JP7399589B2 - pest control agent - Google Patents
pest control agent Download PDFInfo
- Publication number
- JP7399589B2 JP7399589B2 JP2020546030A JP2020546030A JP7399589B2 JP 7399589 B2 JP7399589 B2 JP 7399589B2 JP 2020546030 A JP2020546030 A JP 2020546030A JP 2020546030 A JP2020546030 A JP 2020546030A JP 7399589 B2 JP7399589 B2 JP 7399589B2
- Authority
- JP
- Japan
- Prior art keywords
- halo
- alkyl
- alkylsulfonyl
- alkoxy
- formula
- 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.)
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- 241000607479 Yersinia pestis Species 0.000 title claims description 71
- -1 cyano, nitro, phenyl group Chemical group 0.000 claims description 423
- 125000005843 halogen group Chemical group 0.000 claims description 358
- 150000001875 compounds Chemical class 0.000 claims description 246
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 114
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 102
- 150000003839 salts Chemical class 0.000 claims description 94
- 150000001204 N-oxides Chemical class 0.000 claims description 68
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 58
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 55
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 49
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 38
- 239000003795 chemical substances by application Substances 0.000 claims description 37
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 28
- 241001465754 Metazoa Species 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 239000004480 active ingredient Substances 0.000 claims description 18
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 15
- 108090000623 proteins and genes Proteins 0.000 claims description 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 102000004169 proteins and genes Human genes 0.000 claims description 13
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 12
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 11
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 10
- 229910052770 Uranium Inorganic materials 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 10
- 230000000749 insecticidal effect Effects 0.000 claims description 10
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 10
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 10
- 230000003071 parasitic effect Effects 0.000 claims description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 230000000967 entomopathogenic effect Effects 0.000 claims description 9
- 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
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 8
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 8
- XLNZEKHULJKQBA-UHFFFAOYSA-N terbufos Chemical compound CCOP(=S)(OCC)SCSC(C)(C)C XLNZEKHULJKQBA-UHFFFAOYSA-N 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000005412 pyrazyl group Chemical group 0.000 claims description 7
- 125000005495 pyridazyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- ZCVAOQKBXKSDMS-PVAVHDDUSA-N (+)-trans-(S)-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-PVAVHDDUSA-N 0.000 claims description 6
- 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 6
- ZFHGXWPMULPQSE-UKSCLKOJSA-N (Z)-(1R)-cis-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-UKSCLKOJSA-N 0.000 claims description 6
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 6
- 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 6
- XFDJMIHUAHSGKG-UHFFFAOYSA-N chlorethoxyfos Chemical compound CCOP(=S)(OCC)OC(Cl)C(Cl)(Cl)Cl XFDJMIHUAHSGKG-UHFFFAOYSA-N 0.000 claims description 6
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims description 6
- 239000010949 copper Substances 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 6
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims description 6
- 229960005199 tetramethrin Drugs 0.000 claims description 6
- 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 6
- 229960002447 thiram Drugs 0.000 claims description 6
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 claims description 6
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 claims description 5
- DSKJPMWIHSOYEA-UHFFFAOYSA-N bupirimate Chemical compound CCCCC1=C(C)N=C(NCC)N=C1OS(=O)(=O)N(C)C DSKJPMWIHSOYEA-UHFFFAOYSA-N 0.000 claims description 5
- 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 description 5
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 claims description 4
- ONILAONOGQYBHW-UHFFFAOYSA-N 5-bromo-n-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-2-(3,5-dichloropyridin-2-yl)pyrazole-3-carboxamide Chemical compound CNC(=O)C1=CC(Cl)=CC(Cl)=C1NC(=O)C1=CC(Br)=NN1C1=NC=C(Cl)C=C1Cl ONILAONOGQYBHW-UHFFFAOYSA-N 0.000 claims description 4
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 239000005762 Dimoxystrobin Substances 0.000 claims description 4
- HMIBKHHNXANVHR-UHFFFAOYSA-N Fenothiocarb Chemical compound CN(C)C(=O)SCCCCOC1=CC=CC=C1 HMIBKHHNXANVHR-UHFFFAOYSA-N 0.000 claims description 4
- 239000005783 Fluopyram Substances 0.000 claims description 4
- 239000005903 Gamma-cyhalothrin Substances 0.000 claims description 4
- YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 claims description 4
- 239000005820 Prochloraz Substances 0.000 claims description 4
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- ZCVAOQKBXKSDMS-UHFFFAOYSA-N allethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-UHFFFAOYSA-N 0.000 claims description 4
- CJPQIRJHIZUAQP-MRXNPFEDSA-N benalaxyl-M Chemical compound CC=1C=CC=C(C)C=1N([C@H](C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-MRXNPFEDSA-N 0.000 claims description 4
- 229960005286 carbaryl Drugs 0.000 claims description 4
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims description 4
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims description 4
- WXUZAHCNPWONDH-DYTRJAOYSA-N dimoxystrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC(C)=CC=C1C WXUZAHCNPWONDH-DYTRJAOYSA-N 0.000 claims description 4
- DOFZAZXDOSGAJZ-UHFFFAOYSA-N disulfoton Chemical compound CCOP(=S)(OCC)SCCSCC DOFZAZXDOSGAJZ-UHFFFAOYSA-N 0.000 claims description 4
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 claims description 4
- MBHXIQDIVCJZTD-RVDMUPIBSA-N flufenoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=C(C(F)(F)F)C=C1Cl MBHXIQDIVCJZTD-RVDMUPIBSA-N 0.000 claims description 4
- KVDJTXBXMWJJEF-UHFFFAOYSA-N fluopyram Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CCNC(=O)C1=CC=CC=C1C(F)(F)F KVDJTXBXMWJJEF-UHFFFAOYSA-N 0.000 claims description 4
- ZXQYGBMAQZUVMI-GCMPRSNUSA-N gamma-cyhalothrin Chemical compound CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-GCMPRSNUSA-N 0.000 claims description 4
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 claims description 4
- SDMSCIWHRZJSRN-UHFFFAOYSA-N isoxathion Chemical compound O1N=C(OP(=S)(OCC)OCC)C=C1C1=CC=CC=C1 SDMSCIWHRZJSRN-UHFFFAOYSA-N 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 claims description 4
- YRRBXJLFCBCKNW-UHFFFAOYSA-N prothiocarb Chemical compound CCSC(=O)NCCCN(C)C YRRBXJLFCBCKNW-UHFFFAOYSA-N 0.000 claims description 4
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 claims description 4
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 claims description 4
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 claims description 4
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 claims description 4
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 claims description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 3
- 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
- YNWVFADWVLCOPU-MDWZMJQESA-N (1E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MDWZMJQESA-N 0.000 claims description 3
- KAATUXNTWXVJKI-GGPKGHCWSA-N (1R)-trans-(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-GGPKGHCWSA-N 0.000 claims description 3
- FJDPATXIBIBRIM-QFMSAKRMSA-N (1R)-trans-cyphenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 FJDPATXIBIBRIM-QFMSAKRMSA-N 0.000 claims description 3
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 claims description 3
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 claims description 3
- 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 description 3
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 claims description 3
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 claims description 3
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-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
- CXNPLSGKWMLZPZ-GIFSMMMISA-N (2r,3r,6s)-3-[[(3s)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid Chemical compound O1[C@@H](C(O)=O)[C@H](NC(=O)C[C@@H](N)CCN(C)C(N)=N)C=C[C@H]1N1C(=O)N=C(N)C=C1 CXNPLSGKWMLZPZ-GIFSMMMISA-N 0.000 claims description 3
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 claims description 3
- PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-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
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- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- DBHVHTPMRCXCIY-UHFFFAOYSA-N tyclopyrazoflor Chemical compound N1=C(Cl)C(N(C(=O)CCSCCC(F)(F)F)CC)=CN1C1=CC=CN=C1 DBHVHTPMRCXCIY-UHFFFAOYSA-N 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01C—PLANTING; SOWING; FERTILISING
- A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
- A01C1/06—Coating or dressing seed
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Environmental Sciences (AREA)
- Public Health (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Soil Sciences (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、式(1)、式(2)、式(3)で表される化合物若しくはその塩又はそれらのN-オキシドおよびそれを有効成分として含んでなる有害生物防除剤に関する。 The present invention relates to a compound represented by formula (1), formula (2), or formula (3), a salt thereof, or an N-oxide thereof, and a pest control agent comprising the same as an active ingredient.
これまでに有害節足動物の防除を目的として、様々な化合物が検討されており、実用に供されている。例えば、特許文献1、2には、縮合複素環化合物が害虫防除剤として開示されている。また、特許文献3、特許文献4には、2-(ピリジン-2-イル)-[1,2,4]トリアゾロ[1,5-a]ピリジンを含む請求項の記載がなされているが、実際には合成されておらず、また、特許文献5には、一定の[1,2,4]トリアゾロ[1,5-a]ピリジン環を有する化合物が害虫防除剤として開示されている。また、特許文献6には、一定のアミド化合物が開示されている。しかしながら、高い有害生物防除活性を有し、実用性の高い化合物は見出されていない。 Various compounds have been studied and put into practical use for the purpose of controlling harmful arthropods. For example, Patent Documents 1 and 2 disclose fused heterocyclic compounds as pest control agents. Further, Patent Document 3 and Patent Document 4 include claims containing 2-(pyridin-2-yl)-[1,2,4]triazolo[1,5-a]pyridine, It has not actually been synthesized, and Patent Document 5 discloses a compound having a certain [1,2,4]triazolo[1,5-a]pyridine ring as an insect control agent. Additionally, Patent Document 6 discloses certain amide compounds. However, a compound with high pest control activity and high practicality has not been found.
本発明は、種々の有害生物に対して優れた防除活性を示す新規化合物およびそれを有効成分として含んでなる有害生物防除剤を提供することを課題とする。 An object of the present invention is to provide a novel compound that exhibits excellent control activity against various pests, and a pest control agent containing the compound as an active ingredient.
本発明者らは鋭意研究を重ねた結果、式(1)又は式(2)又は式(3)で表される化合物が、高い有害生物防除活性を有することを見い出し、本発明を完成させるに至った。 As a result of intensive research, the present inventors discovered that the compound represented by formula (1), formula (2), or formula (3) has high pest control activity, and it was necessary to complete the present invention. It's arrived.
すなわち、本発明は以下に関するが、それに限定されない。
<1>
式(1)又は式(2)又は式(3)で表される化合物若しくはその塩又はそれらのN-オキシド。
[式(1)、式(2)及び式(3)中、
G1は、G1-1、G1-2、G1-3、G1-4又はG1-5で表される構造を表し、
G2は、G2-1、G2-2、G2-3、G2-4又はG2-5で表される構造を表し、
R1、R2、R3及びR4は、各々独立して、水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY1Y2又は-NY1Y2を表し、
A1は、C-RC又はNを表し、
A2は、C-RE又はNを表し、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)
RA、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C3~C6シクロアルキル、Uによって置換された(C3~C6)シクロアルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、5個までのZで置換されても良いフェノキシ基、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY3Y4、-NY3Y4、シアノ、ニトロ、5個までのZで置換されても良いフェニル基、4個までのZで置換されても良いピリジル基、3個までのZで置換されても良いピリミジル基、3個までの置換基で置換されても良いピラジル基、3個までのZで置換されても良いピリダジル基、3個までのZで置換されても良いチエニル基、3個までのZで置換されても良いフラニル基又はVを表し、
Vは、V-1、V-2、V-3、V-4、V-5又はV-6で表される構造を表し、
Zは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY5Y6、シアノ又はニトロを表し、
Q2、Q3又はQ4はZの置換基数を示し、
Q2は、0、1又は2の整数を表し、
Q3は、0、1、2又は3の整数を表し、
Q4は、0、1、2、3又は4の整数を表し、
Q2、Q3又はQ4が2以上の整数を表す場合には、複数のZは互いに同一であっても互いに相異なっていても良く、
Y1、Y2、Y3、Y4、Y5、Y6は、各々独立して、水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルコキシカルボニル、ハロ(C1~C6)アルコキシカルボニル、C1~C6アルキルスルホニル又はハロ(C1~C6)アルキルスルホニルを表し、
Uは、シアノ、-C(O)OH又は-C(O)NH2を表し、
Dは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、C1~C3アルキルオキシカルボニル、ハロ(C1~C3)アルキルオキシカルボニル、5個までのTで置換されても良いベンゼンカルボニルを表し、
Tは各々独立して水素原子、ハロゲン原子、C1~C3アルキル、ハロ(C1~C3)アルキル、C1~C3アルコキシ、ハロ(C1~C3)アルコキシを表し、
Eは水素原子、C1~C6アルキル、シクロプロピルメチル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、メトキシメチル、エトキシメチル、シアノメチル、シアノエチル、メチルチオメチル、メチルスルホニルメチルを表す。]
<2>
式(1)又は式(2)又は式(3)で表される化合物若しくはその塩又はそれらのN-オキシド。
[式(1)、式(2)及び式(3)中、
G1は、G1-1、G1-2、G1-3、G1-4又はG1-5で表される構造を表し、
G2は、G2-1、G2-2、G2-3、G2-4又はG2-5で表される構造を表し、
R1、R2、R3及びR4は、各々独立して、水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル又はハロ(C1~C6)アルキルスルホニルを表し、
A1は、C-RC又はNを表し、
A2は、C-RE又はNを表し、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)
RA、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C3~C6シクロアルキル、Uによって置換された(C3~C6)シクロアルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY3Y4、シアノ、ニトロ又はVを表し、
Vは、V-1、V-2、V-3、V-4、V-5又はV-6で表される構造を表し、
Zは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY5Y6、シアノ又はニトロを表し、
Q2、Q3又はQ4はZの置換基数を示し、
Q2は、0、1又は2の整数を表し、
Q3は、0、1、2又は3の整数を表し、
Q4は、0、1、2、3又は4の整数を表し、
Q2、Q3又はQ4が2以上の整数を表す場合には、複数のZは互いに同一であっても互いに相異なっていても良く、
Y3、Y4、Y5、Y6は、各々独立して、水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルコキシカルボニル、ハロ(C1~C6)アルコキシカルボニル、C1~C6アルキルスルホニル又はハロ(C1~C6)アルキルスルホニルを表し、
Uは、複数ある場合には各々独立して、シアノ、-C(O)OH又は-C(O)NH2を表し、
Dは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニルを表し、
Eは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニルを表す。]
<3>
A1がNであり、A2がC-REである式(1)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<4>
A1がC-RCであり、A2がNである式(1)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<5>
G1がG1-1であり、A1がNであり、A2がC-REである式(1)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<6>
G1がG1-1であり、A1がC-RCであり、A2がNである式(1)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<7>
A1がNであり、A2がC-REである式(2)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<8>
A1がC-RCであり、A2がNである式(2)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<9>
G2がG2-1であり、A1がNであり、A2がC-REである式(2)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<10>
G2がG2-1であり、A1がC-RCであり、A2がNである式(2)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<11>
G2がG2-1であり、A1がC-RCであり、A2がNであり、RAがC1~C3アルキルスルホニルであり、RB、RDが水素原子であり、RCが5個までのZで置換されても良いフェニル基又はVである式(2)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<12>
2-(3-(エチルスルホニル)-5-(1H-ピラゾール-1-イル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号180)、
2-(3-(エチルスルホニル)-5-(2H-1,2,3-トリアゾール-2-イル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号181)、
2-(3-(エチルスルホニル)-5-(2-(トリフルオロメチル)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号174)、
2-(3-(エチルスルホニル)-5-(3-(トリフルオロメチル)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号175)、
2-(3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号176)、
2-(5-(2,4-ビス(トリフルオロメチル)フェニル)-3-(エチルスルホニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン、
2-(5-(3,5-ビス(トリフルオロメチル)フェニル)-3-(エチルスルホニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号178)、
2-(3-(エチルスルホニル)-5-(2-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン、
2-(3-(エチルスルホニル)-5-(3-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号214)、
2-(3-(エチルスルホニル)-5-(4-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号177)
<13>
A1がNであり、A2がC-REである式(3)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<14>
A1がC-RCであり、A2がNである式(3)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<15>
G2がG2-1であり、A1がNであり、A2がC-REである式(3)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<16>
G2がG2-1であり、A1がC-RCであり、A2がNである式(3)で表される<1>に記載の化合物若しくはその塩又はそれらのN-オキシド。
<17>
<1>~<16>に記載の化合物若しくはその塩又はそれらのN-オキシドと、界面活性剤、固体担体及び液体担体からなる群から選択される少なくとも1つの成分を含む有害生物防除組成物。
<18>
少なくとも1つの他の有害生物防除化合物または薬剤をさらに含む、<17>に記載の有害生物防除組成物。
<19>
前記の少なくとも1つの有害生物防除化合物または薬剤が、
アラニカルブ、アルジカルブ、ベンダイオカルブ、ベンフラカルブ、ブトカルボキシム、ブトキシカルボキシム、カルバリル、カルボフラン、カルボスルファン、エチオフェンカルブ、フェノブカルブ、ホルメタネート、フラチオカルブ、イソプロカルブ、メチオカルブ、メソミル、オキサミル、ピリミカルブ、プロポキスル、チオジカルブ、チオファノックス、トリアザメート、トリメタカルブ、XMC、キシリルカルブ、メトルカルブ、フェノチオカルブ、フェノキシカルブ、アセフェート、アザメチホス、アジンホス-エチル、アジンホス-メチル、エチルチオメトン、クロルエトキシホス、カズサホス、クロレトキシホス、クロルフェンビンホス、クロルメホス、クロルピリホス、クロルピリホスメチル、クマホス、シアノホス、デメトン-S-メチル、ダイアジノン、ジクロルボス、ジクロトホス、ジメトエート、ジメチルビンホス、EPN、エチオン、エトプロホス、ファムフール、フェナミホス、フェニトロチオン、フェンチオン、ホスチアゼート、ヘプテノホス、イミシアホス、イソフェンホス、イソプロピル=O-(メトキシアミノチオホスホリルサリチレート、イソキサチオン、マラチオン、メカルバム、メタミドホス、メチダチオン、メビンホス、モノクロトホス、ナレド、オメトエート、オキシジメトンエチル、パラチオン、パラチオン-メチル、PAP、ホレート、ホサロン、ホスメット、ホスファミドン、ホキシム、ピリミホス-メチル、プロフェノホス、プロペタンホス、プロチオホス、ピラクロホス、ピリダフェンチオン、キナルホス、スルホテップ、テブピリミホス、テメホス、テルブホス、テトラクロルビンホス、チオメトン、トリアゾホス、トリクロルホン、バミドチオン、クロルピリホス-エチル、ジスルフォトン、スルプロホス、フルピラゾホス、フェントエート、ホノホス、トリブホス、エンドスルファン、アルファ-エンドスルファン、ガンマ-HCH、ジコホル、クロルデン、ディルドリン、メトキシクロル、アセトプロール、フィプロニル、エチプロール、ピラフルプロール、ピリプロール、フルフィプロール、ブロフラニリド、アフォキソラネル、フルララネル、サロラネル、フルキサメタミド、ロティラネル、イソシクロシラム、アクリナトリン、アレスリン、d-cis-transアレスリン、d-transアレスリン、ビフェントリン、カッパ-ビフェントリン、ビオアレスリンS-シクロペンテニル、ビオレスメトリン、シクロプロトリン、シフルトリン、ベータ-シフルトリン、シハロトリン、ラムダ-シハロトリン、ガンマ-シハロトリン、シペルメトリン、アルファ-シペルメトリン、ベータ-シペルメトリン、シータ-シペルメトリン、ゼータ-シペルメトリン、シフェノトリン、デルタメトリン、エンペントリン、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、フルシトリネート、フルメトリン、タウ-フルバリネート、ハルフェンプロックス、イミプロトリン、カデスリン、ペルメトリン、フェノトリン、プラレトリン、ピレトリン、レスメトリン、シラフルオフェン、テフルトリン、カッパ-テフルトリン、フタルスリン、テトラメトリン、トラロメトリン、トランスフルトリン、メトキサジアゾン、メトフルトリン、プロフルトリン、ピレトラム、テラレトリン、モンフルオロスリン、ヘプタフルトリン、メペルフルスリン、テトラメチルフルスリン、ジメフルトリン、クロロパラレスリン、イプシロン-メトフルスリン、イプシロン-モンフルオスリン、プロトリフェンブト、アセタミプリド、クロチアニジン、ジノテフラン、イミダクロプリド、ニテンピラム、チアクロプリド、チアメトキサム、スルホキサフロル、フルピラジフロン、トリフルメゾピリム、ジクロロメゾチアズ、フルピリミン、スピノサド、スピネトラム、アバメクチン、イベルメクチン、エマメクチン安息香酸塩、ミルベメクチン、レピメクチン、ヒドロプレン、キノプレン、ジオフェノラン、メトプレン、ピリプロキシフェン、ピメトロジン、フロニカミド、エトキサゾール、ジアフェンチウロン、アゾシクロチン、シヘキサチン、酸化フェンブタスズ、プロパルギット、テトラジホン、クロルフェナピル、トラロピリル、DNOC、ベンスルタップ、カルタップ、チオシクラム、チオスルタップ、チオスルタップ-ナトリウム、ビストリフルロン、クロルフルアズロン、ジフルベンズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、ノビフルムロン、テフルベンズロン、トリフルムロン、ビストリフルロン、ブプロフェジン、シロマジン、クロマフェノジド、ハロフェノジド、メトキシフェノジド、テブフェノジド、アミトラズ、ヒドラメチルノン、アセキノシル、フルアクリピリム、ピリミノストロビン、フルフェノキシストロビン、フェナザキン、フェンピロキシメート、ピリミジフェン、ピリダベン、テブフェンピラド、トルフェンピラド、ピフルブミド、メタフルミゾン、スピロジクロフェン、スピロテトラマト、スピロメシフェン、スピロピディオン、シフルメトフェン、シエノピラフェン、フルベンジアミド、クロラントラニリプロール、シアントラニリプロール、シクラニリプロール、テトラニリプロール、シハロジアミド、テトラクロラントラニリプロール、キノメチオネート、ヘキシチアゾクス、ビフェナゼート、フルフェネリム、ピリフルキナゾン、フロメトキン、フルオピラム、フルアザインドリジン、アミドフルメト、チクロピラゾフロル、チオキサザフェン、オキサゾスルフィル、
ニコチン、クロロピクリン、フッ化スルフリル、クリロチエ、クロフェンテジン、ジフロビダジン、ロテノン、インドキサカルブ、ピペロニルブトキシド、クロルジメホルム、ピリダリル、アザジラクチン、ベンゾキシメート、アフィドピロペン、フルヘキサホン、フルエンスルホン、ベンクロチアズ、カルゾール、殺虫性石鹸、ジメヒポ、ニチアジン、ホウ酸塩、メタアルデヒド、リアノジン、スルフルラミド、アシノナピル、ベンズピリモキサン、3-ブロモ-N-(2,4-ジクロロ-6-(メチルカルバモイル)フェニルイル)-1-(3,5-ジクロロピリジン-2-イル)-1H-ピラゾール-5-カルボキサミド、
メタラキシル、メタラキシル-M、オキサジキシル、オフラセ、ベナラキシル、ベナラキシル-M、キララキシル、オフラース、フララキシル、シプロフラン、ブプリメート、ジメチリモール、エチリモール、ヒメキサゾール、ヒドロキシイソキサゾール、オキサチアピプロリン、オクチリノン、オキソリニック酸、ベノミル、チオファネートメチル、カーベンダジム、フベリダゾール、チアベンダゾール、デバカルブ、ジエトフェンカルブ、ゾキサミド、エタボキサム、ペンシクロン、フルオピコリド、フルオピモミド、ジフルメトリム、ブピリメート、ベノダニル、フルトラニル、メプロニル、イソフェタミド、フェンフラム、オキシカルボキシン、カルボキシン、チフルザミド、フルキサピロキサド、フラメトピル、ペンフルフェン、ペンチオピラド、ベンゾビンジフルピル、ビキサフェン、イソピラザム、セダキサン、インピルフルキサム、フルインダピル、イソフルシプラム、ピラプロポイン、ボスカリド、アゾキシストロビン、コウメトキシストロビン、クレソキシムメチル、トリフロキシストロビン、ピコキシストロビン、ピラクロストロビン、ジモキシストロビン、メトミノストロビン、オリサストロビン、フルオキサストロビン、ピラオキシストロビン、ピラメトストロビン、フルフェノキシストロビン、フェナミンストロビン、エノキサストロビン、クモキシストロビン、マンデストロビン、トリクロピリカルブ、ファモキサドン、フェンアミドン、トリクロピリカルブ、ピリベンカルブ、シアゾファミド、アミスルブロム、ビナパクリル、メプチルジノカルブ、ジノカップ、フルアジナム、フェリムゾン、酢酸-フェンチン、塩化フェンチン、水酸化フェンチン、水酸化トリフェニルスズ、酢酸トリフェニルスズ、オキシン銅、シルチオファム、アメトクトラジン、メパニピリム、ニトラピリン、ピリメサニル、シプロジニル、ブラストサイジンS、カスガマイシン、カスガマイシン塩酸塩水和物、ストレプトマイシン、オキシテトラサイクリン、キノキシフェン、プロキナジド、フルジオキソニル、フェンピクロニル、フルオロイミド、プロシミドン、イプロジオン、ビンクロゾリン、エジフェンホス、イプロベンホス、ピラゾホス、イソプロチオラン、プロパモカルブ、プロパモカルブ塩酸塩、ゴセイカユプテ抽出物、トリホリン、ピリフェノックス、ピリソキサゾール、フェナリモル、ヌアリモル、アザコナゾール、ブロムコナゾール、ジニコナゾール、ジニコナゾール-M、エポキシコナゾール、フルキンコナゾール、オキスポコナゾール、ペフラゾエート、ジフェノコナゾール、フェンブコナゾール、イミベンコナゾール、イプコナゾール、メトコナゾール、テトラコナゾール、トリアジメホン、トリアジメノール、トリチコナゾール、ウニコナゾール、イマザリル、ビテルタノール、トリフルミゾール、エタコナゾール、プロピコナゾール、ペンコナゾール、フルシラゾール、フルトリアホール、ミクロブタニル、パクロブトラゾール、プロチオコナゾール、シプロコナゾール、テブコナゾール、ヘキサコナゾール、プロクロラズ、シメコナゾール、イプフェントリフルコナゾール、アルジモルフ、ドデモルフ、酢酸ドデモルフ、トリデモルフ、フェンプロピモルフ、ジメトモルフ、フルモルフ、ピリモルフ、ピペラリン、フェンプロピディン、スピロキサミン、フェンヘキサミド、フェンピラザミン、フェルバム、メタム、メタスルホカルブ、メチラム、チラム、マンゼブ、マンネブ、ジネブ、ジラム、ポリカーバメート、プロビネブ、チウラム、ピリブチカルブ、バリダマイシン、ミルジオマイシン、ポリオキシン、ベンチアバリカルブ、ベンチアバリカルブイソプロピル、バリフェナレート、イプロバリカルブ、マンジプロパミド、フェンピコキサミド、フロリルピコキサミド、フサライド、ピロキロン、トリシクラゾール、カルプロパミド、ジクロシメット、フェノキサニル、アシベンゾラル-S-メチル、プロベナゾール、ジクロベンチアゾクス、チアジニル、イソチアニル、シモキサニル、ホセチル、テクロフタラム、トリアゾキシド、フルスルファミド、ジクロメジン、シフルフェナミド、メトラフェノン、ピリオフェノン、フルチアニル、テブフロキン、イプフルフェノキン、ホセチルアルミニウム、トルクロホス-メチル、エクロメゾール、トルプロカルブ、メフェントリフルコナゾール、キノフメリン、ピジフルメトフェン、ボルドー混合液、酢酸銅、塩基性硫酸銅、オキシ塩化銅、水酸化第二銅、オキシキノリン銅、銅、硫黄、キャプタン、カプタホール、フォルペット、アニラジン、クロロタロニル、ジクロロフェン、ペンタクロロフェノール及びその塩、ヘキサクロロベンゼン、キントゼン、イミノクタジン酢酸塩、イミノクタジンアルベシル酸塩、グアニジン、ドジン、ドジン遊離塩基、グアザチン、グアザチン酢酸塩、アルベシレート、ジチアノン、フルオルイミド、トリルフルアニド、ジクロフルアニド、ジノブトン、ダゾメット、ピラジフルミド、アミノピリフェン、メチルテトラプロール、ピリダクロメチル、
ジピメチトロン、ピカルブトラゾクス、テクナゼン、ニトルタール-イソプロピル、ジシクロメット、アシベンゾラル、プロヘキサジオン-カルシウム、ブロノポール、ジフェニルアミン、フルメトベル、ベントキサジン、ビフェニル、クロロネブ、CNA、ヨードカルブ、プロチオカルブ、並びに
Bacillus属、及びそれらにより産生された殺虫性タンパク、殺菌性タンパク、Bt作物により産生された殺虫性タンパク、殺菌性タンパク、昆虫病原性バクテリア、昆虫病原性ウイルスおよび昆虫病原性菌類
からなる群から選択される、<18>に記載の有害生物防除組成物。
<20>
前記有害生物が動物寄生性害虫であり、動物又は鳥類に投与される<18>に記載の有害生物防除組成物。
<21>
有害生物またはその環境に<1>に記載の化合物若しくはその塩又はそれらのN-オキシドを有害生物に接触させる、有害生物を防除する方法。
<22>
作物の活力を高める方法であって、作物又は作物の種子に<1>に記載の化合物若しくはその塩又はそれらのN-オキシドを接触させる、前記方法。
<23>
<1>に記載の化合物若しくはその塩又はそれらのN-オキシドで処理された種子であって、処理後の種子全体の約0.0001~約50重量%の量の<1>に記載の化合物若しくはその塩又はそれらのN-オキシドを含む、前記種子。
<24>
<1>に記載の化合物若しくはその塩又はそれらのN-オキシドで作物の種子を処理する工程を含む、種子の製造方法であって、
処理後の種子が種子全体の約0.0001~約50重量%の量の<1>に記載の化合物若しくはその塩又はそれらのN-オキシドを含む、
前記方法。That is, the present invention relates to the following, but is not limited thereto.
<1>
A compound represented by formula (1) or formula (2) or formula (3) or a salt thereof or an N-oxide thereof.
[In formula (1), formula (2) and formula (3),
G 1 represents a structure represented by G 1 -1, G 1 -2, G 1 -3, G 1 -4 or G 1 -5,
G 2 represents a structure represented by G 2 -1, G 2 -2, G 2 -3, G 2 -4 or G 2 -5,
R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 1 -C 6 alkoxy, a halo( C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 )alkylsulfonyl, (C=O)NY 1 Y 2 or - represents NY 1 Y 2 ,
A 1 represents C-R C or N,
A 2 represents C-R E or N (here, either A 1 or A 2 is N and the other is C-R C or C-R E ).
R A , R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 3 -C 6 cycloalkyl , (C 3 -C 6 )cycloalkyl substituted by U, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, phenoxy group optionally substituted with up to 5 Z, C 1 -C 6 C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, (C=O)NY 3 Y 4 , -NY 3 Y 4 , cyano, nitro, phenyl group optionally substituted with up to 5 Zs, pyridyl group optionally substituted with up to 4 Zs, Pyrimidyl group optionally substituted with up to 3 Zs, pyrazyl group optionally substituted with up to 3 substituents, pyridazyl group optionally substituted with up to 3 Zs, substituted with up to 3 Zs represents a thienyl group which may be substituted with a thienyl group, a furanyl group which may be substituted with up to 3 Z or V,
V represents a structure represented by V-1, V-2, V-3, V-4, V-5 or V-6,
Z is each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 - C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, -NY 5 Y 6 represents cyano or nitro,
Q2, Q3 or Q4 indicates the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3,
Q4 represents an integer of 0, 1, 2, 3 or 4,
When Q2, Q3 or Q4 represents an integer of 2 or more, the plurality of Z's may be the same or different from each other,
Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 each independently represent a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkyl Carbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo(C 1 -C 6 )alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or halo(C 1 -C 6 )alkylsulfonyl represents,
U represents cyano, -C(O)OH or -C(O) NH2 ,
D is a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, C 1 -C 3 alkyloxycarbonyl, halo(C 1 -C 3 )alkyloxycarbonyl, optionally substituted with up to 5 T Good represents benzenecarbonyl,
Each T independently represents a hydrogen atom, a halogen atom, C 1 -C 3 alkyl, halo(C 1 -C 3 )alkyl, C 1 -C 3 alkoxy, halo(C 1 -C 3 )alkoxy,
E is a hydrogen atom, C1 - C6 alkyl, cyclopropylmethyl, halo( C1 - C6 )alkyl, C1 - C6 alkylcarbonyl, C3 - C6 cycloalkylcarbonyl, halo( C1 -C6 ) ) alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl. ]
<2>
A compound represented by formula (1) or formula (2) or formula (3) or a salt thereof or an N-oxide thereof.
[In formula (1), formula (2) and formula (3),
G 1 represents a structure represented by G 1 -1, G 1 -2, G 1 -3, G 1 -4 or G 1 -5,
G 2 represents a structure represented by G 2 -1, G 2 -2, G 2 -3, G 2 -4 or G 2 -5,
R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 1 -C 6 alkoxy, a halo( C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl or halo(C 1 -C 6 )alkylsulfonyl,
A 1 represents C-R C or N,
A 2 represents C-R E or N (here, either A 1 or A 2 is N and the other is C-R C or C-R E ).
R A , R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 3 -C 6 cycloalkyl , (C 3 -C 6 )cycloalkyl substituted by U, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 -C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, -NY 3 Y 4 , cyano, nitro or V represents,
V represents a structure represented by V-1, V-2, V-3, V-4, V-5 or V-6,
Z is each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 - C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, -NY 5 Y 6 represents cyano or nitro,
Q2, Q3 or Q4 indicates the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3,
Q4 represents an integer of 0, 1, 2, 3 or 4,
When Q2, Q3 or Q4 represents an integer of 2 or more, the plurality of Z's may be the same or different from each other,
Y 3 , Y 4 , Y 5 , and Y 6 each independently represent a hydrogen atom, C 1 to C 6 alkyl, halo(C 1 to C 6 )alkyl, C 1 to C 6 alkylcarbonyl, or halo(C 1 -C 6 ) alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo(C 1 -C 6 )alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or halo(C 1 -C 6 )alkylsulfonyl,
When there is a plurality of U, each independently represents cyano, -C(O)OH or -C(O) NH2 ,
D is a hydrogen atom, C 1 -C 6 alkyl, halo (C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, halo (C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo (C 1 -C 6 ) represents alkylsulfonyl,
E is a hydrogen atom, C 1 -C 6 alkyl, halo (C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, halo (C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo (C 1 -C 6 ) represents alkylsulfonyl. ]
<3>
The compound according to <1> , a salt thereof, or an N-oxide thereof, represented by formula (1), wherein A 1 is N and A 2 is CR E.
<4>
The compound according to <1> , or a salt thereof, or an N-oxide thereof, represented by formula (1), wherein A 1 is C--R C and A 2 is N.
<5>
The compound or its salt or its N-oxide according to <1> represented by formula (1), wherein G 1 is G 1 -1, A 1 is N, and A 2 is CR E .
<6>
The compound or its salt or its N-oxide according to <1> represented by formula (1), where G 1 is G 1 -1, A 1 is CR C , and A 2 is N .
<7>
The compound according to <1> , a salt thereof, or an N-oxide thereof, represented by formula (2), wherein A 1 is N and A 2 is CR E.
<8>
The compound according to <1> , a salt thereof, or an N-oxide thereof, represented by formula (2), wherein A 1 is C--R C and A 2 is N.
<9>
The compound or its salt or its N-oxide according to <1> represented by formula (2), wherein G 2 is G 2 -1, A 1 is N, and A 2 is CR E .
<10>
The compound or its salt or its N-oxide according to <1> represented by formula (2), where G 2 is G 2 -1, A 1 is CR C , and A 2 is N .
<11>
G 2 is G 2 -1, A 1 is C-R C , A 2 is N, R A is C 1 to C 3 alkylsulfonyl, and R B and R D are hydrogen atoms; , R C is a phenyl group or V optionally substituted with up to 5 Zs, or a salt thereof, or an N-oxide thereof, according to <1>, represented by formula (2).
<12>
2-(3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a ] Pyridine (compound number 180),
2-(3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo [1,5-a]pyridine (compound number 181),
2-(3-(ethylsulfonyl)-5-(2-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 174),
2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 175),
2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 176),
2-(5-(2,4-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1 ,5-a]pyridine,
2-(5-(3,5-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1 ,5-a]pyridine (compound number 178),
2-(3-(ethylsulfonyl)-5-(2-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine,
2-(3-(ethylsulfonyl)-5-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 214),
2-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] Pyridine (Compound No. 177)
<13>
The compound according to <1> , a salt thereof, or an N-oxide thereof, represented by formula (3), wherein A 1 is N and A 2 is CR E.
<14>
The compound according to <1> , a salt thereof, or an N-oxide thereof, represented by formula (3), wherein A 1 is C--R C and A 2 is N.
<15>
The compound or its salt or its N-oxide according to <1> represented by formula (3), wherein G 2 is G 2 -1, A 1 is N, and A 2 is CR E .
<16>
The compound or its salt or its N-oxide according to <1> represented by formula (3), where G 2 is G 2 -1, A 1 is CR C , and A 2 is N .
<17>
A pest control composition comprising the compound described in <1> to <16>, a salt thereof, or an N-oxide thereof, and at least one component selected from the group consisting of a surfactant, a solid carrier, and a liquid carrier.
<18>
The pest control composition according to <17>, further comprising at least one other pest control compound or drug.
<19>
Said at least one pest control compound or agent is
Aranicarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formanate, furathiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiophyl Nox, triazamate, trimetacarb, XMC, xylylcarb, metolcarb, phenothiocarb, phenoxycarb, acephate, azamethyphos, azinphos-ethyl, azinphos-methyl, ethylthiometone, chlorethoxyfos, cassafos, chlorethoxyfos, chlorfenvinfos, chlormefos, chlorpyrifos, chlorpyrifos-methyl , coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, EPN, ethion, ethoprofos, famfur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imisiaphos, isofenphos, isopropyl O-( Methoxyaminothiophosphorylsalicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydimethoneethyl, parathion, parathion-methyl, PAP, phorate, phosalone, phosmet, phosfamidone, phoxim, pirimiphos - Methyl, profenofos, propetanphos, prothiofos, pyraclofos, pyridafenthion, quinalfos, sulfotep, tebupirimifos, temefos, terbufos, tetrachlorvinfos, thiomethone, triazophos, trichlorfon, bamidothione, chlorpyrifos-ethyl, disulfoton, sulprofos, flupyrazofos, fentoate, honofos, Tribufos, endosulfan, alpha-endosulfan, gamma-HCH, dicofol, chlordane, dieldrin, methoxychlor, acetoprol, fipronil, ethiprole, pyrafluprole, pyriprole, flufiprole, brofuranilide, afoxolaner, fluralaner, sarolaner, fluxamethamide, rotilaner, isocyclosilam , acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- Cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrinate , flumethrin, tau-fluvalinate, halfenprox, imiprothrin, cadethrin, permethrin, phenothrin, prarethrin, pyrethrin, resmethrin, cilafluofen, tefluthrin, kappa-tefluthrin, phthalthrin, tetramethrin, tralomethrin, transfluthrin, methoxadiazone, metofluthrin, profluthrin, Pyrethram, telarethrin, monfluorothrin, heptafluthrin, meperfluthrin, tetramethylfluthrin, dimefluthrin, chloropararethrin, epsilon-methfluthrin, epsilon-monfluthrin, protrifenbut, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, Thiacloprid, thiamethoxam, sulfoxaflor, flupyradifurone, triflumezopyrim, dichloromesothiaz, flupyrimine, spinosad, spinetoram, abamectin, ivermectin, emamectin benzoate, milbemectin, lepimectin, hydroprene, quinoprene, diphenolan, methoprene, pyriproxyfen, pymetrozine, flonicamid, etoxazole, diafenthiuron, azocyclotine, cyhexatin, fenbutastin oxide, propargite, tetradifon, chlorfenapyr, tralopyril, DNOC, bensultap, cartap, thiocyclam, thiosultap, thiosultap-sodium, bistrifluron, chlorfluazuron, diflubenzuron, flu Cycloxuron, flufenoxuron, hexaflumuron, lufenuron, Novaluron, noviflumuron, teflubenzuron, triflumuron, bistrifluron, buprofezine, cyromazine, clomafenozide, halofenozide, methoxyfenozide, tebufenozide, amitraz, hydramethylnon, acequinocyl, fluacripyrim, pyrimino Strobin, flufenoxystrobin, fenazaquine, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, pyflubumide, metaflumizone, spirodiclofen, spirotetramate, spiromesifen, spiropidion, cyflumetofen, cyenopyrafen, flubendiamide, chlorantrani Riprole, cyantraniliprole, cyclaniliprole, tetraniliprole, cyhalodiamide, tetrachlorantraniliprole, chinomethionate, hexythiazox, bifenazate, flufenerim, pyrifluquinazone, flomethquine, fluopyram, fluazaindolizine, amidoflumeth, ticlopyrazole Furol, thioxazaphene, oxazosulfil,
Nicotine, chloropicrin, sulfuryl fluoride, krylotie, clofentezine, diflobidazine, rotenone, indoxacarb, piperonyl butoxide, chlordimeform, pyridalyl, azadirachtin, benzoximate, afidopyropene, fluhexaphone, fluensulfone, bencrothiaz, carzole, insecticidal soap, Dimehypo, nithiazine, borate, metaldehyde, ryanodine, sulfuramide, acinonapyr, benzpyrimoxane, 3-bromo-N-(2,4-dichloro-6-(methylcarbamoyl)phenyl)-1-(3, 5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxamide,
Metalaxyl, metalaxyl-M, oxadixyl, ofrase, benalaxyl, benalaxyl-M, chiralaxyl, ofrase, furalaxyl, ciprofuran, buprimate, dimethylimole, ethyrimole, himexazole, hydroxyisoxazole, oxathiapiproline, octyrinone, oxolinic acid, benomyl, thiophanate methyl , carbendazim, fuberidazole, thiabendazole, debacarb, diethofencarb, zoxamide, ethaboxam, pencicron, fluopicolide, fluopimomide, diflumethrim, bupirimate, benodanil, flutolanil, mepronil, isofetamide, fenflam, oxycarboxin, carboxin, thifluzamide, fluxapiroxad, furametopyr , penflufen, penthiopyrad, benzobine diflupyr, bixafen, isopyrazam, sedaxane, impirfluxam, fluindapir, isoflucipram, pyrapropoin, boscalid, azoxystrobin, coumethoxystrobin, cresoxime methyl, trifloxystrobin, picoxy Strobin, pyraclostrobin, dimoxystrobin, metominostrobin, orysastrobin, fluoxastrobin, pyraoxystrobin, pyramethastrobin, fluphenoxystrobin, phenaminestrobin, enoxastrobin, spideroxystrobin, Mandestrobin, triclopiricarb, famoxadone, fenamidon, triclopiricarb, pyribencarb, cyazofamid, amisulbrome, binapacryl, meptyldinocarb, dinocap, fluazinam, felimzone, fentin acetate, fentin chloride, fentin hydroxide, trihydroxide Phenyltin, triphenyltin acetate, oxine copper, silthiopham, ametoctrazine, mepanipirim, nitrapyrin, pyrimesanil, cyprodinil, blasticidin S, kasugamycin, kasugamycin hydrochloride hydrate, streptomycin, oxytetracycline, quinoxyfen, proquinazide, fludioxonil, fenpiclonil, fluoro Imide, procymidone, iprodione, vinclozolin, edifenphos, iprobenfos, pyrazofos, isoprothiolane, propamocarb, propamocarb hydrochloride, goseicajepute extract, triforine, pyrifenox, pyrisoxazole, fenarimol, nuarimol, azaconazole, bromuconazole, diniconazole, diniconazole-M , epoxiconazole, fluquinconazole, oxpoconazole, pefurazoate, difenoconazole, fenbuconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, imazalil, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, flutriafol, myclobutanil, paclobutrazole, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, ipfentrifluconazole, aldimorph, Dodemorph, dodemorph acetate, tridemorph, fenpropimorph, dimethomorph, flumorph, pirimorph, piperaline, fenpropidin, spiroxamine, phenhexamide, fenpyrazamine, ferbam, metham, metasulfocarb, methiram, thiram, mancozeb, maneb, zineb, ziram , polycarbamate, probineb, thiuram, pyributicarb, validamycin, mildiomycin, polyoxin, bentiavaricarb, bentiavaricarb isopropyl, variphenarate, iprovaricarb, mandipropamide, fenpicoxamide, florylpicoxamide, fusaride, Pyroquilone, tricyclazole, carpropamide, diclosymet, phenoxanil, acibenzolar-S-methyl, probenazole, dichlorbenziazox, thiazinil, isotianil, cimoxanil, fosetyl, tecroftalam, triazoxide, fursulfamide, diclomedine, cyflufenamide, metrafenone, piriophenone, flutianil, tebufloquine, iip Flufenoquine, fosetylaluminum, tolclofos-methyl, eclomezole, tolprocarb, mefentrifluconazole, quinofumeline, pydiflumetofen, Bordeaux mixture, copper acetate, basic copper sulfate, copper oxychloride, cupric hydroxide, oxy Quinoline copper, copper, sulfur, captan, captafol, folpet, anilazine, chlorothalonil, dichlorophen, pentachlorophenol and its salts, hexachlorobenzene, quintozene, iminoctadine acetate, iminoctadine albesylate, guanidine, dodine, dodine free base , guazatine, guazatine acetate, albesylate, dithianone, fluorimide, tolylfluanid, dichlofluanid, dibutone, dazomet, pyradiflumide, aminopyrifene, methyltetraprole, pyridacromethyl,
dipimethitron, picarbutrazox, technazen, nitrtal-isopropyl, dicyclomet, acibenzolar, prohexadione-calcium, bronopol, diphenylamine, flumethover, bentoxazine, biphenyl, chloroneb, CNA, iodocarb, prothiocarb, and the genus Bacillus and those produced by them. selected from the group consisting of insecticidal proteins, fungicidal proteins, insecticidal proteins produced by Bt crops, fungicidal proteins, entomopathogenic bacteria, entomopathogenic viruses, and entomopathogenic fungi, as described in <18> pest control composition.
<20>
The pest control composition according to <18>, wherein the pest is an animal parasitic pest and is administered to animals or birds.
<21>
A method for controlling pests, which comprises bringing the compound according to <1>, a salt thereof, or an N-oxide thereof into contact with the pests or their environment.
<22>
A method for increasing the vigor of crops, the method comprising: contacting crops or seeds of crops with the compound described in <1>, a salt thereof, or an N-oxide thereof.
<23>
Seeds treated with the compound described in <1>, a salt thereof, or their N-oxide, wherein the compound described in <1> is present in an amount of about 0.0001 to about 50% by weight of the whole seed after treatment. or a salt thereof or an N-oxide thereof.
<24>
A method for producing seeds, comprising a step of treating crop seeds with the compound described in <1>, a salt thereof, or an N-oxide thereof,
The treated seeds contain the compound according to <1> or a salt thereof or an N-oxide thereof in an amount of about 0.0001 to about 50% by weight of the whole seed;
Said method.
本発明による式(1)、式(2)、式(3)で表される化合物若しくはその塩又はそれらのN-オキシドは、有害生物に対して極めて優れた防除効果を示し、有害生物防除剤として有用である。 The compounds represented by formulas (1), (2), and (3) or their salts or their N-oxides according to the present invention exhibit extremely excellent control effects against pests, and are effective as pest control agents. It is useful as
本明細書において、以下の用語の定義や意味は、それぞれ次のとおりである。 In this specification, the definitions and meanings of the following terms are as follows.
また、本発明に包含される化合物は、1個又は2個以上の不斉炭素原子又は不斉硫黄原子又は軸不斉の存在に起因する光学活性体が存在するが、本発明は全ての光学活性体又はラセミ体を包含する。 In addition, the compounds included in the present invention have optically active forms due to the presence of one or more asymmetric carbon atoms, asymmetric sulfur atoms, or axial asymmetry, but the present invention does not cover all optical Includes active form or racemic form.
また、本発明に包含される化合物には、置換基の種類によって互変異性体が存在する場合があるが、本発明は全ての互変異性体又は任意の割合で含む互変異性体の混合物を包含するものである。 In addition, the compounds included in the present invention may have tautomers depending on the type of substituent, but the present invention covers all tautomers or a mixture of tautomers in any proportion. This includes:
また、本発明に包含される化合物には、イミノ基に起因する幾何異性体が存在する場合があるが、本発明は全ての幾何異性体又は任意の割合で含む幾何異性体の混合物を包含するものである。 In addition, the compounds included in the present invention may have geometric isomers due to the imino group, but the present invention includes all geometric isomers or a mixture of geometric isomers in any proportion. It is something.
