JP2011511080A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2011511080A5 JP2011511080A5 JP2010545938A JP2010545938A JP2011511080A5 JP 2011511080 A5 JP2011511080 A5 JP 2011511080A5 JP 2010545938 A JP2010545938 A JP 2010545938A JP 2010545938 A JP2010545938 A JP 2010545938A JP 2011511080 A5 JP2011511080 A5 JP 2011511080A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- hydroxy
- oxo
- pyrido
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 claims description 107
- 229910052736 halogen Inorganic materials 0.000 claims description 55
- 150000002367 halogens Chemical class 0.000 claims description 55
- -1 C 2 -C 4 haloalkenyl Chemical group 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 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 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 230000000967 entomopathogenic effect Effects 0.000 claims description 6
- 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 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- DVBUIBGJRQBEDP-UHFFFAOYSA-N cyantraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl DVBUIBGJRQBEDP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 3
- 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 3
- LZTIMERBDGGAJD-SNAWJCMRSA-N (2e)-2-(nitromethylidene)-1,3-thiazinane Chemical compound [O-][N+](=O)\C=C1/NCCCS1 LZTIMERBDGGAJD-SNAWJCMRSA-N 0.000 claims description 3
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 claims description 3
- 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
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 claims description 3
- 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 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
- 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 3
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical group 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 3
- 239000005660 Abamectin Substances 0.000 claims description 3
- 239000005875 Acetamiprid Substances 0.000 claims description 3
- 239000005652 Acrinathrin Substances 0.000 claims description 3
- 239000005877 Alpha-Cypermethrin Substances 0.000 claims description 3
- 239000005878 Azadirachtin Substances 0.000 claims description 3
- 239000005884 Beta-Cyfluthrin Substances 0.000 claims description 3
- 239000005874 Bifenthrin Substances 0.000 claims description 3
- 239000005885 Buprofezin Substances 0.000 claims description 3
- 239000005886 Chlorantraniliprole Substances 0.000 claims description 3
- 239000005944 Chlorpyrifos Substances 0.000 claims description 3
- 239000005888 Clothianidin Substances 0.000 claims description 3
- 239000005946 Cypermethrin Substances 0.000 claims description 3
- 239000005891 Cyromazine Substances 0.000 claims description 3
- 239000005892 Deltamethrin Substances 0.000 claims description 3
- 239000005894 Emamectin Substances 0.000 claims description 3
- 239000005895 Esfenvalerate Substances 0.000 claims description 3
- 239000005896 Etofenprox Substances 0.000 claims description 3
- 239000005897 Etoxazole 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
- 239000005899 Fipronil Substances 0.000 claims description 3
- 239000005900 Flonicamid Substances 0.000 claims description 3
- 239000005903 Gamma-cyhalothrin Substances 0.000 claims description 3
- 239000005906 Imidacloprid Substances 0.000 claims description 3
- 239000005907 Indoxacarb Substances 0.000 claims description 3
- 239000005914 Metaflumizone Substances 0.000 claims description 3
- MIFOMMKAVSCNKQ-HWIUFGAZSA-N Metaflumizone Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)N\N=C(C=1C=C(C=CC=1)C(F)(F)F)\CC1=CC=C(C#N)C=C1 MIFOMMKAVSCNKQ-HWIUFGAZSA-N 0.000 claims description 3
- 239000005950 Oxamyl Substances 0.000 claims description 3
- 239000005925 Pymetrozine Substances 0.000 claims description 3
- 239000005663 Pyridaben Substances 0.000 claims description 3
- 239000005926 Pyridalyl Substances 0.000 claims description 3
- 239000005927 Pyriproxyfen Substances 0.000 claims description 3
- 229930001406 Ryanodine Natural products 0.000 claims description 3
- 239000005937 Tebufenozide Substances 0.000 claims description 3
- 239000005940 Thiacloprid Substances 0.000 claims description 3
- 239000005941 Thiamethoxam Substances 0.000 claims description 3
- 239000005942 Triflumuron Substances 0.000 claims description 3
- 241000700605 Viruses Species 0.000 claims description 3
- 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 3
- 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 3
- 229950008167 abamectin Drugs 0.000 claims description 3
- YLFSVIMMRPNPFK-WEQBUNFVSA-N acrinathrin Chemical compound CC1(C)[C@@H](\C=C/C(=O)OC(C(F)(F)F)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YLFSVIMMRPNPFK-WEQBUNFVSA-N 0.000 claims description 3
- 229960002587 amitraz Drugs 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- 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 3
- OMFRMAHOUUJSGP-IRHGGOMRSA-N 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 description 3
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 claims description 3
- 229960005286 carbaryl Drugs 0.000 claims description 3
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims description 3
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 claims description 3
- PSOVNZZNOMJUBI-UHFFFAOYSA-N chlorantraniliprole Chemical compound CNC(=O)C1=CC(Cl)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl PSOVNZZNOMJUBI-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims description 3
- 229960001591 cyfluthrin Drugs 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- 229960005424 cypermethrin Drugs 0.000 claims description 3
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical compound NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 claims description 3
- 229950000775 cyromazine Drugs 0.000 claims description 3
- 229960002483 decamethrin Drugs 0.000 claims description 3
- 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 description 3
- GCKZANITAMOIAR-XWVCPFKXSA-N dsstox_cid_14566 Chemical compound [O-]C(=O)C1=CC=CC=C1.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]([NH2+]C)[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 GCKZANITAMOIAR-XWVCPFKXSA-N 0.000 claims description 3
- 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 description 3
- 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 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
- 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 description 3
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 claims description 3
- 229940013764 fipronil Drugs 0.000 claims description 3
- RLQJEEJISHYWON-UHFFFAOYSA-N flonicamid Chemical compound FC(F)(F)C1=CC=NC=C1C(=O)NCC#N RLQJEEJISHYWON-UHFFFAOYSA-N 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
- 229940056881 imidacloprid Drugs 0.000 claims description 3
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 239000005910 lambda-Cyhalothrin Substances 0.000 claims description 3
- 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 description 3
- 229940079888 nitenpyram Drugs 0.000 claims description 3
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 claims description 3
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 claims description 3
- 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 3
- 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 3
- 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 description 3
