RU2712092C2 - Замещенные бензамиды для борьбы с членистоногими - Google Patents

Info

Publication number

RU2712092C2

RU2712092C2 RU2016122094A RU2016122094A RU2712092C2 RU 2712092 C2 RU2712092 C2 RU 2712092C2 RU 2016122094 A RU2016122094 A RU 2016122094A RU 2016122094 A RU2016122094 A RU 2016122094A RU 2712092 C2 RU2712092 C2 RU 2712092C2

Authority

RU

Russia

Prior art keywords

alkyl

halogen

substituted

spp

methyl

Prior art date

2013-11-05

Links

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• 241000238421 Arthropoda Species 0.000 title description 6
• 229940054066 benzamide antipsychotics Drugs 0.000 title 1
• 150000003936 benzamides Chemical class 0.000 title 1
• -1 1-(cyano)-cyclopropyl Chemical group 0.000 claims abstract description 516
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 327
• 150000001875 compounds Chemical class 0.000 claims abstract description 315
• 150000002367 halogens Chemical class 0.000 claims abstract description 146
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 41
• 239000002917 insecticide Substances 0.000 claims abstract description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 98
• 229910052731 fluorine Inorganic materials 0.000 claims description 85
• 239000011737 fluorine Substances 0.000 claims description 77
• 239000000460 chlorine Substances 0.000 claims description 73
• 229910052801 chlorine Inorganic materials 0.000 claims description 72
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 62
• 125000001153 fluoro group Chemical group F* 0.000 claims description 51
• 239000000945 filler Substances 0.000 claims description 7
• 239000004094 surface-active agent Substances 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 abstract description 166
• 239000000126 substance Substances 0.000 abstract description 21
• 230000000694 effects Effects 0.000 abstract description 7
• 229910052739 hydrogen Inorganic materials 0.000 description 123
• 229910052757 nitrogen Inorganic materials 0.000 description 118
• 241000196324 Embryophyta Species 0.000 description 89
• 125000001424 substituent group Chemical group 0.000 description 86
• 125000004093 cyano group Chemical group *C#N 0.000 description 69
• 125000005842 heteroatom Chemical group 0.000 description 68
• 125000004432 carbon atom Chemical group C* 0.000 description 64
• 239000000203 mixture Substances 0.000 description 64
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 63
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 61
• 125000001309 chloro group Chemical group Cl* 0.000 description 53
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 53
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 50
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 48
• 229910052721 tungsten Inorganic materials 0.000 description 42
• 229910052760 oxygen Inorganic materials 0.000 description 41
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 40
• 238000000034 method Methods 0.000 description 40
• 125000001246 bromo group Chemical group Br* 0.000 description 39
• 241001465754 Metazoa Species 0.000 description 37
• 229910052717 sulfur Inorganic materials 0.000 description 36
• 229910052799 carbon Inorganic materials 0.000 description 34
• 125000001963 4 membered heterocyclic group Chemical group 0.000 description 32
• 239000001257 hydrogen Substances 0.000 description 32
• 229910052794 bromium Inorganic materials 0.000 description 31
• 241000607479 Yersinia pestis Species 0.000 description 30
• 239000003112 inhibitor Substances 0.000 description 29
• 150000003839 salts Chemical class 0.000 description 28
• 238000011282 treatment Methods 0.000 description 28
• 150000002431 hydrogen Chemical class 0.000 description 27
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 25
• 125000000217 alkyl group Chemical group 0.000 description 25
• 125000004043 oxo group Chemical group O=* 0.000 description 25
• 239000000575 pesticide Substances 0.000 description 25
• 229920000728 polyester Polymers 0.000 description 25
• 125000002373 5 membered heterocyclic group Chemical group 0.000 description 24
• 125000004070 6 membered heterocyclic group Chemical group 0.000 description 24
• 239000004202 carbamide Chemical group 0.000 description 24
• 235000013877 carbamide Nutrition 0.000 description 24
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 23
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 22
• 241001533286 Chrysoma Species 0.000 description 22
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 22
• 125000004122 cyclic group Chemical group 0.000 description 22
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 description 20
• 125000003118 aryl group Chemical group 0.000 description 20
• 244000078703 ectoparasite Species 0.000 description 20
• 125000000623 heterocyclic group Chemical group 0.000 description 20
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
• 125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 description 17
• 241000255925 Diptera Species 0.000 description 16
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 description 15
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 14
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 14
• 241000238631 Hexapoda Species 0.000 description 14
• 239000000969 carrier Substances 0.000 description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
• 239000000047 product Substances 0.000 description 14
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 13
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 13
• 230000009261 transgenic effect Effects 0.000 description 13
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 12
• 239000000463 material Substances 0.000 description 12
• 108090000623 proteins and genes Proteins 0.000 description 12
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 11
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 11
• 241000193388 Bacillus thuringiensis Species 0.000 description 11
• 241000894006 Bacteria Species 0.000 description 11
• 125000004429 atom Chemical group 0.000 description 11
• 238000000576 coating method Methods 0.000 description 11
• 125000000753 cycloalkyl group Chemical group 0.000 description 11
• 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 11
• 125000005009 perfluoropropyl group Chemical group FC(C(C(F)(F)F)(F)F)(F)* 0.000 description 11
• 241000238876 Acari Species 0.000 description 10
• 125000003545 alkoxy group Chemical group 0.000 description 10
• 125000003277 amino group Chemical group 0.000 description 10
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
• 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 10
• 239000008187 granular material Substances 0.000 description 10
• 238000002156 mixing Methods 0.000 description 10
• 229920006395 saturated elastomer Polymers 0.000 description 10
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 description 9
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• 241000239223 Arachnida Species 0.000 description 9
• 241000244206 Nematoda Species 0.000 description 9
• 241001481703 Rhipicephalus <genus> Species 0.000 description 9
• 230000009471 action Effects 0.000 description 9
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
• 239000002270 dispersing agent Substances 0.000 description 9
• 125000001072 heteroaryl group Chemical group 0.000 description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• 239000000546 pharmaceutical excipient Substances 0.000 description 9
• 239000013598 vector Substances 0.000 description 9
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 8
• 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 8
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 8
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• 240000007594 Oryza sativa Species 0.000 description 8
• 235000007164 Oryza sativa Nutrition 0.000 description 8
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
• 239000011248 coating agent Substances 0.000 description 8
• 239000000975 dye Substances 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 235000019441 ethanol Nutrition 0.000 description 8
• NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 8
• 150000002390 heteroarenes Chemical class 0.000 description 8
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 8
• 235000009566 rice Nutrition 0.000 description 8
• 239000002689 soil Substances 0.000 description 8
• 239000002904 solvent Substances 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 8
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 8
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 7
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 7
• 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 7
• 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 7
• 229920000742 Cotton Polymers 0.000 description 7
• 244000299507 Gossypium hirsutum Species 0.000 description 7
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
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• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 7
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• 230000000895 acaricidal effect Effects 0.000 description 7
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• 125000003636 chemical group Chemical group 0.000 description 7
• 238000006243 chemical reaction Methods 0.000 description 7
• 235000005822 corn Nutrition 0.000 description 7
• 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 7
• 239000003814 drug Substances 0.000 description 7
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• 230000002438 mitochondrial effect Effects 0.000 description 7
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
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• FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 6
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• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 6
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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