WO2005118552B1 - Anthranilamide insecticides - Google Patents
Anthranilamide insecticidesInfo
- Publication number
- WO2005118552B1 WO2005118552B1 PCT/US2005/012465 US2005012465W WO2005118552B1 WO 2005118552 B1 WO2005118552 B1 WO 2005118552B1 US 2005012465 W US2005012465 W US 2005012465W WO 2005118552 B1 WO2005118552 B1 WO 2005118552B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- compound
- invertebrate pest
- bacillus thuringiensis
- group
- Prior art date
Links
- 230000000749 insecticidal Effects 0.000 title claims 5
- 239000002917 insecticide Substances 0.000 title claims 3
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical compound NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract 19
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 241000607479 Yersinia pestis Species 0.000 claims abstract 14
- 239000003085 diluting agent Substances 0.000 claims abstract 4
- 239000007788 liquid Substances 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
- 239000011780 sodium chloride Substances 0.000 claims abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 239000007787 solid Substances 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 239000004094 surface-active agent Substances 0.000 claims abstract 2
- -1 2- chloro- 4-fluorophenyl Chemical group 0.000 claims 11
- 239000005660 Abamectin Substances 0.000 claims 4
- 241000193388 Bacillus thuringiensis Species 0.000 claims 4
- 229940097012 Bacillus thuringiensis Drugs 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 239000002158 endotoxin Substances 0.000 claims 3
- 230000000967 entomopathogenic Effects 0.000 claims 3
- 239000007921 spray Substances 0.000 claims 3
- ZDOOQPFIGYHZFV-MSOLQXFVSA-N (2S,4R)-2-ethyl-4-[(4-phenoxyphenoxy)methyl]-1,3-dioxolane Chemical compound O1[C@@H](CC)OC[C@H]1COC(C=C1)=CC=C1OC1=CC=CC=C1 ZDOOQPFIGYHZFV-MSOLQXFVSA-N 0.000 claims 2
- 229950008167 Abamectin Drugs 0.000 claims 2
- 239000005875 Acetamiprid Substances 0.000 claims 2
- WCXDHFDTOYPNIE-RIYZIHGNSA-N Acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 claims 2
- 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 2
- 241000193363 Bacillus thuringiensis serovar aizawai Species 0.000 claims 2
- 241001147758 Bacillus thuringiensis serovar kurstaki Species 0.000 claims 2
- 239000005884 Beta-Cyfluthrin Substances 0.000 claims 2
- 239000005888 Clothianidin Substances 0.000 claims 2
- PGOOBECODWQEAB-UHFFFAOYSA-N Clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 239000005946 Cypermethrin Substances 0.000 claims 2
- 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 2
- 239000005894 Emamectin Substances 0.000 claims 2
- CXEGAUYXQAKHKJ-FYOMLGFFSA-N Emamectin 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](NC)[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 CXEGAUYXQAKHKJ-FYOMLGFFSA-N 0.000 claims 2
- RDYMFSUJUZBWLH-SVWSLYAFSA-N Endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 claims 2
- 239000005895 Esfenvalerate Substances 0.000 claims 2
- FNELVJVBIYMIMC-UHFFFAOYSA-N Ethiprole Chemical compound N1=C(C#N)C(S(=O)CC)=C(N)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl FNELVJVBIYMIMC-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 241000233866 Fungi Species 0.000 claims 2
- 239000005906 Imidacloprid Substances 0.000 claims 2
- YWTYJOPNNQFBPC-UHFFFAOYSA-N Imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims 2
- 239000005907 Indoxacarb Substances 0.000 claims 2
- 239000005916 Methomyl Substances 0.000 claims 2
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N Methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 claims 2
- 239000005917 Methoxyfenozide Substances 0.000 claims 2
- 239000005950 Oxamyl Substances 0.000 claims 2
- 239000005925 Pymetrozine Substances 0.000 claims 2
- 239000005927 Pyriproxyfen Substances 0.000 claims 2
- NHDHVHZZCFYRSB-UHFFFAOYSA-N Pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 claims 2
- JUVIOZPCNVVQFO-HBGVWJBISA-N Rotenone Natural products O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 claims 2