- JJSYXNQGLHBRRK-SFEDZAPPSA-N ryanodine Chemical compound O([C@@H]1[C@]([C@@]2([C@]3(O)[C@]45O[C@@]2(O)C[C@]([C@]4(CC[C@H](C)[C@H]5O)O)(C)[C@@]31O)C)(O)C(C)C)C(=O)C1=CC=CN1 JJSYXNQGLHBRRK-SFEDZAPPSA-N 0.000 claims description 3
- 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 description 3
- 229960005199 tetramethrin Drugs 0.000 claims description 3
- 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 3
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 3
- 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 description 3
- 239000005943 zeta-Cypermethrin Substances 0.000 claims description 3
- BSTBFVSCILKZRP-UHFFFAOYSA-O (3e)-3-(2-chloro-1h-pyridin-4-ylidene)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]pyrido[1,2-a]pyrimidin-5-ium-2,4-dione Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=NC(Cl)=C1 BSTBFVSCILKZRP-UHFFFAOYSA-O 0.000 claims description 2
- 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 description 2
- RUKLMINUCFGVDM-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-(2,4,5-trifluorophenyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC(F)=C(F)C=C1F RUKLMINUCFGVDM-UHFFFAOYSA-O 0.000 claims description 2
- PQYIZELLTRXCRL-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-(2-methoxyphenyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound COC1=CC=CC=C1C(C1=O)=C(O)[N+](CC=2SC(Cl)=NC=2)=C2N1C=CC=C2 PQYIZELLTRXCRL-UHFFFAOYSA-O 0.000 claims description 2
- MQXBSJRMPODSMJ-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-(3-methoxyphenyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound COC1=CC=CC(C=2C(N3C=CC=CC3=[N+](CC=3SC(Cl)=NC=3)C=2O)=O)=C1 MQXBSJRMPODSMJ-UHFFFAOYSA-O 0.000 claims description 2
- VQWYQXLNQBMZKD-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-(4-methoxyphenyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound C1=CC(OC)=CC=C1C(C1=O)=C(O)[N+](CC=2SC(Cl)=NC=2)=C2N1C=CC=C2 VQWYQXLNQBMZKD-UHFFFAOYSA-O 0.000 claims description 2
- KAHQXJFLKXEGRC-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-[3-(trifluoromethoxy)phenyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC(OC(F)(F)F)=C1 KAHQXJFLKXEGRC-UHFFFAOYSA-O 0.000 claims description 2
- ZHBZAGWZRBEMIH-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-[3-(trifluoromethyl)phenyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC(C(F)(F)F)=C1 ZHBZAGWZRBEMIH-UHFFFAOYSA-O 0.000 claims description 2
- ZOVGKCUMXKZAQJ-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-phenylpyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC=C1 ZOVGKCUMXKZAQJ-UHFFFAOYSA-O 0.000 claims description 2
- DMSJXEUGUYHPCJ-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-(2,4-difluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=C(F)C=C1F DMSJXEUGUYHPCJ-UHFFFAOYSA-O 0.000 claims description 2
- QULKCWKSYBCPJR-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-(2-fluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC=C1F QULKCWKSYBCPJR-UHFFFAOYSA-O 0.000 claims description 2
- JFZOZWSNRKWWDU-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-(3,5-dimethoxyphenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound COC1=CC(OC)=CC(C=2C(N3C=CC=CC3=[N+](CC=3SC(Cl)=NC=3)C=2O)=O)=C1 JFZOZWSNRKWWDU-UHFFFAOYSA-O 0.000 claims description 2
- TZLYXTCAGBXJPW-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-(4-fluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=C(F)C=C1 TZLYXTCAGBXJPW-UHFFFAOYSA-O 0.000 claims description 2
- MLDSRCJCJNHSDN-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-[2-chloro-5-(trifluoromethoxy)phenyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC(OC(F)(F)F)=CC=C1Cl MLDSRCJCJNHSDN-UHFFFAOYSA-O 0.000 claims description 2
- CGJASXMHKMTBFA-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-[2-fluoro-5-(trifluoromethoxy)phenyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC(OC(F)(F)F)=CC=C1F CGJASXMHKMTBFA-UHFFFAOYSA-O 0.000 claims description 2
- UCRMXMBTULVPLX-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC(C(F)(F)F)=CC=C1F UCRMXMBTULVPLX-UHFFFAOYSA-O 0.000 claims description 2
- ARAWPHGDOMXWMI-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-[4-(trifluoromethyl)-1h-pyridin-2-ylidene]pyrido[1,2-a]pyrimidin-5-ium-2,4-dione Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC(C(F)(F)F)=CC=N1 ARAWPHGDOMXWMI-UHFFFAOYSA-O 0.000 claims description 2
- YJHGWBOIKDYSFY-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-2-hydroxy-3-(3-methoxyphenyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound COC1=CC=CC(C=2C(N3C=CC=CC3=[N+](CC=3C=NC(Cl)=CC=3)C=2O)=O)=C1 YJHGWBOIKDYSFY-UHFFFAOYSA-O 0.000 claims description 2
- VWUUKYCKDVZQAW-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-2-hydroxy-3-[3-(trifluoromethoxy)phenyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=CC(OC(F)(F)F)=C1 VWUUKYCKDVZQAW-UHFFFAOYSA-O 0.000 claims description 2
- BZAUXNJBLQGKNN-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-3-(2,3-difluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=CC(F)=C1F BZAUXNJBLQGKNN-UHFFFAOYSA-O 0.000 claims description 2
- BZCAZTGDNMZJOI-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-3-(2,4-difluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=C(F)C=C1F BZCAZTGDNMZJOI-UHFFFAOYSA-O 0.000 claims description 2
- RNWSCKVLHVIXJF-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-3-(2-fluoro-3-methoxyphenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound COC1=CC=CC(C=2C(N3C=CC=CC3=[N+](CC=3C=NC(Cl)=CC=3)C=2O)=O)=C1F RNWSCKVLHVIXJF-UHFFFAOYSA-O 0.000 claims description 2
- XYHPZXYCDLMYKE-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-3-(4-fluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=C(F)C=C1 XYHPZXYCDLMYKE-UHFFFAOYSA-O 0.000 claims description 2
- KACJNCDXHVZRNT-UHFFFAOYSA-O 1-[(6-chloropyridin-3-yl)methyl]-3-[2-chloro-5-(trifluoromethyl)phenyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC(C(F)(F)F)=CC=C1Cl KACJNCDXHVZRNT-UHFFFAOYSA-O 0.000 claims description 2
- JVOHDMQLZSPJCZ-UHFFFAOYSA-O 1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxy-3-[3-(trifluoromethoxy)phenyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(F)=CC=2)C(O)=C1C1=CC=CC(OC(F)(F)F)=C1 JVOHDMQLZSPJCZ-UHFFFAOYSA-O 0.000 claims description 2
- WSQKZWLUHIELGZ-UHFFFAOYSA-O 1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxy-3-[3-(trifluoromethyl)phenyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(F)=CC=2)C(O)=C1C1=CC=CC(C(F)(F)F)=C1 WSQKZWLUHIELGZ-UHFFFAOYSA-O 0.000 claims description 2
- GYMYCGXHDYFWIQ-UHFFFAOYSA-O 1-[1-(6-chloropyridin-3-yl)ethyl]-3-(4-fluorophenyl)-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound OC1=C(C=2C=CC(F)=CC=2)C(=O)N2C=CC=CC2=[N+]1C(C)C1=CC=C(Cl)N=C1 GYMYCGXHDYFWIQ-UHFFFAOYSA-O 0.000 claims description 2
- CTKOGEHIKCYTAS-UHFFFAOYSA-O 2-[1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-4-oxopyrido[1,2-a]pyrimidin-5-ium-3-yl]benzonitrile Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC=C1C#N CTKOGEHIKCYTAS-UHFFFAOYSA-O 0.000 claims description 2
- LFZNBOSTDJTUBR-UHFFFAOYSA-O 2-hydroxy-1-[(1-methylpyrazol-4-yl)methyl]-3-phenylpyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound C1=NN(C)C=C1C[N+]1=C2C=CC=CN2C(=O)C(C=2C=CC=CC=2)=C1O LFZNBOSTDJTUBR-UHFFFAOYSA-O 0.000 claims description 2
- GCBAYZNVUBXELQ-UHFFFAOYSA-O 2-hydroxy-3-phenyl-1-(1,3-thiazol-5-ylmethyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC=NC=2)C(O)=C1C1=CC=CC=C1 GCBAYZNVUBXELQ-UHFFFAOYSA-O 0.000 claims description 2
- SPFJNWLEGQABKT-UHFFFAOYSA-O 3-(2,4-difluorophenyl)-1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(F)=CC=2)C(O)=C1C1=CC=C(F)C=C1F SPFJNWLEGQABKT-UHFFFAOYSA-O 0.000 claims description 2