イミノ基に起因する幾何異性体は、例えば、式(1)で表されるDと、イミノ基窒素原子との波線で表される結合からなり、E体、Z体又はE体とZ体を任意の割合で含む異性体の混合物であることを示す。 Geometric isomers caused by imino groups are, for example, composed of a bond represented by a wavy line between D represented by formula (1) and the nitrogen atom of the imino group, and are E-form, Z-form, or E-form and Z-form. Indicates a mixture of isomers in any proportion.
本発明に包含される化合物のうちで、常法に従って塩にすることができるものは、例えば、フッ化水素酸、塩酸、臭化水素酸、ヨウ化水素酸等のハロゲン化水素酸の塩、硝酸、硫酸、燐酸、塩素酸、過塩素酸等の無機酸の塩、メタンスルホン酸、エタンスルホン酸、トリフルオロメタンスルホン酸、ベンゼンスルホン酸、p-トルエンスルホン酸等のスルホン酸の塩、ギ酸、酢酸、プロピオン酸、トリフルオロ酢酸、フマール酸、酒石酸、蓚酸、マレイン酸、リンゴ酸、コハク酸、安息香酸、マンデル酸、アスコルビン酸、乳酸、グルコン酸、クエン酸等のカルボン酸の塩、グルタミン酸、アスパラギン酸等のアミノ酸の塩、リチウム、ナトリウム、カリウムといったアルカリ金属の塩、カルシウム、バリウム、マグネシウムといったアルカリ土類金属の塩、アルミニウムの塩、テトラメチルアンモニウム塩、テトラブチルアンモニウム塩、ベンジルトリメチルアンモニウム塩等の四級アンモニウム塩である。 Among the compounds included in the present invention, those that can be converted into salts according to conventional methods include salts of hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid, and hydroiodic acid; Salts of inorganic acids such as nitric acid, sulfuric acid, phosphoric acid, chloric acid, perchloric acid, salts of sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, trifluoromethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, formic acid, Salts of carboxylic acids such as acetic acid, propionic acid, trifluoroacetic acid, fumaric acid, tartaric acid, oxalic acid, maleic acid, malic acid, succinic acid, benzoic acid, mandelic acid, ascorbic acid, lactic acid, gluconic acid, citric acid, glutamic acid, Salts of amino acids such as aspartic acid, salts of alkali metals such as lithium, sodium, potassium, salts of alkaline earth metals such as calcium, barium, magnesium, salts of aluminum, tetramethylammonium salts, tetrabutylammonium salts, benzyltrimethylammonium salts It is a quaternary ammonium salt such as
本発明化合物において、N-オキシドとは、複素環上の環を構成する窒素原子が酸化された化合物である。N-オキシドを形成しうる複素環としては、例えば、ピリジン環を含む縮合環が挙げられる。 In the compound of the present invention, the N-oxide is a compound in which a nitrogen atom constituting a ring on a heterocyclic ring is oxidized. Examples of the heterocycle that can form an N-oxide include a fused ring containing a pyridine ring.
次に、本明細書において示した各置換基の具体例を以下に示す。ここで、n-はノルマル、i-はイソ、s-はセカンダリー、tert-はターシャリー、及びc-はシクロを各々意味する。 Next, specific examples of each substituent shown in this specification are shown below. Here, n- means normal, i- means iso, s- means secondary, tert- means tertiary, and c- means cyclo.
本明細書における「ハロゲン原子」としては、フッ素原子、塩素原子、臭素原子及びヨウ素原子が挙げられる。尚、本明細書中「ハロ」の表記もこれらのハロゲン原子を表す。 In this specification, the "halogen atom" includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. In addition, the notation "halo" in this specification also represents these halogen atoms.
本明細書における「Ca~Cbアルキル」の表記は、炭素原子数がa~b個よりなる直鎖状又は分岐鎖状の炭化水素基を表し、例えば、メチル基、エチル基、n-プロピル基、i-プロピル基、n-ブチル基、i-ブチル基、s-ブチル基、tert-ブチル基、n-ペンチル基、1,1-ジメチルプロピル基、n-ヘキシル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。In this specification, the expression "C a - C b alkyl" represents a linear or branched hydrocarbon group having a to b carbon atoms, such as a methyl group, an ethyl group, an n- Specific examples include propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, tert-butyl group, n-pentyl group, 1,1-dimethylpropyl group, n-hexyl group, etc. and selected within each specified number of carbon atoms.
本明細書における「ハロ(Ca~Cb)アルキル」の表記は、炭素原子に結合した水素原子が任煮の数のハロゲン原子によって置換された、炭素原子数がa~b個よりなる直鎖状又は分岐鎖状の炭化水素基を表し、このとき、2個以上のハロゲン原子によって置換されている場合、それらのハロゲン原子は互いに同一でも、互いに相異なっていてもよい。例えば、フルオロメチル基、クロロメチル基、ブロモメチル基、ヨードメチル基、ジフルオロメチル基、ジクロロメチル基、トリフルオロメチル基、クロロジフルオロメチル基、トリクロロメチル基、ブロモジフルオロメチル基、1-フルオロエチル基、2-フルオロエチル基、2-クロロエチル基、2-ブロモエチル基、2,2-ジフルオロエチル基、2,2,2-トリフルオロエチル基、2-クロロ-2,2-ジフルオロエチル基、2,2,2-トリクロロエチル基、2-ブロモ-2,2-ジフルオロエチル基、1,1,2,2-テトラフルオロエチル基、2-クロロ-1,1,2-トリフルオロエチル基、2-クロロ-1,1,2,2-テトラフルオロエチル基、ペンタフルオロエチル基、2,2-ジフルオロプロピル基、3,3,3-トリフルオロプロピル基、3-ブロモ-3,3-ジフルオロプロピル基、2,2,3,3-テトラフルオロプロピル基、2,2,3,3,3-ペンタフルオロプロピル基、1,1,2,3,3,3-ヘキサフルオロプロピル基、ヘプタフルオロプロピル基、2,2,2-トリフルオロ-1-(メチル)エチル基、2,2,2-トリフルオロ-1-(トリフルオロメチル)エチル基、1,2,2,2-テトラフルオロ-1-(トリフルオロメチル)エチル基、2,2,3,4,4,4-ヘキサフルオロブチル基、2,2,3,3,4,4,4-ヘプタフルオロブチル基、ノナフルオロブチル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。In this specification, the expression "halo(C a -C b )alkyl" refers to a straight alkyl group consisting of a to b carbon atoms, in which the hydrogen atom bonded to the carbon atom is replaced by an arbitrary number of halogen atoms. It represents a chain or branched hydrocarbon group, and in this case, when it is substituted with two or more halogen atoms, those halogen atoms may be the same or different from each other. For example, fluoromethyl group, chloromethyl group, bromomethyl group, iodomethyl group, difluoromethyl group, dichloromethyl group, trifluoromethyl group, chlorodifluoromethyl group, trichloromethyl group, bromodifluoromethyl group, 1-fluoroethyl group, 2 -fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2, 2-trichloroethyl group, 2-bromo-2,2-difluoroethyl group, 1,1,2,2-tetrafluoroethyl group, 2-chloro-1,1,2-trifluoroethyl group, 2-chloro- 1,1,2,2-tetrafluoroethyl group, pentafluoroethyl group, 2,2-difluoropropyl group, 3,3,3-trifluoropropyl group, 3-bromo-3,3-difluoropropyl group, 2 , 2,3,3-tetrafluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, 1,1,2,3,3,3-hexafluoropropyl group, heptafluoropropyl group, 2 , 2,2-trifluoro-1-(methyl)ethyl group, 2,2,2-trifluoro-1-(trifluoromethyl)ethyl group, 1,2,2,2-tetrafluoro-1-(trifluoro-1-(trifluoromethyl)ethyl group, Specific examples include fluoromethyl)ethyl group, 2,2,3,4,4,4-hexafluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, nonafluorobutyl group, etc. and are selected within each specified number of carbon atoms.
「Ca~Cbシクロアルキル」の表記は、炭素原子数がa~b個よりなる環状の炭化水素基を表わし、3員環から6員環までの単環又は複合環構造を形成することが出来る。また、各々の環は指定の炭素原子数の範囲でアルキル基によって任意に置換されていてもよい。例えばシクロプロピル基、1-メチルシクロプロピル基、2-メチルシクロプロピル基、2,2-ジメチルシクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。The notation "C a - C b cycloalkyl" represents a cyclic hydrocarbon group consisting of a to b carbon atoms, forming a monocyclic or complex ring structure of 3 to 6 membered rings. I can do it. Furthermore, each ring may be optionally substituted with an alkyl group within the specified number of carbon atoms. For example, specific examples include cyclopropyl group, 1-methylcyclopropyl group, 2-methylcyclopropyl group, 2,2-dimethylcyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc., and each designated carbon atom Selected from a range of numbers.
「Ca~Cbアルコキシ」の表記は、炭素原子数がa~b個よりなる前記の意味であるアルキル-O-基を表わし、例えばメトキシ基、エトキシ基、n-プロピルオキシ基、i-プロピルオキシ基、n-ブチルオキシ基、i-ブチルオキシ基、s-ブチルオキシ基、tert-ブチルオキシ基、2-エチルへキシルオキシ基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。The notation "C a - C b alkoxy" represents an alkyl-O- group having the above meaning consisting of a to b carbon atoms, such as methoxy group, ethoxy group, n-propyloxy group, i- Specific examples include propyloxy group, n-butyloxy group, i-butyloxy group, s-butyloxy group, tert-butyloxy group, 2-ethylhexyloxy group, etc., and each group is selected within the specified number of carbon atoms. Ru.
「ハロ(Ca~Cb)アルコキシ」の表記は、炭素原子数がa~b個よりなる前記の意味であるハロアルキル-O-基を表わし、例えばジフルオロメトキシ基、トリフルオロメトキシ基、クロロジフルオロメトキシ基、ブロモジフルオロメトキシ基、2-フルオロエトキシ基、2-クロロエトキシ基、2,2,2-トリフルオロエトキシ基、1,1,2,2,-テトラフルオロエトキシ基、2-クロロ-1,1,2-トリフルオロエトキシ基、1,1,2,3,3,3-ヘキサフルオロプロピルオキシ基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。The notation "halo(C a -C b )alkoxy" represents a haloalkyl-O- group having the above meaning consisting of a to b carbon atoms, such as difluoromethoxy group, trifluoromethoxy group, chlorodifluoro Methoxy group, bromodifluoromethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2,-tetrafluoroethoxy group, 2-chloro-1 , 1,2-trifluoroethoxy group, 1,1,2,3,3,3-hexafluoropropyloxy group, etc., and the number of carbon atoms is selected within each specified range.
「Ca~Cbアルキルチオ」の表記は、炭素原子数がa~b個よりなる前記の意味であるアルキル-S-基を表わし、例えばメチルチオ基、エチルチオ基、n-プロピルチオ基、i-プロピルチオ基、n-ブチルチオ基、i-ブチルチオ基、s-ブチルチオ基、tert-ブチルチオ基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。The notation "C a - C b alkylthio" represents an alkyl-S- group having the above meaning having a to b carbon atoms, such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group. Specific examples include n-butylthio group, i-butylthio group, s-butylthio group, tert-butylthio group, etc., and are selected within the specified number of carbon atoms.
本明細書における「ハロ(Ca~Cb)アルキルチオ」の表記は、炭素原子数がa~b個よりなる前記の意味であるハロアルキル-S-基を表し、例えば、ジフルオロメチルチオ基、トリフルオロメチルチオ基、クロロジフルオロメチルチオ基、ブロモジフルオロメチルチオ基、2,2,2-トリフルオロエチルチオ基、1,1,2,2-テトラフルオロエチルチオ基、2-クロロ-1,1,2-トリフルオロエチルチオ基、ペンタフルオロエチルチオ基、1,1,2,3,3,3-ヘキサフルオロプロピルチオ基、ヘプタフルオロプロピルチオ基、1,2,2,2-テトラフルオロ-1-(トリフルオロメチル)エチルチオ基、ノナフルオロブチルチオ基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。In the present specification, the expression "halo(C a -C b )alkylthio" represents a haloalkyl-S- group having the above meaning consisting of a to b carbon atoms, such as difluoromethylthio group, trifluoromethylthio group, etc. Methylthio group, chlorodifluoromethylthio group, bromodifluoromethylthio group, 2,2,2-trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group, 2-chloro-1,1,2-tri Fluoroethylthio group, pentafluoroethylthio group, 1,1,2,3,3,3-hexafluoropropylthio group, heptafluoropropylthio group, 1,2,2,2-tetrafluoro-1-(trifluoropropylthio group) Specific examples include a fluoromethyl)ethylthio group and a nonafluorobutylthio group, which are selected within the specified number of carbon atoms.
「Ca~Cbアルキルスルフィニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるアルキル-S(O)-基を表わし、例えばメチルスルフィニル基、エチルスルフィニル基、n-プロピルスルフィニル基、i-プロピルスルフィニル基、n-ブチルスルフィニル基、i-ブチルスルフィニル基、s-ブチルスルフィニル基、tert-ブチルスルフィニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。The notation "C a -C b alkylsulfinyl" represents an alkyl-S(O)- group having the above meaning consisting of a to b carbon atoms, such as methylsulfinyl group, ethylsulfinyl group, n- Specific examples include propylsulfinyl group, i-propylsulfinyl group, n-butylsulfinyl group, i-butylsulfinyl group, s-butylsulfinyl group, tert-butylsulfinyl group, etc., and each specified range of the number of carbon atoms. is selected.
本明細書における「ハロ(Ca~Cb)アルキルスルフィニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるハロアルキル-S(O)-基を表し、例えば、ジフルオロメチルスルフィニル基、トリフルオロメチルスルフィニル基、クロロジフルオロメチルスルフィニル基、ブロモジフルオロメチルスルフィニル基、2,2,2-トリフルオロエチルスルフィニル基、1,2,2,2-テトラフルオロ-1-(トリフルオロメチル)エチルスルフィニル基、ノナフルオロブチルスルフィニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。In the present specification, the expression "halo(C a -C b )alkylsulfinyl" represents a haloalkyl-S(O)- group having the above meaning consisting of a to b carbon atoms, for example, difluoromethyl Sulfinyl group, trifluoromethylsulfinyl group, chlorodifluoromethylsulfinyl group, bromodifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 1,2,2,2-tetrafluoro-1-(trifluoromethyl ) Ethylsulfinyl group, nonafluorobutylsulfinyl group, etc. are listed as specific examples, and each is selected within the specified range of the number of carbon atoms.
「Ca~Cbアルキルスルホニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるアルキル-SO2-基を表わし、例えばメチルスルホニル基、エチルスルホニル基、n-プロピルスルホニル基、i-プロピルスルホニル基、n-ブチルスルホニル基、i-ブチルスルホニル基、s-ブチルスルホニル基、tert-ブチルスルホニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。The notation "C a -C b alkylsulfonyl" represents an alkyl-SO 2 - group having the above meaning consisting of a to b carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group. Specific examples include i-propylsulfonyl group, n-butylsulfonyl group, i-butylsulfonyl group, s-butylsulfonyl group, tert-butylsulfonyl group, etc., and each can be selected within the specified number of carbon atoms. be done.
本明細書における「ハロ(Ca~Cb)アルキルスルホニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるハロアルキル-SO2-基を表し、例えば、ジフルオロメチルスルホニル基、トリフルオロメチルスルホニル基、クロロジフルオロメチルスルホニル基、ブロモジフルオロメチルスルホニル基、2,2,2-トリフルオロエチルスルホニル基、1,1,2,2-テトラフルオロエチルスルホニル基、2-クロロ-1,1,2-トリフルオロエチルスルホニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。In the present specification, the expression "halo(C a -C b )alkylsulfonyl" represents a haloalkyl-SO 2 - group having the above meaning consisting of a to b carbon atoms, for example, a difluoromethylsulfonyl group. , trifluoromethylsulfonyl group, chlorodifluoromethylsulfonyl group, bromodifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 1,1,2,2-tetrafluoroethylsulfonyl group, 2-chloro-1 , 1,2-trifluoroethylsulfonyl groups, etc. are listed as specific examples, and the number of carbon atoms is selected within each specified range.
「Ca~Cbアルキルカルボニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるアルキル-C(O)-基を表わし、例えば、アセチル基、プロピオニル基、ブチリル基、イソブチリル基、バレリル基、イソバレリル基、2-メチルブタノイル基、ピバロイル基、ヘキサノイル基、ヘプタノイル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。The notation "C a -C b alkylcarbonyl" represents an alkyl-C(O)- group having the above meaning consisting of a to b carbon atoms, such as an acetyl group, a propionyl group, a butyryl group, Specific examples include isobutyryl group, valeryl group, isovaleryl group, 2-methylbutanoyl group, pivaloyl group, hexanoyl group, heptanoyl group, etc., and are selected within the specified number of carbon atoms.
「ハロ(Ca~Cb)アルキルカルボニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるハロアルキル-C(O)-基を表わし、例えば、フルオロアセチル基、クロロアセチル基、ジフルオロアセチル基、ジクロロアセチル基、トリフルオロアセチル基、クロロジフルオロアセチル基、ブロモジフルオロアセチル基、トリクロロアセチル基、ペンタフルオロプロピオニル基、ヘプタフルオロブタノイル基、3-クロロ-2,2-ジメチルプロパノイル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。The notation "halo(C a -C b )alkylcarbonyl" represents a haloalkyl-C(O)- group having the above meaning consisting of a to b carbon atoms, such as fluoroacetyl group, chloroacetyl group, etc. group, difluoroacetyl group, dichloroacetyl group, trifluoroacetyl group, chlorodifluoroacetyl group, bromodifluoroacetyl group, trichloroacetyl group, pentafluoropropionyl group, heptafluorobutanoyl group, 3-chloro-2,2-dimethylpropyl group Specific examples include a noyl group, which is selected within each specified range of carbon atoms.
「Ca~Cbアルコキシカルボニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるアルキル-O-C(O)-基を表わし、例えばメトキシカルボニル基、エトキシカルボニル基、n-プロピルオキシカルボニル基、i-プロピルオキシカルボニル基、n-ブトキシカルボニル基、i-ブトキシカルボニル基、s-ブトキシカルボニル基、tert-ブトキシカルボニル基、2-エチルへキシルオキシカルボニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。The notation "C a -C b alkoxycarbonyl" represents an alkyl-O-C(O)- group having the above meaning consisting of a to b carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, Specific examples include n-propyloxycarbonyl group, i-propyloxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, s-butoxycarbonyl group, tert-butoxycarbonyl group, 2-ethylhexyloxycarbonyl group, etc. and are selected within each specified number of carbon atoms.
「ハロ(Ca~Cb)アルコキシカルボニル」の表記は、炭素原子数がa~b個よりなる前記の意味であるハロアルキル-O-C(O)-基を表わし、例えば、クロロメトキシカルボニル基、2-クロロエトキシカルボニル基、2,2-ジフルオロエトキシカルボニル基、2,2,2,-トリフルオロエトキシカルボニル基、2,2,2,-トリクロロエトキシカルボニル基等が具体例として挙げられ、各々の指定の炭素原子数の範囲で選択される。The notation "halo(C a -C b )alkoxycarbonyl" represents a haloalkyl-O-C(O)- group having the above meaning consisting of a to b carbon atoms, for example, a chloromethoxycarbonyl group. , 2-chloroethoxycarbonyl group, 2,2-difluoroethoxycarbonyl group, 2,2,2,-trifluoroethoxycarbonyl group, 2,2,2,-trichloroethoxycarbonyl group, etc. is selected within the specified number of carbon atoms.
「Uによって置換された(Ca~Cb)シクロアルキル」の表記は、炭素原子に結合した水素原子が任意の数のUによって置換された、炭素原子数がa~b個よりなる前記の意味であるシクロアルキル基を表わし、各々の指定の炭素原子数の範囲で選択される。このとき、それぞれの(Ca~Cb)シクロアルキル基上の置換基Uが2個以上存在するとき、それぞれのUは互いに同一でも異なってもよい。The notation "cycloalkyl (C a -C b ) substituted by U" refers to the above-mentioned cycloalkyl having a to b carbon atoms, in which the hydrogen atoms bonded to the carbon atoms are replaced by any number of U. represents a cycloalkyl group with a meaning, selected within each specified range of carbon atoms. At this time, when there are two or more substituents U on each (C a -C b ) cycloalkyl group, each U may be the same or different from each other.
本発明の式(1)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、好ましくは、G1は、G1-1であり、R1、R2、R3及びR4は、各々独立して、水素原子、ハロゲン原子、ハロ(C1~C6)アルキル、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル、ハロ(C1~C6)アルキルスルホニルであり、RAは、C1~C3アルコキシ、ハロ(C1~C3)アルコキシ、C1~C3アルキルチオ、ハロ(C1~C3)アルキルチオ、C1~C3アルキルスルホニル、ハロ(C1~C3)アルキルスルホニル、1H-ピラゾール-1-イル、2H-1,2,3-トリアゾール-2-イルであり、A1は、C-RC又はNであり、A2は、C-RE又はNであり、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルコキシ、C1~C6アルキルチオ、C1~C6アルキルスルフィニル、C1~C6アルキルスルホニル、各々独立して5個までのZで置換されても良いフェニル、V-2、V-4、V-5、V-6であり、Dは水素原子、C1~C3アルキル、ハロ(C1~C3)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C3アルキルスルホニル、ハロ(C1~C3)アルキルスルホニル、C1~C3アルキルオキシカルボニル、ハロ(C1~C3)アルキルオキシカルボニル、各々独立して5個までのTで置換されても良いベンゼンカルボニルであり、Tは水素原子、ハロゲン原子、C1~C3アルキル、ハロ(C1~C3)アルキル、C1~C3アルコキシ、ハロ(C1~C3)アルコキシであり、Eは、水素原子、C1~C6アルキル、シクロプロピルメチル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、メトキシメチル、エトキシメチル、シアノメチル、シアノエチル、メチルチオメチル、メチルスルホニルメチルである。In the compound represented by formula (1) or its salt or its N-oxide of the present invention, preferably G 1 is G 1 -1, and R 1 , R 2 , R 3 and R 4 are Each independently represents a hydrogen atom, a halogen atom, halo(C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 ) alkylsulfonyl, and R A is C 1 -C 3 alkoxy, halo(C 1 -C 3 )alkoxy, C 1 -C 3 alkylthio, halo(C 1 -C 3 )alkylthio, C 1 -C 3 alkylsulfonyl , halo(C 1 -C 3 )alkylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, A 1 is CR C or N, A 2 is C-R E or N (where either A 1 or A 2 is N and the other is C-R C or C-R E ), R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, phenyl, V-2, V-4, V-5, and V-6, each of which may be independently substituted with up to 5 Z; D is a hydrogen atom, C 1 -C 3 alkyl, halo (C 1 - C3 ) alkyl, C1 - C6 alkylcarbonyl, C3 - C6 cycloalkylcarbonyl, halo(C1- C6 ) alkylcarbonyl, C1 - C3 alkylsulfonyl, halo( C1 -C3 ) ) alkylsulfonyl, C 1 -C 3 alkyloxycarbonyl, halo(C 1 -C 3 )alkyloxycarbonyl, benzenecarbonyl which may each be independently substituted with up to 5 T, where T is a hydrogen atom, Halogen atom, C 1 -C 3 alkyl, halo(C 1 -C 3 )alkyl, C 1 -C 3 alkoxy, halo(C 1 -C 3 )alkoxy, and E is a hydrogen atom, C 1 -C 6 Alkyl, cyclopropylmethyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkyl Sulfonyl, halo(C 1 -C 6 )alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl.
本発明の式(1)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、より好ましくは、G1は、G1-1であり、R1、R2、R3及びR4は水素原子、ハロ(C1~C3)アルキルであり、RAは、エチルチオ、エチルスルホニル、1H-ピラゾール-1-イル、2H-1,2,3-トリアゾール-2-イルであり、A1は、C-RCであり、A2は、Nであり、RB、RDは、水素原子であり、RCは各々独立して2個までのZで置換されても良いフェニル、1H-ピラゾール-1-イル、2H-1,2,3-トリアゾール-2-イルであり、Zは、水素、フッ素、塩素、トリフルオロメチル、トリフルオロメトキシであり、Dは水素原子、アセチルであり、Eは、水素原子、C1~C3アルキル、シクロプロピルメチル、ハロ(C1~C3)アルキル、メトキシメチル、エトキシメチル、シアノメチル、シアノエチル、メチルチオメチル、メチルスルホニルメチルである。In the compound represented by formula (1) of the present invention, its salt or its N-oxide, more preferably G 1 is G 1 -1, and R 1 , R 2 , R 3 and R 4 are hydrogen atom, halo(C 1 -C 3 )alkyl, R A is ethylthio, ethylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, A 1 is C-R C , A 2 is N, R B and R D are hydrogen atoms, and R C is phenyl, which may be independently substituted with up to two Z, 1H -pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy, D is a hydrogen atom, acetyl , E is a hydrogen atom, C 1 -C 3 alkyl, cyclopropylmethyl, halo(C 1 -C 3 )alkyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl.
本発明の式(1)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、より好ましくは、G1は、G1-1であり、R1、R2、R3及びR4は水素原子、ハロ(C1~C3)アルキルであり、RAは、エチルチオ、エチルスルホニル、1H-ピラゾール-1-イル、2H-1,2,3-トリアゾール-2-イルであり、A2は、C-REであり、A1は、Nであり、RB、RDは、水素原子であり、RCは各々独立して2個までのZで置換されても良いフェニル、1H-ピラゾール-1-イル、2H-1,2,3-トリアゾール-2-イルであり、Zは、水素、フッ素、塩素、トリフルオロメチル、トリフルオロメトキシであり、Dは水素原子、アセチルであり、Eは、水素原子、C1~C3アルキル、シクロプロピルメチル、ハロ(C1~C3)アルキル、メトキシメチル、エトキシメチル、シアノメチル、シアノエチル、メチルチオメチル、メチルスルホニルメチルである。In the compound represented by formula (1) of the present invention, its salt or its N-oxide, more preferably G 1 is G 1 -1, and R 1 , R 2 , R 3 and R 4 are hydrogen atom, halo(C 1 -C 3 )alkyl, R A is ethylthio, ethylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, A 2 is C-R E , A 1 is N, R B and R D are hydrogen atoms, and R C is phenyl, which may be independently substituted with up to two Z, 1H -pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy, D is a hydrogen atom, acetyl , E is a hydrogen atom, C 1 -C 3 alkyl, cyclopropylmethyl, halo(C 1 -C 3 )alkyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl.
本発明の式(1)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、さらに好ましくは、RAは、エチルチオ、エチルスルホニルである。More preferably, in the compound represented by formula (1) of the present invention, a salt thereof, or an N-oxide thereof, R A is ethylthio or ethylsulfonyl.
本発明の式(1)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、特に好ましくは、
3-(エチルスルホニル)-5-(1H-ピラゾール-1-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号91)、
3-(エチルスルホニル)-5-(1H-ピラゾール-1-イル)-N-(4-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号100)、
N-((3-(エチルスルホニル)-5-(1H-ピラゾール-1-イル)ピリジン-2-イル)((4-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号101)、
3-(エチルスルホニル)-5-(2H-1,2,3-トリアゾール-2-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号103)、
3-(エチルスルホニル)-5-(1H-1,2,4-トリアゾール-1-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号105)、
N-((3-(エチルスルホニル)-5-(2H-1,2,3-トリアゾール-2-イル)ピリジン-2-イル)((5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号106)、
N-((3-(エチルスルホニル)-5-(1H-ピラゾール-1-イル)ピリジン-2-イル)((5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号108)、
3-(エチルスルホニル)-5-(1H-ピラゾール-1-イル)-N-(6-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号109)、
N-((3-(エチルスルホニル)-5-(1H-ピラゾール-1-イル)ピリジン-2-イル)((6-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号110)、
N-((3-(エチルスルホニル)-5-(1H-ピラゾール-1-イル)ピリジン-2-イル)((5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)-2,2,2-トリフルオロアセタミド(化合物番号111)、
3-(エチルスルホニル)-5-(1H-1,2,3-トリアゾール-1-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号120)、
5-(ジメチルアミノ)-3-(エチルスルホニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号125)、
3-(エチルスルホニル)-5-フェニル-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号127)、
5-(4-クロロメチル)-3-(エチルスルホニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号131)、
5-(3,5-ジクロロフェニル)-3-(エチルスルホニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号133)、
3-(エチルスルホニル)-5-(3-(トリフルオロメチル)フェニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号137)、
3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号139)、
N-((3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)ピリジン-2-イル)((5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号140)、
3-(エチルスルホニル)-5-(4-(トリフルオロメトキシ)フェニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号142)、
5-(2,4-ビス(トリフルオロメチル)フェニル)-3-(エチルスルホニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号144)、
5-(3,5-ビス(トリフルオロメチル)フェニル)-3-(エチルスルホニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号146)、
N-((3-(エチルスルホニル)-5-(1H-ピラゾール-1-イル)ピリジン-2-イル)(メチル(5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号199)、
3-(エチルスルホニル)-5-(3-(トリフルオロメトキシ)フェニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号200)、
N-((3-(エチルスルホニル)-5-(4-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)(メチル(5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号204)、
N-((3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)ピリジン-2-イル)(メチル(5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号205)、
N-((3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)ピリジン-2-イル)((メトキシメチル)(5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号207)、
N-((3-(エチルスルホニル)-5-(4-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)((メトキシメチル)(5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号209)、
N-(((エトキシメチル)(5-(トリフルオロメチル)ピリジン-2-イル)アミノ)(3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)ピリジン-2-イル)メチレン)アセタミド(化合物番号211)、
N-(((シアノメチル)(5-(トリフルオロメチル)ピリジン-2-イル)アミノ)(3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)ピリジン-2-イル)メチレン)アセタミド(化合物番号213)、
N-((3-(エチルスルホニル)-5-(4-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)((5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号220)、
N-((エチル(5-(トリフルオロメチル)ピリジン-2-イル)アミノ)(3-(エチルスルホニル)-5-(4-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)メチレン)アセタミド、
N-((3-(エチルスルホニル)-5-(4-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)(プロピル(5-(トリフルオロメトキシ)ピリジン-2-イル)アミノ)メチレン)アセタミド、
N-(((2-シアノエチル)(5-(トリフルオロメチル)ピリジン-2-イル)アミノ)(3-(エチルスルホニル)-5-(4-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)メチレン)アセタミド、
N-((3-(エチルスルホニル)-5-(4-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)(((メチルスルホニル)メチル)(5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド、
である。Among the compounds represented by formula (1) of the present invention, salts thereof, or N-oxides thereof, particularly preferably:
3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 91),
3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 100),
N-((3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)((4-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 101),
3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 103),
3-(ethylsulfonyl)-5-(1H-1,2,4-triazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 105),
N-((3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)((5-(trifluoromethyl)pyridin-2-yl)amino ) methylene) acetamide (compound number 106),
N-((3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 108),
3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)-N-(6-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 109),
N-((3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)((6-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (compound number 110),
N-((3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)-2, 2,2-trifluoroacetamide (compound number 111),
3-(ethylsulfonyl)-5-(1H-1,2,3-triazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 120),
5-(dimethylamino)-3-(ethylsulfonyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 125),
3-(ethylsulfonyl)-5-phenyl-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 127),
5-(4-chloromethyl)-3-(ethylsulfonyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 131),
5-(3,5-dichlorophenyl)-3-(ethylsulfonyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 133),
3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 137),
3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 139),
N-((3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide( Compound number 140),
3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 142),
5-(2,4-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 144),
5-(3,5-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 146),
N-((3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)(methyl(5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide( Compound number 199),
3-(ethylsulfonyl)-5-(3-(trifluoromethoxy)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (compound number 200),
N-((3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)(methyl(5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (Compound No. 204),
N-((3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)(methyl(5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide (Compound No. 205),
N-((3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)((methoxymethyl)(5-(trifluoromethyl)pyridin-2-yl)amino) methylene) acetamide (compound number 207),
N-((3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)((methoxymethyl)(5-(trifluoromethyl)pyridin-2-yl)amino) methylene) acetamide (compound number 209),
N-(((ethoxymethyl)(5-(trifluoromethyl)pyridin-2-yl)amino)(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl) methylene) acetamide (compound number 211),
N-(((cyanomethyl)(5-(trifluoromethyl)pyridin-2-yl)amino)(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)methylene ) acetamide (compound number 213),
N-((3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide( Compound number 220),
N-((ethyl(5-(trifluoromethyl)pyridin-2-yl)amino)(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)methylene)acetamide ,
N-((3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)(propyl(5-(trifluoromethoxy)pyridin-2-yl)amino)methylene)acetamide ,
N-(((2-cyanoethyl)(5-(trifluoromethyl)pyridin-2-yl)amino)(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl ) methylene) acetamide,
N-((3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)(((methylsulfonyl)methyl)(5-(trifluoromethyl)pyridin-2-yl) ) amino) methylene) acetamide,
It is.
本発明の式(2)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、好ましくは、G2は、G2-1であり、R1、R2、R3及びR4は、各々独立して、水素原子、ハロゲン原子、ハロ(C1~C6)アルキル、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル、ハロ(C1~C6)アルキルスルホニルであり、RAは、C1~C3アルコキシ、ハロ(C1~C3)アルコキシ、C1~C3アルキルチオ、ハロ(C1~C3)アルキルチオ、C1~C3アルキルスルホニル、ハロ(C1~C3)アルキルスルホニル、1H-ピラゾール-1-イル、2H-1,2,3-トリアゾール-2-イルであり、A1は、C-RC又はNであり、A2は、C-RE又はNであり、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルコキシ、C1~C6アルキルチオ、、C1~C6アルキルスルフィニル、C1~C6アルキルスルホニル、各々独立して5個までのZで置換されても良いフェニル、V-2、V-4、V-5、V-6である。In the compound represented by formula (2) or its salt or its N-oxide of the present invention, preferably G 2 is G 2 -1, and R 1 , R 2 , R 3 and R 4 are Each independently represents a hydrogen atom, a halogen atom, halo(C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 ) alkylsulfonyl, and R A is C 1 -C 3 alkoxy, halo(C 1 -C 3 )alkoxy, C 1 -C 3 alkylthio, halo(C 1 -C 3 )alkylthio, C 1 -C 3 alkylsulfonyl , halo(C 1 -C 3 )alkylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, A 1 is CR C or N, A 2 is C-R E or N (where either A 1 or A 2 is N and the other is C-R C or C-R E ), R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl , phenyl, V-2, V-4, V-5, V-6, each of which may be independently substituted with up to five Zs.
本発明の式(2)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、より好ましくは、G2は、G2-1であり、R1、R2、R3及びR4は水素原子、ハロ(C1~C3)アルキルであり、RAは、エチルチオ、エチルスルホニル、1H-ピラゾール-1-イル、2H-1,2,3-トリアゾール-2-イルであり、A1は、C-RCであり、A2は、Nであり、RB及びRDは、水素原子であり、RCは各々独立して2個までのZで置換されても良いフェニル、1H-ピラゾール-1-イル、2H-1,2,3-トリアゾール-2-イル、ジメチルアミノであり、Zは、水素、フッ素、塩素、トリフルオロメチル、トリフルオロメトキシである。In the compound represented by formula (2) or its salt or its N-oxide of the present invention, more preferably G 2 is G 2 -1, and R 1 , R 2 , R 3 and R 4 are hydrogen atom, halo(C 1 -C 3 )alkyl, R A is ethylthio, ethylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, A 1 is C-R C , A 2 is N, R B and R D are hydrogen atoms, each R C is phenyl which may be independently substituted with up to two Z, 1H -pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, dimethylamino, and Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy.
本発明の式(2)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、さらに好ましくは、RAは、エチルチオ、エチルスルホニルである。In the compound represented by formula (2) of the present invention, a salt thereof, or an N-oxide thereof, R A is more preferably ethylthio or ethylsulfonyl.
本発明の式(2)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、特に好ましくは、
2-(3-(1H-ピラゾール-1-イル)ピリジン-4-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号46)、
2-(3-(2H-1,2,3-トリアゾロ-2イル)ピリジン-4-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号48)、
2-(3-(2H-1,2,3-トリアゾロ-2-イル)ピリジン-4-イル)-7-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号170)、
5-(エチルスルホニル)-N,N-ジメチル-6-(6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン-2-イル)ピリジン-3-アミン(化合物番号173)、
2-(3-(エチルスルホニル)-5-(2-(トリフルオロメチル)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号174)、
2-(3-(エチルスルホニル)-5-(3-(トリフルオロメチル)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号175)、
2-(3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号176)、
2-(5-(2,4-ビス(トリフルオロメチル)フェニル)-3-(エチルスルホニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン、
2-(3-(エチルスルホニル)-5-(2-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン、
2-(3-(エチルスルホニル)-5-(3-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号214)、
2-(3-(エチルスルホニル)-5-(4-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号177)、
2-(5-(3,5-ビス(トリフルオロメチル)フェニル)-3-(エチルスルホニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号178)、
2-(3-(エチルスルホニル)-5-(ピリミジン-5-イル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号179)、
2-(3-(エチルスルホニル)-5-(1H-ピラゾール-1-イル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号180)、
2-(3-(エチルスルホニル)-5-(2H-1,2,3-トリアゾール-2-イル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号181)
である。Among the compounds represented by formula (2) of the present invention, salts thereof, or N-oxides thereof, particularly preferably:
2-(3-(1H-pyrazol-1-yl)pyridin-4-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 46) ,
2-(3-(2H-1,2,3-triazolo-2yl)pyridin-4-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 48),
2-(3-(2H-1,2,3-triazolo-2-yl)pyridin-4-yl)-7-(trifluoromethyl)-[1,2,4]triazolo[1,5-a] Pyridine (compound number 170),
5-(ethylsulfonyl)-N,N-dimethyl-6-(6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl)pyridin-3-amine (Compound No. 173),
2-(3-(ethylsulfonyl)-5-(2-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 174),
2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 175),
2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 176),
2-(5-(2,4-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1 ,5-a]pyridine,
2-(3-(ethylsulfonyl)-5-(2-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine,
2-(3-(ethylsulfonyl)-5-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 214),
2-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 177),
2-(5-(3,5-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1 ,5-a]pyridine (compound number 178),
2-(3-(ethylsulfonyl)-5-(pyrimidin-5-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 179),
2-(3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a ] Pyridine (compound number 180),
2-(3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo [1,5-a]pyridine (compound number 181)
It is.
本発明の式(2)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、最も好ましくは、
2-(3-(エチルスルホニル)-5-(2-(トリフルオロメチル)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号174)、
2-(3-(エチルスルホニル)-5-(3-(トリフルオロメチル)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号175)、
2-(3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号176)、
2-(5-(2,4-ビス(トリフルオロメチル)フェニル)-3-(エチルスルホニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン、
2-(3-(エチルスルホニル)-5-(2-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン、
2-(3-(エチルスルホニル)-5-(3-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号214)、
2-(3-(エチルスルホニル)-5-(4-(トリフルオロメトキシ)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号177)、
2-(5-(3,5-ビス(トリフルオロメチル)フェニル)-3-(エチルスルホニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号178)、
2-(3-(エチルスルホニル)-5-(1H-ピラゾール-1-イル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号180)、
2-(3-(エチルスルホニル)-5-(2H-1,2,3-トリアゾール-2-イル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号181)
である。Among the compounds represented by formula (2) of the present invention, salts thereof, or N-oxides thereof, most preferably:
2-(3-(ethylsulfonyl)-5-(2-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 174),
2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 175),
2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 176),
2-(5-(2,4-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1 ,5-a]pyridine,
2-(3-(ethylsulfonyl)-5-(2-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine,
2-(3-(ethylsulfonyl)-5-(3-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 214),
2-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxy)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5- a] pyridine (compound number 177),
2-(5-(3,5-bis(trifluoromethyl)phenyl)-3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1 ,5-a]pyridine (compound number 178),
2-(3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a ] Pyridine (compound number 180),
2-(3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo [1,5-a]pyridine (compound number 181)
It is.
本発明の式(3)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、好ましくは、G2は、G2-1であり、R1、R2、R3及びR4は、各々独立して、水素原子、ハロゲン原子、ハロ(C1~C6)アルキル、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル、ハロ(C1~C6)アルキルスルホニルであり、RAは、C1~C3アルコキシ、ハロ(C1~C3)アルコキシ、C1~C3アルキルチオ、ハロ(C1~C3)アルキルチオ、C1~C3アルキルスルホニル、ハロ(C1~C3)アルキルスルホニル、1H-ピラゾール-1-イル、2H-1,2,3-トリアゾール-2-イルであり、A1は、C-RC又はNであり、A2は、C-RE又はNであり、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルコキシ、C1~C6アルキルチオ、C1~C6アルキルスルフィニル、C1~C6アルキルスルホニル、各々独立して5個までのZで置換されても良いフェニル、V-2、V-4、V-5、V-6である。In the compound represented by formula (3) of the present invention, a salt thereof, or an N-oxide thereof, preferably G 2 is G 2 -1, and R 1 , R 2 , R 3 and R 4 are Each independently represents a hydrogen atom, a halogen atom, halo(C 1 -C 6 )alkyl, halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 ) alkylsulfonyl, and R A is C 1 -C 3 alkoxy, halo(C 1 -C 3 )alkoxy, C 1 -C 3 alkylthio, halo(C 1 -C 3 )alkylthio, C 1 -C 3 alkylsulfonyl , halo(C 1 -C 3 )alkylsulfonyl, 1H-pyrazol-1-yl, 2H-1,2,3-triazol-2-yl, A 1 is CR C or N, A 2 is C-R E or N (where either A 1 or A 2 is N and the other is C-R C or C-R E ), R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, phenyl, V-2, V-4, V-5, V-6, each of which may be independently substituted with up to 5 Zs;
本発明の式(3)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、より好ましくは、G2は、G2-1であり、R1、R2、R3及びR4は水素原子、ハロ(C1~C3)アルキルであり、RAは、C1~C3アルキルチオ、C1~C3アルキルスルホニルであり、A1は、C-RCであり、A2は、Nであり、RB及びRDは、水素原子であり、RCは各々独立して2個までのZで置換されても良いフェニル、1H-ピラゾール-1-イル、2H-1,2,3-トリアゾール-2-イルであり、Zは、水素、フッ素、塩素、トリフルオロメチル、トリフルオロメトキシである。In the compound represented by formula (3) or its salt or its N-oxide of the present invention, more preferably G 2 is G 2 -1, and R 1 , R 2 , R 3 and R 4 are hydrogen atom, halo(C 1 -C 3 )alkyl, R A is C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfonyl, A 1 is CR C , A 2 is , N, R B and R D are hydrogen atoms, and R C is phenyl, 1H-pyrazol-1-yl, 2H-1,2, which may each be independently substituted with up to two Zs. ,3-triazol-2-yl, and Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy.
本発明の式(3)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、より好ましくは、G2は、G2-1であり、R1、R2、R3及びR4は水素原子、ハロ(C1~C3)アルキルであり、RAは、C1~C3アルキルチオ、C1~C3アルキルスルホニルであり、A2は、C-REであり、A1は、Nであり、RB及びRDは、水素原子であり、RCは各々独立して2個までのZで置換されても良いフェニル、1H-ピラゾール-1-イル、2H-1,2,3-トリアゾール-2-イルであり、Zは、水素、フッ素、塩素、トリフルオロメチル、トリフルオロメトキシである。In the compound represented by formula (3) or its salt or its N-oxide of the present invention, more preferably G 2 is G 2 -1, and R 1 , R 2 , R 3 and R 4 are hydrogen atom, halo(C 1 -C 3 )alkyl, R A is C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfonyl, A 2 is CR E , A 1 is , N, R B and R D are hydrogen atoms, and R C is phenyl, 1H-pyrazol-1-yl, 2H-1,2, which may each be independently substituted with up to two Zs. ,3-triazol-2-yl, and Z is hydrogen, fluorine, chlorine, trifluoromethyl, trifluoromethoxy.
本発明の式(3)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、さらに好ましくは、RAは、エチルチオ、エチルスルホニルである。In the compound represented by formula (3) of the present invention, a salt thereof, or an N-oxide thereof, R A is more preferably ethylthio or ethylsulfonyl.
本発明の式(3)で表される化合物若しくはその塩類又はそれらのN-オキシドにおいて、さらに好ましくは、
2-(3-(エチルスルホニル)-5-(1H-ピラゾール-1-イル)ピリジン-2-イル)-7-(トリフルオロメチル)-4H-ピリド[1,2-a][1,3,5]トリアジン-4-オン(化合物番号193)
2-(3-(エチルスルホニル)-5-(2H-1,2,3-トリアゾール-2-イル)ピリジン-2-イル)-7-(トリフルオロメチル)-4H-ピリド[1,2-a][1,3,5]トリアジン-4-オン(化合物番号215)、
2-(3-(エチルスルホニル)-5-(3-(トリフルオロメチル)フェニル)ピリジン-2-イル)-7-(トリフルオロメチル)-4H-ピリド[1,2-a][1,3,5]トリアジン-4-オン(化合物番号216)、
2-(3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)ピリジン-2-イル)-7-(トリフルオロメチル)-4H-ピリド[1,2-a][1,3,5]トリアジン-4-オン(化合物番号217)、
2-(3-(エチルスルホニル)-5-(3-(トリフルオロメチル)フェニル)ピリジン-2-イル)-7-(トリフルオロメチル)-4H-ピリド[1,2-a][1,3,5]トリアジン-4-オン(化合物番号218)、
2-(3-(エチルスルホニル)-5-(4-(トリフルオロメトキシトリフルオロメトキシトリフルオロメトキシ)フェニル)ピリジン-2-イル)-7-(トリフルオロメチル)-4H-ピリド[1,2-a][1,3,5]トリアジン-4-オン(化合物番号219)、
である。More preferably, in the compound represented by formula (3) or its salt or its N-oxide of the present invention,
2-(3-(ethylsulfonyl)-5-(1H-pyrazol-1-yl)pyridin-2-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1,3 ,5] triazin-4-one (compound number 193)
2-(3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-7-(trifluoromethyl)-4H-pyrido[1,2- a][1,3,5]triazin-4-one (compound number 215),
2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1, 3,5] triazin-4-one (compound number 216),
2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1, 3,5] triazin-4-one (compound number 217),
2-(3-(ethylsulfonyl)-5-(3-(trifluoromethyl)phenyl)pyridin-2-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1, 3,5] triazin-4-one (compound number 218),
2-(3-(ethylsulfonyl)-5-(4-(trifluoromethoxytrifluoromethoxytrifluoromethoxy)phenyl)pyridin-2-yl)-7-(trifluoromethyl)-4H-pyrido[1,2 -a][1,3,5]triazin-4-one (compound number 219),
It is.
本発明の式(1)、式(2)、又は式(3)で表される化合物若しくはその塩又はそれらのN-オキシド(以下、本発明の化合物ともいう)は、例えば下記製造方法によって製造することができるが、本発明はこれらに限定されるものではない。 The compound represented by formula (1), formula (2), or formula (3) of the present invention, a salt thereof, or an N-oxide thereof (hereinafter also referred to as the compound of the present invention) can be produced, for example, by the following production method. However, the present invention is not limited thereto.
<製造方法1>
{式中、RA、RB、RD、A1、A2及びG1は前記と同じであることを示す。}<Manufacturing method 1>
{In the formula, R A , R B , R D , A 1 , A 2 and G 1 are the same as above. }
工程a
式(4)で表されるアミン化合物と式(5)で表されるシアノ化合物とを、塩基及び不活性溶媒の存在下、反応させることにより式(1-1)で表されるアミジン化合物を製造することができる。本反応は文献記載の方法(Journal of Organic Chemistry, 2014, 79(10), p. 4687-4693)に準じて行うことができる。Process a
An amidine compound represented by formula (1-1) is produced by reacting an amine compound represented by formula (4) with a cyano compound represented by formula (5) in the presence of a base and an inert solvent. can be manufactured. This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry, 2014, 79(10), p. 4687-4693).
本反応で使用できる塩基としては、例えば、水素化リチウム、水素化ナトリウム、水素化カリウム、水素化カルシウム等の水素化アルカリ金属、ノルマルブチルリチウム、ナトリウムビス(トリメチルシリル)アミド、リチウムビス(トリメチルシリル)アミド、カリウムビス(トリメチルシリル)アミド、リチウムジイソプロピルアミン等が挙げられるが、本反応で使用できる反応剤はこれに限らない。塩基の使用量は式(4)で表される化合物に対して通常約1倍モル~3倍モルの範囲で使用される。 Examples of bases that can be used in this reaction include alkali metal hydrides such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride, n-butyllithium, sodium bis(trimethylsilyl)amide, and lithium bis(trimethylsilyl)amide. , potassium bis(trimethylsilyl)amide, lithium diisopropylamine, etc., but the reactants that can be used in this reaction are not limited to these. The amount of the base to be used is usually about 1 to 3 times the mole of the compound represented by formula (4).
