WO2024005032A1 - Azepandione derivative or salt thereof, harmful organism control agent containing said compound, and method for using same - Google Patents
Azepandione derivative or salt thereof, harmful organism control agent containing said compound, and method for using same Download PDFInfo
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- WO2024005032A1 WO2024005032A1 PCT/JP2023/023869 JP2023023869W WO2024005032A1 WO 2024005032 A1 WO2024005032 A1 WO 2024005032A1 JP 2023023869 W JP2023023869 W JP 2023023869W WO 2024005032 A1 WO2024005032 A1 WO 2024005032A1
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- MEBQXILRKZHVCX-UHFFFAOYSA-N methidathion Chemical compound COC1=NN(CSP(=S)(OC)OC)C(=O)S1 MEBQXILRKZHVCX-UHFFFAOYSA-N 0.000 description 1
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- FWJLFUVWQAXWLE-UHFFFAOYSA-N methometon Chemical compound COCCCNC1=NC(NCCCOC)=NC(OC)=N1 FWJLFUVWQAXWLE-UHFFFAOYSA-N 0.000 description 1
- UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- GEPDYQSQVLXLEU-AATRIKPKSA-N methyl (e)-3-dimethoxyphosphoryloxybut-2-enoate Chemical compound COC(=O)\C=C(/C)OP(=O)(OC)OC GEPDYQSQVLXLEU-AATRIKPKSA-N 0.000 description 1
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
- NIFKBBMCXCMCAO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate Chemical group COC(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NIFKBBMCXCMCAO-UHFFFAOYSA-N 0.000 description 1
- JTHMVYBOQLDDIY-UHFFFAOYSA-N methyl 2-[(4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carbonyl)sulfamoyl]benzoate Chemical compound O=C1N(C)C(OCCC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC JTHMVYBOQLDDIY-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- LYPWWQLKWQNQKV-UHFFFAOYSA-N methyl 2-[5-ethyl-2-[[4-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]methyl]phenoxy]propanoate Chemical compound COC(=O)C(C)OC1=CC(CC)=CC=C1COC1=CC=C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)C=C1 LYPWWQLKWQNQKV-UHFFFAOYSA-N 0.000 description 1
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 1
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- IHNSIFFSNUQGQN-UHFFFAOYSA-N tioxazafen Chemical compound C1=CSC(C=2ON=C(N=2)C=2C=CC=CC=2)=C1 IHNSIFFSNUQGQN-UHFFFAOYSA-N 0.000 description 1
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- YJINQJFQLQIYHX-UHFFFAOYSA-N trans-11-tetradecenyl acetate Natural products CCC=CCCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-UHFFFAOYSA-N 0.000 description 1
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- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 229960000323 triclabendazole Drugs 0.000 description 1
- QFNFRZHOXWNWAQ-UHFFFAOYSA-N triclopyricarb Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NC(Cl)=C(Cl)C=C1Cl QFNFRZHOXWNWAQ-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
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- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- PIHCREFCPDWIPY-UHFFFAOYSA-N tris[2-(2,4-dichlorophenoxy)ethyl] phosphite Chemical compound ClC1=CC(Cl)=CC=C1OCCOP(OCCOC=1C(=CC(Cl)=CC=1)Cl)OCCOC1=CC=C(Cl)C=C1Cl PIHCREFCPDWIPY-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 210000003812 trophozoite Anatomy 0.000 description 1
- 239000002753 trypsin inhibitor Substances 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
- 229940125120 umifoxolaner Drugs 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
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 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
- 239000000273 veterinary drug Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
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- A—HUMAN NECESSITIES
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- 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
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/16—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof the nitrogen atom being part of a heterocyclic ring
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/04—Insecticides
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- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
- C07D223/08—Oxygen atoms
- C07D223/10—Oxygen atoms attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Definitions
- the present invention relates to an azepanedione derivative or a salt thereof, a pest control agent containing the compound, and a method for using the same.
- Patent Documents 1 and 2 report certain azepanedione derivatives as pharmaceutical compounds. Furthermore, Patent Document 3 reports certain azepanedione derivatives as intermediates for pharmaceutical compounds. However, these documents do not describe or suggest the control activity of these compounds against harmful organisms such as pests in the field of agriculture and horticulture and parasites of animals.
- the present inventors have conducted intensive research to develop new pest control agents, particularly agricultural and horticultural pest control agents, animal ectoparasite control agents, and animal endoparasite control agents.
- the present invention was completed based on the discovery that a compound having an azepane-2,4-dione derivative as the carboxylic acid moiety of the carboxamide represented by formula (1) or a salt thereof is useful as a pest control agent.
- R 1 is (a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 - C 6 ) cycloalkyl group; (a6) halo (C 1 - C 6 ) alkyl group; (a7) halo (C 2 - C 6 ) alkenyl group; (a8) halo (C 2 - C 6 ) alkynyl group (a9) halo(C 3 -C 6 )cycloalkyl group; (a10) substituted (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (a11) Substituted (C 3 - C 6 ) cycloalkyl group having 1 to 3 substituents each independently selected from substituent group A; (a11) Substituted (
- R 2a is (b1) A hydrogen atom; or (b2) a (C 1 -C 6 ) alkyl group.
- R2b is (c1) A hydrogen atom; or (c2) a (C 1 -C 6 ) alkyl group.
- R 3a is (d1) Hydrogen atom; (d2) (C 1 -C 6 ) alkyl group; (d3) Phenyl group; or (d4) Halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) Substituted phenyl having 1 to 5 substituents on the ring, each independently selected from the group consisting of an alkoxy group, a halo(C 1 -C 6 )alkyl group, and a halo(C 1 -C 6 )alkoxy group Indicates the group.
- R 3b is (e1) A hydrogen atom; or (e2) (C 1 -C 6 ) alkyl group.
- R 4a is (f1) A hydrogen atom; or (f2) a (C 1 -C 6 ) alkyl group.
- R 4b is (g1) a hydrogen atom; or (g2) a (C 1 -C 6 ) alkyl group.
- R5 is (h1) (C 1 -C 6 ) alkyl group; (h2) (C 2 -C 6 ) alkenyl group; (h3) (C 2 -C 6 ) alkynyl group; (h4) (C 3 -C 6 ) cyclo Alkyl group; (h5) halo (C 1 - C 6 ) alkyl group; (h6) halo (C 2 - C 6 ) alkenyl group; (h7) halo (C 2 - C 6 ) alkynyl group; (h8) halo ( C 3 -C 6 ) cycloalkyl group; (h9) substituted (C 1 -C 6 ) alkyl group having 1 to 3 substituents each independently selected from substituent group A; (h10) substituent group Substituted (C 3 - C 6 ) cycloalkyl group having 1 to 3 substituents on the ring, each independently selected from B; (h11) phenyl group; (h
- R6 is (i1) Hydrogen atom; (i2) (C 1 -C 6 ) alkyl group; (i3) (C 3 -C 6 ) cycloalkyl group; (i4) (C 1 -C 6 ) alkoxy group; or (i5) (C 1 -C 6 ) represents an alkylcarbonyl group.
- X is a hydroxyl group, a (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 )alkylsulfanyl group, a (C 1 -C 6 )alkylsulfinyl group, or a (C 1 -C 6 )alkylsulfonyl group. show.
- Y is an oxygen atom, a sulfur atom, or an NR 7 group (wherein R 7 is a hydrogen atom, a (C 1 -C 6 ) alkyl group, or a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group) , and a halo(C 1 -C 6 )alkyl group, each having 1 to 4 substituents on the ring.
- R 7 is a hydrogen atom, a (C 1 -C 6 ) alkyl group, or a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group) , and a halo(C 1 -C 6 )alkyl group, each having 1 to 4 substituents on the ring.
- Substituent group A is (j1) Cyano group; (j2) (C 1 -C 6 ) alkyl group; (j3) (C 2 -C 6 ) alkenyl group; (j4) (C 2 -C 6 ) alkynyl group; (j5) (C 3 - C6 ) cycloalkyl group; (j6) ( C1 - C6 ) alkoxy group; (j7) ( C1 - C6 ) alkylsulfanyl group; (j8) ( C1 - C6 ) alkylsulfinyl group; (j9) (C 1 -C 6 )alkylsulfonyl group; (j10) Halo (C 1 -C 6 ) alkyl group; (j11) Halo (C 2 -C 6 ) alkenyl group; (j12) Halo (C 2 - C 6 ) alkynyl group; (j13) halo(C 3 -C 6 )cycl
- Substituent group B is (k1) Cyano group; (k2) (C 1 -C 6 ) alkyl group; (k3) (C 2 -C 6 ) alkenyl group; (k4) (C 2 -C 6 ) alkynyl group; (k5) (C 3 - C6 ) cycloalkyl group; (k6) ( C1 - C6 ) alkoxy group; (k7) ( C1 - C6 ) alkylsulfanyl group; (k8) ( C1 - C6 ) alkylsulfinyl group; (k9) (C 1 - C 6 ) alkylsulfonyl group; (k10) halo (C 1 - C 6 ) alkyl group; (k11) halo (C 3 - C 6 ) cycloalkyl group; (k12) halo (C 1 -C 6 ) alkoxy group; (k13) halo(C 1 -C 6
- Substituent group C is (l1) Halogen atom; (l2) Cyano group; (l3) Nitro group; (l4) Hydroxyl group; (l5) Carboxyl group; (l6) (C 1 - C 6 ) alkyl group; (l7) (C 2 - C 6 ) alkenyl group; (l8) (C 2 -C 6 ) alkynyl group; (l9) (C 1 -C 6 ) alkoxy group; (l10) (C 3 -C 6 ) cycloalkyl group; (l11) ( C 1 -C 6 )alkylsulfanyl group; (l12) (C 1 -C 6 )alkylsulfinyl group; (l13) (C 1 -C 6 )alkylsulfonyl group; (l14) halo(C 1 -C 6 )alkyl Group; (l15) Halo (C 2 - C 6 ) alkenyl group; (l16
- Substituent group D is (m1) Halogen atom; (m2) Cyano group; (m3) Nitro group; (m4) Amino group; (m5) Hydroxyl group; (m6) Carboxyl group; (m7) (C 1 - C 6 ) alkyl group; ( m8) (C 2 - C 6 ) alkenyl group; (m9) (C 2 - C 6 ) alkynyl group; (m10) (C 1 - C 6 ) alkoxy group; (m11) (C 3 - C 6 ) cycloalkyl Group; (m12) (C 1 -C 6 )alkylsulfanyl group; (m13) (C 1 -C 6 )alkylsulfinyl group; (m14) (C 1 -C 6 )alkylsulfonyl group; (m15) Halo (C 1 - C 6 ) alkyl group; (m16) halo (C 2 - C 6
- the substituent group E is (n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n4) Amino group; (n5) Hydroxyl group; (n6) Carboxyl group; (n7) (C 1 - C 6 ) alkyl group; ( n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 - C 6 ) cycloalkyl group; (n10) (C 1 - C 6 ) alkylsulfanyl group; (n11) (C 1 - C 6 ) Alkylsulfinyl group; (n12) (C 1 - C 6 ) alkyl sulfonyl group; (n13) halo (C 1 - C 6 ) alkyl group; (n14) halo (C 1 - C 6 ) alkoxy group; (n15) halo (C 3 - C 6 ) cycloalkyl group; (n16) halo (C
- N-(C 1 -C 6 )alkylaminosulfonyl group, or N,N-di(C 1 -C 6 )alkylaminosulfonyl group is not substituted.
- R 1 is (a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 -C 6 )cycloalkyl group; (a6) halo(C 1 -C 6 )alkyl group; (a10) substituted group having 1 to 3 substituents each independently selected from substituent group A (C 1 -C 6 ) alkyl group; (a12) (C 1 -C 6 ) alkoxycarbonyl group; (a14) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 ) alkyl group may be the same or different); (a15) phenylaminocarbonyl group; (a16) phenyl (C 1 -C 6 ) alkyl group; (a17) 1
- Substituent group A is (j1) Cyano group; (j5) (C 3 - C 6 ) cycloalkyl group; (j6) (C 1 - C 6 ) alkoxy group; (j7) (C 1 - C 6 ) alkylsulfanyl group; (j8) (C 1 -C 6 )alkylsulfinyl group; (j9) (C 1 -C 6 )alkylsulfonyl group; and (j18) (C 1 -C 6 )alkoxycarbonyl group
- Substituent group C is (l1) Halogen atom; (l2) Cyano group; (l3) Nitro group; (l6) (C 1 -C 6 ) alkyl group; (l9) (C 1 -C 6 ) alkoxy group; (l11) (C 1 -C 6 ) alkylsulfanyl group; (l12) (C 1 -C 6 ) alkylsulfinyl group
- R 1 is (a1) Hydrogen atom; (a3) (C 2 -C 6 ) alkenyl group; (a6) Halo (C 1 -C 6 ) alkyl group; (a10) 1 to 3 each independently selected from substituent group A (a16) a phenyl (C 1 -C 6 ) alkyl group; (a17) a substituted (C 1 -C 6 ) alkyl group having 1 to 5 substituents, each independently selected from substituent group C; Substituted phenyl (C 1 - C 6 ) alkyl group having a substituent on the ring; (a18) Pyridyl (C 1 -C 6 ) alkyl group; (a44) Phenyl group; (a45) Each independently from substituent group D Substituted phenyl group having 1 to 5 selected substituents on the ring; (a46) Pyridyl group; (a47) 1 to 4 substituents independently selected from substituent group D on the
- the substituent group E is (n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n7) (C 1 - C 6 ) alkyl group; (n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 -C 6 ) cycloalkyl group; (n10) (C 1 -C 6 ) alkylsulfanyl group; (n12) (C 1 -C 6 ) alkylsulfonyl group; (n13) halo(C 1 -C 6 ) alkyl group; (n14) Halo(C 1 -C 6 )alkoxy group; (n19) (C 1 -C 6 )alkylcarbonylamino group; (n21) (C 1 -C 6 )alkylsulfonylamino group; (n33) Adjacent A methylenedioxy group
- a pest control agent characterized by containing the compound described in any one of [1] to [3] or a salt thereof as an active ingredient
- a pest control agent for agricultural and horticultural purposes characterized by containing the compound or its salts described in any one of [1] to [3] as an active ingredient
- An animal ectoparasite control agent characterized by containing the compound or salt thereof as an active ingredient according to any one of [1] to [3]
- An animal endoparasite control agent characterized by containing the compound or salt thereof as an active ingredient according to any one of [1] to [3]
- a method for controlling agricultural and horticultural pests which comprises applying an effective amount of the agricultural and horticultural pest control agent according to [5] to plants or soil
- a method for controlling animal ectoparasites which comprises orally or parenterally administering an effective amount of the animal ectoparasiticide according to [6] to a target animal; [10]
- the compound or salt thereof of the present invention provides an azepanedione derivative represented by the general formula (1), which has excellent effects as a pest control agent.
- halo means a "halogen atom” and represents a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom.
- (C 1 -C 6 )alkyl group means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group.
- (C 2 -C 6 )alkenyl group means, for example, vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2 - Straight chain or branched alkenyl group having 2 to 6 carbon atoms such as propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, etc.
- (C 2 -C 6 )alkynyl group refers to, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl- Straight chain or branched chain such as 1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,3-dimethyl-1-butynyl group Indicates an alkynyl group having 2 to 6 carbon atoms.
- (C 3 -C 6 )cycloalkyl group refers to a cyclic alkyl group having 3 to 6 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
- (C 1 -C 6 )alkoxy group means, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyl group.
- (C 1 -C 6 )alkylsulfanyl group means, for example, a methylsulfanyl group, an ethylsulfanyl group, a normal propylsulfanyl group, an isopropylsulfanyl group, a normal butylsulfanyl group, a secondary butylsulfanyl group, a tertiary butylsulfanyl group, Normal pentylsulfanyl group, isopentylsulfanyl group, tertiary pentylsulfanyl group, neopentylsulfanyl group, 2,3-dimethylpropylsulfanyl group, 1-ethylpropylsulfanyl group, 1-methylbutylsulfanyl group, normal hexylsulfanyl group, iso Indicates a linear or branched alkylsulfanyl group having 1 to 6 carbon —
- (C 1 -C 6 )alkylsulfinyl group means, for example, a methylsulfinyl group, an ethylsulfinyl group, a normal propylsulfinyl group, an isopropylsulfinyl group, a normal butylsulfinyl group, a secondary butylsulfinyl group, a tertiary butylsulfinyl group, Normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, iso It represents a linear or branched
- (C 1 -C 6 )alkylsulfonyl group means, for example, a methylsulfonyl group, an ethylsulfonyl group, a normal propylsulfonyl group, an isopropylsulfonyl group, a normal butylsulfonyl group, a secondary butylsulfonyl group, a tertiary butylsulfonyl group, Normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, iso Indicates a linear or branched
- (C 1 -C 6 )alkylcarbonyl group includes, for example, acetyl group, propanoyl group, butanoyl group, 2-methylpropanoyl group, pentanoyl group, 2-methylbutanoyl group, 3-methylbutanoyl group, It refers to an alkylcarbonyl group having 2 to 7 carbon atoms, such as an alkylcarbonyl group having the above-mentioned (C 1 -C 6 ) alkyl group such as a pivaloyl group or a hexanoyl group.
- (C 1 -C 6 )alkylcarbonylamino group means, for example, acetylamino group, propanoylamino group, butanoylamino group, 2-methylpropanoylamino group, pentanoylamino group, 2-methylbutanoyl
- An alkylcarbonylamino group having 2 to 7 carbon atoms such as an alkylcarbonylamino group having the above-mentioned (C 1 -C 6 ) alkyl group such as an amino group, 3-methylbutanoylamino group, pivaloylamino group, hexanoylamino group, etc. shows.
- (C 1 -C 6 )alkylsulfonylamino group means, for example, methylsulfonylamino group, ethylsulfonylamino group, normal propylsulfonylamino group, isopropylsulfonylamino group, normal butylsulfonylamino group, secondary butylsulfonylamino group , tertiary butylsulfonylamino group, normal pentylsulfonylamino group, isopentylsulfonylamino group, tertiary pentylsulfonylamino group, neopentylsulfonylamino group, 2,3-dimethylpropylsulfonylamino group, 1-ethylpropylsulfonylamino group , 1-methylbutylsulfonylamino group, n-hex
- N-(C 1 -C 6 )alkylaminocarbonyl group means, for example, N-methyl-aminocarbonyl group, N-ethylaminocarbonyl group, N-normalpropylaminocarbonyl group, N-isopropylaminocarbonyl group, -Normal butylaminocarbonyl group, N-isobutylaminocarbonyl group, N-secondary butylaminocarbonyl group, N-tertiary butylaminocarbonyl group, N-normalpentylaminocarbonyl group, N-isopentylaminocarbonyl group, N-tertiary Contains a linear or branched alkyl group having 1 to 6 carbon atoms, such as a liepentylaminocarbonyl group, N-neopentylaminocarbonyl group, N-normalhexylaminocarbonyl group, and N-isohexylaminocarbonyl group. It
- (C 1 -C 6 )alkoxycarbonyl group means, for example, methoxycarbonyl group, ethoxycarbonyl group, normal propoxycarbonyl group, isopropoxycarbonyl group, normal butoxycarbonyl group, isobutoxycarbonyl group, secondary butoxycarbonyl group, It refers to an alkoxycarbonyl group having 2 to 7 carbon atoms, such as an alkoxycarbonyl group having the above-mentioned (C 1 -C 6 ) alkoxy group, such as a tert-butoxycarbonyl group or a pentyloxycarbonyl group.