- CZGUWQYEUWLNIK-UHFFFAOYSA-O 3-(3,5-dimethoxyphenyl)-1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound COC1=CC(OC)=CC(C=2C(N3C=CC=CC3=[N+](CC=3C=NC(F)=CC=3)C=2O)=O)=C1 CZGUWQYEUWLNIK-UHFFFAOYSA-O 0.000 claims description 2
- JBARDNLYURXCNK-UHFFFAOYSA-O 3-(3-bromophenyl)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC(Br)=C1 JBARDNLYURXCNK-UHFFFAOYSA-O 0.000 claims description 2
- FXFBCLLJLOGYOA-UHFFFAOYSA-O 3-(3-bromophenyl)-1-[(6-chloropyridin-3-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=CC(Br)=C1 FXFBCLLJLOGYOA-UHFFFAOYSA-O 0.000 claims description 2
- ULQAUZNZENQDGX-UHFFFAOYSA-O 3-(3-chlorophenyl)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC(Cl)=C1 ULQAUZNZENQDGX-UHFFFAOYSA-O 0.000 claims description 2
- KLKPSSZTECKZQN-UHFFFAOYSA-O 3-(4-fluorophenyl)-1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(F)=CC=2)C(O)=C1C1=CC=C(F)C=C1 KLKPSSZTECKZQN-UHFFFAOYSA-O 0.000 claims description 2
- PXLXAWRVAPTDFO-UHFFFAOYSA-O 3-(4-fluorophenyl)-2-hydroxy-1-(1,3-thiazol-5-ylmethyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC=NC=2)C(O)=C1C1=CC=C(F)C=C1 PXLXAWRVAPTDFO-UHFFFAOYSA-O 0.000 claims description 2
- NPBQKDOXFICOPN-UHFFFAOYSA-O 3-(4-fluorophenyl)-2-hydroxy-1-[(2-methyl-1,3-thiazol-5-yl)methyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound S1C(C)=NC=C1C[N+]1=C2C=CC=CN2C(=O)C(C=2C=CC(F)=CC=2)=C1O NPBQKDOXFICOPN-UHFFFAOYSA-O 0.000 claims description 2
- LTQJQGJZKDUACB-UHFFFAOYSA-O 3-(5-bromo-2-fluorophenyl)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC(Br)=CC=C1F LTQJQGJZKDUACB-UHFFFAOYSA-O 0.000 claims description 2
- LWTQAFOMJHWZJG-UHFFFAOYSA-O 3-(5-chloro-2-fluorophenyl)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC(Cl)=CC=C1F LWTQAFOMJHWZJG-UHFFFAOYSA-O 0.000 claims description 2
- PEXALFOPMHIWPM-UHFFFAOYSA-O 3-[3-(6-chloropyridin-3-yl)phenyl]-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C(C=1)=CC=CC=1C1=CC=C(Cl)N=C1 PEXALFOPMHIWPM-UHFFFAOYSA-O 0.000 claims description 2
- LHROAAHNGQYHJX-UHFFFAOYSA-O 3-[3-bromo-5-(trifluoromethyl)phenyl]-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC(Br)=CC(C(F)(F)F)=C1 LHROAAHNGQYHJX-UHFFFAOYSA-O 0.000 claims description 2
- WWDLSCBXVBTTDD-UHFFFAOYSA-O 3-fluoro-4-[1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxy-4-oxopyrido[1,2-a]pyrimidin-5-ium-3-yl]benzonitrile Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(F)=CC=2)C(O)=C1C1=CC=C(C#N)C=C1F WWDLSCBXVBTTDD-UHFFFAOYSA-O 0.000 claims description 2
- XJFIKRXIJXAJGH-UHFFFAOYSA-N 5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical group ClC1=CC=C2NC(=O)NC2=N1 XJFIKRXIJXAJGH-UHFFFAOYSA-N 0.000 claims description 2
- 241000193388 Bacillus thuringiensis Species 0.000 claims description 2
- 241000894006 Bacteria Species 0.000 claims description 2
- 239000005653 Bifenazate Substances 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 2
- JFLRKDZMHNBDQS-UCQUSYKYSA-N CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C Chemical compound CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C(=C[C@H]3[C@@H]2CC(=O)O1)C)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C.CC[C@H]1CCC[C@@H]([C@H](C(=O)C2=C[C@H]3[C@@H]4C[C@@H](C[C@H]4C=C[C@H]3C2CC(=O)O1)O[C@H]5[C@@H]([C@@H]([C@H]([C@@H](O5)C)OC)OC)OC)C)O[C@H]6CC[C@@H]([C@H](O6)C)N(C)C JFLRKDZMHNBDQS-UCQUSYKYSA-N 0.000 claims description 2
- 239000005945 Chlorpyrifos-methyl Substances 0.000 claims description 2
- 239000005887 Chromafenozide Substances 0.000 claims description 2
- 239000005893 Diflubenzuron Substances 0.000 claims description 2
- 239000005947 Dimethoate Substances 0.000 claims description 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 description 2
- 241000233866 Fungi Species 0.000 claims description 2
- 239000005912 Lufenuron Substances 0.000 claims description 2
- 239000005949 Malathion Substances 0.000 claims description 2
- 239000005956 Metaldehyde Substances 0.000 claims description 2
- 239000005921 Phosmet Substances 0.000 claims description 2
- 239000005923 Pirimicarb Substances 0.000 claims description 2
- MWMQNVGAHVXSPE-UHFFFAOYSA-N Pyriprole Chemical compound ClC=1C=C(C(F)(F)F)C=C(Cl)C=1N1N=C(C#N)C(SC(F)F)=C1NCC1=CC=CC=N1 MWMQNVGAHVXSPE-UHFFFAOYSA-N 0.000 claims description 2
- 239000005929 Spinetoram Substances 0.000 claims description 2
- GOENIMGKWNZVDA-OAMCMWGQSA-N Spinetoram Chemical compound CO[C@@H]1[C@H](OCC)[C@@H](OC)[C@H](C)O[C@H]1OC1C[C@H]2[C@@H]3C=C4C(=O)[C@H](C)[C@@H](O[C@@H]5O[C@H](C)[C@H](CC5)N(C)C)CCC[C@H](CC)OC(=O)CC4[C@@H]3CC[C@@H]2C1 GOENIMGKWNZVDA-OAMCMWGQSA-N 0.000 claims description 2
- 239000005930 Spinosad Substances 0.000 claims description 2
- 239000005664 Spirodiclofen Substances 0.000 claims description 2
- 239000005931 Spirotetramat Substances 0.000 claims description 2
- 239000005658 Tebufenpyrad Substances 0.000 claims description 2
- 239000005938 Teflubenzuron Substances 0.000 claims description 2
- OOWCJRMYMAMSOH-UHFFFAOYSA-N [2,3,5,6-tetrafluoro-4-(methoxymethyl)phenyl]methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound FC1=C(F)C(COC)=C(F)C(F)=C1COC(=O)C1C(C)(C)C1C=C(C)C OOWCJRMYMAMSOH-UHFFFAOYSA-N 0.000 claims description 2
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 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 description 2
- 229940097012 bacillus thuringiensis Drugs 0.000 claims description 2
- 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 2
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 claims description 2
- UISUNVFOGSJSKD-UHFFFAOYSA-N chlorfluazuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=NC=C(C(F)(F)F)C=C1Cl UISUNVFOGSJSKD-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 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 description 2
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 229940019503 diflubenzuron Drugs 0.000 claims description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 claims description 2
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 claims description 2
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 claims description 2
- GJEREQYJIQASAW-UHFFFAOYSA-N flufenerim Chemical compound CC(F)C1=NC=NC(NCCC=2C=CC(OC(F)(F)F)=CC=2)=C1Cl GJEREQYJIQASAW-UHFFFAOYSA-N 0.000 claims description 2
- 229940014144 folate Drugs 0.000 claims description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 claims description 2
- 235000019152 folic acid Nutrition 0.000 claims description 2
- 239000011724 folic acid Substances 0.000 claims description 2
- 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 description 2
- 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 description 2
- 230000000749 insecticidal effect Effects 0.000 claims description 2
- 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 description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 229960000521 lufenuron Drugs 0.000 claims description 2
- 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 2
- 229960000453 malathion Drugs 0.000 claims description 2
- GKKDCARASOJPNG-UHFFFAOYSA-N metaldehyde Chemical compound CC1OC(C)OC(C)OC(C)O1 GKKDCARASOJPNG-UHFFFAOYSA-N 0.000 claims description 2
- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 claims description 2
- 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 description 2
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 claims description 2
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical group COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 claims description 2