本反応で使用できる不活性溶媒としては、本反応を著しく阻害しないものであれば良く、例えば、ジエチルエーテル、テトラヒドロフラン、ジオキサン等の鎖状又は環状エーテル類;ベンゼン、トルエン、キシレン等の芳香族炭化水素類;N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、ジメチルスルホキシド、1,3-ジメチル-2-イミダゾリノン等の極性溶媒を挙げることができ、これらの不活性溶媒は単独で又は2種以上混合して使用することができる。 Inert solvents that can be used in this reaction may be those that do not significantly inhibit this reaction, such as chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic carbonized solvents such as benzene, toluene, and xylene. Hydrogen; Polar solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone can be mentioned, and these inert solvents can be used alone or in combination with two Can be used in combination of more than one species.
本反応における反応温度は通常-78℃から使用する溶媒の沸点の範囲で行えばよく、反応時間は反応規模、反応温度等により一定しないが、数分~48時間の範囲で適宜選択すれば良い。式(5)で表されるシアノ化合物は式(4)で表されるアミノ化合物に対して通常約1/3倍モル~1倍モル又は約1倍モル~3倍モルの範囲で使用される。また本反応は、例えば窒素ガスやアルゴンガスのような不活性ガスの雰囲気下で行うこともできる。反応終了後、目的物を含む反応系から常法により目的物を単離すれば良く、必要に応じて再結晶、カラムクロマトグラフィー等で精製することにより目的物を製造することができる。 The reaction temperature in this reaction is usually within the range of -78°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be selected appropriately within the range of several minutes to 48 hours. . The cyano compound represented by the formula (5) is usually used in an amount of about 1/3 to 1 times the mole or about 1 to 3 times the mole of the amino compound represented by the formula (4). . Further, this reaction can also be carried out, for example, in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
工程aの別法
式(4)で表されるアミン化合物と式(5)で表されるシアノ化合物とを、ルイス酸の存在下、反応させることにより式(1-1)で表されるアミジン化合物を製造することができる。本反応は文献記載の方法(J.Med.Chem. 2002, 45, 21, 4655-4668)に準じて行うことができる。Alternative method for step a Amidine represented by formula (1-1) is produced by reacting an amine compound represented by formula (4) with a cyano compound represented by formula (5) in the presence of a Lewis acid. Compounds can be manufactured. This reaction can be carried out according to the method described in the literature (J.Med.Chem. 2002, 45, 21, 4655-4668).
本反応で使用できるルイス酸としては、例えば、トリメチルアルミニウム、塩化アルミニウム、四塩化チタン等が挙げられるが、本反応で使用できる反応剤はこれに限らない。ルイス酸の使用量は式(4)で表される化合物に対して通常約1倍モル~3倍モルの範囲で使用される。 Examples of Lewis acids that can be used in this reaction include trimethylaluminum, aluminum chloride, and titanium tetrachloride, but the reactants that can be used in this reaction are not limited to these. The amount of Lewis acid to be used is generally about 1 to 3 times the mole of the compound represented by formula (4).
本反応で使用できる不活性溶媒としては、本反応を著しく阻害しないものであれば良く、例えば、ベンゼン、トルエン、キシレン等の芳香族炭化水素類;ジクロロメタン、1,2-ジクロロエタン等のハロゲン化溶剤挙げることができ、これらの不活性溶媒は単独で又は2種以上混合して使用することができる。 Inert solvents that can be used in this reaction may be those that do not significantly inhibit this reaction, such as aromatic hydrocarbons such as benzene, toluene, and xylene; halogenated solvents such as dichloromethane and 1,2-dichloroethane. These inert solvents can be used alone or in combination of two or more.
本反応における反応温度は通常0℃から使用する溶媒の沸点の範囲で行えばよく、反応時間は反応規模、反応温度等により一定しないが、数分~48時間の範囲で適宜選択すれば良い。式(5)で表されるシアノ化合物は式(4)で表されるアミノ化合物に対して通常約1倍モル~3倍モルの範囲で使用される。また本反応は、例えば窒素ガスやアルゴンガスのような不活性ガスの雰囲気下で行うこともできる。反応終了後、目的物を含む反応系から常法により目的物を単離すれば良く、必要に応じて再結晶、カラムクロマトグラフィー等で精製することにより目的物を製造することができる。 The reaction temperature in this reaction is usually carried out in the range of 0° C. to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be appropriately selected in the range of several minutes to 48 hours. The cyano compound represented by formula (5) is usually used in an amount of about 1 to 3 times the molar amount of the amino compound represented by formula (4). Further, this reaction can also be carried out, for example, in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
工程b
Dが水素原子ではない場合、式(1-1)で表されるアミジン化合物を、場合により塩基及び不活性溶媒の存在下、反応剤と反応させることにより式(1-2)で表されるアミジン化合物を製造することができる。
{式中、RA、RB、RD、A1、A2、G1及びDは前記と同じであることを示す。}Process b
When D is not a hydrogen atom, the amidine compound represented by formula (1-1) is reacted with a reactant, optionally in the presence of a base and an inert solvent, to form a compound represented by formula (1-2). Amidine compounds can be produced.
{In the formula, R A , R B , R D , A 1 , A 2 , G 1 and D are the same as above. }
本発明で使用できる反応剤としては、例えば、塩化アセチル、塩化トリフルオロアセチル、クロロ炭酸メチル、メタンスルホン酸塩化物、トリフルオロメタンスルホン酸塩化物等の酸塩化物、無水酢酸、無水トリフルオロ酢酸、無水トリフルオロスルホン酸等の酸無水物;ヨウ化メチル、ヨウ化エチル、1,1,1-トリフルオロ-2-ヨードエタン、硫酸ジメチル等のアルキル化剤等が挙げられるが、本反応で使用できる反応剤はこれに限らない。反応剤の使用量は、式(1-1)で表される化合物に対して通常約1倍モル~3倍モルの範囲で適宜選択すればよく、また無水酢酸等の反応剤は過剰に加えることで無溶媒で反応させることができる。 Reactants that can be used in the present invention include, for example, acid chlorides such as acetyl chloride, trifluoroacetyl chloride, methyl chlorocarbonate, methanesulfonic acid chloride, trifluoromethanesulfonic acid chloride, acetic anhydride, trifluoroacetic anhydride, Acid anhydrides such as trifluorosulfonic anhydride; alkylating agents such as methyl iodide, ethyl iodide, 1,1,1-trifluoro-2-iodoethane, dimethyl sulfate, etc. can be used in this reaction. The reactant is not limited to this. The amount of the reactant to be used may be selected appropriately within the range of usually about 1 to 3 times the mole of the compound represented by formula (1-1), and reactants such as acetic anhydride may be added in excess. This allows the reaction to be carried out without a solvent.
本発明で使用できる塩基としては、例えば、トリエチルアミン、N,N-ジイソプロピルエチルアミン、ピリジン、水素化リチウム、水素化ナトリウム、水素化カリウム、水素化カルシウム等の水素化アルカリ金属、ノルマルブチルリチウム、ナトリウムビス(トリメチルシリル)アミド、リチウムビス(トリメチルシリル)アミド、カリウムビス(トリメチルシリル)アミド、リチウムジイソプロピルアミン等を挙げることができ、その使用量は、式(8)で表される化合物に対して通常約1倍モル~5倍モルの範囲で適宜選択すればよい。 Examples of the base that can be used in the present invention include triethylamine, N,N-diisopropylethylamine, pyridine, alkali metal hydrides such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride, n-butyllithium, and sodium bishydride. (trimethylsilyl)amide, lithium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, lithium diisopropylamine, etc., and the amount used is usually about 1 times that of the compound represented by formula (8). It may be appropriately selected within the range of mol to 5 times mol.
本反応で使用できる不活性溶媒としては、本反応を著しく阻害しないものであれば良く、例えば、ジエチルエーテル、テトラヒドロフラン、ジオキサン等の鎖状又は環状エーテル類;ベンゼン、トルエン、キシレン等の芳香族炭化水素類、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、ジメチルスルホキシド、1,3-ジメチル-2-イミダゾリノン等の極性溶媒を挙げることができ、これらの不活性溶媒は単独で又は2種以上混合して使用することができる。 Inert solvents that can be used in this reaction may be those that do not significantly inhibit this reaction, such as chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic carbonized solvents such as benzene, toluene, and xylene. Examples include polar solvents such as hydrogens, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone, and these inert solvents may be used alone or in combination with Can be used in combination of more than one species.
本反応における反応温度は通常約-78℃から使用する溶媒の沸点の範囲で行えばよく、反応時間は反応規模、反応温度等により一定しないが、数分~48時間の範囲で適宜選択すれば良い。また本反応は、例えば窒素ガスやアルゴンガスのような不活性ガスの雰囲気下で行うこともできる。反応終了後、目的物を含む反応系から常法により目的物を単離すれば良く、必要に応じて再結晶、カラムクロマトグラフィー等で精製することにより目的物を製造することができる。 The reaction temperature in this reaction is usually within the range of about -78°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but can be appropriately selected within the range of several minutes to 48 hours. good. Further, this reaction can also be carried out, for example, in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
工程c
Eが水素原子ではない場合、式(1-2)で表されるアミジン化合物を、塩基及び不活性溶媒の存在下、反応剤と反応させることにより式(1)で表されるアミジン化合物を製造することができる。
{式中、RA、RB、RD、A1、A2、G1、D及びEは前記と同じであることを示す。}Process c
When E is not a hydrogen atom, produce an amidine compound represented by formula (1) by reacting the amidine compound represented by formula (1-2) with a reactant in the presence of a base and an inert solvent. can do.
{In the formula, R A , R B , R D , A 1 , A 2 , G 1 , D and E are the same as above. }
本発明で使用できる反応剤としては、例えば、塩化アセチル、塩化トリフルオロアセチル、クロロ炭酸メチル、メタンスルホン酸塩化物、トリフルオロメタンスルホン酸塩化物等の酸塩化物;無水酢酸、無水トリフルオロ酢酸、無水トリフルオロスルホン酸等の酸無水物;ヨウ化メチル、ヨウ化エチル、1,1,1-トリフルオロ-2-ヨードエタン、硫酸ジメチル等のアルキル化剤が挙げられるが、本反応で使用できる反応剤はこれに限らない。反応剤の使用量は、式(1-2)で表される化合物に対して通常約1倍モル~3倍モルの範囲で適宜選択すればよい。 Examples of the reactant that can be used in the present invention include acid chlorides such as acetyl chloride, trifluoroacetyl chloride, methyl chlorocarbonate, methanesulfonic acid chloride, and trifluoromethanesulfonic acid chloride; acetic anhydride, trifluoroacetic anhydride, Acid anhydrides such as trifluorosulfonic anhydride; alkylating agents such as methyl iodide, ethyl iodide, 1,1,1-trifluoro-2-iodoethane, and dimethyl sulfate; however, reactions that can be used in this reaction include The agent is not limited to this. The amount of the reactant to be used may be appropriately selected in the range of usually about 1 to 3 times the mole of the compound represented by formula (1-2).
本発明で使用できる塩基としては、例えば、トリエチルアミン、N,N-ジイソプロピルエチルアミン、ピリジン、水素化リチウム、水素化ナトリウム、水素化カリウム、水素化カルシウム等の水素化アルカリ金属、ノルマルブチルリチウム、ナトリウムビス(トリメチルシリル)アミド、リチウムビス(トリメチルシリル)アミド、カリウムビス(トリメチルシリル)アミド、リチウムジイソプロピルアミン等を挙げることができ、その使用量は、式(1-2)で表される化合物に対して通常約1倍モル~5倍モルの範囲で適宜選択すればよい。 Examples of the base that can be used in the present invention include triethylamine, N,N-diisopropylethylamine, pyridine, alkali metal hydrides such as lithium hydride, sodium hydride, potassium hydride, and calcium hydride, n-butyllithium, and sodium bishydride. (trimethylsilyl)amide, lithium bis(trimethylsilyl)amide, potassium bis(trimethylsilyl)amide, lithium diisopropylamine, etc., and the amount used is usually about about The amount may be appropriately selected within the range of 1 to 5 times the mole.
本反応で使用できる不活性溶媒としては、本反応を著しく阻害しないものであれば良く、例えば、ジエチルエーテル、テトラヒドロフラン、ジオキサン等の鎖状又は環状エーテル類;ベンゼン、トルエン、キシレン等の芳香族炭化水素類、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、ジメチルスルホキシド、1,3-ジメチル-2-イミダゾリノン等の極性溶媒を挙げることができ、これらの不活性溶媒は単独で又は2種以上混合して使用することができる。 Inert solvents that can be used in this reaction may be those that do not significantly inhibit this reaction, such as chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic carbonized solvents such as benzene, toluene, and xylene. Examples include polar solvents such as hydrogens, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and 1,3-dimethyl-2-imidazolinone, and these inert solvents may be used alone or in combination with Can be used in combination of more than one species.
本反応における反応温度は通常約-78℃から使用する溶媒の沸点の範囲で行えばよく、反応時間は反応規模、反応温度等により一定しないが、数分~48時間の範囲で適宜選択すれば良い。また本反応は、例えば窒素ガスやアルゴンガスのような不活性ガスの雰囲気下で行うこともできる。反応終了後、目的物を含む反応系から常法により目的物を単離すれば良く、必要に応じて再結晶、カラムクロマトグラフィー等で精製することにより目的物を製造することができる。 The reaction temperature in this reaction is usually within the range of about -78°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but can be appropriately selected within the range of several minutes to 48 hours. good. Further, this reaction can also be carried out, for example, in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
<製造方法2>
工程d
式(1-1)で表されるアミジン化合物を、不活性溶媒の存在下、反応剤と反応させることにより式(2)で表されるアミジン化合物を製造することができる。本反応は文献記載の方法(Journal of Organic Chemistry, 2014, 79(10), p. 4687-4693)に準じて行うことができる。
{式中、RA、RB、RD、A1、A2、G1及びG2は前記と同じであることを示す。}<Manufacturing method 2>
Process d
An amidine compound represented by formula (2) can be produced by reacting an amidine compound represented by formula (1-1) with a reactant in the presence of an inert solvent. This reaction can be carried out according to the method described in the literature (Journal of Organic Chemistry, 2014, 79(10), p. 4687-4693).
{In the formula, R A , R B , R D , A 1 , A 2 , G 1 and G 2 are the same as above. }
本発明で使用できる反応剤としては、例えば、ヨードベンゼンジアセテート、(ビス(トリフルオロアセトキシ)ヨード)ベンゼン、ヨードシルベンゼン、(ヒドロキシ(トシルオキシ)ヨード)ベンゼン、2-ヨードキシ安息香酸、Dess-Martinペルヨージナン等の超原子化ヨウ素化合物等の酸化剤が挙げられるが、本反応で使用できる反応剤はこれに限らない。反応剤の使用量は、式(1-1)で表される化合物に対して通常約1倍モル~5倍モルの範囲で適宜選択すればよい。 Reactants that can be used in the present invention include, for example, iodobenzenediacetate, (bis(trifluoroacetoxy)iodo)benzene, iodosylbenzene, (hydroxy(tosyloxy)iodo)benzene, 2-iodooxybenzoic acid, Dess-Martin Examples include oxidizing agents such as hyperatomized iodine compounds such as periodinane, but the reactants that can be used in this reaction are not limited to these. The amount of the reactant to be used may be appropriately selected in the range of usually about 1 to 5 times the mole of the compound represented by formula (1-1).
本反応で使用できる不活性溶媒としては、本反応を著しく阻害しないものであれば良く、例えば、ジクロロメタン、1,2-ジクロロエタン等のハロゲン化溶剤、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、メタノール、エタノール、プロパノール、2,2,2、-トリフルオロエタノール、ヘキサフルオロ-2-プロパノール等のアルコール溶剤、酢酸エチル、アセトニトリル等を挙げることができ、これらの不活性溶媒は単独で又は2種以上混合して使用することができる。 Inert solvents that can be used in this reaction may be those that do not significantly inhibit this reaction, such as halogenated solvents such as dichloromethane and 1,2-dichloroethane, aromatic hydrocarbons such as benzene, toluene, and xylene. , methanol, ethanol, propanol, 2,2,2,-trifluoroethanol, hexafluoro-2-propanol and other alcohol solvents, ethyl acetate, acetonitrile, etc., and these inert solvents may be used alone or in combination with Can be used in combination of more than one species.
本反応における反応温度は通常約0℃から使用する溶媒の沸点の範囲で行えばよく、反応時間は反応規模、反応温度等により一定しないが、数分~48時間の範囲で適宜選択すれば良い。また本反応は、例えば窒素ガスやアルゴンガスのような不活性ガスの雰囲気下で行うこともできる。反応終了後、目的物を含む反応系から常法により目的物を単離すれば良く、必要に応じて再結晶、カラムクロマトグラフィー等で精製することにより目的物を製造することができる。 The reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be selected as appropriate within the range of several minutes to 48 hours. . Further, this reaction can also be carried out, for example, in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
<製造方法3>
工程e
式(1-1)で表されるアミジン化合物を、塩基及び不活性溶媒の存在下、反応剤と反応させることにより式(3)で表されるアミジン化合物を製造することができる。
{式中、RA、RB、RD、A1、A2、G1及びG2は前記と同じであることを示す。}<Manufacturing method 3>
Process e
An amidine compound represented by formula (3) can be produced by reacting an amidine compound represented by formula (1-1) with a reactant in the presence of a base and an inert solvent.
{In the formula, R A , R B , R D , A 1 , A 2 , G 1 and G 2 are the same as above. }
本発明で使用できる反応剤としては、例えば、クロロ炭酸メチル、クロロ炭酸エチル、クロロギ酸フェニル、クロロギ酸4-ニトロフェニル、クロロギ酸4-クロロフェニル、ホスゲン、トリホスゲン、カルボニルジイミダゾール等が挙げられるが、本反応で使用できる反応剤はこれに限らない。反応剤の使用量は、式(1-1)で表される化合物に対して通常約1倍モル~5倍モルの範囲で適宜選択すればよい。 Examples of the reactant that can be used in the present invention include methyl chlorocarbonate, ethyl chlorocarbonate, phenyl chloroformate, 4-nitrophenyl chloroformate, 4-chlorophenyl chloroformate, phosgene, triphosgene, carbonyldiimidazole, etc. The reactants that can be used in this reaction are not limited to these. The amount of the reactant to be used may be appropriately selected in the range of usually about 1 to 5 times the mole of the compound represented by formula (1-1).
本発明で使用できる塩基としては、例えば、トリエチルアミン、N,N-ジイソプロピルエチルアミン、ピリジン等を挙げることができ、その使用量は、式(1-1)で表される化合物に対して通常約1倍モル~5倍モルの範囲で適宜選択すればよい。 Examples of the base that can be used in the present invention include triethylamine, N,N-diisopropylethylamine, and pyridine, and the amount used is usually about 1 It may be appropriately selected within the range of twice the mole to five times the mole.
本反応で使用できる不活性溶媒としては、本反応を著しく阻害しないものであれば良く、例えば、ジクロロメタン、1,2-ジクロロエタン等のハロゲン化溶剤、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、ジエチルエーテル、テトラヒドロフラン、ジオキサン等の鎖状又は環状エーテル類;ベンゼン、トルエン、キシレン等の芳香族炭化水素類、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、ジメチルスルホキシド、1,3-ジメチル-2-イミダゾリノン等の極性溶媒、酢酸エチル、アセトニトリル等を挙げることができ、これらの不活性溶媒は単独で又は2種以上混合して使用することができる。 Inert solvents that can be used in this reaction may be those that do not significantly inhibit this reaction, such as halogenated solvents such as dichloromethane and 1,2-dichloroethane, aromatic hydrocarbons such as benzene, toluene, and xylene. , chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 1,3- Examples include polar solvents such as dimethyl-2-imidazolinone, ethyl acetate, acetonitrile, and the like, and these inert solvents can be used alone or in combination of two or more.
本反応における反応温度は通常約0℃から使用する溶媒の沸点の範囲で行えばよく、反応時間は反応規模、反応温度等により一定しないが、数分~48時間の範囲で適宜選択すれば良い。また本反応は、例えば窒素ガスやアルゴンガスのような不活性ガスの雰囲気下で行うこともできる。反応終了後、目的物を含む反応系から常法により目的物を単離すれば良く、必要に応じて再結晶、カラムクロマトグラフィー等で精製することにより目的物を製造することができる。 The reaction temperature in this reaction is usually within the range of about 0°C to the boiling point of the solvent used, and the reaction time varies depending on the reaction scale, reaction temperature, etc., but may be selected as appropriate within the range of several minutes to 48 hours. . Further, this reaction can also be carried out, for example, in an atmosphere of an inert gas such as nitrogen gas or argon gas. After completion of the reaction, the target product may be isolated from the reaction system containing the target product by a conventional method, and if necessary, the target product can be produced by purification by recrystallization, column chromatography, etc.
防除対象
本発明において防除の対象とする有害生物は特に限定されるものではなく、広範な農園芸における害虫、ダニ、線虫、土壌害虫の防除-殺虫を含む-に用いる事ができる。これらの有害生物を本発明中において、農園芸用害虫と定義する。好ましい防除対象虫種としては、例えば、以下のものが挙げられる。
鱗翅目害虫(Lepidoptera){例えば、ニカメイガ(Chilo suppressalis)、Darkheaded stem borer(Chilo polychrysus)、White stem borer(Scirpophaga innotata)、イッテンオオメイガ(Scirpophaga incertulas)、Rupela albina、コブノメイガ(Cnaphalocrocis medinalis)、Marasmia patnalis、イネハカジノメイガ(Marasmia exigua)、ワタノメイガ(Notarcha derogata)、アワノメイガ(Ostrinia furnacalis)、European corn borer(Ostrinia nubilalis)、ハイマダラノメイガ(Hellula undalis)、モンキクロノメイガ(Herpetogramma luctuosale)、シバツトガ(Pediasia teterrellus)、ライスケースワーム(Nymphula depunctalis)、Sugarcane borer(Diatraea saccharalis)等のツトガ科(Crambidae);モロコシマダラメイガ(Elasmopalpus lignosellus)、ノシメマダラメイガ(Plodia interpunctella)等のメイガ科(Pyralidae);ハスモンヨトウ(Spodoptera litura)、シロイチモジヨトウ(Spodoptera exigua)、アワヨトウ(Mythimna separata)、ヨトウガ(Mamestra brassicae)、イネヨトウ(Sesamia inferens)、シロナヨトウ(Spodoptera mauritia)、フタオビコヤガ(Naranga aenescens)、ツマジロクサヨトウ(Spodoptera frugiperda)、アフリカシロナヨトウ(Spodoptera exempta)、タマナヤガ(Agrotis ipsilon)、タマナギンウワバ(Autographa nigrisigna)、イネキンウワバ(Plusia festucae)、Soybean looper(Chrysodeixis includens)、トリコプルシア属(Trichoplusia spp.)、ニセアメリカタバコガ(Heliothis virescens)等のヘリオティス属(Heliothis spp.)、オオタバコガ(Helicoverpa armigera)、アメリカタバコガ(Helicoverpa zea)等のヘリコベルパ属(Helicoverpa spp.)、Velvetbean caterpillar(Anticarsia gemmatalis)、Cotton leafworm(Alabama argillacea)、Hop vine borer(Hydraecia immanis)等のヤガ科(Noctuidae);モンシロチョウ(Pieris rapae)等のシロチョウ科(Pieridae);ナシヒメシンクイ(Grapholita molesta)、スモモヒメシンクイ(Grapholita dimorpha)、マメシンクイガ(Leguminivora glycinivorella)、アズキサヤムシガ(Matsumuraeses azukivora)、リンゴコカクモンハマキ(Adoxophyes orana fasciata)、チャノコカクモンハマキ(Adoxophyes honmai)、チャハマキ(Homona magnanima)、ミダレカクモンハマキ(Archips fuscocupreanus)、コドリンガ(Cydia pomonella)、カンシャシンクイハマキ(Tetramoera schistaceana)、Bean Shoot Borer(Epinotia aporema)、Citrus fruit borer(Ecdytolopha aurantiana)等のハマキガ科(Tortricidae);チャノホソガ(Caloptilia theivora)、キンモンホソガ(Phyllonorycter ringoniella)のホソガ科(Gracillariidae);モモシンクイガ(Carposina sasakii)等のシンクイガ科(Carposinidae);Coffee Leaf miner(Leucoptera coffeella)、モモハモグリガ(Lyonetia clerkella)、ギンモンハモグリガ(Lyonetia prunifoliella)等のハモグリガ科(Lyonetiidae);マイマイガ(Lymantria dispar)等のリマントリア属(Lymantria spp.)、チャドクガ(Euproctis pseudoconspersa)等のユープロクティス属(Euproctis spp.)等のドクガ科(Lymantriidae);コナガ(Plutella xylostella)等のコナガ科(Pluteliidae);モモキバガ(Anarsia lineatella)、イモキバガ(Helcystogramma triannulella)、ワタアカミムシガ(Pectinophora gossypiella)、ジャガイモガ(Phthorimaea operculella)、Tuta absoluta等のキバガ科(Gelechiidae);アメリカシロヒトリ(Hyphantria cunea)等のヒトリガ科(Arctiidae);Giant Sugarcane borer(Telchin licus)等のカストニアガ科(Castniidae);ヒメボクトウ(Cossus insularis)等のボクトウガ科(Cossidae);ヨモギエダシャク(Ascotis selenaria)等のシャクガ科(Geometridae);ヒロヘリアオイラガ(Parasa lepida)等のイラガ科(Limacodidae);カキノヘタムシガ(Stathmopoda masinissa)等のニセマイコガ科(Stathmopodidae);クロメンガタスズメ(Acherontia lachesis)等のスズメガ科(Sphingidae);キクビスカシバ(Nokona feralis)等のスカシバガ科(Sesiidae);イネツトムシ(Parnara guttata)等のセセリチョウ科(Hesperiidae)}。
半翅目害虫(Hemiptera){例えば、ヒメトビウンカ(Laodelphax striatellus)、トビイロウンカ(Nilaparvata lugens)、セジロウンカ(Sogatella furcifera)、トウモロコシウンカ(Peregrinus maidis)、キタウンカ(Javesella pellucida)、クロフツノウンカ(Perkinsiella saccharicida)、Tagosodes orizicolus等のウンカ科(Delphacidae);ツマグロヨコバイ(Nephotettix cincticeps)、タイワンツマグロヨコバイ(Nephotettix virescens)、クロスジツマグロヨコバイ(Nephotettix nigropictus)、イナズマヨコバイ(Recilia dorsalis)、チャノミドリヒメヨコバイ(Empoasca onukii)、ジャガイモヒメヨコバイ(Empoasca fabae)、コーンリーフホッパー(Dalbulus maidis)、シロオオヨコバイ(Cofana spectra)等のヨコバイ科(Cicadellidae);Mahanarva posticata、Mahanarva fimbriolata等のコガシラアワフキムシ科(Cercopidae);マメクロアブラムシ(Aphis fabae)、ダイズアブラムシ(Aphis glycines)、ワタアブラムシ(Aphis gossypii)、ヨーロッパリンゴアブラムシ(Aphis pomi)、ユキヤナギアブラムシ(Aphis spiraecola)、モモアカアブラムシ(Myzus persicae)、ムギワラギクオマルアブラムシ(Brachycaudus helichrysi)、ダイコンアブラムシ(Brevicoryne brassicae)、Rosy apple aphid(Dysaphis plantaginea)、ニセダイコンアブラムシ(Lipaphis erysimi)、チューリップヒゲナガアブラムシ(Macrosiphum euphorbiae)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、レタスヒゲナガアブラムシ(Nasonovia ribisnigri)、ムギクビレアブラムシ(Rhopalosiphum padi)、トウモロコシアブラムシ(Rhopalosiphum maidis)、ミカンクロアブラムシ(Toxoptera citricida)、モモコフキアブラムシ(Hyalopterus pruni)、ヒエノアブラムシ(Melanaphis sacchari)、オカボノクロアブラムシ(Tetraneura nigriabdominalis)、カンシャワタアブラムシ(Ceratovacuna lanigera)、リンゴワタムシ(Eriosoma lanigerum)等のアブラムシ科(Aphididae);ブドウネアブラムシ(Daktulosphaira vitifoliae)、Pecan phylloxera(Phylloxera devastatrix)、Pecan leaf phylloxera(Phylloxera notabilis)、Southern pecan leaf phylloxera(Phylloxera russellae)等のネアブラムシ科(Phylloxeridae);ツガカサアブラムシ(Adelges tsugae)、Adelges piceae、ヒメカサアブラムシ(Aphrastasia pectinatae)等のカサアブラムシ科(Adelgidae);イネクロカメムシ(Scotinophara lurida)、Malayan rice black bug(Scotinophara coarctata)、アオクサカメムシ(Nezara antennata)、トゲシラホシカメムシ(Eysarcoris aeneus)、オオトゲシラホシカメムシ(Eysarcoris lewisi)、シラホシカメムシ(Eysarcoris ventralis)、ムラサキシラホシカメムシ(Eysarcoris annamita)、クサギカメムシ(Halyomorpha halys)、ミナミアオカメムシ(Nezara viridula)、Brown stink bug(Euschistus heros)、Red banded stink bug(Piezodorus guildinii)、Oebalus pugnax、Dichelops melacanthus等のカメムシ科(Pentatomidae);Burrower brown bug(Scaptocoris castanea)等のツチカメムシ科(Cydnidae);ホソヘリカメムシ(Riptortus pedestris)、クモヘリカメムシ(Leptocorisa chinensis)、ホソクモヘリカメムシ(Leptocorisa acuta)等のホソヘリカメムシ科(Alydidae);ホソハリカメムシ(Cletus punctiger)、アシビロヘリカメムシ(Leptoglossus australis)等のヘリカメムシ科(Coreidae);カンシャコバネナガカメムシ(Caverelius saccharivorus)、コバネヒョウタンナガカメムシ(Togo hemipterus)、アメリカコバネナガカメムシ(Blissus leucopterus)等のナガカメムシ科(Lygaeidae);アカヒゲホソミドリカスミカメ(Trigonotylus caelestialium)、アカスジカスミカメ(Stenotus rubrovittatus)、フタトゲムギカスミカメ(Stenodema calcarata)、サビイロカスミカメ(Lygus lineolaris)等のカスミカメムシ科(Miridae);オンシツコナジラミ(Trialeurodes vaporariorum)、タバココナジラミ(Bemisia tabaci)、ミカンコナジラミ(Dialeurodes citri)、ミカントゲコナジラミ(Aleurocanthus spiniferus)、チャトゲコナジラミ(Aleurocanthus camelliae)、ヒサカキワタフキコナジラミ(Pealius euryae)等のコナジラミ科(Aleyrodidae);シュロマルカイガラムシ(Abgrallaspis cyanophylli)、アカマルカイガラムシ(Aonidiella aurantii)、ナシマルカイガラムシ(Diaspidiotus perniciosus)、クワシロカイガラムシ(Pseudaulacaspis pentagona)、ヤノネカイガラムシ(Unaspis yanonensis)、ニセヤノネカイガラムシ(Unaspis citri)等のマルカイガラムシ科(Diaspididae);ルビーロウムシ(Ceroplastes rubens)等のカタカイガラムシ科(Coccidae);イセリアカイガラムシ(Icerya purchasi)、キイロワタフキカイガラムシ(Icerya seychellarum)等のワタフキカイガラムシ科(Margarodidae);ナスコナガイガラムシ(Phenacoccus solani)、クロテンコナカイガラムシ(Phenacoccus solenopsis)、フジコナカイガラムシ(Planococcus kraunhiae)、クワコナカイガラムシ(Pseudococcus comstocki)、ミカンコナカイガラムシ(Planococcus citri)、ガハニコナカイガラムシ(Pseudococcus calceolariae)、ナガオコナカイガラムシ(Pseudococcus longispinus)、タトルミーリーバグ(Brevennia rehi)等のコナカイガラムシ科(Pseudococcidae);ミカンキジラミ(Diaphorina citri)、ミカントガリキジラミ(Trioza erytreae)、ナシキジラミ(Cacopsylla pyrisuga)、チュウゴクナシキジラミ(Cacopsylla chinensis)、ジャガイモトガリキジラミ(Bactericera cockerelli)、Pear psylla(Cacopsylla pyricola)等のキジラミ科(Psyllidae);プラタナスグンバイ(Corythucha ciliata)、アワダチソウグンバイ(Corythucha marmorata)、ナシグンバイ(Stephanitis nashi)、ツツジグンバイ(Stephanitis pyrioides)等のグンバイムシ科;トコジラミ(Cimex lectularius)等のトコジラミ科(Cimicidae)及びGiant Cicada(Quesada gigas)等のセミ科(Cicadidae)}。
甲虫目害虫(Coleoptera){例えば、ウエスタンコーンルートワーム(Diabrotica virgifera virgifera)、サザンコーンルートワーム(Diabrotica undecimpunctata howardi)、ノザンコーンルートワーム(Diabrotica barberi)、メキシカンコーンルートワーム(Diabrotica virgifera zeae)、バンデッドキューカンバービートル(Diabrotica balteata)、Cucurbit Beetle(Diabrotica speciosa)、ビーンリーフビートル(Cerotoma trifurcata)、クビアカクビホソハムシ(Oulema melanopus)、ウリハムシ(Aulacophora femoralis)、キスジノミハムシ(Phyllotreta striolata)、Cabbage flea beetle(Phyllotreta cruciferae)、Western black flea beetle(Phyllotreta pusilla)、Cabbage stem flea beetle(Psylliodes chrysocephala)、コロラドハムシ(Leptinotarsa decemlineata)、イネドロオイムシ(Oulema oryzae)、グレープ・コラスピス(Colaspis brunnea)、コーン・フレアビートル(Chaetocnema pulicaria)、サツマイモヒサゴトビハムシ(Chaetocnema confinis)、ポテト・フレアビートル(Epitrix cucumeris)、イネトゲハムシ(Dicladispa armigera)、southern corn leaf beetle(Myochrous denticollis)、ヨツモンカメノコハムシ(Laccoptera quadrimaculata)、タバコノミハムシ(Epitrix hirtipennis)等のハムシ科(Chrysomelidae);Seedcorn beetle(Stenolophus lecontei)、Slender seedcorn beetle(Clivina impressifrons)等のオサムシ科(Carabidae);ドウガネブイブイ(Anomala cuprea)、ヒメコガネ(Anomala rufocuprea)、アオドウガネ(Anomala albopilosa)、マメコガネ(Popillia japonica)、ナガチャコガネ(Heptophylla picea)、European Chafer(Rhizotrogus majalis)、クロマルコガネ(Tomarus gibbosus)、Holotrichia属(Holotrichia spp.)、ジューン・ビートル(Phyllophaga crinita)等のPhyllophaga属(Phyllophaga spp.)、Diloboderus abderus等のDiloboderus属(Diloboderus spp.)等のコガネムシ科(Scarabaeidae);ワタミヒゲナガゾウムシ(Araecerus coffeae)、アリモドキゾウムシ(Cylas formicarius)、イモゾウムシ(Euscepes postfasciatus)、アルファルファタコゾウムシ(Hypera postica)、コクゾウムシ(Sitophilus zeamais)、イネゾウムシ(Echinocnemus squameus)、イネミズゾウムシ(Lissorhoptrus oryzophilus)、シロスジオサゾウムシ(Rhabdoscelus lineatocollis)、ワタミハナゾウムシ(Anthonomus grandis)、シバオサゾウムシ(Sphenophorus venatus)、Southern Corn Billbug(Sphenophorus callosus)、Soybean stalk weevil(Sternechus subsignatus)、Sugarcane weevil(Sphenophorus levis)、サビヒョウタンゾウムシ(Scepticus griseus)、トビイロヒョウタンゾウムシ(Scepticus uniformis)、ブラジルマメゾウムシ(Zabrotes subfasciatus)、マツノキクイムシ(Tomicus piniperda)、Coffee Berry Borer(Hypothenemus hampei)、Aracanthus mourei等のAracanthus属(Aracanthus spp.)、cotton root borer(Eutinobothrus brasiliensis)等のゾウムシ科(Curculionidae);コクヌストモドキ(Tribolium castaneum)、ヒラタコクヌストモドキ(Tribolium confusum)等のゴミムシダマシ科(Tenebrionidae);ニジュウヤホシテントウ(Epilachna vigintioctopunctata)等のテントウムシ科(Coccinellidae);ヒラタキクイムシ(Lyctus brunneus)等のナガシンクイムシ科(Bostrychidae);ヒョウホンムシ科(Ptinidae);ゴマダラカミキリ(Anoplophora malasiaca)、Migdolus fryanus等のカミキリムシ科(Cerambycidae);オキナワカンシャクシコメツキ(Melanotus okinawensis)、トビイロムナボソコメツキ(Agriotes fuscicollis)、クシコメツキ(Melanotus legatus)、アシブトコメツキ属(Anchastus spp.)、コノデルス属(Conoderus spp.)、クテニセラ属(Ctenicera spp.)、リモニウス属(Limonius spp.)、Aeolus属(Aeolus spp.)等のコメツキムシ科(Elateridae);アオバアリガタハネカクシ(Paederus fuscipes)等のハネカクシ科(Staphylinidae)}。
総翅目害虫(Thysanoptera){例えば、ミカンキイロアザミウマ(Frankliniella occidentalis)、ミナミキイロアザミウマ(Thrips palmi)、チャノキイロアザミウマ(Scirtothrips dorsalis)、ネギアザミウマ(Thrips tabaci)、ヒラズハナアザミウマ(Frankliniella intonsa)、イネアザミウマ(Stenchaetothrips biformis)、モトジロアザミウマ(Echinothrips americanus)等のアザミウマ科(Thripidae);イネクダアザミウマ(Haplothrips aculeatus)等のクダアザミウマ科(Phlaeothripidae)}。
双翅目害虫(Diptera){例えば、タネバエ(Delia platura)、タマネギバエ(Delia antiqua)等のハナバエ科(Anthomyiidae);シュガービートルートマゴット(Tetanops myopaeformis)等のハネフリバエ科(Ulidiidae);イネハモグリバエ(Agromyza oryzae)、トマトハモグリバエ(Liriomyza sativae)、マメハモグリバエ(Liriomyza trifolii)、ナモグリバエ(Chromatomyia horticola)等のハモグリバエ科(Agromyzidae);イネキモグリバエ(Chlorops oryzae)等のキモグリバエ科(Chloropidae);ウリミバエ(Bactrocera cucurbitae)、ミカンコミバエ(Bactrocera dorsalis)、ナスミバエ(Bactrocera latifrons)、オリーブミバエ(Bactrocera oleae)、クインスランドミバエ(Bactrocera tryoni)、チチュウカイミバエ(Ceratitis capitata)等のミバエ科(Tephritidae);イネヒメハモグリバエ(Hydrellia griseola)、トウヨウイネクキミギワバエ(Hydrellia philippina)、イネクキミギワバエ(Hydrellia sasakii)等のミギワバエ科(Ephydridae);オウトウショウジョウバエ(Drosophila suzukii)等のショウジョウバエ科;オオキモンノミバエ(Megaselia spiracularis)等のノミバエ科(Phoridae);オオチョウバエ(Clogmia albipunctata)等のチョウバエ科;チビクロバネキノコバエ(Bradysia difformis)等のクロバネキノコバエ科(Sciaridae);ヘシアンバエ(Mayetiola destructor)、イネノシントメタマバエ(Orseolia oryzae)等のタマバエ科(Cecidomyiidae);Diopsis macrophthalma等のシュモクバエ科(Diopsidae);キリウジガガンボ(Tipula aino)、Common cranefly(Tipula oleracea)、European cranefly(Tipula paludosa)等のガガンボ科(Tipulidae)}。
膜翅目害虫(Hymenoptera){例えば、カブラハバチ(Athalia rosae)、ニホンカブラバチ(Athalia japonica)等のハバチ科(Tenthredinidae);ファイヤーアント(Solenopsis spp.)科、Brown leaf-cutting ant(Atta capiguara)等のアリ科(Formicidae)等}。
直翅目害虫(Orthoptera){例えば、トノサマバッタ(Locusta migratoria)、モロッコトビバッタ(Dociostaurus maroccanus)、オーストラリアトビバッタ(Chortoicetes terminifera)、アカトビバッタ(Nomadacris septemfasciata)、Brown Locust(Locustana pardalina)、Tree Locust(Anacridium melanorhodon)、Italian Locust(Calliptamus italicus)、Differential grasshopper(Melanoplus differentialis)、Two striped grasshopper(Melanoplus bivittatus)、Migratory grasshopper(Melanoplus sanguinipes)、Red-Legged grasshopper(Melanoplus femurrubrum)、Clearwinged grasshopper(Camnula pellucida)、サバクワタリバッタ(Schistocerca gregaria)、Yellow-winged locust(Gastrimargus musicus)、Spur-throated locust(Austracris guttulosa)、コバネイナゴ(Oxya yezoensis)、ハネナガイナゴ(Oxya japonica)、タイワンツチイナゴ(Patanga succincta)等のバッタ科(Acrididae);ケラ(Gryllotalpa orientalis)等のケラ科(Gryllotalpidae);ヨーロッパイエコオロギ(Acheta domestica)、エンマコオロギ(Teleogryllus emma)等のコオロギ科(Gryllidae);Mormon cricket(Anabrus simplex)等のキリギリス科(Tettigoniidae)}。
ゴキブリ目害虫(Blattodea){例えば、チャバネゴキブリ(Blattella germanica)等のチャバネゴキブリ科(Blattellidae);クロゴキブリ(Periplaneta fuliginosa)、ワモンゴキブリ(Periplaneta americana)、トビイロゴキブリ(Periplaneta brunnea)、トウヨウゴキブリ(Blatta orientalis)、ヤマトゴキブリ(Periplaneta japonica)、コワモンゴキブリ(Periplaneta australasiae)等のゴキブリ科(Blattidae);ヤマトシロアリ(Reticulitermes speratus)、イエシロアリ(Coptotermes formosanus)、アメリカカンザイシロアリ(Incisitermes minor)、ダイコクシロアリ(Cryptotermes domesticus)、タイワンシロアリ(Odontotermes formosanus)、コウシュンシロアリ(Neotermes koshunensis)、サツマシロアリ(Glyptotermes satsumensis)、ナカジマシロアリ(Glyptotermes nakajimai)、カタンシロアリ(Glyptotermes fuscus)、オオシロアリ(Hodotermopsis sjostedti)、コウシュウイエシロアリ(Coptotermes guangzhouensis)、アマミシロアリ(Reticulitermes amamianus)、ミヤタケシロアリ(Reticulitermes miyatakei)、カンモンシロアリ(Reticulitermes kanmonensis)、タカサゴシロアリ(Nasutitermes takasagoensis)、ニトベシロアリ(Pericapritermes nitobei)、ムシャシロアリ(Sinocapritermes mushae)、Cornitermes cumulans等のシロアリ科(Termitidae)}。
ダニ目害虫(Acari){例えば、ナミハダニ(Tetranychus urticae)、カンザワハダニ(Tetranychus kanzawai)、ミツユビナミハダニ(Tetranychus evansi)、ミカンハダニ(Panonychus citri)、リンゴハダニ(Panonychus ulmi)、オリゴニカス属(Oligonychus spp.)等のハダニ科(Tetranychidae);ミカンサビダニ(Aculops pelekassi)、リュウキュウミカンサビダニ(Phyllocoptruta citri)、トマトサビダニ(Aculops lycopersici)、チャノサビダニ(Calacarus carinatus)、チャノナガサビダニ(Acaphylla theavagrans)、ニセナシサビダニ(Eriophyes chibaensis)、リンゴサビダニ(Aculus schlechtendali)、カキサビダニ(Aceria diospyri)、Aceria tosichella、シソサビダニ(Shevtchenkella sp.)等のフシダニ科(Eriophyidae);チャノホコリダニ(Polyphagotarsonemus latus)等のホコリダニ科(Tarsonemidae);ミナミヒメハダニ(Brevipalpus phoenicis)等のヒメハダニ科(Tenuipalpidae);ケナガハダニ科(Tuckerellidae);フタトゲチマダニ(Haemaphysalis longicornis)、キチマダニ(Haemaphysalis flava)、タイワンカクマダニ(Dermacentor taiwanensis)、アメリカイヌカクマダニ(Dermacentor variabilis)、ヤマトマダニ(Ixodes ovatus)、シュルツマダニ(Ixodes persulcatus)、ブラックレッグドチック(Ixodes scapularis)、アメリカキララマダニ(Amblyomma americanum)、オウシマダニ(Boophilus microplus)、クリイロコイタマダニ(Rhipicephalus sanguineus)等のマダニ科(Ixodidae);ケナガコナダニ(Tyrophagus putrescentiae)、ホウレンソウケナガコナダニ(Tyrophagus similis)等のコナダニ科(Acaridae);コナヒョウヒダニ(Dermatophagoides farinae)、ヤケヒョウヒダニ(Dermatophagoides pteronyssinus)等のチリダニ科(Pyroglyphidae);ホソツメダニ(Cheyletus eruditus)、クワガタツメダニ(Cheyletus malaccensis)、ミナミツメダニ(Cheyletus moorei)、イヌツメダニ(Cheyletiella yasguri)等のツメダニ科(Cheyletidae);ミミヒゼンダニ(Otodectes cynotis)、ヒゼンダニ(Sarcoptes scabiei)等のヒゼンダニ科(Sarcoptidae);イヌニキビダニ(Demodex canis)等のニキビダニ科(Demodicidae);ズツキダニ科(Listrophoridae);イエササラダニ科(Haplochthoniidae);イエダニ(Ornithonyssus bacoti)、トリサシダニ(Ornithonyssus sylviarum)等のオオサシダニ科(Macronyssidae);ワクモ(Dermanyssus gallinae)等のワクモ科(Dermanyssidae);アカツツガムシ(Leptotrombidium akamushi)等のツツガムシ科(Trombiculidae)等}。
植物寄生性線虫{例えば、イネシンガレセンチュウ(Aphelenchoides besseyi)、イチゴセンチュウ(Aphelenchoides fragariae)、ハガレセンチュウ(Aphelenchoides ritzemabosi)、マツノザイセンチュウ(Bursaphelenchus xylophilus)等の葉線虫目(Aphelenchida)線虫、ジャガイモシロシストセンチュウ(Globodera pallida)、ジャガイモシストセンチュウ(Globodera rostochiensis)、ムギシストセンチュウ(Heterodera avenae)、ダイズシストセンチュウ(Heterodera glycines)、テンサイシストセンチュウ(Heterodera schachtii)、クローバシストセンチュウ(Heterodera trifolii)、アレナリアネコブセンチュウ(Meloidogyne arenaria)、キタネコブセンチュウ(Meloidogyne hapla)、サツマイモネコブセンチュウ(Meloidogyne incognita)、ジャワネコブセンチュウ(Meloidogyne javanica)、リンゴネコブセンチュウ(Meloidogyne mali)、ミナミネグサレセンチュウ(Pratylenchus coffeae)、ノコギリネグサレセンチュウ(Pratylenchus drenatus)、チャネグサレセンチュウ(Pratylenchus loosi)、ムギネグサレセンチュウ(Pratylenchus neglectus)、キタネグサレセンチュウ(Pratylenchus penetrans)、クルミネグサレセンチュウ(Pratylenchus vulnus)、カンキツネモグリセンチュウ(Radopholus citrophilus)、バナナネモグリセンチュウ(Radopholus similis)等のハリセンチュウ目(Tylenchida)}。Target of Control The pests to be controlled in the present invention are not particularly limited, and can be used to control - including insecticide - pests, mites, nematodes, and soil pests in a wide range of agricultural and horticultural fields. These pests are defined as agricultural and horticultural pests in the present invention. Examples of preferable insect species to be controlled include the following:
Lepidoptera (e.g. Chilo suppressalis, Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Scirpophaga incertulas, Rupela albina, Cnaphalocrocis medinalis, Marasmia patnalis , Marasmia exigua, Notarcha derogata, Ostrinia furnacalis, European corn borer (Ostrinia nubilalis), Hellula undalis, Herpetogramma luctuosale, Pediasia teterrellus ), rice case worm (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc.; Crambidae; Pyralidae, such as Elasmopalpus lignosellus, Plodia interpunctella; Spodoptera litura), Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia, Naranga aenescens, Spodoptera frugiperda, African frugiperda Heliotis such as Spodoptera exempta, Agrotis ipsilon, Autographa nigrisigna, Plusia festucae, Soybean looper (Chrysodeixis includens), Trichoplusia spp., and Heliothis virescens. Genus Heliothis spp., Helicoverpa armigera, Helicoverpa zea, etc., Velvetbean caterpillar (Anticarsia gemmatalis), Cotton leafworm (Alabama argillacea), Hop vine borer (Hydraecia immanis) Noctuidae (Pieridae) such as Pieris rapae; Pieris rapae (Pieridae); Grapholita molesta, Grapholita dimorpha, Leguminivora glycinivorella, Matsumuraeses azukivora, apple coca Adoxophyes orana fasciata, Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, Cydia pomonella, Tetramoera schistaceana, Bean Shoot Borer Tortricidae (Epinotia aporema), Citrus fruit borer (Ecdytolopha aurantiana); Gracillariidae (Caloptilia theivora), Phyllonorycter ringoniella; Carposinidae (Carposinidae) such as Carposina sasakii Lyonetiidae, such as Coffee Leaf miner (Leucoptera coffeella), Lyonetia clerkella, and Lyonetia prunifoliella; Lymantria spp., such as Lymantria dispar, and Euproctis pseudoconspersa Lymantriidae, such as Euproctis spp.; Pluteliidae, such as Plutella xylostella; Anarsia lineatella, Helcystogramma triannulella, Pectinophora gossypiella, Gelechiidae, such as the potato moth (Phthorimaea operculella) and Tuta absoluta; Arctiidae, such as Hyphantria cunea; Castniidae, such as the Giant Sugarcane borer (Telchin licus); Cossus insularis ); Cossidae, such as Ascotis selenaria; Geometridae, such as Parasa lepida; Limacodidae, such as Parasa lepida; Stathmopodidae, such as Stathmopoda masinissa. Sphingidae, such as Acherontia lachesis; Sesiidae, such as Nokona feralis; Hesperiidae, such as Parnara guttata.