- 239000005930 Spinosad Substances 0.000 claims 2
- 239000005941 Thiamethoxam Substances 0.000 claims 2
- 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 2
- YWSCPYYRJXKUDB-KAKFPZCNSA-N Tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 claims 2
- 239000005942 Triflumuron Substances 0.000 claims 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- JFLRKDZMHNBDQS-GQHNJWLYSA-N XPA88EAP6V Chemical compound C([C@@H](OC(=O)C[C@H]1[C@@H]2C=C[C@@H]3C[C@H](C[C@H]3[C@@H]2C=C1C(=O)[C@@H]1C)O[C@H]2[C@@H]([C@H](OC)[C@@H](OC)[C@H](C)O2)OC)CC)CCC1O[C@H]1CC[C@H](N(C)C)[C@@H](C)O1.C([C@@H](OC(=O)C[C@H]1[C@@H]2C=C(C)[C@@H]3C[C@H](C[C@H]3[C@@H]2C=C1C(=O)[C@@H]1C)O[C@H]2[C@@H]([C@H](OC)[C@@H](OC)[C@H](C)O2)OC)CC)CCC1O[C@H]1CC[C@H](N(C)C)[C@@H](C)O1 JFLRKDZMHNBDQS-GQHNJWLYSA-N 0.000 claims 2
- ZXQYGBMAQZUVMI-BWHPXCRDSA-N [cyano-(3-phenoxyphenyl)methyl] (1S,3S)-3-[(Z)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-BWHPXCRDSA-N 0.000 claims 2
- 229960002587 amitraz Drugs 0.000 claims 2
- 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 2
- 229960001591 cyfluthrin Drugs 0.000 claims 2
- QQODLKZGRKWIFG-UHFFFAOYSA-N cyfluthrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-UHFFFAOYSA-N 0.000 claims 2
- 229960005424 cypermethrin Drugs 0.000 claims 2
- NYPJDWWKZLNGGM-RPWUZVMVSA-N esfenvalerate Chemical compound C=1C([C@@H](C#N)OC(=O)[C@@H](C(C)C)C=2C=CC(Cl)=CC=2)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-RPWUZVMVSA-N 0.000 claims 2
- 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 2
- 238000009472 formulation Methods 0.000 claims 2
- 229940056881 imidacloprid Drugs 0.000 claims 2
- VBCVPMMZEGZULK-NRFANRHFSA-N indoxacarb Chemical compound C([C@@]1(OC2)C(=O)OC)C3=CC(Cl)=CC=C3C1=NN2C(=O)N(C(=O)OC)C1=CC=C(OC(F)(F)F)C=C1 VBCVPMMZEGZULK-NRFANRHFSA-N 0.000 claims 2
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 claims 2
- KZAUOCCYDRDERY-UITAMQMPSA-N methyl (1Z)-2-(dimethylamino)-N-(methylcarbamoyloxy)-2-oxoethanimidothioate Chemical compound CNC(=O)O\N=C(/SC)C(=O)N(C)C KZAUOCCYDRDERY-UITAMQMPSA-N 0.000 claims 2
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 claims 2
- 239000002689 soil Substances 0.000 claims 2
- 229940014213 spinosad Drugs 0.000 claims 2
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 claims 2
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 claims 2
- NFGXHKASABOEEW-UHFFFAOYSA-N (+)-methoprene Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- AGMMRUPNXPWLGF-AATRIKPKSA-N (2,3,5,6-tetrafluoro-4-methylphenyl)methyl 2,2-dimethyl-3-[(E)-prop-1-enyl]cyclopropane-1-carboxylate Chemical compound CC1(C)C(/C=C/C)C1C(=O)OCC1=C(F)C(F)=C(C)C(F)=C1F AGMMRUPNXPWLGF-AATRIKPKSA-N 0.000 claims 1
- RLLPVAHGXHCWKJ-HKUYNNGSSA-N (3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-HKUYNNGSSA-N 0.000 claims 1
- XGWIJUOSCAQSSV-ABAIWWIYSA-N (4R,5R)-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide Chemical compound S([C@@H]([C@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-ABAIWWIYSA-N 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 claims 1
- GDZNYEZGJAFIKA-UHFFFAOYSA-N 1-[5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrazol-3-yl]ethanone Chemical compound NC1=C(S(C)=O)C(C(=O)C)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl GDZNYEZGJAFIKA-UHFFFAOYSA-N 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 239000003148 4 aminobutyric acid receptor blocking agent Substances 0.000 claims 1
- QDFVXXBCJYNKKC-UHFFFAOYSA-N 4-[4-(4-chlorophenyl)-4-cyclopropylbutyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=C(OC=2C=CC=CC=2)C(F)=CC=C1CCCC(C=1C=CC(Cl)=CC=1)C1CC1 QDFVXXBCJYNKKC-UHFFFAOYSA-N 0.000 claims 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N Acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 claims 1
- QGLZXHRNAYXIBU-WEVVVXLNSA-N Aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 claims 1
- 241001425390 Aphis fabae Species 0.000 claims 1
- 241000239290 Araneae Species 0.000 claims 1
