苯氧基]丙氧基]-2-甲氧基-6-(三氟甲基)嘧啶(由CN 101337940 A已知)(CAS 1108184-52-6);(2E)-和2(Z)-2-[2-(4-氰基苯基)-1-[3-(三氟甲基)苯基]亚乙基]-N-[4-(二氟甲氧基)苯基]肼甲酰胺(由CN101715774 A已知)(CAS1232543-85-9);环丙烷羧酸3-(2,2-二氯乙烯基)-2,2-二甲基-4-(1H-苯并咪唑-2-基)苯基酯(由CN 103524422 A已知)(CAS 1542271-46-4);(4aS)-7-氯-2,5-二氢-2-[[(甲氧基羰基)[4-[(三氟甲基)硫代]苯基]氨基]羰基]茚并[1,2-e][1,3,4]噁二嗪-4a(3H)-羧酸甲酯(由CN 102391261A已知)(CAS 1370358-69-2);6-脱氧-3-O-乙基-2,4-二-O-甲基-1-[N-[4-[1-[4-(1,1,2,2,2-五氟乙氧基)苯基]-1H-1,2,4-三唑-3-基]苯基]氨基甲酸酯]-α-L-吡喃甘露糖(由US 2014/0275503 A1已知)(CAS1181213-14-8);8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基哒嗪-3-基)-3-氮杂二环[3.2.1]辛烷(CAS 1253850-56-4)、(8-反式)-8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基哒嗪-3-基)-3-氮杂二环[3.2.1]辛烷(CAS 933798-27-7)、(8-顺)-8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基哒嗪-3-基)-3-氮杂二环[3.2.1]辛烷(由WO2007040280 A1、WO 2007040282 A1已知)(CAS 934001-66-8)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)硫代]丙酰胺(由WO 2015/058021 A1、WO2015/058028 A1已知)(CAS1477919-27-9)和N-[4-(氨基硫代甲基)-2-甲基-6-[(甲基氨基)羰基]苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺(由CN 103265527 A已知)(CAS 1452877-50-7)。
杀真菌剂
本文通过其通用名称提及的活性化合物是已知的,并且例如记载于“农药手册”(第16版,British Crop Protection Council)中或可在互联网(例如:http:// www.alanwood.net/pesticides)上检索到。
在类别(1)至(15)中提及的所有混合组分可视情况与合适的碱或酸形成盐,如果它们基于其官能团能够形成盐的话。所提及的类别(1)至(15)中的所有杀真菌混合组分可视情况包括互变异构形式。
1)麦角甾醇生物合成抑制剂,例如(1.001)环丙唑醇(cyproconazole)、(1.002)苯醚甲环唑(difenoconazole)、(1.003)氟环唑(epoxiconazole)、(1.004)环酰菌胺(fenhexamide)、(1.005)苯锈啶(fenpropidin)、(1.006)丁苯吗啉(fenpropimorph)、(1.007)胺苯吡菌酮(fenpyrazamine)、(1.008)氟喹唑(fluquinconazole)、(1.009)粉唑醇(flutriafol)、(1.010)烯菌灵(imazalil)、(1.011)烯菌灵硫酸盐(imazalil sulfate)、(1.012)种菌唑(ipconazole)、(1.013)叶菌唑(metconazole)、(1.014)腈菌唑(myclobutanil)、(1.015)多效唑(paclobutrazol)、(1.016)咪鲜胺(prochloraz)、(1.017)丙环唑(propiconazole)、(1.018)丙硫菌唑(prothioconazole)、(1.019)啶菌唑(pyrisoxazole)、(1.020)螺环菌胺(spiroxamine)、(1.021)戊唑醇(tebuconazole)、(1.022)氟醚唑(tetraconazole)、(1.023)三唑醇(triadimenol)、(1.024)克啉菌(tridemorph)、(1.025)灭菌唑(triticonazole)、(1.026)(1R,2S,5S)-5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.027)(1S,2R,5R)-5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.028)(2R)-2-(1-氯环丙基)-4-[(1R)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇(1.029)(2R)-2-(1-氯环丙基)-4-[(1S)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.030)(2R)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.031)(2S)-2-(1-氯环丙基)-4-[(1R)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.032)(2S)-2-(1-氯环丙基)-4-[(1S)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.033)(2S)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.034)(R)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(1.035)(S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(1.036)[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(1.037)1-({(2R,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧戊环-2-基}甲基)-1H-1,2,4-三唑、(1.038)1-({(2S,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧戊环-2-基}甲基)-1H-1,2,4-三唑、(1.039)1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.040)1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.041)1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.042)2-[(2R,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.043)2-[(2R,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.044)2-[(2R,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.045)2-[(2R,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.046)2-[(2S,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.047)2-[(2S,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.048)2-[(2S,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.049)2-[(2S,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.050)2-[1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.051)2-[2-氯-4-(2,4-二氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.052)2-[2-氯-4-(4-氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.053)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.054)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)戊-2-醇、(1.055)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.056)2-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.057)2-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.058)2-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.059)5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.060)5-(烯丙基硫基(allylsulfanyl))-1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.061)5-(烯丙基硫基)-1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.062)5-(烯丙基硫基)-1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.063)N'-(2,5-二甲基-4-{[3-(1,1,2,2-四氟乙氧基)苯基]硫基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(1.064)N'-(2,5-二甲基-4-{[3-(2,2,2-三氟乙氧基)苯基]硫基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(1.065)N'-(2,5-二甲基-4-{[3-(2,2,3,3-四氟丙氧基)苯基]硫基}苯基)-N-乙基-N-甲基甲亚氨基甲酰胺、(1.066)N'-(2,5-二甲基-4-{[3-(五氟乙氧基)苯基]硫基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(1.067)N'-(2,5-二甲基-4-{3-[(1,1,2,2-四氟乙基)硫基]苯氧基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(1.068)N'-(2,5-二甲基-4-{3-[(2,2,2-三氟乙基)硫基]苯氧基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(1.069)N'-(2,5-二甲基-4-{3-[(2,2,3,3-四氟丙基)硫基]苯氧基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(1.070)N'-(2,5-二甲基-4-{3-[(五氟乙基)硫基]苯氧基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(1.071)N'-(2,5-二甲基-4-苯氧基苯基)-N-乙基-N-甲基亚氨基甲酰胺、(1.072)N'-(4-{[3-(二氟甲氧基)苯基]硫基}-2,5-二甲基苯基)-N-乙基-N-甲基亚氨基甲酰胺、(1.073)N'-(4-{3-[(二氟甲基)硫基]苯氧基}-2,5-二甲基苯基)-N-乙基-N-甲基亚氨基甲酰胺、(1.074)N'-[5-溴-6-(2,3-二氢-1H-茚-2-基氧基)-2-甲基吡啶-3-基]-N-乙基-N-甲基亚氨基甲酰胺、(1.075)N'-{4-[(4,5-二氯-1,3-噻唑-2-基)氧基]-2,5-二甲基苯基}-N-乙基-N-甲基亚氨基甲酰胺、(1.076)N'-{5-溴-6-[(1R)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(1.077)N'-{5-溴-6-[(1S)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(1.078)N'-{5-溴-6-[(顺式-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(1.079)N'-{5-溴-6-[(反式-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(1.080)N'-{5-溴-6-[1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(1.081)氯氟醚菌唑(mefentrifluconazole)、(1.082)ipfentrifluconazole。
2)呼吸链复合物I或II的抑制剂,例如(2.001)苯并烯氟菌唑(benzovindiflupyr)、(2.002)联苯吡菌胺(bixafen)、(2.003)啶酰菌胺(boscalid)、(2.004)萎锈灵(carboxin)、(2.005)氟吡菌酰胺(fluopyram)、(2.006)氟酰胺(flutolanil)、(2.007)氟唑菌酰胺(fluxapyroxad)、(2.008)呋吡菌胺(furametpyr)、(2.009)噻吩酰菌酮(isofetamid)、(2.010)吡唑萘菌胺(isopyrazam)(反式差向异构对映异构体1R,4S,9S)、(2.011)吡唑萘菌胺(反式差向异构对映异构体1S,4R,9R)、(2.012)吡唑萘菌胺(反式差向异构外消旋体1RS,4SR,9SR)、(2.013)吡唑萘菌胺(顺式差向异构外消旋体1RS,4SR,9RS和反式差向异构外消旋体1RS,4SR,9SR的混合物)、(2.014)吡唑萘菌胺(顺式差向异构对映异构体1R,4S,9R)、(2.015)吡唑萘菌胺(顺式差向异构对映异构体1S,4R,9S)、(2.016)吡唑萘菌胺(顺式差向异构外消旋体1RS,4SR,9RS)、(2.017)氟唑菌苯胺(penflufen)、(2.018)吡噻菌胺(penthiopyrad)、(2.019)氟唑菌酰羟胺(pydiflumetofen)、(2.020)pyraziflumid、(2.021)氟唑环菌胺(sedaxane)、(2.022)1,3-二甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.023)1,3-二甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.024)1,3-二甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.025)1-甲基-3-(三氟甲基)-N-[2'-(三氟甲基)联苯-2-基]-1H-吡唑-4-甲酰胺、(2.026)2-氟-6-(三氟甲基)-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)苯甲酰胺、(2.027)3-(二氟甲基)-1-甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.028)3-(二氟甲基)-1-甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.029)3-(二氟甲基)-1-甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.030)3-(二氟甲基)-N-(7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1-甲基-1H-吡唑-4-甲酰胺、(2.031)3-(二氟甲基)-N-[(3R)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(2.032)3-(二氟甲基)-N-[(3S)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(2.033)5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺、(2.034)N-(2-环戊基-5-氟苄基-)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.035)N-(2-叔丁基-5-甲基苄基-)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.036)N-(2-叔丁基苄基-)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.037)N-(5-氯-2-乙基苄基-)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.038)N-(5-氯-2-异丙基苄基-)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.039)N-[(1R,4S)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.040)N-[(1S,4R)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.041)N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.042)N-[2-氯-6-(三氟甲基)苄基-]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.043)N-[3-氯-2-氟-6-(三氟甲基)苄基-]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.044)N-[5-氯-2-(三氟甲基)苄基-]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.045)N-环丙基-3-(二氟甲基)-5-氟-1-甲基-N-[5-甲基-2-(三氟甲基)苄基-]-1H-吡唑-4-甲酰胺、(2.046)N-环丙基-3-(二氟甲基)-5-氟-N-(2-氟-6-异丙基苄基-)-1-甲基-1H-吡唑-4-甲酰胺、(2.047)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基-5-甲基苄基-)-1-甲基-1H-吡唑-4-甲酰胺、(2.048)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基苄基-)-1-甲基-1H-吡唑-4-硫代甲酰胺、(2.049)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基苄基-)-1-甲基-1H-吡唑-4-甲酰胺、(2.050)N-环丙基-3-(二氟甲基)-5-氟-N-(5-氟-2-异丙基苄基-)-1-甲基-1H-吡唑-4-甲酰胺、(2.051)N-环丙基-3-(二氟甲基)-N-(2-乙基-4,5-二甲基苄基-)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.052)N-环丙基-3-(二氟甲基)-N-(2-乙基-5-氟苄基-)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.053)N-环丙基-3-(二氟甲基)-N-(2-乙基-5-甲基苄基-)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.054)N-环丙基-N-(2-环丙基-5-氟苄基-)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.055)N-环丙基-N-(2-环丙基-5-甲基苄基-)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.056)N-环丙基-N-(2-环丙基苄基-)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺。
