ES2766853T3 - Pesticidas de azol bicíclico sustituido con heterociclo - Google Patents
Pesticidas de azol bicíclico sustituido con heterociclo Download PDFInfo
- Publication number
- ES2766853T3 ES2766853T3 ES16816148T ES16816148T ES2766853T3 ES 2766853 T3 ES2766853 T3 ES 2766853T3 ES 16816148 T ES16816148 T ES 16816148T ES 16816148 T ES16816148 T ES 16816148T ES 2766853 T3 ES2766853 T3 ES 2766853T3
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- Spain
- Prior art keywords
- alkyl
- cycloalkyl
- substituted
- haloalkyl
- independently selected
- Prior art date
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- 125000000623 heterocyclic group Chemical group 0.000 title description 20
- 239000000575 pesticide Substances 0.000 title description 10
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title description 6
- 125000002619 bicyclic group Chemical group 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 232
- -1 nitro, hydroxy Chemical group 0.000 claims abstract description 153
- 125000001424 substituent group Chemical group 0.000 claims abstract description 68
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 63
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 58
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 57
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 55
- 150000002367 halogens Chemical class 0.000 claims abstract description 54
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 51
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims abstract description 46
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 42
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 21
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 18
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 16
- 125000004429 atom Chemical group 0.000 claims abstract description 15
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000011593 sulfur Substances 0.000 claims abstract description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 9
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 6
- 125000006574 non-aromatic ring group Chemical group 0.000 claims abstract description 6
- 101100240518 Caenorhabditis elegans nhr-12 gene Proteins 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 181
- 241000607479 Yersinia pestis Species 0.000 claims description 115
- 238000000034 method Methods 0.000 claims description 75
- 239000003085 diluting agent Substances 0.000 claims description 34
- 239000007788 liquid Substances 0.000 claims description 34
- 238000011282 treatment Methods 0.000 claims description 34
- 241001465754 Metazoa Species 0.000 claims description 32
- 239000007787 solid Substances 0.000 claims description 28
- 239000004094 surface-active agent Substances 0.000 claims description 26
- 239000003795 chemical substances by application Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 241000700605 Viruses Species 0.000 claims description 14
- 239000005660 Abamectin Substances 0.000 claims description 13
- 241000193388 Bacillus thuringiensis Species 0.000 claims description 12
- 241000894006 Bacteria Species 0.000 claims description 12
- 229940097012 bacillus thuringiensis Drugs 0.000 claims description 12
- 230000000967 entomopathogenic effect Effects 0.000 claims description 10
- 241000233866 Fungi Species 0.000 claims description 9
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound 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 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[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 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 claims description 7
- 229950008167 abamectin Drugs 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 7
- 229960002587 amitraz Drugs 0.000 claims description 7
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 239000005884 Beta-Cyfluthrin Substances 0.000 claims description 6
- 239000005944 Chlorpyrifos Substances 0.000 claims description 6
- 239000005925 Pymetrozine Substances 0.000 claims description 6
- 239000005663 Pyridaben Substances 0.000 claims description 6