- 229960000490 permethrin Drugs 0.000 claims description 2
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 claims description 2
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 claims description 2
- MIOBBYRMXGNORL-UHFFFAOYSA-N pyrifluquinazon Chemical compound C1C2=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C2N(C(=O)C)C(=O)N1NCC1=CC=CN=C1 MIOBBYRMXGNORL-UHFFFAOYSA-N 0.000 claims description 2
- 229940080817 rotenone Drugs 0.000 claims description 2
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 229940014213 spinosad Drugs 0.000 claims description 2
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 claims description 2
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 9
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- IYMPSZUYLDGPPE-UHFFFAOYSA-O 3-(2-fluorophenyl)-1-[(6-fluoropyridin-3-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(F)=CC=2)C(O)=C1C1=CC=CC=C1F IYMPSZUYLDGPPE-UHFFFAOYSA-O 0.000 claims 1
- SDRXGMVTMGLVCQ-UHFFFAOYSA-O 3-(4-fluorophenyl)-2-hydroxy-1-[(1-methylpyrazol-4-yl)methyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound C1=NN(C)C=C1C[N+]1=C2C=CC=CN2C(=O)C(C=2C=CC(F)=CC=2)=C1O SDRXGMVTMGLVCQ-UHFFFAOYSA-O 0.000 claims 1
- 241000237537 Ensis Species 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000002158 endotoxin Substances 0.000 claims 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- HCMJWOGOISXSDL-UHFFFAOYSA-N (2-isothiocyanato-1-phenylethyl)benzene Chemical compound C=1C=CC=CC=1C(CN=C=S)C1=CC=CC=C1 HCMJWOGOISXSDL-UHFFFAOYSA-N 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000258242 Siphonaptera Species 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- 108700003918 Bacillus Thuringiensis insecticidal crystal Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- ZUVGXYUYJMZUDL-UHFFFAOYSA-O (3e)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-[ethoxy(hydroxy)methylidene]pyrido[1,2-a]pyrimidin-5-ium-2,4-dione Chemical compound C=12C=CC=CN2C(=O)C(C(=O)OCC)=C(O)[N+]=1CC1=CN=C(Cl)S1 ZUVGXYUYJMZUDL-UHFFFAOYSA-O 0.000 description 1
- RTEYXBFCIGPUOL-UHFFFAOYSA-O (3z)-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-[hydroxy(phenyl)methylidene]pyrido[1,2-a]pyrimidin-5-ium-2,4-dione Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C(=O)C1=CC=CC=C1 RTEYXBFCIGPUOL-UHFFFAOYSA-O 0.000 description 1
- CNRDPKIZBSXPGU-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxy-3-[3-[6-(trifluoromethyl)pyridin-3-yl]phenyl]pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C(C=1)=CC=CC=1C1=CC=C(C(F)(F)F)N=C1 CNRDPKIZBSXPGU-UHFFFAOYSA-O 0.000 description 1
- UEEUMOQKQVJZDB-UHFFFAOYSA-O 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-3-[3-(6-fluoropyridin-3-yl)-5-(trifluoromethyl)phenyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C(C=C(C=1)C(F)(F)F)=CC=1C1=CC=C(F)N=C1 UEEUMOQKQVJZDB-UHFFFAOYSA-O 0.000 description 1
- YJAKPNISQSYKBS-UHFFFAOYSA-O 1-[(6-fluoropyridin-3-yl)methyl]-3-[2-fluoro-5-(trifluoromethyl)phenyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2C=NC(F)=CC=2)C(O)=C1C1=CC(C(F)(F)F)=CC=C1F YJAKPNISQSYKBS-UHFFFAOYSA-O 0.000 description 1
- 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 description 1
- SCIIWAIOKOHQHJ-UHFFFAOYSA-O 2-hydroxy-3-phenyl-1-(2,2,2-trifluoroethyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC(F)(F)F)C(O)=C1C1=CC=CC=C1 SCIIWAIOKOHQHJ-UHFFFAOYSA-O 0.000 description 1
- ZHSCAPRFTSCFQP-UHFFFAOYSA-O 3-(2,4-difluorophenyl)-2-hydroxy-1-(2,2,2-trifluoroethyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC(F)(F)F)C(O)=C1C1=CC=C(F)C=C1F ZHSCAPRFTSCFQP-UHFFFAOYSA-O 0.000 description 1
- FLYQYYOWQAUREO-UHFFFAOYSA-O 3-(4-fluorophenyl)-2-hydroxy-1-(2,2,2-trifluoroethyl)pyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC(F)(F)F)C(O)=C1C1=CC=C(F)C=C1 FLYQYYOWQAUREO-UHFFFAOYSA-O 0.000 description 1
- VLBLSCYXSVQECH-UHFFFAOYSA-O 3-[(6-chloropyridin-3-yl)methyl]-5-(4-fluorophenyl)-6-hydroxy-1,2-dimethylpyrimidin-1-ium-4-one Chemical compound OC1=C(C=2C=CC(F)=CC=2)C(=O)[N+](C)=C(C)N1CC1=CC=C(Cl)N=C1 VLBLSCYXSVQECH-UHFFFAOYSA-O 0.000 description 1
- LXKRDVJRYPPVQS-UHFFFAOYSA-O 3-[3-bromo-5-(trifluoromethoxy)phenyl]-1-[(2-chloro-1,3-thiazol-5-yl)methyl]-2-hydroxypyrido[1,2-a]pyrimidin-5-ium-4-one Chemical compound O=C1N2C=CC=CC2=[N+](CC=2SC(Cl)=NC=2)C(O)=C1C1=CC(Br)=CC(OC(F)(F)F)=C1 LXKRDVJRYPPVQS-UHFFFAOYSA-O 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- MKQMUPXIFKCDGW-UHFFFAOYSA-O 8-[(2-chloro-1,3-thiazol-5-yl)methyl]-6-(4-fluorophenyl)-7-hydroxy-[1,3]thiazolo[3,2-a]pyrimidin-8-ium-5-one Chemical compound O=C1[N+]=2C=CSC=2N(CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=C(F)C=C1 MKQMUPXIFKCDGW-UHFFFAOYSA-O 0.000 description 1
- RNMNTVTVMKWENQ-UHFFFAOYSA-O 8-[(2-chloro-1,3-thiazol-5-yl)methyl]-7-hydroxy-6-[3-(trifluoromethoxy)phenyl]-[1,3]thiazolo[3,2-a]pyrimidin-8-ium-5-one Chemical compound O=C1[N+]=2C=CSC=2N(CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC(OC(F)(F)F)=C1 RNMNTVTVMKWENQ-UHFFFAOYSA-O 0.000 description 1
- AYBZKZHUQXJNTH-UHFFFAOYSA-O 8-[(2-chloro-1,3-thiazol-5-yl)methyl]-7-hydroxy-6-phenyl-[1,3]thiazolo[3,2-a]pyrimidin-8-ium-5-one Chemical compound O=C1[N+]=2C=CSC=2N(CC=2SC(Cl)=NC=2)C(O)=C1C1=CC=CC=C1 AYBZKZHUQXJNTH-UHFFFAOYSA-O 0.000 description 1
- WHSFGWZCDWYIDA-UHFFFAOYSA-O 8-[(6-chloropyridin-3-yl)methyl]-6-(4-fluorophenyl)-7-hydroxy-[1,3]thiazolo[3,2-a]pyrimidin-8-ium-5-one Chemical compound O=C1[N+]=2C=CSC=2N(CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=C(F)C=C1 WHSFGWZCDWYIDA-UHFFFAOYSA-O 0.000 description 1
- RGABVQJVFOUTFU-UHFFFAOYSA-O 8-[(6-chloropyridin-3-yl)methyl]-7-hydroxy-6-[3-(trifluoromethoxy)phenyl]-[1,3]thiazolo[3,2-a]pyrimidin-8-ium-5-one Chemical compound O=C1[N+]=2C=CSC=2N(CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=CC(OC(F)(F)F)=C1 RGABVQJVFOUTFU-UHFFFAOYSA-O 0.000 description 1
- PZGOSDPELFEGRN-UHFFFAOYSA-O 8-[(6-chloropyridin-3-yl)methyl]-7-hydroxy-6-phenyl-[1,3]thiazolo[3,2-a]pyrimidin-8-ium-5-one Chemical compound O=C1[N+]=2C=CSC=2N(CC=2C=NC(Cl)=CC=2)C(O)=C1C1=CC=CC=C1 PZGOSDPELFEGRN-UHFFFAOYSA-O 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- 0 C**(C=C*1)C1=* Chemical compound C**(C=C*1)C1=* 0.000 description 1
- 241000258924 Ctenocephalides felis Species 0.000 description 1
- 239000005889 Cyantraniliprole Substances 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 1
- 239000005665 Spiromesifen Substances 0.000 description 1
- XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 239000003096 antiparasitic agent Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229950006824 dieldrin Drugs 0.000 description 1
- DFBKLUNHFCTMDC-PICURKEMSA-N dieldrin Chemical compound C([C@H]1[C@H]2[C@@]3(Cl)C(Cl)=C([C@]([C@H]22)(Cl)C3(Cl)Cl)Cl)[C@H]2[C@@H]2[C@H]1O2 DFBKLUNHFCTMDC-PICURKEMSA-N 0.000 description 1
- NGPMUTDCEIKKFM-UHFFFAOYSA-N dieldrin Natural products CC1=C(Cl)C2(Cl)C3C4CC(C5OC45)C3C1(Cl)C2(Cl)Cl NGPMUTDCEIKKFM-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229940074076 glycerol formal Drugs 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229950003442 methoprene Drugs 0.000 description 1
- 229930002897 methoprene Natural products 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 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 description 1
- 239000006208 topical dosage form Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US6378908P | 2008-02-06 | 2008-02-06 | |
| US61/063,789 | 2008-02-06 | ||
| US4342808P | 2008-04-09 | 2008-04-09 | |
| US61/043,428 | 2008-04-09 | ||