- N-(C 1 -C 6 )alkylaminosulfonyl group means, for example, N-methylaminosulfonyl group, N-ethylaminosulfonyl group, N-normalpropylaminosulfonyl group, N-isopropylaminosulfonyl group, N-isopropylaminosulfonyl group, -Normal butylaminosulfonyl group, N-Secondary butylaminosulfonyl group, N-Tertiary butylaminosulfonyl group, N-Normalpentylaminosulfonyl group, N-Isopentylaminosulfonyl group, N-Tertiary pentylaminosulfonyl group, N -Neopentylaminosulfonyl group, N-(2,3-dimethylpropyl)aminosulfonyl group, N-(1
- N,N-di(C 1 -C 6 )alkylaminosulfonyl group means, for example, N,N-dimethylaminosulfonyl group, N,N-diethylaminosulfonyl group, N,N-dinormalpropylaminosulfonyl group.
- N,N-diisopropylaminosulfonyl group N,N-di-n-butylaminosulfonyl group, N,N-dise-butylaminosulfonyl group, N,N-ditertiarybutylaminosulfonyl group, N-methyl-N-ethyl Aminosulfonyl group, N-methyl-N-normalpropylaminosulfonyl group, N-methyl-N-isopropylaminosulfonyl group, N-methyl-N-normalbutylaminosulfonyl group, N-methyl-N-secondary butylaminosulfonyl group , N-methyl-N-tert-butylaminosulfonyl group, N-methyl-N-normalpentylaminosulfonyl group, N-methyl-N-isopentylaminosulfonyl group, N-methyl-N-tert-pent
- Halo(C 1 -C 6 )alkyl group "Halo(C 2 -C 6 )alkenyl group”, “Halo(C 2 -C 6 )alkynyl group”, “Halo(C 1 -C 6 ) alkyl group”, respectively.
- alkoxy group "halo(C 1 -C 6 )alkylsulfanyl group”, “halo(C 1 -C 6 )alkylsulfinyl group”, “halo(C 1 -C 6 )alkylsulfonyl group”, “halo(C 6 )alkylsulfonyl group” 3 -C 6 )cycloalkyl group", "Halo(C 1 -C 6 )alkylcarbonylamino group”, “Halo(C 1 -C 6 )alkylsulfonylamino group", “N-halo(C 1 -C 6 ) )alkylaminocarbonyl group”, “halo(C 1 -C 6 )alkoxycarbonyl group”, etc.
- Examples of the salts of the compound represented by the general formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, acetate, fumarate, maleate, oxalate, Examples include organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium.
- inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, acetate, fumarate, maleate, oxalate
- examples include organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate
- salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and
- the compound represented by the general formula (1) of the present invention and its salts may have one or more asymmetric centers in its structural formula, and may have two or more optical isomers and diastereomers. In some cases, optical isomers exist, and the present invention includes all optical isomers and mixtures containing them in arbitrary proportions.
- the compound represented by the general formula (1) of the present invention and its salts may have two types of geometric isomers derived from a carbon-carbon double bond in the structural formula, but the present invention It also includes all geometric isomers and mixtures containing them in arbitrary proportions.
- the compound represented by the general formula (1) of the present invention and its salts may have a plurality of tautomers, but the present invention covers each tautomer and their arbitrary proportions. It also includes all mixtures contained in the above.
- R 1 is the above (a1), (a2), (a3), (a4), (a5), (a6), (a10), (a12), (a14), (a15), (a16), (a17), (a18), (a19), (a24), (a25), (a26), (a27), (a36), (a37), (a40), (a41 ), (a44), (a45), (a46), (a47), (a50), (a51), (a52), (a53), (a54), (a55), (a60), (a61), The groups (a64), (a65), (a66), (a67), (a68), (a69), (a72), or (a73) are preferred, and the above (a1), (a3), (a6) , (a10), (a16), (a17), (a18), (a44), (a45), (a46), (a47), (a
- R 2a is preferably the above-mentioned (b1) hydrogen atom.
- R 2b is preferably the above-mentioned (c1) hydrogen atom.
- R 3a is preferably the group (d1), (d2), (d3), or (d4) above, and more preferably the group (d1) or (d2) above.
- R 3b is preferably the group (e1) or (e2) above.
- R 4a is preferably the above group (f1) or (f2), and more preferably the above group (f1).
- R 4b is preferably the group (g1) or (g2) above, and more preferably the group (g1) above.
- R 5 includes the above (h1), (h3), (h4), (h5), (h11), (h12), (h13), (h14), (h15), (h16), (h17), (h18), (h19), (h20), (h25), (h26), (h27), (h28), (h31), (h32), (h41), (h42 ), (h53), or (h54) groups are preferred, and the above groups (h1), (h11), (h12), (h13), (h14), (h15), (h16), (h18), ( h19), (h25), (h28), (h31), (h42), or (h53) are more preferred.
- X is a hydroxyl group, a (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 ) alkylsulfanyl group, a (C 1 -C 6 )alkylsulfinyl group, or a (C 1 -C 6 )alkylsulfinyl group.
- -C 6 )Alkylsulfonyl group is preferred, and hydroxyl group is more preferred.
- substituent group B includes the above (k1), (k2), (k3), (k4), (k5), (k6), (k7), (k8), (k9). ), (k10), (k11), (k12), (k13), (k14), (k15), and (k16).
- the substituent group C includes the above (l1), (l2), (l3), (l6), (l9), (l11), (l12), (l13), (l14 ), (l17), (l19), (l20), (l21), (l23), (l24), (l25), (l26), (l27), (l28), (l29), and (l30) It is preferably composed of the groups (l1), (l2), (l9), (l11), (l14), (l17), (l19), and (l20) described above. .
- Manufacturing method 1 The compound represented by the general formula (1-1) of the present invention can be produced from the compound represented by the general formula (2) by the following step [a].
- R 1 , R 2a , R 2b , R 3a , R 3b , R 4a , R 4b , R 5 and Y are the same as above. ⁇
- step [a] By reacting the compound represented by general formula (2) with the compound represented by general formula (3) in the presence of a base and an inert solvent, the general formula (1 A compound represented by -1) can be produced.
- bases examples include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide.
- alkoxides such as side, alkali metal hydrides such as sodium hydride, potassium hydride, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate, cesium carbonate, etc.
- organic bases such as (DBU), and the amount used is usually in the range of 1 to 10 times the mole of the compound represented by the general formula (2).
- Inert solvents that can be used in this reaction may be those that do not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
- Aromatic hydrocarbons such as chlorobenzene and dichlorobenzene
- inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran
- acetonitrile propionitrile Nitriles such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide
- aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone, methanol, ethanol, propanol, butanol, 2
- examples include alcohols such as -propanol, and these inert solvents can be used alone or in combination of two or more.
- the amount used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (2).
- 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., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate.
- 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.
- Manufacturing method 2 The compound represented by general formula (1-2) of the present invention can be produced from the compound represented by general formula (2) by the following step [b].
- R 1 , R 2a , R 2b , R 3a , R 3b , R 4a , R 4b , R 5 , R 6 and Y are the same as above.
- L represents, for example, a halogen atom such as chlorine or bromine, or a leaving group such as an imidazolyl group or a trichloromethoxy group.
- Examples include carbonates, acetates such as lithium acetate, sodium acetate, and potassium acetate, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, N,N-diisopropylethylamine, and DBU. It is usually used in an amount of 1 to 10 times the mole of the compound represented by general formula (2).
- Inert solvents that can be used in this reaction may be those that do not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc.
- Aromatic hydrocarbons such as chlorobenzene and dichlorobenzene
- inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran
- acetonitrile propionitrile Nitriles such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide
- aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone, methanol, ethanol, propanol, butanol, 2
- examples include alcohols such as -propanol, and these inert solvents can be used alone or in combination of two or more.
- the amount used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (2).
- 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., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate.
- 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.
- the compound represented by general formula (2) which is the starting material for the compounds represented by general formulas (1-1) and (1-2) of the present invention, is prepared from Tetrahedron Letters, 1995, 36, 3659 or Journal of Heterocyclic Chemistry, 2017, 54, 1318, or according to the method described therein.
- Pest control agents containing the compound represented by general formula (1) or its salts as an active ingredient of the present invention include agricultural and horticultural pest control agents, ectoparasite control agents for animals, and endoparasite control agents for animals. Can be applied as As an agricultural and horticultural pest control agent, it can be applied to control various agricultural and forestry, horticultural, grain storage pests, sanitary pests, nematodes, and other pests that damage paddy rice, fruit trees, vegetables, other crops, and flowers.
- agricultural and horticultural insecticides containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention have physical properties suitable for various labor-saving application methods, systemic transfer activity, and suitable soil Excellent environmental safety such as persistence.
- the agricultural and horticultural insecticides containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention have no effect on natural enemies, useful insects such as the European honey bee and bumble bee, and environmental organisms such as midges. Less is.
- Lepidoptera lepidoptera
- Lepidoptera include Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, Spodoptera exempta, and American white flycatcher.
- Adoxophyes orana) Caloptilia theivora, Homona magnanima, Ephestia elutella, Eumeta minuscula, Clostera anachoreta, Heliothis maritima, Sparganothis pilleriana, Busseola fusca, Euproctis subflava, Biston robustum, Heliothis zea, Aedia leucomelas, Narosoideus flavidorsalis, Viminia rumicis, Biston robustum Bucculatrix pyrivorella), Grapholita molesta, Spulerina astaurota, Ectomyelois pyrivorella, Chilo suppressalis, Acrolepiopsis sapporensis, Plodia interpunctella, Hellula undalis ), Sitotroga cerealella, Spodoptera litura, Eucosma aporema, Acleris comariana, Scopelodes contractus, Orgyia
- Hemipteran pests include Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, etc.
- Aeschynteles maculatus Creontiades pallidifer, Dysdercus cingulatus, Chrysomphalus ficus, Aonidiella aurantii, Graptopsaltria nigrofuscata, Blissus leucopter us), Iseriya Icerya purchasi, Piezodorus hybneri, Lagynotomus elongatus, Thaia subrufa, Scotinophara lurida, Sitobion ibarae, Stariodes iwasaki i) , Aspidiotus destructor, Taylorilygus pallidulus, Myzusmumecola, Pseudaulacaspis prunicola, Acyrthosiphon pisum, Ana
- Cavelerius saccharivorus Galeatus spinifrons, Macrosiphoniella sanborni, Aonidiella citrina, Halyomorpha mista, Stephanitis fasciicarina, Trioza camphorae , spider Leptocorisa chinensis, Trioza quercicola, Uhlerites latius, Grapeleaf hopper (Erythroneura comes), Paromius exiguus, Duplaspidiotus claviger, Nephotettix nigropictus, Halticiellus insularis, Perkinsiella saccharicida, Psylla malivorella, Anomomeura mori, Pseudococcus longispinis, Pseudaulacaspi s pentagona ), Pulvinaria kuwacola, Apolygus lucorum, Togo hempterus, Toxoptera aurantii, Saccharicoccus sacchari, Geoica lucifuga
- pests of the order Coleoptera include Xystrocera globosa, Paederus fuscipes, Eucetonia roelofsi, Callosobruchus chinensis, Cylas formicarius, and alfalfa weevil.
- Diptera pests include Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, and Chlorops oryzae.
- Hymenoptera (Hymenoptera) pests include, for example, Pristomyrmex ponnes, wasps, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Dryocosmus kuriphilus, and Formica fusca japonica. , Wasps, Athalia infumata infumata, Arge pagana, Athalia japonica, Acromyrmex spp., fire ant (Solenopsis spp.), Arge mali (Ochetellus glaber) etc.
- thrips pests include Selenothrips rubrocinctus, Stenchaetothrips biformis, Haplothrips aculeatus, Ponticulothrips diospyrosi, Thrips flavus, and Thrips flavus.
- Thrips (Anaphothrips obscurus) , Cusukuda thrips (Liothrips floridensis), Gladiolus thrips (Thrips simplex), Black thrips (Thrips nigropilosus), Croton thrips (Heliothrips haemorrhoidalis), Swamp thrips (Pseudodendrothrips mori), Cosmos thrips (Microcephalothrips Abdominalis) , Thrips ( Leeuwenia pasanii), Litotetothrips pasaniae, Scirtothrips citri, Haplothrips chinensis, Mycterothrips glycines, Thrips setosus, Tea thrips (Mycterothrips glycines) Scirtothrips dorsalis ), Choco Clothy Samewomes (DendrothRips Minowai), Haplo
- Examples of insect pests in the order of Acari include Leptotrombidium akamushi, Tetranychus ludeni, Dermacentor variabilis, Tetranychus truncatus, Ornithonyssus bacoti, Demodex canis, and Demodex canis.
- Ticks such as Tetranychus viennensis, Tetranychus kanzawai, and Rhipicephalus sanguineus, Cheyletus malaccensis, Tyrophagus putrescentiae, Dermatophagoides farinae, and Latrodectus ha.
- termite pests include Reticulitermes miyatakei, Incisitermes minor, Coptotermes formosanus, Hodotermopsis japonica, Reticulitermes sp., and Reticulitermes flaviceps amamianus. , Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus, Odon totermes formosanus) , Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes speratus.
- Examples of pests of the order Cockroaches include the black cockroach (Periplaneta fuliginosa), the German cockroach (Blattella germanica), the Japanese cockroach (Blatta orientalis), the brown cockroach (Periplaneta brunnea), the Japanese cockroach (Blattella lituricollis), the Japanese cockroach (Periplaneta japonica), and the American cockroach. (Periplaneta americana) etc.
- nematodes examples include the strawberry nematode (Nothotylenchus acris), the rice nematode (Aphelenchoides besseyi), the northern nematode (Pratylenchus penetrans), the northern nematode (Meloidogyne hapla), the sweet potato nematode (Meloidogyne incognita), and the potato cyst nematode (Globodera).
- rostochiensis Javan cat nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), southern coffeae (Pratylenchus coffeae), barley coffeae (Pratylenchus neglectus), and citrus nematode (Tylenchus semipenetrans).
- molluscs examples include Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Lehmannina valentiana, Limax flavus, and Acusta despecta sieboldiana. can be mentioned.
- the agricultural and horticultural pest control agent of the present invention has a strong insecticidal effect against other pests such as tomato absolutea (Tuta absoluta).
- the agricultural and horticultural pest control agent containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention is suitable for use in agricultural and horticultural pest control agents that cause damage to paddy crops, field crops, fruit trees, vegetables, other crops, flowers, etc. Because it has a remarkable control effect against pests, it is necessary to remove seedlings, paddy fields, fields, fruit trees, vegetables, and other crops before the outbreak of pests or when the outbreak of pests is confirmed.
- the intended effects of the agricultural and horticultural pest control agent of the present invention can be achieved by treating it on cultivation carriers such as seeds of flowers, paddy water, stems and leaves, or soil.
- the compound of the present invention can be absorbed through the roots through or without the soil by treating the soil for raising seedlings of crops, flowers, etc., the soil for planting holes during transplanting, the roots of plants, irrigation water, cultivation water for hydroponic cultivation, etc.
- a preferred form of use is application that takes advantage of the so-called permeation and migration properties.
- Useful plants to which the agricultural and horticultural pest control agent of the present invention can be used are not particularly limited, but include, for example, cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), legumes (soybean, etc.) , adzuki beans, fava beans, peas, kidney beans, peanuts, etc.), fruit trees/fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves/fruit vegetables (cabbage) , tomatoes, spinach, broccoli, lettuce, onions, green onions (morning onions, spring onions), green peppers, eggplants, strawberries, peppers, okra, chives, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, radish, turnips, lotus root, etc.), processed crops (cotton, hemp, bee
- plants include HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthetase inhibitors such as glufosinate, and setoxydim. Also included are plants that have been made resistant to herbicides such as acetyl-CoA carboxylase inhibitors, bromoxynil, dicamba, and 2,4-D by classical breeding methods or genetic recombination techniques.
- HPPD inhibitors such as isoxaflutole
- ALS inhibitors such as imazethapyr and thifensulfuron-methyl
- EPSP synthase inhibitors such as glyphosate
- glutamine synthetase inhibitors such as glufosinate
- setoxydim setoxydim.
- plants that have been made resistant to herbicides such as acetyl-CoA carboxylase inhibitors,
- plants that have been made resistant through classical breeding methods include rapeseed, wheat, sunflower, and rice, which are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazethapyr, which is available under the trade name Clearfield (registered trademark). is already on sale.
- rapeseed, wheat, sunflower, and rice which are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazethapyr, which is available under the trade name Clearfield (registered trademark). is already on sale.
- sulfonylurea-based ALS-inhibiting herbicides such as thifensulfuron-methyl produced by classical breeding methods, and it is already sold under the trade name STS soybean.
- SR corn is an example of a plant that has been made resistant to acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides through classical breeding methods.
- acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides through classical breeding methods.
- plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors are listed in the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA) Vol. 87, pp. 7175-7179 (1990).
- mutant acetyl-CoA carboxylase that is resistant to acetyl-CoA carboxylase inhibitors has been reported in Weed Science, Vol.
- Plants resistant to acetyl-CoA carboxylase inhibitors can be created by introducing them into plants or by introducing mutations that confer resistance into plant acetyl-CoA carboxylase inhibitors.Furthermore, chimeraplasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.) is introduced into plant cells to introduce site-specific amino acids into plant acetyl-CoA carboxylase genes, ALS genes, etc. By introducing substitution mutations, it is possible to create plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, etc., and the agricultural and horticultural pest control agent of the present invention can also be used for these plants. can.
- insecticidal proteins derived from Bacillus cereus and Bacillus popilliae such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis; Insecticidal proteins such as endotoxin, VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, and papain inhibitors; ribosome inactivating proteins (RIPs) such as ricin, corn-RIP, abrin, ruffin, saporin, and
- RIPs ribosome inactivating proteins
- toxins expressed in such genetically modified plants include ⁇ -endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, VIP1, VIP2, VIP3, or VIP3A, etc.