- 239000005878 Azadirachtin Substances 0.000 claims 1
- FTNJWQUOZFUQQJ-NDAWSKJSSA-N Azadirachtin 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 1
- CJJOSEISRRTUQB-UHFFFAOYSA-N Azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 claims 1
- 241000894006 Bacteria Species 0.000 claims 1
- 239000005653 Bifenazate Substances 0.000 claims 1
- 239000005874 Bifenthrin Substances 0.000 claims 1
- 241001674044 Blattodea Species 0.000 claims 1
- 239000005885 Buprofezin Substances 0.000 claims 1
- 229950000775 CYROMAZINE Drugs 0.000 claims 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N Carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 claims 1
- CWFOCCVIPCEQCK-UHFFFAOYSA-N Chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 claims 1
- RAPBNVDSDCTNRC-UHFFFAOYSA-N Chlorobenzilate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OCC)C1=CC=C(Cl)C=C1 RAPBNVDSDCTNRC-UHFFFAOYSA-N 0.000 claims 1
- 239000005944 Chlorpyrifos Substances 0.000 claims 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N Chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims 1
- 239000005945 Chlorpyrifos-methyl Substances 0.000 claims 1
- 239000005887 Chromafenozide Substances 0.000 claims 1
- 239000005891 Cyromazine Substances 0.000 claims 1
- LVQDKIWDGQRHTE-UHFFFAOYSA-N Cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 claims 1
- 239000005892 Deltamethrin Substances 0.000 claims 1
- OWZREIFADZCYQD-NSHGMRRFSA-N Deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 claims 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N Diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims 1
- UOAMTSKGCBMZTC-UHFFFAOYSA-N Dicofol Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)(Cl)Cl)(O)C1=CC=C(Cl)C=C1 UOAMTSKGCBMZTC-UHFFFAOYSA-N 0.000 claims 1
- LWLJUMBEZJHXHV-UHFFFAOYSA-N Dienochlor Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C1(Cl)C1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LWLJUMBEZJHXHV-UHFFFAOYSA-N 0.000 claims 1
- 239000005893 Diflubenzuron Substances 0.000 claims 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N Diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 claims 1
- 239000005947 Dimethoate Substances 0.000 claims 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N Dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 claims 1
- YKBZOVFACRVRJN-UHFFFAOYSA-N Dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 claims 1
- 241000255925 Diptera Species 0.000 claims 1
- 239000005897 Etoxazole Substances 0.000 claims 1
- ZCJPOPBZHLUFHF-UHFFFAOYSA-N Fenamiphos Chemical compound CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1 ZCJPOPBZHLUFHF-UHFFFAOYSA-N 0.000 claims 1
- 239000005958 Fenamiphos (aka phenamiphos) Substances 0.000 claims 1
- 239000005656 Fenazaquin Substances 0.000 claims 1
- 239000005898 Fenoxycarb Substances 0.000 claims 1
- HJUFTIJOISQSKQ-UHFFFAOYSA-N Fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 claims 1
- 239000005657 Fenpyroximate Substances 0.000 claims 1
- 239000005899 Fipronil Substances 0.000 claims 1
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N Fipronil 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 1
- 239000005900 Flonicamid Substances 0.000 claims 1
- 239000005661 Hexythiazox Substances 0.000 claims 1
- 241000256602 Isoptera Species 0.000 claims 1
- 241000692235 Lipoptena cervi Species 0.000 claims 1
- 239000005912 Lufenuron Substances 0.000 claims 1
- 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 1
- 239000005949 Malathion Substances 0.000 claims 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N Malathion Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 claims 1
- 239000005956 Metaldehyde Substances 0.000 claims 1
- NNKVPIKMPCQWCG-UHFFFAOYSA-N Methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 claims 1
- MEBQXILRKZHVCX-UHFFFAOYSA-N Methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 claims 1
- 229950003442 Methoprene Drugs 0.000 claims 1