Hemiptera (e.g., Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, Peregrinus maidis, Javesella pellucida, Perkinsiella saccharicida, Tagosodes) orizicolus, etc.; Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Empoasca onukii, potato leafhopper Cicadellidae, such as Empoasca fabae, corn leaf hopper (Dalbulus maidis), and Cofana spectra; Cercopidae, such as Mahanarva posticata and Mahanarva fimbriolata; Aphis fabae, Aphis glycines, Aphis gossypii, Aphis pomi, Aphis spiraecola, Myzus persicae, Brachycaudus helichrysi, Brevicoryne brassicae ), Rosy apple aphid (Dysaphis plantaginea), Japanese radish aphid (Lipaphis erysimi), tulip aphid (Macrosiphum euphorbiae), potato aphid (Aulacorthum solani), lettuce aphid (Nasonovia ribisnigri), wheat aphid (Rhopalosiphum padi), Corn aphid (Rhopalosiphum maidis), orange black aphid (Toxoptera citricida), peach aphid (Hyalopterus pruni), hyaline aphid (Melanaphis sacchari), white black aphid (Tetraneura nigriabdominalis), Japanese black aphid (Ceratovacuna lanigera), apple boll beetle ( Aphididae (Eriosoma lanigerum); Phylloxeridae (Daktulosphaira vitifoliae), Pecan phylloxera (Phylloxera devastatrix), Pecan leaf phylloxera (Phylloxera notabilis), Southern pecan leaf phylloxera (Phylloxera russellae); Adelgidae, including Adelges tsugae, Adelges piceae, and Aphrastasia pectinatae; Scotinophara lurida, Malayan rice black bug, Scotinophara coarctata, Nezara antennata), Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Eysarcoris annamita, Halyomorpha halys, Nezara viridula, Pentatomidae, such as Brown stink bug (Euschistus heros), Red banded stink bug (Piezodorus guildinii), Oebalus pugnax, Dichelops melacanthus; Cydnidae, such as Burrower brown bug (Scaptocoris castanea); Riptortus Alydidae, including Cletus punctiger, Leptocorisa chinensis, and Leptocorisa acuta; Alydidae, including Cletus punctiger and Leptoglossus australis; (Coreidae); Lygaeidae, including Caverelius saccharivorus, Togo hemipterus, and Blissus leucopterus; Trigonotylus caelestialium, Togo hemipterus Miridae, including Stenotus rubrovittatus, Stenodema calcarata, and Lygus lineolaris; Trialeurodes vaporariorum, Bemisia tabaci, Dialeudes citri, and citrus AleeRodidae, such as tojecanthus spiniferus, Aleurocanthus Camelliae, Pealius Euryae, and other Konazi Ramin). (ABGRALLASPIS CYANOPHYLLI), Aonidiella Aurantii, Nashimaru Kai Garamushi ( Diaspidiotus perniciosus, Pseudaulacaspis pentagona, Unaspis yanonensis, Unaspis citri, and other members of Diaspididae; Coccidae, including Ceroplastes rubens. ; Margarodidae, such as Icerya purchasi and Icerya seychellarum; Phenacoccus solani, Phenacoccus solenopsis, and Planococcus kraunhiae Pseudococcidae, including Pseudococcus comstocki, Planococcus citri, Pseudococcus calceolariae, Pseudococcus longispinus, and Brevennia rehi; Psyllidae (Diaphorina citri), Trioza erytreae, Cacopsylla pyrisuga, Cacopsylla chinensis, Bactericera cockerelli, Pear psylla (Cacopsylla pyricola); Platanus Members of the family Chimicidae, such as Corythucha ciliata, Corythucha marmorata, Stephanitis nashi, and Stephanitis pyrioides; family Cimicidae, such as Cimex lectularius, and Giant Cicada (Quesada gigas), etc. Cicadidae}.
Coleoptera {e.g., Western corn rootworm (Diabrotica virgifera virgifera), Southern corn rootworm (Diabrotica undecimpunctata howardi), Northern corn rootworm (Diabrotica barberi), Mexican corn rootworm (Diabrotica virgifera zeae), banded cucumber Beetle (Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), Bean leaf beetle (Cerotoma trifurcata), Oulema melanopus, Aulacophora femoralis, Cabbage flea beetle (Phyllotreta striolata), Cabbage flea beetle (Phyllotreta cruciferae) , Western black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), Rice beetle (Oulema oryzae), Grape colapis (Colaspis brunnea), Corn flare beetle (Chaetocnema pulicaria), Sweet potato Potato beetles such as Chaetocnema confinis, potato flare beetle (Epitrix cucumeris), rice beetle (Dicladispa armigera), southern corn leaf beetle (Myochrous denticollis), Laccoptera quadrimaculata, and tobacco flea beetle (Epitrix hirtipennis) Family (Chrysomelidae); Carabidae (Carabidae), including Seedcorn beetle (Stenolophus lecontei), Slender seedcorn beetle (Clivina impressifrons); Anomala cuprea, Anomala rufocuprea, Anomala albopilosa, Popillia japonica , Heptophylla picea, European Chafer (Rhizotrogus majalis), Tomarus gibbosus, Holotrichia spp., June beetle (Phyllophaga crinita), Phyllophaga spp., Diloboderus abderus, etc. Scarabaeidae, including Diloboderus spp.; Araecerus coffeae, Cylas formicarius, Euscepes postfasciatus, Hypera postica, Sitophilus zeamais , Echinocnemus squameus, Lissorhoptrus oryzophilus, Rhabdoscelus lineatocollis, Anthonomus grandis, Sphenophorus venatus, Southern Corn Billbug (Sphenophorus callosus), Soybean stalk weevil (Sternechus) subsignatus), Sugarcane weevil (Sphenophorus levis), Sugarcane weevil (Scepticus griseus), Brown gourd weevil (Scepticus uniformis), Brazilian bean weevil (Zabrotes subfasciatus), Pine tree beetle (Tomicus piniperda), Coffee Berry Borer (Hypothenemus hampei), Aracanthus Curculionidae, such as Aracanthus spp., cotton root borer (Eutinobothrus brasiliensis); Tenebrionidae, such as Tribolium castaneum and Tribolium confusum; Tenda Escapes (Coccinellidae); );) Ebidacidae (Cerambycidae) such as Sesame Malasiaca (ANOPLOPLOPHORA MALASIACA) ); Melanotus okinawensis, Agriotes fuscicollis, Melanotus legatus, Anchastus spp., Conoderus spp., Ctenicera spp. ), Limonius spp., Aeolus spp., and other members of Elateridae; Staphylinidae, such as Paederus fuscipes.
Thysanoptera {e.g., Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, Frankliniella intonsa, Rice thrips Ma ( Thripidae, such as Stenchaetothrips biformis and Echinothrips americanus; Phlaeothripidae, such as Haplothrips aculeatus.
Diptera {for example, Anthomyiidae such as Delia platura and Delia antiqua; Ulidiidae such as sugar beetroot maggot (Tetanops myopaeformis); Agromyza oryzae ), Agromyzidae such as Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticola; Chloropidae such as Chlorops oryzae; Bactrocera cucurbitae, Citrus fruit fly ( Bactrocera dorsalis), Bactrocera latifrons, olive fruit fly (Bactrocera oleae), Quinceland fruit fly (Bactrocera tryoni), and Ceratitis capitata (Tephritidae); Ephydridae, such as Hydrellia philippina and Hydrellia sasakii; Drosophila, such as Drosophila suzukii; Phoridae, such as Megaselia spiracularis; Drosophila (Clogmia albipunctata); Sciaridae (Bradysia difformis); Cecidomyiidae (Mayetiola destructor), Orseolia oryzae (Cecidomyiidae); Diopsis macrophthalma Diopsidae, such as Tipula aino, Common cranefly (Tipula oleracea), European cranefly (Tipula paludosa).
Hymenoptera {e.g., Tenthredinidae, such as Athalia rosae and Athalia japonica; Solenopsis spp., Brown leaf-cutting ant (Atta capiguara), etc. Formicidae, etc.}.
Orthoptera (e.g. Locusta migratoria), Moroccan locust (Dociostaurus maroccanus), Australian locust (Chortoicetes terminifera), Red kite locust (Nomadacris septemfasciata), Brown Locust (Locustana pardalina), Tree Locust (Anacridium melanorhodon) ), Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus femurrubrum), Clearwinged grasshopper (Camnula pellucida), Desert locust Acrididae, such as (Schistocerca gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Oxya yezoensis, Oxya japonica, and Patanga succincta; (Gryllotalpidae) such as (Gryllotalpa orientalis); Gryllidae (Gryllidae) such as European house cricket (Acheta domestica) and Ema cricket (Teleogryllus emma); Katydidae (Tettigoniidae) such as Mormon cricket (Anabrus simplex)}.
Cockroach pests (Blattodea) {for example, Blattellidae, such as the German cockroach (Blattella germanica); black cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), brown cockroach (Periplaneta brunnea), European cockroach (Blatta orientalis), Cockroach family (Blattidae) such as Periplaneta japonica and Periplaneta australasiae; Reticulitermes speratus, Coptotermes formosanus, Incisitermes minor, Cryptotermes domesticus, Formosan Termites (Odontotermes formosanus), Neotermes koshunensis, Glyptotermes satsumensis, Glyptotermes nakajimai, Glyptotermes fuscus, Hodotermopsis sjostedti, Coptotermes guangzhouensis ), Amami Termitidae, such as Reticulitermes amamianus, Reticulitermes miyatakei, Reticulitermes kanmonensis, Nasutitermes takasagoensis, Pericapritermes nitobei, Sinocapritermes mushae, and Cornitermes cumulans. )}.
Acari (e.g., spider mites such as Tetranychus urticae, Tetranychus kanzawai, Tetranychus evansi, Panonychus citri, Panonychus ulmi, Oligonychus spp.) Family (Tetranychidae): Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, Eriophyidae, such as Aculus schlechtendali, Aceria diospyri, Aceria tosichella, and Shevtchenkella sp.; Tarsonemidae, such as Polyphagotarsonemus latus; Brevipalpus phoenicis Tenuipalpidae; Tuckerellidae; Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanensis, Dermacentor variabilis, Ixodes ovatus, Schulz. Ixodidae, including Ixodes persulcatus, Ixodes scapularis, Amblyomma americanum, Boophilus microplus, and Rhipicephalus sanguineus; Tyrophagus putrescentiae Acaridae, such as Tyrophagoides farinae and Dermatophagoides pteronyssinus; Pyroglyphidae, such as Dermatophagoides farinae and Dermatophagoides pteronyssinus; Cheyletus eruditus, Cheyletus malaccensis, Southern spotted mite ( Cheyletidae, such as Cheyletus moorei and Cheyletiella yasguri; Sarcoptidae, such as Otodectes cynotis and Sarcoptes scabiei; Demodicidae, such as Demodex canis ; Listrophoridae; Haplochthoniidae; Macronyssidae, including Ornithonyssus bacoti and Ornithonyssus sylviarum; Dermanyssidae, including Dermanyssus gallinae; Leptotrombidium Trombiculidae, such as akamushi).
Plant-parasitic nematodes {e.g., Aphelenchida nematodes such as Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi, and Bursaphelenchus xylophilus; Potato cyst nematode (Globodera pallida), potato cyst nematode (Globodera rostochiensis), wheat cyst nematode (Heterodera avenae), soybean cyst nematode (Heterodera glycines), sugar beet cyst nematode (Heterodera schachtii), clover cyst nematode (Heterodera trifolii), arena Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne mali, Pratylenchus coffeae, Pratyle nchus drenatus), Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus vulnus, Radopholus citrophilus, Banana nematode (Pratylenchus vulnus) Tylenchida, such as Radopholus similis).
本発明の化合物は、さらに、衛生害虫、貯殻害虫、衣類害虫、家屋害虫、寄生虫などの有害生物の防除にも使用できる。特に人獣に害をなす有害な無脊椎生物に対する防除効果にも優れ、これらの有害生物を本発明中において、動物寄生性害虫と定義する。防除の対象となる動物寄生性害虫としては、宿主動物の背、脇下、下腹部、内股部などに寄生して動物・鳥類から血液やフケなどの栄養源を得て生息するもの、および宿主動物の背、臀部などに飛来して動物・鳥類から血液やフケなどの栄養源を得て生息するものを包含する。動物寄生性害虫としては、ダニ類、シラミ類、ノミ類などが挙げられる。 The compounds of the present invention can also be used to control pests such as sanitary pests, shell pests, clothing pests, house pests, and parasites. It is particularly effective in controlling harmful invertebrates that harm humans and animals, and these harmful organisms are defined as animal parasitic pests in the present invention. Animal parasitic pests that can be controlled include those that live on the back, armpits, lower abdomen, inner thighs, etc. of host animals and obtain nutrients such as blood and dander from animals and birds; It includes those that fly to the backs and buttocks of animals and live there, obtaining nutrients such as blood and dander from animals and birds. Examples of animal parasitic pests include mites, lice, and fleas.
本発明の防除剤が有効な宿主動物としては、ヒト、イヌ、ネコ、マウス、ラット、ハムスター、モルモット、リス、ウサギ、フェレット;愛玩鳥(例えば、ハト、オウム、九官鳥、文鳥、インコ、ジュウシマツ、カナリア);ウシ、ウマ、ブタ、ヒツジ、ヤギ;家禽(例えば、アヒル、ニワトリ、ウズラ、ガチョウ);ミツバチ(例えば、セイヨウミツバチ、ニホンミツバチ);などが挙げられる。 Host animals for which the control agent of the present invention is effective include humans, dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets; pet birds (e.g., pigeons, parrots, mynahs, sparrows, parakeets, Japanese pine, canary); cow, horse, pig, sheep, goat; poultry (eg, duck, chicken, quail, goose); honey bee (eg, western honey bee, Japanese honey bee); and the like.
すなわち、本発明の有害生物防除剤は、前記の動物・鳥類を保護対象とした動物寄生性害虫防除剤として有効である。 That is, the pest control agent of the present invention is effective as a control agent for animal parasitic pests intended for protection of the above-mentioned animals and birds.
対象となるダニ類(Acari)としては以下の害虫が挙げられる。
中気門目(Mesostigmata)のダニ類(mite){例えば、ワクモ(Dermanyssus gallinae)等のワクモ科(Dermanyssidae);イエダニ属(Ornithonyssus spp.)のトリサシダニ(Ornithonyssus sylviarum)、ネッタイトリサシダニ(Ornithonyssus bursa)、イエダニ(Ornithonyssus bacoti)を含むオオサシダニ科(Macronyssidae)のダニ;トゲダニ属種(Laelaps spp.)のネズミトゲダニ(Laelaps echidninus)、ホクマントゲダニ(Laelaps jettmari)、ミツバチトゲダニ(Tropilaelaps clarae)を含むトゲダニ科(Laelapidae)のダニ;ヘギダニ属種(Varroa spp.)のミツバチヘギイタダニ(Varroa destructor)、バロアジャコブソニ(Varroa jacobsoni)、バロアアンデルウッディ(Varroa underwoodi)を含むヘギダニ科(Varroidae)のダニ}。
後気門目(Metastigmata)のマダニ類(tick){例えば、ナガヒメダニ属種(Argas spp.)のナガヒメダニ(Argas persicus)、アルガス・リフレクサス(Argas reflexus)、ヒメダニ属種(Ornithodoros spp.)のオルニトドラス・モウバータ(Ornithodoros moubata)を含むヒメダニ科(Argasidae)のマダニ;チマダニ属種(Haemaphysalis spp.)のヘマフィサリス・コンシナ(Haemaphysalis concinna)、ヘマフィサリス・パンクタータ(Haemaphysalis punctata)、ヘマフィサリス・シンアバリナ(Haemaphysalis cinnabarina)、ヘマフィサリス・オトフィラ(Haemaphysalis otophila)、ヘマフィサリス・レアチ(Haemaphysalis leachi)、フタトゲチマダニ(Haemaphysalis longicornis)、マゲシマチマダニ(Haemaphysalis mageshimaensis)、イエンチマダニ(Haemaphysalis yeni)、ツリガネチマダニ(Haemaphysalis campanulata)、クロウサギチマダニ(Haemaphysalis pentalagi)、キチマダニ(Haemaphysalis flava)、オオトゲチマダニ(Haemaphysalis megaspinosa)、ヤマトチマダニ(Haemaphysalis japonica)、ダグラスチマダニ(Haemaphysalis douglasi)、キララマダニ属種(Amblyomma spp.)のアンブリオマ・アメリカナム(Amblyomma americanum)、アンブリオマ・バリエガタム(Amblyomma variegatum)、アンブリオマ・マキュラタム(Amblyomma maculatum)、アンブリオマ・ヘブラエウム(Amblyomma hebraeum)、アンブリオマ・カジェネンス(Amblyomma cajennense)、タカサゴキララマダニ(Amblyomma testudinarium)、マダニ属種(Ixodes spp.)のマダニ(Ixodes ricinus)、イクソデス・ヘキサゴナス(Ixodes hexagonus)、イクソデス・キャニスガ(Ixodes canisuga)、イクソデス・ピロサス(Ixodes pilosus)、イクソデス・ルビキュンダス(Ixodes rubicundus)、イクソデス・スキャプラリス(Ixodes scapularis)、イクソデス・ホロシクラス(Ixodes holocyclus)、ヤマトマダニ(Ixodes ovatus)、シュルツェマダニ(Ixodes persulcatus)、タネガタマダニ(Ixodes nipponensis)、ウシマダニ亜属種(Boophilus spp.)のオウシマダニ(Rhipicephalus(Boophilus)microplus)、リピセファラス(ブーフィラス)・デコロラタス(Rhipicephalus(Boophilus)decoloratus)、リピセファラス(ブーフィラス)・アニュラタス(Rhipicephalus(Boophilus)annulatus)、リピセファラス(ブーフィラス)・カルセラタス(Rhipicephalus(Boophilus)calceratus)、コイタマダニ属種(Rhipicephalus spp.)のリピセファラス・エベルトシ(Rhipicephalus evertsi)、クリイロコイタマダニ(Rhipicephalus sanguineus)、リピセファラス・ブルサ(Rhipicephalus bursa)、リピセファラス・アッペンディキュラタス(Rhipicephalus appendiculatus)、リピセファラス・キャペンシス(Rhipicephalus capensis)、リピセファラス・ツラニカス(Rhipicephalus turanicus)、リピセファラス・ザンベジエンシス(Rhipicephalus zambeziensis)、カクマダニ属種(Dermacentor spp.)のデルマセントール・マルギナタス(Dermacentor marginatus)、デルマセントール・レティキュラタス(Dermacentor reticulatus)、デルマセントール・ピクタス(Dermacentor pictus)、デルマセントール・アルビピクタス(Dermacentor albipictus)、デルマセントール・アンデルソニ(Dermacentor andersoni)、デルマセントール・バリアビリス(Dermacentor variabilis)を含むマダニ科(Ixodidae)のダニ}。
無気門目(Astigmata)のコナダニ類(Acaridida){例えばキュウセンヒゼンダニ属種(Psoroptidae spp.)のヒツジキュウセンヒゼンダニ(Psoroptes ovis)、ウサギキュウセンヒゼンダニ(Psoroptes cuniculi)、ウマキュウセンヒヒゼンダニ(Psoroptes equi)、ショクヒヒゼンダニ属種(Chorioptes spp.)のショクヒヒゼンダニ(Chorioptes bovis)、オトデクテス属種(Otodectes spp.)のミミヒゼンダニ(Otodectes cynotis)を含むキュウセンヒゼンダニ科(Psoroptidae)のダニ;ヒゼンダニ属種(Sarcoptes spp.)のセンコウヒゼンダニ(Sarcoptes scabiei)、イヌセンコウヒゼンダニ(Sarcoptes canis)、ウシセンコウヒゼンダニ(Sarcoptes bovis)、ヒツジセンコウヒゼンダニ(Sarcoptes ovis)、サルコプテス・ルピカプラエ(Sarcoptes rupicaprae)、ウマセンコウヒゼンダニ(Sarcoptes equi)、ブタセンコウヒゼンダニ(Sarcoptes suis)、ノトエドス属種(Notoedres spp.)のネコショウセンコウヒゼンダニ(Notoedres cati)を含むヒゼンダニ科(Sarcoptidae)のダニ;トリアシヒゼンダニ属種(Knemidokoptes spp.)のトリアシヒゼンダニ(Knemidokoptes mutans)を含むトリヒゼンダニ科(Knemidokoptidae)のダニ}。
前気門目(Prostigmata)のケダニ類(Actinedida){例えばニキビダニ属種(Demodex spp.)のイヌニキビダニ(Demodex canis)、ウシニキビダニ(Demodex bovis)、ヒツジニキビダニ(Demodex ovis)、ヤギニキビダニ(Demodex caprae)、ウマニキビダニ(Demodex equi)、デモデックス・カバリ(Demodex caballi)、ブタニキビダニ(Demodex suis)、ネコニキビダニ(Demodex cati)を含むニキビダニ科(Demodixidae)のダニ;ツツガムシ属種(Trombicula spp.)のトロンビキュラ・アルフレズゲシ(Trombicula alfreddugesi)、トロンビキュラ・アカムシ(Trombicula akamushi)を含むツツガムシ科(Trombiculidae)}。
シラミ類(Phthiraptera)としては以下の害虫が挙げられる。
シラミ亜目(Anoplura)のシラミ類(louse){例えばブタジラミ属種(Haematopinus spp.)のウマジラミ(Haematopinus asini)、ウシジラミ(Haematopinus eurysternus)、ブタジラミ(Haematopinus suis)を含むケモノジラミ科(Haematopinidae)のシラミ;リノグナツス属種(Linognathus spp.)のイヌジラミ(Linognathus setosus)、ウシホソジラミ(Linognathus vituli)、リノグナサス・オビラス(Linognathus ovillus)、リノグナサス・オビフォルミス(Linognathus oviformis)、リノグナサス・ペダリス(Linognathus pedalis)、ヤギホソジラミ(Linognathus stenopsis)、ソレノポテス属種(Solenopotes spp.)のケブカウシジラミ(Solenopotes capillatus)を含むケモノホソジラミ科(Linognathidae)のシラミ}。
タンカクハジラミ亜目 (Amblycera)のハジラミ類(biting louse){例えばメナカンツス属種(Menacanthus spp.)のニワトリオオハジラミ(Menacanthus stramineus)、ニワトリツノハジラミ(Menacanthus cornutus)、ウスイロニワトリハジラミ(Menacanthus pallidulus)、例えばメノポン属種(Menopon spp.)のニワトリハジラミ(Menopon gallinae)を含むタンカクハジラミ科(Menoponidae)のハジラミ}。
チョウカクハジラミ亜目(Ischnocera)のハジラミ類(biting louse){例えばコランビコーラ属種(Columbicola spp.)のハトナガハジラミ(Columbicola columbae)、クルクロトガステル属種(Cuclotogaster spp.)のハバビロナガハジラミ(Cuclotogaster heterographus)、ゴニオデス属種(Goniodes spp.)のカクアゴハジラミ(Goniodes dissimilis)、マルハジラミ(Goniodes gigas)、ヒメニワトリハジラミ(Goniodes gallinae)、リペウルス属種(Lipeurus spp.)のニワトリナガハジラミ(Lipeurus caponis)を含むチョウカクハジラミ科(Philopteridae)のハジラミ;ボビコーラ属種(Bovicola spp.)のウシハジラミ(Bovicola bovis)、ヒツジハジラミ(Bovicola ovis)、ボビコラ・リンバータ(Bovicola limbata)、ヤギハジラミ(Bovicola caprae)、ウマハジラミ(Bovicola equi)、ケモノハジラミ属種(Trichodectes spp.)のイヌハジラミ(Trichodectes canis)、フェリコラ属種(Felicola spp.)のネコハジラミ(Felicola subrostrata)を含むケモノハジラミ科(Trichodectidae)のハジラミ}。
ノミ類(Siphonaptera)としては以下の害虫が挙げられる。
例えばスナノミ属種(Tunga spp.)のスナノミ(Tunga penetrans)を含むスナノミ科(Tungidae)のノミ;イヌノミ属種(Ctenocephalides spp.)のイヌノミ(Ctenocephalides canis)、ネコノミ(Ctenocephalides felis)、アルカエオプシラ属種(Archaeopsylla spp.)のハリネズミノミ(Archaeopsylla erinacei)、ネズミノミ属種(Xenopsylla spp.)の東洋ネズミノミ(Xenopsylla cheopis)、ヒトノミ属種(Pulex spp.)のヒトノミ(Pulex irritans)、エチドノファガ属種(Echidnophaga spp.)のニワトリフトノミ(Echidnophaga gallinacea)を含むヒトノミ科(Pulicidae)のノミ;ナガノミ属種(Ceratophyllus spp.)のトリノミ(Ceratophyllus gallinae)、ヤマトネズミノミ(Ceratophyllus anisus)、ノソプスルラス属種(Nosopsyllus spp.)のヨーロッパネズミノミ(Nosopsyllus fasciatus)を含むナガノミ科(Ceratophyllidae)のノミ;ホソノミ属種(Leptopsylla spp.)のメクラネズミノミ(Leptopsylla segnis)を含むホソノミ科(Leptopsyllidae)のノミ。
その他にも、対象となる動物寄生性害虫としては、半翅目(Hemiptera)の害虫が挙げられる。半翅目(Hemiptera)の害虫としては以下の害虫が挙げられる。例えば、シメックス属種(Cimex spp.)のトコジラミ(Cimex lectularius)を含むトコジラミ科(Cimicidae)の昆虫;パンストロンギラス属種(Panstrongylus spp.)、ロドニウス属種(Rhodnius spp.)のベネズエラサシガメ(Rhodnius prolixus)、サシガメ属種(Triatoma spp.)のサシガメ(Triatoma infestans)を含むサシガメ科(Reduviidae)の昆虫。
その他にも、刺咬性昆虫(咀嚼性ハエ、吸血成虫ハエ、移動性双翅類の幼虫、寄生バエのウジ)である双翅目(Diptera)害虫にも有効である。ハエ類(Diptera)の害虫としては以下の害虫が挙げられる。長角亜目(Nematocera){例えば (a)イエカ属種(Culex spp.)のネッタイイエカ(Culex quinquefasciatus)、アカイエカ(Culex pipiens pallens)、キュレックス・タルサリス(Culex tarsalis)、チカイエカ(Culex pipiens molestus)、ネッタイイエカ(Culex pipiens fatigans)、コガタアカイエカ(Culex tritaeniorhynchus summorosus)、アルミゲレス属種(Armigeres spp.)のオオクロヤブカ(Armigeres subalbatus)、ハマダラカ属種(Anopheles spp.)のガンビアハマダラカ(Anopheles gambiae)、アノフェレス・マキュリペニス(Anopheles maculipennis)、シナハマダラカ(Anopheles sinensis)、オオツルハマダラカ(Anopheles lesteri)、ヤブカ属種(Aedes spp.)のネッタイシマカ(Aedes aegypti)、ヒトスジシマカ(Aedes albopictus)、イーデス・タエニオリンクス(Aedes taeniorhynchus)、トウゴウヤブカ(Aedes togoi)、キンイロヤブカ(Aedes vexans nipponii)を含むカ科(Culicidae)のカ; (b)ブユ属種(Simulium spp.)のシムリウム・レプタンス(Simulium reptans)、ツメトゲブユ(Simulium ornatum)、ヒメアシマダラブユ(Simulium venustum)、ウマブユ(Simulium salopiense)、プロシムリウム属種(Prosimulium spp)のキアシオオブユ(Prosimulium yezoense)を含むブユ科(Simuliidae)のブユ;クリコイデス属種(Culiodes spp.)のニワトリヌカカ(Culicoides arakawae)、ウスシロフヌカカ(Culicoides pictimargo)、キブネヌカカ(Culicoides kibunensis)、セマダラヌカカ(Culicoides homotomus)、ウシヌカカ(Culicoides oxystoma)、ニッポンヌカカ(Culicoides nipponensis)、ホシヌカカ(Culicoides punctatus)、ミヤマヌカカ(Culicoides maculatus)、マツザワヌカカ(Culicoides matsuzawai)を含むヌカカ科(Ceratopogonidae)のヌカカ。}。短角亜目{例えば、 (a)例えばアブ属種(Tabanus spp.)のタバヌス・ブロミウス(Tabanus bromius)、タバヌス・スポドプテルス(Tabanus spodopterus)、タバヌス・アトラタス(Tabanus atratus)、タバヌス・スデチカス(Tabanus sudeticus)、ウシアブ(Tabanus trigonus)、アカウシアブ(Tabanus chrysurus)、シロフアブ(Tabanus trigeminus)、キスジアブ(Tabanus fulvimedioides)、イヨシロオビアブ(Tabanus iyoensis)、メクラアブ属種(Chrysops spp.)のクリソプス・カエキュチエンス(Chrysops caecutiens)、クリソプス・レリクタス(Chrysops relictus)、キンメアブ(Chrysops suavis)、クロキンメアブ(Chrysops japonicus)を含むアブ科(Tabanidae)のアブ;イエバエ属種(Muscina spp.)のイエバエ(Musca domestica)、クロイエバエ(Musca bezzii)、ノイエバエ(Musca hervei)、ウスイロイエバエ(Musca conducens)、オオイエバエ(Musca stabulans)、サシバエ属種(Stomoxys spp.)のサシバエ(Stomoxys calcitrans)、ノサシバエ属種(Haematobia spp.)のノサシバエ(Haematobia irritans)、ヘマトビア・イリタンス・エクシグア(Haematobia irritans exigua)、ヘマトビア・スティミュランス(Haematobia stimulans)、ヒメイエバエ属種(Fannia spp.)のヒメイエバエ(Fannia canisularis)を含むイエバエ科(Muscidae)のハエ;シェシェバエ属種(Glossina spp.)を含むツエツエバエ科(Glossinidae)のハエ;メロファガス属種(Melophagus spp.)のシラミバエ(Melophagus ovinus)を含むシラミバエ科(Hippoboscidae)のハエ;クロバエ属種(Calliphora)の、オオクロバエ(Calliphora lata);、キンバエ属種(Lucilia spp.)のヒツジキンバエ(Lucilia (Phaenicia) cuprina)ヒロズキンバエ(Lucilia (Phaenicia) sericata)、ミドリキンバエ(Lucilia illustris)、オビキンバエ属(Chrysomyia. spp.)のラセンウジバエ(Chrysomya hominivorax)、クリソミア・クロロピガ(Chrysomya chloropyga)、クリソミア・ベジアナ(Chrysomya bezziana)を含むクロバエ科(Calliphoridae)のハエ;カワモグリバエ亜科(Cuterebrinae)のウサギヒフバエ属種(Cuterebra spp.)、ウシバエ亜科(Hypodermatinae)のさらにはウシバエ属種(Hypoderma spp.)のウシバエ(Hypoderma bovis)、キスジウシバエ(Hypoderma lineatum)、ウマバエ亜科(Gasterophilinae)のさらにはウマバエ属種(Gasterophilus spp.)のウマバエ(Gasterophilus intestinalis)、アトアカウマバエ(Gasterophilus haemorroidalis)、ガステロフィラス・イネルミス(Gasterophilus inermis)、ムネアカウマバエ(Gasterophilus nasalis)、ガステロフィラス・ニグリコルニス(Gasterophilus nigricornis)、アカウマバエ(Gasterophilus pecorum)、ヒツジバエ亜科(Oestrinae)のさらにはヒツジバエ属種(Oestrus spp.)のヒツジバエ(Oestrus ovis)を含むヒツジバエ科(Oestridae)のハエ)。The following pests are listed as target mites (Acari).
mites of the order Mesostigmata (e.g., Dermanyssidae, such as Dermanyssus gallinae; Ornithonyssus sylviarum and Ornithonyssus bursa of the genus Ornithonyssus spp.) Mites of the Macronyssidae family, including the house dust mite (Ornithonyssus bacoti); the Laelapidae family, including the Laelaps spp. ) mites; mites of the family Varroidae, including the Varroa destructor, Varroa jacobsoni, and Varroa underwoodi of the Varroa spp.
Ticks of the order Metastigmata {e.g. Argas spp. Argas persicus, Argas reflexus, Ornithodoros spp. Ornithodorus - Ticks of the Argasidae family, including Ornithodoros moubata; Haemaphysalis spp. Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis・Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis longicornis, Haemaphysalis mageshimaensis, Haemaphysalis yeni, Haemaphysalis campanulata, Haemaphysalis pentalagi ), wood tick (Haemaphysalis flava), Haemaphysalis megaspinosa, Haemaphysalis japonica, Haemaphysalis douglasi, Amblyomma spp. Amblyomma americanum, Amblyomma variegatum , Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Amblyomma testudinarium, Ixodes ricinus, Ixodes ricinus Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes ovatus ), Ixodes persulcatus, Ixodes nipponensis, Rhipicephalus (Boophilus microplus) of the subgenus Boophilus spp., Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) calceratus, Rhipicephalus spp. ) Rhipicephalus evertsi, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus (Rhipicephalus turanicus), Rhipicephalus zambeziensis, Dermacentor spp. Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus ), Dermacentor albipictus, Dermacentor andersoni, and Dermacentor variabilis.
Acaridida of the order Astigmata (e.g. Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi) of the Psoroptidae spp. Mites of the family Psoroptidae, including Chorioptes bovis of the genus Chorioptes spp. and Otodectes cynotis of the genus Otodectes spp.; Sarcoptes spp. spp.) Sarcoptes scabiei, Sarcoptes canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae, Sarcoptes equi Mites of the family Sarcoptidae, including Sarcoptes suis, Notoedres cati of the genus Notoedres spp.; Sarcoptidae of the genus Sarcoptes spp. Mites of the family Knemidokoptidae, including (Knemidokoptes mutans).
Actinedida of the order Prostigmata {e.g. Demodex spp. Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae ), Demodex equi, Demodex caballi, Demodex suis, and Demodex cati; Demodixidae mites; Trombicula spp. Trombiculidae, which includes Trombicula alfreddugesi and Trombicula akamushi.
Lice (Phthiraptera) include the following pests:
louse of the suborder Anoplura {e.g. lice of the family Haematopinidae, including the horse lice (Haematopinus asini), cow lice (Haematopinus eurysternus), and pig lice (Haematopinus suis) of the genus Haematopinus spp.; Linognathus spp. dog lice (Linognathus setosus), cow lice (Linognathus vituli), Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, goat lice (Linognathus spp.) gnathus stenopsis) lice of the Linognathidae family, including the Solenopotes capillatus of the Solenopotes spp.
Biting louse of the suborder Amblycera {e.g. Menacanthus stramineus, Menacanthus cornutus, Menacanthus pallidulus of the Menacanthus spp. , for example, lice of the Menoponidae family, including the Menopon gallinae of the Menopon spp.
Biting louse of the suborder Ischnocera (e.g. Columbicola columbae of the genus Columbicola spp., biting louse of the genus Cuclotogaster spp. Goniodes dissimilis, Goniodes gigas, Goniodes gallinae, Lipeurus caponis, Lipeurus spp. Bovicola bovis, Bovicola ovis, Bovicola limbata, Bovicola caprae, Bovicola equi of the family Philopteridae; Bovicola spp. ), dog lice (Trichodectes canis) of the genus Trichodectes spp., and cat lice (Felicola subrostrata) of the genus Felicola spp.
Fleas (Siphonaptera) include the following pests:
For example, fleas of the family Tungidae, including sand fleas (Tunga penetrans) of the genus Tunga spp.; fleas of the genus Ctenocephalides canis, Ctenocephalides felis, cat fleas (Ctenocephalides felis) of the genus Ctenocephalides spp., spp. Archaeopsylla erinacei (Archaeopsylla erinacei), Oriental mouse flea (Xenopsylla cheopis) (Xenopsylla spp.), Pulex irritans (Pulex spp.), Echidnophaga spp. fleas of the Pulicidae family, including the chicken flea (Echidnophaga gallinacea); Ceratophyllus spp., the avian flea (Ceratophyllus gallinae), the mountain rat flea (Ceratophyllus anisus), and the Nosopsyllus spp. fleas of the family Ceratophyllidae, including the European mouse flea (Nosopsyllus fasciatus); fleas of the family Ceratophyllidae, including the European rat flea (Leptopsylla segnis) of the genus Leptopsylla spp.;
Other target animal parasitic pests include pests of the order Hemiptera. Pests of the order Hemiptera include the following: For example, insects of the Cimicidae family, including Cimex spp. bed bugs (Cimex lectularius); Panstrongylus spp., Rhodnius spp. Venezuelan assassin bugs (Rhodnius spp.); Insects of the family Reduviidae, including the assassin bugs (Triatoma infestans) of the genus Triatoma spp.
It is also effective against Diptera pests, which are biting insects (chewing flies, blood-sucking adult flies, migratory dipteran larvae, and parasitic fly maggots). Pests of flies (Diptera) include the following: Suborder Nematocera {e.g. (a) Culex spp. Culex quinquefasciatus, Culex pipiens pallens, Culex tarsalis, Culex pipiens molestus, Culex pipiens fatigans, Culex tritaeniorhynchus summorosus, Armigeres subalbatus of Armigeres spp., Anopheles gambiae of Anopheles spp., Anopheles maculipenis maculipennis), Anopheles sinensis, Anopheles lesteri, Aedes spp. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Aedes spp. (b) Mosquitoes of the family Culicidae, including Simulium spp. Blackflies of the family Simuliidae, including Simulium venustum, Simulium salopiense, Prosimulium yezoense of Prosimulium spp.; Culicoides arakawae of Culiodes spp.; Culicoides pictimargo, Culicoides kibunensis, Culicoides homotomus, Culicoides oxystoma, Culicoides nipponensis, Culicoides punctatus, Culicoides maculatus, Matsuzawanu Contains Kaka (Culicoides matsuzawai) Nukaka of the Ceratopogonidae family. }. Brachyceran {e.g. (a) Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, e.g. Tabanus spp. ), Tabanus trigonus, Tabanus chrysurus, Tabanus trigeminus, Tabanus fulvimedioides, Tabanus iyoensis, Chrysops caecutiens, Chrysops spp.・Flies of the family Tabanidae, including Chrysops relictus, Chrysops suavis, and Chrysops japonicus; Muscina spp., including Musca domestica, Musca bezzii, and black flies (Musca hervei), Musca conducens, Musca stabulans, Stomoxys calcitrans of Stomoxys spp., Haematobia irritans of Haematobia spp., Haematobia irritans - Flies of the family Muscidae, including Haematobia irritans exigua, Haematobia stimulans, Fannia canisularis of Fannia spp.; Glossina spp. flies of the family Glossinidae, including Melophagus spp. flies; flies of the Hipboboscidae family, including Melophagus ovinus; , Lucilia (Phaenicia) cuprina of Lucilia spp., Lucilia (Phaenicia) sericata, Lucilia illustris, Chrysomya hominivorax of Chrysomyia. spp. Flies of the family Calliphoridae, including Chrysomya chloropyga and Chrysomya bezziana; Cuterebra spp. of the subfamily Cuterebrinae; ), Hypoderma bovis of Hypodermatinae and Hypoderma spp., Hypoderma lineatum, Gasterophilinae and Gasterophilus spp. Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Oestrinae ) as well as flies of the Oestridae family, including Oestrus ovis of the Oestrus spp.
本発明の化合物を農園芸用害虫防除剤として用いる場合、本発明の化合物をそのまま用いても良いが、適当な固体担体、液体担体、ガス状担体等、界面活性剤、分散剤、その他の製剤用補助剤、等とともに混合して農薬製剤を調製して用いても良い。前記農薬製剤として、好ましくは、乳剤、EW剤、液剤、懸濁剤、水和剤、顆粒水和剤、粉剤、DL粉剤、粉粒剤、粒剤、錠剤、油剤、エアゾル、フロアブル剤、ドライフロアブル剤、マイクロカプセル剤、等を挙げる事ができる。これら農薬製剤として任意に選択される剤型として用いることができる。本発明での担体とは固体担体、液体担体、ガス状担体等を指す。 When using the compound of the present invention as an agricultural and horticultural pest control agent, the compound of the present invention may be used as it is, but it may also be used in combination with a suitable solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant, or other preparation. It may also be used by mixing it with agricultural auxiliaries, etc. to prepare an agrochemical formulation. The agrochemical formulation is preferably an emulsion, an EW agent, a liquid, a suspension, a wettable powder, a wettable powder, a powder, a DL powder, a powder, a granule, a tablet, an oil, an aerosol, a flowable agent, or a dry powder. Examples include flowable agents, microcapsules, and the like. These agricultural chemical formulations can be used in arbitrarily selected dosage forms. The carrier in the present invention refers to solid carriers, liquid carriers, gaseous carriers, and the like.
前記固体担体としては、例えばタルク、ベントナイト、クレー、カオリン、ケイソウ土、バーミキュライト、ホワイトカーボン、炭酸カルシウム、酸性白土、珪砂、珪石、ゼオライト、パーライト、アタパルジャイト、軽石、硫酸アンモニウム、硫酸ナトリウム、尿素等が挙げられる。
前記液体担体としては、例えば、メタノール、エタノール、n-ヘキサノール、エチレングリコール、プロピレングリコール等のアルコール類、アセトン、メチルエチルケトン、シクロヘキサノン等のケトン類、n-ヘキサン、ケロシン、灯油等の脂肪族炭化水素類、トルエン、キシレン、メチルナフタレン等の芳香族炭化水素類、ジエチルエーテル、ジオキサン、テトラヒドロフラン等のエーテル類、酢酸エチル等のエステル類、アセトニトリル、イソブチロニトリル等のニトリル類、ジメチルホルムアミド、ジメチルアセトアミド等の酸アミド類、ダイズ油、綿実油等の植物油類、ジメチルスルホキシド、水等が挙げられる。
また、前記ガス状担体としてはLPG、空気、窒素、炭酸ガス、ジメチルエーテル等があげられる。
前記界面活性剤および前記分散剤としては、例えば、アルキル硫酸エステル類、アルキル(アリール)スルホン酸塩類、ポリオキシアルキレンアルキル(アリール)エーテル類、多価アルコールエステル類、リグニンスルホン酸塩、アルキルスルホコハク酸塩、アルキルナフタレンスルホン酸塩のホルマリン縮合物、ポリカルボン酸塩、POEポリスチリルフェニルエーテル硫酸塩およびリン酸塩、POE・POPブロックポリマー等が挙げられる。
さらに、前記製剤用補助剤としては、例えば、カルボキシメチルセルロース、ヒドロキシプロピルセルロース、ポリビニルアルコール、キサンタンガム、α化デンプン、アラビアガム、ポリビニルピロリドン、エチレン-アクリル酸共重合体、エチレン-酢酸ビニル共重合体、ポリエチレングリコール、流動パラフィン、ステアリン酸カルシウム、及び消泡剤、防腐剤等が挙げられる。
前記の各種担体、界面活性剤、分散剤、および製剤用補助剤は、必要に応じて各々単独で、あるいは組み合わせて用いることができる。 Examples of the solid carrier include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate, acid clay, silica sand, silica stone, zeolite, pearlite, attapulgite, pumice, ammonium sulfate, sodium sulfate, urea, and the like. It will be done.
Examples of the liquid carrier include alcohols such as methanol, ethanol, n-hexanol, ethylene glycol, and propylene glycol, ketones such as acetone, methyl ethyl ketone, and cyclohexanone, and aliphatic hydrocarbons such as n-hexane, kerosene, and kerosene. , aromatic hydrocarbons such as toluene, xylene, and methylnaphthalene, ethers such as diethyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, dimethylformamide, dimethylacetamide, etc. acid amides, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, water, and the like.
Further, examples of the gaseous carrier include LPG, air, nitrogen, carbon dioxide, dimethyl ether, and the like.
Examples of the surfactant and the dispersant include alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, lignin sulfonates, and alkyl sulfosuccinic acids. Examples include salts, formalin condensates of alkylnaphthalene sulfonates, polycarboxylate salts, POE polystyrylphenyl ether sulfates and phosphates, POE/POP block polymers, and the like.
Furthermore, the formulation adjuvants include, for example, carboxymethyl cellulose, hydroxypropyl cellulose, polyvinyl alcohol, xanthan gum, pregelatinized starch, gum arabic, polyvinylpyrrolidone, ethylene-acrylic acid copolymer, ethylene-vinyl acetate copolymer, Examples include polyethylene glycol, liquid paraffin, calcium stearate, antifoaming agents, preservatives, and the like.
The various carriers, surfactants, dispersants, and formulation auxiliaries described above can be used alone or in combination, if necessary.
当該農薬製剤中における有効成分である本発明の化合物の含有量は、特に限定されないが、好ましくは、乳剤で1~75重量%、粉剤では0.3~25重量%、水和剤では1~90重量%、粒剤では0.1~10重量%である。 The content of the compound of the present invention as an active ingredient in the agricultural chemical formulation is not particularly limited, but is preferably 1 to 75% by weight for emulsions, 0.3 to 25% by weight for powders, and 1 to 1% for wettable powders. 90% by weight, and 0.1 to 10% by weight for granules.
本発明の化合物をウシ、ブタなどの家畜類、イヌ、ネコなどのペット類の動物に寄生するダニ類の防除剤とする場合には、使用量は特に限定されないが、例えば、宿主動物1kgに対して、有効成分が、0.01~1000mgの割合となる量で使用することができる。
本発明の化合物は、公知の獣医学的な手法で宿主動物へ施用することができる。その方法として、例えば、全身的抑制を目的とする場合には、錠剤、カプセル、浸漬液、飼料混入、坐薬、注射(筋肉内、皮下、静脈内、腹腔内など)などにより動物に投与する方法などが挙げられ、非全身的抑制を目的とする場合は、油性または水性液剤を噴霧、注ぎかけ(pour-on)、滴下(spot-on)などにより投与する方法、樹脂に本化合物を練り込み、該混練物を首輪、耳札などの適当な形状に成形し、それを動物に装着する方法などが挙げられる。When using the compound of the present invention as a control agent for mites parasitic on domestic animals such as cows and pigs, and pets such as dogs and cats, the amount used is not particularly limited, but for example, 1 kg of the host animal may be used. On the other hand, the active ingredient can be used in an amount of 0.01 to 1000 mg.
The compounds of the present invention can be applied to host animals using known veterinary techniques. For example, when the purpose is systemic suppression, methods include administering to animals via tablets, capsules, immersion liquid, feed mixture, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), etc. If the purpose is non-systemic suppression, methods include administering oil-based or aqueous solutions by spraying, pour-on, spot-on, etc., or by kneading the compound into resin. Examples include a method of forming the kneaded material into a suitable shape such as a collar or ear tag, and attaching it to an animal.