- 239000005926 Pyridalyl Substances 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- QQODLKZGRKWIFG-RUTXASTPSA-N [(R)-cyano-(4-fluoro-3-phenoxyphenyl)methyl] (1S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-RUTXASTPSA-N 0.000 claims description 6
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims description 6
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 claims description 6
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 claims description 6
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 claims description 6
- AEHJMNVBLRLZKK-UHFFFAOYSA-N pyridalyl Chemical group N1=CC(C(F)(F)F)=CC=C1OCCCOC1=C(Cl)C=C(OCC=C(Cl)Cl)C=C1Cl AEHJMNVBLRLZKK-UHFFFAOYSA-N 0.000 claims description 6
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 claims description 6
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 claims description 5
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 claims description 5
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 claims description 5
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 claims description 5
- 239000005877 Alpha-Cypermethrin Substances 0.000 claims description 5
- 239000005878 Azadirachtin Substances 0.000 claims description 5
- 239000005946 Cypermethrin Substances 0.000 claims description 5
- 239000005899 Fipronil Substances 0.000 claims description 5
- 239000005901 Flubendiamide Substances 0.000 claims description 5
- WCXDHFDTOYPNIE-UHFFFAOYSA-N acetamiprid Chemical compound N#CN=C(C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-UHFFFAOYSA-N 0.000 claims description 5
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[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 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 claims description 5
- VEHPJKVTJQSSKL-UHFFFAOYSA-N azadirachtin Natural products O1C2(C)C(C3(C=COC3O3)O)CC3C21C1(C)C(O)C(OCC2(OC(C)=O)C(CC3OC(=O)C(C)=CC)OC(C)=O)C2C32COC(C(=O)OC)(O)C12 VEHPJKVTJQSSKL-UHFFFAOYSA-N 0.000 claims description 5
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N azadirachtin A Chemical compound C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C\C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-NDAWSKJSSA-N 0.000 claims description 5
- FTNJWQUOZFUQQJ-IRYYUVNJSA-N azadirachtin A Natural products C([C@@H]([C@]1(C=CO[C@H]1O1)O)[C@]2(C)O3)[C@H]1[C@]23[C@]1(C)[C@H](O)[C@H](OC[C@@]2([C@@H](C[C@@H]3OC(=O)C(\C)=C/C)OC(C)=O)C(=O)OC)[C@@H]2[C@]32CO[C@@](C(=O)OC)(O)[C@@H]12 FTNJWQUOZFUQQJ-IRYYUVNJSA-N 0.000 claims description 5
- YFXPPSKYMBTNAV-UHFFFAOYSA-N bensultap Chemical compound C=1C=CC=CC=1S(=O)(=O)SCC(N(C)C)CSS(=O)(=O)C1=CC=CC=C1 YFXPPSKYMBTNAV-UHFFFAOYSA-N 0.000 claims description 5
- 229960001591 cyfluthrin Drugs 0.000 claims description 5
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 claims description 5
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 5
- 229960005424 cypermethrin Drugs 0.000 claims description 5
- 229940013764 fipronil Drugs 0.000 claims description 5
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 claims description 5
- 239000005910 lambda-Cyhalothrin Substances 0.000 claims description 5
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 claims description 5
- 229960005199 tetramethrin Drugs 0.000 claims description 5
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 claims description 5
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 claims description 5
- IQVNEKKDSLOHHK-FNCQTZNRSA-N (E,E)-hydramethylnon Chemical compound N1CC(C)(C)CNC1=NN=C(/C=C/C=1C=CC(=CC=1)C(F)(F)F)\C=C\C1=CC=C(C(F)(F)F)C=C1 IQVNEKKDSLOHHK-FNCQTZNRSA-N 0.000 claims description 4
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 claims description 4
- PRLVTUNWOQKEAI-UHFFFAOYSA-N 2-(tert-butylimino)-5-phenyl-3-(propan-2-yl)-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C(C)C)C(=NC(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-UHFFFAOYSA-N 0.000 claims description 4
- 239000005903 Gamma-cyhalothrin Substances 0.000 claims description 4
- 239000005950 Oxamyl Substances 0.000 claims description 4
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 claims description 4
- 239000005934 Sulfoxaflor Substances 0.000 claims description 4
- 239000005941 Thiamethoxam Substances 0.000 claims description 4
- KAATUXNTWXVJKI-QPIRBTGLSA-N [(s)-cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-QPIRBTGLSA-N 0.000 claims description 4