- KVIZNNVXXNFLMU-AATRIKPKSA-N Metofluthrin Chemical compound FC1=C(F)C(COC)=C(F)C(F)=C1COC(=O)C1C(C)(C)C1\C=C\C KVIZNNVXXNFLMU-AATRIKPKSA-N 0.000 claims 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N Monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 claims 1
- YNKFZRGTXAPYFD-UHFFFAOYSA-N N-[[2-chloro-3,5-bis(trifluoromethyl)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1Cl YNKFZRGTXAPYFD-UHFFFAOYSA-N 0.000 claims 1
- 241000392928 Parachromis friedrichsthalii Species 0.000 claims 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N Parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 claims 1
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- IOUNQDKNJZEDEP-UHFFFAOYSA-N Phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 claims 1
- 239000005921 Phosmet Substances 0.000 claims 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N Phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 claims 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N Phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 claims 1
- 239000005923 Pirimicarb Substances 0.000 claims 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N Pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 239000005663 Pyridaben Substances 0.000 claims 1
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- 241000255632 Tabanus atratus Species 0.000 claims 1
- 239000005937 Tebufenozide Substances 0.000 claims 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N Tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 claims 1
- 239000005658 Tebufenpyrad Substances 0.000 claims 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N Tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 claims 1
- 239000005938 Teflubenzuron Substances 0.000 claims 1
- 239000005939 Tefluthrin Substances 0.000 claims 1
- ZFHGXWPMULPQSE-SZGBIDFHSA-N Tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@@H]1C(C)(C)[C@@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-SZGBIDFHSA-N 0.000 claims 1
- XLNZEKHULJKQBA-UHFFFAOYSA-N Terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 claims 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N Tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 claims 1
- 239000005940 Thiacloprid Substances 0.000 claims 1
- HOKKPVIRMVDYPB-UVTDQMKNSA-N Thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 claims 1
- 229940016279 Trichlorfon Drugs 0.000 claims 1
- 241000256856 Vespidae Species 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- 239000005667 attractant Substances 0.000 claims 1
- 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 1
- PRLVTUNWOQKEAI-UHFFFAOYSA-N buprofezin Chemical compound O=C1N(C(C)C)C(=NC(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-UHFFFAOYSA-N 0.000 claims 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims 1
- 235000013877 carbamide Nutrition 0.000 claims 1
- 230000031902 chemoattractant activity Effects 0.000 claims 1
- HRBKVYFZANMGRE-UHFFFAOYSA-N chlorpyrifos-methyl Chemical group COP(=S)(OC)OC1=NC(Cl)=C(Cl)C=C1Cl HRBKVYFZANMGRE-UHFFFAOYSA-N 0.000 claims 1
- HPNSNYBUADCFDR-UHFFFAOYSA-N chromafenozide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3CCCOC3=CC=2)C)C(C)(C)C)=C1 HPNSNYBUADCFDR-UHFFFAOYSA-N 0.000 claims 1
- WCMMILVIRZAPLE-UHFFFAOYSA-M cyhexatin Chemical compound C1CCCCC1[Sn](C1CCCCC1)(O)C1CCCCC1 WCMMILVIRZAPLE-UHFFFAOYSA-M 0.000 claims 1
- 229960002483 decamethrin Drugs 0.000 claims 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims 1
- 229940019503 diflubenzuron Drugs 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 claims 1
- DMYHGDXADUDKCQ-UHFFFAOYSA-N fenazaquin Chemical compound C1=CC(C(C)(C)C)=CC=C1CCOC1=NC=NC2=CC=CC=C12 DMYHGDXADUDKCQ-UHFFFAOYSA-N 0.000 claims 1
- HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 claims 1
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 claims 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 claims 1
- 229940013764 fipronil Drugs 0.000 claims 1
- RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 0.000 claims 1