| PCT/US2009/032584 WO2009099929A1 (en) | 2008-02-06 | 2009-01-30 | Mesoionic pesticides |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012143613A Division JP5613726B2 (ja) | 2008-02-06 | 2012-06-27 | メソイオン性有害生物防除剤 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011511080A JP2011511080A (ja) | 2011-04-07 |
| JP2011511080A5 true JP2011511080A5 (enExample) | 2012-03-15 |
| JP5068378B2 JP5068378B2 (ja) | 2012-11-07 |
Family
ID=40524655
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010545938A Active JP5068378B2 (ja) | 2008-02-06 | 2009-01-30 | メソイオン性有害生物防除剤 |
| JP2012143613A Active JP5613726B2 (ja) | 2008-02-06 | 2012-06-27 | メソイオン性有害生物防除剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012143613A Active JP5613726B2 (ja) | 2008-02-06 | 2012-06-27 | メソイオン性有害生物防除剤 |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US8552007B2 (enExample) |
| EP (2) | EP2240454B1 (enExample) |
| JP (2) | JP5068378B2 (enExample) |
| KR (2) | KR101404291B1 (enExample) |
| CN (2) | CN104311554B (enExample) |
| AR (1) | AR071644A1 (enExample) |
| AU (1) | AU2009212715B2 (enExample) |
| BR (1) | BRPI0905936B1 (enExample) |
| CA (1) | CA2713347C (enExample) |
| CL (1) | CL2009000252A1 (enExample) |
| CO (1) | CO6321190A2 (enExample) |
| DK (1) | DK2240454T3 (enExample) |
| EA (2) | EA019955B1 (enExample) |
| ES (1) | ES2416083T3 (enExample) |
| HR (1) | HRP20130501T1 (enExample) |
| IL (2) | IL207087A (enExample) |
| MA (1) | MA32026B1 (enExample) |
| MX (2) | MX2010008532A (enExample) |
| MY (1) | MY153886A (enExample) |
| NZ (2) | NZ598147A (enExample) |
| PH (1) | PH12014500760A1 (enExample) |
| PL (1) | PL2240454T3 (enExample) |
| PT (1) | PT2240454E (enExample) |
| RS (1) | RS52788B (enExample) |
| SI (1) | SI2240454T1 (enExample) |
| TW (2) | TWI468407B (enExample) |
| UY (1) | UY31633A1 (enExample) |
| WO (1) | WO2009099929A1 (enExample) |
| ZA (2) | ZA201005035B (enExample) |
Families Citing this family (135)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI468407B (zh) | 2008-02-06 | 2015-01-11 | Du Pont | 中離子農藥 |
| AU2014201144B2 (en) * | 2008-02-06 | 2015-07-16 | Fmc Corporation | Mesoionic pesticides |
| AU2009309813A1 (en) | 2008-10-30 | 2010-05-06 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral arylpyridone derivatives |
| AU2009331660A1 (en) * | 2008-12-22 | 2011-06-30 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| WO2011017347A2 (en) * | 2009-08-05 | 2011-02-10 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
| UA107804C2 (en) * | 2009-08-05 | 2015-02-25 | Du Pont | Mixtures of pesticides mezoionnyh |
| BR112012002519A2 (pt) * | 2009-08-05 | 2019-09-24 | Du Pont | "pesticidas mesoiônicos" |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| EP2475654B1 (en) * | 2009-09-09 | 2016-12-28 | E. I. du Pont de Nemours and Company | Herbicidal pyrimidone derivatives |
| CN102905525A (zh) * | 2010-04-27 | 2013-01-30 | 先正达参股股份有限公司 | 控制耐新烟碱的蚜虫的方法 |
| MX2013006940A (es) * | 2010-12-27 | 2013-07-22 | Sumitomo Chemical Co | Composicion de control de plagas de artropodos y metodo de control de plagas de artropodos. |
| BR112013016362A2 (pt) * | 2010-12-27 | 2018-06-19 | Sumitomo Chemical Co | composição para controle de pragas artrópodes e método para o controle de pragas artrópodes |
| JP2012149043A (ja) * | 2010-12-27 | 2012-08-09 | Sumitomo Chemical Co Ltd | 有害節足動物防除組成物及び有害節足動物の防除方法 |
| US20130289052A1 (en) * | 2010-12-27 | 2013-10-31 | Sumitomo Chemical Company, Limited | Arthropod pest control composition and method for controlling arthropod pests |
| TWI528899B (zh) * | 2010-12-29 | 2016-04-11 | 杜邦股份有限公司 | 中離子性殺蟲劑 |
| WO2012106495A1 (en) | 2011-02-03 | 2012-08-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
| WO2012136724A1 (en) | 2011-04-06 | 2012-10-11 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
| US20120283100A1 (en) * | 2011-05-06 | 2012-11-08 | Dow Agrosciences Llc | Controlling planthoppers |
| US20120283099A1 (en) * | 2011-05-06 | 2012-11-08 | Dow Agrosciences Llc | Controlling planthoppers |
| CN102246774B (zh) * | 2011-05-17 | 2013-05-15 | 德强生物股份有限公司 | 一种包含杀虫环的杀虫增效组合物 |
| TWI572587B (zh) | 2011-12-15 | 2017-03-01 | 杜邦股份有限公司 | 丙二酸二鹽及用以製備丙二醯基二鹵化物之方法 |
| WO2013144228A1 (en) | 2012-03-29 | 2013-10-03 | Basf Se | Pesticidal methods using heterocyclic compounds and derivatives for combating animal pests |
| JP2017141250A (ja) * | 2012-06-21 | 2017-08-17 | 住友化学株式会社 | 有害節足動物防除組成物及び有害節足動物の防除方法 |
| JP6119362B2 (ja) | 2012-06-21 | 2017-04-26 | 住友化学株式会社 | 有害節足動物防除組成物及び有害節足動物の防除方法 |
| AU2013277462B2 (en) * | 2012-06-21 | 2017-06-29 | Fmc Corporation | Solid forms of a pyrido-pyrimidinium inner salt |
| JP2014024830A (ja) * | 2012-06-21 | 2014-02-06 | Sumitomo Chemical Co Ltd | ウンカ類の防除方法 |
| RU2503666C1 (ru) * | 2012-06-25 | 2014-01-10 | Открытое акционерное общество "Государственный научно-исследовательский институт "Кристалл" (ОАО "ГосНИИ "Кристалл") | Способ получения 2-метилпиримидин-4,6-(3н, 5н)-диона |
| WO2014005982A1 (de) | 2012-07-05 | 2014-01-09 | Bayer Cropscience Ag | Insektizide und fungizide wirkstoffkombinationen |
| EP2684879A1 (en) | 2012-07-09 | 2014-01-15 | Basf Se | Substituted mesoionic compounds for combating animal pests |
| BR112015012705B1 (pt) | 2012-12-13 | 2022-04-19 | Novartis Ag | Derivados de piridona, seu uso, combinação e composição farmacêutica |
| AR096022A1 (es) | 2013-04-11 | 2015-12-02 | Basf Se | Compuestos de pirimidinio sustituido, útiles para combatir plagas de animales |
| BR112015031598B1 (pt) * | 2013-06-17 | 2020-12-08 | Basf Se | compostos substituídos de pirimidínio, composição agrícola, método para a proteção das culturas, método não terapêutico para o combate, controle, prevenção ou proteção, uso dos compostos de fórmula (i) e uso dos compostos |
| UY35772A (es) | 2013-10-14 | 2015-05-29 | Bayer Cropscience Ag | Nuevos compuestos plaguicidas |
| WO2015055554A1 (de) | 2013-10-14 | 2015-04-23 | Bayer Cropscience Ag | Wirkstoff für die saatgut- und bodenbehandlung |
| EP3060557A1 (de) | 2013-10-23 | 2016-08-31 | Bayer CropScience Aktiengesellschaft | Substituierte chinoxalin-derivate als schädlingsbekämpfungsmittel |
| RU2016131792A (ru) | 2014-01-03 | 2018-02-06 | Байер Энимэл Хельс ГмбХ | Новые пиразолил-гетероариламиды в качестве средств для борьбы с вредителями |
| AR099120A1 (es) | 2014-01-20 | 2016-06-29 | Bayer Cropscience Ag | Derivados de quinolina como insecticidas y acaricidas |
| US9815792B2 (en) | 2014-04-02 | 2017-11-14 | Bayer Cropscience Aktiengesellschaft | Method for producing carboxamides |
| AU2015257746B2 (en) | 2014-05-08 | 2018-11-22 | Bayer Cropscience Aktiengesellschaft | Pyrazolopyridine sulfonamides as nematicides |
| JP6615791B2 (ja) | 2014-06-05 | 2019-12-04 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺虫剤としての二環式化合物 |
| WO2016001119A1 (de) | 2014-07-01 | 2016-01-07 | Bayer Cropscience Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
| CN104082333A (zh) * | 2014-07-03 | 2014-10-08 | 广西农喜作物科学有限公司 | 含噻虫胺的杀虫组合物 |
| AU2015289246B2 (en) | 2014-07-15 | 2019-07-25 | Elanco Animal Health Gmbh | Aryl-triazolyl pyridines as pest control agents |
| US10149477B2 (en) | 2014-10-06 | 2018-12-11 | Basf Se | Substituted pyrimidinium compounds for combating animal pests |
| WO2016055096A1 (en) | 2014-10-07 | 2016-04-14 | Bayer Cropscience Ag | Method for treating rice seed |
| CN104397004B (zh) * | 2014-10-23 | 2016-03-30 | 北京燕化永乐生物科技股份有限公司 | 一种杀虫组合物 |
| AR102942A1 (es) | 2014-12-11 | 2017-04-05 | Bayer Cropscience Ag | Derivados de arilsulfuro y arilsulfóxido de cinco miembros c-n-conectados, como plaguicidas |