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 claims description 4
- 229960005286 carbaryl Drugs 0.000 claims description 4
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims description 4
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 claims description 4
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 claims description 4
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 claims description 4
- ZXQYGBMAQZUVMI-GCMPRSNUSA-N gamma-cyhalothrin Chemical compound CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-GCMPRSNUSA-N 0.000 claims description 4
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- 229930002897 methoprene Natural products 0.000 claims description 4
- 229950003442 methoprene Drugs 0.000 claims description 4
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 claims description 4
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 claims description 4
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 claims description 4
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 claims description 4
- 239000005943 zeta-Cypermethrin Substances 0.000 claims description 4
- PGOOBECODWQEAB-UHFFFAOYSA-N (E)-clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 claims description 3
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 239000005653 Bifenazate Substances 0.000 claims description 3
- 239000005888 Clothianidin Substances 0.000 claims description 3
- 239000005896 Etofenprox Substances 0.000 claims description 3
- HMIBKHHNXANVHR-UHFFFAOYSA-N Fenothiocarb Chemical compound CN(C)C(=O)SCCCCOC1=CC=CC=C1 HMIBKHHNXANVHR-UHFFFAOYSA-N 0.000 claims description 3
- 239000005907 Indoxacarb Substances 0.000 claims description 3
- 239000005912 Lufenuron Substances 0.000 claims description 3
- 239000005916 Methomyl Substances 0.000 claims description 3
- 239000005940 Thiacloprid Substances 0.000 claims description 3
- 239000005942 Triflumuron Substances 0.000 claims description 3
- LRZWFURXIMFONG-HRSIRGMGSA-N afidopyropen Chemical compound C([C@@]1(C)[C@H]2[C@]([C@H]3[C@@H](O)C=4C(=O)OC(=CC=4O[C@]3(C)[C@@H](O)C2)C=2C=NC=CC=2)(C)CC[C@@H]1OC(=O)C1CC1)OC(=O)C1CC1 LRZWFURXIMFONG-HRSIRGMGSA-N 0.000 claims description 3
- VHLKTXFWDRXILV-UHFFFAOYSA-N bifenazate Chemical compound C1=C(NNC(=O)OC(C)C)C(OC)=CC=C1C1=CC=CC=C1 VHLKTXFWDRXILV-UHFFFAOYSA-N 0.000 claims description 3
- YREQHYQNNWYQCJ-UHFFFAOYSA-N etofenprox Chemical compound C1=CC(OCC)=CC=C1C(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 YREQHYQNNWYQCJ-UHFFFAOYSA-N 0.000 claims description 3
- 229950005085 etofenprox Drugs 0.000 claims description 3
- RYLHNOVXKPXDIP-UHFFFAOYSA-N flufenoxuron Chemical compound C=1C=C(NC(=O)NC(=O)C=2C(=CC=CC=2F)F)C(F)=CC=1OC1=CC=C(C(F)(F)F)C=C1Cl RYLHNOVXKPXDIP-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01C—PLANTING; SOWING; FERTILISING
- A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
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- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Soil Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Catching Or Destruction (AREA)
Applications Claiming Priority (2)
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| US201562266844P | 2015-12-14 | 2015-12-14 | |
| PCT/US2016/065577 WO2017106000A1 (en) | 2015-12-14 | 2016-12-08 | Heterocycle-substituted bicyclic azole pesticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2766853T3 true ES2766853T3 (es) | 2020-06-15 |
Family
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|---|---|---|---|
| ES16816148T Active ES2766853T3 (es) | 2015-12-14 | 2016-12-08 | Pesticidas de azol bicíclico sustituido con heterociclo |
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| WO (1) | WO2017106000A1 (enExample) |
| ZA (1) | ZA201803836B (enExample) |
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| ES2778628T3 (es) | 2015-03-12 | 2020-08-11 | Fmc Corp | Pesticidas de azol bicíclico sustituido con heterociclo |
| US10383335B2 (en) | 2015-04-09 | 2019-08-20 | Fmc Corporation | Bicyclic pyrazole pesticides |
| RU2758667C2 (ru) * | 2015-12-14 | 2021-11-01 | Фмк Корпорейшн | Замещенные по гетероциклу бициклические азол пестициды |