- GBIHOLCMZGAKNG-CGAIIQECSA-N flucythrinate Chemical compound O=C([C@@H](C(C)C)C=1C=CC(OC(F)F)=CC=1)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 GBIHOLCMZGAKNG-CGAIIQECSA-N 0.000 claims 1
- CNKHSLKYRMDDNQ-UHFFFAOYSA-N halofenozide Chemical compound C=1C=CC=CC=1C(=O)N(C(C)(C)C)NC(=O)C1=CC=C(Cl)C=C1 CNKHSLKYRMDDNQ-UHFFFAOYSA-N 0.000 claims 1
- RGNPBRKPHBKNKX-UHFFFAOYSA-N hexaflumuron Chemical compound C1=C(Cl)C(OC(F)(F)C(F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F RGNPBRKPHBKNKX-UHFFFAOYSA-N 0.000 claims 1
- 239000003906 humectant Substances 0.000 claims 1
- HOQADATXFBOEGG-UHFFFAOYSA-N isofenphos Chemical compound CCOP(=S)(NC(C)C)OC1=CC=CC=C1C(=O)OC(C)C HOQADATXFBOEGG-UHFFFAOYSA-N 0.000 claims 1
- 150000002596 lactones Chemical class 0.000 claims 1
- 239000005910 lambda-Cyhalothrin Substances 0.000 claims 1
- 229960000521 lufenuron Drugs 0.000 claims 1
- 229960000453 malathion Drugs 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229930002897 methoprenes Natural products 0.000 claims 1
- HWGXPHSUTYGITL-GFCCVEGCSA-N methyl 4-[(2R)-6-methyl-4-oxoheptan-2-yl]benzoate Chemical class COC(=O)C1=CC=C([C@H](C)CC(=O)CC(C)C)C=C1 HWGXPHSUTYGITL-GFCCVEGCSA-N 0.000 claims 1
- KBHDSWIXRODKSZ-UHFFFAOYSA-N methyl 5-chloro-2-(trifluoromethylsulfonylamino)benzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1NS(=O)(=O)C(F)(F)F KBHDSWIXRODKSZ-UHFFFAOYSA-N 0.000 claims 1
- 125000006217 methyl sulfide group Chemical group [H]C([H])([H])S* 0.000 claims 1
- 229960001952 metrifonate Drugs 0.000 claims 1
- 230000001537 neural Effects 0.000 claims 1
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical compound C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 0.000 claims 1
- YTYGAJLZOJPJGH-UHFFFAOYSA-N noviflumuron Chemical compound FC1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F YTYGAJLZOJPJGH-UHFFFAOYSA-N 0.000 claims 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 claims 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 claims 1
- 239000003380 propellant Substances 0.000 claims 1
- 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 1
- 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 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 claims 1
- 239000003195 sodium channel blocking agent Substances 0.000 claims 1
- GOLXNESZZPUPJE-UHFFFAOYSA-N spiromesifen Chemical compound CC1=CC(C)=CC(C)=C1C(C(O1)=O)=C(OC(=O)CC(C)(C)C)C11CCCC1 GOLXNESZZPUPJE-UHFFFAOYSA-N 0.000 claims 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 claims 1
- 239000005936 tau-Fluvalinate Substances 0.000 claims 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 claims 1
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 claims 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 claims 1
- 241000701447 unidentified baculovirus Species 0.000 claims 1
- 230000003612 virological Effects 0.000 claims 1
- OMFRMAHOUUJSGP-IRHGGOMRSA-N κ-bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 claims 1
- INISTDXBRIBGOC-XMMISQBUSA-N τ-fluvalinate Chemical compound N([C@H](C(C)C)C(=O)OC(C#N)C=1C=C(OC=2C=CC=CC=2)C=CC=1)C1=CC=C(C(F)(F)F)C=C1Cl INISTDXBRIBGOC-XMMISQBUSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 abstract 2
Abstract
This invention provides compounds of Formula (1), N oxides and suitable salts thereof, wherein R1 is Me, Cl, Br or I; R2 is Cl, Br, I or -CN; R3 is Cl, Br, CF3, OCH2CF3 or OCF2H; R4 is H; or C1-4alkyl, C2-4alkenyl or C2-4alkynyl, each optionally substituted with CN or Sme; and R5 is phenyl substituted with 1 to 3 substituents selected from the group consisting of F, Cl, Br and Me. Also disclosed are methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula (1), an N-oxide thereof or a suitable salt of the compound (e.g., as a composition described herein). This invention also pertains to a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Formula (1), an N-oxide thereof or a suitable salt of the compound and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent.