| EP3081085A1 (en) | 2015-04-14 | 2016-10-19 | Bayer CropScience AG | Method for improving earliness in cotton |
| UY36548A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
| UY36547A (es) | 2015-02-05 | 2016-06-01 | Bayer Cropscience Ag | Derivados heterocíclicos condensados bicíclicos sustituidos por 2-(het)arilo como pesticidas |
| TWI702212B (zh) | 2015-02-09 | 2020-08-21 | 德商拜耳作物科學股份有限公司 | 作為除害劑之經取代的２－硫基咪唑基羧醯胺類 |
| US10202351B2 (en) | 2015-03-10 | 2019-02-12 | Bayer Animal Health Gmbh | Pyrazolyl derivatives as pest control agents |
| BR112017021408B1 (pt) | 2015-04-08 | 2022-05-17 | Bayer Cropscience Aktiengesellschaft | Derivados de heterociclo bicíclico condensado, método para controlar pragas animais, e formulação agroquímica |
| US20180310564A1 (en) * | 2015-04-21 | 2018-11-01 | Nippon Kayaku Kabushiki Kaisha | Mesoionic Compound |
| WO2016174049A1 (en) | 2015-04-30 | 2016-11-03 | Bayer Animal Health Gmbh | Anti-parasitic combinations including halogen-substituted compounds |
| EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
| JP2018516897A (ja) | 2015-05-13 | 2018-06-28 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺虫性アリールピロリジン、これを合成する方法、および動物有害生物を制御するための薬剤としてのその使用 |
| MX2018000292A (es) | 2015-07-06 | 2018-04-20 | Bayer Cropscience Ag | Compuestos heterociclicos como pesticidas. |
| BR112018001251A2 (pt) * | 2015-07-22 | 2018-09-18 | Harvard College | ?métodos e superfície interna ou externa? |
| TW201718514A (zh) | 2015-08-07 | 2017-06-01 | 拜耳作物科學股份有限公司 | 作為殺蟲劑之經２－（雜）芳基取代之稠合雜環衍生物 |
| JP2019500336A (ja) * | 2015-12-03 | 2019-01-10 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 殺虫剤としてのメソイオン性ハロゲン化３−（アセチル）−１−［（１，３−チアゾール−５−イル）メチル］−１Ｈ−イミダゾ［１，２−ａ］ピリジン−４−イウム−２−オレート誘導体及び関連する化合物 |
| WO2017097870A1 (de) * | 2015-12-11 | 2017-06-15 | Bayer Cropscience Aktiengesellschaft | Substituierte malonsäureamide als insektizide |
| EP3210468A1 (de) | 2016-02-26 | 2017-08-30 | Bayer CropScience Aktiengesellschaft | Lösungsmittelfreie formulierungen von niedrig schmelzenden wirkstoffen |
| US10653135B2 (en) | 2016-07-11 | 2020-05-19 | Covestro Llc | Methods for treating seeds with an aqueous composition and seeds treated therewith |
| US10653136B2 (en) | 2016-07-11 | 2020-05-19 | Covestro Llc | Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds |
| US10750750B2 (en) | 2016-07-11 | 2020-08-25 | Covestro Llc | Aqueous compositions for treating seeds, seeds treated therewith, and methods for treating seeds |
| MX2019000512A (es) | 2016-07-12 | 2019-05-02 | Bayer Cropscience Ag | Compuestos biciclicos como plaguicidas. |
| AU2017335450A1 (en) * | 2016-09-28 | 2019-04-11 | Nippon Kayaku Kabushiki Kaisha | Novel mesoionic insecticidal compound |
| WO2018069842A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
| BR112019007468B1 (pt) | 2016-10-14 | 2023-02-14 | Pi Industries Ltd | Derivados da fenilamina 4-substituídos e seu uso para proteger as culturas combatendo microrganismos fitopatogênicos indesejáveis |
| EP3400801A1 (en) | 2017-05-10 | 2018-11-14 | Bayer CropScience Aktiengesellschaft | Plant health effect of purpureocillium lilacinum |
| BR112019012262A2 (pt) * | 2016-12-16 | 2019-12-03 | Bayer Ag | imidazopiridinas mesoiônicas para uso como inseticidas |
| WO2018116072A1 (en) | 2016-12-20 | 2018-06-28 | Pi Industries Ltd. | Heterocyclic compounds |
| WO2018116073A1 (en) | 2016-12-21 | 2018-06-28 | Pi Industries Ltd. | 1, 2, 3-thiadiazole compounds and their use as crop protecting agent |
| WO2018177993A1 (de) | 2017-03-31 | 2018-10-04 | Bayer Cropscience Aktiengesellschaft | Pyrazole zur bekämpfung von arthropoden |
| CN116076518A (zh) | 2017-03-31 | 2023-05-09 | 巴斯夫欧洲公司 | 用于防除动物害虫的嘧啶鎓化合物及其混合物 |
| JP7334118B2 (ja) | 2017-03-31 | 2023-08-28 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 節足動物を防除するための三環式カルボキサミド類 |
| KR20190138831A (ko) | 2017-04-12 | 2019-12-16 | 바이엘 악티엔게젤샤프트 | 살곤충제로서 사용하기 위한 메소이온성 이미다조피리딘 |
| MX2019012468A (es) | 2017-04-20 | 2019-12-11 | Pi Industries Ltd | Nuevos compuestos de fenilamina. |
| JP2020517624A (ja) * | 2017-04-21 | 2020-06-18 | バイエル・アクチエンゲゼルシヤフト | 殺虫剤としてのメソイオン性イミダゾピリジン類 |
| CN110621677B (zh) * | 2017-05-03 | 2022-06-07 | 巴斯夫欧洲公司 | 制备手性2,3-二氢噻唑并[3,2-a]嘧啶-4-鎓化合物的方法 |
| BR112019023474B1 (pt) * | 2017-05-09 | 2023-12-19 | Fmc Corporation | Composto, composição e método para controlar uma praga de invertebrados |
| IL270962B2 (en) | 2017-06-01 | 2023-09-01 | Sumitomo Chemical Co | A heterocyclic compound and a mixture containing it |
| EP3638677A1 (en) * | 2017-06-16 | 2020-04-22 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
| CN110678469B (zh) * | 2017-06-19 | 2023-03-03 | 巴斯夫欧洲公司 | 用于防除动物害虫的取代嘧啶鎓化合物和衍生物 |
| WO2019007891A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide wirkstoffkombinationen |
| WO2019007888A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide wirkstoffkombinationen |
| WO2019007887A1 (de) | 2017-07-06 | 2019-01-10 | Bayer Aktiengesellschaft | Insektizide und fungizide wirkstoffkombinationen |
| WO2019042932A1 (en) * | 2017-08-31 | 2019-03-07 | Basf Se | METHOD FOR CONTROLLING RICE PARASITES IN RICE |
| CN109553615B (zh) * | 2017-09-26 | 2020-09-22 | 沈阳中化农药化工研发有限公司 | 一种嘧啶盐类化合物及其用途 |
| CN111201227B (zh) | 2017-10-13 | 2024-03-15 | 巴斯夫欧洲公司 | 用于防除动物害虫的咪唑烷嘧啶鎓化合物 |
| EP3473103A1 (de) | 2017-10-17 | 2019-04-24 | Bayer AG | Wässrige suspensionskonzentrate auf basis von 2-[(2,4-dichlorphenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinon |
| WO2019086474A1 (en) | 2017-10-31 | 2019-05-09 | Syngenta Participations Ag | Pesticidally active mesoionics heterocyclic compounds |
| WO2019115404A1 (en) | 2017-12-13 | 2019-06-20 | Syngenta Participations Ag | Pesticidally active mesoionic heterocyclic compounds |
| US20200337311A1 (en) | 2017-12-20 | 2020-10-29 | Pi Industries Ltd. | Fluoralkenyl compounds, process for preparation and use thereof |
| EP3733672B1 (en) * | 2017-12-25 | 2023-03-22 | Sumitomo Chemical Company, Limited | Heterocyclic compounds and noxious arthropod control agent containing same |
| WO2019150311A1 (en) | 2018-02-02 | 2019-08-08 | Pi Industries Ltd. | 1-3 dithiol compounds and their use for the protection of crops from phytopathogenic microorganisms |
| AU2019229971B2 (en) * | 2018-03-05 | 2022-07-14 | Corteva Agriscience Llc | Process and intermidiates for the preparation of certain mesoionic pesticides |
| CN110317200B (zh) * | 2018-03-28 | 2020-09-11 | 东莞市东阳光农药研发有限公司 | 嘧啶鎓化合物及其用途 |
| CN110452238B (zh) * | 2018-04-18 | 2020-08-11 | 东莞市东阳光农药研发有限公司 | 嘧啶鎓化合物及其用途 |
| WO2020002189A1 (de) | 2018-06-27 | 2020-01-02 | Bayer Aktiengesellschaft | Wirkstoffkombinationen |
| UY38318A (es) | 2018-07-27 | 2020-02-28 | Bayer Ag | Formulaciones de liberación controlada para agroquímicos |
| CA3107984A1 (en) | 2018-07-31 | 2020-02-06 | Bayer Aktiengesellschaft | Controlled release formulations with lignin for agrochemicals |
| CN109006842A (zh) * | 2018-08-13 | 2018-12-18 | 广东顾地丰生物科技有限公司 | 一种含三氟苯嘧啶和哌虫啶的高效复配农药组合物 |
| AR115984A1 (es) | 2018-08-17 | 2021-03-17 | Pi Industries Ltd | Compuestos de 1,2-ditiolona y sus usos |
| WO2020058010A1 (en) | 2018-09-19 | 2020-03-26 | Basf Se | Pesticidal mixtures comprising a mesoionic compound |
| EP3628158A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Pesticidal mixture comprising a mesoionic compound and a biopesticide |
| EP3628157A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method of controlling insecticide resistant insects and virus transmission to plants |
