EA030935B1 - Антипаразитарные и пестицидные изоксазолиновые соединения - Google Patents

Info

Publication number

EA030935B1

EA030935B1 EA201690910A EA201690910A EA030935B1 EA 030935 B1 EA030935 B1 EA 030935B1 EA 201690910 A EA201690910 A EA 201690910A EA 201690910 A EA201690910 A EA 201690910A EA 030935 B1 EA030935 B1 EA 030935B1

Authority

EA

Eurasian Patent Office

Prior art keywords

hydrogen atom

alkyl

atom

haloalkyl

trifluoromethyl

Prior art date

2013-11-01

Links

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• Global Dossier
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• 230000000361 pesticidal effect Effects 0.000 title claims abstract description 19
• 150000002547 isoxazolines Chemical class 0.000 title abstract description 48
• 239000003096 antiparasitic agent Substances 0.000 title description 5
• 230000002141 anti-parasite Effects 0.000 title description 3
• 239000000203 mixture Substances 0.000 claims abstract description 224
• 241001465754 Metazoa Species 0.000 claims abstract description 86
• 206010061217 Infestation Diseases 0.000 claims abstract description 24
• 230000000590 parasiticidal effect Effects 0.000 claims abstract description 18
• 208000030852 Parasitic disease Diseases 0.000 claims abstract description 13
• -1 isoxazoline compound Chemical class 0.000 claims description 226
• 150000001875 compounds Chemical class 0.000 claims description 181
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 180
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 180
• 229910052799 carbon Inorganic materials 0.000 claims description 95
• 125000004432 carbon atom Chemical group C* 0.000 claims description 89
• 239000000460 chlorine Substances 0.000 claims description 87
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
• 229910052731 fluorine Inorganic materials 0.000 claims description 67
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 66
• 229910052801 chlorine Inorganic materials 0.000 claims description 66
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 65
• 239000011737 fluorine Substances 0.000 claims description 65
• 125000005843 halogen group Chemical group 0.000 claims description 59
• 239000012634 fragment Substances 0.000 claims description 55
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 40
• 125000000217 alkyl group Chemical group 0.000 claims description 37
• 239000000463 material Substances 0.000 claims description 33
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
• 239000002904 solvent Substances 0.000 claims description 29
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 25
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 25
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 25
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 24
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 23
• 125000006344 nonafluoro n-butyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 22
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 239000002023 wood Substances 0.000 claims description 16
• 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 15
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 241000607479 Yersinia pestis Species 0.000 claims description 10
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 125000001072 heteroaryl group Chemical group 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 125000004995 haloalkylthio group Chemical group 0.000 claims description 4
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 3
• 239000001257 hydrogen Substances 0.000 claims description 3
• 229910052739 hydrogen Inorganic materials 0.000 claims description 3
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
• 125000004001 thioalkyl group Chemical group 0.000 claims description 2
• 238000000034 method Methods 0.000 abstract description 57
• 238000002360 preparation method Methods 0.000 abstract description 53
• 150000003839 salts Chemical class 0.000 abstract description 38
• 239000000575 pesticide Substances 0.000 abstract description 2
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 195
• 239000000243 solution Substances 0.000 description 184
• 150000001721 carbon Chemical group 0.000 description 77
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 68
• 235000019439 ethyl acetate Nutrition 0.000 description 66
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
• 239000013543 active substance Substances 0.000 description 56
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 53
• 244000045947 parasite Species 0.000 description 47
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
• 239000003921 oil Substances 0.000 description 40
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 39
• 235000019198 oils Nutrition 0.000 description 39
• 239000007787 solid Substances 0.000 description 39
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 38
• 239000004480 active ingredient Substances 0.000 description 38
• 125000001624 naphthyl group Chemical group 0.000 description 38
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 37
• 239000012044 organic layer Substances 0.000 description 33
• 239000002244 precipitate Substances 0.000 description 33
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 32