Claims
1. A compound of Formula 1 , an iV-oxide or a salt thereof
R1 is Me, Cl, Br or I; R2 is -CN;
R3 is Cl, Br, CF3, OCH2CF3 or OCF2H; R4 is H; or C1-C4 alkyl, C2-C4 alkenyl or C2-C4 alkynyl, each optionally substituted with CN or SMe; and R5 is phenyl substituted with 1 to 3 substituents selected from the group consisting of F, Cl, Br and Me.
2. The compound of Claim 1 wherein: R3 is Cl, Br or CF3;
R4 is Me, Et, /-Pr or t-Bu; and
R5 is 2-chlorophenyl, 2-fluorophenyl, 2-bromophenyl, 2,4-dichlorophenyl, 2- chloro- 4-fluorophenyl, 2,6-dichlorophenyl, 2,6-difluorophenyl or 2,4,6- trichlorophenyl.
3. A composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of Claim 1 and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, said composition optionally further comprising an effective amount of at least one additional biologically active compound or agent. 53
4. A composition of Claim 3 wherein at least one additional biologically active compound or agent is selected from insecticides of the group consisting of pyrethroids, carbamates, neonicotinoids, neuronal sodium channel blockers, insecticidal macrocyclic lactones, γ-aminobutyric acid antagonists, insecticidal ureas, juvenile hormone mimics, members of Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, and naturally occurring or genetically modified viral insecticides.
5. The composition of Claim 3 wherein the at least one additional biologically active compound or agent is selected from the group consisting of abamectin, acephate, acetamiprid, acetoprole, amidoflumet, avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, bistrifluron, buprofezin, carbofuran, chlorfenapyr, chlorfiuazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothicarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flucythrinate, tau-fluvalinate, fiufenerim, flufenoxuron, gamma-chalothrin, halofenozide, hexaflumuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, methoxyfenozide, metofluthrin, monocrotophos, methoxyfenozide, novaluron, noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, protrifenbute, pymetrozine, pyridalyl, pyriproxyfen, rotenone, spinosad, spiromesifen, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad, tralomethrin, trichlorfon, triflumuron, aldicarb, fenamiphos, amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpyroximate, hexythiazox, propargite, pyridaben, tebufenpyrad, Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, entomopathogenic virus and entomopathogenic fungi.
6. The composition of Claim 3 wherein the at least one additional biologically active compound or agent is selected from the group consisting of cypermethrin, cyhalothrin, cyfluthrin and beta-cyfluthrin, esfenvalerate, 54
fenvalerate, tralomethrin, fenothicarb, methomyl, oxamyl, thiodicarb, acetamiprid, clothianidin, imidacloprid, thiamethoxam, tbiacloprid, indoxacarb, spinosad, abamectin, avermectin, emamectin, endosulfan, ethiprole, fϊpronil, flufenoxuron, triflumuron, diofenolan, pyriproxyfen, pymetrozine, amitraz, Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis delta endotoxin and entomophagous fungi.
7. A method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Claim 1.
8. A method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a composition of Claim 3.
9. The method of Claim 7 or Claim 8 wherein the invertebrate pest is a cockroach, an ant or a termite which is contacted by the compound by consuming a bait composition comprising the compound.
10. The method of Claim 7 or Claim 8 wherein the invertebrate pest is a mosquito, a black fly, a stable, fly, a deer fly, a horse fly, a wasp, a yellow jacket, a hornet, a tick, a spider, an ant, or a gnat which is contacted by a spray composition comprising the compound dispensed from a spray container.
11. The method of Claim 8 wherein a plant is contacted with the composition applied as a soil drench of a liquid formulation.
12. The composition of Claim 3 in the form of a soil drench liquid formulation.
13. A spray composition, comprising:
(a) a compound of Claim 1; and
(b) a propellant.