3)呼吸链复合物III的抑制剂,例如(3.001)唑嘧菌胺(ametoctradin)、(3.002)安美速(amisulbrom)、(3.003)腈嘧菌酯(azoxystrobin)、(3.004)甲香菌酯(coumethoxystrobin)、(3.005)丁香菌酯(coumoxystrobin)、(3.006)氰霜唑(cyazofamid)、(3.007)醚菌胺(dimoxystrobin)、(3.008)烯肟菌酯(enoxastrobin)、(3.009)噁唑菌酮(famoxadon)、(3.010)咪唑菌酮(fenamidon)、(3.011)氟菌螨酯(flufenoxystrobin)、(3.012)氟嘧菌酯(fluoxastrobin)、(3.013)醚菌酯(kresoxim-methyl)、(3.014)苯氧菌胺(metominostrobin)、(3.015)肟醚菌胺(orysastrobin)、(3.016)啶氧菌酯(picoxystrobin)、(3.017)唑菌胺酯(pyraclostrobin)、(3.018)唑胺菌酯(pyrametostrobin)、(3.019)唑胺菌酯(pyraoxystrobin)、(3.020)肟菌酯(trifloxystrobin)、(3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯基乙烯基]氧基}苯基)亚乙基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺、(3.022)(2E,3Z)-5-{[1-(4-氯苯基)-1H-吡唑-3-基]氧基}-2-(甲氧基亚氨基)-N,3-二甲基戊-3-烯酰胺、(3.023)(2R)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺、(3.024)(2S)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺、(3.025)(3S,6S,7R,8R)-8-苄基-3-[({3-[(异丁酰氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧杂环壬烷-7-基2-甲基丙酸酯、(3.026)2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺、(3.027)N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰胺基-2-羟基苯甲酰胺、(3.028)(2E,3Z)-5-{[1-(4-氯-2-氟苯基)-1H-吡唑-3-基]氧基}-2-(甲氧基亚氨基)-N,3-二甲基戊-3-烯酰胺、(3.029)-[甲基{5-[3-(2,4-二甲基苯基)-1H-吡唑-1-基]-2-甲基苄基}氨基甲酸酯。
4)有丝分裂和细胞分裂抑制剂,例如(4.001)多菌灵(carbendazim)、(4.002)乙霉威(diethofencarb)、(4.003)噻唑菌胺(ethaboxam)、(4.004)氟吡菌胺(fluopicolide)、(4.005)戊菌隆(pencycuron)、(4.006)噻苯咪唑(thiabendazole)、(4.007)甲基硫菌灵(thiophanate-methyl)、(4.008)苯酰菌胺(zoxamide)、(4.009)3-氯-4-(2,6-二氟苯基)-6-甲基-5-苯基哒嗪、(4.010)3-氯-5-(4-氯苯基)-4-(2,6-二氟苯基)-6-甲基哒嗪、(4.011)3-氯-5-(6-氯吡啶-3-基)-6-甲基-4-(2,4,6-三氟苯基)哒嗪、(4.012)4-(2-溴-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.013)4-(2-溴-4-氟苯基)-N-(2-溴-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.014)4-(2-溴-4-氟苯基)-N-(2-溴苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.015)4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.016)4-(2-溴-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.017)4-(2-溴-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.018)4-(2-氯-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.019)4-(2-氯-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.020)4-(2-氯-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.021)4-(2-氯-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.022)4-(4-氯苯基)-5-(2,6-二氟苯基)-3,6-二甲基哒嗪、(4.023)N-(2-溴-6-氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.024)N-(2-溴苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.025)N-(4-氯-2,6-二氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺。
5)能够具有多位点活性的化合物,例如(5.001)波尔多液(Bordeaux mixture)、(5.002)敌菌丹(captafol)、(5.003)克菌丹(captan)、(5.004)百菌清(chlorothalonil)、(5.005)氢氧化铜、(5.006)环烷酸铜(copper naphthenate)、(5.007)氧化铜、(5.008)氧氯化铜(copper oxychloride)、(5.009)硫酸铜(2+)(copper(2+)sulfate)、(5.010)二噻农(dithianon)、(5.011)多果定(dodine)、(5.012)灭菌丹(folpet)、(5.013)代森锰锌(mancozeb)、(5.014)代森锰(maneb)、(5.015)代森联(metiram)、(5.016)代森联锌(zincmetiram)、(5.017)喹啉铜(copper oxine)、(5.018)丙森锌(propineb)、(5.019)硫和硫制剂(包括多硫化钙)、(5.020)福美双(thiram)、(5.021)代森锌(zineb)、(5.022)福美锌(ziram)、(5.023)6-乙基-5,7-二氧代-6,7-二氢-5H-吡咯并[3’,4’:5,6][1,4]二噻英并[2,3-c][1,2]噻唑-3-甲腈。
6)能够触发宿主防御的化合物,例如(6.001)苯并噻二唑(acibenzolar-S-methyl)、(6.002)异噻菌胺(isotianil)、(6.003)烯丙苯噻唑(probenazole)、(6.004)噻酰菌胺(tiadinil)。
7)氨基酸和/或蛋白质生物合成抑制剂,例如(7.001)嘧菌环胺(cyprodinil)、(7.002)春雷霉素(kasugamycin)、(7.003)春雷霉素盐酸盐水合物(kasugamycinhydrochloride hydrate)、(7.004)土霉素(oxytetracycline)、(7.005)嘧霉胺(pyrimethanil)、(7.006)3-(5-氟-3,3,4,4-四甲基-3,4-二氢异喹啉-1-基)喹啉。
8)ATP生成抑制剂,例如(8.001)硅噻菌胺(silthiofam)。
9)细胞壁合成抑制剂,例如(9.001)苯噻菌胺(benthiavalicarb)、(9.002)烯酰吗啉(dimethomorph)、(9.003)氟吗啉(flumorph)、(9.004)缬霉威(iprovalicarb)、(9.005)双炔酰菌胺(mandipropamid)、(9.006)丁吡吗啉(pyrimorph)、(9.007)缬菌胺(valifenalate)、(9.008)(2E)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮、(9.009)(2Z)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮。
10)脂和膜合成抑制剂,例如(10.001)霜霉威(propamocarb)、(10.002)霜霉威盐酸盐(propamocarb hydrochloride)、(10.003)甲基立枯磷(tolclofos-methyl)。
11)黑色素生物合成抑制剂,例如(11.001)三环唑(tricyclazole)、(11.002){3-甲基-1-[(4-甲基苯甲酰基)氨基]丁-2-基}氨基甲酸2,2,2-三氟乙基酯。
12)核酸合成抑制剂,例如(12.001)苯霜灵(benalaxyl)、(12.002)高效苯霜灵(benalaxyl-M)(kiralaxyl)、(12.003)甲霜灵(metalaxyl)、(12.004)高效甲霜灵(metalaxyl-M)(mefenoxam)。
13)信号转导抑制剂,例如(13.001)咯菌腈(fludioxonil)、(13.002)异菌脲(iprodione)、(13.003)腐霉利(procymidone)、(13.004)丙氧喹啉(proquinazid)、(13.005)喹氧灵(quinoxyfen)、(13.006)乙烯菌核利(vinclozolin)。
14)能作为解偶联剂的化合物,例如(14.001)氟啶胺(fluazinam)、(14.002)消螨多(meptyldinocap)。
15)其他化合物,例如(15.001)脱落酸(abscisic acid)、(15.002)苯噻硫氰(benthiazole)、(15.003)bethoxazin、(15.004)卡巴西霉素(capsimycin)、(15.005)香芹酮(carvone)、(15.006)灭螨锰(chinomethionat)、(15.007)硫杂灵(cufraneb)、(15.008)环氟菌胺(cyflufenamid)、(15.009)霜脲氰(cymoxanil)、(15.010)环丙磺酰胺(cyprosulfamide)、(15.011)flutianil、(15.012)三乙膦酸铝(fosetyl-aluminium)、(15.013)乙膦酸钙(fosetyl-calcium)、(15.014)乙膦酸钠(fosetyl-sodium)、(15.015)异硫氰酸甲酯(methyl isothiocyanate)、(15.016)苯菌酮(metrafenone)、(15.017)灭粉霉素(mildiomycin)、(15.018)游霉素(natamycin)、(15.019)二甲基二硫代氨基甲酸镍(nickel dimethyldithiocarbamate)、(15.020)酞菌酯(nitrothal-isopropyl)、(15.021)oxamocarb、(15.022)oxathiapiprolin、(15.023)oxyfenthiin、(15.024)五氯苯酚(pentachlorophenol)及盐、(15.025)磷酸及其盐、(15.026)霜霉威-乙膦酸盐(propamocarb-fosetylate)、(15.027)pyriofenone(chlazafenone)(15.028)tebufloquin、(15.029)叶枯酞(tecloftalam)、(15.030)甲磺菌胺(tolnifanide)、(15.031)1-(4-{4-[(5R)-5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.032)1-(4-{4-[(5S)-5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.033)2-(6-苄基-吡啶-2-基)喹唑啉、(15.034)2,6-二甲基-1H,5H-[1,4]二噻英并[2,3-c:5,6-c']二吡咯-1,3,5,7(2H,6H)-四酮、(15.035)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.036)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氯-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.037)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氟-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.038)2-[6-(3-氟-4-甲氧基苯基)-5-甲基吡啶-2-基]喹唑啉、(15.039)2-{(5R)-3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯、(15.040)2-{(5S)-3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯、(15.041)2-{2-[(7,8-二氟-2-甲基喹啉-3-基)氧基]-6-氟苯基}丙-2-醇、(15.042)2-{2-氟-6-[(8-氟-2-甲基喹啉-3-基)氧基]苯基}丙-2-醇、(15.043)2-{3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯、(15.044)2-{3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}苯基甲磺酸酯、(15.045)2-苯基苯酚及其盐、(15.046)3-(4,4,5-三氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、(15.047)3-(4,4-二氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、(15.048)4-氨基-5-氟嘧啶-2-醇(互变异构形式:4-氨基-5-氟嘧啶-2(1H)-酮)、(15.049)4-氧代-4-[(2-苯基乙基)氨基]丁酸、(15.050)5-氨基-1,3,4-噻二唑-2-硫醇、(15.051)5-氯-N'-苯基-N'-(丙-2-炔-1-基)噻吩2-磺酰肼、(15.052)5-氟-2-[(4-氟苄基)氧基]嘧啶-4-胺、(15.053)5-氟-2-[(4-甲基苄基)氧基]嘧啶-4-胺、(15.054)9-氟-2,2-二甲基-5-(喹啉-3-基)-2,3-二氢-1,4-苯并氧杂吖庚因、(15.055){6-[({[(Z)-(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸丁-3-炔-1-基酯、(15.056)(2Z)-3-氨基-2-氰基-3-苯基丙烯酸乙酯、(15.057)吩嗪-1-甲酸、(15.058)3,4,5-三羟基苯甲酸丙酯、(15.059)喹啉-8-醇、(15.060)喹啉-8-醇硫酸酯(2:1)、(15.061){6-[({[(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁酯、(15.062)5-氟-4-亚氨基-3-甲基-1-[(4-甲基苯基)磺酰基]-3,4-二氢嘧啶-2(1H)-酮。
作为混合组分的生物农药
式(I)的化合物可与生物农药组合。
生物农药尤其包括细菌、真菌、酵母菌、植物提取物和由微生物形成的产物,包括蛋白质和次级代谢物。
生物农药包括细菌如产芽孢细菌(spore-forming bacteria)、根定殖细菌(root-colonizing bacteria)和作为生物杀昆虫剂、杀真菌剂或杀线虫剂起作用的细菌。
用作或可用作生物农药的这类细菌的实例为:
解淀粉芽孢杆菌(Bacillus amyloliquefaciens),菌株FZB42(DSM231179);或蜡样芽胞杆菌(Bacillus cereus),尤其是蜡样芽孢杆菌菌株CNCM I-1562;或者坚强芽孢杆菌(Bacillus firmus),菌株I-1582(登录号CNCMI-1582);或短小芽胞杆菌(Bacilluspumilus),尤其是菌株GB34(登录号ATCC 700814)和菌株QST2808(登录号NRRLB-30087);或枯草芽孢杆菌(Bacillus subtilis),尤其是菌株GB03(登录号ATCC SD-1397),或枯草芽孢杆菌菌株QST713(登录号NRRL B-21661)或枯草芽孢杆菌菌株OST 30002(登录号NRRLB-50421);苏云金芽孢杆菌(Bacillus thuringiensis),尤其是苏云金杆菌以色列亚种(B.thuringiensis subspecies israelensis)(血清型H-14)、菌株AM65-52(登录号ATCC1276),或苏云金杆菌鲇泽亚种(B.thuringiensis subsp.aizawai),尤其是菌株ABTS-1857(SD-1372),或苏云金杆菌库尔斯塔克亚种(B.thuringiensis subsp.kurstaki)菌株HD-1,或苏云金杆菌粉虫变种(thuringiensis subsp.tenebrionis)菌株NB 176(SD-5428);侵入巴斯德氏芽菌(Pasteuria penetrans)、巴斯德氏芽菌属(Pasteuria spp.)(肾形肾状线虫(Rotylenchulus reniformis nematode))-PR3(登录号ATCCSD-5834);细黄链霉菌(Streptomyces microflavus)菌株AQ6121(=QRD 31.013,NRRL B-50550);鲜黄链霉菌(Streptomyces galbus)菌株AQ 6047(登录号NRRL 30232)。
用作或可用作生物农药的真菌和酵母菌的实例为:
巴西安白僵菌(Beauveria bassiana),尤其是菌株ATCC 74040;盾壳霉(Coniothyrium minitans),尤其是菌株CON/M/91-8(登录号DSM-9660);轮枝孢属(Lecanicillium spp.),尤其是菌株HRO LEC12;蜡蚧轮枝菌(Lecanicillium lecanii),(以前称为Verticillium lecanii),尤其是菌株KV01;金龟子绿僵菌(Metarhiziumanisopliae),尤其是菌株F52(DSM3884/ATCC 90448);梅奇酵母菌(Metschnikowiafructicola),尤其是菌株NRRL Y-30752;玫烟色拟青霉(Paecilomyces fumosoroseus)(现名:玫烟色棒束孢(Isaria fumosorosea)),尤其是菌株IFPC 200613,或菌株Apopka 97(登录号ATCC 20874);淡紫拟青霉(Paecilomyces lilacinus),尤其是淡紫拟青霉菌株251(AGAL89/030550);黄色蠕形霉(Talaromyces flavus),尤其是菌株V117b;深绿木霉(Trichoderma atroviride),尤其是菌株SC1(登录号CBS122089);哈茨木霉(Trichodermaharzianum),尤其是哈茨木霉T39(登录号CNCM I-952)。
用作或可用作生物农药的病毒的实例为:
棉褐带卷蛾(Adoxophyes orana)(夏季水果卷叶蛾(summer fruit tortrix))颗粒型病毒(GV)、苹果蠹蛾(Cydia pomonella(codling moth))颗粒型病毒(GV)、棉铃虫(Helicoverpa armigera(cotton bollworm))核型多角体病毒(NPV)、甜菜夜蛾(Spodoptera exigua(beet armyworm))mNPV、草地贪夜蛾(Spodoptera frugiperda(秋夜蛾(fall armyworm)))mNPV、海灰翅夜蛾(Spodoptera littoralis(非洲棉树叶虫(Africancotton leafworm)))NPV。
还包括作为“接种剂”添加到植物或植物部位或植物器官中的细菌和真菌,这些细菌和真菌通过其特定性质促进植物生长和植物健康。实例包括:
土壤杆菌属(Agrobacterium spp.)、茎瘤固氮根瘤菌(Azorhizobiumcaulinodans)、固氮螺菌属(Azospirillum spp.)、固氮菌属(Azotobacter spp.)、短根瘤菌属(Bradyrhizobium spp.)、伯霍尔德杆菌属(Burkholderia spp.),尤其是洋葱伯霍尔德杆菌(Burkholderia cepacia)(以前称为洋葱假单胞菌(Pseudomonas cepacia))、巨孢囊霉属(Gigaspora spp.)、或Gigaspora monosporum、球囊霉属(Glomus spp.)、蜡蘑属(Laccaria spp.)、布赫纳乳杆菌(Lactobacillus buchneri)、类球囊霉属(Paraglomusspp.)、豆包菌(Pisolithus tinctorus)、假单胞菌属(Pseudomonas spp.)、根瘤菌属(Rhizobium spp.)尤其是三叶草根瘤菌(Rhizobium trifolii)、须腹菌属(Rhizopogonspp.)、硬皮锈菌属(Scleroderma spp.)、乳牛肝菌属(Suillus spp.)、链霉菌属(Streptomyces spp.)。
用作或可用作生物农药的植物提取物和由微生物形成的产物(包括蛋白和次级代谢物)的实例为:
大蒜(Allium sativum)、苦艾(Artemisia absinthium)、印楝素(azadirachtin)、Biokeeper WP、Cassia nigricans、苦皮藤(Celastrus angulatus)、Chenopodiumanthelminticum、壳多糖(chitin)、Armour-Zen、鳞毛蕨(Dryopteris filix-mas)、问荆(Equisetum arvense)、Fortune Aza、Fungastop、Heads Up(奎奴亚藜(Chenopodiumquinoa)皂苷提取物)、除虫菊/除虫菊酯类、苏里南苦木(Quassia amara)、栎树属(Quercus)、皂树属(Quillaja)、Regalia、“Requiem TM杀昆虫剂”、鱼藤酮(rotenone)、鱼尼丁/兰尼碱、聚合草(Symphytum officinale)、艾菊(Tanacetum vulgare)、麝香草酚(thymol)、Triact 70、TriCon、旱金莲(Tropaeulum majus)、大荨麻(Urtica dioica)、Veratrin、槲寄生(Viscum album)、十字花科(Brassicaceae)提取物,尤其是油菜籽粉末或芥末粉末。
作为混合组分的安全剂
式(I)的化合物可与安全剂组合,所述安全剂为例如解草酮(benoxacor)、喹氧乙酸(cloquintocet(-mexyl))、解草胺腈(cyometrinil)、环丙磺酰胺(cyprosulfamide)、二氯丙烯胺(dichlormid)、解草唑(fenchlorazole(-ethyl))、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草噁唑(furilazole)、双苯噁唑酸(乙酯)(isoxadifen(-ethyl))、吡唑解草酯(mefenpyr(-diethyl))、萘二甲酸酐(naphthalicanhydride)、解草腈(oxabetrinil)、2-甲氧基-N-{4-[(甲基氨基甲酰基)氨基]苯基}磺酰基)苯甲酰胺(CAS 129531-12-0)、4-(二氯乙酰基)-1-氧杂-4-氮杂螺[4.5]癸烷(CAS71526-07-3)、2,2,5-三甲基-3-(二氯乙酰基)-1,3-噁唑烷(CAS52836-31-4)。
植物和植物部位
所有的植物和植物部位均可根据本发明进行处理。在本文中植物应理解为意指所有植物和植物种群,例如期望和不期望的野生植物或作物植物(包括天然存在的作物植物),例如谷物(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、糖用甜菜、甘蔗、番茄、甜椒、黄瓜、甜瓜、胡萝卜、西瓜、洋葱、莴苣、菠菜、韭、豆类、甘蓝(如卷心菜)和其他蔬菜品种,棉花、烟草、油菜,以及水果植物(水果为苹果、梨、柑橘类水果和葡萄)。作物植物可以为可通过常规的育种和优化方法或者通过生物技术方法和基因工程方法或这些方法的组合而获得的植物,包括转基因植物以及可受或不受植物育种者的权利(plant breeders’right)保护的植物栽培种。植物应理解为意指所有发育阶段,例如种子、幼苗和早期(未成熟)植物直至并包括成熟植物。植物部位应理解为意指植物的地上和地下的所有部位和器官,如芽、叶、花和根,给出的实例为叶、针叶、茎、枝干、花、子实体、果实和种子,以及根、块茎和根茎。植物部位还包括采收植物或采收植物部位以及无性和有性繁殖的材料,例如插条、块茎、根茎、分檗(slip)和种子。
本发明使用式(I)的化合物对植物和植物部位进行的处理通过常规处理方法直接进行或使所述化合物作用于其环境、生境或储存空间来进行,例如通过浸渍、喷雾、蒸发、雾化、撒播、涂抹、注射进行,以及在繁殖材料、尤其是种子的情况下,还通过施用一层或多层包衣来进行。
如上所述,可根据本发明处理所有植物及其部位。在优选实施方案中,处理野生植物物种和植物栽培种,或通过常规生物育种方法如杂交或原生质体融合而获得的那些,及其部位。在另一优选实施方案中,处理通过基因工程方法—如果合适,与常规方法组合—而获得的转基因植物和植物栽培种(遗传修饰生物体)及其部位。术语“部位”或“植物的部位”或“植物部位”已在上文中作出解释。根据本发明特别优选处理各市售可得的常规植物栽培种的植物或正在使用的那些植物。植物栽培种应理解为意指具有新特性(“性状”)并且已通过常规育种、通过诱变或通过重组DNA技术获得的植物。它们可以是栽培种、变种、生物型或基因型。
转基因植物、种子处理和整合株系(integration event)
根据本发明处理的优选的转基因植物或植物栽培种(通过基因工程获得的那些植物)包括通过基因修饰接受了赋予这些植物特别有利的有用特性(“性状”)的基因材料的所有植物。这些特性的实例为:更好的植物生长、对高温或低温的增强的耐受性、对干旱或对水或土壤盐度水平的增强的耐受性、提高的开花性能、更容易采收、加速成熟、更高的采收产量、采收产品的更高的品质和/或更高的营养价值、采收产品的更好的储存能力和/或可加工性。这些特性的其他和特别强调的实例为:增强植物对动物害虫和微生物害虫的抗性,例如昆虫、蛛形纲动物、线虫、螨、蛞蝓以及蜗牛,这归因于例如在植物中形成的毒素、特别是通过苏云金芽孢杆菌的基因材料(例如通过基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF及其组合)在植物中形成的那些毒素,以及增强的植物对植物病原性真菌、细菌和/或病毒的抗性,其例如由内吸性获得的抗性(SAR)、系统素(systemin)、植物抗毒素、激发子和抗性基因及相应表达的蛋白质和毒素引起,以及增强的植物对某些除草活性化合物的耐受性,例如咪唑啉酮类、磺酰脲类、草甘膦或膦丝菌素(phosphinothricin)(例如“PAT”基因)。赋予了所需特性(“性状”)的基因还可互相结合地存在于转基因植物中。所提及的转基因植物的实例包括重要的作物植物,例如谷物(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、糖用甜菜、甘蔗、番茄、豌豆和其他蔬菜类型,棉花、烟草、油菜,以及水果植物(水果为苹果、梨、柑橘类水果和葡萄),尤其强调的是玉米、大豆、小麦、稻、马铃薯、棉花、甘蔗、烟草和油菜。特别强调的特性(“性状”)是增强的植物对昆虫、蛛形纲动物、线虫和蛞蝓以及蜗牛的抗性。
作物保护——处理的类型
使用常规处理方法利用式(I)的化合物对植物和植物部位进行直接处理或通过作用于其环境、生境或储存空间来进行处理,所述常规处理方法为例如浸渍、喷雾、雾化、灌溉、蒸发、撒粉、成雾、撒播、发泡、涂抹、撒布、注射、浇水(浇灌)、滴灌,以及在繁殖材料、特别是种子的情况下,还通过干种子处理、湿种子处理、浆体处理、结壳、通过用一层或多层包衣包覆等进行处理。还可以通过超低容量法施用式(I)的化合物或者将施用形式或式(I)的化合物本身注射到土壤中。
优选的对植物的直接处理为叶面施用,即将式(I)的化合物施用到叶面上,在该情况下处理频率和施用率应根据所述害虫的侵染水平来调节。
在内吸性活性化合物的情况下,式(I)的化合物还经由根系统进入植物。于是通过将式(I)的化合物作用于植物的生境来处理该植物。这可以通过下述方式完成:例如,浇灌;或者通过混入土壤或营养液中,这意味着植物的生长场所(例如土壤或水培体系)被液体形式的式(I)的化合物浸渍;或通过土壤施用,这意味着将本发明的式(I)的化合物以固体形式(例如以颗粒剂的形式)引入到植物的生长场所。在水稻作物的情况下,这还可以通过将式(I)的化合物以固体施用形式(例如作为颗粒剂)计量加入水稻田来完成。
种子处理
人们早已知道通过处理植物种子来防治动物害虫并且这是不断改进的主题。然而,种子处理涉及一系列不能总是以令人满意的方式得以解决的问题。因此,需要开发保护种子和发芽植物的方法,该方法不需要或至少显著地减少了在储存过程中、在播种后或在植物出苗后农药的额外施用。此外还需要优化所使用的活性化合物的量,以便为种子和发芽植物提供最佳的保护以免受动物害虫的侵害,而所使用的活性化合物则不会损害植物本身。特别地,处理种子的方法还应考虑到害虫抗性或害虫耐受性转基因植物的固有的杀昆虫或杀线虫特性,以便用最少量的农药来实现对种子以及发芽植物的最佳保护。
因此,特别地,本发明还涉及一种通过用式(I)的化合物之一处理种子来保护种子和发芽植物免受害虫侵害的方法。本发明的保护种子和发芽植物免受害虫侵害的方法还包括在一个操作中同时或依序使用式(I)的化合物和混合组分处理种子的方法。其还包括在不同的时间使用式(I)的化合物和混合组分处理种子的方法。
本发明还涉及式(I)的化合物用于处理种子以保护种子和所得植物免受动物害虫侵害的用途。
本发明还涉及使用本发明的式(I)的化合物处理以保护其免受动物害虫侵害的种子。本发明还涉及同时使用式(I)的化合物和混合组分处理的种子。本发明还涉及在不同时间使用式(I)的化合物和混合组分处理的种子。在不同时间使用式(I)的化合物和混合组分处理的种子的情况下,各物质可以在不同的层中存在于种子上。在这种情况下,包含式(I)的化合物和混合组分的层可以任选地被中间层分隔。本发明还涉及其中施用了式(I)的化合物和混合组分作为包衣的一部分或作为除包衣外的另一层或另几层的种子。
本发明还涉及在用式(I)的化合物处理后,进行薄膜包衣过程以防止种子遭受灰尘磨损的种子。
当式(I)的化合物内吸性地起作用时,产生的优点之一在于:种子的处理,不仅保护种子本身还保护由其得到的植物在出苗后免受动物害虫的侵害。以这种方式,可无需在播种时或在其之后不久对作物进行即时处理。
另一个优势在于,用式(I)的化合物处理种子可促进已处理过的种子的发芽和出苗。
同样认为有利的是,式(I)的化合物还可特别地用于转基因种子。
式(I)的化合物还可与信号技术组合物组合使用,从而导致共生体(例如根瘤菌、菌根和/或内生细菌或真菌)更好的定殖(colonization),和/或优化的固氮作用。
式(I)的化合物适于保护在农业、温室、林业或园艺中使用的任何植物品种的种子。更具体而言,其为以下植物的种子:谷物(例如小麦、大麦、黑麦、粟和燕麦)、玉米、棉花、大豆、稻、马铃薯、向日葵、咖啡、烟草、加拿大油菜、油菜、甜菜(例如糖用甜菜和饲用甜菜)、花生、蔬菜(例如番茄、黄瓜、菜豆、十字花科蔬菜、洋葱和莴苣)、水果植物、草坪植物和观赏性植物。特别重要的是处理谷物(小麦、大麦、黑麦、燕麦)、玉米、大豆、棉花、加拿大油菜、油菜、蔬菜和稻的种子。
如上所述,用式(I)的化合物处理转基因种子也是特别重要的。这包括通常包含至少一种异源基因的植物的种子,所述异源基因控制特别是具有杀昆虫和/或杀线虫特性的多肽的表达。转基因种子中的异源基因可源自微生物如芽孢杆菌属(Bacillus)、根瘤菌属(Rhizobium)、假单孢菌属(Pseudomonas)、沙雷氏菌属(Serratia)、木霉属(Trichoderma)、棍状杆菌属(Clavibacter)、球囊霉属(Glomus)或胶霉属(Gliocladium)。本发明特别适用于处理包含至少一种源自芽孢杆菌属的异源基因的转基因种子。所述异源基因更优选衍生自苏云金芽孢杆菌(Bacillus thuringiensis)。
在本发明的上下文中,将式(I)的化合物施用于种子。优选在这样的状态下处理种子:其足够稳定以使得在处理过程中不发生损害。通常,可在采收和播种之间的任意时间处理种子。通常使用已与植物分离并且已除去穗轴、壳、茎、荚(coat)、毛或果肉的种子。例如,可使用已采收、清洁并干燥至允许贮存的水分含量的种子。或者,还可使用在干燥之后例如用水处理然后再干燥(例如引发(priming))的种子。在稻种子的情况下,还可以使用例如已浸泡在水中直至其达到稻胚芽的某一阶段(“胚乳(pigeon breast)阶段”)的种子,这导致刺激了发芽和更均匀的出芽。
在处理种子时,通常必须确保选择施用于种子的式(I)的化合物的量和/或其他添加剂的量,使得不对种子的发芽产生不利的影响,或不损害所得的植物。特别是对于在某些施用率下可能会表现出植物毒性效应的活性化合物,必须保证这点。
通常,将式(I)的化合物以合适的制剂形式施用于种子。用于种子处理的合适的制剂和方法是本领域技术人员已知的。
可将式(I)的化合物转化为常规的拌种制剂,例如溶液剂、乳剂、悬浮剂、粉剂、泡沫剂、浆剂(slurry)或其他种子包衣组合物,以及ULV制剂。
这些制剂用已知方式通过使式(I)的化合物与常规添加剂(例如常规的增量剂以及溶剂或稀释剂、染料、润湿剂、分散剂、乳化剂、消泡剂、防腐剂、二次增稠剂、胶粘剂、赤霉素以及水)进行混合而制备。
可存在于可根据本发明使用的拌种制剂中的染料为常用于此目的的所有染料。可使用微溶于水的颜料或溶于水的染料。实例包括已知的名称为罗丹明B(Rhodamine B)、C.I.颜料红112和C.I.溶剂红1的染料。
可存在于可根据本发明使用的拌种制剂中的有用的润湿组合物为促进润湿并通常用于配制农用化学活性化合物的所有物质。优选使用萘磺酸烷基酯,如萘磺酸二异丙酯或萘磺酸二异丁酯。
可存在于可根据本发明使用的拌种制剂中的合适的分散剂和/或乳化剂为常用于配制农用化学活性化合物的所有非离子、阴离子和阳离子分散剂。可优选使用非离子或阴离子分散剂,或者非离子或阴离子分散剂的混合物。合适的非离子分散剂特别地包括环氧乙烷/环氧丙烷嵌段聚合物、烷基酚聚乙二醇醚和三苯乙烯基苯酚聚乙二醇醚,以及其磷酸化或硫酸化衍生物。合适的阴离子分散剂特别为木质素磺酸盐、聚丙烯酸盐和芳基磺酸盐-甲醛缩合物。
可存在于可根据本发明使用的拌种制剂中的消泡剂为常用于配制农用化学活性化合物的所有抑制泡沫的物质。可优选使用硅酮消泡剂和硬脂酸镁。
可存在于可根据本发明使用的拌种制剂中的防腐剂为可在农用化学组合物中用于此目的的所有物质。实例包括二氯酚和苄醇半缩甲醛。
可存在于可根据本发明使用的拌种制剂中的有用的二次增稠剂为可在农用化学组合物中用于此目的的所有物质。优选的实例包括纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土以及细分散二氧化硅。
可存在于可根据本发明使用的拌种制剂中的有用的粘着剂为可用于拌种产品的所有常规的粘合剂。优选的实例包括聚乙烯基吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和甲基纤维素。
可存在于可根据本发明使用的拌种制剂中的有用的赤霉素优选为赤霉素A1、A3(=赤霉酸)、A4和A7;特别优选使用赤霉酸。所述赤霉素是已知的(参见R.Wegler“Chemieder Pflanzenschutz-und第2卷,SpringerVerlag,1970,第401-412页)。
可根据本发明使用的拌种制剂可以直接地或在预先用水稀释后,用于处理各种不同类型的种子。例如,浓缩剂或可通过用水稀释而由其获得的制剂可用于拌种以下植物的种子:谷物(例如小麦、大麦、黑麦、燕麦和黑小麦),以及玉米、稻、油菜、豌豆、豆类、棉花、向日葵、大豆和甜菜,或各种不同的蔬菜。可根据本发明使用的拌种制剂或其稀释施用形式还可用于拌种转基因植物的种子。
对于用可根据本发明使用的拌种制剂或通过加入水而由其制得的施用形式来处理种子,所有常用于拌种的混合装置都是有用的。具体而言,拌种过程为将种子置于间歇操作或连续操作的混合器中;加入特定所需量的拌种制剂(以其本身或在预先用水稀释后);以及进行混合直到制剂均匀地分布在种子上。如果合适,之后进行干燥操作。
可根据本发明使用的拌种制剂的施用率可在较宽的范围内变化。这由制剂中式(I)的化合物的具体含量以及种子决定。式(I)的化合物的施用率通常为0.001至50g/kg种子,优选0.01至15g/kg种子。
动物健康
在动物健康领域,即兽医学领域,式(I)的化合物对于动物寄生虫、特别是外寄生虫或内寄生虫是有活性的。术语“内寄生虫”特别包括蠕虫和原生动物,如球虫目(coccidia)。外寄生虫通常且优选为节肢动物,尤其是昆虫或螨类。
在兽医学领域中,具有有利的恒温动物毒性的式(I)的化合物适用于防治在家畜、繁育动物、动物园动物、实验室动物、实验动物和家养动物中在动物繁育和动物饲养中出现的寄生虫。其在对抗寄生虫的所有或特定发育阶段具有活性。
农业家畜包括例如哺乳动物,如绵羊、山羊、马、驴、骆驼、水牛、兔、驯鹿、扁角鹿,尤其是牛和猪;或家禽,如火鸡、鸭、鹅,尤其是鸡;或鱼或甲壳动物,如在水产养殖中;或可视情况,昆虫如蜜蜂。
家养动物包括例如哺乳动物,如仓鼠、豚鼠、大鼠、小鼠、毛丝鼠、雪貂,特别是狗、猫、笼鸟;爬行动物、两栖动物或观赏鱼。
在具体实施方案中,将式(I)的化合物施用于哺乳动物。
在另一具体实施方案中,将式(I)的化合物施用于禽类,即笼鸟或特别是家禽。
使用式(I)的化合物来防治动物寄生虫,旨在减少或预防疾病、死亡病例和性能下降(在肉、奶、毛、皮、蛋、蜜等情况下),从而使得动物饲养更经济且更简单,并可实现更好的动物健康。