| EP3628156A1 (en) | 2018-09-28 | 2020-04-01 | Basf Se | Method for controlling pests of sugarcane, citrus, rapeseed, and potato plants |
| CN111153900B (zh) * | 2018-11-07 | 2021-09-28 | 东莞市东阳光农药研发有限公司 | 嘧啶鎓化合物及其制备方法和用途 |
| CN113195491A (zh) | 2018-12-18 | 2021-07-30 | 巴斯夫欧洲公司 | 用于防除动物害虫的取代嘧啶鎓化合物 |
| CN111620867A (zh) * | 2019-02-28 | 2020-09-04 | 东莞市东阳光农药研发有限公司 | 介离子杀虫剂 |
| EP3769623A1 (en) | 2019-07-22 | 2021-01-27 | Basf Se | Mesoionic imidazolium compounds and derivatives for combating animal pests |
| CN113923987B (zh) | 2019-05-29 | 2024-10-01 | 巴斯夫欧洲公司 | 用于防除动物害虫的介离子咪唑鎓化合物和衍生物 |
| CN112442026B (zh) * | 2019-08-27 | 2023-08-08 | 东莞市东阳光农药研发有限公司 | 介离子衍生物及其制备方法和应用 |
| AU2020344949A1 (en) | 2019-09-11 | 2022-03-31 | Fmc Corporation | Highly effective formulations on the basis of 2-((2,4-dichlorphenyl)-methyl)-4,4'-dimethyl-3-isoxazolidinones and preemergence herbicides |
| CN112851665B (zh) * | 2019-11-28 | 2023-08-08 | 东莞市东阳光农药研发有限公司 | 新型介离子化合物及其在农业中的应用 |
| AR121097A1 (es) * | 2020-01-24 | 2022-04-20 | Fmc Corp | Insecticidas mesoiónicos |
| CN113563327B (zh) * | 2020-04-28 | 2024-11-29 | 东莞市东阳光农药研发有限公司 | 新型介离子化合物及其合成与应用 |
| CN111592539B (zh) * | 2020-06-03 | 2022-11-15 | 江西农业大学 | 一种三氟苯嘧啶的制备方法 |
| CN114369090B (zh) * | 2020-10-15 | 2025-11-25 | 东莞市东阳光农药研发有限公司 | 一种介离子化合物及其制备方法和应用 |
| CN116828982A (zh) | 2021-01-28 | 2023-09-29 | 法国特种经营公司 | 具有改进的农用化学品、微量营养素和着色剂保留的用于处理水稻种子的方法 |
| CN114957065A (zh) * | 2021-02-22 | 2022-08-30 | 沈阳化工大学 | 一种丙二酸二硫酯类化合物，其制备方法及用途 |
| CN113651811B (zh) * | 2021-08-12 | 2022-06-07 | 贵州大学 | 一种含异噁唑的吡啶并嘧啶酮类化合物及其制备方法和用途 |
| JP2024540323A (ja) | 2021-11-03 | 2024-10-31 | バイエル、アクチエンゲゼルシャフト | 殺菌性化合物としてのビス（ヘテロ）アリールチオエーテル（チオ）アミド |
| US20250011301A1 (en) | 2021-11-10 | 2025-01-09 | Corteva Agriscience Llc | Processes for the preparation of certain mesoionic pesticides |
| WO2023092050A1 (en) | 2021-11-20 | 2023-05-25 | Bayer Cropscience Lp | Beneficial combinations with recombinant bacillus cells expressing a serine protease |
| EP4441049A1 (en) | 2021-11-30 | 2024-10-09 | Bayer Aktiengesellschaft | Bis(hetero)aryl thioether oxadiazines as fungicidal compounds |
| WO2023110656A1 (en) | 2021-12-15 | 2023-06-22 | Bayer Aktiengesellschaft | Spectroscopic solution for non-destructive quantification of one or more chemical substances in a matrix comprising coating and bulk material in a sample, such as coated seeds, using multivariate data analysis |
| JP2025526908A (ja) | 2022-08-18 | 2025-08-15 | コルテバ アグリサイエンス エルエルシー | ある特定のメソイオン性殺有害生物剤の中間体の調製及び単離プロセス |
| CN118580237A (zh) * | 2023-03-02 | 2024-09-03 | 华南农业大学 | 含β-苯丙烯基的吡啶并[1,2-a]嘧啶酮衍生物及其制备方法和应用 |
| CN117720535B (zh) | 2023-12-13 | 2025-05-13 | 贵州大学 | 一种含1,2,4-噁二唑结构的吡啶并[1, 2-a]嘧啶类介离子衍生物及其制备和用途 |
| CN120441570A (zh) * | 2024-02-08 | 2025-08-08 | 青岛清原化合物有限公司 | 介离子嘧啶鎓类化合物及其应用 |
| CN120774913A (zh) * | 2024-04-09 | 2025-10-14 | 青岛清原化合物有限公司 | 一种介离子嘧啶鎓类化合物及其应用 |
| CN120774912A (zh) * | 2024-04-09 | 2025-10-14 | 青岛清原化合物有限公司 | 一种介离子嘧啶鎓类化合物及其应用 |
Family Cites Families (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1815604A (en) | 1922-10-31 | 1931-07-21 | Winthrop Chem Co | Organic mercury compound |
| US1679404A (en) | 1926-02-04 | 1928-08-07 | Rockwood Sprinkler Co Massachusetts | Constant-alarm device for alarm valves |
| BE392862A (enExample) | 1931-12-08 | |||
| US2891855A (en) | 1954-08-16 | 1959-06-23 | Geigy Ag J R | Compositions and methods for influencing the growth of plants |
| US3235361A (en) | 1962-10-29 | 1966-02-15 | Du Pont | Method for the control of undesirable vegetation |
| US3060084A (en) | 1961-06-09 | 1962-10-23 | Du Pont | Improved homogeneous, readily dispersed, pesticidal concentrate |
| US3299566A (en) | 1964-06-01 | 1967-01-24 | Olin Mathieson | Water soluble film containing agricultural chemicals |
| US3309192A (en) | 1964-12-02 | 1967-03-14 | Du Pont | Method of controlling seedling weed grasses |
| US4144050A (en) | 1969-02-05 | 1979-03-13 | Hoechst Aktiengesellschaft | Micro granules for pesticides and process for their manufacture |
| US3852416A (en) | 1971-05-27 | 1974-12-03 | L Grubb | Tick and flea collar of solid solution plasticized vinylic resin-carbamate insecticide |
| US3950360A (en) | 1972-06-08 | 1976-04-13 | Sankyo Company Limited | Antibiotic substances |
| US3984564A (en) | 1972-06-08 | 1976-10-05 | Sankyo Company Limited | Antibiotic substances B-41, their production and their use as insecticides and acaricides |
| US3920442A (en) | 1972-09-18 | 1975-11-18 | Du Pont | Water-dispersible pesticide aggregates |
| SE434277B (sv) | 1976-04-19 | 1984-07-16 | Merck & Co Inc | Sett att framstella nya antihelmintiskt verkande foreningar genom odling av streptomyces avermitilis |
| US4172714A (en) | 1976-12-20 | 1979-10-30 | E. I. Du Pont De Nemours And Company | Dry compactible, swellable herbicidal compositions and pellets produced therefrom |
| DE2703712A1 (de) * | 1977-01-29 | 1978-08-03 | Bayer Ag | Substituierte pyrimidinon eckige klammer auf (di)-thio eckige klammer zu -phosphor-(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide |
| US4199569A (en) | 1977-10-03 | 1980-04-22 | Merck & Co., Inc. | Selective hydrogenation products of C-076 compounds and derivatives thereof |
| ES488154A0 (es) | 1979-02-05 | 1981-04-16 | Schering Corp | Un procedimiento para la preparacion de un compuesto d-(treo-1-aril-2-acilamido-3-fluor-1-propanol |
| US4224901A (en) | 1979-04-16 | 1980-09-30 | Carey Jr Sam H | Combination inner flea-tick collar and outer protective collar, for animals |
| GB2095558B (en) | 1981-03-30 | 1984-10-24 | Avon Packers Ltd | Formulation of agricultural chemicals |
| US4820695A (en) | 1982-09-13 | 1989-04-11 | Eli Lilly And Company | C-20-dihydro-deoxy-(cyclic amino)-derivatives of macrolide antibiotics |
| DE3246493A1 (de) | 1982-12-16 | 1984-06-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von wasserdispergierbaren granulaten |
| IT1173213B (it) | 1984-02-03 | 1987-06-18 | Zambon Spa | Procedimento per fluorurare alcuni derivati dall'1l-fenil-2-ammino-1,3-propandiolo e loro intermedi |
| US5105009A (en) | 1983-06-02 | 1992-04-14 | Zambon S.P.A. | Intermediates for the preparation of 1-(phenyl)-1-hydroxy-2-amino-3-fluoropropane derivatives |
| US5332835A (en) | 1984-02-03 | 1994-07-26 | Zambon S.P.A. | Process for fluorinating 1-phenyl-2-amino-1,3-propanediol compounds and new oxazoline compounds useful in this process |
| US4582918A (en) | 1984-09-19 | 1986-04-15 | Schering Corporation | Preparation of intermediates for (threo)-1-aryl-2-acylamido-3-fluoro-1-propanols |
| US4973750A (en) | 1984-09-19 | 1990-11-27 | Schering Corporation | Preparation of (threo)-1-aryl-2-acylamido-3-fluoro-1-propanols |
| ES8800986A1 (es) | 1985-07-27 | 1987-12-01 | Pfizer | Un procedimiento para la produccion de un nuevo derivado de avermectina |
| US4916154A (en) | 1986-09-12 | 1990-04-10 | American Cyanamid Company | 23-Imino derivatives of LL-F28249 compounds |
| US5149810A (en) * | 1988-04-22 | 1992-09-22 | Imperial Chemical Industries Plc | Pyrimidine compounds |
| US5180587A (en) | 1988-06-28 | 1993-01-19 | E. I. Du Pont De Nemours And Company | Tablet formulations of pesticides |
| US4876352A (en) | 1988-09-14 | 1989-10-24 | Schering Corporation | Pressurized fluorination of hydroxy alkyl groups |
| US5227494A (en) | 1988-09-14 | 1993-07-13 | Schering Corporation | Process for preparing oxazoline compounds |
| IE63502B1 (en) * | 1989-04-21 | 1995-05-03 | Zeneca Ltd | Aminopyrimidine derivatives useful for treating cardiovascular disorders |