14. A bait composition, comprising:
(a) a compound of Claim 1;
(b) one or more food materials; 55
(c) optionally an attractant; and
(d) optionally a humectant.
15. A device for controlling an invertebrate pest, comprising:
(a) the bait composition of Claim 14; and
(b) a housing adapted to receive the bait composition, wherein the housing has at least one opening sized to permit the invertebrate pest to pass through the opening so the invertebrate pest can gain access to the bait composition from a location outside the housing, and wherein the housing is further adapted to be placed in or near a locus of potential or known activity for the invertebrate pest.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP05779580A EP1751112A2 (en) | 2004-04-13 | 2005-04-12 | Anthranilamide insecticides |
| BRPI0509413-5A BRPI0509413A (en) | 2004-04-13 | 2005-04-12 | compound, invertebrate pest control composition, invertebrate pest control methods, spray and bait compositions and invertebrate pest control device |
| AU2005250328A AU2005250328A1 (en) | 2004-04-13 | 2005-04-12 | Anthranilamide insecticides |
| MXPA06011776A MXPA06011776A (en) | 2004-04-13 | 2005-04-12 | Anthranilamide insecticides. |
| JP2007508485A JP2007532661A (en) | 2004-04-13 | 2005-04-12 | Anthranilamide insecticide |
| US10/591,200 US20070184018A1 (en) | 2004-04-13 | 2005-04-12 | Anthranilamide insecticides |
| CA002561369A CA2561369A1 (en) | 2004-04-13 | 2005-04-12 | Anthranilamide insecticides |
| IL177757A IL177757A0 (en) | 2004-04-13 | 2006-08-29 | Anthranilamide insecticides |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56181304P | 2004-04-13 | 2004-04-13 | |
| US60/561,813 | 2004-04-13 |
Publications (3)
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|---|---|
| WO2005118552A2 WO2005118552A2 (en) | 2005-12-15 |
| WO2005118552A3 WO2005118552A3 (en) | 2006-01-26 |
| WO2005118552B1 true WO2005118552B1 (en) | 2006-03-02 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2005/012465 WO2005118552A2 (en) | 2004-04-13 | 2005-04-12 | Anthranilamide insecticides |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20070184018A1 (en) |
| EP (1) | EP1751112A2 (en) |
| JP (1) | JP2007532661A (en) |
| KR (1) | KR20060135881A (en) |
| CN (1) | CN1972915A (en) |
| AR (1) | AR049261A1 (en) |
| AU (1) | AU2005250328A1 (en) |
| BR (1) | BRPI0509413A (en) |
| CA (1) | CA2561369A1 (en) |
| IL (1) | IL177757A0 (en) |
| MX (1) | MXPA06011776A (en) |
| RU (1) | RU2006139953A (en) |
| TW (1) | TW200604180A (en) |
| WO (1) | WO2005118552A2 (en) |
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|---|---|---|---|---|
| DK1599463T3 (en) | 2003-01-28 | 2013-09-02 | Du Pont | Cyano-anthranilamidinsekticider |
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- 2005-04-12 RU RU2006139953/04A patent/RU2006139953A/en not_active Application Discontinuation
- 2005-04-12 EP EP05779580A patent/EP1751112A2/en not_active Withdrawn
- 2005-04-12 KR KR1020067021196A patent/KR20060135881A/en not_active Application Discontinuation
- 2005-04-12 JP JP2007508485A patent/JP2007532661A/en not_active Abandoned
- 2005-04-12 US US10/591,200 patent/US20070184018A1/en not_active Abandoned
- 2005-04-12 WO PCT/US2005/012465 patent/WO2005118552A2/en active Application Filing
- 2005-04-12 MX MXPA06011776A patent/MXPA06011776A/en not_active Application Discontinuation
- 2005-04-12 BR BRPI0509413-5A patent/BRPI0509413A/en not_active IP Right Cessation
- 2005-04-12 AU AU2005250328A patent/AU2005250328A1/en not_active Abandoned
- 2005-04-13 AR ARP050101444A patent/AR049261A1/en unknown
- 2005-04-13 TW TW094111714A patent/TW200604180A/en unknown
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2006
- 2006-08-29 IL IL177757A patent/IL177757A0/en unknown
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