在本文的上下文中,关于动物健康领域,术语“防治”(control或controlling)意指式(I)的化合物有效地将被寄生虫感染的动物中的特定寄生虫的发生率降低至无害水平。更具体而言,在本文的上下文中,“防治”意指式(I)的化合物杀死各种寄生虫、抑制其生长或抑制其增殖。
节肢动物包括但不限于:
虱目(Anoplurida),例如血虱属(Haematopinus spp.)、毛虱属(Linognathusspp.)、虱属(Pediculus spp.)、Phtirus属和管虱属(Solenopotes spp.);
食毛目(Mallophagida)和钝角亚目(Amblycerina)和丝角亚目(Ischnocerina),例如牛羽虱属(Bovicola spp.)、畜虱属(Damalina spp.)、猫虱属(Felicola spp.)、Lepikentron属、禽虱属(Menopon spp.)、嚼虱属(Trichodectes spp.)、毛羽虱属(Trimenopon spp.)、巨羽虱属(Trinoton spp.)、Werneckiella属;
双翅目(Diptera)和长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、黄虻属(Atylotus spp.)、蜂虱蝇属(Braula spp.)、丽蝇属(Calliphora spp.)、金蝇属(Chrysomyia spp.)、斑虻属(Chrysopsspp.)、库蚊属(Culex spp.)、库蠓属(Culicoides spp.)、真蚋属(Eusimulium spp.)、厕蝇属(Fannia spp.)、胃蝇属(Gasterophilus spp.)、舌蝇属(Glossina spp.)、角蝇属(Haematobia spp.)、麻虻属(Haematopota spp.)、虱蝇属(Hippobosca spp.)、瘤虻属(Hybomitra spp.)、齿股蝇属(Hydrotaea spp.)、皮蝇属(Hypoderma spp.)、羊虱蝇属(Lipoptena spp.)、绿蝇属(Lucilia spp.)、罗蛉属(Lutzomyia spp.)、蜱蝇属(Melophagus spp.)、莫蝇属(Morellia spp.)、家蝇属(Musca spp.)、短蚋属(Odagmiaspp.)、狂蝇属(Oestrus spp.)、Philipomyia属、白蛉属(Phlebotomus spp.)、鼻狂蝇属(Rhinoestrus spp.)、麻蝇属(Sarcophaga spp.)、蚋属(Simulium spp.)、螫蝇属(Stomoxys spp.)、虻属(Tabanus spp.)、大蚊属(Tipula spp.)、维蚋属(Wilhelmiaspp.)、污蝇属(Wohlfahrtia spp.);
蚤目(Siphonapterida),例如角叶蚤属(Ceratophyllus spp.)、栉头蚤属(Ctenocephalides spp.)、蚤属(Pulex spp.)、潜蚤属(Tunga spp.)、客蚤属(Xenopsyllaspp.);
异翅目(Heteropterida),例如臭虫属(Cimex spp.)、锥蝽属(Panstrongylusspp.)、红猎蝽属(Rhodnius spp.)、锥猎蝽属(Triatoma spp.);以及来自蜚蠊目(Blattarida)的公害(nuisance)和卫生害虫。
此外,在节肢动物的情况下,应提及例如但不限于以下蜱螨亚纲(Acari):
蜱螨亚纲(Acari)(蜱螨目(Acarina))和后气门目(Metastigmata),例如软蜱科(Argasidae)如锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodorus spp.)、耳蜱属(Otobiusspp.),硬蜱科(Ixodidae)如花蜱属(Amblyomma spp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemophysalis spp.)、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、扇头蜱属(Rhipicephalus(牛蜱属(Boophilus))spp.)、扇头蜱属(Rhipicephalus spp.)(多宿主蜱的原始属);中气门目(Mesostigmata)如皮刺螨属(Dermanyssus spp.)、禽刺螨属(Ornithonyssus spp.)、肺刺螨属(Pneumonyssus spp.)、刺利螨属(Raillietia spp.)、胸孔螨属(Sternostoma spp.)、厉螨属(Tropilaelaps spp.)、瓦螨属(Varroa spp.);辐螨目(Actinedida)(前气门目(Prostigmata)),例如蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、蠕形螨属(Demodex spp.)、Listrophorus属、肉螨属(Myobiaspp.)、新恙螨属(Neotrombicula spp.)、禽螯螨属(Ornithocheyletia spp.)、疮螨属(Psorergates spp.)、恙螨属(Trombicula spp.);和粉螨目(Acaridida)(无气门目(Astigmata)),例如粉螨属(Acarus spp.)、嗜木螨属(Caloglyphus spp.)、皮螨属(Chorioptes spp.)、气囊螨属(Cytodites spp.)、颈下螨属(Hypodectes spp.)、鸟疥螨属(Knemidocoptes spp.)、鸡雏螨属(Laminosioptes spp.)、耳螨属(Notoedres spp.)、耳疥螨属(Otodectes spp.)、痒螨属(Psoroptes spp.)、翅螨属(Pterolichus spp.)、疥螨属(Sarcoptes spp.)、Trixacarus属、食酪螨属(Tyrophagus spp.)。
寄生性原生动物的实例包括但不限于:
鞭毛纲(Mastigophora)(鞭毛虫纲(Flagellata)),例如:
后滴门(Metamonada):双滴虫目(Diplomonadida),例如贾第虫属(Giardiaspp.)、螺旋核虫属(Spironucleus spp.)。
Parabasala:毛滴虫目(Trichomonadida),例如组织滴虫属(Histomonas spp.)、五鞭毛滴虫属(Pentatrichomonas spp.)、四毛滴虫属(Tetratrichomonas spp.)、毛滴虫属(Trichomonas spp.)、三毛滴虫属(Tritrichomonas spp.)。
眼虫门(Euglenozoa):锥体虫目(Trypanosomatida),例如利什曼原虫属(Leishmania spp.)、锥体虫属(Trypanosoma spp.)。
肉鞭虫亚门(Sarcomastigophora)(肉足亚门(Rhizopoda)),例如内阿米巴科(Entamoebidae),例如内阿米巴属(Entamoeba spp.)、Centramoebidae,例如棘变形虫属(Acanthamoeba sp.)、Euamoebidae,例如哈氏虫属(Harmanella sp.)。
囊泡虫类(Alveolata),如顶复亚门(Apicomplexa)(孢子重亚门(Sporozoa)):如隐孢子虫属(Cryptosporidium spp.);艾美耳球虫目(Eimeriida),例如贝诺孢子虫属(Besnoitia spp.)、囊等孢虫属(Cystoisospora spp.)、艾美球虫属(Eimeria spp.)、哈蒙德虫属(Hammondia spp.)、等孢子球虫属(Isospora spp.)、新孢子虫属(Neospora spp.)、肉孢子虫属(Sarcocystis spp.)、弓形虫属(Toxoplasma spp.);Adeleida目,例如肝簇虫属(Hepatozoon spp.)、克洛虫属(Klossiella spp.);血孢子虫目(Haemosporida),例如住白虫属(Leucocytozoon spp.)、疟原虫属(Plasmodium spp.);梨形虫目(Piroplasmida),例如巴贝虫属(Babesia spp.)、纤毛虫属(Ciliophora spp.)、Echinozoon属、泰勒虫属(Theileria spp.);Vesibuliferida目,例如肠袋虫属(Balantidium spp.)、布克斯顿纤毛虫属(Buxtonella spp.)。
微孢子门(Microspora),例如脑胞内原虫属(Encephalitozoon spp.)、肠孢虫属(Enterocytozoon spp.)、球形虫属(Globidium spp.)、微粒子虫属(Nosema spp.)、以及例如粘原虫属(Myxozoa spp.)。
对人或动物致病的蠕虫包括例如棘头虫纲(Acanthocephala)、Nematoden、舌形动物门(Pentastoma)和扁形动物门(Platyhelminthes)(如,单殖亚纲(Monogenea)、绦虫(Cestode)和吸虫类(trematodes))。
示例性的蠕虫包括但不限于:
单殖亚纲:例如:指环虫属(Dactylogyrus spp.)、三代虫属(Gyrodactylusspp.)、Microbothrium属、多盘吸虫属(Polystoma spp.)、Troglecephalus属;
绦虫:假叶目(Pseudophyllidea),例如:吸叶绦虫属(Bothridium spp.)、裂头绦虫属(Diphyllobothrium spp.)、复殖孔绦虫属(Diplogonoporus spp.)、Ichthyobothrium属、舌状绦虫属(Ligula spp.)、Schistocephalus属、迭宫绦虫属(Spirometra spp.);
圆叶目(cyclophyllidea),例如:Andyra属、裸头绦虫属(Anoplocephala spp.)、无卵黄腺绦虫属(Avitellina spp.)、伯特绦虫属(Bertiella spp.)、鸣绦虫属(Cittotaenia spp.)、代凡绦虫属(Davainea spp.)、双睾绦虫属(Diorchis spp.)、复孔绦虫属(Diplopylidium spp.)、犬复孔绦虫属(Dipylidium spp.)、棘球绦虫属(Echinococcus spp.)、棘叶绦虫属(Echinocotyle spp.)、棘鳞绦虫属(Echinolepisspp.)、泡尾绦虫属(Hydatigera spp.)、膜壳绦虫属(Hymenolepis spp.)、约优克斯绦虫属(Joyeuxiella spp.)、中殖孔绦虫属(Mesocestoides spp.)、蒙尼茨绦虫属(Monieziaspp.)、副裸头绦虫属(Paranoplocehala spp.)、瑞利绦虫属(Raillietina spp.)、西里西亚绦虫属(Stilesia spp.)、带绦虫属(Taenia spp.)、曲子宫绦虫属(Thysaniezia spp.)、Thysanosomsa属;
吸虫:选自复殖纲(Digenea),例如:澳毕吸虫属(Austrobilharziaspp.)、短咽吸虫属(Brachylaima spp.)、杯殖吸虫属(Calicophoron spp.)、下弯吸虫属(Catatropisspp.)、支睾吸虫属(Clonorchis spp.)、肛瘤吸虫属(Collyriclum spp.)、殖盘吸虫属(Cotylophoron spp.)、环腔吸虫属(Cyclocoelum spp.)、双腔吸虫属(Dicrocoeliumspp.)、双穴吸虫属(Diplostomum spp.)、棘隙吸虫属(Echinochasmus spp.)、棘缘吸虫属(Echinoparyphium spp.)、棘口吸虫属(Echinostoma spp.)、阔盘吸虫属(Eurytemaspp.)、片形吸虫属(Fasciola spp.)、片形吸虫属(Fascioloides spp.)、姜片吸虫属(Fasciolopsis spp.)、菲策吸虫(Fischoederius spp.)、腹袋吸虫属(Gastrothylacusspp.)、巨毕吸虫属(Gigantobilharzia spp.)、巨盘吸虫属(Gigantoctyle spp.)、异形吸虫属(Heterophyes spp.)、低颈吸虫属(Hypoderaeum spp.)、彩蚴吸虫属(Leucochloridium spp.)、后殖吸虫属(Metagonimus spp.)、次睾吸虫属(Metorchisspp.)、侏形吸虫属(Nanophyetus spp.)、背孔吸虫属(Notocotylus spp.)、后睾吸虫属(Opisthorchis spp.)、鸟毕吸虫属(Ornithobilharzia spp.)、并殖吸虫属(Paragonimusspp.)、同端盘吸虫属(Paramphistomum spp.)、斜睾吸虫属(Plagiorchis spp.)、茎双穴吸虫属(Posthodiplostomum spp.)、前殖吸虫属(Prosthogonimus spp.)、血吸虫属(Schistosoma spp.)、毛毕吸虫属(Trichobilharzia spp.)、鲑吸虫属(Troglotremaspp.)、盲腔吸虫属(Typhlocoelum spp.);
线虫:毛线目(Trichinellida),例如:毛细线虫属(Capillaria spp.)、旋毛虫属(Trichinella spp.)、Trichomosoides属、鞭虫属(Trichuris spp.);
垫刃目(Tylenchida),例如:细丝鲶属(Micronema spp.)、Parastrangyloides属、类圆线虫属(Strongyloides spp.);
杆形目(Rhabditida),例如:猫圆线虫属(Aelurostrongylus spp.)、裂口线虫属(Amidostomum spp.)、钩虫线虫属(Ancylostoma spp.)、血管圆线虫属(Angiostrongylusspp.)、Bronchonema属、仰口线虫属(Bunostomum spp.)、夏伯特线虫属(Chabertia spp.)、古柏线虫属(Cooperia spp.)、Cooperioides属、环体线虫属(Crenosoma spp.)、杯口属(Cyathostomum spp.)、Cyclococercus属、Cyclodontostomum属、杯杯属(Cylicocyclusspp.)、杯冠属(Cylicostephanus spp.)、柱咽属(Cylindropharynx spp.)、囊尾线虫属(Cystocaulus spp.)、网尾线虫属(Dictyocaulus spp.)、鹿圆线虫属(Elaphostrongylusspp.)、类丝虫属(Filaroides spp.)、球首属(Globocephalus spp.)、细纹线虫属(Graphidium spp.)、辐首线虫属(Gyalocephalus spp.)、血矛线虫属(Haemonchus spp.)、螺旋线虫属(Heligmosomoides spp.)、猪圆线虫属(Hyostrongylus spp.)、马歇尔线虫属(Marshallagia spp.)、后圆线虫属(Metastrongylus spp.)、缪勒线虫属(Muelleriusspp.)、板口线虫属(Necator spp.)、细颈线虫属(Nematodirus spp.)、新圆线虫属(Neostrongylus spp.)、日本圆线虫属(Nippostrongylus spp.)、尖柱线虫属(Obeliscoides spp.)、食道齿属(Oesophagodontus spp.)、食道口线虫属(Oesophagostomum spp.)、沃鲁线虫属(Ollulanus spp.)、鸟圆线虫属(Ornithostrongylus spp.)、奥斯勒线虫属(Oslerus spp.)、奥斯特线虫属(Ostertagiaspp.)、副库柏属(Paracooperia spp.)、Paracrenosoma属、副类丝虫属(Parafilaroidesspp.)、拟马鹿圆线虫属(Parelaphostrongylus spp.)、肺尾属(Pneumocaulus spp.)、肺圆线虫属(Pneumostrongylus spp.)、杯口线虫属(Poteriostomum spp.)、原圆线虫属(Protostrongylus spp.)、Spicocaulus属、冠尾线属(Stephanurus spp.)、圆线虫属(Strongylus spp.)、比翼属(Syngamus spp.)、背带线虫属(Teladorsagia spp.)、毛线属(Trichonema spp.)、毛圆线虫属(Trichostrongylus spp.)、三齿属(Triodontophorusspp.)、隐圆线虫属(Troglostrongylus spp.)、弯口属(Uncinaria spp.);
旋尾目(Spirurida),例如:棘唇线虫属(Acanthocheilonema spp.)、异尖线虫属(Anisakis spp.)、禽蛔虫属(Ascaridia spp.)、蛔虫属(Ascaris spp.)、斜环咽线虫属(Ascarops spp.)、无刺线虫属(Aspiculuris spp.)、贝利蛔线虫属(Baylisascarisspp.)、布鲁线虫属(Brugia spp.)、Cercopithifilaria属、Crassicauda属、棘唇线虫属(Dipetalonema spp.)、恶丝虫属(Dirofilaria spp.)、龙线虫属(Dracunculus spp.)、德拉西线虫属(Draschia spp.)、蛲虫属(Enterobius spp.)、丝虫属(Filaria spp.)、颚口线虫属(Gnathostomaspp.)、筒线虫属(Gongylonema spp.)、丽线虫属(Habronema spp.)、异刺线虫属(Heterakis spp.);光丝虫属(Litomosoides spp.)、罗阿丝虫属(Loa spp.)、盘尾丝虫属(Onchocerca spp.)、尖尾线虫属(Oxyuris spp.)、副柔线属(Parabronemaspp.)、副丝虫属(Parafilaria spp.)、副蛔虫属(Parascaris spp.)、栓尾线虫属(Passalurus spp.)、泡翼线虫属(Physaloptera spp.)、普氏线虫属(Probstmayriaspp.)、Pseudofilaria属、腹腔丝虫属(Setaria spp.)、Skjrabinema属、旋毛线虫属(Spirocerca spp.)、冠丝虫属(Stephanofilaria spp.)、Strongyluris属、管状线虫属(Syphacia spp.)、吸吮线虫属(Thelazia spp.)、弓蛔线虫属(Toxascaris spp.)、弓蛔虫属(Toxocara spp.)、吴策线虫属(Wuchereria spp.);
棘头虫纲(Acanthocephala):寡棘吻目(Oligacanthorhynchida),例如:巨吻棘头虫属(Macracanthorhynchus spp.)、前睾棘头虫属(Prosthenorchis spp.);Moniliformida目,例如:念珠棘虫属(Moniliformis spp.);
多形目(Polymorphida),例如细颈棘头虫属(Filicollis spp.);棘吻目(Echinorhynchida),例如棘头花属(Acanthocephalus spp.)、棘吻虫属(Echinorhynchusspp.)、似细吻棘头虫属(Leptorhynchoides spp.);