| ES2166919T3 (es) | 1989-08-30 | 2002-05-01 | Kynoch Agrochemicals Proprieta | Preparacion de un dispositivo dosificador. |
| EP0415889A3 (en) * | 1989-09-01 | 1991-08-28 | Ciba-Geigy Ag | Anthelmintic agent |
| EP0430885A3 (en) | 1989-12-01 | 1991-11-06 | Ciba-Geigy Ag | Anthelmintical compounds |
| EP0430883A3 (en) | 1989-12-01 | 1991-11-06 | Ciba-Geigy Ag | Anthelmintical compounds |
| JPH05504964A (ja) | 1990-03-12 | 1993-07-29 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | 熱―活性化結合剤からの水分散性又は水溶性有害生物防除剤顆粒 |
| IL98599A (en) | 1990-06-28 | 1995-06-29 | Merck & Co Inc | Stable salts of 4"-deoxy-4"-epi-methylamino avermectin b1a/b1b and insecticidal compositions containing them |
| EP0480679B1 (en) | 1990-10-11 | 1996-09-18 | Sumitomo Chemical Company Limited | Pesticidal composition |
| HU212617B (en) | 1990-10-25 | 1996-09-30 | Schering Corp | Process for preparating florfenicol and its analogs thereto |
| US5184573A (en) | 1992-02-21 | 1993-02-09 | Stevens Jr John L | Animal collar |
| US5352832A (en) | 1992-12-18 | 1994-10-04 | Schering Corporation | Asymmetric process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline intermediates |
| US5399717A (en) | 1993-09-29 | 1995-03-21 | Merck & Co., Inc. | Glycosidation route to 4"-epi-methylamino-4"-deoxyavermectin B1 |
| US5555848A (en) | 1995-05-17 | 1996-09-17 | Trujillo; Wendy J. | Pet/flea collar |
| US5958888A (en) | 1996-07-02 | 1999-09-28 | Merial, Inc. | Water miscible macrolide solutions |
| US6271255B1 (en) | 1996-07-05 | 2001-08-07 | Biotica Technology Limited | Erythromycins and process for their preparation |
| US5663361A (en) | 1996-08-19 | 1997-09-02 | Schering Corporation | Process for preparing intermediates to florfenicol |
| US6339063B1 (en) | 1997-09-10 | 2002-01-15 | Merck & Co., Inc. | 9a-azalides as veterinary antimicrobial agents |
| JP2003512290A (ja) | 1997-09-10 | 2003-04-02 | メルク エンド カムパニー インコーポレーテッド | 家畜抗菌剤としての８ａ−アザライド |
| AP9801420A0 (en) | 1998-01-02 | 1998-12-31 | Pfizer Prod Inc | Novel macrolides. |
| US6239112B1 (en) | 1998-07-09 | 2001-05-29 | Merial, Inc. | Water miscible macrolide solutions |
| CZ299375B6 (cs) | 1998-11-30 | 2008-07-09 | Nihon Nohyaku Co., Ltd. | Ftalamidové deriváty nebo jejich soli, zemedelsko-zahradnický insekticid je obsahující a jeho použití |
| CA2292359C (en) | 1999-01-28 | 2004-09-28 | Pfizer Products Inc. | Novel azalides and methods of making same |
| AU779748C (en) | 2000-01-27 | 2005-12-08 | Zoetis Services Llc | Azalide antibiotic compositions |
| MY138097A (en) | 2000-03-22 | 2009-04-30 | Du Pont | Insecticidal anthranilamides |
| CN1297564C (zh) | 2001-04-27 | 2007-01-31 | 辉瑞产品公司 | 4″－取代－9－脱氧－9a－氮杂－9a－高红霉素A衍生物的制备方法 |
| MY142967A (en) | 2001-08-13 | 2011-01-31 | Du Pont | Method for controlling particular insect pests by applying anthranilamide compounds |
| TW200724033A (en) | 2001-09-21 | 2007-07-01 | Du Pont | Anthranilamide arthropodicide treatment |
| BR0308289A (pt) | 2002-03-08 | 2005-01-11 | Schering Plough Ltd | Antibióticos do tipo florfenicol |
| MD3864C2 (ro) | 2003-01-28 | 2009-11-30 | E.I. Du Pont De Nemours And Company | Compuşi ai cianoantranilamidei, compoziţii pe baza ei şi procedeu de combatere a dăunătorilor nevertebraţi |
| TWI468407B (zh) * | 2008-02-06 | 2015-01-11 | Du Pont | 中離子農藥 |
| WO2011017347A2 (en) | 2009-08-05 | 2011-02-10 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
| UA107804C2 (en) | 2009-08-05 | 2015-02-25 | Du Pont | Mixtures of pesticides mezoionnyh |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| BR112012002519A2 (pt) | 2009-08-05 | 2019-09-24 | Du Pont | "pesticidas mesoiônicos" |
| TWI528899B (zh) | 2010-12-29 | 2016-04-11 | 杜邦股份有限公司 | 中離子性殺蟲劑 |
| WO2012106495A1 (en) | 2011-02-03 | 2012-08-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
-
2009
- 2009-01-16 TW TW101117322A patent/TWI468407B/zh active
- 2009-01-16 TW TW098101726A patent/TWI401023B/zh active
- 2009-01-30 WO PCT/US2009/032584 patent/WO2009099929A1/en not_active Ceased
- 2009-01-30 HR HRP20130501AT patent/HRP20130501T1/hr unknown
- 2009-01-30 MY MYPI2010003384A patent/MY153886A/en unknown
- 2009-01-30 CN CN201410460827.0A patent/CN104311554B/zh active Active
- 2009-01-30 BR BRPI0905936A patent/BRPI0905936B1/pt active IP Right Grant
- 2009-01-30 RS RS20130222A patent/RS52788B/sr unknown
- 2009-01-30 NZ NZ598147A patent/NZ598147A/en not_active IP Right Cessation
- 2009-01-30 JP JP2010545938A patent/JP5068378B2/ja active Active
- 2009-01-30 NZ NZ586799A patent/NZ586799A/en unknown
- 2009-01-30 KR KR1020107019689A patent/KR101404291B1/ko active Active
- 2009-01-30 ES ES09709044T patent/ES2416083T3/es active Active
- 2009-01-30 PL PL09709044T patent/PL2240454T3/pl unknown
- 2009-01-30 EP EP09709044.3A patent/EP2240454B1/en active Active
- 2009-01-30 MX MX2010008532A patent/MX2010008532A/es active IP Right Grant
- 2009-01-30 EA EA201070926A patent/EA019955B1/ru active IP Right Revival
- 2009-01-30 AU AU2009212715A patent/AU2009212715B2/en not_active Ceased
- 2009-01-30 SI SI200930653T patent/SI2240454T1/sl unknown
- 2009-01-30 EA EA201200715A patent/EA201200715A1/ru unknown
- 2009-01-30 CA CA2713347A patent/CA2713347C/en active Active
- 2009-01-30 MX MX2013013073A patent/MX352783B/es unknown
- 2009-01-30 DK DK09709044.3T patent/DK2240454T3/da active
- 2009-01-30 US US12/866,462 patent/US8552007B2/en active Active
- 2009-01-30 CN CN200980104397.6A patent/CN101939302B/zh active Active
- 2009-01-30 EP EP12192457A patent/EP2559687A1/en not_active Withdrawn
- 2009-01-30 PT PT97090443T patent/PT2240454E/pt unknown
- 2009-01-30 KR KR1020137027699A patent/KR101495468B1/ko active Active
- 2009-02-04 UY UY031633A patent/UY31633A1/es active IP Right Grant
- 2009-02-05 AR ARP090100406A patent/AR071644A1/es active IP Right Grant
- 2009-02-05 CL CL2009000252A patent/CL2009000252A1/es unknown
-
2010
- 2010-07-15 ZA ZA2010/05035A patent/ZA201005035B/en unknown
- 2010-07-16 MA MA33029A patent/MA32026B1/fr unknown
- 2010-07-19 IL IL207087A patent/IL207087A/en active IP Right Grant
- 2010-08-04 CO CO10095278A patent/CO6321190A2/es active IP Right Grant
-
2011
- 2011-07-12 ZA ZA2011/05120A patent/ZA201105120B/en unknown
-
2012
- 2012-06-27 JP JP2012143613A patent/JP5613726B2/ja active Active
-
2013
- 2013-05-02 IL IL226126A patent/IL226126A0/en unknown
- 2013-08-15 US US13/967,629 patent/US9018220B2/en active Active
-
2014
- 2014-04-04 PH PH12014500760A patent/PH12014500760A1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2011511080A5 (enExample) | ||
| JP2014503550A5 (enExample) | ||
| JP2009522282A5 (enExample) | ||
| JP5592894B2 (ja) | 殺真菌性複素環化合物 | |
| JP2013541558A5 (enExample) | ||
| CN103270029B (zh) | 作为农药的杂环化合物 | |
| JP2013501061A5 (enExample) | ||
| JP5535941B2 (ja) | 殺菌性アミド | |
| JP4871289B2 (ja) | 環状アミン化合物および有害生物防除剤 | |
| JP6168055B2 (ja) | 縮合複素環化合物 | |
| JP6237629B2 (ja) | アミド化合物 | |
| WO2010005692A4 (en) | Insecticidal cyclic carbonyl amidines | |
| HRP20140196T1 (hr) | Mezoionski pesticidi | |
| RU2011149314A (ru) | Нематоцидные сульфонамиды | |
| ME02284B (me) | Nematokidalni sulfonamidi | |
| JP2018509416A5 (enExample) | ||
| BR112013000925A2 (pt) | compostos heterocíclicos como pesticidas | |
| KR20120112755A (ko) | 살진균제 복소환 화합물 | |
| JP6380375B2 (ja) | 縮合複素環化合物及びその有害生物防除用途 | |
| JP2013060420A (ja) | 有害生物防除剤 | |
| WO2014002754A1 (ja) | アミド化合物及びその有害生物防除用途 | |
| RU2018125940A (ru) | Замещенные по гетероциклу бициклические азол пестициды | |
| JP2019501966A5 (enExample) | ||
| WO2012050141A1 (ja) | ヘテロ芳香環化合物およびその有害生物防除用途 | |
| WO2012073995A1 (ja) | ヘテロ芳香環化合物およびその有害生物防除用途 |