本発明による有害生物防除剤は、そのままで、または希釈して用いることができる。また、本発明による有害生物防除剤は他の殺虫剤、殺線虫剤、殺菌剤、殺ダニ剤、除草剤、植物成長調節剤、肥料等と混合または併用することができる。混合または併用することができる薬剤としては、例えば、ペスティサイドマニュアル(第17版、The British Crop Protection Council発行)およびシブヤインデックス(SHIBUYA INDEX 第17版、2014年、SHIBUYA INDEX RESEARCH GROUP発行)およびアイラックモードオブアクションクラスィフィケィションスキーム(Mode of Action Classification Scheme Version8.2版、IRAC発行)、エフラックコードリスト(FRAC Code List (c)*2017: Fungicides sorted by mode of action、2017年度版、FRAC発行)に記載のものやインターネットで構造が特定できるもの(https://www.alanwood.net/pesticides/sitemap.html)が挙げられる。 The pest control agent according to the present invention can be used as is or diluted. Furthermore, the pest control agent according to the present invention can be mixed with or used in combination with other insecticides, nematicides, fungicides, acaricides, herbicides, plant growth regulators, fertilizers, and the like. Examples of drugs that can be mixed or used in combination include Pesticide Manual (17th edition, published by The British Crop Protection Council), Shibuya Index (SHIBUYA INDEX 17th edition, 2014, published by SHIBUYA INDEX RESEARCH GROUP), and I. FRAC Code List (c)*2017: Fungicides sorted by mode of action, 2017 edition, Examples include those described in FRAC (published by FRAC) and those whose structures can be identified on the Internet (https://www.alanwood.net/pesticides/sitemap.html).
より具体的には、殺虫剤は、例えば、アラニカルブ(alanycarb)、アルジカルブ(aldicarb)、ベンダイオカルブ(bendiocarb)、ベンフラカルブ(benfuracarb)、ブトカルボキシム(butocarboxim)、ブトキシカルボキシム(butoxycarboxim)、カルバリル(carbaryl)、カルボフラン(carbofuran)、カルボスルファン(carbosulfan)、エチオフェンカルブ(ethiofencarb)、フェノブカルブ(fenobucarb)、ホルメタネート(formetanate)、フラチオカルブ(furathiocarb)、イソプロカルブ(isoprocarb)、メチオカルブ(methiocarb)、メソミル(methomyl)、オキサミル(oxamyl)、ピリミカルブ(pirimicarb)、プロポキスル(propoxur)、チオジカルブ(thiodicarb)、チオファノックス(thiofanox)、トリアザメート(triazamate)、トリメタカルブ(trimethacarb)、XMC、キシリルカルブ(xylylcarb)、メトルカルブ(metolcarb)、フェノチオカルブ(fenothiocarb)、フェノキシカルブ(fenoxycarb)のようなカーバメート系化合物、
アセフェート(acephate)、アザメチホス(azamethiphos)、アジンホス-エチル(azinphos-ethyl)、アジンホス-メチル(azinphos-methyl)、エチルチオメトン(ethylthiometon)、クロルエトキシホス(chlorethoxyfos)、カズサホス(cadusafos)、クロレトキシホス(chlorethoxyfos)、クロルフェンビンホス(chlorfenvinphos)、クロルメホス(chlormephos)、クロルピリホス(chlorpyrifos)、クロルピリホスメチル(chlorpyrifos-methyl)、クマホス(coumaphos)、シアノホス(cyanophos)、デメトン-S-メチル(demeton-S-methyl)、ダイアジノン(diazinon)、ジクロルボス(dichlorvos)、ジクロトホス(dicrotophos)、ジメトエート(dimethoate)、ジメチルビンホス(dimethylvinphos)、EPN、エチオン(ethion)、エトプロホス(etoprophos)、ファムフール(famphur)、フェナミホス(fenamifos)、フェニトロチオン(fenitrothion)、フェンチオン(fenthion)、ホスチアゼート(fosthiazate)、ヘプテノホス(heptenophos)、イミシアホス(imicyafos) 、イソフェンホス(isofenphos)、イソプロピル=O-(メトキシアミノチオホスホリル)サリチレート[isopropyl O-(methoxyaminothiophosphoryl)salicylate]、イソキサチオン(isoxathion)、マラチオン(malathion)、メカルバム(mecarbam)、メタミドホス(methamidophos)、メチダチオン(methidathion)、メビンホス(mevinphos)、モノクロトホス(monocrotophos)、ナレド(naled)、オメトエート(omethoate)、オキシジメトンエチル(dioxydemeton ethyl)、パラチオン(parathion)、パラチオン-メチル(parathion-methyl) 、PAP、ホレート(phorate)、ホサロン(phosalone)、ホスメット(phosmet)、ホスファミドン(phosphamidon)、ホキシム(phoxim)、ピリミホス-メチル(pirimiphos-methyl)、プロフェノホス(profenofos) 、プロペタンホス(propetamphos)、プロチオホス(prothiofos)、ピラクロホス(pyraclofos)、ピリダフェンチオン(pyridaphenthion)、キナルホス(quinalphos)、スルホテップ(sulfotep)、テブピリミホス(tebupirimfos)、テメホス(temephos)、テルブホス(terbufos)、テトラクロルビンホス(tetrachlorvinphos)、チオメトン(thiometon)、トリアゾホス(triazophos)、トリクロルホン(trichlorfon)、バミドチオン(vamidothion)、クロルピリホス-エチル(chlorpyrifos-ethyl)、ジスルフォトン(disulfoton)、スルプロホス(sulprofos)、フルピラゾホス(flupyrazophos)、フェントエート(phenthoate)、ホノホス(fonofos)、トリブホス(tribufos)のような有機リン酸エステル系化合物、
エンドスルファン(endosulfan) 、アルファ-エンドスルファン(alpha-endosulfan)、ガンマ-HCH(gamma-HCH) 、ジコホル(dicofol) 、クロルデン(chlordane)、ディルドリン(dieldrin)、メトキシクロル(methoxyclor)のような有機塩素系化合物、
アセトプロール(acetoprole)、フィプロニル(fipronil)、エチプロール(ethiprole)、ピラフルプロール(pyrafluprole)、ピリプロール(pyriprole)、フルフィプロール(flufiprole)のようなフェニルピラゾール系化合物、
ブロフラニリド(broflanilide)のようなメタジアミド系化合物、
アフォキソラネル(afoxolaner)、フルララネル(fluralaner)、サロラネル(sarolaner)、フルキサメタミド(fluxametamide)、ロティラネル(lotilaner)、イソシクロシラム(isocycloseram)のようなイソキサゾリン系化合物、
アクリナトリン(acrinathrin)、アレスリン(allethrin)、d-cis-transアレスリン、d-transアレスリン(d-cis-trans allethrin)、ビフェントリン(bifenthrin)、カッパ-ビフェントリン(kappa-bifenthrin)、ビオアレスリンS-シクロペンテニル(bioallethrin S-cyclopentenyl)、ビオレスメトリン(bioresmethrin)、シクロプロトリン(cycloprothrin)、シフルトリン(cyfluthrin)、ベータ-シフルトリン(beta-cyfluthrin)、シハロトリン(cyhalothrin)、ラムダ-シハロトリン(ramda-cyhalothrin)、ガンマ-シハロトリン(gamma-cyhalothrin)、シペルメトリン(cypermethrin)、アルファ-シペルメトリン(alpha-cypermethrin)、ベータ-シペルメトリン(beta-cypermethrin)、シータ-シペルメトリン(theta-cypermethrin)、ゼータ-シペルメトリン(zeta-cypermethrin)、シフェノトリン(cyphenothrin)、デルタメトリン(deltamethrin)、エンペントリン(empenthrin)、エスフェンバレレート(esfenvalerate)、エトフェンプロックス(ethofenprox)、フェンプロパトリン(fenpropathrin)、フェンバレレート(fenvalerate)、フルシトリネート(flucythrinate)、フルメトリン(flumethrin)、タウ-フルバリネート(tau-fluvalinate)、ハルフェンプロックス(halfenprox)、イミプロトリン(imiprothrin)、カデスリン(kadethrin)、ペルメトリン(permethrin)、フェノトリン(phenothrin)、プラレトリン(prallethrin)、ピレトリン(pyrethrin)、レスメトリン(resmethrin)、シラフルオフェン(silafluofen)、テフルトリン(tefluthrin)、カッパ-テフルトリン(kappa-tefluthrin)、フタルスリン(phthalthrin)、テトラメトリン(tetramethrin)、トラロメトリン(tralomethrin)、トランスフルトリン(transfluthrin)、メトキサジアゾン(metoxadiazone)、メトフルトリン(metofluthrin)、プロフルトリン(profluthrin)、ピレトラム(pyrethrum)、テラレトリン(terallethrin)、モンフルオロスリン(momfluorothrin)、ヘプタフルトリン(heptafluthrin)、メペルフルスリン(meperfluthrin)、テトラメチルフルスリン(tetramethylfluthrin)、ジメフルトリン(dimefluthrin)、クロロパラレスリン(chloroprallethrin)、イプシロン-メトフルスリン(ipsilon-metofluthrin)、イプシロン-モンフルオスリン(ipsilon-momfluorothrin)、プロトリフェンブト(protrifenbut)のようなピレスロイド系化合物、
アセタミプリド(acetamiprid)、クロチアニジン(chlothianidin)、ジノテフラン(dinotefuran)、イミダクロプリド(imidacloprid)、ニテンピラム(nitenpyram)、チアクロプリド(thiacloprid)、チアメトキサム(thiamethoxam)のようなネオニコチノイド化合物、
スルホキサフロル(sulfoxaflor)のようなスルホキサミン系化合物、
フルピラジフロン(flupyradifurone)のようなブテノライド系化合物、
トリフルメゾピリム(triflumezopyrim)、ジクロロメゾチアズ(dicloromezotiaz)のようなメソイオン系化合物、
フルピリミン(flupyrimin)のような2-アミノピリジン系化合物
スピノサド(spinosad)、スピネトラム(spinetoram)のようなスピノシン系化合物、
アバメクチン(abamectin)、イベルメクチン(ivermectin)、エマメクチン安息香酸塩(emamectin benzoate)、ミルベメクチン(milbemectin)、レピメクチン(lepimectin)のようなマクロライド系化合物、
ヒドロプレン(hydroprene)、キノプレン(quinoprene)、ジオフェノラン(Diofenolan)、メトプレン(methoprene)のような幼若ホルモン様化合物、
ピリプロキシフェン(pyriproxyfene)のような4-フェノキシフェノキシ系化合物、
ピメトロジン(pymetrozine)のようなピリジンアゾメチン系化合物、
フロニカミド(flonicamid)のようなピリジンカルボキサミド系化合物、
エトキサゾール(ethoxazole)のようなオキサゾール系化合物、
B.t. subsp. israelensis、B.t. subsp.aizawai、B.t. subsp. kurstaki、B.t. subsp. tenebrionisのようなBacillus thuringiensisおよびBacillus sphaericus剤及びそれらが産生する殺虫性タンパク、
前記に該当するBt作物(Bacillus thuringiensisの毒素を産生する遺伝子を組み込み害虫抵抗性を持たせた遺伝子組み換え作物)が産生する殺虫性タンパク、
ジアフェンチウロン(diafenthiuron)のようなチオウレア系化合物、
アゾシクロチン(azocyclotin)、シヘキサチン(cyhexatin)、酸化フェンブタスズ(fenbutatin oxide)のような有機金属系化合物、
プロパルギット(propargite)のような亜硫酸エステル系・ジフェニルエーテル系化合物、
テトラジホン(tetradifon)のようなジフェニルスルホン系化合物、
クロルフェナピル(chlorfenapyr) 、トラロピリル(tralopyril)のようなピロール系化合物、
DNOCのようなジニトロ系化合物、
ベンスルタップ(bensultap)、カルタップ(cartap)、チオシクラム(thiocyclam)、チオスルタップ(thiosultap)、チオスルタップ-ナトリウム(thiosultap sodium)のようなネライストキシン類縁体、
ビストリフルロン(bistrifluron)、クロルフルアズロン(chlorfluazuron) 、ジフルベンズロン(diflubenzuron)、フルシクロクスロン(flucycloxuron)、フルフェノクスロン(flufenoxuron)、ヘキサフルムロン(hexaflumuron)、ルフェヌロン(lufenuron)、ノバルロン(novaluron)、ノビフルムロン(noviflumuron)、テフルベンズロン(teflubenzuron)、トリフルムロン(triflumuron)、ビストリフルロン(bistrifluron)のようなベンゾイルウレア系化合物、
ブプロフェジン(buprofezin)のようなチアジアジン系化合物、
シロマジン(cyromazine)のようなトリアゾール系化合物、
クロマフェノジド(chromafenozide)、ハロフェノジド(halofenozide)、メトキシフェノジド(methoxyfenozide)、テブフェノジド(tebufenozide)のようなジアシルヒドラジン系化合物、
アミトラズ(amitraz)のようなアミジン系化合物、
ヒドラメチルノン(hydramethylnon)のようなアミジノヒドラゾン系化合物、
アセキノシル(acequinocyl)のようなナフトキノン系化合物、
フルアクリピリム(fluacrypyrim)、ピリミノストロビン(pyriminostrobin)、フルフェノキシストロビン(Flufenoxystrobin)のようなストロビルリン系化合物、
フェナザキン(fenazaquin)のようなキナゾリン系化合物、
フェンピロキシメート(fenpyroxymate)のようなフェノキシピラゾール系化合物、
ピリミジフェン(pyrimidifen)のようなフェノキシエチルアミン系化合物、
ピリダベン(pyridaben)のようなピリダジノン系化合物、
テブフェンピラド(tebufenpyrad)、トルフェンピラド(tolfenpyrad)、ピフルブミド(pyflubumide)のようなピラゾールカルボキサミド系化合物、
メタフルミゾン(metaflumizone)のようなヒドラジンカルボキサミド系化合物、
スピロジクロフェン(spirodiclofen)、スピロテトラマト(spirotetaramat)、スピロメシフェン(spiromesifen)、スピロピディオン(spiropidion)のようなテトロン酸およびテトラミン酸系化合物、
シフルメトフェン(cyflumetofen)、シエノピラフェン(cyenopyrafen)のようなベータ-ケトニトリル系化合物、
フルベンジアミド(flubendiamide)のようなフタル酸アミド系化合物、
クロラントラニリプロール(chlorantraniliprole)、シアントラニリプロール(cyantraniliprole)、シクラニリプロール(cyclaniliprole)、テトラニリプロール(tetraniliprole)、シハロジアミド(cyhalodiamide)、テトラクロラントラニリプロール(tetrachlorantraniliprole)のようなアントラニル酸アミド系化合物、
キノメチオネート(quinomethionate)のようなキノキサリン系化合物、
ヘキシチアゾクス(hexythiazox)のようなチアゾリジノン系化合物、
ビフェナゼート(bifenazate)のようなヒドラジン系化合物、
フルフェネリム(flufenerim)のようなピリジナミン系化合物、
ピリフルキナゾン(pyrifluquinazon)のようなアミノキナゾリン系化合物、
フロメトキン(flometoquin)のような6-フェノキシキノリン系化合物、
フルオピラム(fluopyram)のようなピリジニルエチルベンズアミド系化合物、
フルアザインドリジン(fluazaindolizine)、アミドフルメト(amidoflumet)のようなスルホンアミド系化合物
チクロピラゾフロル(tyclopyrazoflor)のようなピリジルピラゾール系化合物
チオキサザフェン(tioxazafen)のようなオキサジアゾール系化合物、
オキサゾスルフィル(oxazosulfyl)のようなベンゾオキサゾール系化合物
であり得る。
また、その他の殺虫剤として、ニコチン(nicotine)、クロロピクリン(chloropicrin)、フッ化スルフリル(sulfuryl fluoride)、クリロチエ(crylotie)、クロフェンテジン(clofentezine)、ジフロビダジン(diflovidazin)、ロテノン(rotenone)、インドキサカルブ(indoxacarb)、ピペロニルブトキシド(piperonyl butoxide)、クロルジメホルム(chlordimeform)、ピリダリル(pyridalyl)、アザジラクチン(azadirachtin)、ベンゾキシメート(benzoxymate)、アフィドピロペン(afidopyropen)、フルヘキサホン(fluhexafon)、フルエンスルホン(fluensulfone)、ベンクロチアズ(benclothiaz)、カルゾール(carzole)、殺虫性石鹸、ジメヒポ(dimehypo)、ニチアジン(nithiazine)、ホウ酸塩(borate salt)、メタアルデヒド(metaaldehyde)、リアノジン(ryanodine)、スルフルラミド(sulfluramid)、アシノナピル(acynonapyr)、ベンズピリモキサン(benzpyrimoxan)、3-ブロモ-N-(2,4-ジクロロ-6-(メチルカルバモイル)フェニルイル)-1-(3,5-ジクロロピリジン-2-イル)-1H-ピラゾール-5-カルボキサミドのような化合物が挙げられる。更に、本発明による有害生物防除剤は、昆虫病原性バクテリア、昆虫病原性ウイルスおよび昆虫病原性菌類などのような微生物農薬とも、混用または併用することもできる。More specifically, the insecticides include, for example, alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl ( carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, Oxamyl, pirimicarb, propoxur, thiodicarb, thiophanox, triazamate, trimethacarb, XMC, xylylcarb, metolcarb, phenothiocarb (fenothiocarb), carbamate compounds such as fenoxycarb,
acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, ethylthiometon, chlorethoxyfos, cadusafos, chlorethoxyfos, Chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon (diazinon), dichlorvos, dicrotophos, dimethoate, dimethylvinphos, EPN, ethion, etoprophos, famphur, fenamifos, fenitrothion ( fenitrothion), fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl)salicylate, isoxathion (isoxathion), malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, dioxydemeton ethyl, parathion, parathion-methyl, PAP, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos- methyl), profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos ( terbufos), tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion, chlorpyrifos-ethyl, disulfoton, sulprofos, Organophosphate compounds such as flupyrazophos, phenthoate, fonofos, tribufos,
Organochlorine compounds such as endosulfan, alpha-endosulfan, gamma-HCH, dicofol, chlordane, dieldrin, methoxychlor;
phenylpyrazole compounds such as acetoprole, fipronil, ethiprole, pyrafluprole, pyriprole, flufiprole;
Metadiamide compounds such as broflanilide,
isoxazoline compounds such as afoxolaner, fluralaner, sarolaner, fluxametamide, lotilaner, isocycloseram;
Acrinathrin, allethrin, d-cis-trans allethrin, d-cis-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin S-cyclopentenyl (bioallethrin S-cyclopentenyl), bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin (gamma-cyhalothrin), cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin ), cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate ), flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin, prallethrin, pyrethrin (pyrethrin), resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, phthalthrin, tetramethrin, tralomethrin, transfluthrin, metoxadiazone, metofluthrin, profluthrin, pyrethrum, terallethrin, momfluorothrin, heptafluthrin, meperfluthrin, tetramethylfluthrin ), pyrethroid compounds such as dimefluthrin, chloroprallethrin, ipsilon-metofluthrin, ipsilon-momfluorothrin, protrifenbut;
neonicotinoid compounds such as acetamiprid, chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam;
sulfoxamine compounds, such as sulfoxaflor;
butenolide compounds such as flupyradifurone,
mesoionic compounds such as triflumezopyrim, dicloromezotiaz,
2-aminopyridine compounds such as flupyrimin; spinosyn compounds such as spinosad and spinetoram;
macrolides such as abamectin, ivermectin, emamectin benzoate, milbemectin, lepimectin;
Juvenile hormone-like compounds such as hydroprene, quinoprene, Diofenolan, methoprene;
4-phenoxyphenoxy compounds such as pyriproxyfene,
Pyridine azomethine compounds such as pymetrozine,
Pyridine carboxamides such as flonicamid,
Oxazole compounds such as ethoxazole,
Bacillus thuringiensis and Bacillus sphaericus agents and the insecticidal proteins they produce, such as Bt subsp. israelensis, Bt subsp. aizawai, Bt subsp. kurstaki, Bt subsp. tenebrionis;
Insecticidal proteins produced by Bt crops that fall under the above (genetically modified crops that incorporate the toxin-producing gene of Bacillus thuringiensis and have insect resistance);
Thiourea compounds such as diafenthiuron,
Organometallic compounds such as azocyclotin, cyhexatin, fenbutatin oxide,
Sulfite ester and diphenyl ether compounds such as propargite,
Diphenylsulfone compounds such as tetradifon,
Pyrrole compounds such as chlorfenapyr, tralopyril,
dinitro compounds such as DNOC,
Nereistoxin analogs such as bensultap, cartap, thiocyclam, thiosultap, thiosultap sodium,
bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron ), benzoylurea compounds such as noviflumuron, teflubenzuron, triflumuron, bistrifluron,
Thiadiazine compounds such as buprofezin,
triazole compounds such as cyromazine,
diacylhydrazine compounds such as chromafenozide, halofenozide, methoxyfenozide, tebufenozide;
Amidine compounds such as amitraz,
Amidinohydrazone compounds such as hydramethylnon,
Naphthoquinone compounds such as acequinocyl,
Strobilurin compounds such as fluacrypyrim, pyriminostrobin, flufenoxystrobin,
Quinazoline compounds such as fenazaquin,
phenoxypyrazoles, such as fenpyroxymate;
Phenoxyethylamine compounds such as pyrimidifen,
Pyridazinone compounds such as pyridaben,
pyrazole carboxamides, such as tebufenpyrad, tolfenpyrad, and pyflubumide;
hydrazine carboxamides, such as metaflumizone;
Tetronic and tetramic acid compounds such as spirodiclofen, spirotetaramat, spiromesifen, spiropidion;
Beta-ketonitriles such as cyflumetofen, cyenopyrafen,
Phthalic acid amide compounds such as flubendiamide,
Anthranils such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole, cyhalodiamide, tetrachlorantraniliprole acid amide compounds,
quinoxaline compounds, such as quinomethionate;
Thiazolidinone compounds such as hexythiazox,
hydrazine compounds such as bifenazate,
Pyridinamine compounds such as flufenerim,
aminoquinazoline compounds, such as pyrifluquinazone;
6-phenoxyquinoline compounds such as flometoquin,
Pyridinylethylbenzamide compounds such as fluopyram,
Sulfonamide compounds such as fluazaindolizine and amidoflumet; Pyridylpyrazole compounds such as tyclopyrazoflor; Oxadiazole compounds such as tioxazafen;
It may be a benzoxazole compound such as oxazosulfyl.
Other insecticides include nicotine, chloropicrin, sulfuryl fluoride, crylotie, clofentezine, diflovidazin, rotenone, and indoxacarb, piperonyl butoxide, chlordimeform, pyridalyl, azadirachtin, benzoxymate, afidopyropen, fluhexafon, fluensulfone, benclothiaz, carzole, insecticidal soap, dimehypo, nithiazine, borate salts, metaldehyde, ryanodine, sulfluramid, acinonapyr ( acynonapyr), benzpyrimoxan, 3-bromo-N-(2,4-dichloro-6-(methylcarbamoyl)phenylyl)-1-(3,5-dichloropyridin-2-yl)-1H -pyrazole-5-carboxamide. Furthermore, the pest control agent according to the present invention can also be used in combination or in combination with microbial pesticides such as entomopathogenic bacteria, entomopathogenic viruses, and entomopathogenic fungi.
用いられる殺菌剤は、例えば、メタラキシル(metalaxyl)、メタラキシル-M(metalaxyl-M)、オキサジキシル(oxadixyl)、オフラセ(ofurase)、ベナラキシル(benalaxyl)、ベナラキシル-M(benalaxyl-M)、キララキシル(kiralaxyl)、オフラース(ofurace)、フララキシル(furalaxyl)、シプロフラン(cyprofuram)のようなフェニルアミド系化合物、
ブプリメート(bupyrimate)、ジメチリモール(dimethilimol)、エチリモール(ethilimol)のようなヒドロキシピリミジン系化合物、
ヒメキサゾール(hymexazole)、ヒドロキシイソキサゾール(hydroxyisoxazole)のようなイソキサゾール系化合物、
オキサチアピプロリン(oxathiapiprolin)のようなピペリジニルチアゾールイソオキサゾリン系化合物、
オクチリノン(octhilinone)のようなイソチアゾロン系化合物、
オキソリニック酸(oxolinic acid)のようなカルボン酸系化合物、
ベノミル(benomyl)、チオファネートメチル(thiophanate-methyl)、カーベンダジム(carbendazole)、フベリダゾール(fuberidazole)、チアベンダゾール(thiabendazole)、デバカルブ(debacarb)のようなベンズイミダゾール・チオファネート系化合物、
ジエトフェンカルブ(diethofencarb)のようなN-フェニルカーバメート系化合物、
ゾキサミド(zoxamide)のようなトルアミド系化合物、
エタボキサム(ethaboxam)のようなエチルアミノチアゾールカルボキサミド系化合物、
ペンシクロン(pencycuron)のようなフェニルウレア系化合物、
フルオピコリド(fluopicolide)、フルオピモミド(fluopimomide)のようなピリジニルメチルベンズアミド系化合物、
ジフルメトリム(diflumetorim)、ブピリメート(bupirimate)、のようなピリミジンアミン系化合物、
ベノダニル(benodanil)、フルトラニル(flutolanil)、メプロニル(mepronil)のようなベンズアニリド系化合物、
イソフェタミド(isofetamid)のようなフェニルオキソエチルチオフェンアミド系化合物、
フルオピラム(fluopyram)のようなピリジニルエチルベンズアミド系化合物、
フェンフラム(fenfuram)のようなフランカルボキサミド系化合物、
オキシカルボキシン(oxycarboxin)、カルボキシン(carboxin)のようなオキサチインカルボキサミド系化合物、
チフルザミド(thifluzamide)のようなチアゾールカルボキサミド系化合物、
フルキサピロキサド(fluxapyroxad)、フラメトピル(furametpyr)、ペンフルフェン(penflufen)、ペンチオピラド(penthiopyrad)、ベンゾビンジフルピル(benzovindiflupyr)、ビキサフェン(bixafen)、イソピラザム(isopyrazam)、セダキサン(sedaxane)、インピルフルキサム(inpyrfluxam) 、フルインダピル(fluindapyr)、イソフルシプラム(isoflucypram)、ピラプロポイン(pyrapropoyne)のようなピラゾール-4-カルボキサミド系化合物、
ボスカリド(boscalid)のようなピリジンカルボキサミド系化合物、
アゾキシストロビン(azoxystrobin)、コウメトキシストロビン(coumetoxystrobin)、クレソキシムメチル(kresoxym-methyl)、トリフロキシストロビン(trifloxystrobin)、ピコキシストロビン(picoxystrobin)、ピラクロストロビン(pyraclostrobin)、ジモキシストロビン(dimoxystrobin)、メトミノストロビン(metominostrobin)、オリサストロビン(orysastrobin)、フルオキサストロビン(fluoxastrobin)、ピラオキシストロビン(pyraoxystrobin)、ピラメトストロビン(pyrametostrobin)、フルフェノキシストロビン(flufenoxystrobin)、フェナミンストロビン(fenaminstrobin)、エノキサストロビン(enoxastrobin)、クモキシストロビン(coumoxystrobin)、マンデストロビン(mandestrobin)、トリクロピリカルブ(triclopyricarb)のようなストロビルリン系化合物、
ファモキサドン(famoxadon)のようなオキサゾリジンジオン系化合物、
フェンアミドン(fenamidone)のようなイミダゾリノン系化合物、
トリクロピリカルブ(triclopyricarab)、ピリベンカルブ(pyribencarb)のようなベンジルカーバメート系化合物、
シアゾファミド(cyazofamid)のようなシアノイミダゾール系化合物、
アミスルブロム(amisulbrom)のようなスルファモイルトリアゾール系化合物、
ビナパクリル(binapacryl)、メプチルジノカルブ(meptyldinocap)、ジノカップ(dinocap)のようなジニトロフェニルクロトン系化合物、
フルアジナム(fluazinam)のような2,6-ジニトロアニリン系化合物、
フェリムゾン(ferimzone)のようなピリミジノンヒドラゾン系化合物、
酢酸-フェンチン(fentin-acetate)、塩化フェンチン(fentin chloride)、水酸化フェンチン(fentin hydroxide)、水酸化トリフェニルスズ(fenthin hydroxide)、酢酸トリフェニルスズ(fenthin acetate)、オキシン銅(oxine copper)のような有機・無機金属系化合物、
シルチオファム(silthiofam)のようなチオフェンカルボキサミド系化合物、
アメトクトラジン(ametoctradin)のようなトリアゾロピリミジンアミン系化合物、
メパニピリム(mepanipyrim)、ニトラピリン(nitrapyrin)、ピリメサニル(pyrimethanil)、シプロジニル(cyprodinil)のようなアニリノピリミジン系化合物、ブラストサイジンS(blasticidin-S)のようなエノピラヌロン酸抗生物質、
カスガマイシン(kasugamycin)、カスガマイシン塩酸塩水和物(kasugamycin hydrochloride hydrate )のようなヘキソピラノシル抗生物質、
ストレプトマイシン(streptomycin)のようなグルコピラノシル抗生物質、
オキシテトラサイクリン(oxytetracycline)のようなテトラサイクリン抗生物質、キノキシフェン(quinoxyfen)のようなアリルオキシキノリン系化合物、
プロキナジド(proquinazid)のようなキナゾリン系化合物、
フルジオキソニル(fludioxonil)、フェンピクロニル(fenpiclonil)のようなシアノピロール系化合物、
フルオロイミド(fluoroimid)、プロシミドン(procymidone)、イプロジオン(iprodione)、ビンクロゾリン(vinchlozolin)のようなジカルボキシイミド系化合物、
エジフェンホス(edifenphos)、イプロベンホス(iprobenfos)、ピラゾホス(pyrazophos)のようなホスホロチオレート系化合物、
イソプロチオラン(isoprothiolane)のようなジチオラン系化合物、
プロパモカルブ(propamocarb)、プロパモカルブ塩酸塩(propamocarb hydrochloride)のようなプロピルカーバメート系化合物、
Bacillus subtilis(QST713、FZB24、MBI600、D747株)のようなBacillus属および産生された殺菌性タンパク類、および、
前記Bt作物により産生された殺菌性タンパク類、
ゴセイカユプテの抽出物のようなテルペン炭化水素類とテルペンアルコール類、
トリホリン(triforine)のようなピペラジン系化合物、
ピリフェノックス(pyrifenox)、ピリソキサゾール(pyrisoxazole)のようなピリジン系化合物、
フェナリモル(fenarimol)、ヌアリモル (nuarimol)のようなピリミジン系化合物、
アザコナゾール(azaconazole)、ブロムコナゾール(bromuconazole)、ジニコナゾール(diniconazole)、ジニコナゾール-M(diniconazole-M)、エポキシコナゾール(epoxyconazole)、フルキンコナゾール(fluquinconazole)、オキスポコナゾール(oxpoconazole)、ペフラゾエート(pefurazoate)、ジフェノコナゾール(difenoconazole)、フェンブコナゾール(fenbuconazole)、イミベンコナゾール(imibenconazole)、イプコナゾール(ipconazole)、メトコナゾール(metconazole)、テトラコナゾール(tetraconazole)、トリアジメホン(triadimefon)、トリアジメノール(triadimenol)、トリチコナゾール(triticonazole)、ウニコナゾール(uniconazole)、イマザリル(imazalil)、ビテルタノール(bitertanol)、トリフルミゾール(triflumizole)、エタコナゾール(etaconazole)、プロピコナゾール(propiconazole)、ペンコナゾール(penconazole)、フルシラゾール(flusilazole)、フルトリアホール(flutriafol)、ミクロブタニル(myclobutanil)、パクロブトラゾール(paclobutrazol)、プロチオコナゾール(prothioconazole)、シプロコナゾール(cyproconazole)、テブコナゾール(tebuconazole)、ヘキサコナゾール(hexaconazole)、プロクロラズ(prochloraz)、シメコナゾール(simeconazole)、イプフェントリフルコナゾール(ipfentrifluconazole)、メフェントリフルコナゾール(mefentrifluconazole)のようなアゾール系化合物、
アルジモルフ(aldimorph)、ドデモルフ(dodemorph)、酢酸ドデモルフ(dodemorph acetate)、トリデモルフ(tridemorph)、フェンプロピモルフ(fenpropimorph)、ジメトモルフ(dimethomorph)、フルモルフ(flumorph)、ピリモルフ(pyrimorph)のようなモルフォリン系化合物、
ピペラリン(piperalin)、フェンプロピディン(fenpropidin)のようなピペリジン系化合物、
スピロキサミン(spiroxamine)のようなスピロケタールアミン系化合物、
フェンヘキサミド(fenhexamid)のようなヒドロキシアニリド系化合物、
フェンピラザミン(fenpyrazamine)のようなアミノピラゾリノン系化合物、
フェルバム(ferbam)、メタム(metam)、メタスルホカルブ(metasulphocarb)、メチラム(metiram)、チラム(thiram)、マンゼブ(mancozeb)、マンネブ(maneb)、ジネブ(zineb)、ジラム(ziram)、ポリカーバメート(polycarbamate)、プロビネブ(propineb)、チウラム(thiuram)、ピリブチカルブ(pyributicarb)のようなチオカーバメート・ジチオカーバメート系化合物、
バリダマイシン(validamycin)のようなグルコピラノシル抗生物質、
ミルジオマイシン(mildiomycin)、ポリオキシン(polyoxin)のようなヌクレオシド系抗生物質、
ベンチアバリカルブ(benthiavalicarb)、ベンチアバリカルブイソプロピル(benthiavalicarb-isopropyl)、バリフェナレート(valifenalate)、イプロバリカルブ(iprovalicarb)のようなバリンアミドカーバメート系化合物、
マンジプロパミド(mandipropamid)のようなマンデル酸アミド系化合物、
フェンピコキサミド(fenpicoxamid)、フロリルピコキサミド(florylpicoxamid)のようなピコリナミド系化合物、
フサライド(fthalide)のようなイソベンゾフラノン系化合物、
ピロキロン(pyroquilone)のようなピロロキノリノン系化合物、
トリシクラゾール(tricyclazole)のようなトリアゾロベンゾチアゾール系化合物、
カルプロパミド(carpropamid)のようなシクロプロパンカルボキサミド系化合物、
ジクロシメット(diclocymet)のようなカルボキサミド系化合物、
フェノキサニル(fenoxanil)のようなプロピオンアミド系化合物、
アシベンゾラルS-メチル(acibenzolar-S-methyl)のようなベンゾチアジアゾール系化合物、
プロベナゾール(probenazole)、ジクロベンチアゾクス(dichlobentiazox)のようなベンゾイソチアゾール系化合物、
チアジニル(tiadinil)のようなチアジアゾールカルボキサミド系化合物、
イソチアニル(isotianil)のようなイソチアゾールカルボキサミド系化合物、
シモキサニル(cymoxanil)のようなシアノアセトアミド=オキシム系化合物、
ホセチル(fosetyl)のようなエチルホスホネート系化合物、
テクロフタラム(techlophthalam)のようなフタラミン酸系化合物、
トリアゾキシド(triazoxide)のようなベンゾトリアジン系化合物、
フルスルファミド(flusulfamide)のようなベンゼンスルホン酸系化合物、
ジクロメジン(diclomezine)のようなピリダジノン系化合物、
シフルフェナミド(cyflufenamide)のようなフェニルアセトアミド系化合物、
メトラフェノン(metrafenopne)のようなベンゾフェノン系化合物、
ピリオフェノン(pyriofenone)のようなベンゾイルピリジン系化合物、
フルチアニル(flutianil)のようなシアノメチレンチアゾリジン系化合物、
テブフロキン(tebufloquin)のような4-キノリル酢酸系化合物、
イプフルフェノキン(ipflufenoquin)のような3-フェノキシキノリン系化合物、
ホセチルアルミニウム(fosetyl-aluminium)、トルクロホス-メチル(tolclofos-methyl)のような有機リン系化合物、
エクロメゾール(echlomezole)のような1,2,4-チアジアゾール系化合物、
トルプロカルブ(tolprocarb)のようなトリフルオロエチルカーバメート系化合物、
ピジフルメトフェン(pydiflumetofen)のようなピラゾールカルボキサミド系化合物、
ボルドー(Bordeaux)混合液、酢酸銅(copper acetate)、塩基性硫酸銅(basic copper sulfate)、オキシ塩化銅(oxy copper chloride)、水酸化第二銅(copper hydroxide)、オキシキノリン銅(oxine-copper)のような銅系化合物、
銅、硫黄のような無機化合物、
キャプタン(captan)、カプタホール(captafol)、フォルペット(folpet)のようなN-ハロゲノチオアルキル系化合物、
アニラジン(anilazine)、クロロタロニル(chlorothalonil)、ジクロロフェン(dichlorophen)、ペンタクロロフェノール(pentachlorophenol)及びその塩、ヘキサクロロベンゼン(hexachlorobenzene)、キントゼン(quintozene)のような有機塩素系化合物、
イミノクタジン酢酸塩(iminoctadine triacetate salt)、イミノクタジンアルベシル酸塩(iminoctadine albesilate)、グアニジン(guanidine)、ドジン(dodine)、ドジン遊離塩基(dodine free base)、グアザチン(guazatine)、グアザチン酢酸塩(guazatine acetate salt)、アルベシレート(albesilate)のようなグアニジン系化合物、
ジチアノン(dithianon)のようなアントラキノン系化合物、
キノメチオネート(quinomethionate)のようなキノキサリン系化合物、
フルオルイミド(fluoroimide)のようなマレイミド系化合物、
トリルフルアニド(tolylfluanid)、ジクロフルアニド(dichlofluanid)のようなスルフェン酸系化合物、
ジノブトン(dinobuton)のようなジニトロフェノール系化合物、
ダゾメット(dazomet)のような環状ジチオカーバメート系化合物
ピラジフルミド(pyraziflumid)のようなアニリド系化合物、
アミノピリフェン(aminopyrifen)のようなニコチン酸エステル系化合物、
メチルテトラプロール(metyltetraprole)のようなテトラゾリノン系化合物、
ピリダクロメチル(pyridachlometyl)のようなピリダジン系化合物
があり得る。
また、その他の殺菌剤として、キノフメリン(quinofumelin)、ジピメチトロン(dipymetitrone)、ピカルブトラゾクス(picarbutrazox)、テクナゼン(tecnazen)、ニトルタール-イソプロピル(nitrthal-isopropyl)、ジシクロメット(dicyclomet)、アシベンゾラル(acibenzolar)、プロヘキサジオン-カルシウム(prohexadione-calcium)、ブロノポール(bronopol)、ジフェニルアミン(diphenylamine)、フルメトベル(flumetover)、ベントキサジン(bethoxazin)、ビフェニル(biphenyl)、クロロネブ(chloroneb)、CNA、ヨードカルブ(iodcarb)、プロチオカルブ(prothiocarb)などが挙げられる。The fungicides used are, for example, metalaxyl, metalaxyl-M, oxadixyl, ofurase, benalaxyl, benalaxyl-M, kiralaxyl. , phenylamide compounds such as ofurace, furalaxyl, cyprofuram,
Hydroxypyrimidine compounds such as bupyrimate, dimethilimol, ethilimol,
Isoxazole compounds such as hymexazole, hydroxyisoxazole,
piperidinylthiazole isoxazoline compounds, such as oxathiapiprolin;
isothiazolone compounds such as octhilinone,
Carboxylic acid compounds such as oxolinic acid,
Benzimidazole-thiophanate compounds such as benomyl, thiophanate-methyl, carbendazole, fuberidazole, thiabendazole, debacarb,
N-phenyl carbamate compounds such as diethofencarb,
toluamide compounds such as zoxamide,
ethylaminothiazole carboxamides, such as ethaboxam;
Phenylurea compounds such as pencycuron,
Pyridinylmethylbenzamide compounds such as fluopicolide, fluopimomide,
pyrimidine amine compounds such as diflumetorim, bupirimate,
Benzanilide compounds such as benodanil, flutolanil, mepronil,
Phenyloxoethylthiophenamide compounds such as isofetamid,
Pyridinylethylbenzamide compounds such as fluopyram,
Furancarboxamides such as fenfuram,
Oxathiin carboxamide compounds such as oxycarboxin, carboxin,
thiazole carboxamides, such as thifluzamide;
fluxapyroxad, furametpyr, penflufen, penthiopyrad, benzovindiflupyr, bixafen, isopyrazam, sedaxane, impirfluxam pyrazole-4-carboxamides such as (inpyrfluxam), fluindapyr, isoflucypram, pyrapropoyne;
Pyridine carboxamide compounds such as boscalid,
azoxystrobin, coumetoxystrobin, kresoxym-methyl, trifloxystrobin, picoxystrobin, pyraclostrobin, dimoxystrobin (dimoxystrobin), metominostrobin, orysastrobin, fluoxastrobin, pyraoxystrobin, pyrametostrobin, flufenoxystrobin, phenaminestrobin Strobilurin compounds such as fenaminstrobin, enoxastrobin, coumoxystrobin, mandestrobin, triclopyricarb,
oxazolidinedione compounds, such as famoxadon;
imidazolinone compounds, such as fenamidone;
Benzyl carbamate compounds such as triclopyricarab, pyribencarb,
cyanoimidazole compounds such as cyazofamid,
sulfamoyltriazole compounds such as amisulbrom,
Dinitrophenylcrotone compounds such as binapacryl, meptyldinocarb, dinocap,
2,6-dinitroaniline compounds such as fluazinam,
pyrimidinone hydrazone compounds such as ferimzone;
fentin-acetate, fentin chloride, fentin hydroxide, fenthin hydroxide, fenthin acetate, oxine copper organic and inorganic metal compounds such as
Thiophene carboxamide compounds such as silthiofam,
triazolopyrimidine amine compounds such as ametoctradin;
Anilinopyrimidine compounds such as mepanipyrim, nitrapyrin, pyrimethanil, cyprodinil, enopyranuronic acid antibiotics such as blasticidin-S,
hexopyranosyl antibiotics, such as kasugamycin, kasugamycin hydrochloride hydrate;
glucopyranosyl antibiotics, such as streptomycin,
tetracycline antibiotics such as oxytetracycline, allyloxyquinoline compounds such as quinoxyfen,
quinazoline compounds such as proquinazid,
Cyanopyrrole compounds such as fludioxonil, fenpiclonil,
dicarboximide compounds such as fluoroimid, procymidone, iprodione, vinchlozolin;
Phosphorothiolate compounds such as edifenphos, iprobenfos, pyrazophos,
dithiolane compounds such as isoprothiolane,
Propyl carbamate compounds such as propamocarb, propamocarb hydrochloride,
Bacillus genus and produced bactericidal proteins, such as Bacillus subtilis (strains QST713, FZB24, MBI600, D747), and
fungicidal proteins produced by the Bt crop;
Terpene hydrocarbons and terpene alcohols, such as Gosei Kayupte extract;
Piperazine compounds such as triforine,
Pyridine compounds such as pyrifenox, pyrisoxazole,
Pyrimidine compounds such as fenarimol, nuarimol,
azaconazole, bromuconazole, diniconazole, diniconazole-M, epoxyconazole, fluquinconazole, oxpoconazole, pefrazoate ( pefurazoate), difenoconazole, fenbuconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triadimefon, triadimenol , triticonazole, uniconazole, imazalil, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole ), flutriafol, myclobutanil, paclobutrazol, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz ( azole compounds such as prochloraz), simeconazole, ipfentrifluconazole, mefentrifluconazole;
Morpholine compounds such as aldimorph, dodemorph, dodemorph acetate, tridemorph, fenpropimorph, dimethomorph, flumorph, pyrimorph ,
piperidine compounds such as piperalin and fenpropidin;
spiroketal amine compounds, such as spiroxamine;
Hydroxyanilide compounds such as fenhexamid,
aminopyrazolinone compounds such as fenpyrazamine,
Ferbam, metam, metasulphocarb, metiram, thiram, mancozeb, maneb, zineb, ziram, polycarbamate ( thiocarbamate/dithiocarbamate compounds such as polycarbamate, propineb, thiuram, pyributicarb;
glucopyranosyl antibiotics, such as validamycin,
nucleoside antibiotics such as mildiomycin, polyoxin,
Valinamide carbamate compounds such as benthiavalicarb, benthiavalicarb-isopropyl, valifenalate, iprovalicarb,
mandelic acid amide compounds such as mandipropamid,
picolinamide compounds such as fenpicoxamide, florylpicoxamide,
Isobenzofuranone compounds such as fthalide,
Pyrroloquinolinone compounds, such as pyroquilone,
triazolobenzothiazole compounds such as tricyclazole;
Cyclopropane carboxamide compounds such as carpropamid,
carboxamides, such as diclocymet;
Propionamide compounds such as fenoxanil,
benzothiadiazole compounds such as acibenzolar-S-methyl,
benzisothiazole compounds such as probenazole and dichlobentiazox;
thiadiazole carboxamides, such as tiadinil;
isothiazole carboxamide compounds such as isotianil,
Cyanoacetamide oxime compounds such as cymoxanil,
Ethylphosphonate compounds such as fosetyl,
Phthalamic acid compounds such as techlophthalam,
benzotriazine compounds such as triazoxide,
benzenesulfonic acid compounds such as flusulfamide,
Pyridazinone compounds such as diclomezine,
Phenylacetamide compounds such as cyflufenamide,
benzophenone compounds such as metrafenopne;
benzoylpyridine compounds such as pyriofenone,
cyanomethylenethiazolidine compounds, such as flutianil;
4-quinolyl acetic acid compounds such as tebufloquin,
3-phenoxyquinoline compounds such as ipflufenoquin,
Organophosphorus compounds such as fosetyl-aluminium, tolclofos-methyl,
1,2,4-thiadiazole compounds such as echlomezole,
trifluoroethyl carbamate compounds such as tolprocarb,
pyrazole carboxamides, such as pydiflumetofen;
Bordeaux mixture, copper acetate, basic copper sulfate, oxy copper chloride, copper hydroxide, oxine-copper ), copper-based compounds such as
inorganic compounds such as copper and sulfur;
N-halogenothioalkyl compounds such as captan, captafol, folpet,
Organochlorine compounds such as anilazine, chlorothalonil, dichlorophen, pentachlorophenol and its salts, hexachlorobenzene, quintozene,
iminoctadine triacetate salt, iminoctadine albesilate, guanidine, dodine, dodine free base, guazatine, guazatine acetate salt ), guanidine compounds such as albesilate,
anthraquinone compounds such as dithianon,
quinoxaline compounds, such as quinomethionate;
maleimide compounds such as fluorimide,
sulfenic acid compounds such as tolylfluanid and dichlofluanid;
Dinitrophenol compounds such as dinobuton,
Cyclic dithiocarbamate compounds such as dazomet; anilide compounds such as pyraziflumid;
nicotinic acid ester compounds such as aminopyrifen;
Tetrazolinone compounds such as methyltetraprole,
Possible compounds include pyridazine compounds such as pyridachlomethyl.
Other fungicides include quinofumelin, dipymetitrone, picarbutrazox, tecnazen, nitrthal-isopropyl, dicyclomet, acibenzolar, prohexadione-calcium, bronopol, diphenylamine, flumetover, bethoxazin, biphenyl, chloroneb, CNA, iodcarb, prothiocarb ( prothiocarb), etc.
本発明の化合物またはその農園芸上許容可能な酸付加塩は、その有効量を、植物、土壌に適用することにより、対象の有害生物の防除に使用することができる。その製剤中の有効成分量は0.01~90重量%である。水和剤、乳剤、懸濁剤、フロアブル剤、水溶剤、および顆粒水和剤は水で所望の濃度に希釈して、溶解液、懸濁液あるいは乳濁液の状態で、粉剤・粒剤はそのままで、植物あるいは土壌に散布することができる。また、本発明の化合物またはその農園芸上許容可能な酸付加塩を防疫用として使用する場合には、乳剤、水和剤、フロアブル剤等は水で所望の濃度に希釈して施用することができ、油剤、エアゾール、煙霧剤、毒餌、防ダニシート等はそのまま使用することができる。
本願明細書において、「作物」とは栽培植物全般を指し、具体的には食用作物、飼料作物、緑肥作物、園芸作物(観賞植物を含む)、及び工芸作物を指す。
本発明は作物の活力を高める方法も含み、当該方法は本発明の化合物に作物若しくは作物の種子を接触させる工程を含む。また、本発明は作物の種子の製造方法も含み、当該方法は本発明の化合物に作物の種子を処理する工程を含む。
処理又は接触の対象が種子である場合、本発明の化合物またはその農園芸上許容可能な酸付加塩の量は限定されないが、処理後の種子重量に対し、有効成分量として約0.0001~約50重量%の量で本発明の化合物またはその農園芸上許容可能な酸付加塩が含まれることが好ましい。
本発明によりさらに、本発明の化合物またはその酸付加塩の、動物・鳥類を動物寄生性害虫から保護する組成物の有効成分としての使用が提供される。該組成物は、本発明の化合物またはその酸付加塩を、殺寄生虫的に有効でありかつ対象である動物・鳥類に害を与えない量で、含む。本発明の化合物またはその酸付加塩は、有害生物またはその生育環境-例えば動物・鳥類、作物、作物の種子、土壌など-に生物学的に有効な量で接触され、有害無脊椎生物を防除する。The compound of the present invention or its agriculturally and horticulturally acceptable acid addition salt can be used to control target pests by applying an effective amount thereof to plants and soil. The amount of active ingredient in the formulation is 0.01-90% by weight. Wettable powders, emulsions, suspensions, flowables, water-solvents, and granules Wettable powders can be diluted with water to the desired concentration to form powders or granules in the form of solutions, suspensions, or emulsions. can be applied directly to plants or to the soil. Furthermore, when using the compound of the present invention or its agriculturally and horticulturally acceptable acid addition salt for epidemic prevention purposes, emulsions, wettable powders, flowable preparations, etc. may be diluted with water to the desired concentration before application. Oils, aerosols, fogs, poison baits, anti-mite sheets, etc. can be used as they are.