舌形动物门(Pentastoma):蛇舌状虫目(Porocephalida),例如舌形虫属(Linguatula spp.)。
在兽医学领域和动物饲养中,通过本领域通常已知的方法(例如经肠内、胃肠外、真皮或经鼻途径)以合适的制剂形式施用式(I)的化合物。施用可以是预防性的、补救性(metaphylactic)的或治疗性的。
因此,本发明的一个实施方案涉及用作药物的式(I)的化合物。
另一个方面涉及用作抗内寄生虫剂的式(I)的化合物。
本发明的另一具体的方面涉及用作抗蠕虫剂(antihelminthic)、尤其是用作杀线虫剂、杀扁形动物剂、杀棘头虫剂或杀舌形动物剂的式(I)的化合物。
本发明的另一具体的方面涉及用作抗原生动物剂的式(I)的化合物。
另一方面涉及用作抗外寄生虫剂、尤其是杀节肢动物剂、非常特别是杀昆虫剂或杀螨剂的式(I)的化合物。
本发明的其他方面为兽药制剂,其包含有效量的至少一种式(I)的化合物和至少一种以下物质:药学上可接受的赋形剂(例如固体或液体稀释剂)、药学上可接受的助剂(例如表面活性剂),尤其是常规用于兽药制剂中的药学上可接受的赋形剂和/或常规用于兽药制剂中的药学上可接受的助剂。
本发明的相关方面是一种制备如本文所述的兽药制剂的方法,其包括以下步骤:将至少一种式(I)的化合物与药学上可接受的赋形剂和/或助剂、尤其是与常规用于兽药制剂中的药学上可接受的赋形剂和/或常规用于兽药制剂中的助剂进行混合。
本发明的另一具体方面是兽药制剂以及其制备方法,所述兽药制剂选自杀外寄生虫制剂和杀内寄生虫制剂,尤其选自上述方面的驱虫、抗原生动物和杀节肢动物制剂,非常特别选自杀线虫、杀扁形动物、杀棘头虫、杀舌形动物、杀昆虫和杀螨制剂。
另一方面涉及一种通过在有需求的动物、尤其是非人动物中使用有效量的式(I)的化合物来治疗寄生虫感染的方法,尤其是治疗由选自本文所提及的外寄生虫和内寄生虫的寄生虫所引起的感染的方法。
另一方面涉及一种通过在有需求的动物、尤其是非人动物中使用本文所定义的兽药制剂来治疗寄生虫感染的方法,尤其是治疗由选自本文所提及的外寄生虫和内寄生虫的寄生虫所引起的感染的方法。
另一方面涉及式(I)的化合物在治疗动物、尤其是非人动物的寄生虫感染、尤其是由选自本文所提及的外寄生虫和内寄生虫的寄生虫所引起的感染的用途。
在本发明的动物健康或兽医学的上下文中,术语“治疗”包括预防性的、补救性的或治疗性的治疗。
在具体实施方案中,以此方式,提供用于兽医学领域的至少一种式(I)的化合物与其他活性化合物、尤其是与杀内寄生虫剂和杀外寄生虫剂的混合物。
在动物健康领域,“混合物”不仅是指将两种(或更多种)不同的活性化合物以常规制剂进行配制并相应地一起使用,而且还涉及包含针对每种活性化合物分开的制剂的产品。因此,当使用两种以上的活性化合物时,可将所有活性化合物以常规制剂进行配制或者可将所有活性化合物以单独制剂进行配制;还可为混合的形式,其中一些活性化合物一起配制而一些活性化合物单独配制。单独的制剂可以单独或依次施用所述活性化合物。
本文中以其通用名称提及的活性化合物是已知的,并且记载于例如“农药手册(Pesticide Manual)”中(参见上文),或者可以在互联网(例如http://www.alanwood.net/ pesticides)上检索到。
作为混合组分的杀外寄生虫剂的示例性活性化合物,包括但无任何意图限于,上文详细列出的杀昆虫剂和杀螨剂。其他可使用的活性化合物根据上述基于现行的IRAC作用方式分类方案的分类列于下文中:(1)乙酰胆碱酯酶(AChE)抑制剂;(2)GABA-门控氯化物通道阻断剂;(3)钠通道调节剂;(4)烟碱乙酰胆碱受体(nAChR)竞争性调节剂;(5)烟碱乙酰胆碱受体(nAChR)变构调节剂;(6)谷氨酸门控氯化物通道(GluCl)变构调节剂;(7)保幼激素模仿物;(8)其他非特异性(多位点)抑制剂;(9)弦音器官调节剂;(10)螨生长抑制剂;(12)线粒体ATP合成酶抑制剂,如ATP干扰剂;(13)通过阻断质子梯度的氧化磷酸化的解偶联剂;(14)烟碱乙酰胆碱受体通道阻断剂;(15)几丁质生物合成抑制剂,0型;(16)几丁质生物合成抑制剂,1型;(17)蜕皮干扰剂(尤其是对于双翅目(Diptera));(18)蜕皮激素受体激动剂;(19)章鱼胺受体激动剂;(21)线粒体复合物I电子传递抑制剂;(25)线粒体复合物II电子传递抑制剂;(20)线粒体复合物III电子传递抑制剂;(22)电压依赖型钠通道阻断剂;(23)乙酰基CoA羧化酶抑制剂;(28)鱼尼丁受体调节剂;
具有未知或非特异性的作用机理的活性化合物,如fentrifanil、氧嘧酰胺(fenoxacrim)、cycloprene、乙酯杀螨醇(chlorobenzilate)、杀虫脒(chlordimeform)、氟苯灭(flubenzimin)、地昔尼尔(dicyclanil)、磺胺螨酯(amidoflumet)、灭螨猛(quinomethionat)、三苯噻螨吩(triarathene)、clothiazoben、杀螨氯硫(tetrasul)、油酸钾(potassiumoleate)、石油(petroleum)、恶虫酮(metoxadiazone)、gossyplur、氟螨嗪(flutenzine)、溴满酯(brompropylate)、氟铝酸钠(cryolite);
其他种类的化合物,例如畜虫威(butacarb)、敌蝇威(dimetilan)、除线威(cloethocarb)、磷虫威(phosphocarb)、嘧啶磷(乙基嘧啶磷)(pirimiphos(-ethyl))、对硫磷(乙基对硫磷)(parathion(-ethyl))、虫螨畏(methacrifos)、水杨酸异丙酯(isopropylo-salicylate)、三氯膦酸酯(trichlorfon)、硫丙磷(sulprofos)、丙虫磷(propaphos)、克线丹(sebufos)、哒硫磷(pyridathion)、发硫磷(prothoate)、除线磷(dichlofenthion)、甲基砜内吸磷(demeton-S-methyl sulfone)、氯唑磷(isazofos)、苯腈膦(cyanofenphos)、氯亚胺硫磷(dialifos)、三硫磷(carbophenothion)、特嘧硫磷(autathiofos)、aromfenvinfos(-methyl)、谷硫磷(乙基谷硫磷)(azinphos(-ethyl))、毒死蜱(乙基毒死蜱)(chlorpyrifos(-ethyl))、丁苯硫磷(fosmethilan)、碘硫磷(iodofenphos)、蔬果磷(dioxabenzofos)、安果(formothion)、地虫磷(fonofos)、吡氟硫磷(flupyrazofos)、丰索磷(fensulfothion)、乙嘧硫磷(etrimfos);
有机氯化物,例如毒杀芬(camphechlor)、林丹(lindane)、七氯(heptachlor);或苯基吡唑类,如acetoprole、pyrafluprole、pyriprole、vaniliprole、维吉霉素(sisapronil);或异噁唑啉类,如sarolaner、afoxolaner、lotilaner、fluralaner;
除虫菊酯(pyrethroids),如(顺式-、反式-)甲氧苄氟菊酯((cis-,trans-)metofluthrin)、丙氟菊酯(profluthrin)、三氟醚菊酯(flufenprox)、溴氟菊酯(flubrocythrinate)、气丙笨酸(fubfenprox)、芬氟司林(fenfluthrin)、protrifenbut、pyresmethrin、RU15525、环戊烯丙菊酯(terallethrin)、顺式-苄呋菊酯(cis-resmethrin)、heptafluthrin、bioethanomethrin、生物氯菊酯(biopermethrin)、吡氯氰菊酯(fenpyrithrin)、顺式-氯氰菊酯(cis-cypermethrin)、顺式-苄氯菊酯(cis-permethrin)、氰菊酯(clocythrin)、氯氟氰菊酯(cyhalothrin(lambda-))、二氯炔戊菊酯(chlovaporthrin),或卤代烃化合物(HCH),
新烟碱类,如硝乙脲噻唑(nithiazine);
dicloromezotiaz,三氟苯嘧啶(triflumezopyrim);
大环内酯类,如奈马克丁(nemadectin)、伊维菌素(ivermectin)、拉替待克丁(latidectin)、莫昔克丁(moxidectin)、司拉克丁(selamectin)、依立诺克丁(eprinomectin)、多拉克丁(doramectin)、埃玛菌素(emamectin benzoate);米尔贝肟(milbemycin oxime)
烯虫硫酯(triprene)、保幼醚(epofenonane)、苯虫醚(diofenolan);
生物制剂、激素或信息素,例如天然产物,如苏云金素(thuringiensin)、十二碳二烯醇(codlemone)或印楝(neem)成分
二硝基酚类,例如敌螨普(dinocap)、消螨通(dinobuton)、乐杀螨(binapacryl);
苯甲酰基脲类,例如氟佐隆(fluazuron)、氟幼脲(penfluron),
脒衍生物,例如chlormebuform、螨蜱胺(cymiazole)、得米地曲(demiditraz)
蜂巢杀螨剂(beehive varroa acaricide),例如有机酸,如甲酸、乙二酸。
作为混合组分的杀内寄生虫剂的示例性活性化合物包括但不限于驱虫活性化合物和抗原生动物(antiprotozoic)活性化合物。
驱虫活性化合物包括但不限于以下活性杀线虫、杀吸虫(trematicidally)和/或杀绦虫(cestocidally)活性化合物:
大环内酯类,例如:依立诺克丁(eprinomectin)、阿巴克丁(abamectin)、奈马克丁(nemadectin)、莫昔克丁(moxidectin)、多拉克丁(doramectin)、司拉克丁(selamectin)、雷皮菌素(lepimectin)、拉替待克丁(latidectin)、弥拜菌素(milbemectin)、伊维菌素(ivermectin)、依马菌素(emamectin)、米尔倍霉素(milbemycin);
苯并咪唑类和probenzimidazole,例如:奥苯达唑(oxibendazole)、甲苯咪唑(mebendazole)、三氯苯咪唑(triclabendazole)、托布津(thiophanate)、丁苯咪唑(parbendazole)、奥吩达唑(oxfendazole)、奈托比胺(netobimin)、芬苯达唑(fenbendazole)、非班太(febantel)、噻苯哒唑(thiabendazole)、环苯达唑(cyclobendazole)、坎苯达唑(cambendazole)、阿苯达唑亚砜(albendazole sulfoxide)、阿苯达唑(albendazole)、氟苯达唑(flubendazole);
缩肽类,优选环状缩肽,尤其是24元环状缩肽,例如:依吗德塞(emodepside)、PF1022A;
四氢嘧啶类,例如:莫仑太尔(morantel)、噻嘧啶(pyrantel)、奥克太尔(oxantel);
咪唑并噻唑类,例如:布他咪唑(butamisole)、左旋咪唑(levamisole)、四咪唑(tetramisole);
氨基苯基脒类,例如:阿米太尔(amidantel)、脱酰化阿米太尔(dAMD)、三苯双脒(tribendimidine);
氨基乙腈类,例如:莫奈太尔(monepantel);
paraherquamide类,例如:paraherquamide、德奎太尔(derquantel);
水杨酰苯胺类,例如:三溴沙仑(tribromsalan)、溴沙尼特(bromoxanide)、溴替尼特(brotianide)、氯碘沙尼(clioxanide)、氯生太尔(closantel)、氯硝柳胺(niclosamide)、羟氯扎胺(oxyclozanide)、雷复尼特(rafoxanide);
取代的酚类,例如:硝碘酚腈(nitroxynil)、硫氯酚(bithionol)、二碘硝酚(disophenol)、六氯芬(hexachlorophene)、联硝氯酚(niclofolan)、meniclopholan;
有机磷酸酯类,例如:三氯磷酸酯(trichlorfon)、naphthalofos、敌敌畏(dichlorvos/DDVP)、克芦磷酯(crufomate)、蝇毒磷(coumaphos)、哈洛克酮(haloxon);
哌嗪酮/喹啉,例如:吡喹酮(praziquantel)、依西太尔(epsiprantel);
哌嗪类,例如:哌嗪(piperazine)、羟嗪(hydroxyzine);
四环素类,例如:四环素(tetracycline)、金霉素(chlorotetracycline)、多西环素(doxycycline)、土霉素(oxytetracycline)、罗利环素(rolitetracycline);
各种其他种类,例如:丁萘脒(bunamidine)、尼立达唑(niridazole)、雷琐太尔(resorantel)、omphalotin、奥替普拉(oltipraz)、硝硫氰酯(nitroscanate)、硝碘酚腈(nitroxynil)、奥沙尼喹(oxamniquin)、mirasan、米拉西尔(miracil)、硫坎酮(lucanthon)、羟胺硫蒽酮(hycanthon)、海涛林(hetolin)、依米丁(emetin)、乙胺嗪(diethylcarbamazine)、双氯酚(dichlorophen)、地芬尼太(diamfenetide)、氯硝西泮(clonazepam)、苄酚宁(bephenium)、硝硫氰胺(amoscanate)、氯舒隆(clorsulon)。
抗原生动物活性化合物包括但不限于以下活性化合物:
三嗪类,例如:地克珠利(diclazuril)、帕那珠利(ponazuril)、来曲珠利(letrazuril)、托曲珠利(toltrazuril);
聚醚离子载体类,例如:莫能菌素(monensin)、盐霉素(salinomycin)、马度米星(maduramicin)、甲基盐霉素(narasin);
大环内酯类,例如:米尔倍霉素(milbemycin)、红霉素(erythromycin);
喹诺酮类,例如:恩氟沙星(enrofloxacin)、普拉沙星(pradofloxacin);
奎宁类,例如:氯喹(chloroquine);
嘧啶类,例如:乙胺嘧啶(pyrimethamine);
磺酰胺类,例如:磺胺喹噁啉(sulfaquinoxaline)、甲氧苄氨嘧啶(trimethoprim)、磺胺氯吡嗪(sulfaclozin);
硫胺素类,例如:安普罗铵(amprolium);
林可胺类,例如:克林霉素(clindamycin);
碳酰苯胺类,例如:咪多卡(imidocarb);
硝基呋喃类,例如:硝呋莫司(nifurtimox);
喹唑啉酮生物碱类,例如:卤夫酮(halofuginone);
各种其他种类,例如:奥沙尼喹(oxamniquin)、巴龙霉素(paromomycin);
来自微生物的疫苗或抗原,所述微生物为例如:罗氏巴贝斯虫亚种(Babesiacanis rossi)、柔嫩艾美耳球虫(Eimeria tenella)、早熟艾美尔球虫(Eimeria praecox)、毒害艾美球虫(Eimeria necatrix)、和缓艾美球虫(Eimeria mitis)、巨型艾美耳球虫(Eimeria maxima)、布氏艾美耳球虫(Eimeria brunetti)、堆型艾美耳球虫(Eimeriaacervulina)、韦氏巴贝斯虫亚种(Babesia canis vogeli)、婴儿利什曼虫(Leishmaniainfantum)、犬巴贝斯虫亚种(Babesia canis canis)、胎生网尾线虫(Dictyocaulusviviparus)。
视情况,所提及的所有混合组分还可与合适的碱或酸形成盐,如果它们基于其官能团能够形成盐的话。
病媒防治
式(I)的化合物还可用于病媒防治。在本发明的上下文中,病媒为节肢动物,尤其是昆虫或蛛形纲动物,其能够将病原体例如病毒、蠕虫、单细胞生物和细菌从贮主(植物、动物、人等)传播给宿主。病原体可以机械地传播给宿主(例如通过无刺蝇(non-stinging)传播沙眼),或者可以在注射后传播给宿主(例如通过蚊传播疟原虫)。
病媒以及它们传播的疾病或病原体的实例为:
1)蚊
-按蚊属:疟疾、丝虫病;
-库蚊属:日本脑炎、丝虫病、其他病毒性疾病、其他蠕虫传播;
-伊蚊属:黄热病、登革热、其他病毒性疾病、丝虫病;
-蚋科:蠕虫传播,尤其是盘尾丝虫(Onchocerca volvulus);
-毛蠓科:利什曼病传播;
2)虱:皮肤感染、流行性斑疹伤寒(epidemic typhus);
3)跳蚤:鼠疫、地方性斑疹伤寒、绦虫;
4)蝇:昏睡病(锥虫病(trypanosomiasis));霍乱、其他细菌性疾病;
5)螨:壁虱病、流行性斑疹伤寒、立克次氏体痘、土拉菌病、圣路易斯脑炎(SaintLouis encephalitis)、蜱媒脑炎(tick-borne encephalitis)(TBE)、克里米亚-刚果出血热(Crimean-Congo haemorrhagic fever)、疏螺旋体病(borreliosis);
6)蜱:borelliosis,如Borrelia bungdorferi sensu lato.、达氏疏螺旋体(Borrelia duttoni)、蜱媒脑炎、Q热(贝氏柯克斯体(Coxiella burnetii))、焦虫病(babesia)(犬巴贝斯虫(Babesia canis canis))、埃立克体病。
在本发明的上下文中,病媒的实例为昆虫,例如蚜虫、蝇、叶蝉或蓟马(thrip),其可向植物传播植物病毒。能够传播植物病毒的其他病媒是蜘蛛螨、虱、甲虫和线虫。
在本发明的上下文中,病媒的其他实例为昆虫和蛛形纲动物,例如蚊,尤其是伊蚊属、按蚊属,例如冈比亚按蚊(A.gambiae)、阿拉伯按蚊(A.arabiensis)、不吉按蚊(A.funestus)、大劣按蚊(A.dirus)(疟疾)和库蚊属、毛蠓科,如白蛉属、罗岭属、虱、跳蚤、蝇、螨和蜱,其可向动物和/或人类传播病原体。
如果式(I)的化合物为抗性突破(resistance-breaking)的,则病媒防治也是可能的。
式(I)的化合物适用于预防由病媒传播的疾病和/或病原体。因此,本发明的另一方面为式(I)的化合物在例如农业、园艺、林业、园林以及休闲设备中、以及在材料和贮存产品的保护中用于病媒防治的用途。
工业材料的保护
式(I)的化合物适用于保护工业材料免受昆虫的侵害或破坏,所述昆虫例如来自鞘翅目、膜翅目、等翅目、鳞翅目、啮虫目和衣鱼目(Zygentoma)。
在本发明的上下文中,工业材料应理解为意指无生命材料,例如,优选塑料、粘合剂、胶料、纸和卡片、皮革、木材、加工的木制品和涂料组合物。特别优选本发明的用于保护木材的用途。
在另一实施方案中,式(I)的化合物与至少一种其他杀昆虫剂和/或至少一种杀真菌剂一起使用。
在另一实施方案中,式(I)的化合物采取即用型农药的形式,意味着它不需要进一步修饰即可施用于所述材料。有用的其他杀昆虫剂或杀真菌剂特别地包括上述提及的那些。
出乎意料地,还发现式(I)的化合物可用于保护与盐水或微咸水接触的物体免受沾污,所述物体特别是船体、隔板、网、建筑物、系泊设备及信号体系。同样可以将式(I)的化合物单独地或与其他活性化合物组合用作防污剂。
卫生领域中动物害虫的防治
式(I)的化合物适用于防治卫生领域的动物害虫。更具体而言,本发明可以用于室内保护领域、卫生保护领域以及储存产品的保护,尤其是用于防治密闭空间中遇到的昆虫、蛛形纲动物、壁虱和螨,所述密闭空间为例如住所、工厂大厅、办公室、车辆舱室、动物育种设施。为了防治动物害虫,将式(I)的化合物单独使用或与其他活性化合物和/或助剂组合使用。其优选用于室内杀昆虫剂产品中。式(I)的化合物有效地对抗敏感性物种及抗性物种,以及其全部的发育阶段。