- Hybrid toxins, partially deleted toxins, and modified toxins of insecticidal proteins are also included. Hybrid toxins are created by new combinations of different domains of these proteins using recombinant technology.
- Cry1Ab which has a partially deleted amino acid sequence, is known as a partially deleted toxin.
- a modified toxin has one or more amino acids substituted for the naturally occurring toxin.
- the toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera, Diptera, Lepidoptera, and nematodes.
- the agricultural and horticultural pest control agent of the present invention can be used in combination with or systematized with those techniques.
- the agricultural and horticultural pest control agent of the present invention is used as it is, or diluted or suspended with water etc. in an effective amount to control various pests and nematodes. It can be used on plants where outbreaks are predicted. For example, for pests and nematodes that occur in fruit trees, grains, vegetables, etc., in addition to spraying on the stems and leaves, soaking seeds in chemicals, seed dressing, and cultivating methods can be used. Treatments such as seed treatment, soil full layer mixing, cropping application, bed soil mixing, cell seedling treatment, planting hole treatment, plant base treatment, top dressing, rice box treatment, water surface application, etc. It can also be absorbed and used.
- the agricultural and horticultural pest control agent of the present invention can be used as it is, diluted with water, etc., or suspended in an effective amount for pest control in a place where the pests are expected to occur.
- the agricultural and horticultural pest control agent of the present invention can be used as it is, diluted with water, etc., or suspended in an effective amount for pest control in a place where the pests are expected to occur.
- it in addition to spraying on grain storage pests, house pests, sanitary pests, forest pests, etc., it can also be used as a coating on house building materials, smoke, bait, etc.
- Seed treatment methods include, for example, diluting a liquid or solid preparation or immersing the seeds in an undiluted liquid state to infiltrate the seeds, mixing a solid or liquid preparation with the seeds, or coating the seeds with powder. Examples include a method of treating and adhering to the surface of seeds, a method of mixing with an adhesive carrier such as a resin or polymer and coating the seeds, and a method of spraying near the seeds at the same time as planting.
- seed used for the seed treatment refers to plants in the early stage of cultivation used for plant propagation, such as seeds, bulbs, tubers, seed potatoes, shoots, bulbs, scales, or cuttings for cultivation. Examples include plants for vegetative propagation.
- soil or “cultivation carrier” for plants when carrying out the method of use of the present invention refers to a support for cultivating crops, especially a support for growing roots, and the material is not particularly limited. However, any material that plants can grow on may be used, such as soil, seedling mats, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, and high-quality materials. It may also be a molecular substance, rock wool, glass wool, wood chips, bark, etc.
- liquid preparations such as emulsions and flowables, or solid preparations such as wettable powders or granule wettable powders, are diluted with water as appropriate.
- a method of spraying a method of spraying a powder, a method of smoking, etc.
- Methods for applying to soil include, for example, applying liquid preparations to the base of plants or seedling beds without diluting them with water, or applying granules to the base of plants or seedling beds for raising seedlings.
- Methods of spraying on seedbeds, etc. methods of spraying powders, wettable powders, granule wettable powders, granules, etc. before sowing or transplanting and mixing them with the entire soil, methods of spraying in planting holes, etc. before sowing or transplanting plants, etc. Examples include methods of dispersing powders, wettable powders, hydrated granules, granules, etc. in strips.
- the dosage form may vary depending on the time of application, such as application at sowing, application during greening, application at transplanting, etc. It can be applied in a mold. It can also be applied by mixing with the soil, and it can be mixed with the soil and a powder, a granular wettable powder, a granule, etc., such as mixing with bed soil, mixing with soil covering, and mixing with the entire soil. You may simply apply the soil and various preparations in alternating layers.
- solid preparations such as jumbo preparations, pack preparations, granules, and wettable powders
- liquid preparations such as flowables and emulsions
- a suitable formulation can be sprayed or injected into the soil as it is or mixed with fertilizer.
- a chemical solution such as an emulsion or a flowable at a source where water flows into a rice field, such as a water outlet or an irrigation system, it can be applied in a labor-saving manner as water is supplied.
- seeds or cultivation carriers close to the plants can be treated during the seeding to seedling-raising period.
- treatment to the roots of plants under cultivation is suitable.
- Spraying treatment can be performed using granules, or irrigation treatment can be carried out in liquid form by diluting or not diluting the agent with water. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow the seeds.
- Treatments during the sowing and seedling-raising stages of cultivated plants to be transplanted include direct treatment of seeds, as well as irrigation treatment with liquid chemicals or spraying treatment with granules on seedling beds.
- the agricultural and horticultural pest control agent of the present invention is generally formulated into a form convenient for use according to conventional methods for pesticide formulations. That is, the compound represented by the general formula (1) of the present invention or its salts can be dissolved, separated, or suspended by blending them in an appropriate inert carrier or with an adjuvant as necessary in an appropriate ratio. It can be used by clouding, mixing, impregnating, adsorbing or adhering it into an appropriate dosage form, such as suspension, emulsion, liquid, wettable powder, wettable powder, granule, powder, tablet, pack, etc. Good.
- the agricultural and horticultural pest control agent of the present invention may contain additive components commonly used in agricultural chemical formulations, if necessary.
- additive components include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, spreading agents, and antifreeze agents. , anti-caking agents, disintegrants, anti-decomposition agents and the like.
- Other additives such as preservatives and plant pieces may be used as necessary.
- These additive components may be used alone or in combination of two or more.
- solid carriers examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. , synthetic silicic acid, synthetic silicates, starch, cellulose, organic solid carriers such as vegetable powders (e.g. sawdust, coconut shell, corncob, tobacco stalk, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea, Examples include inorganic hollow bodies, plastic hollow bodies, fumed silica (white carbon), etc. These may be used alone or in combination of two or more.
- natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomace
- liquid carriers examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
- alcohols, polyhydric alcohol compounds such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, THF, etc.
- ethers normal paraffin, naphthene, isoparaffin, kerosene, aliphatic hydrocarbons such as mineral oil, aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, dichloromethane, chloroform, carbon tetrachloride, etc.
- surfactants used as dispersants and wetting agents include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, Polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzylphenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxy Alkylene-a
- binders and tackifiers include carboxymethylcellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and average molecular weight of 6,000 to 20,000.
- (meth)acrylic acid copolymers half esters of polyhydric alcohol polymers and dicarboxylic anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffins, terpenes, polyamide resins, polyacrylates, polyoxy Examples include ethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, and synthetic resin emulsion.
- thickeners examples include water-soluble polymers such as xanthan gum, guar gum, diurtan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, polysaccharides, high-purity bentonite, and fumed silica.
- Inorganic fine powders such as silica, white carbon, etc.
- coloring agent examples include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.
- antifreeze agents examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
- adjuvants to prevent caking and promote disintegration include starch, alginic acid, polysaccharides such as mannose and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylic acid ester copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene/isobutylene/maleic anhydride copolymer, starch/polyacrylonitrile graft copolymer Examples include polymers.
- decomposition inhibitors include drying agents such as zeolite, quicklime, and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds, and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It will be done.
- preservatives examples include potassium sorbate and 1,2-benzothiazolin-3-one.
- other aids such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreeze agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers, etc. Agents can also be used.
- the blending ratio of the active ingredient compound can be adjusted as necessary, and it may be used by appropriately selecting from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural pest control agent of the present invention.
- the appropriate amount is 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural pest control agent).
- the amount of the agricultural and horticultural pest control agent of the present invention to be used depends on various factors, such as purpose, target pests, crop growth conditions, pest outbreak trends, weather, environmental conditions, dosage form, application method, application location, application timing, etc. Depending on the purpose, the amount of the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, per 10 ares.
- the agricultural and horticultural pest control agent of the present invention can be used in combination with other agricultural and horticultural insecticides, acaricides, nematicides, and fungicides for the purpose of expanding the pests to be controlled and the appropriate period for control, or reducing the amount of pesticides. , biological pesticides, etc., and can also be used in combination with herbicides, plant growth regulators, fertilizers, etc. depending on the usage situation.
- XMC 3,5-xylyl methylcarbamate
- BPMC fenobucarb
- Bt toxin insecticidal compounds CPCBS (chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1,3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), O-ethyl O -4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, acynonapyr, azinphos-methyl, acequinocyl, acetamiprid, Acetoprole, acephate, abamectin,
- Examples of agricultural and horticultural fungicides used for similar purposes include aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, and acibenzolar-S-methyl. ), azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isotianil isotianil, isovaledione, isopyrazam, isofetamid, isoflucypram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin ), iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-albesilate, iminoctadine-triacetate ), imibenconazole, inpyrfluxam, uniconazole,
- Inorganic disinfectants sodium hypochlorote, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate copper-based compounds such as sodium hydrogen carbonate, inorganic sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, and oxine copper. , zinc sulfate, copper sulfate pentahydrate, and the like.
- herbicides such as 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2, 4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, icafolin, icafolin-methyl, aclonifen, azafenidin, acifluorfen, aziprotrine, azimus azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone ( amicarbazone), amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridi
- biopesticides include, for example, nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and entomopoxi virus (EPV). ), insecticides or nematicides such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans, etc.
- a microbial pesticide used as a fungicide for Trichoderma lignorum, Agrobacterium radiobacter, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc.
- a similar effect can be expected by mixing the microbial pesticides used in this invention with biological pesticides used as herbicides such as Xanthomonas campestris.
- biopesticides such as Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus natural enemy organisms such as Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z)-10-tetradecenyl acetate, (E,Z )-4,10-tetradecadinyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-icocen-10-one, 14-methyl-1 - It is also possible to use it in combination with a pheromone agent such as octadecene.
- a pheromone agent such as octadecene.
- the compound represented by general formula (1) of the present invention or a salt thereof is also suitable for controlling parasites in animals.
- Animal parasites live in or on the host animal's body and cause a disadvantage to the host animal.
- the compound represented by the general formula (1) of the present invention or a salt thereof can also be applied as an animal ectoparasiticide or an animal endoparasite controller.
- examples of applicable animals include pigs, horses, Livestock such as cows, sheep, goats, rabbits, camels, water buffalo, deer, mink, and chinchillas, pet animals such as dogs, cats, small birds, and monkeys, laboratory animals such as rats, mice, golden hamsters, and guinea pigs, chickens, ducks, Examples include, but are not limited to, poultry such as ducks, quail, ducks, geese, and turkeys, and humans. It can also be applied to farmed fish such as sea bream, flounder, tuna, yellowtail, and eel, as well as crustaceans and shellfish such as shrimp, crab, scallops, oysters, clams, and clams.
- farmed fish such as sea bream, flounder, tuna, yellowtail, and eel, as well as crustaceans and shellfish such as shrimp, crab, scallops, oysters, clams, and clams.
- order Phthiraptera e.g. Bovicola Ovis, Bovicola Bovis
- the order Lepidoptera e.g. Bovicola Ovis, Bovicola Bovis
- the order Lepidoptera e.g. Bovicola Ovis, Bovicola Bovis
- the order Lepidoptera e.g. Bovicola Ovis, Bovicola Bovis
- the order Lepidoptera e.g. Bovicola Ovis, Bovicola Bovis
- mites include Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis campanulata, and Haemaphysalis concinna.
- fleas examples include Pulicidae and Ceratephyllus.
- fleas belonging to the human flea family include dog flea (Ctenocephalidescanis), cat flea (Ctenocephalides felis), human flea (Pulex irritans), chicken flea (Echidnophaga gallinacea), Cheops rat flea (Xenopsylla cheopis), and blind rat flea (Leptopsylla segnis), the European rat flea (Nosopsyllus fasciatus), and the mountain rat flea (Monopsyllus anisus).
- lice such as cow lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), cow lice (Linognathus vituli), pig lice (Haematopinus suis), pubic lice (Phthirus pubis), and head lice (Pediculus capitis),
- lice such as Trichodectes canis, blood-sucking Diptera pests such as Tabanus trigonus, Culicoides schultzei, and Simulium ornatum can also be treated with the animal ectoparasit control method of the present invention. It is listed as an ectoparasite that can be controlled by anti-inflammatory agents.
- the animal ectoparasiticide of the present invention can be prepared by using a suitable solid or liquid carrier in accordance with a commonly used pharmaceutical formulation, blending the agent in an appropriate proportion with an auxiliary agent as necessary, and dissolving, suspending, They may be mixed, impregnated, adsorbed or adhered, and prepared into a suitable dosage form, such as a liquid, emulsifier, cream, ointment, suspension, or aerosol, depending on the purpose of use.
- the amount of the active ingredient in these preparations can range from 0.01 to 80.0 parts by weight per 100 parts by weight of the preparation.
- the solid carrier or liquid carrier used carriers commonly used for veterinary drugs may be used, and liquid carriers are preferably used because they are easier to treat on target animals.
- liquid carrier examples include alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, tertiary butyl alcohol, and benzyl alcohol, propylene carbonate, N-methyl-2-pyrrolidone, and water.
- alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, tertiary butyl alcohol, and benzyl alcohol, propylene carbonate, N-methyl-2-pyrrolidone, and water.
- Auxiliary agents can be used as necessary, and surfactants, antioxidants, emulsifiers, etc.
- adjuvants such as polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monolaurate, Surfactants such as alkylaryl sorbitan monolaurate, alkylbenzene sulfonate, alkylnaphthalene sulfonic acid, lignosulfonate higher alcohol sulfate ester salt, glycol monoalkyl ether, glycols, sorbitan monooleate, sorbitan monolaurate, caprylic acid Examples include emulsifiers such as monoglyceride, capric acid monoglyceride, isostearic acid monoglyceride, and propylene glycol monocaprylate, and antioxidants such as BHA and BHT.
- surfactants such as alkylaryl sorbitan monolaurate, alkylbenzene sulfonate, alkylnaphthalene sulfonic acid, lignosulfonate higher alcohol sulfate ester salt, glycol
- the animal ectoparasiticide of the present invention may be administered to animals by a route that has the desired effect, such as locally, orally, parenterally, or subcutaneously, and is not particularly limited, but local administration is preferred.
- spot-on treatment involves dropping a liquid drug onto the skin of the dorsal region of the target animal, pour-on treatment, which involves applying a liquid drug along the back line of the target animal, and administering a liquid aerosol drug using a spray method. It can be administered by a treatment method using a spray-on, spray lace, medicinal bath (dip), ear tag or collar carrying a medicinal agent, or the like.
- the application amount may be appropriately selected from the range of usually about 0.1 to 500 mg of the active ingredient compound and usually about 0.01 to 20 ml of the pesticidal agent of the present invention per kg of body weight of the target animal.
- active ingredients can be used in combination if necessary, such as afoxolaner, umifoxolaner, tigolaner, fluralaner, mivorilaner, modoflaner. ), lotilaner, surolaner, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxifendazole, parabendazole, thiabendazole, triclabendazole, amitraz, demiditraz, clorsulon, closantel, oxyclonazide, lafoxanide, cyphenothrin, flumethrin, permethrin, cyromazine, derquantel, diamphenetide, dicyclanil, dinotefuran, imidacloprid ), nitenpyram, thiamethoxam, abamectin, doramectin, emamectin, eprinome
- the endoparasites that can be controlled by the animal endoparasite control agent of the present invention are broadly classified into protozoa and helminths.
- Protozoa that parasitic humans include, for example, amoeba (Rhizopoda) such as Entamoeba histolytica, flagellates (Mastigophora) such as Leishmania, trypanosoma, and trichomonas, sporozoa (Sporozoea) such as malaria parasites and Toxoplasma gondii, and large intestine.
- Ciliophora such as Balantidium are included, and helminths that parasitize humans include, for example, helminths, Anisakid, canis, hairy nematodes, pinworms, and hookworms (Zubini hookworm, American hookworm, Brazilian hookworm, etc.) , nematodes such as nematodes, gnathostomes, threadworms (filaria, Bancroft threadworms, Malayan threadworms, etc.), roundworms (Onchocerca), schizozoans, tricholates, strongyloids, etc.
- helminths that parasitize humans include, for example, helminths, Anisakid, canis, hairy nematodes, pinworms, and hookworms (Zubini hookworm, American hookworm, Brazilian hookworm, etc.) , nematodes such as nematodes, gnathostomes, threadworms (filaria, Bancroft threadworms, Malayan thread
- Acannthocephala (Acannthocephala), Gordiacea (Gordiacea), Hirudinea (Hirudinea), Schistosoma japonica, Schistosoma mansoni, Schistosoma bilharzia, Liver fluke, Trematodes (Trematoda) such as trematodes, leech-like trematodes, and lung flukes, tapeworms such as tapeworms, tapeworms mansoni, budworms, tapeworms great, tapeworms of the genus Taenia, tapeworms of the genus Taenia, (taenia taeniae, These include tapeworms (Cestoda) such as Taenia solium, hydatid (Echinococcus, etc.), patterned tapeworm, melid tapeworm, wire tapeworm, monkey bareheaded tapeworm, and tapeworm Nibellina. It is not limited.
- Protozoa that parasitize animals belonging to mammals or birds other than humans include coccidia (Eimeria), Isospora (Isospora), Toxoplasma (Toxoplasma), Neospora (Neospora), Sarcocystis (Sarcocystis), Coccidia such as Besnoitia, Hammondia, Cryptosporidium, and Caryospora; Haemosporina such as Leucocytozoon and Plasmodium; ), Piroplasma such as Theileria, Anaplasma, Eperythrozoon, Heamobartonella, Rhrlichia, and other apicomplexans such as Hepatozoon.
- coccidia Eimeria
- Isospora Isospora
- Toxoplasma Toxoplasma
- Neospora Neospora
- Sarcocystis Sarcocystis
- Coccidia such as Besnoitia, Hammondia, Cryptospori
- Haemogregarina Haemogregarina, Microspora, Encephalitozoon, Nosema, etc. Flagellates, Mastigophora, Trypanosoma, Leishmania, etc. Trichomonads such as Trypanosomatid, Chilomastix, Trichomonas, Monocercomonas, Histomonas, Vaccinonas such as Hexamita, Giardia, etc. Vaccinonadida, Sarcodina, amoebas such as Entamoeba, Ciliophora, Balantidium, Buxtonella, Entodinium. Such,
- helminths that parasitize animals belonging to mammals or birds other than humans include nematodes such as Ascaris, Toxocara, Toxascaris, and Parascaris. ), roundworms (Ascarida) such as Ascaridia, Heterakis and Anisakis, Oxyurida such as Oxyuris and Passalurus, strongyles ( strongylus), Haemonchus, bovine Ostertagia, Trichostrongylus, Cooperia, Nematodirus, red Hystrongylus, Oesophagostomum, Chabertia, Ancylostoma, Uncinaria, Necator, Bunostomum, Bovine Lungworm (Dictyocaulus), pig lungworm (Metastrongylus), dog lungworm (Filaroides), cat lungworm (Aelurostrongulus), Cantonese schistosome (Angiostrongylus), tracheostomy beak (Syngamus),
- Flukes include Fasciolata, such as Fasciola and Fasciolopsis, Paramphistomatidae, such as Homalogaster, Eurytrema, and lanceolates.