• 239000003208 petroleum Substances 0.000 description 30
• 241000196324 Embryophyta Species 0.000 description 28
• 239000003480 eluent Substances 0.000 description 28
• 239000003112 inhibitor Substances 0.000 description 27
• 125000001188 haloalkyl group Chemical group 0.000 description 26
• 125000004429 atom Chemical group 0.000 description 25
• 239000000741 silica gel Substances 0.000 description 25
• 229910002027 silica gel Inorganic materials 0.000 description 25
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
• 239000003795 chemical substances by application Substances 0.000 description 24
• 239000004094 surface-active agent Substances 0.000 description 24
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 23
• 238000006243 chemical reaction Methods 0.000 description 23
• 238000011282 treatment Methods 0.000 description 23
• 239000003814 drug Substances 0.000 description 22
• 239000000047 product Substances 0.000 description 22
• 150000002148 esters Chemical class 0.000 description 21
• 238000005481 NMR spectroscopy Methods 0.000 description 20
• 239000000126 substance Substances 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• 241000238886 Parasitiformes Species 0.000 description 17
• 229920001223 polyethylene glycol Polymers 0.000 description 17
• 241000258242 Siphonaptera Species 0.000 description 16
• 239000002253 acid Substances 0.000 description 16
• 235000011187 glycerol Nutrition 0.000 description 16
• 229960005150 glycerol Drugs 0.000 description 16
• 239000000843 powder Substances 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 230000015572 biosynthetic process Effects 0.000 description 15
• 230000003071 parasitic effect Effects 0.000 description 15
• 239000012071 phase Substances 0.000 description 15
• 239000011734 sodium Substances 0.000 description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• 239000008187 granular material Substances 0.000 description 14
• 229910052708 sodium Inorganic materials 0.000 description 14
• 229940083542 sodium Drugs 0.000 description 14
• 239000000725 suspension Substances 0.000 description 14
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 13
• 230000037396 body weight Effects 0.000 description 13
• 239000002270 dispersing agent Substances 0.000 description 13
• 244000078703 ectoparasite Species 0.000 description 13
• 239000000839 emulsion Substances 0.000 description 13
• 208000015181 infectious disease Diseases 0.000 description 13
• 239000003960 organic solvent Substances 0.000 description 13
• 239000005660 Abamectin Substances 0.000 description 12
• 241000282472 Canis lupus familiaris Species 0.000 description 12
• 239000006184 cosolvent Substances 0.000 description 12
• 229940079593 drug Drugs 0.000 description 12
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
• 241000283690 Bos taurus Species 0.000 description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
• 241000255925 Diptera Species 0.000 description 11
• 241000282326 Felis catus Species 0.000 description 11
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
• 238000002425 crystallisation Methods 0.000 description 11
• 230000008025 crystallization Effects 0.000 description 11
• 235000014113 dietary fatty acids Nutrition 0.000 description 11
• 239000000194 fatty acid Substances 0.000 description 11
• 229930195729 fatty acid Natural products 0.000 description 11
• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 235000011152 sodium sulphate Nutrition 0.000 description 11
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 10
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
• 241001481703 Rhipicephalus <genus> Species 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
• 150000004665 fatty acids Chemical class 0.000 description 10
• 239000004530 micro-emulsion Substances 0.000 description 10
• 239000003755 preservative agent Substances 0.000 description 10
• 230000002265 prevention Effects 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
• 230000006378 damage Effects 0.000 description 9
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 9
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• ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 9
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• 235000003599 food sweetener Nutrition 0.000 description 7
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
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• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 7
• RMZNJVQKKNOFMQ-UHFFFAOYSA-N 1-amino-3-(2,2,2-trifluoroethyl)-1,3-diazinan-2-one Chemical compound NN1CCCN(CC(F)(F)F)C1=O RMZNJVQKKNOFMQ-UHFFFAOYSA-N 0.000 description 6
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• 125000005842 heteroatom Chemical group 0.000 description 6
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• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 5
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• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
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• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 5
• 239000004009 herbicide Substances 0.000 description 5
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