这些害虫包括例如下述害虫:蛛形纲,蝎目(Scorpiones)、蜘蛛目(Araneae)和盲蛛目(Opiliones);唇足纲和倍足纲;昆虫纲蜚蠊目、鞘翅目、革翅目、双翅目、异翅亚目、膜翅目、等翅目、鳞翅目、虱目、啮虫目、跳跃亚目(Saltatoria)或直翅目、蚤目和衣鱼目;软甲纲等足目。
施用如下进行:例如,气溶胶、无压喷雾器产品如泵式喷雾器和雾化喷雾器、自动雾化系统、雾化器、泡沫、凝胶、具有由纤维素或塑料制成的蒸发器片的蒸发器产品、液体蒸发器、凝胶和薄膜蒸发器、螺旋桨驱动的蒸发器、无动力(energy-free)或无源(passive)的蒸发系统、蛾纸、蛾袋和蛾胶中,作为颗粒剂或粉剂,用于撒播的诱饵或诱饵站。
以下制备和用途实施例阐述本发明而不限制本发明。
制备实施例
合成实施例编号1
1-(2-氰基乙基)-3-[(2,6-二氯苯基)氨基甲酰基]咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(化合物编号I-016)
1.1-(2-氰基乙基)-3-甲氧基羰基咪唑并[1,2-a]吡啶-4-鎓-2-醇盐的合成
将溶于5ml二氧六环的2,3-二氯-3-氧代丙酸甲酯(已知于Tetrahedron 1993,49,9447-9452)(2.85g,16.6mmol)缓慢滴加至3-(2-吡啶基氨基)丙腈(已知于WO2016171053)(650mg,4.41mmol)和三乙胺(536mg,5.30mmol)在二氧六环(15ml)中的溶液中,然后将混合物在室温下搅拌3小时。反应混合物用二氯甲烷稀释并用水洗涤,分离有机相并用硫酸镁干燥。随后通过减压蒸馏除去溶剂,将残余物吸附于硅胶上并使用流动相二氯甲烷/2-丙醇(92:8)进行色谱分离。这得到264mg(理论值的24%)1-(2-氰基乙基)-3-甲氧基羰基咪唑并[1,2-a]吡啶-4-鎓-2-醇盐。HPLC-MS:logP=0.39;mass(m/z):246.1;1H NMR(D6-DMSO):δ2.96(m,2H),3.73(s,3H),4.27(m,2H),7.34(m,1H),7.76(m,2H),9.46(d,1H)。
2.1-(2-氰基乙基)-3-[(2,6-二氯苯基)氨基甲酰基]咪唑并[1,2-a]吡啶-4-鎓-2-醇盐的合成
首先将2,6-二氯苯胺(297mg,1.83mmol)加入甲苯中,在0℃下滴加三甲基铝于甲苯中的2M溶液(132mg,1.83mmol),然后将混合物搅拌20分钟。随后,加入1-(2-氰基乙基)-3-甲氧基羰基咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(150mg,0.36mmol)于二氯甲烷(5ml)中的溶液,并将混合物在75℃下搅拌16小时。对于后处理,首先将反应混合物与15ml浓度为15%的酒石酸钾钠溶液一起搅拌,然后用二氯甲烷重复萃取。有机相用水洗涤并用硫酸镁干燥。在通过减压蒸馏除去溶剂后,将残余物吸附于硅胶上并使用流动相二氯甲烷/2-丙醇(92:8)进行色谱分离。这得到39mg(理论值的26%)1-(2-氰基乙基)-3-[(2,6-二氯苯基)氨基甲酰基]咪唑并[1,2-a]吡啶-4-鎓-2-醇盐。HPLC-MS:logP=1.81;mass(m/z):375.0;1H NMR(D6-DMSO):δ3.06(m,2H),4.40(m,2H),7.37(m,2H),7.56(m,2H),7.78(m,1H),7.90(m,1H),9.55(d,1H),9.73(s,1H)。
合成实施例编号2
3-(2,2,2-三氟乙酰基)-1-(2,2,2-三氟乙基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(化合物编号I-047)
1.3-甲氧基羰基-1-(2,2,2-三氟乙基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐的合成
将溶于2ml二氧六环的2,3-二氯-3-氧代丙酸甲酯(已知于Tetrahedron 1993,49,9447-9452)缓慢滴加至N-(2,2,2-三氟乙基)吡啶-2-胺(200mg,1.13mmol)和三乙胺(138mg,1.36mmol)于二氧六环(5ml)中的溶液中,然后将混合物在50℃下搅拌3小时。反应混合物用二氯甲烷稀释并用水洗涤,分离有机相并用硫酸镁干燥。通过减压蒸馏除去溶剂后,将残余物吸附于硅胶上并使用流动相环己烷/乙酸乙酯进行色谱分离。这得到13mg(理论值的4%)3-甲氧基羰基-1-(2,2,2-三氟乙基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐。HPLC-MS:logP=1.01;mass(m/z):275.0;1-HNMR(D6-DMSO):δ3.74(s,3H)4.93(q,2H)7.32-7.47(m,1H)7.69-7.77(m,1H)7.78-7.86(m,1H)9.52(d,1H)。
2.2-氧-1-(2,2,2-三氟乙基)咪唑并[1,2-a]吡啶-4-鎓-3-甲酸锂的合成
首先,将3-甲氧基羰基-1-(2,2,2-三氟乙基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(680mg,2.48mmol)加入THF(50ml)与水(10ml)的混合物中,加入氢氧化锂(119mg,4.96mmol),然后将混合物在40℃下搅拌16小时。从反应溶液中过滤出沉淀的固体并干燥。这得到400mg(理论值的60%)2-氧-1-(2,2,2-三氟乙基)咪唑并[1,2-a]吡啶-4-鎓-3-甲酸锂;1H NMR(D6-DMSO):δ5.01(q,2H)7.21-7.35(m,1H)7.58(ddd,1H)7.68(d,1H)10.05(d,1H)。
3.2-氧代-1-(2,2,2-三氟乙基)-2,3-二氢-1H-咪唑并[1,2-a]吡啶-4-鎓氯化物的合成
将2-氧-1-(2,2,2-三氟乙基)咪唑并[1,2-a]吡啶-4-鎓-3-甲酸锂(400mg,1.53mmol)悬浮于二氧六环(1ml)中。在小心加入4N盐酸(0.77ml,3.07mmol)后,将混合物在室温下再搅拌4小时。通过抽滤过滤出所得的沉淀物并将其干燥。这得到370mg(理论值的87%)2-氧代-1-(2,2,2-三氟乙基)-2,3-二氢-1H-咪唑并[1,2-a]吡啶-4-鎓氯化物;1HNMR(D6-DMSO):δ4.98(q,2H)5.51(s,2H)7.75(t,1H)8.05(d,1H)8.62(t,1H)8.93(d,1H)。
4.3-(2,2,2-三氟乙酰基)-1-(2,2,2-三氟乙基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐的合成
首先,将2-氧代-1-(2,2,2-三氟乙基)-2,3-二氢-1H-咪唑并[1,2-a]吡啶-4-鎓氯化物(100mg,0.39mmol)加入二氧六环(2.0ml)中,并加入三乙胺(48mg,0.47mmol)。然后滴加三氟乙酸酐(100mg,0.47mmol)的二氧六环溶液(2ml),并将混合物在室温下搅拌16小时。蒸馏出溶剂并将残余物溶于二氯甲烷。溶液用水洗涤,分离有机相并用硫酸镁干燥。通过减压蒸馏除去溶剂后,将残余物吸附于硅胶上并使用流动相环己烷/乙酸乙酯进行色谱分离。这得到31.0mg(理论值的25%)3-(2,2,2-三氟乙酰基)-1-(2,2,2-三氟乙基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐。HPLC-MS:logP=1.79;mass(m/z):313.1;1H NMR(D6-DMSO):δ4.96(q,2H)7.53(dd,1H)7.87(d,1H)8.02-8.18(m,1H)9.82(d,1H)。
合成实施例编号3
3-(2-甲氧基-2-氧代乙酰基)-1-(2,2,2-三氟乙基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(化合物编号I-051)
首先,将2-氧代-1-(2,2,2-三氟乙基)-2,3-二氢-1H-咪唑并[1,2-a]吡啶-4-鎓氯化物(100mg,0.39mmol)加入二氧六环(2.0ml)中,并加入三乙胺(201mg,1.98mmol)。然后滴加2-氯-2-氧代乙酸甲酯(58mg,0.47mmol)的二氧六环溶液(2ml),并将混合物在室温下搅拌16小时。将反应混合物进行蒸馏并将残余物溶于二氯甲烷中。将溶液用水洗涤,分离有机相并用硫酸镁干燥。通过减压蒸馏除去溶剂后,将残余物吸附于硅胶上并使用流动相环己烷/乙酸乙酯进行色谱分离。这得到35.0mg(理论值的29%)3-(2-甲氧基-2-氧代乙酰基)-1-(2,2,2-三氟乙基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐。HPLC-MS:logP=1.18;mass(m/z):303.0;1H NMR(D6-DMSO):δ3.79(s,3H)4.92(q,2H)7.41-7.56(m,1H)7.86(d,1H)8.04(td,1H)9.62(d,1H)。
合成实施例编号4
3-(2-氯乙酰基)-1-(2-氰基乙基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(化合物编号I-084)
将氯乙酰氯(5824mg,51.5mmol)经5分钟滴加至3-(2-吡啶基氨基)丙腈(由WO2016171053已知)(3300mg,22.4mmol)于甲苯(18mL)和二甲基乙酰胺(4.8ml)中的溶液中,并首先将混合物在50℃下搅拌1小时,然后在室温下搅拌18小时。将反应混合物蒸发至干并将残余物吸附于硅胶上,使用流动相二氯甲烷/2-丙醇(92:8)进行色谱分离。这得到2480mg(理论值的41%)3-(2-氯乙酰基)-1-(2-氰基乙基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐。HPLC-MS:logP=0.80;mass(m/z):264.1;1H NMR(D6-DMSO):δ2.99(m,2H),4.30(m,2H),4.79(s,2H),7.41(m,1H),7.88(m,1H),7.93(d,1H),9.85(m,1H)。
合成实施例编号5
1-(2-氰基乙基)-3-[2-(1-甲基环丙氧基)-2-氧代-乙酰基]咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(化合物编号I-089)
1.3-(2-氧代-3H-咪唑并[1,2-a]吡啶-4-鎓-1-基)丙腈四氟硼酸盐的合成
将来自合成实施例4的3-(2-氯乙酰基)-1-(2-氰基乙基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(150mg,0.56mmol)悬浮于氯仿(5mL)中,并加入浓度为50%的四氟硼酸(124.8mg,0.71mmol)。然后将混合物在室温下搅拌16小时。在50℃、4毫巴下,将反应混合物蒸发至干,得到粘性油状的3-(2-氧代-3H-咪唑并[1,2-a]吡啶-4-鎓-1-基)丙腈四氟硼酸盐,其无需进一步纯化而用于下一反应步骤。
1.1-(2-氰基乙基)-3-[2-(1-甲基环丙氧基)-2-氧代乙酰基]咪唑并[1,2-a]吡啶-4-鎓-2-醇盐的合成
首先,将1-甲基环丙-1-醇(500mg,6.93mmol)加入二氯甲烷(10.4mL)中,加入草酰氯(924.1mg,7.28mmol),并将混合物在室温下搅拌3小时。将1当量的反应溶液直接用于反应步骤3。
2.1-(2-氰基乙基)-3-[2-(1-甲基环丙氧基)-2-氧代乙酰基]咪唑并[1,2-a]吡啶-4-鎓-2-醇盐的合成
将二氯甲烷(2ml)加入来自反应步骤1的3-(2-氧代-3H-咪唑并[1,2-a]吡啶-4-鎓-1-基)丙腈四氟硼酸盐中,随后在5℃下,加入来自反应步骤2的2-氯-2-氧代-乙酸1-甲基环丙酯(138.7mg,0.85mmol)的反应溶液中,然后加入三乙胺(287.8mg,2.84mmol)。将反应混合物搅拌3小时,然后溶于水/二氯甲烷,分离有机相并蒸发至干。将残余物吸附于硅胶上并使用流动相二氯甲烷/2-丙醇(92:8)进行色谱分离。这得到60mg(理论值的28%)1-(2-氰基乙基)-3-[2-(1-甲基环丙氧基)-2-氧代-乙酰基]咪唑并[1,2-a]吡啶-4-鎓-2-醇盐。HPLC-MS:logP=1.33;mass(m/z):313.1;1H NMR(D6-DMSO):δ0.88(m,2H),1.03(m,2H),1.59(s,3H),2.95(m,2H),4.26(m,2H),7.42(m,1H),7.89(m,1H),7.97(d,1H),9.55(m,1H)。
合成实施例编号6
3-(2-氯乙酰基)-1-(2-氰基乙基)-8-甲基-咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(化合物编号I-095)
类似于合成实施例编号4,将3-[(3-甲基-2-吡啶基)氨基]丙腈(通过合成实施例编号4中的3-(2-吡啶基氨基)丙腈的方法获得)(950mg,5.89mmol)与氯乙酰基氯(1530mg,13.5mmol)进行反应,得到350mg(理论值的36%)3-(2-氯乙酰基)-1-(2-氰基乙基)-8-甲基-咪唑并[1,2-a]吡啶-4-鎓-2-醇盐。HPLC-MS:logP=0.80;mass(m/z):277.1;1H NMR(D6-DMSO):δ2.05(s,3H),2.78(m,2H),3.58(m,2H),6.30(s,2H),6.50(m,1H),7.26(m,1H),7.89(m,1H)。
合成实施例编号7
1-(2-氰基乙基)-8-甲基-3-(2,2,2-三氟乙酰基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(化合物编号I-027)
1.3-(8-甲基-2-氧代-3H-咪唑并[1,2-a]吡啶-4-鎓-1-基)丙腈四氟硼酸盐的合成
将来自合成实施例6的3-(2-氯乙酰基)-1-(2-氰基乙基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(150mg,0.54mmol)悬浮于氯仿(5mL)中,并加入浓度为50%的四氟硼酸(118.5mg,0.67mmol)。然后将混合物在室温下搅拌16小时。在50℃、4毫巴下,将反应混合物蒸发至干,得到粘性油状的3-(8-甲基-2-氧代-3H-咪唑并[1,2-a]吡啶-4-鎓-1-基)丙腈四氟硼酸盐,其无需进一步纯化而用于下一反应步骤。
2.1-(2-氰基乙基)-8-甲基-3-(2,2,2-三氟乙酰基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐的合成
将二氯甲烷(5ml)加入来自反应步骤1的3-(8-甲基-2-氧代-3H-咪唑并[1,2-a]吡啶-4-鎓-1-基)丙腈四氟硼酸盐(156mg,0.54mmol)中,随后在5℃下,加入三氟乙酸酐(170.1mg,0.81mmol),然后加入三乙胺(273.2mg,2.70mmol)。将反应混合物搅拌3小时并溶于水/二氯甲烷,分离有机相并蒸发至干。将残余物吸附于硅胶上并使用流动相二氯甲烷/2-丙醇(92:8)进行色谱分离。这得到66mg(理论值的40.7%)1-(2-氰基乙基)-8-甲基-3-(2,2,2-三氟乙酰基)咪唑并[1,2-a]吡啶-4-鎓-2-醇盐。HPLC-MS:logP=1.35;mass(m/z):297.1;1H NMR(D6-DMSO):δ2.70(s,3H),3.02(m,2H),4.42(m,2H),7.38(m,1H),7.83(m,1H),9.78(m,1H)。
合成实施例编号8
1-(2-氰基乙基)-3-[3-(三氟甲基)苯甲酰基]咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(化合物编号I-004)
将二氯甲烷(5ml)加入来自合成实施例5反应步骤1的3-(2-氧代-3H-咪唑并[1,2-a]吡啶-4-鎓-1-基)丙腈四氟硼酸盐(150mg,0.54mmol)中,并加入3-(三氟甲基)苯甲酰氯(170.6mg,0.81mmol),然后加入三乙胺(275.9mg,2.72mmol)。将反应混合物搅拌16小时,然后溶于水/二氯甲烷,分离有机相并蒸发至干。将残余物吸附于硅胶上并使用流动相二氯甲烷/2-丙醇(92:8)进行色谱分离。这得到100mg(理论值的50%)1-(2-氰基乙基)-3-[3-(三氟甲基)苯甲酰基]咪唑并[1,2-a]吡啶-4-鎓-2-醇盐。HPLC-MS:logP=1.35;mass(m/z):359.1;1H NMR(D6-DMSO):δ2.95(m,2H),4.27(m,2H),7.43(m,1H),7.67(m,1H),7.6-8.2(m,5H),10.03(m,1H)。
合成实施例编号9
1-(2-氰基乙基)-3-[(2E)-2-甲氧基亚氨基乙酰基]咪唑并[1,2-a]吡啶-4-鎓-2-醇盐(化合物编号I-094)
将二氯甲烷(5ml)加入来自合成实施例5反应步骤1的3-(2-氧代-3H-咪唑并[1,2-a]吡啶-4-鎓-1-基)丙腈四氟硼酸盐(150mg,0.54mmol)中,并加入(2E)-2-甲氧基亚氨基乙酰氯(已知于DE3208330)(103.7mg,0.85mmol),然后加入三乙胺(275.9mg,2.84mmol)。将反应混合物搅拌16小时,然后溶于水/二氯甲烷,分离有机相并蒸发至干。将残余物吸附于硅胶上并使用流动相二氯甲烷/2-丙醇(92:8)进行色谱分离。得到40mg(理论值的22%)1-(2-氰基乙基)-3-[(2E)-2-甲氧基亚氨基乙酰基]咪唑并[1,2-a]吡啶-4-鎓-2-醇盐。HPLC-MS:logP=0.73;mass(m/z):273.1;1H NMR(D6-DMSO):δ2.97(m,2H),3.96(s,3H),4.29(m,2H),7.43(m,1H),7.8-8.0(m,2H),8.9(s,1H),9.95(m,1H)。
下表1中记载的本发明的化合物同样是根据或以类似于上文所述的合成实施例获得的本发明优选的式(I)的化合物。它们均基于式(I-1)的结构。
表1
除非已在合成实施例1至9中给出,否则化合物的1H NMR数据如表1:
在pH 2.7下,使用流动相乙腈(含0.1%甲酸)和水,通过LC-MS在酸性范围内测定[M+H]+;线性梯度为10%乙腈至95%乙腈,仪器:Agilent 1100LC系统、Agilent MSD系统、HTS PAL。
上文表格和制备实施例中给出的logP值根据EEC指令79/831附录V.A8通过HPLC(高效液相色谱法)使用反相柱(C18)测定。温度为43℃。用非支链的链烷-2-酮(具有3-16个碳原子)进行校准,其logP值是已知的。
使用装备有样品流量探头(sample flow head)(容量60μl)的BrukerAvance 400或Bruker Avance III 600测定1H NMR数据,其中四甲基硅烷作为参比(0.0),溶剂为CD3CN、CDCl3或D6-DMSO。
NMR峰列表方法
所选实施例的1H-NMR数据以1H-NMR峰列表的形式表示。对于每个信号峰,首先列出以ppm计的δ值,然后在圆括号内列出信号强度。不同信号峰的δ值-信号强度数对通过分号彼此间隔列出。
因此,一个实施例的峰列表具有以下形式:
δ1(强度1);δ2(强度2);……;δi(强度i);……;δn(强度n)
尖峰信号的强度与NMR谱的打印实施例中的信号高度(以厘米计)相关,并且显示出信号强度的真实比例。对于宽峰信号,与谱图中最强信号相比,可以显示数个峰或信号的中间部分及其相对强度。
1H NMR谱的化学位移的校准使用四甲基硅烷和/或溶剂的化学位移来完成,特别是在DMSO中测定的波谱的情况下。因此,四甲基硅烷峰可以但不一定出现在NMR峰列表中。
1H NMR峰的列表类似于常规1H NMR打印图像,因此,其通常含有在常规NMR说明中列出的所有峰。