- Diplocoelata such as Dicrocoelium, Pharyngostomum, Diplostomata such as Alaria, Echinostoma, Echinochasmus, etc.
- Troglotrematoidea such as Echinostomata, Paragonimus, and Nanophyetus
- Opisthorchiida such as Clonorchis
- Heterophyes include Fasciolata, such as Fasciola and Fasciolopsis, Paramphistomatidae, such as Homalogaster, Eurytrema, and lanceolates.
- Diplocoelata such as Dicrocoelium, Pharyngostomum, Diplostomata such as Alaria, Echinostoma
- Heterophyida such as Metagonimus
- Plagiorchiida such as Prosthogonimus
- Schistosoma such as Schistoma
- Pseudophylidea such as Diphyllobothrium, Spirometra, Anoplocephara, Paranoplocephala, Moniezia, Dog tapeworms (Dipylidium), wired tapeworms (Mesocestoides), legume-like tapeworms, hydatid tapeworms (Tenia), cat tapeworms (Hydatigera), multicephalic tapeworms (Multiceps), monocystic tapeworms (Echinococcus), polycystic tapeworms Echinococcus, Taenia, Taeniarhynchus, Hymenolepis, Vampirolepis, Raillietina, Amoebotaenia, etc. Cyclophyllidea, etc., Macracanthorhynch
- helminths include, for example, the nematode genus Enoplida, Trichuris spp., Capillaria spp., Trichomosoides spp., Trichinella spp. spp.), examples of the genus Rhabditia include Micronema spp. and Strongyloides spp., and examples of the genus Strongylida include, for example, Stronylus. Species (Stronylus spp.), Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindrophorahynchus spp.
- Cystocaulus spp. Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Paraphylloides spp.
- Oxyurida for example, Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp. and Heterakis spp.
- Ascaridiae include, for example, Ascaris spp., Toxascaris spp., Toxocara spp., Parascaris spp. spp.), Anisakis spp., and Ascaridia spp.; examples of the Spiruride genus include Gnathosma spp., Physaloptera spp.
- Thelazia spp. Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp., etc.
- Examples of the genus Filariida include Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., and Deirofilaria. Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., etc.
- Examples of Acanthocephala include Filicollis spp., Moniliformis spp., Macracanthorhynchus spp., Prosthenorchis spp.
- Subclasses of Monogenea of trematodes include, for example, Gyrodactylus spp., Dactylogyrusspp., and Polystoma spp.
- subclasses of Digenea include, for example. , Diplostomum spp., Posthodiplostomum spp., Schistosomaspp., Trichobilharzia spp., Ornithbilharzia spp.
- Austrobilharzia spp. Gigantobilharziaspp., Leucochloridium spp., Brachylaima spp., Echinostoma spp. spp.), Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fasciolides spp., Hypertrophic fluke spp.
- tapeworms in the order Pseudophyllidea include Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., and Ligula spp. spp.), Bothridium spp., and Diplogonoporus spp., and in the Cyclophyllidea order, for example, Mesocestoides spp., Nachocephalic tapeworms.
- the animal endoparasite control agent of the present invention is effective in controlling not only parasites living in the bodies of intermediate hosts and definitive hosts, but also parasites in the host organism. Furthermore, the compound represented by the general formula (1) of the present invention exhibits a controlling effect on parasites at all stages of development. For example, in protozoa, these include cysts, pretunicate types, trophozoites, meristems in the asexual stage, amoeboid bodies, gametocytes, gametes, fusion bodies, and sporophytes in the sexual stage. In nematodes, they are eggs, larvae, and adults.
- the compound according to the present invention not only exterminates parasites within a living body, but also prevents parasite infection by applying it to the environment, which is a route of infection.
- soil-transmitted infection from soil in fields and parks percutaneous infection from water systems such as rivers, lakes, wetlands, and rice fields, oral infection from feces of animals such as dogs and cats, saltwater fish, freshwater fish, and crustaceans.
- feces of animals such as dogs and cats
- saltwater fish freshwater fish
- crustaceans It is possible to prevent oral infections from shellfish, raw livestock meat, etc., and infections from mosquitoes, horseflies, flies, cockroaches, ticks, fleas, lice, assassin bugs, chiggers, etc.
- the animal endoparasite control agent of the present invention can be administered to humans, non-human mammals, or birds as a pharmaceutical for the purpose of treating or preventing parasitic diseases.
- the administration method can be either oral administration or parenteral administration.
- oral administration by incorporating into capsules, tablets, pills, powders, granules, fine granules, powders, syrups, enteric-coated agents, suspensions, pastes, or liquid drinks or feed for animals.
- injections for parenteral administration, injections, drops, suppositories, emulsions, suspensions, drops, ointments, creams, liquids, lotions, sprays, aerosols, poultices, and tapes can be administered to mucous membranes or It is administered in a dosage form that maintains percutaneous absorption.
- the optimal amount (effective amount) of the active ingredient should be determined depending on the type of infecting parasite, whether for treatment or prevention.
- the dosage varies depending on the type and degree of infection, dosage form, etc., but in general, in the case of oral administration, it is in the range of about 0.0001 to 10,000 mg/kg body weight per day.
- the dose ranges from about 0.0001 to 10,000 mg/kg body weight per day, administered in a single dose or in divided doses.
- the concentration of the active ingredient in the animal internal parasite control agent of the present invention is generally about 0.001 to 100% by mass, preferably about 0.001 to 99%, and more preferably about 0.005 to 20% by mass.
- the animal endoparasite control agent of the present invention may be a composition to be administered as it is, or may be a highly concentrated composition that is diluted to an appropriate concentration before use.
- the other active ingredients described above can be used in combination as necessary for the purpose of reinforcing or supplementing the effects of the animal endoparasite control agent of the present invention.
- two or more active ingredients may be mixed together before administration, or two or more different formulations may be administered separately.
- 5-fluoro-2-aminopyridine (235 mg, 2.10 mmol) was dissolved in N,N-dimethylacetamide (15.0 mL), triethylamine (585 ⁇ L, 4.20 mmol), carbonyldiimidazole (372 mg, 2.31 mmol) was added at room temperature. After stirring the reaction solution at room temperature for 2 hours, 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione (300 mg, 1.05 mmol) and DBU (300 ⁇ L, 2.10 mmol) were added.
- Reference example 1 Reference Example 1-1 for the production of 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione Production of 4-ethoxy-1-(4-(trifluoromethyl)benzyl)-6,7-dihydro-1H-azepin-2(5H)-one
- Reference example 2 Reference Example 2-1 for the production of 1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione Production of 4-ethoxy-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H-azepin-2(5H)-one
- the reaction solution was heated to 110°C and stirred for 3 hours, but since the raw materials had not disappeared, copper(I) iodide (1.23 g, 6.44 mmol) and N,N-dimethylethylenediamine (692 ⁇ L) were added to the reaction solution. , 6.44 mmol) and heated at 140° C. for 8 hours. Thereafter, the reaction solution was allowed to cool to room temperature, and a liquid separation operation was performed using ethyl acetate.
- Reference example 3 Production reference example 3-1 of 6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione Production of 4-ethoxy-6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H-azepin-2(5H)-one
- Formulation example 1 Compound of the present invention: 10 parts Xylene: 70 parts N-methylpyrrolidone: 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate: 10 parts The above ingredients are uniformly mixed and dissolved to obtain an emulsion.
- Formulation example 2 Compound of the present invention: 3 parts Clay powder: 82 parts Diatomaceous earth powder: 15 parts The above ingredients are uniformly mixed and pulverized to obtain a powder.
- Formulation example 3 Compound of the present invention: 5 parts Mixed powder of bentonite and clay: 90 parts Calcium ligninsulfonate: 5 parts The above ingredients are mixed uniformly, an appropriate amount of water is added, kneaded, granulated, and dried to obtain granules.
- Formulation example 4 Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above are uniformly mixed and pulverized to prepare a wettable powder.
- Test example 1 Insecticidal test against diamondback moth (Plutella xylostella) Adult diamondback moths were released on Chinese cabbage seedlings to lay eggs, and two days after the release, the Chinese cabbage seedlings with eggs were treated with the compound represented by the general formula (1) of the present invention. The sample was immersed for about 30 seconds in a drug solution containing a drug as an active ingredient diluted to 500 ppm, air-dried, and then left in a constant temperature room at 25°C. The number of surviving insects was investigated after 6 days of immersion in the chemical solution, and the corrected mortality rate was calculated using the following formula, and judgment was made according to the following criteria. 1 ward 10 horses 3 consecutive races.
- the compounds represented by the general formula (1) of the present invention exhibited significant insecticidal activity, especially compound numbers 1-52, 1-53, 1-54, 1-55, 1-58, 1-111. , 1-112, 1-118, 1-121, 1-124, 1-127, and 1-128 showed excellent activity against diamondback moths with a grade of B or better.
- Test example 2 Test for evaluating the effect on the growth of Dirofilaria immitis A prescribed adjustment solution, 8-20 L-3 stage larvae of Dirofilaria immitis, and a DMSO diluted solution of the compound of the present invention were added to each hole of a 24-well plate. The final concentration was 10 ⁇ M. Seven days later, the larvae that had developed to the L-4 stage were counted, and the rate of growth inhibition from the L3 stage larva to the L4 stage larva was calculated.
- compound numbers 1-5, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1 -20, 1-21, 1-40, 1-43, 1-44, 1-46, 1-48, 1-49, 1-50, 1-51, 1-55, 1-56, 1-57 , 1-58 and 1-117 showed a growth inhibition rate of 50% or more.
- the compounds of the present invention and their salts have excellent effects as pest control agents.
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Abstract
In the production of crops in agriculture, horticulture, etc., due to factors such as damages caused by harmful bugs and the like still being significant and the emergence of harmful bugs resistant to existing drugs, there has been a demand for the development of a new agricultural/horticultural harmful-bug control agent. Further, in rearing of animals such as livestock and companion animals (pets), since infection by a parasite causes significant pain to animals and leads to enormous economic loss in livestock, there has been a demand for the development of a new external parasite control agent for animals and a new internal parasite control agent for animals. The present invention provides a compound represented by general formula (1) {in the formula, X represents a hydroxy group, etc., Y represents an oxygen atom or a sulfur atom, etc., R1 represents a substituted phenyl group, etc., R2a, R2b, R3a, R3b, R4a, and R4b represent a hydrogen atom, etc., R5 represents a substituted phenyl group, etc., R6 represents a hydrogen atom, etc.} or salts thereof, a harmful organism control agent having said compound as an active ingredient, and a method for using the same.
Description
本発明は、アゼパンジオン誘導体又はその塩類及び該化合物を含有する有害生物防除剤並びにその使用方法に関する。
The present invention relates to an azepanedione derivative or a salt thereof, a pest control agent containing the compound, and a method for using the same.
特許文献1及び2には、ある種のアゼパンジオン誘導体が医薬用化合物として報告されている。また、特許文献3には、ある種のアゼパンジオン誘導体が医薬用化合物の中間体として報告されている。しかしかかる文献中には、該化合物の農園芸分野の害虫や動物の寄生虫のような有害生物に対する防除活性については記載も示唆もされていない。
Patent Documents 1 and 2 report certain azepanedione derivatives as pharmaceutical compounds. Furthermore, Patent Document 3 reports certain azepanedione derivatives as intermediates for pharmaceutical compounds. However, these documents do not describe or suggest the control activity of these compounds against harmful organisms such as pests in the field of agriculture and horticulture and parasites of animals.
農業及び園芸などの有用作物の生産において、害虫による被害は甚大であり、これに有効な農園芸用害虫防除剤が数多く上市されている。しかしながら、既存薬に対する抵抗性害虫にも効果の高い薬剤、各種の省力的な施用方法に適した物性を備えた薬剤、急性毒性などの軽減された人畜安全性に優れた薬剤、適切な土壌残留性など環境安全性に優れた薬剤の要望などから、新規な農園芸用害虫防除剤の開発は、現在でも農園芸分野の重要な課題の一つである。また、家畜、愛玩動物(ペット)などの動物飼育においても寄生虫の防除は重要な課題である。寄生虫の感染は、それ自体に加えて、寄生虫から伝染されるウィルス、細菌などによる疾病の両方が動物に著しい苦痛をもたらし、家畜では甚大な経済的損失となるため、新規な動物用外部寄生虫防除剤及び動物用内部寄生虫防除剤の開発が望まれている。
In the production of useful crops such as agriculture and horticulture, the damage caused by pests is enormous, and there are many effective agricultural and horticultural pest control agents on the market. However, there are still drugs that are highly effective against pests that are resistant to existing drugs, drugs that have physical properties suitable for various labor-saving application methods, drugs with excellent human and animal safety with reduced acute toxicity, and appropriate soil residues. The development of new pest control agents for agriculture and horticulture is still one of the important issues in the field of agriculture and horticulture, due to the demand for agents that have excellent environmental safety such as toxicity. In addition, parasite control is an important issue when raising animals such as livestock and companion animals (pets). Infection with parasites causes significant suffering to animals, as well as diseases caused by viruses and bacteria transmitted by the parasites, resulting in huge economic losses for livestock. The development of parasite control agents and endoparasite control agents for animals is desired.
本発明者等は新規な有害生物防除剤、特に農園芸用害虫防除剤、動物用外部寄生虫防除剤及び動物用内部寄生虫防除剤を開発すべく鋭意研究を重ねた結果、本発明の一般式(1)で表されるカルボキサミドのカルボン酸部位としてアゼパン‐2,4‐ジオン誘導体を有する化合物又はその塩類が、有害生物防除剤として有用であることを見いだし、本発明を完成させた。
The present inventors have conducted intensive research to develop new pest control agents, particularly agricultural and horticultural pest control agents, animal ectoparasite control agents, and animal endoparasite control agents. The present invention was completed based on the discovery that a compound having an azepane-2,4-dione derivative as the carboxylic acid moiety of the carboxamide represented by formula (1) or a salt thereof is useful as a pest control agent.