In the present specification, "crops" refers to cultivated plants in general, and specifically refers to food crops, feed crops, green manure crops, horticultural crops (including ornamental plants), and craft crops.
The present invention also includes a method of increasing crop vigor, which method comprises contacting a crop or crop seed with a compound of the invention. The present invention also includes a method for producing crop seeds, which method includes treating crop seeds with a compound of the present invention.
When the object of treatment or contact is seeds, the amount of the compound of the present invention or its agriculturally and horticulturally acceptable acid addition salt is not limited, but the amount of active ingredient is about 0.0001 to 0.0001 to the weight of the seeds after treatment. Preferably, the compound of the invention or an agronomically acceptable acid addition salt thereof is included in an amount of about 50% by weight.
The present invention further provides the use of a compound of the present invention or an acid addition salt thereof as an active ingredient of a composition for protecting animals and birds from animal parasitic pests. The composition contains the compound of the present invention or an acid addition salt thereof in an amount that is parasicidally effective and does not harm the target animals or birds. The compound of the present invention or its acid addition salt is brought into contact with harmful organisms or their growing environment, such as animals/birds, crops, crop seeds, soil, etc., in a biologically effective amount to control harmful invertebrates. do.
次に、本発明化合物の具体例を以下に示す。
式(1)のG1がG1-1である式(1-3)において、R1、R2、R3、R4、A1、A2が表1に記載の置換基であり、Dが表2に記載の置換基であり、Eが表3に記載の置換基であり、RAが表4に記載の置換基であり、RB、RD、REが表5に記載の置換基である組み合わせの本発明化合物。
式(1)のG1がG1-1である式(1-3)において、R1、R2、R3、R4、A1、A2が表6に記載の置換基であり、Dが表2に記載の置換基であり、Eが表3に記載の置換基であり、RAが表4に記載の置換基であり、RB、RC、RDが表7に記載の置換基である組み合わせの本発明化合物。
式(2)のG2がG2-1である式(2-1)において、R1、R2、R3、R4、A1、A2が表1に記載の置換基であり、RAが表4に記載の置換基であり、RB、RD、REが表5に記載の置換基である組み合わせの本発明化合物。
式(2)のG2がG2-1である式(2-1)において、R1、R2、R3、R4、A1、A2が表6に記載の置換基であり、RAが表4に記載の置換基であり、RB、RC、RDが表7に記載の置換基である組み合わせの本発明化合物。In formula (2-1) in which G 2 in formula (2) is G 2 -1, R 1 , R 2 , R 3 , R 4 , A 1 and A 2 are the substituents listed in Table 6, A compound of the present invention in which R A is a substituent listed in Table 4, and R B , R C , and R D are substituents listed in Table 7.
式(3)のG2がG2-1である式(3-1)において、R1、R2、R3、R4、A1、A2が表1に記載の置換基であり、RAが表4に記載の置換基であり、RB、RD、REが表5に記載の置換基である組み合わせの本発明化合物。
式(3)のG2がG2-1である式(3-1)において、R1、R2、R3、R4、A1、A2が表6に記載の置換基であり、RAが表4に記載の置換基であり、RB、RC、RDが表7に記載の置換基である組み合わせの本発明化合物。In formula (3-1) in which G 2 of formula (3) is G 2 -1, R 1 , R 2 , R 3 , R 4 , A 1 and A 2 are the substituents listed in Table 6, A compound of the present invention in which R A is a substituent listed in Table 4, and R B , R C , and R D are substituents listed in Table 7.
<合成実施例>
以下、実施例を挙げて本発明を具体的に説明するが、本発明はこれらの実施例に限定されるものではない。NMRデータの「s」はシングレット(一重線)、「d」はダブレット(二重線)、「t」はトリプレット(三重線)、「q」はカルテット(四重線)、「m」はマルチプレット(多重線)、「broad」はブロード(幅広線)を示し、Jは結合定数を示す。<Synthesis Examples>
EXAMPLES Hereinafter, the present invention will be specifically explained with reference to Examples, but the present invention is not limited to these Examples. In NMR data, "s" stands for singlet, "d" stands for doublet, "t" stands for triplet, "q" stands for quartet, and "m" stands for multiple. Plets (multiple lines), "broad" indicates broad, and J indicates binding constant.
合成実施例1-1-1:3-(1H-ピラゾール-1-イル)イソニコチノニトリルの調製
3-クロロイソニコチノニトリル(1.00g、7.22mmol)、1H-ピラゾール(0.52g、7.94mmmol)をN,N-ジメチルホルムアミド(10ml)に溶解させ、氷浴で冷却し、水素化ナトリウム(0.35g、7.94mmol)を加えた後、室温で1.5時間撹拌した。水を加え、酢酸エチルで3回抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.79g、64.2%、白色個体)を得た。
1H NMR(CDCl3) δ9.17(1H, s), 8.71(1H, s, J=5.1Hz), 8.17(1H, d, J=2.7Hz), 7.88(1H, d, J=1.5Hz), 7.65(1H, dd, J=5.1, 0.6Hz), 6.62(1H, dd, J=2.7, 0.6Hz)Synthesis Example 1-1-1: Preparation of 3-(1H-pyrazol-1-yl)isonicotinonitrile 3-chloroisonicotinonitrile (1.00 g, 7.22 mmol), 1H-pyrazole (0.52 g , 7.94 mmol) was dissolved in N,N-dimethylformamide (10 ml), cooled in an ice bath, added with sodium hydride (0.35 g, 7.94 mmol), and stirred at room temperature for 1.5 hours. . Water was added and extracted three times with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.79 g, 64.2%, white solid).
1H NMR(CDCl 3 ) δ9.17(1H, s), 8.71(1H, s, J=5.1Hz), 8.17(1H, d, J=2.7Hz), 7.88(1H, d, J=1.5Hz) , 7.65(1H, dd, J=5.1, 0.6Hz), 6.62(1H, dd, J=2.7, 0.6Hz)
合成実施例1-1-2:3-(1H-ピラゾール-1-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)イソニコチンイミダミド(化合物番号5)の調製
5-(トリフルオロメチル)ピリジン-2-アミン(0.52g、3.23mmol)をN,N-ジメチルホルムアミド(15mL)に溶解させ、水素化ナトリウム(含量55%、0.14g、3.23mmol)を加え、室温で30分間撹拌した。そこに合成実施例1-1-1で調製した3-(1H-ピラゾール-1-イル)イソニコチノニトリル(0.50g、2.94mmol)を加え、同温度で一時間撹拌した後、水素化ナトリウム(含量55%、0.05g、1.15mmol)を追加し、同温度でさらに17時間撹拌した。水を加え、酢酸エチルで3回抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.57g、58.6%、白色固体)を得た。
1H NMR(CDCl3) δ10.36(1H, broad), 8.90-8.70(2H, m), 8.55(1H, s), 7.95-7.81(2H, m), 7.81-7.70(2H, m), 7.24(1H, d, J=9.0Hz), 6.49(1H, broad), 6.53(1H, t, J=2.1Hz)Synthesis Example 1-1-2: Preparation of 3-(1H-pyrazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)isonicotinimidamide (Compound No. 5) 5- (Trifluoromethyl)pyridin-2-amine (0.52 g, 3.23 mmol) was dissolved in N,N-dimethylformamide (15 mL), and sodium hydride (content 55%, 0.14 g, 3.23 mmol) was dissolved in N,N-dimethylformamide (15 mL). The mixture was added and stirred at room temperature for 30 minutes. 3-(1H-pyrazol-1-yl)isonicotinonitrile (0.50 g, 2.94 mmol) prepared in Synthesis Example 1-1-1 was added thereto, and after stirring at the same temperature for 1 hour, hydrogen Sodium chloride (content 55%, 0.05 g, 1.15 mmol) was added, and the mixture was further stirred at the same temperature for 17 hours. Water was added and extracted three times with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.57 g, 58.6%, white solid).
1H NMR(CDCl 3 ) δ10.36(1H, broad), 8.90-8.70(2H, m), 8.55(1H, s), 7.95-7.81(2H, m), 7.81-7.70(2H, m), 7.24 (1H, d, J=9.0Hz), 6.49(1H, broad), 6.53(1H, t, J=2.1Hz)
合成実施例1-1-3:N-((3-(1H-ピラゾール-1-イル)ピリジン-4-イル)((5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号14)の調製
合成実施例1-1-2で調製した3-(1H-ピラゾール-1-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)イソニコチンイミダミド(0.30g、0.90mmol)に無水酢酸(6mL)を加え、還流下、15分間撹拌した。同温度で無水酢酸を減圧留去し、得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.26g、76.9%、白色粘性物)を得た。
1H NMR(CDCl3) δ12.90(1H, s), 8.77(1H, s), 8.77-8.63(2H, m), 7.99(1H, d, J=7.8Hz), 7.76(1H, d, J=1.8Hz), 7.69(1H, s), 7.53(1H, d, J=4.8Hz), 7.38(1H, d, J=8.4Hz), 6.44(1H, s), 1.96(3H, s)Synthesis Example 1-1-3: N-((3-(1H-pyrazol-1-yl)pyridin-4-yl)((5-(trifluoromethyl)pyridin-2-yl)amino)methylene)acetamide Preparation of (Compound No. 14) 3-(1H-pyrazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)isonicotinimidamide prepared in Synthesis Example 1-1-2 (0.30 g, 0.90 mmol) was added with acetic anhydride (6 mL), and the mixture was stirred under reflux for 15 minutes. Acetic anhydride was distilled off under reduced pressure at the same temperature, and the resulting crude product was purified by silica gel chromatography to obtain the desired product (0.26 g, 76.9%, white viscous material).
1H NMR(CDCl 3 ) δ12.90(1H, s), 8.77(1H, s), 8.77-8.63(2H, m), 7.99(1H, d, J=7.8Hz), 7.76(1H, d, J =1.8Hz), 7.69(1H, s), 7.53(1H, d, J=4.8Hz), 7.38(1H, d, J=8.4Hz), 6.44(1H, s), 1.96(3H, s)
合成実施例1-1-4: N-((3-(1H-ピラゾール-1-イル)ピリジン-4-イル)(メチル(5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号17)の調製
合成実施例1-1-3で調製したN-((3-(1H-ピラゾール-1-イル)ピリジン-4-イル)((5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(0.13g、0.35mmol)をN,N-ジメチルホルムアミド(2.6mL)に溶解させ、水素化ナトリウム(含量55%、0.02g、0.41mmol)を加え、室温で10分間撹拌した。そこにヨウ化メチル(25μL、0.40mmol)を加え、同温度で3時間撹拌した後、水を加え、酢酸エチルで2回抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(8.8mg、6.5%、黄色粘性物)を得た。
1H NMR(CDCl3) δ8.70(1H, s), 8.56(1H, s), 8.43(1H, s), 7.30-7.20(2H, m), 7.91(1H, d, J=2.7Hz), 7.74(1H, d, J=1.5Hz), 7.67(1H, dd, J=8.7, 2.4Hz), 6.49(1H, t, J=2.4Hz), 3.44(3H, s), 1.89(3H, s)Synthesis Example 1-1-4: N-((3-(1H-pyrazol-1-yl)pyridin-4-yl)(methyl(5-(trifluoromethyl)pyridin-2-yl)amino)methylene) Preparation of acetamide (compound number 17) N-((3-(1H-pyrazol-1-yl)pyridin-4-yl)((5-(trifluoromethyl)pyridine) prepared in Synthesis Example 1-1-3 -2-yl)amino)methylene)acetamide (0.13 g, 0.35 mmol) was dissolved in N,N-dimethylformamide (2.6 mL), and sodium hydride (content 55%, 0.02 g, 0.41 mmol) was dissolved in N,N-dimethylformamide (2.6 mL). ) and stirred at room temperature for 10 minutes. After adding methyl iodide (25 μL, 0.40 mmol) there and stirring at the same temperature for 3 hours, water was added and extracted twice with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, filtered, and then was distilled off under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (8.8 mg, 6.5%, yellow viscous material).
1H NMR(CDCl 3 ) δ8.70(1H, s), 8.56(1H, s), 8.43(1H, s), 7.30-7.20(2H, m), 7.91(1H, d, J=2.7Hz), 7.74(1H, d, J=1.5Hz), 7.67(1H, dd, J=8.7, 2.4Hz), 6.49(1H, t, J=2.4Hz), 3.44(3H, s), 1.89(3H, s )
合成実施例1-1-5: N,N’-ジメチル-3-(1H-ピラゾール-1-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)イソニコチンイミダミド(化合物番号20)の調製
合成実施例1-1-2で調製したN-((3-(1H-ピラゾール-1-イル)ピリジン-4-イル)((5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(0.15g、0.45mmol)をN,N-ジメチルホルムアミド(3mL)に溶解させ、水素化ナトリウム(含量55%、22mg、0.50mmol)を加え、室温で10分間撹拌した後、ヨウ化メチル(30μL、0.40mmol)を加え、同温度で30分撹拌した。さらに水素化ナトリウム(含量55%、22mg、0.50mmol)を加え、室温で10分間撹拌した後、にヨウ化メチル(30μL、0.40mmol)を加え、同温度で2.5時間撹拌した。水を加え、酢酸エチルで2回抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(31mg、18.8%、白色固体)を得た。
8.90(1H, s), 8.45(1H, d, J=4.8Hz), 8.29(1H, d, J=2.4Hz), 8.16(1H, s), 7.78(1H, d, J=1.5Hz), 1H NMR(CDCl3) δ7.59(1H, dd, J=8.4, 2.4Hz), 7.03(1H, d, J=4.8Hz), 6.78(1H, d, J=8.4Hz), 6.48(1H, t, J=2.1Hz), 3.12(3H, s), 2.57(3H, s)Synthesis Example 1-1-5: N,N'-dimethyl-3-(1H-pyrazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)isonicotinimidamide (compound Preparation of No. 20) N-((3-(1H-pyrazol-1-yl)pyridin-4-yl)((5-(trifluoromethyl)pyridin-2- yl)amino)methylene)acetamide (0.15 g, 0.45 mmol) was dissolved in N,N-dimethylformamide (3 mL), sodium hydride (content 55%, 22 mg, 0.50 mmol) was added, and the mixture was heated for 10 min at room temperature. After stirring for a minute, methyl iodide (30 μL, 0.40 mmol) was added, and the mixture was stirred at the same temperature for 30 minutes. Further, sodium hydride (content 55%, 22 mg, 0.50 mmol) was added, and the mixture was stirred at room temperature for 10 minutes, followed by addition of methyl iodide (30 μL, 0.40 mmol), and stirred at the same temperature for 2.5 hours. Water was added, extracted twice with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (31 mg, 18.8%, white solid).
8.90(1H, s), 8.45(1H, d, J=4.8Hz), 8.29(1H, d, J=2.4Hz), 8.16(1H, s), 7.78(1H, d, J=1.5Hz), 1H NMR(CDCl 3 ) δ7.59(1H, dd, J=8.4, 2.4Hz), 7.03(1H, d, J=4.8Hz), 6.78(1H, d, J=8.4Hz), 6.48(1H, t, J=2.1Hz), 3.12(3H, s), 2.57(3H, s)
合成実施例1-1-6:3-(2H-1,2,3-トリアゾール-2-イル)イソニコチノニトリルの調製
3-クロロイソニコチノニトリル(1.50g、7.22mmol)、1H-1,2,3-トリアゾール(1.50g、14.44mmol)をジメチルスルホキシド(20mL)に溶解させ、水浴で冷却し、水素化ナトリウム(0.98g、21.77mmol)を加えた後、100℃で2時間撹拌した。水を加え、酢酸エチルで4回抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、3-(2H-1,2,3-トリアゾール-2-イル)イソニコリノニトリル(0.92g、49.8%)と3-(1H-1,2,3-トリアゾール-1-イル)イソニコチノニトリル(0.92g、9.6%)を得た。
3-(2H-1,2,3-トリアゾール-2-イル)イソニコリノニトリル
1H NMR(CDCl3) δ9.50(1H, s), 8.77(1H, d, J=4.8Hz), 8.00(2H, s), 7.71(1H, d, J=5.1Hz)
3-(1H-1,2,3-トリアゾール-1-イル)イソニコチノニトリル
1H NMR(CDCl3) δ9.25(1H, s), 8.92(1H, d, J=5.1Hz), 8.29(1H, d, J=1.2Hz), 7.98(1H, d, J=1.2Hz), 7,76(1H, d, 5,1Hz)Synthesis Example 1-1-6: Preparation of 3-(2H-1,2,3-triazol-2-yl)isonicotinonitrile 3-chloroisonicotinonitrile (1.50 g, 7.22 mmol), 1H -1,2,3-triazole (1.50 g, 14.44 mmol) was dissolved in dimethyl sulfoxide (20 mL), cooled in a water bath, and sodium hydride (0.98 g, 21.77 mmol) was added, followed by 100 g. Stirred at ℃ for 2 hours. Water was added and extracted four times with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography, and 3-(2H-1,2,3-triazol-2-yl)isonicolinonitrile (0.92 g, 49.8%) and 3-(1H -1,2,3-triazol-1-yl)isonicotinonitrile (0.92 g, 9.6%) was obtained.
3-(2H-1,2,3-triazol-2-yl)isonicolinonitrile
1H NMR(CDCl 3 ) δ9.50(1H, s), 8.77(1H, d, J=4.8Hz), 8.00(2H, s), 7.71(1H, d, J=5.1Hz)
3-(1H-1,2,3-triazol-1-yl)isonicotinonitrile
1H NMR(CDCl 3 ) δ9.25(1H, s), 8.92(1H, d, J=5.1Hz), 8.29(1H, d, J=1.2Hz), 7.98(1H, d, J=1.2Hz) , 7,76(1H, d, 5,1Hz)
合成実施例1-1-7:3-(2H-1,2,3-トリアゾール-2-イル)-N-(5-トリフルオロメチル)ピリジン-2-イル)イソニコチンイミダミド(化合物番号7)の調製
5-(トリフルオロメチル)ピリジン-2-アミン(0.57g、3.51mmol)をN,N-ジメチルホルムアミド(12mL)に溶解させ、水素化ナトリウム(含量55%、0.17g、3.86mmol)を加え、室温で1時間撹拌した。そこに合成実施例1-1-6で調製した3-(2H-1,2,3-トリアゾール-2-イル)イソニコチノニトリル(0.60g、3.51mmol)を加え、室温で13時間撹拌した。水を加え、酢酸エチルで2回抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.74g、63.3%)を得た。
1H NMR(CDCl3) δ10.34(1H, broad), 9.08(1H, s), 8.80(1H, d, J=4.8Hz), 8.57(1H, s), 7.86(2H, s), 7.81(1H, dd, J=8.4, 2.4Hz), 7.54(1H, d, J=5.1Hz), 7.14(1H, d, J=8.7Hz), 6.23(1H, broad)Synthesis Example 1-1-7: 3-(2H-1,2,3-triazol-2-yl)-N-(5-trifluoromethyl)pyridin-2-yl)isonicotinimidamide (Compound No. 7 ) Preparation of 5-(trifluoromethyl)pyridin-2-amine (0.57 g, 3.51 mmol) was dissolved in N,N-dimethylformamide (12 mL), and sodium hydride (content 55%, 0.17 g, 3.86 mmol) was added thereto, and the mixture was stirred at room temperature for 1 hour. 3-(2H-1,2,3-triazol-2-yl)isonicotinonitrile (0.60 g, 3.51 mmol) prepared in Synthesis Example 1-1-6 was added thereto, and the mixture was kept at room temperature for 13 hours. Stirred. Water was added and extracted twice with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.74 g, 63.3%).
1H NMR(CDCl 3 ) δ10.34(1H, broad), 9.08(1H, s), 8.80(1H, d, J=4.8Hz), 8.57(1H, s), 7.86(2H, s), 7.81( 1H, dd, J=8.4, 2.4Hz), 7.54(1H, d, J=5.1Hz), 7.14(1H, d, J=8.7Hz), 6.23(1H, broad)
合成実施例1-1-8:N-((3-(2H-1,2,3-トリアゾール-2-イル)ピリジン-4-イル)((5-(トリフルオロメチル)ピリジン-2-イル)アミノ)メチレン)アセタミド(化合物番号16)の調製
合成実施例1-1-7で調製した3-(2H-1,2,3-トリアゾール-2-イル)-N-(5-トリフルオロメチル)ピリジン-2-イル)イソニコチンイミダミド(0.36g、1.08mmol)に無水酢酸(7mL)を加え、還流下、20分間撹拌した。同温度で無水酢酸を減圧留去し、得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.26g、63.6%、白色固体)を得た。
1H NMR(CDCl3) δ13.33(1H, s), 9.34(1H, s), 8.76(1H, s), 8.71(1H, d, J=5.1Hz), 7.97(1H, d, J=6.9Hz), 7.78(2H, s), 7.43(1H, d, J=5.1Hz), 7.32(1H, d, J=8.4Hz), 2.09(3H, s)Synthesis Example 1-1-8: N-((3-(2H-1,2,3-triazol-2-yl)pyridin-4-yl)((5-(trifluoromethyl)pyridin-2-yl) ) Amino)methylene)acetamide (Compound No. 16) Preparation of 3-(2H-1,2,3-triazol-2-yl)-N-(5-trifluoromethyl) prepared in Synthesis Example 1-1-7 ) Pyridin-2-yl) isonicotinimidamide (0.36 g, 1.08 mmol) was added acetic anhydride (7 mL) and stirred under reflux for 20 minutes. Acetic anhydride was distilled off under reduced pressure at the same temperature, and the resulting crude product was purified by silica gel chromatography to obtain the desired product (0.26 g, 63.6%, white solid).
1H NMR(CDCl 3 ) δ13.33(1H, s), 9.34(1H, s), 8.76(1H, s), 8.71(1H, d, J=5.1Hz), 7.97(1H, d, J=6.9 Hz), 7.78(2H, s), 7.43(1H, d, J=5.1Hz), 7.32(1H, d, J=8.4Hz), 2.09(3H, s)
合成実施例1-2-1:2-(3-(1H-ピラゾール-1-イル)ピリジン-4-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号46)の調製
合成実施例1-1-2で調製した3-(1H-ピラゾール-1-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)イソニコチンイミダミド(0.20g、0.60mmol)をジクロロメタン(10mL)に溶解させ、ヨードベンゼンジアセテート(0.23g、0.72mmol)を加え、室温で2時間撹拌した。ヨードベンゼンジアセテート(0.23g、0.72mmol)をさらに加え、室温で5時間撹拌した。ジクロロメタンをエバポレーターで減圧留去した後、得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.12g、61.3%、白色個体)を得た。
1H NMR(CDCl3) δ8.88(1H, s), 8.86-8.77(2H, m), 8.07(1H, d, J=4.8Hz), 7.84(1H, d, J=9.3Hz), 7.75-7.64(3H, m), 6.49(1H, t, J=2.4Hz)Synthesis Example 1-2-1: 2-(3-(1H-pyrazol-1-yl)pyridin-4-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5 -a] Preparation of pyridine (compound number 46) 3-(1H-pyrazol-1-yl)-N-(5-(trifluoromethyl)pyridin-2-yl) prepared in Synthesis Example 1-1-2 Isonicotinimidamide (0.20 g, 0.60 mmol) was dissolved in dichloromethane (10 mL), iodobenzenediacetate (0.23 g, 0.72 mmol) was added, and the mixture was stirred at room temperature for 2 hours. Iodobenzenediacetate (0.23 g, 0.72 mmol) was further added and stirred at room temperature for 5 hours. After dichloromethane was distilled off under reduced pressure using an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the desired product (0.12 g, 61.3%, white solid).
1H NMR(CDCl 3 ) δ8.88(1H, s), 8.86-8.77(2H, m), 8.07(1H, d, J=4.8Hz), 7.84(1H, d, J=9.3Hz), 7.75- 7.64(3H, m), 6.49(1H, t, J=2.4Hz)
合成実施例1-2-2:2-(3-(2H-1,2,3-トリアゾール-2-イル)ピリジン-4-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号48)の調製
合成実施例1-1-7で調製した3-(2H-1,2,3-トリアゾール-2-イル)-N-(5-トリフルオロメチル)ピリジン-2-イル)イソニコチンイミダミド(0.14g、0.75mmol)をジクロロメタン(7mL)に溶解させ、ヨードベンゼンジアセテート(0.16g、0.49mmol)を加え、室温で45分間撹拌した。水をを加え、酢酸エチルで2度抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.10g、74.1%)を得た。
1H NMR(CDCl3) δ9.03(1H, s), 8.89(1H, d, J=5.1Hz), 8.80(1H, s), 8.10(1H, d, J=5.1Hz), 7.85(2H, s), 7.82(1H, d, J=9.3Hz), 7.69(1H, dd, J=9.3, 1.8Hz)Synthesis Example 1-2-2: 2-(3-(2H-1,2,3-triazol-2-yl)pyridin-4-yl)-6-(trifluoromethyl)-[1,2,4 ] Preparation of triazolo[1,5-a]pyridine (compound number 48) 3-(2H-1,2,3-triazol-2-yl)-N-(5 -Trifluoromethyl)pyridin-2-yl)isonicotinimidamide (0.14 g, 0.75 mmol) was dissolved in dichloromethane (7 mL), and iodobenzenediacetate (0.16 g, 0.49 mmol) was added, and the mixture was heated to room temperature. The mixture was stirred for 45 minutes. Water was added, extracted twice with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.10 g, 74.1%).
1H NMR(CDCl 3 ) δ9.03(1H, s), 8.89(1H, d, J=5.1Hz), 8.80(1H, s), 8.10(1H, d, J=5.1Hz), 7.85(2H, s), 7.82(1H, d, J=9.3Hz), 7.69(1H, dd, J=9.3, 1.8Hz)
合成実施例1-3-1:2-(3-(1H-ピラゾール-1-イル)ピリジン-4-イル)-7-(トリフルオロメチル)-4H-ピリド[1,2-a][1,3,5]トリアジン-4-オン(化合物番号61)の調製
合成実施例1-1-2で調製した3-(1H-ピラゾール-1-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)イソニコチンイミダミド(0.18g、0.54mmol)をジクロロメタン(8mL)に溶解させ、クロロギ酸4-クロロフェニル(200μL、1.45mmol)、続いてトリエチルアミン(400μL、5.42mmol)を加え、室温で1時間撹拌した。その後、エバポレーターでジクロロメタンを留去し、酢酸エチル(10mL)を加え、加熱還流下、4時間撹拌した。エバポレーターで酢酸エチルを減圧留去した後、得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.16g、84.6%、白色個体)を得た。
1H NMR(CDCl3) δ9.37(1H, s), 8.87(1H, s), 8.11(1H, d, J=4.8Hz), 8.10(1H, dd, J=9.0, 2.4Hz), 7.94(1H, d, J=5.1Hz), 7.80(1H, d, J=2.4Hz), 7.58(1H, d, J=1.8Hz), 7.52(1H, d, J=9.3Hz), 6.46(1H, t, J=2.1Hz)Synthesis Example 1-3-1: 2-(3-(1H-pyrazol-1-yl)pyridin-4-yl)-7-(trifluoromethyl)-4H-pyrido[1,2-a][1 , 3, 5] Preparation of triazin-4-one (compound number 61) 3-(1H-pyrazol-1-yl)-N-(5-(trifluoromethyl) prepared in Synthesis Example 1-1-2 Pyridin-2-yl) isonicotinimidamide (0.18 g, 0.54 mmol) was dissolved in dichloromethane (8 mL), followed by 4-chlorophenyl chloroformate (200 μL, 1.45 mmol) followed by triethylamine (400 μL, 5.42 mmol). ) and stirred at room temperature for 1 hour. Thereafter, dichloromethane was distilled off using an evaporator, ethyl acetate (10 mL) was added, and the mixture was stirred under heating under reflux for 4 hours. After ethyl acetate was distilled off under reduced pressure using an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the desired product (0.16 g, 84.6%, white solid).
1H NMR(CDCl 3 ) δ9.37(1H, s), 8.87(1H, s), 8.11(1H, d, J=4.8Hz), 8.10(1H, dd, J=9.0, 2.4Hz), 7.94( 1H, d, J=5.1Hz), 7.80(1H, d, J=2.4Hz), 7.58(1H, d, J=1.8Hz), 7.52(1H, d, J=9.3Hz), 6.46(1H, t, J=2.1Hz)
合成実施例1-3-2:2-(3-(2H-1,2,3-トリアゾール-2-イル)ピリジン-4-イル)-7-(トリフルオロメチル)-4H-ピリド[1,2-a][1,3,5]トリアジン-4-オン(化合物番号62)の調製
合成実施例1-1-7で調製した3-(2H-1,2,3-トリアゾール-2-イル)-N-(5-トリフルオロメチル)ピリジン-2-イル)イソニコチンイミダミド(0.16g、0.49mmol)をジクロロメタン(10mL)に溶解させ、クロロギ酸4-クロロフェニル(150μL、1.09mmol)、続いてトリエチルアミン(300μL、2.16mL)を加え、室温で12時間撹拌した。その後、エバポレーターでジクロロメタンを留去し、酢酸エチル(15mL)を加え、加熱還流下、2時間撹拌した。エバポレーターで酢酸エチルを減圧留去した後、得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.13g、74.0%)を得た。
1H NMR(CDCl3) δ9.39(1H, s), 9.19(1H, s), 8.85(1H, d, J=4.8Hz), 8.12(1H, dd, J=9.3, 2.4Hz), 7.92(1H, d, J=5.1Hz), 7.78(2H, s), 7.53(1H, d, J=9.0Hz)Synthesis Example 1-3-2: 2-(3-(2H-1,2,3-triazol-2-yl)pyridin-4-yl)-7-(trifluoromethyl)-4H-pyrido[1, 2-a] Preparation of [1,3,5]triazin-4-one (Compound No. 62) 3-(2H-1,2,3-triazol-2-yl prepared in Synthesis Example 1-1-7) )-N-(5-trifluoromethyl)pyridin-2-yl)isonicotinimidamide (0.16 g, 0.49 mmol) was dissolved in dichloromethane (10 mL), and 4-chlorophenyl chloroformate (150 μL, 1.09 mmol) was dissolved in dichloromethane (10 mL). ), followed by triethylamine (300 μL, 2.16 mL) and stirred at room temperature for 12 hours. Thereafter, dichloromethane was distilled off using an evaporator, ethyl acetate (15 mL) was added, and the mixture was stirred under heating under reflux for 2 hours. After ethyl acetate was distilled off under reduced pressure using an evaporator, the resulting crude product was purified by silica gel chromatography to obtain the desired product (0.13 g, 74.0%).
1H NMR(CDCl 3 ) δ9.39(1H, s), 9.19(1H, s), 8.85(1H, d, J=4.8Hz), 8.12(1H, dd, J=9.3, 2.4Hz), 7.92( 1H, d, J=5.1Hz), 7.78(2H, s), 7.53(1H, d, J=9.0Hz)
合成実施例2-1-1:3-(エチルチオ)ピコリノニトリルの調製
3-クロロピコリノニトリル(1.00g、7.22mmol)、エチルメルカプタン(0.59mL、7.98mmmol)をN,N-ジメチルホルムアミド(10mL)に溶解させ、氷浴で冷却し、水素化ナトリウム(0.35g、8.02mmol)を加えた後、室温で1.5時間撹拌した。水を加え、酢酸エチルで3回抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(1.11g、93.6%、薄黄色油状)を得た。
1H NMR(CDCl3) δ8.49(1H, dd, J=4.5, 1.2Hz), 7.75(1H, dd, J=8.4, 1.5Hz), 7.43(1H, dd, J=8.1, 4.5Hz), 3.06(2H, q, J=7.5Hz), 1.38(1H, t, J=7.5Hz)Synthesis Example 2-1-1: Preparation of 3-(ethylthio)picolinonitrile 3-chloropicolinonitrile (1.00 g, 7.22 mmol) and ethyl mercaptan (0.59 mL, 7.98 mmol) were mixed with N,N -Dissolved in dimethylformamide (10 mL), cooled in an ice bath, added sodium hydride (0.35 g, 8.02 mmol), and stirred at room temperature for 1.5 hours. Water was added and extracted three times with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (1.11 g, 93.6%, pale yellow oil).
1H NMR(CDCl 3 ) δ8.49(1H, dd, J=4.5, 1.2Hz), 7.75(1H, dd, J=8.4, 1.5Hz), 7.43(1H, dd, J=8.1, 4.5Hz), 3.06(2H, q, J=7.5Hz), 1.38(1H, t, J=7.5Hz)
合成実施例2-1-2:3-(エチルチオ)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(化合物番号36)の調製
5-(トリフルオロメチル)ピリジン-2-アミン(1.09g、6.72mmol)をN,N-ジメチルホルムアミド(16mL)に溶解させ、水素化ナトリウム(含量55%、0.33g、7.56mmol)を加え、室温で15分間撹拌した。そこに合成実施例2-1-1で調製した3-(エチルチオ)ピコリノニトリル(1.11g、6.76mol)を加え、同温度で5時間撹拌した後、水を加え、酢酸エチルで2回抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.90g、41.0%、白色固体)を得た。
1H NMR(CDCl3) δ10.04(1H, broad), 8.63(1H, s), 8.35(1H, dd, J=4.5, 1.2Hz), 7.91(1H, broad), 7.84(1H, dd, J=8.4, 2.4Hz), 7.71(1H, dd, J=8.4, 1.2Hz), 7.43(1H, d, J=8.7Hz), 7.32(1H, dd, J=8.1, 4.5Hz), 2.92(2H, q, J=7.5Hz), 1.41(3H, t, J=7.5Hz)Synthesis Example 2-1-2: Preparation of 3-(ethylthio)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (Compound No. 36) 5-(trifluoromethyl)pyridine- Dissolve 2-amine (1.09 g, 6.72 mmol) in N,N-dimethylformamide (16 mL), add sodium hydride (content 55%, 0.33 g, 7.56 mmol), and stir at room temperature for 15 minutes. did. 3-(ethylthio)picolinonitrile (1.11 g, 6.76 mol) prepared in Synthesis Example 2-1-1 was added thereto, and after stirring at the same temperature for 5 hours, water was added, and ethyl acetate was added to After extraction, the organic layer obtained was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.90 g, 41.0%, white solid).
1H NMR(CDCl 3 ) δ10.04(1H, broad), 8.63(1H, s), 8.35(1H, dd, J=4.5, 1.2Hz), 7.91(1H, broad), 7.84(1H, dd, J =8.4, 2.4Hz), 7.71(1H, dd, J=8.4, 1.2Hz), 7.43(1H, d, J=8.7Hz), 7.32(1H, dd, J=8.1, 4.5Hz), 2.92(2H , q, J=7.5Hz), 1.41(3H, t, J=7.5Hz)
合成実施例2-1-3:3-(エチルチオ)-5-(4-(トリフルオロメチル)フェニル)ピコリノニトリルの調製
WO2017016922、p57に記載の方法で調製した5-ブロモ-3-(エチルチオ)ピコリノニトリル(0.48g、1.97mmol)を1,4-ジオキサン(25mL)に溶解させ、系内をポンプで脱気した後、窒素で置換しジクロロビス(トリフェニルホスフィン)パラジウム(II)(0.14g、0.20mmol)を加え、窒素雰囲気下、60℃で10分間加熱撹拌した。その後、(4-(トリフルオロメチル)フェニル)ボロン酸(0.45g、2.37mmol)、2M炭酸ナトリウム水溶液(5mL)を加え、再度脱気、窒素で置換し、還流下、2時間撹拌した。放冷後、酢酸エチル、水を加え、ろ過助剤を用いたろ過により、不要物を取り除いた。ろ液にさらに水をを加え、酢酸エチルで2度抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.60g、98.6%)を得た。
1H NMR(CDCl3) δ8.69(1H, d, J=1.8Hz), 7.87(1H, d, J=2.1Hz), 7.80(2H, d, J=8.4Hz), 7.70(2H, d, J=8.4Hz), 3.13(1H, q, J=7.5Hz), 1.43(3H, t, J=7.5Hz)Synthesis Example 2-1-3: Preparation of 3-(ethylthio)-5-(4-(trifluoromethyl)phenyl)picolinonitrile 5-bromo-3-(ethylthio) prepared by the method described in WO2017016922, p. ) Picolinonitrile (0.48 g, 1.97 mmol) was dissolved in 1,4-dioxane (25 mL), the system was degassed with a pump, and then replaced with nitrogen to dichlorobis(triphenylphosphine)palladium(II). (0.14 g, 0.20 mmol) was added, and the mixture was heated and stirred at 60° C. for 10 minutes under a nitrogen atmosphere. Then, (4-(trifluoromethyl)phenyl)boronic acid (0.45 g, 2.37 mmol) and 2M aqueous sodium carbonate solution (5 mL) were added, degassed again, replaced with nitrogen, and stirred under reflux for 2 hours. . After cooling, ethyl acetate and water were added, and unnecessary substances were removed by filtration using a filter aid. Water was further added to the filtrate, extracted twice with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.60 g, 98.6%).
1H NMR(CDCl 3 ) δ8.69(1H, d, J=1.8Hz), 7.87(1H, d, J=2.1Hz), 7.80(2H, d, J=8.4Hz), 7.70(2H, d, J=8.4Hz), 3.13(1H, q, J=7.5Hz), 1.43(3H, t, J=7.5Hz)
合成実施例2-1-4:3-(エチルチオ)-5-(4-(トリフルオロメチル)フェニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミドの調製(化合物番号138)
5-(トリフルオロメチル)ピリジン-2-アミン(106mg、0.65mmol)をN,N-ジメチルホルムアミド(4mL)に溶解させ、水素化ナトリウム(含量55%、31mg、0.71mmol)を加え、室温で15分間撹拌した。そこに合成実施例2-1-3で調製した3-(エチルチオ)-5-(4-(トリフルオロメチル)ピコリノニトリル(200mg、6.49mol)を加え、室温で16時間撹拌した後、水を加え、酢酸エチルで2回抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製した後、酢酸エチルとヘキサンの混合液に生成物を懸濁させ、ろ過、目的物を得た。
1H NMR(CDCl3) δ10.07(1H, broad), 8.65(1H, s), 8.55(1H, d, J=1.8Hz), 7.86(1H, dd, J=8.4Hz, 2.4Hz), 7.84(1H, d, J=2.1Hz), 7.78(2H, d, J=8.1Hz), 7.72(2H, d, J=8.1Hz), 7.46(1H, d, J=8.4Hz), 2.97(2H, q, J=7.5Hz), 1.46(3H, t, J=7.5Hz)Synthesis Example 2-1-4: Preparation of 3-(ethylthio)-5-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide ( Compound number 138)
5-(Trifluoromethyl)pyridin-2-amine (106 mg, 0.65 mmol) was dissolved in N,N-dimethylformamide (4 mL), sodium hydride (content 55%, 31 mg, 0.71 mmol) was added, Stirred at room temperature for 15 minutes. 3-(ethylthio)-5-(4-(trifluoromethyl)picolinonitrile (200 mg, 6.49 mol) prepared in Synthesis Example 2-1-3 was added thereto, and after stirring at room temperature for 16 hours, Water was added, extracted twice with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator.The resulting crude product was purified by silica gel chromatography, and acetic acid The product was suspended in a mixture of ethyl and hexane and filtered to obtain the desired product.
1H NMR(CDCl 3 ) δ10.07(1H, broad), 8.65(1H, s), 8.55(1H, d, J=1.8Hz), 7.86(1H, dd, J=8.4Hz, 2.4Hz), 7.84 (1H, d, J=2.1Hz), 7.78(2H, d, J=8.1Hz), 7.72(2H, d, J=8.1Hz), 7.46(1H, d, J=8.4Hz), 2.97(2H , q, J=7.5Hz), 1.46(3H, t, J=7.5Hz)
合成実施例2-1-5:3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミドの調製(化合物番号139)
合成実施例2-1-4で調製した3-(エチルチオ)-5-(4-(トリフルオロメチル)フェニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(0.27g、0.57mmol)をジクロロメタン(5.5mL)に溶解させ、3-クロロ過安息香酸(65%、0.31g、1.15mmol)を加え、室温で18時間撹拌した。炭酸水素ナトリウム水溶液を加え、酢酸エチルで抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.26g、91.5%)を得た。
1H NMR(CDCl3) δ10.17(1H, broad), 9.05(1H, d, J=2.1Hz), 8.71(1H, d, J=1.5Hz), 8.69(1H, s), 7.95-7.75(6H, m), 7.20(1H, d, J=2.4Hz), 4.05(2H, q, J=7.5Hz), 1.42(3H, t, J=7.5Hz)Synthesis Example 2-1-5: Preparation of 3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (Compound number 139)
3-(ethylthio)-5-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (prepared in Synthesis Example 2-1-4) 0.27 g, 0.57 mmol) was dissolved in dichloromethane (5.5 mL), 3-chloroperbenzoic acid (65%, 0.31 g, 1.15 mmol) was added, and the mixture was stirred at room temperature for 18 hours. An aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.26 g, 91.5%).
1H NMR(CDCl 3 ) δ10.17(1H, broad), 9.05(1H, d, J=2.1Hz), 8.71(1H, d, J=1.5Hz), 8.69(1H, s), 7.95-7.75( 6H, m), 7.20(1H, d, J=2.4Hz), 4.05(2H, q, J=7.5Hz), 1.42(3H, t, J=7.5Hz)
合成実施例2-1-6:3-(エチルチオ)-5-(2H-1,2,3-トリアゾール-2-イル)ピコリノニトリルの調製
WO2017016922、p57に記載の方法で調製した5-ブロモ-3-(エチルチオ)ピコリノニトリル(1.00g、4.11mmol)をN,N-ジメチルホルムアミド(10mL)に溶解させ、1H-1,2,3-トリアゾール(0.31g、4.49mmol)、炭酸カリウム(0.85g、6.15mmol)を加え、80℃で5時間撹拌した。放冷後、水を加え、酢酸エチルで2度抽出し、飽和食塩水で洗浄後、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.49g、51.5%)を得た。
1H NMR(CDCl3) δ9.21(1H, d, J=2.4Hz), 8.36(1H, d, J=2.1Hz), 7.93(2H, s), 3.17(2H, q, J=7.5Hz), 1.47(3H, t, J=7.5Hz)Synthesis Example 2-1-6: Preparation of 3-(ethylthio)-5-(2H-1,2,3-triazol-2-yl)picolinonitrile 5-bromo prepared by the method described in WO2017016922, p57 -3-(ethylthio)picolinonitrile (1.00 g, 4.11 mmol) was dissolved in N,N-dimethylformamide (10 mL), and 1H-1,2,3-triazole (0.31 g, 4.49 mmol) was dissolved. , potassium carbonate (0.85 g, 6.15 mmol) was added, and the mixture was stirred at 80° C. for 5 hours. After cooling, water was added and extracted twice with ethyl acetate. After washing with saturated brine, the resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.49 g, 51.5%).
1H NMR(CDCl 3 ) δ9.21(1H, d, J=2.4Hz), 8.36(1H, d, J=2.1Hz), 7.93(2H, s), 3.17(2H, q, J=7.5Hz) , 1.47(3H, t, J=7.5Hz)
合成実施例2-1-7:3-(エチルチオ)-5-(2H-1,2,3-トリアゾール-2-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミドの調製(化合物番号102)
5-(トリフルオロメチル)ピリジン-2-アミン(130mg、0.80mmol)をN,N-ジメチルホルムアミド(4mL)に溶解させ、水素化ナトリウム(含量55%、35mg、0.89mmol)を加え、室温で15分間撹拌した。そこに合成実施例2-1-6で調製した3-(エチルチオ)-5-(2H-1,2,3-トリアゾール-2-イル)ピコリノニトリル(186mg、0.80mol)を加え、室温で4時間撹拌した。反応物に水を加え、酢酸エチルで抽出、飽和食塩水で洗浄し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製した後、酢酸エチルとヘキサンの混合液に生成物を懸濁させ、ろ過、目的物(92mg、29.1%)を得た。
1H NMR(CDCl3) δ10.06(1H, broad), 9.08(1H, d, J=2.1Hz), 8.65(1H, s), 8.40(1H, d, J=2.1Hz), 7.90(2H, s), 7.86(1H, dd, J=8.7, 2.7Hz), 7.45(1H, d, J=8.4Hz), 3.02(2H, q, J=7.5Hz), 1.48(3H, t, J=7.5Hz)Synthesis Example 2-1-7: 3-(ethylthio)-5-(2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl)picoline Preparation of imidamide (compound no. 102)
5-(Trifluoromethyl)pyridin-2-amine (130 mg, 0.80 mmol) was dissolved in N,N-dimethylformamide (4 mL), sodium hydride (content 55%, 35 mg, 0.89 mmol) was added, Stirred at room temperature for 15 minutes. 3-(ethylthio)-5-(2H-1,2,3-triazol-2-yl)picolinonitrile (186 mg, 0.80 mol) prepared in Synthesis Example 2-1-6 was added thereto, and The mixture was stirred for 4 hours. Water was added to the reaction mixture, extracted with ethyl acetate, washed with saturated brine, and the resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. After the obtained crude product was purified by silica gel chromatography, the product was suspended in a mixture of ethyl acetate and hexane, and filtered to obtain the desired product (92 mg, 29.1%).
1H NMR(CDCl 3 ) δ10.06(1H, broad), 9.08(1H, d, J=2.1Hz), 8.65(1H, s), 8.40(1H, d, J=2.1Hz), 7.90(2H, s), 7.86(1H, dd, J=8.7, 2.7Hz), 7.45(1H, d, J=8.4Hz), 3.02(2H, q, J=7.5Hz), 1.48(3H, t, J=7.5 Hz)
合成実施例2-1-8:3-(エチルスルホニル)-5-(2H-1,2,3-トリアゾール-2-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミドの調製(化合物番号103)
合成実施例2-1-7で調製した3-(エチルチオ)-5-(2H-1,2,3-トリアゾール-2-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(62mg、0.16mmol)をジクロロメタン(2.5mL)に溶解させ、3-クロロ過安息香酸(65%、86g、0.32mmol)を加え、室温で2時間撹拌した。炭酸水素ナトリウム水溶液を加え、酢酸エチルで抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(45mg、67.1%)を得た。
1H NMR(CDCl3) δ9.55(1H, d, J=2.4Hz), 9.18(1H, d, J=1.8Hz), 8.68(1H, s), 8.05-7.92(3H, m), 7.88(1H, dd, J=8.7Hz, 2.1Hz), 7.20(1H, d, J=8.7Hz), 4.07(2H, q, J=7.5Hz), 1.44(3H, t, J=7.5Hz)Synthesis Example 2-1-8: 3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl) Preparation of picolinimidamide (compound no. 103)
3-(ethylthio)-5-(2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridin-2-yl prepared in Synthesis Example 2-1-7 ) Picolinimidamide (62 mg, 0.16 mmol) was dissolved in dichloromethane (2.5 mL), 3-chloroperbenzoic acid (65%, 86 g, 0.32 mmol) was added, and the mixture was stirred at room temperature for 2 hours. An aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (45 mg, 67.1%).
1H NMR(CDCl 3 ) δ9.55(1H, d, J=2.4Hz), 9.18(1H, d, J=1.8Hz), 8.68(1H, s), 8.05-7.92(3H, m), 7.88( 1H, dd, J=8.7Hz, 2.1Hz), 7.20(1H, d, J=8.7Hz), 4.07(2H, q, J=7.5Hz), 1.44(3H, t, J=7.5Hz)
合成実施例2-1-9:3-クロロ-5-(ジメチルアミノ)ピコリノニトリルの調製
3,5-ジクロロピコリノニトリル(1.00g、5.78mmol)をN,N-ジメチルホルムアミド(10mL)に溶解させ、50%ジメチルアミン水溶液(1.21mL、11.56mmol)加え、室温で20時間撹拌した。反応物に水を加え、酢酸エチルで2回抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去した。得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.70g、66.7%)を得た。
1H NMR(CDCl3) δ8.01(1H, d, J=2.7Hz), 6.88(1H, d, J=2.7Hz), 3.10(3H, s)Synthesis Example 2-1-9: Preparation of 3-chloro-5-(dimethylamino)picolinonitrile 3,5-dichloropicolinonitrile (1.00 g, 5.78 mmol) was dissolved in N,N-dimethylformamide (10 mL). ), 50% dimethylamine aqueous solution (1.21 mL, 11.56 mmol) was added, and the mixture was stirred at room temperature for 20 hours. Water was added to the reaction mixture, extracted twice with ethyl acetate, and the resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The obtained crude product was purified by silica gel chromatography to obtain the desired product (0.70 g, 66.7%).