另外,如同常规1H NMR的打印图像,其可显示出溶剂信号、目标化合物的立体异构体(其同样形成本发明主题的一部分)的信号、和/或杂质的峰。
在记录溶剂和/或水的δ范围内的化合物信号时,我们的1H NMR峰的列表显示出标准溶剂峰,例如在DMSO-D6中的DMSO的峰和水的峰,这通常具有平均较高的强度。
目标化合物的立体异构体的峰和/或杂质的峰通常具有比目标化合物(例如具有>90%的纯度)的峰平均更低的强度。
此类立体异构体和/或杂质对于特定制备方法来说可以是特有的。因此,通过参考“副产品指纹”,它们的峰可有助于识别我们的制备方法的再现性。
如果需要的话,通过已知方法(MestreC,ACD模拟,以及凭经验评估的预期值)计算目标化合物的峰的专业人员可以任选地使用额外的强度过滤器分离出目标化合物的峰。这种分离类似于常规1HNMR说明中所讨论的峰拾取。
1H NMR峰列表的其他细节可以在Research Disclosure Database Number564025中找到。
用途实施例
以下实施例证明了本发明化合物的杀虫和杀螨作用。在这里,所提及的本发明化合物是指表1中列出的具有相应的参考数字(编号)的化合物:
猫栉头蚤(Ctenocephalidesfelis)-与成年猫蚤(catflea)的体外接触测试
为了涂覆试管,首先将9mg的活性化合物溶解在1ml分析纯丙酮中,然后用分析纯丙酮稀释到所需浓度。将250μl溶液通过在定轨摇床(以30rpm的摇摆旋转速度持续2h)上旋转和摇摆而均匀分布在25ml试管的内壁和底部上。对于900ppm的活性化合物溶液和44.7cm2内表面,如果均匀分布,则获得基于面积计(area-based)的5μg/cm2的剂量。
当溶剂蒸发后,在试管中放入5-10只成年猫蚤(猫栉头蚤),用有孔的塑料盖密封,并在室温和环境湿度下水平放置培育。48h后,测定功效。为此,将试管直立并敲击猫蚤使之到试管底部。将在底部保持静止或以不协调方式活动的蚤视为死亡或将要死亡。
如果在本测试中在5μg/cm2的施用率下获得至少80%的功效,则该物质显示出对猫栉头蚤良好的功效。100%的功效表示所有蚤均死亡或将要死亡。0%的功效表示没有蚤受到伤害。
在本测试中,例如,下列制备实施例的化合物在5μg/cm2(500ga.i/ha)的施用率下显示出100%的功效:I-016
在本测试中,例如,下列制备实施例的化合物在5μg/cm2(500ga.i/ha)的施用率下显示出80%的功效:I-047
猫栉头蚤-经口测试(oral test)
溶剂:二甲基亚砜
为了制备合适的活性化合物制剂,将10mg的活性化合物与0.5ml的二甲基亚砜混合。用柠檬酸化的牛血稀释,得到所需浓度。
将约20只未进食的成年猫蚤(猫栉头蚤)放置到顶部和底部用纱布密封的容器内。将底部用石蜡膜密封的金属圆筒放置在容器上。圆筒中含有血液/活性化合物制剂,其可以被跳蚤透过石蜡膜吸取。
2天后,测定以%计的杀死率。100%表示所有猫蚤都已被杀死;0%表示没有猫蚤被杀死。
在本测试中,例如,下列制备实施例的化合物在100ppm的施用率下显示出85%的功效:I-018
家蝇(Musca domestica)测试
溶剂:二甲基亚砜
为制备合适的活性化合物制剂,将10mg的活性化合物与0.5ml二甲基亚砜混合,并用水将该浓缩物稀释到所需浓度。
在含有用糖溶液和所需浓度的活性化合物制剂处理的海绵的容器中放入10只成年家蝇(houseflies)(家蝇)。
2天后,测定以%计的杀死率。100%表示所有家蝇都已被杀死;0%表示没有家蝇被杀死。
在本测试中,例如,下列制备实施例的化合物在100ppm的施用率下显示出100%的功效:I-018
带斑黄瓜条叶甲(Diabrotica balteata)-喷洒测试
溶剂:78重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,使用所述重量份的溶剂来溶解1重量份的活性化合物,并补充含有浓度为1000ppm乳化剂的水直至获得所需浓度。为了制备其他测试浓度,用含有乳化剂的水稀释制剂。
将预先膨胀的小麦籽粒(小麦(Triticum aestivum))在装有琼脂和少量水的多孔板中培育一天(每个腔5粒种子)。用所需浓度的活性化合物制剂喷洒发芽的小麦籽粒。随后,每个腔感染10-20只带斑黄瓜条叶甲的甲虫幼虫。
7天后,测定以%计的功效。100%表示所有小麦植物都像未处理的未感染对照一样生长;0%表示没有小麦植物生长。
在本测试中,例如,下列制备实施例的化合物在160μg/孔的施用率下显示出100%的功效:I-047
桃蚜(Myzus
persicae)-经口测试
溶剂:100重量份的丙酮
为了制备合适的活性化合物制剂,将1重量份的活性化合物与所述重量份的溶剂混合,并补充水直至所需浓度。
将50μl活性化合物制剂转移至微量滴定板,并用150μl的IPL41昆虫培养基(33%+15%糖)补充至200μl的最终体积。随后,使用石蜡膜密封该板,在第二个微量滴定板内桃蚜(Myzus persicae)的混合种群能够刺破石蜡膜而吸收溶液。
5天后,测定以%计的功效。100%表示所有桃蚜均已被杀死;0%表示没有桃蚜被杀死。
在本测试中,例如,下列制备实施例的化合物在4ppm的施用率下显示出100%的功效:I-002、I-003、I-004、I-007、I-018、I-051、I-082、I-085、I-086、I-091、I-094
在本测试中,例如,下列制备实施例的化合物在4ppm的施用率下显示出90%的功效:I-005、I-081、I-083、I-087、I-092、I-093
桃蚜(Myzus
persicae)-喷洒测试
溶剂:78重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,使用所述重量份的溶剂来溶解1重量份的活性化合物,并补充含有浓度为1000ppm乳化剂的水,直至获得所需浓度。为了制备其他测试浓度,用含有乳化剂的水稀释制剂。
在被所有阶段的桃蚜(Myzus persicae)侵染的大白菜叶(白菜(Brassicapekinensis))的叶面上喷洒所需浓度的活性化合物制剂。
5天后,测定以%计的功效。100%表示所有桃蚜均已被杀死;0%表示没有桃蚜被杀死。
在本测试中,例如,下列制备实施例的化合物在500g/ha的施用率下显示出100%的功效:I-012、I-016。
在本测试中,例如,下列制备实施例的化合物在500g/ha的施用率下显示出90%的功效:I-007、I-089。
Claims (20)
1.式(I)的化合物
其中
T代表氢、C(R5a)(R5b)(R5c)、C2-C8-烯基、C3-C8-炔基或C3-C8-环烷基,其中C2-C8-烯基、C3-C8-炔基和C3-C8-环烷基可各自任选地被单取代至三取代且取代基彼此独立地选自卤素和/或可各自任选地被单取代且取代基选自氰基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-环烷基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、芳基、杂芳基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基,其中芳基、杂芳基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
或
T代表芳基、C1-C6-亚烷基二氧基芳基、杂芳基、C3-C8-杂环基、C3-C8-氧代杂环基或C3-C8-二氧代杂环基,其中上述基团可各自任选地被单取代至五取代且取代基彼此独立地选自卤素、硝基、氨基、氰基、SF5、SCN、C1-C6-烷基氨基、二-(C1-C6-烷基)氨基、羟基、COOH、C1-C6-烷基、C3-C6-环烷基、C3-C6-杂环基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C3-C6-卤代环烷基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、SH、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、三-(C1-C6-烷基)甲硅烷基、芳基、杂芳基、杂环基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基,其中芳基、杂芳基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
或
T代表N(R7a)(R7b)或N(R8)-N(R11a)(R11b),
或
T代表C(=W)R12或C(=O)OR13,
W代表O或N-OR15,
G代表C1-C6-烷基或C2-C6-烯基,其中上述基团各自被卤素单取代至五取代和/或被以下基团单取代至二取代:氰基、C1-C4-烷氧基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、C1-C4-羰基-C1-C4-烷氧基或C1-C4-烷氧基亚氨基-C1-C4-烷基,
R1在每种情况下代表氢、卤素、氰基、硝基、SF5、SCN、氨基、C1-C6-烷基氨基、二-(C1-C6)-烷基氨基、羟基、COOH、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C3-C6-卤代环烷基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C2-C6-烯氧基、C3-C6-炔基、C3-C6-炔氧基、SH、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷硫基、C1-C6-卤代烷基亚磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基亚氨基-C1-C6-烷基、C1-C6-烷氧基羰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、芳基、杂芳基、芳基-C1-C6-烷基或杂芳基-C1-C6-烷基,
其中芳基、杂芳基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基可各自任选地被单取代或多取代且取代基彼此独立地选自卤素、氰基、硝基、羟基、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基和C1-C6-烷硫基,
或
两个基团R1一起形成5元或6元脂族环、芳族环、杂芳族环或杂环,所述环可任选地含有1至2个选自O、S和N的原子且其可任选地被单取代或多取代,其中取代基彼此独立地选自卤素和C1-C4-烷基,
p代表0、1、2或3,
R5a和R5b彼此独立地代表氢、卤素、氰基、C1-C6-烷基、C1-C6-卤代烷基或C1-C6-烷氧基,
R5c代表氢、氟、氯、溴、氰基、C1-C6-烷氧基羰基、C1-C6-烷基、C1-C6-烷氧基、C3-C8-环烷基、C2-C6-烯基或C2-C6-炔基,其中C1-C6-烷基、C3-C8-环烷基、C2-C6-烯基和C2-C6-炔基可各自任选地被单取代至五取代且取代基彼此独立地选自卤素和/或可各自任选地被单取代且取代基选自硝基、氰基、C1-C6-卤代烷基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基羰基氨基、C1-C6-烷基氨基羰基、二-(C1-C6-烷基)氨基羰基、C1-C6-烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷氧基亚氨基-C1-C6-烷基、芳基、杂芳基和杂环基,其中芳基、杂芳基和杂环基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、C1-C6-烷硫基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、C1-C6-烷基羰基氨基、芳基和杂芳基,其中芳基和杂芳基本身可各自任选地被单取代或多取代且取代基彼此独立地选自卤素、氰基、硝基、羟基、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基和C1-C6-烷硫基,
或
R5c代表芳基、C-键合的杂芳基、N-键合的杂芳基、C3-C8-杂环基、C3-C8-氧代杂环基或C3-C8-二氧代杂环基,其中上述基团可各自任选地被单取代至五取代且取代基彼此独立地选自卤素、硝基、氨基、氰基、SF5、SCN、C1-C6-烷基氨基、二-(C1-C6-烷基)氨基、羟基、COOH、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C3-C6-卤代环烷基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、SH、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6-烷基)氨基羰基、C1-C6-烷基羰基氨基、三-(C1-C6-烷基)甲硅烷基、芳基、杂芳基、杂环基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基,其中芳基、杂芳基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、羟基、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-卤代烷基、C1-C6-烷氧基和C1-C6-卤代烷氧基或C1-C6-烷硫基,
R13和R15彼此独立地代表氢,或
代表C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C3-C6-环烷基-C1-C6-烷基、杂环基、杂环基-C1-C6-烷基、芳基、杂芳基、芳基-C1-C6-烷基或杂芳基-C1-C6-烷基、C3-C6-氧代杂环基或C3-C6-二氧代杂环基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自硝基、氰基、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-烷基羰基、C1-C6-烷氧基亚氨基-C1-C6-烷基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、芳基和杂芳基,其中芳基和杂芳基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
R7a和R11a彼此独立地代表氢、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C6-烷基、C1-C6-烷氧基羰基、C1-C6-烷基羰基或C1-C6-烷基磺酰基,
R7b和R11b彼此独立地代表氢、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基或C3-C6-杂环基,其中C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基和C3-C6-杂环基可各自任选地被单取代至五取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自硝基、氰基、羟基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、芳基、杂芳基、杂环基和氧代杂环基,其中芳基、C3-C6-环烷基、杂芳基、杂环基和氧代杂环基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、C1-C6-烷硫基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、C1-C6-烷基羰基氨基、芳基和杂芳基,其中芳基和杂芳基本身可各自任选地被单取代或多取代且取代基彼此独立地选自卤素、氰基、硝基、羟基、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基和C1-C6-烷硫基,
或
R7b和R11b彼此独立地代表芳基或杂芳基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氨基、氰基、SF5、SCN、C1-C6-烷基氨基、二-(C1-C6)-烷基氨基、羟基、COOH、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C3-C6-卤代环烷基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、SH、C1-C6-烷硫基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基和三-(C1-C6-烷基)甲硅烷基,
或
R7a和R7b可以通过2至6个碳原子彼此连接并形成环,所述环可任选另外地含有选自O、S和N的其他原子并且可任选地被单取代至四取代且取代基彼此独立地选自C1-C2-烷基、卤素、氰基、氨基和C1-C2-烷氧基,或
R11a和R11b可以通过2至6个碳原子彼此连接并形成环,所述环可任选另外地含有选自O、S和N的其他原子并且可任选地被单取代至四取代且取代基彼此独立地选自C1-C2-烷基、卤素、氰基、氨基和C1-C2-烷氧基,或
R8代表氢、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C1-C4-烷氧基-C1-C6-烷基、C1-C6-烷氧基羰基或C1-C6-烷基羰基,
并且
R12代表氢、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基或C3-C6-杂环基,其中C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基和C3-C6-杂环基可各自任选地被单取代至五取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自硝基、氰基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、芳基、杂芳基、杂环基和氧代杂环基,其中芳基、杂芳基、杂环基和氧代杂环基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、C1-C6-烷硫基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、C1-C6-烷基羰基氨基、芳基和杂芳基,其中芳基和杂芳基本身可各自任选地被单取代或多取代且取代基彼此独立地选自卤素、氰基、硝基、羟基、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基和C1-C6-烷硫基,
或
R12代表芳基或杂芳基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氨基、氰基、SF5、SCN、C1-C6-烷基氨基、二-(C1-C6)-烷基氨基、羟基、COOH、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C3-C6-卤代环烷基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、SH、C1-C6-烷硫基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基和三-(C1-C6-烷基)甲硅烷基。
2.根据权利要求1所述的化合物,其中
T代表氢、C(R5a)(R5b)(R5c)、C2-C6-烯基、C3-C6-炔基或C3-C6-环烷基,其中C2-C6-烯基、C3-C6-炔基和C3-C6-环烷基可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基,
或