即ち本発明は、
[1]一般式(1)
{式中、
R1は、
(a1) 水素原子;(a2) (C1-C6)アルキル基;(a3) (C2-C6)アルケニル基;(a4) (C2-C6)アルキニル基;(a5) (C3-C6)シクロアルキル基;(a6) ハロ(C1-C6)アルキル基;(a7) ハロ(C2-C6)アルケニル基;(a8) ハロ(C2-C6)アルキニル基;(a9) ハロ(C3-C6)シクロアルキル基;(a10) 置換基群Aからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C1-C6)アルキル基;(a11) 置換基群Bからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C3-C6)シクロアルキル基;(a12) (C1-C6)アルコキシカルボニル基;(a13) N‐(C1-C6)アルキルアミノカルボニル基;(a14) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(a15) フェニルアミノカルボニル基;(a16) フェニル(C1-C6)アルキル基;(a17) 置換基群Cからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基;(a18) ピリジル(C1-C6)アルキル基;(a19) 置換基群Cからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル(C1-C6)アルキル基;(a20) ピリダジニル(C1-C6)アルキル基;(a21) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル(C1-C6)アルキル基;(a22) ピラジニル(C1-C6)アルキル基;(a23) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル(C1-C6)アルキル基;(a24) ピリミジニル(C1-C6)アルキル基;(a25) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル(C1-C6)アルキル基;(a26) オキサゾリル(C1-C6)アルキル基;(a27) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル(C1-C6)アルキル基;(a28) イソキサゾリル(C1-C6)アルキル基;(a29) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル(C1-C6)アルキル基;(a30) チエニル(C1-C6)アルキル基;(a31) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換チエニル(C1-C6)アルキル基;(a32) チアゾリル(C1-C6)アルキル基;(a33) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル(C1-C6)アルキル基;(a34) イソチアゾリル(C1-C6)アルキル基;(a35) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソチアゾリル(C1-C6)アルキル基;(a36) チアジアゾリル(C1-C6)アルキル基;(a37) 置換基群Cから選択される1個の置換基を環上に有する置換チアジアゾリル(C1-C6)アルキル基;(a38) ピラゾリル(C1-C6)アルキル基;(a39) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル(C1-C6)アルキル基;(a40) トリアゾリル(C1-C6)アルキル基;(a41) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル(C1-C6)アルキル基;(a42) テトラゾリル(C1-C6)アルキル基;(a43) 置換基群Cから選択される1個の置換基を環上に有する置換テトラゾリル(C1-C6)アルキル基;(a44) フェニル基;(a45) 置換基群Dからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(a46) ピリジル基;(a47) 置換基群Dからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(a48) ピリダジニル基;(a49) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル基;(a50) ピラジニル基;(a51) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル基;(a52) ピリミジニル基;(a53) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(a54) オキサゾリル基;(a55) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル基;(a56) イソキサゾリル基;(a57) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル基;(a58) チエニル基;(a59) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換チエニル基;(a60) チアゾリル基;(a61) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(a62) イソチアゾリル基;(a63) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソチアゾリル基;(a64) チアジアゾリル基;(a65) 置換基群Dから選択される1個の置換基を環上に有する置換チアジアゾリル基;(a66) ピラゾリル基;(a67) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(a68) トリアゾリル基;(a69) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル基;(a70) テトラゾリル基;(a71) 置換基群Dから選択される1個の置換基を環上に有する置換テトラゾリル基;(a72) ベンゾチアゾリル基;又は(a73) 置換基群Dから選択される1乃至4個の置換基を環上に有する置換ベンゾチアゾリル基を示す。
R2aは、
(b1) 水素原子;又は(b2) (C1-C6)アルキル基を示す。
R2bは、
(c1) 水素原子;又は(c2) (C1-C6)アルキル基を示す。
R3aは、
(d1) 水素原子;(d2) (C1-C6)アルキル基;(d3) フェニル基;又は(d4) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基を示す。
R3bは、
(e1) 水素原子;又は(e2) (C1-C6)アルキル基を示す。
R4aは、
(f1) 水素原子;又は(f2) (C1-C6)アルキル基を示す。
R4bは、
(g1) 水素原子;又は(g2) (C1-C6)アルキル基を示す。
R5は、
(h1) (C1-C6)アルキル基;(h2) (C2-C6)アルケニル基;(h3) (C2-C6)アルキニル基;(h4) (C3-C6)シクロアルキル基;(h5) ハロ(C1-C6)アルキル基;(h6) ハロ(C2-C6)アルケニル基;(h7) ハロ(C2-C6)アルキニル基;(h8) ハロ(C3-C6)シクロアルキル基;(h9) 置換基群Aからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C1-C6)アルキル基;(h10) 置換基群Bからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換(C3-C6)シクロアルキル基;(h11) フェニル基;(h12) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(h13) ピリジル基;(h14) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(h15) ピリダジニル基;(h16) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル基;(h17) ピリミジニル基;(h18) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(h19) ピラジニル基;(h20) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル基;(h21) トリアジニル基;(h22) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアジニル基;(h23) フラニル基;(h24) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換フラニル基;(h25) オキサゾリル基;(h26) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル基;(h27) イソキサゾリル基;(h28) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル基;(h29) チエニル基;(h30) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換チエニル基;(h31) チアゾリル基;(h32) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(h33) イソチアゾリル基;(h34) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソチアゾリル基;(h35) チアジアゾリル基;(h36) 置換基群Eから選択される1個の置換基を環上に有する置換チアジアゾリル基;(h37) ピラゾリル基;(h38) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(h39) トリアゾリル基;(h40) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル基;(h41) テトラゾリル基;(h42) 置換基群Eから選択される1個の置換基を環上に有する置換テトラゾリル基;(h43) ベンゾオキサゾリル基;(h44) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ベンゾオキサゾリル基;(h45) ベンゾチアゾリル基;(h46) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ベンゾチアゾリル基;(h47) キノリニル基;(h48) 置換基群Eからそれぞれ独立に選択される1乃至6個の置換基を環上に有する置換キノリニル基;(h49) ナフチル基;(h50) 置換基群Eからそれぞれ独立に選択される1乃至7個の置換基を環上に有する置換ナフチル基;(h51) テトラヒドロナフチル基;(h52) 置換基群Eからそれぞれ独立に選択される1乃至10個の置換基を環上に有する置換テトラヒドロナフチル基;(h53) フェニル(C1-C6)アルキル基;(h54) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基;(h55) ピリジル(C1-C6)アルキル基;(h56) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル(C1-C6)アルキル基;(h57) ピリダジニル(C1-C6)アルキル基;(h58) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル(C1-C6)アルキル基;(h59) ピラジニル(C1-C6)アルキル基;(h60) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル(C1-C6)アルキル基;(h61) ピリミジニル(C1-C6)アルキル基;又は(h62) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル(C1-C6)アルキル基を示す。
R6は、
(i1) 水素原子;(i2) (C1-C6)アルキル基;(i3) (C3-C6)シクロアルキル基;(i4) (C1-C6)アルコキシ基;又は(i5) (C1-C6)アルキルカルボニル基を示す。
Xは、ヒドロキシル基、(C1-C6)アルコキシ基、(C1-C6)アルキルスルファニル基、(C1-C6)アルキルスルフィニル基、又は(C1-C6)アルキルスルホニル基を示す。
Yは、酸素原子、硫黄原子、又はNR7基(式中、R7は、水素原子、(C1-C6)アルキル基、又はハロゲン原子、シアノ基、(C1-C6)アルキル基、及びハロ(C1-C6)アルキル基からなる群からそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基を示す。)を示す。
置換基群Aは、
(j1) シアノ基;(j2) (C1-C6)アルキル基;(j3) (C2-C6)アルケニル基;(j4) (C2-C6)アルキニル基;(j5) (C3-C6)シクロアルキル基;(j6) (C1-C6)アルコキシ基;(j7) (C1-C6)アルキルスルファニル基;(j8) (C1-C6)アルキルスルフィニル基;(j9) (C1-C6)アルキルスルホニル基;(j10) ハロ(C1-C6)アルキル基;(j11) ハロ(C2-C6)アルケニル基;(j12) ハロ(C2-C6)アルキニル基;(j13) ハロ(C3-C6)シクロアルキル基;(j14) ハロ(C1-C6)アルコキシ基;(j15) ハロ(C1-C6)アルキルスルファニル基;(j16) ハロ(C1-C6)アルキルスルフィニル基;(j17) ハロ(C1-C6)アルキルスルホニル基;(j18) (C1-C6)アルコキシカルボニル基;及び(j19) ハロ(C1-C6)アルコキシカルボニル基からなる。
置換基群Bは、
(k1) シアノ基;(k2) (C1-C6)アルキル基;(k3) (C2-C6)アルケニル基;(k4) (C2-C6)アルキニル基;(k5) (C3-C6)シクロアルキル基;(k6) (C1-C6)アルコキシ基;(k7) (C1-C6)アルキルスルファニル基;(k8) (C1-C6)アルキルスルフィニル基;(k9) (C1-C6)アルキルスルホニル基;(k10) ハロ(C1-C6)アルキル基;(k11) ハロ(C3-C6)シクロアルキル基;(k12) ハロ(C1-C6)アルコキシ基;(k13) ハロ(C1-C6)アルキルスルファニル基;(k14) ハロ(C1-C6)アルキルスルフィニル基;(k15) ハロ(C1-C6)アルキルスルホニル基;及び(k16) フェニル基からなる。
置換基群Cは、
(l1) ハロゲン原子;(l2) シアノ基;(l3) ニトロ基;(l4) ヒドロキシル基;(l5) カルボキシル基;(l6) (C1-C6)アルキル基;(l7) (C2-C6)アルケニル基;(l8) (C2-C6)アルキニル基;(l9) (C1-C6)アルコキシ基;(l10) (C3-C6)シクロアルキル基;(l11) (C1-C6)アルキルスルファニル基;(l12) (C1-C6)アルキルスルフィニル基;(l13) (C1-C6)アルキルスルホニル基;(l14) ハロ(C1-C6)アルキル基;(l15) ハロ(C2-C6)アルケニル基;(l16) ハロ(C2-C6)アルキニル基;(l17) ハロ(C1-C6)アルコキシ基;(l18) ハロ(C3-C6)シクロアルキル基;(l19) ハロ(C1-C6)アルキルスルファニル基;(l20) ハロ(C1-C6)アルキルスルフィニル基;(l21) ハロ(C1-C6)アルキルスルホニル基;(l22) (C1-C6)アルキルカルボニル基;(l23) (C1-C6)アルコキシカルボニル基;(l24) (C1-C6)アルキルカルボニルアミノ基;(l25) ハロ(C1-C6)アルキルカルボニルアミノ基;(l26) (C1-C6)アルキルスルホニルアミノ基;(l27) ハロ(C1-C6)アルキルスルホニルアミノ基;(l28) N‐(C1-C6)アルキルアミノカルボニル基;(l29) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(l30) N‐ハロ(C1-C6)アルキルアミノカルボニル基;(l31) N‐(C1-C6)アルキルアミノスルホニル基;及び(l32) N,N‐ジ(C1-C6)アルキルアミノスルホニル基(当該(C1-C6)アルキルは、同一又は異なってもよい)からなる。
置換基群Dは、
(m1) ハロゲン原子;(m2) シアノ基;(m3) ニトロ基;(m4) アミノ基;(m5) ヒドロキシル基;(m6) カルボキシル基;(m7) (C1-C6)アルキル基;(m8) (C2-C6)アルケニル基;(m9) (C2-C6)アルキニル基;(m10) (C1-C6)アルコキシ基;(m11) (C3-C6)シクロアルキル基;(m12) (C1-C6)アルキルスルファニル基;(m13) (C1-C6)アルキルスルフィニル基;(m14) (C1-C6)アルキルスルホニル基;(m15) ハロ(C1-C6)アルキル基;(m16) ハロ(C2-C6)アルケニル基;(m17) ハロ(C2-C6)アルキニル基;(m18) ハロ(C1-C6)アルコキシ基;(m19) ハロ(C3-C6)シクロアルキル基;(m20) ハロ(C1-C6)アルキルスルファニル基;(m21) ハロ(C1-C6)アルキルスルフィニル基;(m22) ハロ(C1-C6)アルキルスルホニル基;(m23) シアノ基、(C1-C6)アルキル基、ハロ(C1-C6)アルキル基、(C1-C6)アルコキシ基及び(C1-C6)アルキルカルボニル基からなる群からそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換(C3-C6)シクロアルキル基;(m24) (C1-C6)アルコキシ(C1-C6)アルキル基;(m25) (C1-C6)アルコキシ(C1-C6)アルコキシ基;(m26) (C1-C6)アルキルカルボニルアミノ基;(m27) ハロ(C1-C6)アルキルカルボニルアミノ基;(m28) (C1-C6)アルキルスルホニルアミノ基;(m29) ハロ(C1-C6)アルキルスルホニルアミノ基;(m30) (C1-C6)アルコキシカルボニル基;(m31) N‐(C1-C6)アルキルアミノカルボニル基;(m32) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(m33) N‐ハロ(C1-C6)アルキルアミノカルボニル基;(m34) N‐(C1-C6)アルキルアミノスルホニル基;(m35) N,N‐ジ(C1-C6)アルキルアミノスルホニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);及び(m36) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基からなる。
置換基群Eは、
(n1) ハロゲン原子;(n2) シアノ基;(n3) ニトロ基;(n4) アミノ基;(n5) ヒドロキシル基;(n6) カルボキシル基;(n7) (C1-C6)アルキル基;(n8) (C1-C6)アルコキシ基;(n9) (C3-C6)シクロアルキル基;(n10) (C1-C6)アルキルスルファニル基;(n11) (C1-C6)アルキルスルフィニル基;(n12) (C1-C6)アルキルスルホニル基;(n13) ハロ(C1-C6)アルキル基;(n14) ハロ(C1-C6)アルコキシ基;(n15) ハロ(C3-C6)シクロアルキル基;(n16) ハロ(C1-C6)アルキルスルファニル基;(n17) ハロ(C1-C6)アルキルスルフィニル基;(n18) ハロ(C1-C6)アルキルスルホニル基;(n19) (C1-C6)アルキルカルボニルアミノ基;(n20) ハロ(C1-C6)アルキルカルボニルアミノ基;(n21) (C1-C6)アルキルスルホニルアミノ基;(n22) ハロ(C1-C6)アルキルスルホニルアミノ基;(n23) (C1-C6)アルコキシカルボニル基;(n24) N‐(C1-C6)アルキルアミノカルボニル基;(n25) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(n26) N‐ハロ(C1-C6)アルキルアミノカルボニル基;(n27) フェニル基;(n28) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(n29) ピラゾリル基;(n30) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(n31) フェノキシ基;(n32) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェノキシ基;(n33) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基;(n34) N‐(C1-C6)アルキルアミノスルホニル基;及び(n35) N,N‐ジ(C1-C6)アルキルアミノスルホニル基(当該(C1-C6)アルキルは、同一又は異なってもよい)からなる。
但し、R1の(a45)置換フェニル基、(a47)置換ピリジル基、(a49)置換ピリダジニル基、(a51)置換ピラジニル基、(a53)置換ピリミジニル基、(a55)置換オキサゾリル基、(a57)置換イソキサゾリル基、(a59)置換チエニル基、(a61)置換チアゾリル基、(a63)置換イソチアゾリル基、(a65)置換チアジアゾリル基、(a67)置換ピラゾリル基、(a69)置換トリアゾリル基、(a71)置換テトラゾリル基、及び(a73)置換ベンゾチアゾリル基は、アゼパン‐2,4‐ジオン環との結合原子の隣接原子に(C1-C6)アルキルスルホニル基、ハロ(C1-C6)アルキルスルホニル基、N‐(C1-C6)アルキルアミノスルホニル基、又はN,N‐ジ(C1-C6)アルキルアミノスルホニル基は置換しない。
}で表される化合物又はその塩類、 That is, the present invention
[1] General formula (1)
{During the ceremony,
R 1 is
(a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 - C 6 ) cycloalkyl group; (a6) halo (C 1 - C 6 ) alkyl group; (a7) halo (C 2 - C 6 ) alkenyl group; (a8) halo (C 2 - C 6 ) alkynyl group (a9) halo(C 3 -C 6 )cycloalkyl group; (a10) substituted (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (a11) Substituted (C 3 - C 6 ) cycloalkyl group having 1 to 3 substituents each independently selected from substituent group B; (a12) (C 1 -C 6 ) alkoxycarbonyl group; ( a13) N-(C 1 -C 6 )alkylaminocarbonyl group; (a14) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkyl groups are the same or different) (a15) phenylaminocarbonyl group; (a16) phenyl (C 1 -C 6 ) alkyl group; (a17) 1 to 5 substituents independently selected from substituent group C; Substituted phenyl (C 1 -C 6 ) alkyl group possessed above; (a18) Pyridyl (C 1 -C 6 ) alkyl group; (a19) 1 to 4 substituents each independently selected from Substituent Group C Substituted pyridyl (C 1 -C 6 ) alkyl group having on the ring; (a20) pyridazinyl (C 1 -C 6 ) alkyl group; (a21) 1 to 3 groups each independently selected from substituent group C; Substituted pyridazinyl (C 1 -C 6 ) alkyl group having a substituent on the ring; (a22) Pyrazinyl (C 1 -C 6 ) alkyl group; (a23) 1 to 3 each independently selected from substituent group C Substituted pyrazinyl (C 1 -C 6 ) alkyl group having 3 substituents on the ring; (a24) Pyrimidinyl (C 1 -C 6 ) alkyl group; (a25) 1 each independently selected from substituent group C; Substituted pyrimidinyl (C 1 -C 6 ) alkyl group having from 3 substituents on the ring; (a26) oxazolyl (C 1 -C 6 ) alkyl group; (a27) each independently selected from substituent group C; a substituted oxazolyl (C 1 -C 6 ) alkyl group having 1 or 2 substituents on the ring; (a28) an isoxazolyl (C 1 -C 6 ) alkyl group; (a29) each independently from substituent group C; Substituted isoxazolyl (C 1 -C 6 ) alkyl group having 1 or 2 selected substituents on the ring; (a30) Thienyl (C 1 -C 6 ) alkyl group; (a31) Each from substituent group C Substituted thienyl (C 1 -C 6 ) alkyl group having 1 to 3 independently selected substituents on the ring; (a32) Thiazolyl (C 1 -C 6 ) alkyl group; (a33) Substituent group C Substituted thiazolyl (C 1 -C 6 ) alkyl group having 1 or 2 substituents on the ring, each independently selected from; (a34) Isothiazolyl (C 1 -C 6 ) alkyl group; (a35) Substituent Substituted isothiazolyl (C 1 -C 6 ) alkyl group having 1 to 2 substituents independently selected from Group C on the ring; (a36) Thiadiazolyl (C 1 -C 6 ) alkyl group; (a37) Substituted thiadiazolyl (C 1 -C 6 ) alkyl group having one substituent selected from substituent group C on the ring; (a38) Pyrazolyl (C 1 -C 6 ) alkyl group; (a39) Substituent group Substituted pyrazolyl (C 1 -C 6 ) alkyl group having 1 to 3 substituents independently selected from C on the ring; (a40) Triazolyl (C 1 -C 6 ) alkyl group; (a41) Substituted Substituted triazolyl (C 1 -C 6 ) alkyl group having 1 or 2 substituents independently selected from group C on the ring; (a42) Tetrazolyl (C 1 -C 6 ) alkyl group; (a43) ) a substituted tetrazolyl (C 1 -C 6 ) alkyl group having one substituent selected from substituent group C on the ring; (a44) a phenyl group; (a45) each independently selected from substituent group D; Substituted phenyl group having 1 to 5 substituents on the ring; (a46) Pyridyl group; (a47) Substituted phenyl group having 1 to 4 substituents on the ring, each independently selected from Substituent Group D Pyridyl group; (a48) Pyridazinyl group; (a49) Substituted pyridazinyl group having 1 to 3 substituents on the ring, each independently selected from Substituent Group D; (a50) Pyrazinyl group; (a51) Substituent Substituted pyrazinyl group having 1 to 3 substituents each independently selected from Group D on the ring; (a52) Pyrimidinyl group; (a53) 1 to 3 substituents each independently selected from Substituent Group D Substituted pyrimidinyl group having a substituent on the ring; (a54) Oxazolyl group; (a55) Substituted oxazolyl group having one or two substituents on the ring, each independently selected from Substituent Group D; (a56) Isoxazolyl group; (a57) Substituted isoxazolyl group having 1 or 2 substituents on the ring each independently selected from Substituent Group D; (a58) Thienyl group; (a59) Each independently from Substituent Group D Substituted thienyl group having 1 to 3 selected substituents on the ring; (a60) Thiazolyl group; (a61) 1 to 2 substituents each independently selected from Substituent Group D on the ring a substituted thiazolyl group; (a62) an isothiazolyl group; (a63) a substituted isothiazolyl group having on the ring one or two substituents each independently selected from substituent group D; (a64) a thiadiazolyl group; (a65) Substituted thiadiazolyl group having one substituent selected from substituent group D on the ring; (a66) Pyrazolyl group; (a67) Substituted thiadiazolyl group having one to three substituents each independently selected from substituent group D Substituted pyrazolyl group having on the ring; (a68) Triazolyl group; (a69) Substituted triazolyl group having 1 to 2 substituents each independently selected from Substituent Group D on the ring; (a70) Tetrazolyl group; (a71) Substituted tetrazolyl group having one substituent selected from substituent group D on the ring; (a72) benzothiazolyl group; or (a73) 1 to 4 substituents selected from substituent group D represents a substituted benzothiazolyl group having on the ring.
R 2a is
(b1) A hydrogen atom; or (b2) a (C 1 -C 6 ) alkyl group.
R2b is
(c1) A hydrogen atom; or (c2) a (C 1 -C 6 ) alkyl group.
R 3a is
(d1) Hydrogen atom; (d2) (C 1 -C 6 ) alkyl group; (d3) Phenyl group; or (d4) Halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) Substituted phenyl having 1 to 5 substituents on the ring, each independently selected from the group consisting of an alkoxy group, a halo(C 1 -C 6 )alkyl group, and a halo(C 1 -C 6 )alkoxy group Indicates the group.
R 3b is
(e1) A hydrogen atom; or (e2) (C 1 -C 6 ) alkyl group.
R 4a is
(f1) A hydrogen atom; or (f2) a (C 1 -C 6 ) alkyl group.
R 4b is
(g1) a hydrogen atom; or (g2) a (C 1 -C 6 ) alkyl group.