1H NMR(CDCl 3 ) δ8.01(1H, d, J=2.7Hz), 6.88(1H, d, J=2.7Hz), 3.10(3H, s)
合成実施例2-1-10:5-(ジメチルアミノ)-3-(エチルチオ)ピコリノニトリルの調製
合成実施例2-1-9で調製した3-クロロ-5-(ジメチルアミノ)ピコリノニトリル(0.70g、3.85mmol)をN,N-ジメチルホルムアミド(14mL)に溶解させ、エチルメルカプタン(0.92mL、3.92mmol)加え、氷冷下、水素化ナトリウム(55%、0.19g、4.29mmol)を加え、撹拌した。室温に戻し、同温度で3時間撹拌した後、反応物に水を加え、酢酸エチルで2回抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去し、粗目的物(0.81g)を得た。
1H NMR(CDCl3) δ7.94(1H, d, J=2.7Hz), 6.81(1H, d, J=3.0Hz), 3.09(6H, s), 3.03(2H, q, J=7.5Hz), 1.35(3H, t, J=7.5Hz)Synthesis Example 2-1-10: Preparation of 5-(dimethylamino)-3-(ethylthio)picolinonitrile 3-chloro-5-(dimethylamino)picolinonitrile prepared in Synthesis Example 2-1-9 (0.70 g, 3.85 mmol) was dissolved in N,N-dimethylformamide (14 mL), ethyl mercaptan (0.92 mL, 3.92 mmol) was added, and under ice cooling, sodium hydride (55%, 0.19 g , 4.29 mmol) and stirred. After returning to room temperature and stirring at the same temperature for 3 hours, water was added to the reaction mixture, extracted twice with ethyl acetate, the resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator. The crude target product (0.81 g) was obtained.
1H NMR(CDCl 3 ) δ7.94(1H, d, J=2.7Hz), 6.81(1H, d, J=3.0Hz), 3.09(6H, s), 3.03(2H, q, J=7.5Hz) , 1.35(3H, t, J=7.5Hz)
合成実施例2-1-11:5-(ジメチルアミノ)-3-(エチルチオ)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミドの調製(化合物番号124)
合成実施例2-1-10で調製した5-(ジメチルアミノ)-3-(エチルチオ)ピコリノニトリル(0.20g、0.96mmol)をトルエン(10mL)に溶解させ、氷冷下、トリメチルアルミニウム(1.8Mトルエン溶液、1.0mL、3.92mmol)加え、室温で2時間撹拌した。その後、5-(トリフルオロメチル)ピリジン-2-アミン(0.16g、0.96mmol)を加え、70℃で6時間撹拌した。反応物に水を加え、酢酸エチルで2回抽出し、得られた有機層を無水硫酸マグネシウムで乾燥、濾過後、エバポレーターで減圧留去し、目的物(73mg、21%)を得た。
1H NMR(CDCl3) δ9.98(1H, broad), 8.58(1H, s), 7.89(1H, d, J=1.8Hz), 7.80(1H, dd, J=8.4Hz, 2.4Hz), 7.42(1H, broad), 6.82(1H, d, J=2.4Hz), 3.09(6H, s), 2.89(2H, q, J=7.5Hz), 1.44(3H, t, J=7.5Hz)Synthesis Example 2-1-11: Preparation of 5-(dimethylamino)-3-(ethylthio)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (Compound No. 124)
5-(dimethylamino)-3-(ethylthio)picolinonitrile (0.20 g, 0.96 mmol) prepared in Synthesis Example 2-1-10 was dissolved in toluene (10 mL), and trimethylaluminum was added under ice cooling. (1.8M toluene solution, 1.0 mL, 3.92 mmol) was added and stirred at room temperature for 2 hours. Then, 5-(trifluoromethyl)pyridin-2-amine (0.16 g, 0.96 mmol) was added and stirred at 70° C. for 6 hours. Water was added to the reaction mixture and extracted twice with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered, and then evaporated under reduced pressure using an evaporator to obtain the desired product (73 mg, 21%).
1H NMR(CDCl 3 ) δ9.98(1H, broad), 8.58(1H, s), 7.89(1H, d, J=1.8Hz), 7.80(1H, dd, J=8.4Hz, 2.4Hz), 7.42 (1H, broad), 6.82(1H, d, J=2.4Hz), 3.09(6H, s), 2.89(2H, q, J=7.5Hz), 1.44(3H, t, J=7.5Hz)
合成実施例2-2-1:2-(3-(エチルチオ)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号53)の調製
合成実施例2-1-2で調製した3-(エチルチオ)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(0.38g、1.16mmol)をジクロロメタン(12ml)に溶解させ、ヨードベンゼンジアセテート(0.39g、1.22mmol)を加え、室温で10時間撹拌した。エバポレーターで減圧留去後、得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(0.19g、49.1%)を得た。
1H NMR(CDCl3) δ9.06(1H, s), 8.60(1H, dd, J=4.5, 1.2Hz), 7.98(1H, d, J=9.3Hz), 7.76(1H., d, J=8.1, 1.5Hz), 7.72(1H, dd, J=9.3, 1.8Hz), 7.37(1H, dd, J=8.1, 4.5Hz), 3.02(2H, q, J=7.5Hz), 1.40(3H, t, J=7.5Hz)Synthesis Example 2-2-1: 2-(3-(ethylthio)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (compound Preparation of No. 53) 3-(ethylthio)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide (0.38 g, 1.16 mmol) prepared in Synthesis Example 2-1-2 was dissolved in dichloromethane (12 ml), iodobenzenediacetate (0.39 g, 1.22 mmol) was added, and the mixture was stirred at room temperature for 10 hours. After distillation under reduced pressure using an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the desired product (0.19 g, 49.1%).
1H NMR(CDCl 3 ) δ9.06(1H, s), 8.60(1H, dd, J=4.5, 1.2Hz), 7.98(1H, d, J=9.3Hz), 7.76(1H., d, J= 8.1, 1.5Hz), 7.72(1H, dd, J=9.3, 1.8Hz), 7.37(1H, dd, J=8.1, 4.5Hz), 3.02(2H, q, J=7.5Hz), 1.40(3H, t, J=7.5Hz)
合成実施例2-2-2:2-(3-(エチルスルフィニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号54)及び2-(3-(エチルスルホニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(化合物番号55)の調製
合成実施例2-2-1で調製した2-(3-(エチルチオ)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(0.13g、0.40mmol)をジクロロメタン(10mL)に溶解させ、3-クロロ過安息香酸(65%、0.16g、0.60mmol)を加え、室温で20分間撹拌した。エバポレーターでジクロロメタンを減圧留去後、得られた粗生成物をシリカゲルクロマトグラフィーで精製し、2-(3-(エチルスルフィニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(6.4mg、4.7%)及び2-(3-(エチルスルホニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジン(95mg、66.5%)を得た。
化合物54
1H NMR(CDCl3) δ9.04(1H, s), 8.93(1H, s), 8.63(1H, dd, J=8.1, 1.5Hz), 7.98(1H, d, J=9.3Hz), 7.79(1H, dd, J=9.3, 1.8Hz), 7.70(1H, dd, J=8.1, 4.8Hz), 3.46(1H, m), 3.00(1H, m), 1.39(3H, t, J=7.5Hz)
化合物55
1H NMR(CDCl3) δ9.07-8.98(2H, m), 8.55(1H, dd, J=8.1, 1.8Hz), 7.94(1H, d, J=9.6Hz), 7.76(1H, dd, J=9.6, 1.8Hz), 7.68(1H, dd, J=7.8, 4.5Hz), 3.96(2H, q, J=7.5Hz), 1.41(3H, t, J=7.5Hz)Synthesis Example 2-2-2: 2-(3-(ethylsulfinyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine ( Compound No. 54) and 2-(3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyridine (Compound No. 55) Preparation of 2-(3-(ethylthio)pyridin-2-yl)-6-(trifluoromethyl)-[1,2,4]triazolo[1,5-a] prepared in Synthesis Example 2-2-1 ] Pyridine (0.13 g, 0.40 mmol) was dissolved in dichloromethane (10 mL), 3-chloroperbenzoic acid (65%, 0.16 g, 0.60 mmol) was added, and the mixture was stirred at room temperature for 20 minutes. After dichloromethane was distilled off under reduced pressure using an evaporator, the obtained crude product was purified by silica gel chromatography and 2-(3-(ethylsulfinyl)pyridin-2-yl)-6-(trifluoromethyl)-[1, 2,4]triazolo[1,5-a]pyridine (6.4 mg, 4.7%) and 2-(3-(ethylsulfonyl)pyridin-2-yl)-6-(trifluoromethyl)-[1 ,2,4]triazolo[1,5-a]pyridine (95 mg, 66.5%) was obtained.
Compound 54
1H NMR(CDCl 3 ) δ9.04(1H, s), 8.93(1H, s), 8.63(1H, dd, J=8.1, 1.5Hz), 7.98(1H, d, J=9.3Hz), 7.79( 1H, dd, J=9.3, 1.8Hz), 7.70(1H, dd, J=8.1, 4.8Hz), 3.46(1H, m), 3.00(1H, m), 1.39(3H, t, J=7.5Hz )
Compound 55
1H NMR(CDCl 3 ) δ9.07-8.98(2H, m), 8.55(1H, dd, J=8.1, 1.8Hz), 7.94(1H, d, J=9.6Hz), 7.76(1H, dd, J =9.6, 1.8Hz), 7.68(1H, dd, J=7.8, 4.5Hz), 3.96(2H, q, J=7.5Hz), 1.41(3H, t, J=7.5Hz)
合成実施例2-2-3:2-(3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジンの調製(化合物番号176)
合成実施例2-1-5で調製した3-(エチルスルホニル)-5-(4-(トリフルオロメチル)フェニル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(51mg、0.10mmol)をジクロロメタン(2.5mL)に溶解させ、ヨードベンゼンジアセテート(98mg、0.30mmol)を加え、室温で18時間撹拌した。エバポレーターで減圧留去後、得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(37mg、72.8%)を得た。
1H NMR(CDCl3) δ9.23(1H, d, J=2.1Hz), 9.02(1H, s), 8.74(1H, d, J=2.1Hz), 7.96(1H, d, J=9.3Hz), 7.89-7.79(4H, m), 7.78(1H, dd, J=9.3Hz, 1.5Hz), 4.05(2H, q, J=7.5Hz), 1.46(3H, t, J=7.5Hz)Synthesis Example 2-2-3: 2-(3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)pyridin-2-yl)-6-(trifluoromethyl)-[1,2 , 4] Preparation of triazolo[1,5-a]pyridine (Compound No. 176)
3-(ethylsulfonyl)-5-(4-(trifluoromethyl)phenyl)-N-(5-(trifluoromethyl)pyridin-2-yl)picolinimidamide prepared in Synthesis Example 2-1-5 (51 mg, 0.10 mmol) was dissolved in dichloromethane (2.5 mL), iodobenzenediacetate (98 mg, 0.30 mmol) was added, and the mixture was stirred at room temperature for 18 hours. After distillation under reduced pressure using an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the desired product (37 mg, 72.8%).
1H NMR(CDCl 3 ) δ9.23(1H, d, J=2.1Hz), 9.02(1H, s), 8.74(1H, d, J=2.1Hz), 7.96(1H, d, J=9.3Hz) , 7.89-7.79(4H, m), 7.78(1H, dd, J=9.3Hz, 1.5Hz), 4.05(2H, q, J=7.5Hz), 1.46(3H, t, J=7.5Hz)
合成実施例2-2-4:2-(3-(エチルスルホニル)-5-(2H-1,2,3-トリアゾール-2-イル)ピリジン-2-イル)-6-(トリフルオロメチル)-[1,2,4]トリアゾロ[1,5-a]ピリジンの調製(化合物番号181)
合成実施例2-1-8で調製した3-(エチルスルホニル)-5-(2H-1,2,3-トリアゾール-2-イル)-N-(5-(トリフルオロメチル)ピリジン-2-イル)ピコリンイミダミド(0.10g、0.24mmol)をジクロロメタン(3mL)に溶解させ、ヨードベンゼンジアセテート(0.23g、0.71mmol)を加え、室温で16時間撹拌した。エバポレーターで減圧留去後、得られた粗生成物をシリカゲルクロマトグラフィーで精製し、目的物(72mg、72.4%)を得た。
1H NMR(CDCl3) δ9.74(1H, d, J=2.1Hz), 9.20(1H, d, J=2.1Hz), 9.02(1H,s), 8.01-7.92(3H, m), 7.78(1H, dd, J=9.3Hz, 1.5Hz), 4.06(2H, q, J=7.5Hz), 1.47(3H, t, J=7.5Hz)Synthesis Example 2-2-4: 2-(3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)pyridin-2-yl)-6-(trifluoromethyl) - Preparation of [1,2,4]triazolo[1,5-a]pyridine (Compound No. 181)
3-(ethylsulfonyl)-5-(2H-1,2,3-triazol-2-yl)-N-(5-(trifluoromethyl)pyridine-2- prepared in Synthesis Example 2-1-8) Picolinimidamide (0.10 g, 0.24 mmol) was dissolved in dichloromethane (3 mL), and iodobenzene diacetate (0.23 g, 0.71 mmol) was added, followed by stirring at room temperature for 16 hours. After distillation under reduced pressure using an evaporator, the obtained crude product was purified by silica gel chromatography to obtain the desired product (72 mg, 72.4%).
1H NMR(CDCl 3 ) δ9.74(1H, d, J=2.1Hz), 9.20(1H, d, J=2.1Hz), 9.02(1H,s), 8.01-7.92(3H, m), 7.78( 1H, dd, J=9.3Hz, 1.5Hz), 4.06(2H, q, J=7.5Hz), 1.47(3H, t, J=7.5Hz)
前記と同様の方法より合成した表8に示す式(1-3)の本発明化合物、表9に示す式(1-4)の本発化合物、表10に示す式(2-2)の本発化合物、表11に示す式(2-3)の本発化合物、表12に示す式(3-2)の本発化合物、表13に示す式(3-3)の本発化合物の1H-NMRデータ及び融点を表14に示す。なお、NMRデータにはアミジンのプロトンが検出されてないものもある。
<製剤例>
また、本発明の化合物を有効成分として含有する農薬製剤例を以下に挙げる。
製剤例1〔水和剤〕
化合物 30重量%
クレー 30重量%
ケイソウ土 35重量%
サンエキスP252 4重量%
(リグニンスルホン酸カルシウム:日本製紙(株)の商品名)
ソルポール8070 1重量%
(ラウリル硫酸ナトリウム:東邦化学工業(株)の商品名)
前記成分を均一に混合し、粉砕して水和剤を得た。<Formulation example>
Further, examples of agricultural chemical formulations containing the compound of the present invention as an active ingredient are listed below.
Formulation example 1 [hydrating powder]
Compound 30% by weight
Clay 30% by weight
Diatomaceous earth 35% by weight
Sunextract P252 4% by weight
(Calcium lignin sulfonate: Nippon Paper Industries Co., Ltd. product name)
Solpol 8070 1% by weight
(Sodium lauryl sulfate: trade name of Toho Chemical Industry Co., Ltd.)
The components were mixed uniformly and ground to obtain a wettable powder.
製剤例2〔粉剤〕
化合物 2重量%
クレー 90重量%
タルク 7重量%
ステアリン酸カルシウム 1重量%
前記成分を均一に混合して粉剤を得た。Formulation example 2 [powder]
Compound 2% by weight
Clay 90% by weight
Talc 7% by weight
Calcium stearate 1% by weight
The above ingredients were mixed uniformly to obtain a powder.
製剤例3〔乳剤〕
化合物 20重量%
N,N-ジメチルホルムアミド 20重量%
T-SOL 150 50重量%
(芳香族系溶剤:JXTGエネルギー株式会社の製品名)
ニューカルゲンCL-H 10重量%
(POEアルキルフェニルエーテル:竹本油脂(株)の製品名)
前記成分を均一に混合し、溶解して乳剤を得た。Formulation example 3 [emulsion]
Compound 20% by weight
N,N-dimethylformamide 20% by weight
T-SOL 150 50% by weight
(Aromatic solvent: JXTG Energy Corporation product name)
New Calgen CL-H 10% by weight
(POE alkyl phenyl ether: product name of Takemoto Yushi Co., Ltd.)
The components were uniformly mixed and dissolved to obtain an emulsion.
製剤例4〔乳剤2〕
化合物 5重量%
キシレン 42.5重量%
DMSO 42.5重量%
ニューカルゲン2003 10重量%
(POEアリルフェニルエーテルホルムアルデヒド縮合物とアルキルベンゼンスルホン酸金属塩の混合物:竹本油脂(株)の製品名)
前記成分を均一に混合し、溶解して乳剤を得た。
製剤例5〔粒剤〕
化合物 5重量%
ベントナイト 40重量%
タルク 10重量%
クレー 43重量%
サンエキスP252 2重量%
(リグニンスルホン酸カルシウム:日本製紙(株)の商品名)
前記成分を均一に粉砕・混合し、水を加えてよく練合した後、造粒乾燥して粒剤を得た。Formulation example 4 [emulsion 2]
Compound 5% by weight
Xylene 42.5% by weight
DMSO 42.5% by weight
New Calgen 2003 10% by weight
(Mixture of POE allyl phenyl ether formaldehyde condensate and alkylbenzene sulfonic acid metal salt: product name of Takemoto Yushi Co., Ltd.)
The components were uniformly mixed and dissolved to obtain an emulsion.
Formulation example 5 [granules]
Compound 5% by weight
Bentonite 40% by weight
Talc 10% by weight
Clay 43% by weight
Sunextract P252 2% by weight
(Calcium lignin sulfonate: Nippon Paper Industries Co., Ltd. product name)
The above components were uniformly ground and mixed, water was added and the mixture was thoroughly kneaded, followed by granulation and drying to obtain granules.
製剤例6〔フロアブル剤〕
化合物 25重量%
ソルポール7556 5重量%
(POEスチリルフェニルエーテル硫酸塩:東邦化学工業(株)の製品名)
プロピレングリコール 6重量%
ベントナイト 1重量%
キサンタンガム1%水溶液 3重量%
水 60重量%
キサンタンガム1%水溶液および適当量の水を除いた前記処方の全量を予備混合した後、湿式粉砕機にて粉砕した。その後、得られた粉砕物にキサンタンガム1% 水溶液および残りの水を加え、100重量%のフロアブル剤を得た。Formulation example 6 [flowable agent]
Compound 25% by weight
Solpol 7556 5% by weight
(POE styryl phenyl ether sulfate: product name of Toho Chemical Industry Co., Ltd.)
Propylene glycol 6% by weight
Bentonite 1% by weight
Xanthan gum 1% aqueous solution 3% by weight
Water 60% by weight
The entire amount of the above formulation except for the 1% xanthan gum aqueous solution and an appropriate amount of water was premixed and then pulverized using a wet pulverizer. Thereafter, a 1% xanthan gum aqueous solution and the remaining water were added to the obtained pulverized product to obtain a 100% by weight flowable agent.
製剤例7〔粒剤〕
化合物 5重量%
ベントナイト 40重量%
タルク 10重量%
クレー 43重量%
サンエキスP252 2重量%
(リグニンスルホン酸カルシウム:日本製紙(株)の商品名)
前記成分を均一に粉砕・混合し、水を加えてよく練合した後、造粒乾燥して粒剤を得た。Formulation example 7 [granules]
Compound 5% by weight
Bentonite 40% by weight
Talc 10% by weight
Clay 43% by weight
Sunextract P252 2% by weight
(Calcium lignin sulfonate: Nippon Paper Industries Co., Ltd. product name)
The above components were uniformly ground and mixed, water was added and the mixture was thoroughly kneaded, followed by granulation and drying to obtain granules.
<生物試験例>
以下の試験が、本発明の化合物の特定の有害生物に対する防除効力を実証する。「防除効力」は、摂食を著しく低減させる有害無脊椎生物の発育の阻害(死亡率を含む)を表す。化合物によって達成される有害生物の防除保護は、しかしながら、これらの種に限定されない。化合物番号は表8~13の化合物を指す。<Biological test example>
The following tests demonstrate the control efficacy of the compounds of the invention against certain pests. "Control efficacy" refers to inhibition of growth (including mortality) of harmful invertebrates that significantly reduces feeding. The pest control protection achieved by the compounds is, however, not limited to these species. Compound numbers refer to compounds in Tables 8-13.
生物試験例1:ワタアブラムシ(Aphis gossypii)防除試験(葉片散布処理)
キュウリ葉を直径3.5cmに切り、水で湿らせた脱脂綿の上に置いた。ここにワタアブラムシ成虫2頭を放虫し、24時間産仔させた後、成虫を除去した。このキュウリ葉に200ppmになるように水で希釈した供試化合物の希釈液2mLを、散布塔を用いて散布した。風乾後、脱脂綿とともにプラスチックカップに入れ、蓋をして25 ℃の定温室にて飼育した。処理5日後に生死を観察し、死虫率を算出した。
その結果、本発明化合物1、2、3、4、5、7、8、9、10、11、12、14、17、18、19、20、26、27、28、29、30、31、42、43、45、46、48、49、50、51、53、54、55、59、61、62、66、80、85、86、87、91、103、105、106、108、110、111、112、114、120、123、125、127、135、148、150、152、156、160、170、173、174、175、177,180、181、199、201、204、207、209、215、220は80%以上の死虫率を示した。Biological test example 1: Cotton aphid (Aphis gossypii) control test (leaf spray treatment)
Cucumber leaves were cut into 3.5 cm diameter pieces and placed on absorbent cotton moistened with water. Two adult cotton aphids were released here, and after spawning for 24 hours, the adults were removed. 2 mL of a diluted solution of the test compound diluted with water to 200 ppm was sprayed onto the cucumber leaves using a spray tower. After air-drying, the mice were placed in a plastic cup with absorbent cotton, covered with a lid, and raised in a constant temperature room at 25°C. Five days after the treatment, the insects were observed to be alive or dead, and the mortality rate was calculated.
As a result, the compounds of the present invention 1, 2, 3, 4, 5, 7, 8, 9, 10, 11, 12, 14, 17, 18, 19, 20, 26, 27, 28, 29, 30, 31, 42, 43, 45, 46, 48, 49, 50, 51, 53, 54, 55, 59, 61, 62, 66, 80, 85, 86, 87, 91, 103, 105, 106, 108, 110, 111, 112, 114, 120, 123, 125, 127, 135, 148, 150, 152, 156, 160, 170, 173, 174, 175, 177, 180, 181, 199, 201, 204, 207, 209, 215 and 220 showed a mortality rate of 80% or more.
生物試験例2:ワタアブラムシ(Aphis gossypii)防除試験(根部浸漬処理)
キュウリ苗1本(子葉期)を、3.1ppmに水で希釈した薬液10mLを入れたバイアル瓶(内径2.7cmx6cm)に根部が浸るようウレタンにて固定した。浸漬1日後にワタアブラムシ1令幼虫5頭を放虫し、25 ℃の定温室にて飼育した。放虫5~7日後に虫の生死、異常を調査した。
その結果、本発明化合物2、3、7、14、20、29、45、46、48、51、53、55、62、85、91、103、105、106、108、111、120、170、173、180、199は80%以上の死虫率を示した。Biological test example 2: Cotton aphid (Aphis gossypii) control test (root immersion treatment)
One cucumber seedling (cotyledon stage) was fixed with urethane in a vial (inner diameter 2.7 cm x 6 cm) containing 10 mL of a chemical solution diluted with water to 3.1 ppm so that the root part was immersed. One day after soaking, five 1st instar cotton aphid larvae were released and raised in a constant temperature room at 25°C. Five to seven days after the insects were released, the insects were examined for life, death, and abnormalities.
As a result, the compounds of the present invention 2, 3, 7, 14, 20, 29, 45, 46, 48, 51, 53, 55, 62, 85, 91, 103, 105, 106, 108, 111, 120, 170, 173, 180, and 199 showed a mortality rate of 80% or more.
生物試験例3:タバココナジラミ(Bemisia tabaci) 防除試験(茎葉散布処理)
キュウリ葉を直径6.0cmに切り、水で湿らせた脱脂綿の上に置いた。このキュウリ葉に、200ppmになるように水で希釈した供試化合物の希釈液2mLを、散布塔を用いて散布した。風乾後、このキュウリ葉をプラスチックカップに入れ、20頭のタバココナジラミ雌成虫を放虫し、蓋をして25℃の定温室内にて飼育した。処理5日後に生死を観察し、死虫率を算出した。
その結果、13、156、196、204、209、215の化合物は80%以上の死虫率を示した。Biological test example 3: Bemisia tabaci control test (foliar spray treatment)
Cucumber leaves were cut into 6.0 cm diameter pieces and placed on absorbent cotton moistened with water. 2 mL of a diluted solution of the test compound diluted with water to a concentration of 200 ppm was sprayed onto the cucumber leaves using a spray tower. After air-drying, the cucumber leaves were placed in a plastic cup, 20 adult female whiteflies were released into the cup, the cup was covered with a lid, and the cup was raised in a constant temperature room at 25°C. Five days after the treatment, the insects were observed to be alive or dead, and the mortality rate was calculated.
As a result, compounds 13, 156, 196, 204, 209, and 215 showed a mortality rate of 80% or more.
生物試験例4:コナガ(Plutella xylostella)防除試験(葉片浸漬処理)
キャベツ葉を直径7.0cmに切り、このキャベツ葉片を200ppmになるように水で希釈した供試化合物の希釈液20mLに浸漬し、風乾した。風乾後、キャベツ葉片をプラスチックカップ内に入れ、10頭のコナガ3令幼虫を放虫し、蓋をして25℃の定温室にて飼育した。処理5日後に幼虫の生死を観察し、死虫率を算出した。
その結果、本発明化合物7、8、37、46、48、55、61、69、78、91、100、101、103、105、106、108、109、110、111、112、113、114、120、125、127、128、129、131、137、139、140、142、152、158、161、175、176、177、178、180、181、188、191、195、199、200、201、204、205、207、209、211、213、214、215、216、217、218、219、220は80%以上の死虫率を示した。Biological test example 4: Plutella xylostella control test (leaf immersion treatment)
Cabbage leaves were cut into pieces with a diameter of 7.0 cm, and the cabbage leaf pieces were immersed in 20 mL of a diluted solution of the test compound diluted with water to a concentration of 200 ppm, and air-dried. After air-drying, the cabbage leaf pieces were placed in a plastic cup, 10 3rd instar diamondback moth larvae were released into the cup, and the cup was covered with a lid and raised in a constant temperature room at 25°C. Five days after the treatment, the larvae were observed to be alive or dead, and the mortality rate was calculated.
As a result, the compounds of the present invention 7, 8, 37, 46, 48, 55, 61, 69, 78, 91, 100, 101, 103, 105, 106, 108, 109, 110, 111, 112, 113, 114, 120, 125, 127, 128, 129, 131, 137, 139, 140, 142, 152, 158, 161, 175, 176, 177, 178, 180, 181, 188, 191, 195, 199, 200, 201, 204, 205, 207, 209, 211, 213, 214, 215, 216, 217, 218, 219, and 220 showed a mortality rate of 80% or more.
生物試験例5:トビイロウンカ(Nilaparvata lugens)防除試験(茎葉浸漬処理)
イネ幼苗を10本取り、200ppmになるように水で希釈した供試化合物の薬液20mLに浸漬し、風乾した。風乾後、ガラス円筒(内径4.5cm×14cm)内にウレタンを用いて保持し、水40mLを入れたプラスチックカップに立てる。これにトビイロウンカ3令幼虫を放飼し、薬包紙にて蓋をし、25℃の定温室にて飼育した。処理5日後に幼虫の生死を観察し、死虫率を算出した。
その結果、本発明化合物1、2、3、4、5、7、10、11、14、16、18、19、20、26、29、31、42、43、44、45、46、48、49、50、51、53、55、59、61、85、86、90、91、98、103、106、152、170、176、181、215は80%以上の死虫率を示した。Biological test example 5: Nilaparvata lugens control test (stem and leaf immersion treatment)
Ten rice seedlings were taken, immersed in 20 mL of a chemical solution of the test compound diluted with water to a concentration of 200 ppm, and air-dried. After air drying, it is held in a glass cylinder (inner diameter 4.5 cm x 14 cm) using urethane and placed upright in a plastic cup filled with 40 mL of water. The 3rd instar larvae of the brown planthopper were released into the container, the container was covered with medical wrapping paper, and the container was raised in a constant temperature room at 25°C. Five days after the treatment, the larvae were observed to be alive or dead, and the mortality rate was calculated.
As a result, the compounds of the present invention 1, 2, 3, 4, 5, 7, 10, 11, 14, 16, 18, 19, 20, 26, 29, 31, 42, 43, 44, 45, 46, 48, 49, 50, 51, 53, 55, 59, 61, 85, 86, 90, 91, 98, 103, 106, 152, 170, 176, 181, and 215 showed a mortality rate of 80% or more.
生物試験例6:セジロウンカ(Sogatella furcifera) 防除試験(根部浸漬処理)
イネ幼苗を10本取り、ガラス円筒(内径4.5cm×14cm)内にウレタンを用いて保持し、3.1ppmの濃度に水で希釈した薬液40mLを入れたプラスチックカップに立てる。2日後、このガラス円筒内にセジロウンカ3令幼虫10頭を放飼し、薬包紙にて蓋をして25℃の定温室内にて飼育した。処理7日後に幼虫の生死を観察し、死虫率を算出した。
その結果、本発明化合物2、3、4、16、20、29、42、47、48、53、55は80%以上の死虫率を示した。Biological test example 6: Green planthopper (Sogatella furcifera) control test (root immersion treatment)
Take 10 rice seedlings, hold them in a glass cylinder (inner diameter 4.5 cm x 14 cm) using urethane, and stand them in a plastic cup containing 40 mL of a chemical solution diluted with water to a concentration of 3.1 ppm. Two days later, 10 3rd instar larvae of the Japanese brown-bottomed planthopper were released into the glass cylinder, covered with medicine wrapper paper, and raised in a constant temperature room at 25°C. Seven days after the treatment, the larvae were observed to be alive or dead, and the mortality rate was calculated.
As a result, compounds of the present invention 2, 3, 4, 16, 20, 29, 42, 47, 48, 53, and 55 showed a mortality rate of 80% or more.
生物試験例7:ハスモンヨトウ(Spodoptera litura)防除試験(茎葉浸漬処理)
キャベツ葉を直径5.0cmに切り、このキャベツ葉片を200ppmになるように水で希釈した供試化合物の希釈液20mLに浸漬し、風乾した。風乾後、キャベツ葉片をプラスチックカップ内に入れ、5頭のハスモンヨトウ2令幼虫を放虫し、蓋をして25℃の定温室にて飼育した。処理5日後に幼虫の生死を観察し、死虫率を算出した。
その結果、本発明化合物91、100、103、106、120、127、131、133、137、139、140、142、148、174、175、176、177、178、180、181、200、201、204、205、207、209、211、213、214、215、216、217、219、220は80%以上の死虫率を示した。Biological test example 7: Spodoptera litura control test (stem and leaf immersion treatment)
Cabbage leaves were cut into pieces with a diameter of 5.0 cm, and the cabbage leaf pieces were immersed in 20 mL of a diluted solution of the test compound diluted with water to a concentration of 200 ppm, and air-dried. After air-drying, the cabbage leaf pieces were placed in a plastic cup, five 2nd instar larvae of Spodoptera were released, and the cup was covered with a lid and reared in a constant temperature room at 25°C. Five days after the treatment, the larvae were observed to be alive or dead, and the mortality rate was calculated.
As a result, the compounds of the present invention 91, 100, 103, 106, 120, 127, 131, 133, 137, 139, 140, 142, 148, 174, 175, 176, 177, 178, 180, 181, 200, 201, 204, 205, 207, 209, 211, 213, 214, 215, 216, 217, 219, and 220 showed a mortality rate of 80% or more.
生物試験例8:キスジノミハムシ(Phyllotreta striolata)防除試験(茎葉浸漬処理)
キャベツ葉を直径2.8cmに切り、このキャベツ葉片を200ppmになるように水で希釈した供試化合物の希釈液20mLに浸漬し、風乾した。風乾後、キャベツ葉片をプラスチックカップ内に入れ、5頭のキスジノミハムシ成虫を放虫し、蓋をして25℃の定温室にて飼育した。処理2日後に成虫の生死を観察し、死虫率及び食害程度を算出した。
その結果、本発明化合物91、100、101、103、106、127、131、133、137、139、140、142、148、174、175、176、177、181、205は80%以上の死虫率もしくは10%以下の食害程度を示した。Biological test example 8: Phyllotreta striolata control test (stem and leaf immersion treatment)
Cabbage leaves were cut into pieces with a diameter of 2.8 cm, and the cabbage leaf pieces were immersed in 20 mL of a diluted solution of the test compound diluted with water to a concentration of 200 ppm, and air-dried. After air-drying, the cabbage leaf pieces were placed in a plastic cup, five adult leaf beetles were released into the cup, the cup was covered with a lid, and the cup was raised in a constant temperature room at 25°C. Two days after the treatment, the adult insects were observed to be alive or dead, and the mortality rate and the degree of feeding damage were calculated.
As a result, compounds of the present invention 91, 100, 101, 103, 106, 127, 131, 133, 137, 139, 140, 142, 148, 174, 175, 176, 177, 181, 205 had more than 80% dead insects. The percentage or the degree of feeding damage was 10% or less.
Claims (28)
[式(1)及び式(3)中、
G1は、(G1-1)、(G1-2)、(G1-3)、(G1-4)又は(G1-5)で表される構造を表し、
G2は、(G2-1)、(G2-2)、(G2-3)、(G2-4)又は(G2-5)で表される構造を表し、
R1、R2、R3及びR4は、各々独立して、水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY1Y2又は-NY1Y2を表し、
A1は、C-RC又はNを表し、
A2は、C-RE又はNを表し、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)
RA、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C3~C6シクロアルキル、Uによって置換された(C3~C6)シクロアルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、5個までのZで置換されても良いフェノキシ基、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY3Y4、-NY3Y4、シアノ、ニトロ、5個までのZで置換されても良いフェニル基、4個までのZで置換されても良いピリジル基、3個までのZで置換されても良いピリミジル基、3個までの置換基で置換されても良いピラジル基、3個までのZで置換されても良いピリダジル基、3個までのZで置換されても良いチエニル基、3個までのZで置換されても良いフラニル基又はVを表し、
Vは、(V-1)、(V-2)、(V-3)、(V-4)、(V-5)又は(V-6)で表される構造を表し、
Zは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY5Y6、シアノ又はニトロを表し、
Q2、Q3又はQ4はZの置換基数を示し、
Q2は、0、1又は2の整数を表し、
Q3は、0、1、2又は3の整数を表し、
Q4は、0、1、2、3又は4の整数を表し、
Q2、Q3又はQ4が2以上の整数を表す場合には、複数のZは互いに同一であっても互いに相異なっていても良く、
Y1、Y2、Y3、Y4、Y5、Y6は、各々独立して、水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルコキシカルボニル、ハロ(C1~C6)アルコキシカルボニル、C1~C6アルキルスルホニル又はハロ(C1~C6)アルキルスルホニルを表し、
Uは、シアノ、-C(O)OH又は-C(O)NH2を表し、
Dは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、C1~C3アルキルオキシカルボニル、ハロ(C1~C3)アルキルオキシカルボニル、5個までのTで置換されても良いベンゼンカルボニルを表し、
Tは各々独立して水素原子、ハロゲン原子、C1~C3アルキル、ハロ(C1~C3)アルキル、C1~C3アルコキシ、ハロ(C1~C3)アルコキシを表し、
Eは水素原子、C1~C6アルキル、シクロプロピルメチル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、メトキシメチル、エトキシメチル、シアノメチル、シアノエチル、メチルチオメチル、メチルスルホニルメチルを表す。] A pest control agent containing a compound represented by formula (1) or formula (3), a salt thereof, or an N-oxide thereof as an active ingredient.
[In formula (1) and formula (3),
G 1 represents a structure represented by (G 1 -1), (G 1 -2), (G 1 -3), (G 1 -4) or (G 1 -5),
G 2 represents a structure represented by (G 2 -1), (G 2 -2), (G 2 -3), (G 2 -4) or (G 2 -5),
R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 1 -C 6 alkoxy, a halo( C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 )alkylsulfonyl, (C=O)NY 1 Y 2 or - represents NY 1 Y 2 ,
A 1 represents C-R C or N,
A 2 represents C-R E or N (here, either A 1 or A 2 is N and the other is C-R C or C-R E ).
R A , R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 3 -C 6 cycloalkyl , (C 3 -C 6 )cycloalkyl substituted by U, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, phenoxy group optionally substituted with up to 5 Z, C 1 -C 6 C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, (C=O)NY 3 Y 4 , -NY 3 Y 4 , cyano, nitro, phenyl group optionally substituted with up to 5 Zs, pyridyl group optionally substituted with up to 4 Zs, Pyrimidyl group optionally substituted with up to 3 Zs, pyrazyl group optionally substituted with up to 3 substituents, pyridazyl group optionally substituted with up to 3 Zs, substituted with up to 3 Zs represents a thienyl group which may be substituted with a thienyl group, a furanyl group which may be substituted with up to 3 Z or V,
V represents a structure represented by (V-1), (V-2), (V-3), (V-4), (V-5) or (V-6),
Z is each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 - C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, -NY 5 Y 6 represents cyano or nitro,
Q2, Q3 or Q4 indicates the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3,
Q4 represents an integer of 0, 1, 2, 3 or 4,
When Q2, Q3 or Q4 represents an integer of 2 or more, the plurality of Z's may be the same or different from each other,
Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 each independently represent a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkyl Carbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo(C 1 -C 6 )alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or halo(C 1 -C 6 )alkylsulfonyl represents,
U represents cyano, -C(O)OH or -C(O) NH2 ,
D is a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, C 1 -C 3 alkyloxycarbonyl, halo(C 1 -C 3 )alkyloxycarbonyl, optionally substituted with up to 5 T Good represents benzenecarbonyl,
Each T independently represents a hydrogen atom, a halogen atom, C 1 -C 3 alkyl, halo(C 1 -C 3 )alkyl, C 1 -C 3 alkoxy, halo(C 1 -C 3 )alkoxy,
E is a hydrogen atom, C1 - C6 alkyl, cyclopropylmethyl, halo( C1 - C6 )alkyl, C1 - C6 alkylcarbonyl, C3 - C6 cycloalkylcarbonyl, halo( C1 -C6 ) ) alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl. ]
[式(1)及び式(3)中、
G1は、(G1-1)、(G1-2)、(G1-3)、(G1-4)又は(G1-5)で表される構造を表し、
G2は、(G2-1)、(G2-2)、(G2-3)、(G2-4)又は(G2-5)で表される構造を表し、
R1、R2、R3及びR4は、各々独立して、水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル又はハロ(C1~C6)アルキルスルホニルを表し、
A1は、C-RC又はNを表し、
A2は、C-RE又はNを表し、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)
RA、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C3~C6シクロアルキル、Uによって置換された(C3~C6)シクロアルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY3Y4、シアノ、ニトロ又はVを表し、
Vは、(V-1)、(V-2)、(V-3)、(V-4)、(V-5)又は(V-6)で表される構造を表し、
Zは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY5Y6、シアノ又はニトロを表し、
Q2、Q3又はQ4はZの置換基数を示し、
Q2は、0、1又は2の整数を表し、
Q3は、0、1、2又は3の整数を表し、
Q4は、0、1、2、3又は4の整数を表し、
Q2、Q3又はQ4が2以上の整数を表す場合には、複数のZは互いに同一であっても互いに相異なっていても良く、
Y3、Y4、Y5、Y6は、各々独立して、水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルコキシカルボニル、ハロ(C1~C6)アルコキシカルボニル、C1~C6アルキルスルホニル又はハロ(C1~C6)アルキルスルホニルを表し、
Uは、複数ある場合には各々独立して、シアノ、-C(O)OH又は-C(O)NH2を表し、
Dは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニルを表し、
Eは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニルを表す。] A pest control agent containing a compound represented by formula (1) or formula (3), a salt thereof, or an N-oxide thereof as an active ingredient.
[In formula (1) and formula (3),
G 1 represents a structure represented by (G 1 -1), (G 1 -2), (G 1 -3), (G 1 -4) or (G 1 -5),
G 2 represents a structure represented by (G 2 -1), (G 2 -2), (G 2 -3), (G 2 -4) or (G 2 -5),
R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 1 -C 6 alkoxy, a halo( C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl or halo(C 1 -C 6 )alkylsulfonyl,
A 1 represents C-R C or N,
A 2 represents C-R E or N (here, either A 1 or A 2 is N and the other is C-R C or C-R E ).