T代表芳基、C1-C6-亚烷基二氧基苯基、杂芳基或C3-C6-杂环基,其中上述基团可各自任选地被单取代至五取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C4-烷基、C3-C6-杂环基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C2-C4-烯基、C3-C4-炔基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基羰基、C3-C6-环烷基羰基、C2-C4-烯基羰基、C1-C4-卤代烷基羰基、C1-C4-烷氧基羰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基磺酰基、芳基、杂芳基、杂环基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基,其中芳基、杂芳基、芳基-C1-C6-烷基和杂芳基-C1-C6-烷基本身可各自被单取代至三取代且取代基彼此独立地选自卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
或
T代表N(R7a)(R7b)或N(R8)-N(R11a)(R11b),
或
T代表C(=W)R12或C(=O)OR13,
W代表O或N-OR15,
G代表C1-C6-烷基或C2-C6-烯基,其中上述基团各自被卤素单取代至五取代和/或被以下基团单取代至二取代:氰基、C1-C4-烷氧基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、C1-C4-羰基-C1-C4-烷氧基、C1-C4-烷氧基亚氨基-C1-C4-烷基,
R1代表氢、卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基,
p代表1或2,
R5a和R5b彼此独立地代表氢、卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基,
R5c代表氢、氟、氯、溴、氰基、C1-C4-烷氧基羰基、C1-C4-烷基、C1-C4-烷氧基、C3-C6-环烷基、C2-C6-烯基或C2-C6-炔基,其中C1-C4-烷基、C3-C6-环烷基、C2-C6-烯基和C2-C6-炔基可各自任选地被单取代至五取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自硝基、氰基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷基羰基和C1-C4-烷氧基羰基,
或
R5c代表芳基或C-键合的杂芳基,其中上述基团可各自任选地被单取代至五取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷氧基羰基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基,
或
R5c代表Y,
Y代表基团Y-1至Y-23之一,
Xb代表卤素、硝基、氰基、C1-C6-烷基、C3-C6-环烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-卤代环烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-卤代烷氧基-C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷氧基、氰基-C1-C6-烷基、C3-C6-环烷基-C1-C6-烷基、C2-C6-烯基、C3-C6-炔基、C1-C6-烷硫基、C1-C6-烷基羰基、C3-C6-环烷基羰基、C2-C6-烯基羰基、C1-C6-卤代烷基羰基、C1-C6-烷氧基羰基、C1-C6-烷基磺酰基、C1-C6-烷基亚磺酰基、C1-C6-卤代烷基磺酰基、C1-C6-烷基氨基羰基、二-(C1-C6)-烷基氨基羰基、C1-C6-烷基羰基氨基、芳基或杂芳基,其中芳基和杂芳基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、羟基、C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C1-C6-烷氧基、C1-C6-卤代烷基、C1-C6-卤代烷氧基和C1-C6-烷硫基且其中Y-13、Y-14和Y-16中的环氮原子不被以下基团取代:卤素、硝基、氰基、C1-C4-烷氧基、C1-C4-卤代烷氧基或C1-C4-烷氧基-C1-C4-烷氧基,
m代表0、1或2,
R13和R15彼此独立地代表氢,或
代表C1-C4-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C3-C6-环烷基-C1-C4-烷基、C3-C6-杂环基、C3-C6-杂环基-C1-C4-烷基、C3-C6-氧代杂环基、C3-C6-二氧代杂环基、苯基、吡啶基、苯基-C1-C4-烷基或吡啶基-C1-C4-烷基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C3-C6-环烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-烷氧基羰基、芳基和杂芳基,其中芳基和杂芳基本身可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
R7a和R11a彼此独立地代表氢、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷氧基羰基或C1-C6-烷基羰基,
R7b和R11b彼此独立地代表氢,或
彼此独立地代表C1-C6-烷基或C3-C6-环烷基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可任选地被单取代且取代基选自氰基、硝基、羟基和C1-C4-烷氧基、C3-C6-环烷基、芳基和杂芳基,其中芳基、C3-C6-环烷基和杂芳基本身可被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
或
R7b和R11b彼此独立地代表芳基或杂芳基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基,或
R7a和R7b可以通过2至6个碳原子彼此连接并形成环,所述环可任选另外地含有选自O、S和N的其他原子,并且可任选地被单取代至四取代且取代基彼此独立地选自C1-C2-烷基、氟、氯、溴和C1-C2-烷氧基,或
R11a和R11b可以通过2至6个碳原子彼此连接并形成环,所述环可任选另外地含有选自O、S和N的其他原子并且可任选地被单取代至四取代且取代基彼此独立地选自C1-C2-烷基、氟、氯、溴和C1-C2-烷氧基,或
R8代表氢、C1-C6-烷基、C3-C6-环烷基、C1-C6-烷氧基羰基或C1-C6-烷基羰基,
并且
R12代表C1-C6-烷基,其可任选地被单取代至五取代且其中取代基彼此独立地选自卤素,和/或其可任选地被单取代且其中取代基选自硝基、氰基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
或
R12代表芳基或杂芳基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基。
3.根据权利要求1或2所述的化合物,其中
T代表氢、C(R5a)(R5b)(R5c)、C2-C4-烯基、C3-C4-炔基或C3-C6-环烷基,其中C2-C4-烯基、C3-C4-炔基或C3-C6-环烷基可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基,
或
T代表苯基、C1-C4-亚烷基二氧基苯基、萘基、呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,5-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、苯硫基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、苯并呋喃基、吲哚基、苯并噻唑基、苯并噁唑基、苯并咪唑基、吡唑并吡啶基、喹啉基、异喹啉基、噌啉基、氮杂环丁烷基、氮杂环戊基、氮杂环己基、氧杂环丁基、氧杂环戊基、氧杂环己基、二氧杂环己基、硫杂环丁基、硫杂环戊基、硫杂环己基或二氢异噁唑基,其中上述基团可各自任选地被单取代至四取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代至二取代且取代基彼此独立地选自溴、硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-卤代烷基磺酰基、苯基、吡啶基和吗啉基,其中总共存在最多五个上述取代基且其中苯基和吡啶基本身可另外地各自被单取代至三取代且取代基彼此独立地选自卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
或
T代表N(R7a)(R7b),
或
T代表C(=W)R12或C(=O)OR13,
W代表O或N-OR15,
G代表C1-C4-烷基或C2-C4-烯基,其中上述基团各自被卤素单取代至三取代和/或被氰基单取代,
R1代表氢、氟、氯、甲基、乙基、甲氧基或乙氧基,
p代表1,
R5a和R5b彼此独立地代表氢、卤素、C1-C4-烷基或C1-C4-烷氧基,
R5c代表氢、氟、氯、溴、C1-C4-烷氧基羰基、C1-C4-烷基、C1-C4-烷氧基或C3-C6-环烷基,其中C1-C4-烷基和C3-C6-环烷基可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自氰基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-烷氧基羰基,
或
R5c代表苯基或C-键合的吡啶基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、硝基、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷氧基羰基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基,
或
R5c代表Y,
Y代表基团Y-2、Y-3、Y-4、Y-5、Y-6或Y-7之一,
Xb代表卤素、氰基、甲基、乙基、三氟甲基、二氟甲基、甲基氨基羰基、甲基羰基氨基、甲氧基、乙氧基、三氟甲氧基、甲硫基、乙硫基、甲基亚磺酰基、甲基磺酰基或甲氧基羰基,
m代表0、1或2,
R13和R15彼此独立地代表氢,或
代表C1-C4-烷基、C3-C6-环烷基、C3-C6-杂环基或C3-C6-二氧代杂环基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可各自任选地被单取代且取代基选自氰基、C1-C4-烷基、C1-C4-卤代烷基、C3-C6-环烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、C1-C4-烷氧基羰基、苯基和吡啶基,其中苯基和吡啶基本身可各自被单取代至三取代且取代基彼此独立地选自卤素、氰基、硝基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基,
R7a代表氢或C1-C4-烷基,
R7b代表氢,或
代表C1-C6-烷基或C3-C6-环烷基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素,和/或可任选地被单取代且取代基选自C3-C6-环烷基和苯基,其中C3-C6-环烷基和苯基本身可被单取代至三取代且取代基彼此独立地选自卤素、C1-C4-烷基、C1-C4-卤代烷基和C1-C4-烷氧基,
或
R7b代表苯基、吡啶基或吡唑基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基和C1-C4-烷基磺酰基,或
R7a和R7b可以通过2至6个碳原子彼此连接并形成环,所述环可任选另外地含有选自O、S和N的其他原子并且可任选地被单取代至三取代且取代基彼此独立地选自甲基、乙基、氟、甲氧基和乙氧基,
并且
R12代表C1-C4-烷基,其可任选地被单取代至五取代基且其中取代基彼此独立地选自卤素,
或
R12代表苯基,其可任选地被单取代至三取代基且其中取代基彼此独立地选自卤素。
4.根据权利要求1至3中任一项所述的化合物,其中
T代表氢、C(R5a)(R5b)(R5c)、乙烯基、丙烯基、环丙基、环丁基、环戊基或环己基,其中乙烯基、丙烯基、环丙基、环丁基、环戊基和环己基可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代且取代基选自氰基、甲基、乙基、三氟甲基和甲氧基,
或
T代表苯基、吡啶基、嘧啶基、苯硫基、呋喃基、吡咯基、噻唑基、异噻唑基、1,3-噁唑基、1,2-噁唑基、吡唑基、咪唑基、1,2,4-噁二唑基、吡唑并吡啶基、苯并噻唑基、苯并呋喃基、苯并噁唑基、喹啉基、氧杂环戊基或二氢异噁唑基,其中上述基团可各自任选地被单取代至四取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代至二取代且取代基彼此独立地选自溴、氰基、甲基、乙基、二氟甲基、三氟甲基、三氟乙基、五氟乙基、三氟丙基、甲氧基、乙氧基、三氟甲氧基、甲硫基、甲基亚磺酰基、甲基磺酰基、吗啉基和苯基,
或
T代表N(R7a)(R7b),
或
T代表C(=W)R12或C(=O)OR13,
W代表O或N-OR15,
G代表氰基甲基、2-氰基乙基、2,2,2-三氟乙基或3,3,3-三氟丙基,
R1代表氢或甲基,
p代表1,
R5a和R5b彼此独立地代表氢、氟、氯、甲基、乙基、甲氧基或乙氧基,
R5c代表氢、氟、氯、溴、氰基、甲氧基或甲氧基羰基,或
代表甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、环丙基或苯基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代且取代基选自氰基、甲氧基、甲氧基羰基和三氟甲基,其中总共存在最多三个上述取代基,
或
R5c代表Y,
Y代表基团Y-2,
Xb代表氟、氯、溴、氰基、甲基、乙基、甲氧基、乙氧基、甲硫基、二氟甲基或三氟甲基,
m代表0或1,
R13和R15彼此独立地代表氢,或
代表C1-C4-烷基、环丙基、环丁基、环戊基、环己基、氧杂环己基或1,1-二氧代硫杂环己基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代且取代基选自氰基、甲基、甲氧基、三氟甲基,或
R13和R15彼此独立地代表环丙基甲基或环丁基甲基,或
代表苯基甲基或吡啶基甲基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,和/或可各自任选地被单取代且取代基选自氰基、甲基、甲氧基、三氟甲基,其中总共存在最多三个上述取代基,
R7a代表氢,
R7b代表C1-C4-烷基、环丙基、苄基或环丙基甲基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯,
或
代表苯基、吡啶基或吡唑基,其中上述基团可任选地被单取代至三取代且取代基彼此独立地选自氟、氯和甲基,和/或可任选地被单取代且取代基选自氰基、甲基、甲氧基、三氟甲基、甲硫基、甲基亚磺酰基和甲基磺酰基,其中总共存在最多三个上述取代基,
并且
R12代表甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基或苯基,其中上述基团可各自任选地被单取代至三取代且取代基彼此独立地选自氟和氯。
5.根据权利要求1至4中任一项所述的化合物,其特征在于,其具有式(I-1)的结构
其中R1、G和T具有权利要求1中给出的含义或权利要求2中给出的含义或权利要求3中给出的含义或权利要求4中给出的含义。
6.根据权利要求1至5中任一项所述的化合物,其特征在于,其具有式(I-1a)的结构
其中R1和T具有权利要求1中给出的含义或权利要求2中给出的含义或权利要求3中给出的含义或权利要求4中给出的含义。
7.根据权利要求1至5中任一项所述的化合物,其特征在于,其具有式(I-1b)的结构
其中R1和T具有权利要求1中给出的含义或权利要求2中给出的含义或权利要求3中给出的含义或权利要求4中给出的含义。
8.式(IV)的化合物
其中结构元素R1、p和G具有权利要求1中给出的含义或权利要求2中给出的含义或权利要求3中给出的含义或权利要求4中给出的含义且Alk代表C1-C4-烷基,优选甲基和乙基且特别优选甲基。
9.式(V)的化合物
其中结构元素R1、p和G具有权利要求1中给出的含义或权利要求2中给出的含义或权利要求3中给出的含义或权利要求4中给出的含义且Y-代表F-、Cl-、Br-、I-、NO3 -、SO4 -、ClO4 -或BF4 -,优选F-、Cl-、Br-、I-或BF4 -且特别优选Br-、Cl-或BF4 -。
10.制剂,特别是农用化学制剂,其包含至少一种权利要求1至7中任一项所述的式(I)的化合物。
11.根据权利要求10所述的制剂,其还包含至少一种增量剂和/或至少一种表面活性物质。
12.根据权利要求10或11所述的制剂,其特征在于,式(I)的化合物与至少一种其他活性化合物混合。
13.一种用于防治害虫、特别是动物害虫的方法,其特征在于,将权利要求1至7中任一项所述的式(I)的化合物或权利要求10至12中任一项所述的制剂作用于害虫和/或其生境。
14.根据权利要求13所述的方法,其特征在于,害虫为动物害虫且其包括昆虫、蛛形纲动物或线虫,或者其特征在于,害虫为昆虫、蛛形纲动物或线虫。
15.权利要求1至7中任一项所述的式(I)的化合物或权利要求10至12中任一项所述的制剂用于防治动物害虫的用途。
16.根据权利要求15所述的用途,其特征在于,动物害虫包括昆虫、蛛形纲动物或线虫,或者其特征在于,动物害虫为昆虫、蛛形纲动物或线虫。
17.根据权利要求15或16所述的用途,用于作物保护。
18.根据权利要求15或16所述的用途,用于动物健康领域。
19.用于保护种子或发芽的植物免受害虫、特别是动物害虫侵害的方法,包括其中将种子与权利要求1至7中任一项所述的式(I)的化合物或权利要求10至12中任一项所述的制剂接触的方法步骤。
20.种子,其通过权利要求19所述的方法获得。
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CN113773319A (zh) * | 2021-09-06 | 2021-12-10 | 贵州大学 | 咪唑并吡啶类介离子衍生物及其制备方法和应用 |
CN113773319B (zh) * | 2021-09-06 | 2023-07-25 | 贵州大学 | 咪唑并吡啶类介离子衍生物及其制备方法和应用 |
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UY37691A (es) | 2018-11-30 |
KR20190141194A (ko) | 2019-12-23 |
US20200146292A1 (en) | 2020-05-14 |
BR112019021803A2 (pt) | 2020-05-05 |
JP2020517624A (ja) | 2020-06-18 |
WO2018192872A1 (de) | 2018-10-25 |
EP3612530A1 (de) | 2020-02-26 |
US10993439B2 (en) | 2021-05-04 |
AR111413A1 (es) | 2019-07-10 |
TW201904965A (zh) | 2019-02-01 |
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