R5 is
(h1) (C 1 -C 6 ) alkyl group; (h2) (C 2 -C 6 ) alkenyl group; (h3) (C 2 -C 6 ) alkynyl group; (h4) (C 3 -C 6 ) cyclo Alkyl group; (h5) halo (C 1 - C 6 ) alkyl group; (h6) halo (C 2 - C 6 ) alkenyl group; (h7) halo (C 2 - C 6 ) alkynyl group; (h8) halo ( C 3 -C 6 ) cycloalkyl group; (h9) substituted (C 1 -C 6 ) alkyl group having 1 to 3 substituents each independently selected from substituent group A; (h10) substituent group Substituted (C 3 - C 6 ) cycloalkyl group having 1 to 3 substituents on the ring, each independently selected from B; (h11) phenyl group; (h12) each independently selected from substituent group E a substituted phenyl group having 1 to 5 substituents on the ring; (h13) a pyridyl group; (h14) having 1 to 4 substituents on the ring, each independently selected from substituent group E; Substituted pyridyl group; (h15) pyridazinyl group; (h16) substituted pyridazinyl group having 1 to 3 substituents on the ring, each independently selected from substituent group E; (h17) pyrimidinyl group; (h18) substituted Substituted pyrimidinyl group having 1 to 3 substituents each independently selected from group E on the ring; (h19) Pyrazinyl group; (h20) 1 to 3 substituents each independently selected from substituent group E Substituted pyrazinyl group having on the ring a substituent; (h21) Triazinyl group; (h22) Substituted triazinyl group having one or two substituents on the ring, each independently selected from substituent group E; (h23) ) Furanyl group; (h24) Substituted furanyl group having 1 to 3 substituents on the ring, each independently selected from Substituent Group E; (h25) Oxazolyl group; (h26) Each independently from Substituent Group E Substituted oxazolyl group having 1 to 2 substituents selected on the ring; (h27) Isoxazolyl group; (h29) a thienyl group; (h30) a substituted thienyl group having on its ring 1 to 3 substituents each independently selected from substituent group E; (h31) a thiazolyl group; (h32) ) Substituted thiazolyl group having 1 to 2 substituents on the ring, each independently selected from substituent group E; (h33) Isothiazolyl group; (h34) 1 to 2 each independently selected from substituent group E Substituted isothiazolyl group having two substituents on the ring; (h35) Thiadiazolyl group; (h36) Substituted thiadiazolyl group having one substituent selected from Substituent Group E on the ring; (h37) Pyrazolyl group (h38) Substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from substituent group E; (h39) Triazolyl group; (h40) Substituted pyrazolyl group, each independently selected from substituent group E Substituted triazolyl group having one or two substituents on the ring; (h41) Tetrazolyl group; (h42) Substituted tetrazolyl group having one substituent selected from substituent group E on the ring; (h43) ) Benzoxazolyl group; (h44) Substituted benzoxazolyl group having 1 to 4 substituents on the ring, each independently selected from Substituent Group E; (h45) Benzothiazolyl group; (h46) Substituted Substituted benzothiazolyl group having 1 to 4 substituents each independently selected from group E on the ring; (h47) Quinolinyl group; (h48) 1 to 6 substituents each independently selected from substituent group E Substituted quinolinyl group having on the ring a substituent; (h49) Naphthyl group; (h50) Substituted naphthyl group having 1 to 7 substituents on the ring, each independently selected from substituent group E; (h51 ) Tetrahydronaphthyl group; (h52) Substituted tetrahydronaphthyl group having 1 to 10 substituents on the ring, each independently selected from Substituent Group E; (h53) Phenyl (C 1 -C 6 ) alkyl group; (h54) Substituted phenyl (C 1 -C 6 ) alkyl group having 1 to 5 substituents on the ring, each independently selected from substituent group E; (h55) Pyridyl (C 1 -C 6 ) alkyl group Group; (h56) Substituted pyridyl (C 1 -C 6 ) alkyl group having on the ring 1 to 4 substituents each independently selected from Substituent Group E; (h57) Pyridazinyl (C 1 -C 6 ) alkyl group; (h58) substituted pyridazinyl (C 1 -C 6 ) alkyl group having on the ring 1 to 3 substituents each independently selected from substituent group E; (h59) pyrazinyl (C 1 - C 6 ) alkyl group; (h60) substituted pyrazinyl (C 1 -C 6 ) alkyl group having on the ring 1 to 3 substituents each independently selected from substituent group E; (h61) pyrimidinyl (C 1 -C 6 ) alkyl group; or (h62) represents a substituted pyrimidinyl (C 1 -C 6 ) alkyl group having 1 to 3 substituents independently selected from substituent group E on the ring.
R6 is
(i1) Hydrogen atom; (i2) (C 1 -C 6 ) alkyl group; (i3) (C 3 -C 6 ) cycloalkyl group; (i4) (C 1 -C 6 ) alkoxy group; or (i5) (C 1 -C 6 ) represents an alkylcarbonyl group.
X is a hydroxyl group, a (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 )alkylsulfanyl group, a (C 1 -C 6 )alkylsulfinyl group, or a (C 1 -C 6 )alkylsulfonyl group. show.
Y is an oxygen atom, a sulfur atom, or an NR 7 group (wherein R 7 is a hydrogen atom, a (C 1 -C 6 ) alkyl group, or a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group) , and a halo(C 1 -C 6 )alkyl group, each having 1 to 4 substituents on the ring.
Substituent group A is
(j1) Cyano group; (j2) (C 1 -C 6 ) alkyl group; (j3) (C 2 -C 6 ) alkenyl group; (j4) (C 2 -C 6 ) alkynyl group; (j5) (C 3 - C6 ) cycloalkyl group; (j6) ( C1 - C6 ) alkoxy group; (j7) ( C1 - C6 ) alkylsulfanyl group; (j8) ( C1 - C6 ) alkylsulfinyl group; (j9) (C 1 -C 6 )alkylsulfonyl group; (j10) Halo (C 1 -C 6 ) alkyl group; (j11) Halo (C 2 -C 6 ) alkenyl group; (j12) Halo (C 2 - C 6 ) alkynyl group; (j13) halo(C 3 -C 6 )cycloalkyl group; (j14) halo(C 1 -C 6 )alkoxy group; (j15) halo(C 1 -C 6 )alkylsulfanyl group; (j16) halo(C 1 -C 6 )alkylsulfinyl group; (j17) halo(C 1 -C 6 )alkylsulfonyl group; (j18) (C 1 -C 6 )alkoxycarbonyl group; and (j19) halo( C 1 -C 6 ) alkoxycarbonyl group.
Substituent group B is
(k1) Cyano group; (k2) (C 1 -C 6 ) alkyl group; (k3) (C 2 -C 6 ) alkenyl group; (k4) (C 2 -C 6 ) alkynyl group; (k5) (C 3 - C6 ) cycloalkyl group; (k6) ( C1 - C6 ) alkoxy group; (k7) ( C1 - C6 ) alkylsulfanyl group; (k8) ( C1 - C6 ) alkylsulfinyl group; (k9) (C 1 - C 6 ) alkylsulfonyl group; (k10) halo (C 1 - C 6 ) alkyl group; (k11) halo (C 3 - C 6 ) cycloalkyl group; (k12) halo (C 1 -C 6 ) alkoxy group; (k13) halo(C 1 -C 6 )alkylsulfanyl group; (k14) halo(C 1 -C 6 )alkylsulfinyl group; (k15) halo(C 1 -C 6 )alkylsulfonyl and (k16) a phenyl group.
Substituent group C is
(l1) Halogen atom; (l2) Cyano group; (l3) Nitro group; (l4) Hydroxyl group; (l5) Carboxyl group; (l6) (C 1 - C 6 ) alkyl group; (l7) (C 2 - C 6 ) alkenyl group; (l8) (C 2 -C 6 ) alkynyl group; (l9) (C 1 -C 6 ) alkoxy group; (l10) (C 3 -C 6 ) cycloalkyl group; (l11) ( C 1 -C 6 )alkylsulfanyl group; (l12) (C 1 -C 6 )alkylsulfinyl group; (l13) (C 1 -C 6 )alkylsulfonyl group; (l14) halo(C 1 -C 6 )alkyl Group; (l15) Halo (C 2 - C 6 ) alkenyl group; (l16) Halo (C 2 - C 6 ) alkynyl group; (l17) Halo (C 1 - C 6 ) alkoxy group; (l18) Halo (C 3 -C 6 )cycloalkyl group; (l19) halo(C 1 -C 6 )alkylsulfanyl group; (l20) halo(C 1 -C 6 )alkylsulfinyl group; (l21) halo(C 1 -C 6 ) Alkylsulfonyl group; (l22) (C 1 - C 6 ) alkylcarbonyl group; (l23) (C 1 - C 6 ) alkoxycarbonyl group; (l24) (C 1 - C 6 ) alkylcarbonylamino group; (l25) Halo(C 1 -C 6 )alkylcarbonylamino group; (l26) (C 1 -C 6 )alkylsulfonylamino group; (l27) Halo(C 1 -C 6 )alkylsulfonylamino group; (l28) N-( C 1 -C 6 ) alkylaminocarbonyl group; (l29) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 ) alkyl groups may be the same or different); (l30) N-halo(C 1 -C 6 )alkylaminocarbonyl group; (l31) N-(C 1 -C 6 )alkylaminosulfonyl group; and (l32) N,N-di(C 1 -C 6 ) alkylaminosulfonyl group (the (C 1 -C 6 )alkyl groups may be the same or different).
Substituent group D is
(m1) Halogen atom; (m2) Cyano group; (m3) Nitro group; (m4) Amino group; (m5) Hydroxyl group; (m6) Carboxyl group; (m7) (C 1 - C 6 ) alkyl group; ( m8) (C 2 - C 6 ) alkenyl group; (m9) (C 2 - C 6 ) alkynyl group; (m10) (C 1 - C 6 ) alkoxy group; (m11) (C 3 - C 6 ) cycloalkyl Group; (m12) (C 1 -C 6 )alkylsulfanyl group; (m13) (C 1 -C 6 )alkylsulfinyl group; (m14) (C 1 -C 6 )alkylsulfonyl group; (m15) Halo (C 1 - C 6 ) alkyl group; (m16) halo (C 2 - C 6 ) alkenyl group; (m17) halo (C 2 - C 6 ) alkynyl group; (m18) halo (C 1 - C 6 ) alkoxy group; (m19) Halo(C 3 -C 6 )cycloalkyl group; (m20) Halo(C 1 -C 6 )alkylsulfanyl group; (m21) Halo(C 1 -C 6 )alkylsulfinyl group; (m22) Halo( C 1 -C 6 )alkylsulfonyl group; (m23) cyano group, (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group and (C 1 Substituted (C 3 -C 6 ) cycloalkyl group having on the ring 1 to 3 substituents each independently selected from the group consisting of -C 6 ) alkylcarbonyl group; (m24) (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (m25) (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy group; (m26) (C 1 -C 6 ) alkylcarbonylamino group; (m27 ) Halo(C 1 -C 6 )alkylcarbonylamino group; (m28) (C 1 -C 6 )alkylsulfonylamino group; (m29) Halo(C 1 -C 6 )alkylsulfonylamino group; (m30) (C 1 -C 6 )alkoxycarbonyl group; (m31) N-(C 1 -C 6 )alkylaminocarbonyl group; (m32) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkylaminocarbonyl group; -C 6 ) alkyl may be the same or different); (m33) N-halo(C 1 -C 6 ) alkylaminocarbonyl group; (m34) N-(C 1 -C 6 ) alkylaminosulfonyl group; (m35) N,N-di(C 1 -C 6 )alkylaminosulfonyl group (the (C 1 -C 6 )alkyl groups may be the same or different); and (m36) two adjacent substitutions The group consists of a methylenedioxy group which is optionally substituted with one or two substituents selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group.
The substituent group E is
(n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n4) Amino group; (n5) Hydroxyl group; (n6) Carboxyl group; (n7) (C 1 - C 6 ) alkyl group; ( n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 - C 6 ) cycloalkyl group; (n10) (C 1 - C 6 ) alkylsulfanyl group; (n11) (C 1 - C 6 ) Alkylsulfinyl group; (n12) (C 1 - C 6 ) alkyl sulfonyl group; (n13) halo (C 1 - C 6 ) alkyl group; (n14) halo (C 1 - C 6 ) alkoxy group; (n15) halo (C 3 - C 6 ) cycloalkyl group; (n16) halo (C 1 - C 6 ) alkylsulfanyl group; (n17) halo (C 1 - C 6 ) alkyl sulfinyl group; (n18) halo (C 1 - C 6 ) Alkylsulfonyl group; (n19) (C 1 - C 6 ) alkylcarbonylamino group; (n20) Halo (C 1 - C 6 ) alkylcarbonylamino group; (n21) (C 1 - C 6 ) alkylsulfonylamino group Group; (n22) Halo(C 1 -C 6 )alkylsulfonylamino group; (n23) (C 1 -C 6 ) alkoxycarbonyl group; (n24) N-(C 1 -C 6 )alkylaminocarbonyl group; ( n25) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkyl groups may be the same or different); (n26) N-halo(C 1 -C 6 ) alkylaminocarbonyl group; (n27) phenyl group; (n28) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkyl Substituted phenyl group having 1 to 5 substituents on the ring each independently selected from the group consisting of C 1 - C 6 alkoxy groups; (n29) pyrazolyl group; (n30) halogen atom, each independently from the group consisting of a cyano group, a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group, a halo(C 1 -C 6 )alkyl group and a halo(C 1 -C 6 )alkoxy group; Substituted pyrazolyl group having 1 to 3 substituents selected on the ring; (n31) Phenoxy group; (n32) Halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) Substituted phenoxy having 1 to 5 substituents on the ring, each independently selected from the group consisting of an alkoxy group, a halo(C 1 -C 6 )alkyl group, and a halo(C 1 -C 6 )alkoxy group Group; (n33) Substituted with 1 or 2 substituents selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group formed by two adjacent substituents taken together. optional methylenedioxy group; (n34) N-(C 1 -C 6 )alkylaminosulfonyl group; and (n35) N,N-di(C 1 -C 6 )alkylaminosulfonyl group (the (C 1 -C 6 )alkyl may be the same or different).
However, R 1 's (a45) substituted phenyl group, (a47) substituted pyridyl group, (a49) substituted pyridazinyl group, (a51) substituted pyrazinyl group, (a53) substituted pyrimidinyl group, (a55) substituted oxazolyl group, (a57) Substituted isoxazolyl group, (a59) substituted thienyl group, (a61) substituted thiazolyl group, (a63) substituted isothiazolyl group, (a65) substituted thiadiazolyl group, (a67) substituted pyrazolyl group, (a69) substituted triazolyl group, (a71) substituted Tetrazolyl group and (a73) substituted benzothiazolyl group have a (C 1 -C 6 )alkylsulfonyl group or a halo(C 1 -C 6 )alkylsulfonyl group on the atom adjacent to the atom bonded to the azepane-2,4-dione ring. , N-(C 1 -C 6 )alkylaminosulfonyl group, or N,N-di(C 1 -C 6 )alkylaminosulfonyl group is not substituted.