R A , R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 3 -C 6 cycloalkyl , (C 3 -C 6 )cycloalkyl substituted by U, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 -C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, -NY 3 Y 4 , cyano, nitro or V represents,
V represents a structure represented by (V-1), (V-2), (V-3), (V-4), (V-5) or (V-6),
Z is each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 - C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, -NY 5 Y 6 represents cyano or nitro,
Q2, Q3 or Q4 indicates the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3,
Q4 represents an integer of 0, 1, 2, 3 or 4,
When Q2, Q3 or Q4 represents an integer of 2 or more, the plurality of Z's may be the same or different from each other,
Y 3 , Y 4 , Y 5 , and Y 6 each independently represent a hydrogen atom, C 1 to C 6 alkyl, halo(C 1 to C 6 )alkyl, C 1 to C 6 alkylcarbonyl, or halo(C 1 -C 6 ) alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo(C 1 -C 6 )alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or halo(C 1 -C 6 )alkylsulfonyl,
When there is a plurality of U, each independently represents cyano, -C(O)OH or -C(O) NH2 ,
D is a hydrogen atom, C 1 -C 6 alkyl, halo (C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, halo (C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo (C 1 -C 6 ) represents alkylsulfonyl,
E is a hydrogen atom, C 1 -C 6 alkyl, halo (C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, halo (C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo (C 1 -C 6 ) represents alkylsulfonyl. ]
アラニカルブ、アルジカルブ、ベンダイオカルブ、ベンフラカルブ、ブトカルボキシム、ブトキシカルボキシム、カルバリル、カルボフラン、カルボスルファン、エチオフェンカルブ、フェノブカルブ、ホルメタネート、フラチオカルブ、イソプロカルブ、メチオカルブ、メソミル、オキサミル、ピリミカルブ、プロポキスル、チオジカルブ、チオファノックス、トリアザメート、トリメタカルブ、XMC、キシリルカルブ、メトルカルブ、フェノチオカルブ、フェノキシカルブ、アセフェート、アザメチホス、アジンホス-エチル、アジンホス-メチル、エチルチオメトン、クロルエトキシホス、カズサホス、クロレトキシホス、クロルフェンビンホス、クロルメホス、クロルピリホス、クロルピリホスメチル、クマホス、シアノホス、デメトン-S-メチル、ダイアジノン、ジクロルボス、ジクロトホス、ジメトエート、ジメチルビンホス、EPN、エチオン、エトプロホス、ファムフール、フェナミホス、フェニトロチオン、フェンチオン、ホスチアゼート、ヘプテノホス、イミシアホス、イソフェンホス、イソプロピル=O-(メトキシアミノチオホスホリルサリチレート、イソキサチオン、マラチオン、メカルバム、メタミドホス、メチダチオン、メビンホス、モノクロトホス、ナレド、オメトエート、オキシジメトンエチル、パラチオン、パラチオン-メチル、PAP、ホレート、ホサロン、ホスメット、ホスファミドン、ホキシム、ピリミホス-メチル、プロフェノホス、プロペタンホス、プロチオホス、ピラクロホス、ピリダフェンチオン、キナルホス、スルホテップ、テブピリミホス、テメホス、テルブホス、テトラクロルビンホス、チオメトン、トリアゾホス、トリクロルホン、バミドチオン、クロルピリホス-エチル、ジスルフォトン、スルプロホス、フルピラゾホス、フェントエート、ホノホス、トリブホス、エンドスルファン、アルファ-エンドスルファン、ガンマ-HCH、ジコホル、クロルデン、ディルドリン、メトキシクロル、アセトプロール、フィプロニル、エチプロール、ピラフルプロール、ピリプロール、フルフィプロール、ブロフラニリド、アフォキソラネル、フルララネル、サロラネル、フルキサメタミド、ロティラネル、イソシクロシラム、アクリナトリン、アレスリン、d-cis-transアレスリン、d-transアレスリン、ビフェントリン、カッパ-ビフェントリン、ビオアレスリンS-シクロペンテニル、ビオレスメトリン、シクロプロトリン、シフルトリン、ベータ-シフルトリン、シハロトリン、ラムダ-シハロトリン、ガンマ-シハロトリン、シペルメトリン、アルファ-シペルメトリン、ベータ-シペルメトリン、シータ-シペルメトリン、ゼータ-シペルメトリン、シフェノトリン、デルタメトリン、エンペントリン、エスフェンバレレート、エトフェンプロックス、フェンプロパトリン、フェンバレレート、フルシトリネート、フルメトリン、タウ-フルバリネート、ハルフェンプロックス、イミプロトリン、カデスリン、ペルメトリン、フェノトリン、プラレトリン、ピレトリン、レスメトリン、シラフルオフェン、テフルトリン、カッパ-テフルトリン、フタルスリン、テトラメトリン、トラロメトリン、トランスフルトリン、メトキサジアゾン、メトフルトリン、プロフルトリン、ピレトラム、テラレトリン、モンフルオロスリン、ヘプタフルトリン、メペルフルスリン、テトラメチルフルスリン、ジメフルトリン、クロロパラレスリン、イプシロン-メトフルスリン、イプシロン-モンフルオスリン、プロトリフェンブト、アセタミプリド、クロチアニジン、ジノテフラン、イミダクロプリド、ニテンピラム、チアクロプリド、チアメトキサム、スルホキサフロル、フルピラジフロン、トリフルメゾピリム、ジクロロメゾチアズ、フルピリミン、スピノサド、スピネトラム、アバメクチン、イベルメクチン、エマメクチン安息香酸塩、ミルベメクチン、レピメクチン、ヒドロプレン、キノプレン、ジオフェノラン、メトプレン、ピリプロキシフェン、ピメトロジン、フロニカミド、エトキサゾール、ジアフェンチウロン、アゾシクロチン、シヘキサチン、酸化フェンブタスズ、プロパルギット、テトラジホン、クロルフェナピル、トラロピリル、DNOC、ベンスルタップ、カルタップ、チオシクラム、チオスルタップ、チオスルタップ-ナトリウム、ビストリフルロン、クロルフルアズロン、ジフルベンズロン、フルシクロクスロン、フルフェノクスロン、ヘキサフルムロン、ルフェヌロン、ノバルロン、ノビフルムロン、テフルベンズロン、トリフルムロン、ビストリフルロン、ブプロフェジン、シロマジン、クロマフェノジド、ハロフェノジド、メトキシフェノジド、テブフェノジド、アミトラズ、ヒドラメチルノン、アセキノシル、フルアクリピリム、ピリミノストロビン、フルフェノキシストロビン、フェナザキン、フェンピロキシメート、ピリミジフェン、ピリダベン、テブフェンピラド、トルフェンピラド、ピフルブミド、メタフルミゾン、スピロジクロフェン、スピロテトラマト、スピロメシフェン、スピロピディオン、シフルメトフェン、シエノピラフェン、フルベンジアミド、クロラントラニリプロール、シアントラニリプロール、シクラニリプロール、テトラニリプロール、シハロジアミド、テトラクロラントラニリプロール、キノメチオネート、ヘキシチアゾクス、ビフェナゼート、フルフェネリム、ピリフルキナゾン、フロメトキン、フルオピラム、フルアザインドリジン、アミドフルメト、チクロピラゾフロル、チオキサザフェン、オキサゾスルフィル、
ニコチン、クロロピクリン、フッ化スルフリル、クリロチエ、クロフェンテジン、ジフロビダジン、ロテノン、インドキサカルブ、ピペロニルブトキシド、クロルジメホルム、ピリダリル、アザジラクチン、ベンゾキシメート、アフィドピロペン、フルヘキサホン、フルエンスルホン、ベンクロチアズ、カルゾール、殺虫性石鹸、ジメヒポ、ニチアジン、ホウ酸塩、メタアルデヒド、リアノジン、スルフルラミド、アシノナピル、ベンズピリモキサン、3-ブロモ-N-(2,4-ジクロロ-6-(メチルカルバモイル)フェニルイル)-1-(3,5-ジクロロピリジン-2-イル)-1H-ピラゾール-5-カルボキサミド、
メタラキシル、メタラキシル-M、オキサジキシル、オフラセ、ベナラキシル、ベナラキシル-M、キララキシル、オフラース、フララキシル、シプロフラン、ブプリメート、ジメチリモール、エチリモール、ヒメキサゾール、ヒドロキシイソキサゾール、オキサチアピプロリン、オクチリノン、オキソリニック酸、ベノミル、チオファネートメチル、カーベンダジム、フベリダゾール、チアベンダゾール、デバカルブ、ジエトフェンカルブ、ゾキサミド、エタボキサム、ペンシクロン、フルオピコリド、フルオピモミド、ジフルメトリム、ブピリメート、ベノダニル、フルトラニル、メプロニル、イソフェタミド、フェンフラム、オキシカルボキシン、カルボキシン、チフルザミド、フルキサピロキサド、フラメトピル、ペンフルフェン、ペンチオピラド、ベンゾビンジフルピル、ビキサフェン、イソピラザム、セダキサン、インピルフルキサム、フルインダピル、イソフルシプラム、ピラプロポイン、ボスカリド、アゾキシストロビン、コウメトキシストロビン、クレソキシムメチル、トリフロキシストロビン、ピコキシストロビン、ピラクロストロビン、ジモキシストロビン、メトミノストロビン、オリサストロビン、フルオキサストロビン、ピラオキシストロビン、ピラメトストロビン、フルフェノキシストロビン、フェナミンストロビン、エノキサストロビン、クモキシストロビン、マンデストロビン、トリクロピリカルブ、ファモキサドン、フェンアミドン、トリクロピリカルブ、ピリベンカルブ、シアゾファミド、アミスルブロム、ビナパクリル、メプチルジノカルブ、ジノカップ、フルアジナム、フェリムゾン、酢酸-フェンチン、塩化フェンチン、水酸化フェンチン、水酸化トリフェニルスズ、酢酸トリフェニルスズ、オキシン銅、シルチオファム、アメトクトラジン、メパニピリム、ニトラピリン、ピリメサニル、シプロジニル、ブラストサイジンS、カスガマイシン、カスガマイシン塩酸塩水和物、ストレプトマイシン、オキシテトラサイクリン、キノキシフェン、プロキナジド、フルジオキソニル、フェンピクロニル、フルオロイミド、プロシミドン、イプロジオン、ビンクロゾリン、エジフェンホス、イプロベンホス、ピラゾホス、イソプロチオラン、プロパモカルブ、プロパモカルブ塩酸塩、ゴセイカユプテ抽出物、トリホリン、ピリフェノックス、ピリソキサゾール、フェナリモル、ヌアリモル、アザコナゾール、ブロムコナゾール、ジニコナゾール、ジニコナゾール-M、エポキシコナゾール、フルキンコナゾール、オキスポコナゾール、ペフラゾエート、ジフェノコナゾール、フェンブコナゾール、イミベンコナゾール、イプコナゾール、メトコナゾール、テトラコナゾール、トリアジメホン、トリアジメノール、トリチコナゾール、ウニコナゾール、イマザリル、ビテルタノール、トリフルミゾール、エタコナゾール、プロピコナゾール、ペンコナゾール、フルシラゾール、フルトリアホール、ミクロブタニル、パクロブトラゾール、プロチオコナゾール、シプロコナゾール、テブコナゾール、ヘキサコナゾール、プロクロラズ、シメコナゾール、イプフェントリフルコナゾール、アルジモルフ、ドデモルフ、酢酸ドデモルフ、トリデモルフ、フェンプロピモルフ、ジメトモルフ、フルモルフ、ピリモルフ、ピペラリン、フェンプロピディン、スピロキサミン、フェンヘキサミド、フェンピラザミン、フェルバム、メタム、メタスルホカルブ、メチラム、チラム、マンゼブ、マンネブ、ジネブ、ジラム、ポリカーバメート、プロビネブ、チウラム、ピリブチカルブ、バリダマイシン、ミルジオマイシン、ポリオキシン、ベンチアバリカルブ、ベンチアバリカルブイソプロピル、バリフェナレート、イプロバリカルブ、マンジプロパミド、フェンピコキサミド、フロリルピコキサミド、フサライド、ピロキロン、トリシクラゾール、カルプロパミド、ジクロシメット、フェノキサニル、アシベンゾラル-S-メチル、プロベナゾール、ジクロベンチアゾクス、チアジニル、イソチアニル、シモキサニル、ホセチル、テクロフタラム、トリアゾキシド、フルスルファミド、ジクロメジン、シフルフェナミド、メトラフェノン、ピリオフェノン、フルチアニル、テブフロキン、イプフルフェノキン、ホセチルアルミニウム、トルクロホス-メチル、エクロメゾール、トルプロカルブ、メフェントリフルコナゾール、キノフメリン、ピジフルメトフェン、ボルドー混合液、酢酸銅、塩基性硫酸銅、オキシ塩化銅、水酸化第二銅、オキシキノリン銅、銅、硫黄、キャプタン、カプタホール、フォルペット、アニラジン、クロロタロニル、ジクロロフェン、ペンタクロロフェノール及びその塩、ヘキサクロロベンゼン、キントゼン、イミノクタジン酢酸塩、イミノクタジンアルベシル酸塩、グアニジン、ドジン、ドジン遊離塩基、グアザチン、グアザチン酢酸塩、アルベシレート、ジチアノン、フルオルイミド、トリルフルアニド、ジクロフルアニド、ジノブトン、ダゾメット、ピラジフルミド、アミノピリフェン、メチルテトラプロール、ピリダクロメチル、
ジピメチトロン、ピカルブトラゾクス、テクナゼン、ニトルタール-イソプロピル、ジシクロメット、アシベンゾラル、プロヘキサジオン-カルシウム、ブロノポール、ジフェニルアミン、フルメトベル、ベントキサジン、ビフェニル、クロロネブ、CNA、ヨードカルブ、プロチオカルブ、並びに
Bacillus属、及びそれらにより産生された殺虫性タンパク、殺菌性タンパク、Bt作物により産生された殺虫性タンパク、殺菌性タンパク、昆虫病原性バクテリア、昆虫病原性ウイルスおよび昆虫病原性菌類、からなる群から選択される、請求項12に記載の有害生物防除剤。 Said at least one pest control compound or agent is
Aranicarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formanate, furathiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiophyl Nox, triazamate, trimetacarb, XMC, xylylcarb, metolcarb, phenothiocarb, phenoxycarb, acephate, azamethyphos, azinphos-ethyl, azinphos-methyl, ethylthiometone, chlorethoxyfos, cassafos, chlorethoxyfos, chlorfenvinfos, chlormefos, chlorpyrifos, chlorpyrifos-methyl , coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos, dicrotophos, dimethoate, dimethylvinphos, EPN, ethion, ethoprofos, famfur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imisiaphos, isofenphos, isopropyl O-( Methoxyaminothiophosphorylsalicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydimethoneethyl, parathion, parathion-methyl, PAP, phorate, phosalone, phosmet, phosfamidone, phoxim, pirimiphos - Methyl, profenofos, propetanphos, prothiofos, pyraclofos, pyridafenthion, quinalfos, sulfotep, tebupirimifos, temefos, terbufos, tetrachlorvinfos, thiomethone, triazophos, trichlorfon, bamidothione, chlorpyrifos-ethyl, disulfoton, sulprofos, flupyrazofos, fentoate, honofos, Tribufos, endosulfan, alpha-endosulfan, gamma-HCH, dicofol, chlordane, dieldrin, methoxychlor, acetoprol, fipronil, ethiprole, pyrafluprole, pyriprole, flufiprole, brofuranilide, afoxolaner, fluralaner, sarolaner, fluxamethamide, rotilaner, isocyclosilam , acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma- Cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucitrinate , flumethrin, tau-fluvalinate, halfenprox, imiprothrin, cadethrin, permethrin, phenothrin, prarethrin, pyrethrin, resmethrin, cilafluofen, tefluthrin, kappa-tefluthrin, phthalthrin, tetramethrin, tralomethrin, transfluthrin, methoxadiazone, metofluthrin, profluthrin, Pyrethram, telarethrin, monfluorothrin, heptafluthrin, meperfluthrin, tetramethylfluthrin, dimefluthrin, chloropararethrin, epsilon-methfluthrin, epsilon-monfluthrin, protrifenbut, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, Thiacloprid, thiamethoxam, sulfoxaflor, flupyradifurone, triflumezopyrim, dichloromesothiaz, flupyrimine, spinosad, spinetoram, abamectin, ivermectin, emamectin benzoate, milbemectin, lepimectin, hydroprene, quinoprene, diphenolan, methoprene, pyriproxyfen, pymetrozine, flonicamid, etoxazole, diafenthiuron, azocyclotine, cyhexatin, fenbutastin oxide, propargite, tetradifon, chlorfenapyr, tralopyril, DNOC, bensultap, cartap, thiocyclam, thiosultap, thiosultap-sodium, bistrifluron, chlorfluazuron, diflubenzuron, flu Cycloxuron, flufenoxuron, hexaflumuron, lufenuron, Novaluron, noviflumuron, teflubenzuron, triflumuron, bistrifluron, buprofezine, cyromazine, clomafenozide, halofenozide, methoxyfenozide, tebufenozide, amitraz, hydramethylnon, acequinocyl, fluacripyrim, pyrimino Strobin, flufenoxystrobin, fenazaquine, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, pyflubumide, metaflumizone, spirodiclofen, spirotetramate, spiromesifen, spiropidion, cyflumetofen, cyenopyrafen, flubendiamide, chlorantrani Riprole, cyantraniliprole, cyclaniliprole, tetraniliprole, cyhalodiamide, tetrachlorantraniliprole, chinomethionate, hexythiazox, bifenazate, flufenerim, pyrifluquinazone, flomethquine, fluopyram, fluazaindolizine, amidoflumeth, ticlopyrazole Furol, thioxazaphene, oxazosulfil,
Nicotine, chloropicrin, sulfuryl fluoride, krylotie, clofentezine, diflobidazine, rotenone, indoxacarb, piperonyl butoxide, chlordimeform, pyridalyl, azadirachtin, benzoximate, afidopyropene, fluhexaphone, fluensulfone, bencrothiaz, carzole, insecticidal soap, Dimehypo, nithiazine, borate, metaldehyde, ryanodine, sulfuramide, acinonapyr, benzpyrimoxane, 3-bromo-N-(2,4-dichloro-6-(methylcarbamoyl)phenyl)-1-(3, 5-dichloropyridin-2-yl)-1H-pyrazole-5-carboxamide,
Metalaxyl, metalaxyl-M, oxadixyl, ofrase, benalaxyl, benalaxyl-M, chiralaxyl, ofrase, furalaxyl, ciprofuran, buprimate, dimethylimole, ethyrimole, himexazole, hydroxyisoxazole, oxathiapiproline, octyrinone, oxolinic acid, benomyl, thiophanate methyl , carbendazim, fuberidazole, thiabendazole, debacarb, diethofencarb, zoxamide, ethaboxam, pencyclone, fluopicolide, fluopimomide, diflumetrim, bupirimate, benodanil, flutolanil, mepronil, isofetamide, fenflam, oxycarboxin, carboxin, thifluzamide, fluxapiroxad, furametopyr , penflufen, penthiopyrad, benzobine diflupyr, bixafen, isopyrazam, sedaxane, impirfluxam, fluindapir, isoflucipram, pyrapropoin, boscalid, azoxystrobin, coumethoxystrobin, cresoxime methyl, trifloxystrobin, picoxy Strobin, pyraclostrobin, dimoxystrobin, metominostrobin, orysastrobin, fluoxastrobin, pyraoxystrobin, pyramethastrobin, fluphenoxystrobin, phenaminestrobin, enoxastrobin, spideroxystrobin, Mandestrobin, triclopiricarb, famoxadone, fenamidon, triclopiricarb, pyribencarb, cyazofamid, amisulbrome, binapacryl, meptyldinocarb, dinocap, fluazinam, felimzone, fentin acetate, fentin chloride, fentin hydroxide, trihydroxide Phenyltin, triphenyltin acetate, oxine copper, silthiopham, ametoctrazine, mepanipirim, nitrapyrin, pyrimesanil, cyprodinil, blasticidin S, kasugamycin, kasugamycin hydrochloride hydrate, streptomycin, oxytetracycline, quinoxyfen, proquinazide, fludioxonil, fenpiclonil, fluoro Imide, procymidone, iprodione, vinclozolin, edifenphos, iprobenfos, pyrazofos, isoprothiolane, propamocarb, propamocarb hydrochloride, goseicajepute extract, triforine, pyrifenox, pyrisoxazole, fenarimol, nuarimol, azaconazole, bromuconazole, diniconazole, diniconazole-M , epoxiconazole, fluquinconazole, oxpoconazole, pefurazoate, difenoconazole, fenbuconazole, imibenconazole, ipconazole, metconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, imazalil, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, flutriafol, myclobutanil, paclobutrazole, prothioconazole, cyproconazole, tebuconazole, hexaconazole, prochloraz, simeconazole, ipfentrifluconazole, aldimorph, Dodemorph, dodemorph acetate, tridemorph, fenpropimorph, dimethomorph, flumorph, pirimorph, piperaline, fenpropidin, spiroxamine, phenhexamide, fenpyrazamine, ferbam, metham, metasulfocarb, methiram, thiram, mancozeb, maneb, zineb, ziram , polycarbamate, probineb, thiuram, pyributicarb, validamycin, mildiomycin, polyoxin, bentiavaricarb, bentiavaricarb isopropyl, variphenarate, iprovaricarb, mandipropamide, fenpicoxamide, florylpicoxamide, fusaride, Pyroquilone, tricyclazole, carpropamide, diclosymet, phenoxanil, acibenzolar-S-methyl, probenazole, dichlorbenziazox, thiazinil, isotianil, cimoxanil, fosetyl, tecroftalam, triazoxide, fursulfamide, diclomedine, cyflufenamide, metrafenone, piriophenone, flutianil, tebufloquine, iip Flufenoquine, fosetylaluminum, tolclofos-methyl, eclomezole, tolprocarb, mefentrifluconazole, quinofumeline, pydiflumetofen, Bordeaux mixture, copper acetate, basic copper sulfate, copper oxychloride, cupric hydroxide, oxy Quinoline copper, copper, sulfur, captan, captafol, folpet, anilazine, chlorothalonil, dichlorophen, pentachlorophenol and its salts, hexachlorobenzene, quintozene, iminoctadine acetate, iminoctadine albesylate, guanidine, dodine, dodine free base , guazatine, guazatine acetate, albesylate, dithianone, fluorimide, tolylfluanid, dichlofluanid, dibutone, dazomet, pyradiflumide, aminopyrifene, methyltetraprole, pyridacromethyl,
dipimethitron, picarbutrazox, technazen, nitrtal-isopropyl, dicyclomet, acibenzolar, prohexadione-calcium, bronopol, diphenylamine, flumethover, bentoxazine, biphenyl, chloroneb, CNA, iodocarb, prothiocarb, and the genus Bacillus and those produced by them. 13. The insecticidal protein of claim 12 is selected from the group consisting of insecticidal proteins, fungicidal proteins, insecticidal proteins produced by Bt crops, fungicidal proteins, entomopathogenic bacteria, entomopathogenic viruses, and entomopathogenic fungi. Pest control agents listed.
[式(1)及び式(3)中、
G1は、(G1-1)、(G1-2)、(G1-3)、(G1-4)又は(G1-5)で表される構造を表し、
G2は、(G2-1)、(G2-2)、(G2-3)、(G2-4)又は(G2-5)で表される構造を表し、
R1、R2、R3及びR4は、各々独立して、水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY1Y2又は-NY1Y2を表し、
A1は、C-RC又はNを表し、
A2は、C-RE又はNを表し、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)
RA、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C3~C6シクロアルキル、Uによって置換された(C3~C6)シクロアルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、5個までのZで置換されても良いフェノキシ基、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY3Y4、-NY3Y4、シアノ、ニトロ、5個までのZで置換されても良いフェニル基、4個までのZで置換されても良いピリジル基、3個までのZで置換されても良いピリミジル基、3個までの置換基で置換されても良いピラジル基、3個までのZで置換されても良いピリダジル基、3個までのZで置換されても良いチエニル基、3個までのZで置換されても良いフラニル基又はVを表し、
Vは、(V-1)、(V-2)、(V-3)、(V-4)、(V-5)又は(V-6)で表される構造を表し、
Zは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY5Y6、シアノ又はニトロを表し、
Q2、Q3又はQ4はZの置換基数を示し、
Q2は、0、1又は2の整数を表し、
Q3は、0、1、2又は3の整数を表し、
Q4は、0、1、2、3又は4の整数を表し、
Q2、Q3又はQ4が2以上の整数を表す場合には、複数のZは互いに同一であっても互いに相異なっていても良く、
Y1、Y2、Y3、Y4、Y5、Y6は、各々独立して、水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルコキシカルボニル、ハロ(C1~C6)アルコキシカルボニル、C1~C6アルキルスルホニル又はハロ(C1~C6)アルキルスルホニルを表し、
Uは、シアノ、-C(O)OH又は-C(O)NH2を表し、
Dは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、C1~C3アルキルオキシカルボニル、ハロ(C1~C3)アルキルオキシカルボニル、5個までのTで置換されても良いベンゼンカルボニルを表し、
Tは各々独立して水素原子、ハロゲン原子、C1~C3アルキル、ハロ(C1~C3)アルキル、C1~C3アルコキシ、ハロ(C1~C3)アルコキシを表し、
Eは水素原子、C1~C6アルキル、シクロプロピルメチル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、メトキシメチル、エトキシメチル、シアノメチル、シアノエチル、メチルチオメチル、メチルスルホニルメチルを表す。] A method for controlling pests, which involves bringing a compound represented by formula (1) or formula (3), a salt thereof, or an N-oxide thereof into contact with the pest or its environment (however, a method for treating humans) except for).
[In formula (1) and formula (3),
G 1 represents a structure represented by (G 1 -1), (G 1 -2), (G 1 -3), (G 1 -4) or (G 1 -5),
G 2 represents a structure represented by (G 2 -1), (G 2 -2), (G 2 -3), (G 2 -4) or (G 2 -5),
R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 1 -C 6 alkoxy, a halo( C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 )alkylsulfonyl, (C=O)NY 1 Y 2 or - represents NY 1 Y 2 ,
A 1 represents C-R C or N,
A 2 represents C-R E or N (here, either A 1 or A 2 is N and the other is C-R C or C-R E ).
R A , R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 3 -C 6 cycloalkyl , (C 3 -C 6 )cycloalkyl substituted by U, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, phenoxy group optionally substituted with up to 5 Z, C 1 -C 6 C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, (C=O)NY 3 Y 4 , -NY 3 Y 4 , cyano, nitro, phenyl group optionally substituted with up to 5 Zs, pyridyl group optionally substituted with up to 4 Zs, Pyrimidyl group optionally substituted with up to 3 Zs, pyrazyl group optionally substituted with up to 3 substituents, pyridazyl group optionally substituted with up to 3 Zs, substituted with up to 3 Zs represents a thienyl group which may be substituted with a thienyl group, a furanyl group which may be substituted with up to 3 Z or V,
V represents a structure represented by (V-1), (V-2), (V-3), (V-4), (V-5) or (V-6),
Z is each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 - C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, -NY 5 Y 6 represents cyano or nitro,
Q2, Q3 or Q4 indicates the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3,
Q4 represents an integer of 0, 1, 2, 3 or 4,
When Q2, Q3 or Q4 represents an integer of 2 or more, the plurality of Z's may be the same or different from each other,
Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 each independently represent a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkyl Carbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo(C 1 -C 6 )alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or halo(C 1 -C 6 )alkylsulfonyl represents,
U represents cyano, -C(O)OH or -C(O) NH2 ,
D is a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, C 1 -C 3 alkyloxycarbonyl, halo(C 1 -C 3 )alkyloxycarbonyl, optionally substituted with up to 5 T Good represents benzenecarbonyl,
Each T independently represents a hydrogen atom, a halogen atom, C 1 -C 3 alkyl, halo(C 1 -C 3 )alkyl, C 1 -C 3 alkoxy, halo(C 1 -C 3 )alkoxy,
E is a hydrogen atom, C1 - C6 alkyl, cyclopropylmethyl, halo( C1 - C6 )alkyl, C1 - C6 alkylcarbonyl, C3 - C6 cycloalkylcarbonyl, halo( C1 -C6 ) ) alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl. ]
[式(1)及び式(3)中、
G1は、(G1-1)、(G1-2)、(G1-3)、(G1-4)又は(G1-5)で表される構造を表し、
G2は、(G2-1)、(G2-2)、(G2-3)、(G2-4)又は(G2-5)で表される構造を表し、
R1、R2、R3及びR4は、各々独立して、水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY1Y2又は-NY1Y2を表し、
A1は、C-RC又はNを表し、
A2は、C-RE又はNを表し、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)
RA、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C3~C6シクロアルキル、Uによって置換された(C3~C6)シクロアルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、5個までのZで置換されても良いフェノキシ基、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY3Y4、-NY3Y4、シアノ、ニトロ、5個までのZで置換されても良いフェニル基、4個までのZで置換されても良いピリジル基、3個までのZで置換されても良いピリミジル基、3個までの置換基で置換されても良いピラジル基、3個までのZで置換されても良いピリダジル基、3個までのZで置換されても良いチエニル基、3個までのZで置換されても良いフラニル基又はVを表し、
Vは、(V-1)、(V-2)、(V-3)、(V-4)、(V-5)又は(V-6)で表される構造を表し、
Zは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY5Y6、シアノ又はニトロを表し、
Q2、Q3又はQ4はZの置換基数を示し、
Q2は、0、1又は2の整数を表し、
Q3は、0、1、2又は3の整数を表し、
Q4は、0、1、2、3又は4の整数を表し、
Q2、Q3又はQ4が2以上の整数を表す場合には、複数のZは互いに同一であっても互いに相異なっていても良く、
Y1、Y2、Y3、Y4、Y5、Y6は、各々独立して、水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルコキシカルボニル、ハロ(C1~C6)アルコキシカルボニル、C1~C6アルキルスルホニル又はハロ(C1~C6)アルキルスルホニルを表し、
Uは、シアノ、-C(O)OH又は-C(O)NH2を表し、
Dは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、C1~C3アルキルオキシカルボニル、ハロ(C1~C3)アルキルオキシカルボニル、5個までのTで置換されても良いベンゼンカルボニルを表し、
Tは各々独立して水素原子、ハロゲン原子、C1~C3アルキル、ハロ(C1~C3)アルキル、C1~C3アルコキシ、ハロ(C1~C3)アルコキシを表し、
Eは水素原子、C1~C6アルキル、シクロプロピルメチル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、メトキシメチル、エトキシメチル、シアノメチル、シアノエチル、メチルチオメチル、メチルスルホニルメチルを表す。] A method for increasing the vigor of crops, the method comprising contacting crops or seeds of crops with a compound represented by formula (1) or formula (3), a salt thereof, or an N-oxide thereof.
[In formula (1) and formula (3),
G 1 represents a structure represented by (G 1 -1), (G 1 -2), (G 1 -3), (G 1 -4) or (G 1 -5),
G 2 represents a structure represented by (G 2 -1), (G 2 -2), (G 2 -3), (G 2 -4) or (G 2 -5),
R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 1 -C 6 alkoxy, a halo( C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 )alkylsulfonyl, (C=O)NY 1 Y 2 or - represents NY 1 Y 2 ,
A 1 represents C-R C or N,
A 2 represents C-R E or N (here, either A 1 or A 2 is N and the other is C-R C or C-R E ).
R A , R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 3 -C 6 cycloalkyl , (C 3 -C 6 )cycloalkyl substituted by U, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, phenoxy group optionally substituted with up to 5 Z, C 1 -C 6 C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, (C=O)NY 3 Y 4 , -NY 3 Y 4 , cyano, nitro, phenyl group optionally substituted with up to 5 Zs, pyridyl group optionally substituted with up to 4 Zs, Pyrimidyl group optionally substituted with up to 3 Zs, pyrazyl group optionally substituted with up to 3 substituents, pyridazyl group optionally substituted with up to 3 Zs, substituted with up to 3 Zs represents a thienyl group which may be substituted with Z, a furanyl group which may be substituted with up to 3 Z or V,
V represents a structure represented by (V-1), (V-2), (V-3), (V-4), (V-5) or (V-6),
Z is each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 - C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, -NY 5 Y 6 represents cyano or nitro,
Q2, Q3 or Q4 indicates the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3,
Q4 represents an integer of 0, 1, 2, 3 or 4,
When Q2, Q3 or Q4 represents an integer of 2 or more, the plurality of Z's may be the same or different from each other,
Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 each independently represent a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkyl Carbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo(C 1 -C 6 )alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or halo(C 1 -C 6 )alkylsulfonyl represents,
U represents cyano, -C(O)OH or -C(O) NH2 ,
D is a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, C 1 -C 3 alkyloxycarbonyl, halo(C 1 -C 3 )alkyloxycarbonyl, optionally substituted with up to 5 T Good represents benzenecarbonyl,
Each T independently represents a hydrogen atom, a halogen atom, C 1 -C 3 alkyl, halo(C 1 -C 3 )alkyl, C 1 -C 3 alkoxy, halo(C 1 -C 3 )alkoxy,
E is a hydrogen atom, C1 - C6 alkyl, cyclopropylmethyl, halo( C1 - C6 )alkyl, C1 - C6 alkylcarbonyl, C3 - C6 cycloalkylcarbonyl, halo( C1 -C6 ) ) alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl. ]
[式(1)及び式(3)中、
G1は、(G1-1)、(G1-2)、(G1-3)、(G1-4)又は(G1-5)で表される構造を表し、
G2は、(G2-1)、(G2-2)、(G2-3)、(G2-4)又は(G2-5)で表される構造を表し、
R1、R2、R3及びR4は、各々独立して、水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY1Y2又は-NY1Y2を表し、
A1は、C-RC又はNを表し、
A2は、C-RE又はNを表し、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)
RA、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C3~C6シクロアルキル、Uによって置換された(C3~C6)シクロアルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、5個までのZで置換されても良いフェノキシ基、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY3Y4、-NY3Y4、シアノ、ニトロ、5個までのZで置換されても良いフェニル基、4個までのZで置換されても良いピリジル基、3個までのZで置換されても良いピリミジル基、3個までの置換基で置換されても良いピラジル基、3個までのZで置換されても良いピリダジル基、3個までのZで置換されても良いチエニル基、3個までのZで置換されても良いフラニル基又はVを表し、
Vは、(V-1)、(V-2)、(V-3)、(V-4)、(V-5)又は(V-6)で表される構造を表し、
Zは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY5Y6、シアノ又はニトロを表し、
Q2、Q3又はQ4はZの置換基数を示し、
Q2は、0、1又は2の整数を表し、
Q3は、0、1、2又は3の整数を表し、
Q4は、0、1、2、3又は4の整数を表し、
Q2、Q3又はQ4が2以上の整数を表す場合には、複数のZは互いに同一であっても互いに相異なっていても良く、
Y1、Y2、Y3、Y4、Y5、Y6は、各々独立して、水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルコキシカルボニル、ハロ(C1~C6)アルコキシカルボニル、C1~C6アルキルスルホニル又はハロ(C1~C6)アルキルスルホニルを表し、
Uは、シアノ、-C(O)OH又は-C(O)NH2を表し、
Dは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、C1~C3アルキルオキシカルボニル、ハロ(C1~C3)アルキルオキシカルボニル、5個までのTで置換されても良いベンゼンカルボニルを表し、
Tは各々独立して水素原子、ハロゲン原子、C1~C3アルキル、ハロ(C1~C3)アルキル、C1~C3アルコキシ、ハロ(C1~C3)アルコキシを表し、
Eは水素原子、C1~C6アルキル、シクロプロピルメチル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、メトキシメチル、エトキシメチル、シアノメチル、シアノエチル、メチルチオメチル、メチルスルホニルメチルを表す。] Seeds treated with a compound represented by formula (1) or formula (3), a salt thereof, or an N-oxide thereof, wherein the compound is present in an amount of 0.0001 to 50% by weight of the whole seed after treatment. or a salt thereof or an N-oxide thereof.
[In formula (1) and formula (3),
G 1 represents a structure represented by (G 1 -1), (G 1 -2), (G 1 -3), (G 1 -4) or (G 1 -5),
G 2 represents a structure represented by (G 2 -1), (G 2 -2), (G 2 -3), (G 2 -4) or (G 2 -5),
R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 1 -C 6 alkoxy, a halo( C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 )alkylsulfonyl, (C=O)NY 1 Y 2 or - represents NY 1 Y 2 ,
A 1 represents C-R C or N,
A 2 represents C-R E or N (here, either A 1 or A 2 is N and the other is C-R C or C-R E ).
R A , R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 3 -C 6 cycloalkyl , (C 3 -C 6 )cycloalkyl substituted by U, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, phenoxy group optionally substituted with up to 5 Z, C 1 -C 6 C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, (C=O)NY 3 Y 4 , -NY 3 Y 4 , cyano, nitro, phenyl group optionally substituted with up to 5 Zs, pyridyl group optionally substituted with up to 4 Zs, Pyrimidyl group optionally substituted with up to 3 Zs, pyrazyl group optionally substituted with up to 3 substituents, pyridazyl group optionally substituted with up to 3 Zs, substituted with up to 3 Zs represents a thienyl group which may be substituted with a thienyl group, a furanyl group which may be substituted with up to 3 Z or V,
V represents a structure represented by (V-1), (V-2), (V-3), (V-4), (V-5) or (V-6),
Z is each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 - C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, -NY 5 Y 6 represents cyano or nitro,
Q2, Q3 or Q4 indicates the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3,
Q4 represents an integer of 0, 1, 2, 3 or 4,
When Q2, Q3 or Q4 represents an integer of 2 or more, the plurality of Z's may be the same or different from each other,
Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 each independently represent a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkyl Carbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo(C 1 -C 6 )alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or halo(C 1 -C 6 )alkylsulfonyl represents,
U represents cyano, -C(O)OH or -C(O) NH2 ,
D is a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, C 1 -C 3 alkyloxycarbonyl, halo(C 1 -C 3 )alkyloxycarbonyl, optionally substituted with up to 5 T Good represents benzenecarbonyl,
Each T independently represents a hydrogen atom, a halogen atom, C 1 -C 3 alkyl, halo(C 1 -C 3 )alkyl, C 1 -C 3 alkoxy, halo(C 1 -C 3 )alkoxy,
E is a hydrogen atom, C1 - C6 alkyl, cyclopropylmethyl, halo( C1 - C6 )alkyl, C1 - C6 alkylcarbonyl, C3 - C6 cycloalkylcarbonyl, halo( C1 -C6 ) ) alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl. ]
処理後の種子が種子全体の0.0001~50重量%の量の前記化合物若しくはその塩又はそれらのN-オキシドを含む、
前記方法。
[式(1)及び式(3)中、
G1は、(G1-1)、(G1-2)、(G1-3)、(G1-4)又は(G1-5)で表される構造を表し、
G2は、(G2-1)、(G2-2)、(G2-3)、(G2-4)又は(G2-5)で表される構造を表し、
R1、R2、R3及びR4は、各々独立して、水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY1Y2又は-NY1Y2を表し、
A1は、C-RC又はNを表し、
A2は、C-RE又はNを表し、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)
RA、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C3~C6シクロアルキル、Uによって置換された(C3~C6)シクロアルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、5個までのZで置換されても良いフェノキシ基、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY3Y4、-NY3Y4、シアノ、ニトロ、5個までのZで置換されても良いフェニル基、4個までのZで置換されても良いピリジル基、3個までのZで置換されても良いピリミジル基、3個までの置換基で置換されても良いピラジル基、3個までのZで置換されても良いピリダジル基、3個までのZで置換されても良いチエニル基、3個までのZで置換されても良いフラニル基又はVを表し、
Vは、(V-1)、(V-2)、(V-3)、(V-4)、(V-5)又は(V-6)で表される構造を表し、
Zは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY5Y6、シアノ又はニトロを表し、
Q2、Q3又はQ4はZの置換基数を示し、
Q2は、0、1又は2の整数を表し、
Q3は、0、1、2又は3の整数を表し、
Q4は、0、1、2、3又は4の整数を表し、
Q2、Q3又はQ4が2以上の整数を表す場合には、複数のZは互いに同一であっても互いに相異なっていても良く、
Y1、Y2、Y3、Y4、Y5、Y6は、各々独立して、水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルコキシカルボニル、ハロ(C1~C6)アルコキシカルボニル、C1~C6アルキルスルホニル又はハロ(C1~C6)アルキルスルホニルを表し、
Uは、シアノ、-C(O)OH又は-C(O)NH2を表し、
Dは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、C1~C3アルキルオキシカルボニル、ハロ(C1~C3)アルキルオキシカルボニル、5個までのTで置換されても良いベンゼンカルボニルを表し、
Tは各々独立して水素原子、ハロゲン原子、C1~C3アルキル、ハロ(C1~C3)アルキル、C1~C3アルコキシ、ハロ(C1~C3)アルコキシを表し、
Eは水素原子、C1~C6アルキル、シクロプロピルメチル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、メトキシメチル、エトキシメチル、シアノメチル、シアノエチル、メチルチオメチル、メチルスルホニルメチルを表す。] The method for producing seeds according to claim 17 , comprising the step of treating crop seeds with a compound represented by formula (1) or formula (3), a salt thereof, or an N-oxide thereof,
The treated seeds contain the compound or its salt or its N-oxide in an amount of 0.0001 to 50% by weight of the whole seed,
Said method.
[In formula (1) and formula (3),
G 1 represents a structure represented by (G 1 -1), (G 1 -2), (G 1 -3), (G 1 -4) or (G 1 -5),
G 2 represents a structure represented by (G 2 -1), (G 2 -2), (G 2 -3), (G 2 -4) or (G 2 -5),
R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 1 -C 6 alkoxy, a halo( C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 )alkylsulfonyl, (C=O)NY 1 Y 2 or - represents NY 1 Y 2 ,
A 1 represents C-R C or N,
A 2 represents C-R E or N (here, either A 1 or A 2 is N and the other is C-R C or C-R E ).
R A , R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 3 -C 6 cycloalkyl , (C 3 -C 6 )cycloalkyl substituted by U, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, phenoxy group optionally substituted with up to 5 Z, C 1 -C 6 C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, (C=O)NY 3 Y 4 , -NY 3 Y 4 , cyano, nitro, phenyl group optionally substituted with up to 5 Zs, pyridyl group optionally substituted with up to 4 Zs, Pyrimidyl group optionally substituted with up to 3 Zs, pyrazyl group optionally substituted with up to 3 substituents, pyridazyl group optionally substituted with up to 3 Zs, substituted with up to 3 Zs represents a thienyl group which may be substituted with a thienyl group, a furanyl group which may be substituted with up to 3 Z or V,
V represents a structure represented by (V-1), (V-2), (V-3), (V-4), (V-5) or (V-6),
Z is each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 - C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, -NY 5 Y 6 represents cyano or nitro,
Q2, Q3 or Q4 indicates the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3,
Q4 represents an integer of 0, 1, 2, 3 or 4,
When Q2, Q3 or Q4 represents an integer of 2 or more, the plurality of Z's may be the same or different from each other,
Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 each independently represent a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkyl Carbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo(C 1 -C 6 )alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or halo(C 1 -C 6 )alkylsulfonyl represents,
U represents cyano, -C(O)OH or -C(O) NH2 ,
D is a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, C 1 -C 3 alkyloxycarbonyl, halo(C 1 -C 3 )alkyloxycarbonyl, optionally substituted with up to 5 T Good represents benzenecarbonyl,
Each T independently represents a hydrogen atom, a halogen atom, C 1 -C 3 alkyl, halo(C 1 -C 3 )alkyl, C 1 -C 3 alkoxy, halo(C 1 -C 3 )alkoxy,
E is a hydrogen atom, C1 - C6 alkyl, cyclopropylmethyl, halo( C1 - C6 )alkyl, C1 - C6 alkylcarbonyl, C3 - C6 cycloalkylcarbonyl, halo( C1 -C6 ) ) alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl. ]
[式(1)及び式(3)中、
G1は、(G1-1)、(G1-2)、(G1-3)、(G1-4)又は(G1-5)で表される構造を表し、
G2は、(G2-1)、(G2-2)、(G2-3)、(G2-4)又は(G2-5)で表される構造を表し、
R1、R2、R3及びR4について、各々独立して、その少なくとも1つは、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY1Y2又は-NY1Y2を表し、
その他は、水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY1Y2又は-NY1Y2を表し、
A1は、C-RC又はNを表し、
A2は、C-RE又はNを表し、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)
RA、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C3~C6シクロアルキル、Uによって置換された(C3~C6)シクロアルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、5個までのZで置換されても良いフェノキシ基、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、(C=O)NY3Y4、-NY3Y4、シアノ、ニトロ、5個までのZで置換されても良いフェニル基、4個までのZで置換されても良いピリジル基、3個までのZで置換されても良いピリミジル基、3個までの置換基で置換されても良いピラジル基、3個までのZで置換されても良いピリダジル基、3個までのZで置換されても良いチエニル基、3個までのZで置換されても良いフラニル基又はVを表し、
Vは、(V-1)、(V-2)、(V-3)、(V-4)、(V-5)又は(V-6)で表される構造を表し、
Zは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY5Y6、シアノ又はニトロを表し、
Q2、Q3又はQ4はZの置換基数を示し、
Q2は、0、1又は2の整数を表し、
Q3は、0、1、2又は3の整数を表し、
Q4は、0、1、2、3又は4の整数を表し、
Q2、Q3又はQ4が2以上の整数を表す場合には、複数のZは互いに同一であっても互いに相異なっていても良く、
Y1、Y2、Y3、Y4、Y5、Y6は、各々独立して、水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルコキシカルボニル、ハロ(C1~C6)アルコキシカルボニル、C1~C6アルキルスルホニル又はハロ(C1~C6)アルキルスルホニルを表し、
Uは、シアノ、-C(O)OH又は-C(O)NH2を表し、
Dは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、C1~C3アルキルオキシカルボニル、ハロ(C1~C3)アルキルオキシカルボニル、5個までのTで置換されても良いベンゼンカルボニルを表し、
Tは各々独立して水素原子、ハロゲン原子、C1~C3アルキル、ハロ(C1~C3)アルキル、C1~C3アルコキシ、ハロ(C1~C3)アルコキシを表し、
Eは水素原子、C1~C6アルキル、シクロプロピルメチル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、C3~C6シクロアルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、メトキシメチル、エトキシメチル、シアノメチル、シアノエチル、メチルチオメチル、メチルスルホニルメチルを表す。] A compound represented by formula (1) or formula (3), a salt thereof, or an N-oxide thereof.
[In formula (1) and formula (3),
G 1 represents a structure represented by (G 1 -1), (G 1 -2), (G 1 -3), (G 1 -4) or (G 1 -5),
G 2 represents a structure represented by (G 2 -1), (G 2 -2), (G 2 -3), (G 2 -4) or (G 2 -5),
For each of R 1 , R 2 , R 3 and R 4 , independently, at least one of them is halo(C 1 -C 6 )alkyl, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy , represents halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 )alkylsulfonyl, (C=O)NY 1 Y 2 or -NY 1 Y 2 ,
Others include hydrogen atoms, halogen atoms, C 1 -C 6 alkyl, halo (C 1 -C 6 ) alkyl, C 1 -C 6 alkoxy, halo (C 1 -C 6 )alkoxy, halo (C 1 -C 6 ) ) represents alkylthio, halo(C 1 -C 6 )alkylsulfinyl, halo(C 1 -C 6 )alkylsulfonyl, (C=O)NY 1 Y 2 or -NY 1 Y 2 ,
A 1 represents C-R C or N,
A 2 represents C-R E or N (here, either A 1 or A 2 is N and the other is C-R C or C-R E ).
R A , R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 3 -C 6 cycloalkyl , (C 3 -C 6 )cycloalkyl substituted by U, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, phenoxy group optionally substituted with up to 5 Z, C 1 -C 6 C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, (C=O)NY 3 Y 4 , -NY 3 Y 4 , cyano, nitro, phenyl group optionally substituted with up to 5 Zs, pyridyl group optionally substituted with up to 4 Zs, Pyrimidyl group optionally substituted with up to 3 Zs, pyrazyl group optionally substituted with up to 3 substituents, pyridazyl group optionally substituted with up to 3 Zs, substituted with up to 3 Zs represents a thienyl group which may be substituted with a thienyl group, a furanyl group which may be substituted with up to 3 Z or V,
V represents a structure represented by (V-1), (V-2), (V-3), (V-4), (V-5) or (V-6),
Z is each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 - C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, -NY 5 Y 6 represents cyano or nitro,
Q2, Q3 or Q4 indicates the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3,
Q4 represents an integer of 0, 1, 2, 3 or 4,
When Q2, Q3 or Q4 represents an integer of 2 or more, the plurality of Z's may be the same or different from each other,
Y 1 , Y 2 , Y 3 , Y 4 , Y 5 and Y 6 each independently represent a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkyl Carbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo(C 1 -C 6 )alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or halo(C 1 -C 6 )alkylsulfonyl represents,
U represents cyano, -C(O)OH or -C(O) NH2 ,
D is a hydrogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, halo(C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, C 1 -C 3 alkyloxycarbonyl, halo(C 1 -C 3 )alkyloxycarbonyl, optionally substituted with up to 5 T Good represents benzenecarbonyl,
Each T independently represents a hydrogen atom, a halogen atom, C 1 -C 3 alkyl, halo(C 1 -C 3 )alkyl, C 1 -C 3 alkoxy, halo(C 1 -C 3 )alkoxy,
E is a hydrogen atom, C1 - C6 alkyl, cyclopropylmethyl, halo( C1 - C6 )alkyl, C1 - C6 alkylcarbonyl, C3 - C6 cycloalkylcarbonyl, halo( C1 -C6 ) ) alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, methoxymethyl, ethoxymethyl, cyanomethyl, cyanoethyl, methylthiomethyl, methylsulfonylmethyl. ]
[式(1)及び式(3)中、
G1は、(G1-1)、(G1-2)、(G1-3)、(G1-4)又は(G1-5)で表される構造を表し、
G2は、(G2-1)、(G2-2)、(G2-3)、(G2-4)又は(G2-5)で表される構造を表し、
R1、R2、R3及びR4について、各々独立して、その少なくとも1つは、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル又はハロ(C1~C6)アルキルスルホニルを表し、
その他は、水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、ハロ(C1~C6)アルキルチオ、ハロ(C1~C6)アルキルスルフィニル又はハロ(C1~C6)アルキルスルホニルを表し、
A1は、C-RC又はNを表し、
A2は、C-RE又はNを表し、(ここで、A1、A2のどちらか一方はNであり、もう一方はC-RC又はC-REである。)
RA、RB、RC、RD及びREは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C3~C6シクロアルキル、Uによって置換された(C3~C6)シクロアルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY3Y4、シアノ、ニトロ又はVを表し、
Vは、(V-1)、(V-2)、(V-3)、(V-4)、(V-5)又は(V-6)で表される構造を表し、
Zは、各々独立して水素原子、ハロゲン原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルコキシ、ハロ(C1~C6)アルコキシ、C1~C6アルキルチオ、ハロ(C1~C6)アルキルチオ、C1~C6アルキルスルフィニル、ハロ(C1~C6)アルキルスルフィニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニル、-NY5Y6、シアノ又はニトロを表し、
Q2、Q3又はQ4はZの置換基数を示し、
Q2は、0、1又は2の整数を表し、
Q3は、0、1、2又は3の整数を表し、
Q4は、0、1、2、3又は4の整数を表し、
Q2、Q3又はQ4が2以上の整数を表す場合には、複数のZは互いに同一であっても互いに相異なっていても良く、
Y3、Y4、Y5、Y6は、各々独立して、水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルコキシカルボニル、ハロ(C1~C6)アルコキシカルボニル、C1~C6アルキルスルホニル又はハロ(C1~C6)アルキルスルホニルを表し、
Uは、複数ある場合には各々独立して、シアノ、-C(O)OH又は-C(O)NH2を表し、
Dは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニルを表し、
Eは水素原子、C1~C6アルキル、ハロ(C1~C6)アルキル、C1~C6アルキルカルボニル、ハロ(C1~C6)アルキルカルボニル、C1~C6アルキルスルホニル、ハロ(C1~C6)アルキルスルホニルを表す。] A compound represented by formula (1) or formula (3), a salt thereof, or an N-oxide thereof.
[In formula (1) and formula (3),
G 1 represents a structure represented by (G 1 -1), (G 1 -2), (G 1 -3), (G 1 -4) or (G 1 -5),
G 2 represents a structure represented by (G 2 -1), (G 2 -2), (G 2 -3), (G 2 -4) or (G 2 -5),
For each of R 1 , R 2 , R 3 and R 4 , independently, at least one of them is halo(C 1 -C 6 )alkyl, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy , represents halo(C 1 -C 6 )alkylthio, halo(C 1 -C 6 )alkylsulfinyl or halo(C 1 -C 6 )alkylsulfonyl,
Others include hydrogen atoms, halogen atoms, C 1 -C 6 alkyl, halo (C 1 -C 6 ) alkyl, C 1 -C 6 alkoxy, halo (C 1 -C 6 )alkoxy, halo (C 1 -C 6 ) ) represents alkylthio, halo(C 1 -C 6 )alkylsulfinyl or halo(C 1 -C 6 )alkylsulfonyl,
A 1 represents C-R C or N,
A 2 represents C-R E or N (here, either A 1 or A 2 is N and the other is C-R C or C-R E ).
R A , R B , R C , R D and R E each independently represent a hydrogen atom, a halogen atom, a C 1 -C 6 alkyl, a halo(C 1 -C 6 )alkyl, a C 3 -C 6 cycloalkyl , (C 3 -C 6 )cycloalkyl substituted by U, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 -C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkylsulfonyl, -NY 3 Y 4 , cyano, nitro or V represents,
V represents a structure represented by (V-1), (V-2), (V-3), (V-4), (V-5) or (V-6),
Z is each independently a hydrogen atom, a halogen atom, C 1 -C 6 alkyl, halo(C 1 -C 6 )alkyl, C 1 -C 6 alkoxy, halo(C 1 -C 6 )alkoxy, C 1 - C 6 alkylthio, halo(C 1 -C 6 )alkylthio, C 1 -C 6 alkylsulfinyl, halo(C 1 -C 6 )alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo(C 1 -C 6 )alkyl Sulfonyl, -NY 5 Y 6 represents cyano or nitro,
Q2, Q3 or Q4 indicates the number of substituents of Z,
Q2 represents an integer of 0, 1 or 2,
Q3 represents an integer of 0, 1, 2 or 3,
Q4 represents an integer of 0, 1, 2, 3 or 4,
When Q2, Q3 or Q4 represents an integer of 2 or more, the plurality of Z's may be the same or different from each other,
Y 3 , Y 4 , Y 5 , and Y 6 each independently represent a hydrogen atom, C 1 to C 6 alkyl, halo(C 1 to C 6 )alkyl, C 1 to C 6 alkylcarbonyl, or halo(C 1 -C 6 ) alkylcarbonyl, C 1 -C 6 alkoxycarbonyl, halo(C 1 -C 6 )alkoxycarbonyl, C 1 -C 6 alkylsulfonyl or halo(C 1 -C 6 )alkylsulfonyl,
When there is a plurality of U, each independently represents cyano, -C(O)OH or -C(O) NH2 ,
D is a hydrogen atom, C 1 -C 6 alkyl, halo (C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, halo (C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo (C 1 -C 6 ) represents alkylsulfonyl,
E is a hydrogen atom, C 1 -C 6 alkyl, halo (C 1 -C 6 )alkyl, C 1 -C 6 alkylcarbonyl, halo (C 1 -C 6 )alkylcarbonyl, C 1 -C 6 alkylsulfonyl, halo (C 1 -C 6 ) represents alkylsulfonyl. ]
The compound or a salt thereof according to claim 19, or a salt thereof, or a salt thereof, represented by formula (3) in which G 2 is (G 2 -1), A 1 is CR C , and A 2 is N. N-oxide.
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