| KR102711049B1 (ko) * | 2018-07-14 | 2024-09-27 | 에프엠씨 코포레이션 | 인다졸을 포함하는 살충 혼합물 |
| TW202039420A (zh) * | 2018-11-26 | 2020-11-01 | 美商富曼西公司 | 用於防治無脊椎害蟲的間二醯胺化合物 |
| WO2020242946A1 (en) * | 2019-05-24 | 2020-12-03 | Fmc Corporation | Pyrazole-substituted pyrrolidinones as herbicides |
| TWI873157B (zh) | 2019-07-11 | 2025-02-21 | 美商富曼西公司 | 包含吲唑之殺蟲混合物 |
| CN114287434B (zh) * | 2022-01-14 | 2023-07-21 | 海利尔药业集团股份有限公司 | 一种含fluchlordiniliprole的杀虫组合物 |
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| US3966760A (en) | 1974-05-23 | 1976-06-29 | Morton-Norwich Products, Inc. | 2-Substituted-5,6-dimethoxyindazoles |
| TR199800327T1 (en) | 1995-08-30 | 1998-06-22 | Bayer Aktiengesellschaft | A�ilaminosalisilamidler. |
| NZ528961A (en) | 2001-04-20 | 2005-04-29 | Bayer Cropscience Ag | Novel insecticidal azoles |
| AU2003223012A1 (en) | 2002-04-26 | 2003-11-10 | Pfizer Products Inc. | Pyrimidine-2, 4, 6-trione metallo-proteinase inhibitors |
| TW200406386A (en) * | 2002-06-07 | 2004-05-01 | Novartis Ag | Organic compounds |
| EP2336120B1 (en) | 2007-01-10 | 2014-07-16 | MSD Italia S.r.l. | Combinations containing amide substituted indazoles as poly(adp-ribose)polymerase (parp) inhibitors |
| TWI667347B (zh) | 2010-12-15 | 2019-08-01 | 瑞士商先正達合夥公司 | 大豆品種ｓｙｈｔ０ｈ２及偵測其之組合物及方法 |
| TWI528899B (zh) * | 2010-12-29 | 2016-04-11 | 杜邦股份有限公司 | 中離子性殺蟲劑 |
| TWI652014B (zh) * | 2013-09-13 | 2019-03-01 | 美商艾佛艾姆希公司 | 雜環取代之雙環唑殺蟲劑 |
| TW201601632A (zh) * | 2013-11-20 | 2016-01-16 | 杜邦股份有限公司 | １－芳基－３－烷基吡唑殺蟲劑 |
| BR112017011667B1 (pt) | 2014-12-02 | 2021-07-06 | Bayer Cropscience Aktiengesellschaft | Compostos bicíclicos como agentes de controle de pragas |
| DE202014010286U1 (de) | 2014-12-05 | 2015-05-27 | Beiersdorf Ag | Reinigungszubereitungen enthaltend Aktivkohle |
| CN112679467B (zh) * | 2015-03-11 | 2024-11-01 | Fmc公司 | 杂环取代的二环唑杀有害生物剂 |
| ES2778628T3 (es) | 2015-03-12 | 2020-08-11 | Fmc Corp | Pesticidas de azol bicíclico sustituido con heterociclo |
| RU2758667C2 (ru) * | 2015-12-14 | 2021-11-01 | Фмк Корпорейшн | Замещенные по гетероциклу бициклические азол пестициды |
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2016
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- 2016-12-08 WO PCT/US2016/065577 patent/WO2017106000A1/en not_active Ceased
- 2016-12-08 ES ES16816148T patent/ES2766853T3/es active Active
- 2016-12-08 KR KR1020187019767A patent/KR102750692B1/ko active Active
- 2016-12-08 BR BR112018012010-3A patent/BR112018012010A2/pt not_active Application Discontinuation
- 2016-12-08 MY MYPI2018702194A patent/MY183670A/en unknown
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- 2016-12-08 MX MX2018007102A patent/MX382198B/es unknown
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2018
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- 2018-06-11 PH PH12018501241A patent/PH12018501241A1/en unknown
- 2018-06-12 CL CL2018001561A patent/CL2018001561A1/es unknown
- 2018-06-14 CO CONC2018/0006097A patent/CO2018006097A2/es unknown
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2021
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| KR102750692B1 (ko) | 2025-01-09 |
| PH12018501241A1 (en) | 2019-01-28 |
| JP2019501966A (ja) | 2019-01-24 |
| CN108699031A (zh) | 2018-10-23 |
| RU2758667C2 (ru) | 2021-11-01 |
| CO2018006097A2 (es) | 2018-07-10 |
| IL259790B (en) | 2021-10-31 |
| IL259790A (en) | 2018-07-31 |
| EP3390385B1 (en) | 2019-10-30 |
| JP7257789B2 (ja) | 2023-04-14 |
| US20180362495A1 (en) | 2018-12-20 |
| MY183670A (en) | 2021-03-08 |
| EP3390385A1 (en) | 2018-10-24 |
| US10683276B2 (en) | 2020-06-16 |
| AU2016371496B2 (en) | 2021-01-14 |
| BR112018012010A2 (pt) | 2018-12-04 |
| RU2018125940A3 (enExample) | 2020-04-20 |
| MX2018007102A (es) | 2019-01-31 |
| CA3008131C (en) | 2022-05-10 |
| CN108699031B (zh) | 2021-06-15 |
| UA123319C2 (uk) | 2021-03-17 |
| NZ743157A (en) | 2024-07-05 |
| RU2018125940A (ru) | 2020-01-20 |
| KR20180094031A (ko) | 2018-08-22 |
| CA3008131A1 (en) | 2017-06-22 |
| JP2021178853A (ja) | 2021-11-18 |
| WO2017106000A1 (en) | 2017-06-22 |
| AU2016371496A1 (en) | 2018-06-21 |
| CL2018001561A1 (es) | 2018-08-31 |
| MX382198B (es) | 2025-03-13 |
| ZA201803836B (en) | 2019-09-25 |
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