} or its salts,
[1]一般式(1)
R1は、
(a1) 水素原子;(a2) (C1-C6)アルキル基;(a3) (C2-C6)アルケニル基;(a4) (C2-C6)アルキニル基;(a5) (C3-C6)シクロアルキル基;(a6) ハロ(C1-C6)アルキル基;(a7) ハロ(C2-C6)アルケニル基;(a8) ハロ(C2-C6)アルキニル基;(a9) ハロ(C3-C6)シクロアルキル基;(a10) 置換基群Aからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C1-C6)アルキル基;(a11) 置換基群Bからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C3-C6)シクロアルキル基;(a12) (C1-C6)アルコキシカルボニル基;(a13) N‐(C1-C6)アルキルアミノカルボニル基;(a14) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(a15) フェニルアミノカルボニル基;(a16) フェニル(C1-C6)アルキル基;(a17) 置換基群Cからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基;(a18) ピリジル(C1-C6)アルキル基;(a19) 置換基群Cからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル(C1-C6)アルキル基;(a20) ピリダジニル(C1-C6)アルキル基;(a21) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル(C1-C6)アルキル基;(a22) ピラジニル(C1-C6)アルキル基;(a23) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル(C1-C6)アルキル基;(a24) ピリミジニル(C1-C6)アルキル基;(a25) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル(C1-C6)アルキル基;(a26) オキサゾリル(C1-C6)アルキル基;(a27) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル(C1-C6)アルキル基;(a28) イソキサゾリル(C1-C6)アルキル基;(a29) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル(C1-C6)アルキル基;(a30) チエニル(C1-C6)アルキル基;(a31) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換チエニル(C1-C6)アルキル基;(a32) チアゾリル(C1-C6)アルキル基;(a33) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル(C1-C6)アルキル基;(a34) イソチアゾリル(C1-C6)アルキル基;(a35) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソチアゾリル(C1-C6)アルキル基;(a36) チアジアゾリル(C1-C6)アルキル基;(a37) 置換基群Cから選択される1個の置換基を環上に有する置換チアジアゾリル(C1-C6)アルキル基;(a38) ピラゾリル(C1-C6)アルキル基;(a39) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル(C1-C6)アルキル基;(a40) トリアゾリル(C1-C6)アルキル基;(a41) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル(C1-C6)アルキル基;(a42) テトラゾリル(C1-C6)アルキル基;(a43) 置換基群Cから選択される1個の置換基を環上に有する置換テトラゾリル(C1-C6)アルキル基;(a44) フェニル基;(a45) 置換基群Dからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(a46) ピリジル基;(a47) 置換基群Dからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(a48) ピリダジニル基;(a49) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル基;(a50) ピラジニル基;(a51) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル基;(a52) ピリミジニル基;(a53) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(a54) オキサゾリル基;(a55) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル基;(a56) イソキサゾリル基;(a57) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル基;(a58) チエニル基;(a59) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換チエニル基;(a60) チアゾリル基;(a61) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(a62) イソチアゾリル基;(a63) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソチアゾリル基;(a64) チアジアゾリル基;(a65) 置換基群Dから選択される1個の置換基を環上に有する置換チアジアゾリル基;(a66) ピラゾリル基;(a67) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(a68) トリアゾリル基;(a69) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル基;(a70) テトラゾリル基;(a71) 置換基群Dから選択される1個の置換基を環上に有する置換テトラゾリル基;(a72) ベンゾチアゾリル基;又は(a73) 置換基群Dから選択される1乃至4個の置換基を環上に有する置換ベンゾチアゾリル基を示す。
R2aは、
(b1) 水素原子;又は(b2) (C1-C6)アルキル基を示す。
R2bは、
(c1) 水素原子;又は(c2) (C1-C6)アルキル基を示す。
R3aは、
(d1) 水素原子;(d2) (C1-C6)アルキル基;(d3) フェニル基;又は(d4) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基を示す。
R3bは、
(e1) 水素原子;又は(e2) (C1-C6)アルキル基を示す。
R4aは、
(f1) 水素原子;又は(f2) (C1-C6)アルキル基を示す。
R4bは、
(g1) 水素原子;又は(g2) (C1-C6)アルキル基を示す。
R5は、
(h1) (C1-C6)アルキル基;(h2) (C2-C6)アルケニル基;(h3) (C2-C6)アルキニル基;(h4) (C3-C6)シクロアルキル基;(h5) ハロ(C1-C6)アルキル基;(h6) ハロ(C2-C6)アルケニル基;(h7) ハロ(C2-C6)アルキニル基;(h8) ハロ(C3-C6)シクロアルキル基;(h9) 置換基群Aからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C1-C6)アルキル基;(h10) 置換基群Bからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換(C3-C6)シクロアルキル基;(h11) フェニル基;(h12) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(h13) ピリジル基;(h14) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(h15) ピリダジニル基;(h16) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル基;(h17) ピリミジニル基;(h18) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(h19) ピラジニル基;(h20) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル基;(h21) トリアジニル基;(h22) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアジニル基;(h23) フラニル基;(h24) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換フラニル基;(h25) オキサゾリル基;(h26) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル基;(h27) イソキサゾリル基;(h28) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル基;(h29) チエニル基;(h30) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換チエニル基;(h31) チアゾリル基;(h32) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(h33) イソチアゾリル基;(h34) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソチアゾリル基;(h35) チアジアゾリル基;(h36) 置換基群Eから選択される1個の置換基を環上に有する置換チアジアゾリル基;(h37) ピラゾリル基;(h38) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(h39) トリアゾリル基;(h40) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル基;(h41) テトラゾリル基;(h42) 置換基群Eから選択される1個の置換基を環上に有する置換テトラゾリル基;(h43) ベンゾオキサゾリル基;(h44) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ベンゾオキサゾリル基;(h45) ベンゾチアゾリル基;(h46) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ベンゾチアゾリル基;(h47) キノリニル基;(h48) 置換基群Eからそれぞれ独立に選択される1乃至6個の置換基を環上に有する置換キノリニル基;(h49) ナフチル基;(h50) 置換基群Eからそれぞれ独立に選択される1乃至7個の置換基を環上に有する置換ナフチル基;(h51) テトラヒドロナフチル基;(h52) 置換基群Eからそれぞれ独立に選択される1乃至10個の置換基を環上に有する置換テトラヒドロナフチル基;(h53) フェニル(C1-C6)アルキル基;(h54) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基;(h55) ピリジル(C1-C6)アルキル基;(h56) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル(C1-C6)アルキル基;(h57) ピリダジニル(C1-C6)アルキル基;(h58) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル(C1-C6)アルキル基;(h59) ピラジニル(C1-C6)アルキル基;(h60) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル(C1-C6)アルキル基;(h61) ピリミジニル(C1-C6)アルキル基;又は(h62) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル(C1-C6)アルキル基を示す。
R6は、
(i1) 水素原子;(i2) (C1-C6)アルキル基;(i3) (C3-C6)シクロアルキル基;(i4) (C1-C6)アルコキシ基;又は(i5) (C1-C6)アルキルカルボニル基を示す。
Xは、ヒドロキシル基、(C1-C6)アルコキシ基、(C1-C6)アルキルスルファニル基、(C1-C6)アルキルスルフィニル基、又は(C1-C6)アルキルスルホニル基を示す。
Yは、酸素原子、硫黄原子、又はNR7基(式中、R7は、水素原子、(C1-C6)アルキル基、又はハロゲン原子、シアノ基、(C1-C6)アルキル基、及びハロ(C1-C6)アルキル基からなる群からそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基を示す。)を示す。
置換基群Aは、
(j1) シアノ基;(j2) (C1-C6)アルキル基;(j3) (C2-C6)アルケニル基;(j4) (C2-C6)アルキニル基;(j5) (C3-C6)シクロアルキル基;(j6) (C1-C6)アルコキシ基;(j7) (C1-C6)アルキルスルファニル基;(j8) (C1-C6)アルキルスルフィニル基;(j9) (C1-C6)アルキルスルホニル基;(j10) ハロ(C1-C6)アルキル基;(j11) ハロ(C2-C6)アルケニル基;(j12) ハロ(C2-C6)アルキニル基;(j13) ハロ(C3-C6)シクロアルキル基;(j14) ハロ(C1-C6)アルコキシ基;(j15) ハロ(C1-C6)アルキルスルファニル基;(j16) ハロ(C1-C6)アルキルスルフィニル基;(j17) ハロ(C1-C6)アルキルスルホニル基;(j18) (C1-C6)アルコキシカルボニル基;及び(j19) ハロ(C1-C6)アルコキシカルボニル基からなる。
置換基群Bは、
(k1) シアノ基;(k2) (C1-C6)アルキル基;(k3) (C2-C6)アルケニル基;(k4) (C2-C6)アルキニル基;(k5) (C3-C6)シクロアルキル基;(k6) (C1-C6)アルコキシ基;(k7) (C1-C6)アルキルスルファニル基;(k8) (C1-C6)アルキルスルフィニル基;(k9) (C1-C6)アルキルスルホニル基;(k10) ハロ(C1-C6)アルキル基;(k11) ハロ(C3-C6)シクロアルキル基;(k12) ハロ(C1-C6)アルコキシ基;(k13) ハロ(C1-C6)アルキルスルファニル基;(k14) ハロ(C1-C6)アルキルスルフィニル基;(k15) ハロ(C1-C6)アルキルスルホニル基;及び(k16) フェニル基からなる。
置換基群Cは、
(l1) ハロゲン原子;(l2) シアノ基;(l3) ニトロ基;(l4) ヒドロキシル基;(l5) カルボキシル基;(l6) (C1-C6)アルキル基;(l7) (C2-C6)アルケニル基;(l8) (C2-C6)アルキニル基;(l9) (C1-C6)アルコキシ基;(l10) (C3-C6)シクロアルキル基;(l11) (C1-C6)アルキルスルファニル基;(l12) (C1-C6)アルキルスルフィニル基;(l13) (C1-C6)アルキルスルホニル基;(l14) ハロ(C1-C6)アルキル基;(l15) ハロ(C2-C6)アルケニル基;(l16) ハロ(C2-C6)アルキニル基;(l17) ハロ(C1-C6)アルコキシ基;(l18) ハロ(C3-C6)シクロアルキル基;(l19) ハロ(C1-C6)アルキルスルファニル基;(l20) ハロ(C1-C6)アルキルスルフィニル基;(l21) ハロ(C1-C6)アルキルスルホニル基;(l22) (C1-C6)アルキルカルボニル基;(l23) (C1-C6)アルコキシカルボニル基;(l24) (C1-C6)アルキルカルボニルアミノ基;(l25) ハロ(C1-C6)アルキルカルボニルアミノ基;(l26) (C1-C6)アルキルスルホニルアミノ基;(l27) ハロ(C1-C6)アルキルスルホニルアミノ基;(l28) N‐(C1-C6)アルキルアミノカルボニル基;(l29) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(l30) N‐ハロ(C1-C6)アルキルアミノカルボニル基;(l31) N‐(C1-C6)アルキルアミノスルホニル基;及び(l32) N,N‐ジ(C1-C6)アルキルアミノスルホニル基(当該(C1-C6)アルキルは、同一又は異なってもよい)からなる。
置換基群Dは、
(m1) ハロゲン原子;(m2) シアノ基;(m3) ニトロ基;(m4) アミノ基;(m5) ヒドロキシル基;(m6) カルボキシル基;(m7) (C1-C6)アルキル基;(m8) (C2-C6)アルケニル基;(m9) (C2-C6)アルキニル基;(m10) (C1-C6)アルコキシ基;(m11) (C3-C6)シクロアルキル基;(m12) (C1-C6)アルキルスルファニル基;(m13) (C1-C6)アルキルスルフィニル基;(m14) (C1-C6)アルキルスルホニル基;(m15) ハロ(C1-C6)アルキル基;(m16) ハロ(C2-C6)アルケニル基;(m17) ハロ(C2-C6)アルキニル基;(m18) ハロ(C1-C6)アルコキシ基;(m19) ハロ(C3-C6)シクロアルキル基;(m20) ハロ(C1-C6)アルキルスルファニル基;(m21) ハロ(C1-C6)アルキルスルフィニル基;(m22) ハロ(C1-C6)アルキルスルホニル基;(m23) シアノ基、(C1-C6)アルキル基、ハロ(C1-C6)アルキル基、(C1-C6)アルコキシ基及び(C1-C6)アルキルカルボニル基からなる群からそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換(C3-C6)シクロアルキル基;(m24) (C1-C6)アルコキシ(C1-C6)アルキル基;(m25) (C1-C6)アルコキシ(C1-C6)アルコキシ基;(m26) (C1-C6)アルキルカルボニルアミノ基;(m27) ハロ(C1-C6)アルキルカルボニルアミノ基;(m28) (C1-C6)アルキルスルホニルアミノ基;(m29) ハロ(C1-C6)アルキルスルホニルアミノ基;(m30) (C1-C6)アルコキシカルボニル基;(m31) N‐(C1-C6)アルキルアミノカルボニル基;(m32) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(m33) N‐ハロ(C1-C6)アルキルアミノカルボニル基;(m34) N‐(C1-C6)アルキルアミノスルホニル基;(m35) N,N‐ジ(C1-C6)アルキルアミノスルホニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);及び(m36) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基からなる。
置換基群Eは、
(n1) ハロゲン原子;(n2) シアノ基;(n3) ニトロ基;(n4) アミノ基;(n5) ヒドロキシル基;(n6) カルボキシル基;(n7) (C1-C6)アルキル基;(n8) (C1-C6)アルコキシ基;(n9) (C3-C6)シクロアルキル基;(n10) (C1-C6)アルキルスルファニル基;(n11) (C1-C6)アルキルスルフィニル基;(n12) (C1-C6)アルキルスルホニル基;(n13) ハロ(C1-C6)アルキル基;(n14) ハロ(C1-C6)アルコキシ基;(n15) ハロ(C3-C6)シクロアルキル基;(n16) ハロ(C1-C6)アルキルスルファニル基;(n17) ハロ(C1-C6)アルキルスルフィニル基;(n18) ハロ(C1-C6)アルキルスルホニル基;(n19) (C1-C6)アルキルカルボニルアミノ基;(n20) ハロ(C1-C6)アルキルカルボニルアミノ基;(n21) (C1-C6)アルキルスルホニルアミノ基;(n22) ハロ(C1-C6)アルキルスルホニルアミノ基;(n23) (C1-C6)アルコキシカルボニル基;(n24) N‐(C1-C6)アルキルアミノカルボニル基;(n25) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(n26) N‐ハロ(C1-C6)アルキルアミノカルボニル基;(n27) フェニル基;(n28) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(n29) ピラゾリル基;(n30) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(n31) フェノキシ基;(n32) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェノキシ基;(n33) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基;(n34) N‐(C1-C6)アルキルアミノスルホニル基;及び(n35) N,N‐ジ(C1-C6)アルキルアミノスルホニル基(当該(C1-C6)アルキルは、同一又は異なってもよい)からなる。
但し、R1の(a45)置換フェニル基、(a47)置換ピリジル基、(a49)置換ピリダジニル基、(a51)置換ピラジニル基、(a53)置換ピリミジニル基、(a55)置換オキサゾリル基、(a57)置換イソキサゾリル基、(a59)置換チエニル基、(a61)置換チアゾリル基、(a63)置換イソチアゾリル基、(a65)置換チアジアゾリル基、(a67)置換ピラゾリル基、(a69)置換トリアゾリル基、(a71)置換テトラゾリル基、及び(a73)置換ベンゾチアゾリル基は、アゼパン‐2,4‐ジオン環との結合原子の隣接原子に(C1-C6)アルキルスルホニル基、ハロ(C1-C6)アルキルスルホニル基、N‐(C1-C6)アルキルアミノスルホニル基、又はN,N‐ジ(C1-C6)アルキルアミノスルホニル基は置換しない。
}で表される化合物又はその塩類、 That is, the present invention
[1] General formula (1)
R 1 is
(a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 - C 6 ) cycloalkyl group; (a6) halo (C 1 - C 6 ) alkyl group; (a7) halo (C 2 - C 6 ) alkenyl group; (a8) halo (C 2 - C 6 ) alkynyl group (a9) halo(C 3 -C 6 )cycloalkyl group; (a10) substituted (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (a11) Substituted (C 3 - C 6 ) cycloalkyl group having 1 to 3 substituents each independently selected from substituent group B; (a12) (C 1 -C 6 ) alkoxycarbonyl group; ( a13) N-(C 1 -C 6 )alkylaminocarbonyl group; (a14) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkyl groups are the same or different) (a15) phenylaminocarbonyl group; (a16) phenyl (C 1 -C 6 ) alkyl group; (a17) 1 to 5 substituents independently selected from substituent group C; Substituted phenyl (C 1 -C 6 ) alkyl group possessed above; (a18) Pyridyl (C 1 -C 6 ) alkyl group; (a19) 1 to 4 substituents each independently selected from Substituent Group C Substituted pyridyl (C 1 -C 6 ) alkyl group having on the ring; (a20) pyridazinyl (C 1 -C 6 ) alkyl group; (a21) 1 to 3 groups each independently selected from substituent group C; Substituted pyridazinyl (C 1 -C 6 ) alkyl group having a substituent on the ring; (a22) Pyrazinyl (C 1 -C 6 ) alkyl group; (a23) 1 to 3 each independently selected from substituent group C Substituted pyrazinyl (C 1 -C 6 ) alkyl group having 3 substituents on the ring; (a24) Pyrimidinyl (C 1 -C 6 ) alkyl group; (a25) 1 each independently selected from substituent group C; Substituted pyrimidinyl (C 1 -C 6 ) alkyl group having from 3 substituents on the ring; (a26) oxazolyl (C 1 -C 6 ) alkyl group; (a27) each independently selected from substituent group C; a substituted oxazolyl (C 1 -C 6 ) alkyl group having 1 or 2 substituents on the ring; (a28) an isoxazolyl (C 1 -C 6 ) alkyl group; (a29) each independently from substituent group C; Substituted isoxazolyl (C 1 -C 6 ) alkyl group having 1 or 2 selected substituents on the ring; (a30) Thienyl (C 1 -C 6 ) alkyl group; (a31) Each from substituent group C Substituted thienyl (C 1 -C 6 ) alkyl group having 1 to 3 independently selected substituents on the ring; (a32) Thiazolyl (C 1 -C 6 ) alkyl group; (a33) Substituent group C Substituted thiazolyl (C 1 -C 6 ) alkyl group having 1 or 2 substituents on the ring, each independently selected from; (a34) Isothiazolyl (C 1 -C 6 ) alkyl group; (a35) Substituent Substituted isothiazolyl (C 1 -C 6 ) alkyl group having 1 to 2 substituents independently selected from Group C on the ring; (a36) Thiadiazolyl (C 1 -C 6 ) alkyl group; (a37) Substituted thiadiazolyl (C 1 -C 6 ) alkyl group having one substituent selected from substituent group C on the ring; (a38) Pyrazolyl (C 1 -C 6 ) alkyl group; (a39) Substituent group Substituted pyrazolyl (C 1 -C 6 ) alkyl group having 1 to 3 substituents independently selected from C on the ring; (a40) Triazolyl (C 1 -C 6 ) alkyl group; (a41) Substituted Substituted triazolyl (C 1 -C 6 ) alkyl group having 1 or 2 substituents independently selected from group C on the ring; (a42) Tetrazolyl (C 1 -C 6 ) alkyl group; (a43) ) a substituted tetrazolyl (C 1 -C 6 ) alkyl group having one substituent selected from substituent group C on the ring; (a44) a phenyl group; (a45) each independently selected from substituent group D; Substituted phenyl group having 1 to 5 substituents on the ring; (a46) Pyridyl group; (a47) Substituted phenyl group having 1 to 4 substituents on the ring, each independently selected from Substituent Group D Pyridyl group; (a48) Pyridazinyl group; (a49) Substituted pyridazinyl group having 1 to 3 substituents on the ring, each independently selected from Substituent Group D; (a50) Pyrazinyl group; (a51) Substituent Substituted pyrazinyl group having 1 to 3 substituents each independently selected from Group D on the ring; (a52) Pyrimidinyl group; (a53) 1 to 3 substituents each independently selected from Substituent Group D Substituted pyrimidinyl group having a substituent on the ring; (a54) Oxazolyl group; (a55) Substituted oxazolyl group having one or two substituents on the ring, each independently selected from Substituent Group D; (a56) Isoxazolyl group; (a57) Substituted isoxazolyl group having 1 or 2 substituents on the ring each independently selected from Substituent Group D; (a58) Thienyl group; (a59) Each independently from Substituent Group D Substituted thienyl group having 1 to 3 selected substituents on the ring; (a60) Thiazolyl group; (a61) 1 to 2 substituents each independently selected from Substituent Group D on the ring a substituted thiazolyl group; (a62) an isothiazolyl group; (a63) a substituted isothiazolyl group having on the ring one or two substituents each independently selected from substituent group D; (a64) a thiadiazolyl group; (a65) Substituted thiadiazolyl group having one substituent selected from substituent group D on the ring; (a66) Pyrazolyl group; (a67) Substituted thiadiazolyl group having one to three substituents each independently selected from substituent group D Substituted pyrazolyl group having on the ring; (a68) Triazolyl group; (a69) Substituted triazolyl group having 1 to 2 substituents each independently selected from Substituent Group D on the ring; (a70) Tetrazolyl group; (a71) Substituted tetrazolyl group having one substituent selected from substituent group D on the ring; (a72) benzothiazolyl group; or (a73) 1 to 4 substituents selected from substituent group D represents a substituted benzothiazolyl group having on the ring.
R 2a is
(b1) A hydrogen atom; or (b2) a (C 1 -C 6 ) alkyl group.
R2b is
(c1) A hydrogen atom; or (c2) a (C 1 -C 6 ) alkyl group.
R 3a is
(d1) Hydrogen atom; (d2) (C 1 -C 6 ) alkyl group; (d3) Phenyl group; or (d4) Halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) Substituted phenyl having 1 to 5 substituents on the ring, each independently selected from the group consisting of an alkoxy group, a halo(C 1 -C 6 )alkyl group, and a halo(C 1 -C 6 )alkoxy group Indicates the group.
R 3b is
(e1) A hydrogen atom; or (e2) (C 1 -C 6 ) alkyl group.
R 4a is
(f1) A hydrogen atom; or (f2) a (C 1 -C 6 ) alkyl group.
R 4b is
(g1) a hydrogen atom; or (g2) a (C 1 -C 6 ) alkyl group.
R5 is
(h1) (C 1 -C 6 ) alkyl group; (h2) (C 2 -C 6 ) alkenyl group; (h3) (C 2 -C 6 ) alkynyl group; (h4) (C 3 -C 6 ) cyclo Alkyl group; (h5) halo (C 1 - C 6 ) alkyl group; (h6) halo (C 2 - C 6 ) alkenyl group; (h7) halo (C 2 - C 6 ) alkynyl group; (h8) halo ( C 3 -C 6 ) cycloalkyl group; (h9) substituted (C 1 -C 6 ) alkyl group having 1 to 3 substituents each independently selected from substituent group A; (h10) substituent group Substituted (C 3 - C 6 ) cycloalkyl group having 1 to 3 substituents on the ring, each independently selected from B; (h11) phenyl group; (h12) each independently selected from substituent group E a substituted phenyl group having 1 to 5 substituents on the ring; (h13) a pyridyl group; (h14) having 1 to 4 substituents on the ring, each independently selected from substituent group E; Substituted pyridyl group; (h15) pyridazinyl group; (h16) substituted pyridazinyl group having 1 to 3 substituents on the ring, each independently selected from substituent group E; (h17) pyrimidinyl group; (h18) substituted Substituted pyrimidinyl group having 1 to 3 substituents each independently selected from group E on the ring; (h19) Pyrazinyl group; (h20) 1 to 3 substituents each independently selected from substituent group E Substituted pyrazinyl group having on the ring a substituent; (h21) Triazinyl group; (h22) Substituted triazinyl group having one or two substituents on the ring, each independently selected from substituent group E; (h23) ) Furanyl group; (h24) Substituted furanyl group having 1 to 3 substituents on the ring, each independently selected from Substituent Group E; (h25) Oxazolyl group; (h26) Each independently from Substituent Group E Substituted oxazolyl group having 1 to 2 substituents selected on the ring; (h27) Isoxazolyl group; (h29) a thienyl group; (h30) a substituted thienyl group having on its ring 1 to 3 substituents each independently selected from substituent group E; (h31) a thiazolyl group; (h32) ) Substituted thiazolyl group having 1 to 2 substituents on the ring, each independently selected from substituent group E; (h33) Isothiazolyl group; (h34) 1 to 2 each independently selected from substituent group E Substituted isothiazolyl group having two substituents on the ring; (h35) Thiadiazolyl group; (h36) Substituted thiadiazolyl group having one substituent selected from Substituent Group E on the ring; (h37) Pyrazolyl group (h38) Substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from substituent group E; (h39) Triazolyl group; (h40) Substituted pyrazolyl group, each independently selected from substituent group E Substituted triazolyl group having one or two substituents on the ring; (h41) Tetrazolyl group; (h42) Substituted tetrazolyl group having one substituent selected from substituent group E on the ring; (h43) ) Benzoxazolyl group; (h44) Substituted benzoxazolyl group having 1 to 4 substituents on the ring, each independently selected from Substituent Group E; (h45) Benzothiazolyl group; (h46) Substituted Substituted benzothiazolyl group having 1 to 4 substituents each independently selected from group E on the ring; (h47) Quinolinyl group; (h48) 1 to 6 substituents each independently selected from substituent group E Substituted quinolinyl group having on the ring a substituent; (h49) Naphthyl group; (h50) Substituted naphthyl group having 1 to 7 substituents on the ring, each independently selected from substituent group E; (h51 ) Tetrahydronaphthyl group; (h52) Substituted tetrahydronaphthyl group having 1 to 10 substituents on the ring, each independently selected from Substituent Group E; (h53) Phenyl (C 1 -C 6 ) alkyl group; (h54) Substituted phenyl (C 1 -C 6 ) alkyl group having 1 to 5 substituents on the ring, each independently selected from substituent group E; (h55) Pyridyl (C 1 -C 6 ) alkyl group Group; (h56) Substituted pyridyl (C 1 -C 6 ) alkyl group having on the ring 1 to 4 substituents each independently selected from Substituent Group E; (h57) Pyridazinyl (C 1 -C 6 ) alkyl group; (h58) substituted pyridazinyl (C 1 -C 6 ) alkyl group having on the ring 1 to 3 substituents each independently selected from substituent group E; (h59) pyrazinyl (C 1 - C 6 ) alkyl group; (h60) substituted pyrazinyl (C 1 -C 6 ) alkyl group having on the ring 1 to 3 substituents each independently selected from substituent group E; (h61) pyrimidinyl (C 1 -C 6 ) alkyl group; or (h62) represents a substituted pyrimidinyl (C 1 -C 6 ) alkyl group having 1 to 3 substituents independently selected from substituent group E on the ring.
R6 is
(i1) Hydrogen atom; (i2) (C 1 -C 6 ) alkyl group; (i3) (C 3 -C 6 ) cycloalkyl group; (i4) (C 1 -C 6 ) alkoxy group; or (i5) (C 1 -C 6 ) represents an alkylcarbonyl group.
X is a hydroxyl group, a (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 )alkylsulfanyl group, a (C 1 -C 6 )alkylsulfinyl group, or a (C 1 -C 6 )alkylsulfonyl group. show.
Y is an oxygen atom, a sulfur atom, or an NR 7 group (wherein R 7 is a hydrogen atom, a (C 1 -C 6 ) alkyl group, or a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group) , and a halo(C 1 -C 6 )alkyl group, each having 1 to 4 substituents on the ring.
Substituent group A is
(j1) Cyano group; (j2) (C 1 -C 6 ) alkyl group; (j3) (C 2 -C 6 ) alkenyl group; (j4) (C 2 -C 6 ) alkynyl group; (j5) (C 3 - C6 ) cycloalkyl group; (j6) ( C1 - C6 ) alkoxy group; (j7) ( C1 - C6 ) alkylsulfanyl group; (j8) ( C1 - C6 ) alkylsulfinyl group; (j9) (C 1 -C 6 )alkylsulfonyl group; (j10) Halo (C 1 -C 6 ) alkyl group; (j11) Halo (C 2 -C 6 ) alkenyl group; (j12) Halo (C 2 - C 6 ) alkynyl group; (j13) halo(C 3 -C 6 )cycloalkyl group; (j14) halo(C 1 -C 6 )alkoxy group; (j15) halo(C 1 -C 6 )alkylsulfanyl group; (j16) halo(C 1 -C 6 )alkylsulfinyl group; (j17) halo(C 1 -C 6 )alkylsulfonyl group; (j18) (C 1 -C 6 )alkoxycarbonyl group; and (j19) halo( C 1 -C 6 ) alkoxycarbonyl group.
Substituent group B is
(k1) Cyano group; (k2) (C 1 -C 6 ) alkyl group; (k3) (C 2 -C 6 ) alkenyl group; (k4) (C 2 -C 6 ) alkynyl group; (k5) (C 3 - C6 ) cycloalkyl group; (k6) ( C1 - C6 ) alkoxy group; (k7) ( C1 - C6 ) alkylsulfanyl group; (k8) ( C1 - C6 ) alkylsulfinyl group; (k9) (C 1 - C 6 ) alkylsulfonyl group; (k10) halo (C 1 - C 6 ) alkyl group; (k11) halo (C 3 - C 6 ) cycloalkyl group; (k12) halo (C 1 -C 6 ) alkoxy group; (k13) halo(C 1 -C 6 )alkylsulfanyl group; (k14) halo(C 1 -C 6 )alkylsulfinyl group; (k15) halo(C 1 -C 6 )alkylsulfonyl and (k16) a phenyl group.
Substituent group C is
(l1) Halogen atom; (l2) Cyano group; (l3) Nitro group; (l4) Hydroxyl group; (l5) Carboxyl group; (l6) (C 1 - C 6 ) alkyl group; (l7) (C 2 - C 6 ) alkenyl group; (l8) (C 2 -C 6 ) alkynyl group; (l9) (C 1 -C 6 ) alkoxy group; (l10) (C 3 -C 6 ) cycloalkyl group; (l11) ( C 1 -C 6 )alkylsulfanyl group; (l12) (C 1 -C 6 )alkylsulfinyl group; (l13) (C 1 -C 6 )alkylsulfonyl group; (l14) halo(C 1 -C 6 )alkyl Group; (l15) Halo (C 2 - C 6 ) alkenyl group; (l16) Halo (C 2 - C 6 ) alkynyl group; (l17) Halo (C 1 - C 6 ) alkoxy group; (l18) Halo (C 3 -C 6 )cycloalkyl group; (l19) halo(C 1 -C 6 )alkylsulfanyl group; (l20) halo(C 1 -C 6 )alkylsulfinyl group; (l21) halo(C 1 -C 6 ) Alkylsulfonyl group; (l22) (C 1 - C 6 ) alkylcarbonyl group; (l23) (C 1 - C 6 ) alkoxycarbonyl group; (l24) (C 1 - C 6 ) alkylcarbonylamino group; (l25) Halo(C 1 -C 6 )alkylcarbonylamino group; (l26) (C 1 -C 6 )alkylsulfonylamino group; (l27) Halo(C 1 -C 6 )alkylsulfonylamino group; (l28) N-( C 1 -C 6 ) alkylaminocarbonyl group; (l29) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 ) alkyl groups may be the same or different); (l30) N-halo(C 1 -C 6 )alkylaminocarbonyl group; (l31) N-(C 1 -C 6 )alkylaminosulfonyl group; and (l32) N,N-di(C 1 -C 6 ) alkylaminosulfonyl group (the (C 1 -C 6 )alkyl groups may be the same or different).
Substituent group D is
(m1) Halogen atom; (m2) Cyano group; (m3) Nitro group; (m4) Amino group; (m5) Hydroxyl group; (m6) Carboxyl group; (m7) (C 1 - C 6 ) alkyl group; ( m8) (C 2 - C 6 ) alkenyl group; (m9) (C 2 - C 6 ) alkynyl group; (m10) (C 1 - C 6 ) alkoxy group; (m11) (C 3 - C 6 ) cycloalkyl Group; (m12) (C 1 -C 6 )alkylsulfanyl group; (m13) (C 1 -C 6 )alkylsulfinyl group; (m14) (C 1 -C 6 )alkylsulfonyl group; (m15) Halo (C 1 - C 6 ) alkyl group; (m16) halo (C 2 - C 6 ) alkenyl group; (m17) halo (C 2 - C 6 ) alkynyl group; (m18) halo (C 1 - C 6 ) alkoxy group; (m19) Halo(C 3 -C 6 )cycloalkyl group; (m20) Halo(C 1 -C 6 )alkylsulfanyl group; (m21) Halo(C 1 -C 6 )alkylsulfinyl group; (m22) Halo( C 1 -C 6 )alkylsulfonyl group; (m23) cyano group, (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group and (C 1 Substituted (C 3 -C 6 ) cycloalkyl group having on the ring 1 to 3 substituents each independently selected from the group consisting of -C 6 ) alkylcarbonyl group; (m24) (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (m25) (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy group; (m26) (C 1 -C 6 ) alkylcarbonylamino group; (m27 ) Halo(C 1 -C 6 )alkylcarbonylamino group; (m28) (C 1 -C 6 )alkylsulfonylamino group; (m29) Halo(C 1 -C 6 )alkylsulfonylamino group; (m30) (C 1 -C 6 )alkoxycarbonyl group; (m31) N-(C 1 -C 6 )alkylaminocarbonyl group; (m32) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkylaminocarbonyl group; -C 6 ) alkyl may be the same or different); (m33) N-halo(C 1 -C 6 ) alkylaminocarbonyl group; (m34) N-(C 1 -C 6 ) alkylaminosulfonyl group; (m35) N,N-di(C 1 -C 6 )alkylaminosulfonyl group (the (C 1 -C 6 )alkyl groups may be the same or different); and (m36) two adjacent substitutions The group consists of a methylenedioxy group which is optionally substituted with one or two substituents selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group.
The substituent group E is
(n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n4) Amino group; (n5) Hydroxyl group; (n6) Carboxyl group; (n7) (C 1 - C 6 ) alkyl group; ( n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 - C 6 ) cycloalkyl group; (n10) (C 1 - C 6 ) alkylsulfanyl group; (n11) (C 1 - C 6 ) Alkylsulfinyl group; (n12) (C 1 - C 6 ) alkyl sulfonyl group; (n13) halo (C 1 - C 6 ) alkyl group; (n14) halo (C 1 - C 6 ) alkoxy group; (n15) halo (C 3 - C 6 ) cycloalkyl group; (n16) halo (C 1 - C 6 ) alkylsulfanyl group; (n17) halo (C 1 - C 6 ) alkyl sulfinyl group; (n18) halo (C 1 - C 6 ) Alkylsulfonyl group; (n19) (C 1 - C 6 ) alkylcarbonylamino group; (n20) Halo (C 1 - C 6 ) alkylcarbonylamino group; (n21) (C 1 - C 6 ) alkylsulfonylamino group Group; (n22) Halo(C 1 -C 6 )alkylsulfonylamino group; (n23) (C 1 -C 6 ) alkoxycarbonyl group; (n24) N-(C 1 -C 6 )alkylaminocarbonyl group; ( n25) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkyl groups may be the same or different); (n26) N-halo(C 1 -C 6 ) alkylaminocarbonyl group; (n27) phenyl group; (n28) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkyl Substituted phenyl group having 1 to 5 substituents on the ring each independently selected from the group consisting of C 1 - C 6 alkoxy groups; (n29) pyrazolyl group; (n30) halogen atom, each independently from the group consisting of a cyano group, a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group, a halo(C 1 -C 6 )alkyl group and a halo(C 1 -C 6 )alkoxy group; Substituted pyrazolyl group having 1 to 3 substituents selected on the ring; (n31) Phenoxy group; (n32) Halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) Substituted phenoxy having 1 to 5 substituents on the ring, each independently selected from the group consisting of an alkoxy group, a halo(C 1 -C 6 )alkyl group, and a halo(C 1 -C 6 )alkoxy group Group; (n33) Substituted with 1 or 2 substituents selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group formed by two adjacent substituents taken together. optional methylenedioxy group; (n34) N-(C 1 -C 6 )alkylaminosulfonyl group; and (n35) N,N-di(C 1 -C 6 )alkylaminosulfonyl group (the (C 1 -C 6 )alkyl may be the same or different).
However, R 1 's (a45) substituted phenyl group, (a47) substituted pyridyl group, (a49) substituted pyridazinyl group, (a51) substituted pyrazinyl group, (a53) substituted pyrimidinyl group, (a55) substituted oxazolyl group, (a57) Substituted isoxazolyl group, (a59) substituted thienyl group, (a61) substituted thiazolyl group, (a63) substituted isothiazolyl group, (a65) substituted thiadiazolyl group, (a67) substituted pyrazolyl group, (a69) substituted triazolyl group, (a71) substituted Tetrazolyl group and (a73) substituted benzothiazolyl group have a (C 1 -C 6 )alkylsulfonyl group or a halo(C 1 -C 6 )alkylsulfonyl group on the atom adjacent to the atom bonded to the azepane-2,4-dione ring. , N-(C 1 -C 6 )alkylaminosulfonyl group, or N,N-di(C 1 -C 6 )alkylaminosulfonyl group is not substituted.
} or its salts,
[2]R1が、
(a1) 水素原子;(a2) (C1-C6)アルキル基;(a3) (C2-C6)アルケニル基;(a4) (C2-C6)アルキニル基;(a5) (C3-C6)シクロアルキル基;(a6) ハロ(C1-C6)アルキル基;(a10) 置換基群Aからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C1-C6)アルキル基;(a12) (C1-C6)アルコキシカルボニル基;(a14) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(a15) フェニルアミノカルボニル基;(a16) フェニル(C1-C6)アルキル基;(a17) 置換基群Cからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基;(a18) ピリジル(C1-C6)アルキル基;(a19) 置換基群Cからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル(C1-C6)アルキル基;(a24) ピリミジニル(C1-C6)アルキル基;(a25) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル(C1-C6)アルキル基;(a26) オキサゾリル(C1-C6)アルキル基;(a27) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル(C1-C6)アルキル基;(a36) チアジアゾリル(C1-C6)アルキル基;(a37) 置換基群Cから選択される1個の置換基を環上に有する置換チアジアゾリル(C1-C6)アルキル基;(a40) トリアゾリル(C1-C6)アルキル基;(a41) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル(C1-C6)アルキル基;(a44) フェニル基;(a45) 置換基群Dからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(a46) ピリジル基;(a47) 置換基群Dからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(a50) ピラジニル基;(a51) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル基;(a52) ピリミジニル基;(a53) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(a54) オキサゾリル基;(a55) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル基;(a60) チアゾリル基;(a61) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(a64) チアジアゾリル基;(a65) 置換基群Dから選択される1個の置換基を環上に有する置換チアジアゾリル基;(a66) ピラゾリル基;(a67) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(a68) トリアゾリル基;(a69) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル基;(a72) ベンゾチアゾリル基;又は(a73) 置換基群Dから選択される1乃至4個の置換基を環上に有する置換ベンゾチアゾリル基であり、
R2aが、(b1) 水素原子であり、
R2bが、(c1) 水素原子であり、
R3aが、
(d1) 水素原子;(d2) (C1-C6)アルキル基;(d3) フェニル基;又は(d4) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基であり、
R3bが、
(e1) 水素原子;又は(e2) (C1-C6)アルキル基であり、
R4aが、
(f1) 水素原子;又は(f2) (C1-C6)アルキル基であり、
R4bが、
(g1) 水素原子;又は(g2) (C1-C6)アルキル基であり、
R5が、
(h1) (C1-C6)アルキル基;(h3) (C2-C6)アルキニル基;(h4) (C3-C6)シクロアルキル基;(h5) ハロ(C1-C6)アルキル基;(h11) フェニル基;(h12) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(h13) ピリジル基;(h14) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(h15) ピリダジニル基;(h16) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル基;(h17) ピリミジニル基;(h18) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(h19) ピラジニル基;(h20) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル基;(h25) オキサゾリル基;(h26) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル基;(h27) イソキサゾリル基;(h28) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル基;(h31) チアゾリル基;(h32) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(h41) テトラゾリル基;(h42) 置換基群Eから選択される1個の置換基を環上に有する置換テトラゾリル基;(h53) フェニル(C1-C6)アルキル基;又は(h54) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基であり、
R6が、
(i1) 水素原子;又は(i2) (C1-C6)アルキル基であり、
Xが、ヒドロキシル基、(C1-C6)アルコキシ基、(C1-C6)アルキルスルファニル基、(C1-C6)アルキルスルフィニル基、又は(C1-C6)アルキルスルホニル基であり、
Yが、酸素原子、硫黄原子、又はNR7基(式中、R7は、ハロゲン原子、シアノ基、(C1-C6)アルキル基、及びハロ(C1-C6)アルキル基からなる群からそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基を示す。)であり、
置換基群Aが、
(j1) シアノ基;(j5) (C3-C6)シクロアルキル基;(j6) (C1-C6)アルコキシ基;(j7) (C1-C6)アルキルスルファニル基;(j8) (C1-C6)アルキルスルフィニル基;(j9) (C1-C6)アルキルスルホニル基;及び(j18) (C1-C6)アルコキシカルボニル基からなり、
置換基群Cが、
(l1) ハロゲン原子;(l2) シアノ基;(l3) ニトロ基;(l6) (C1-C6)アルキル基;(l9) (C1-C6)アルコキシ基;(l11) (C1-C6)アルキルスルファニル基;(l12) (C1-C6)アルキルスルフィニル基;(l13) (C1-C6)アルキルスルホニル基;(l14) ハロ(C1-C6)アルキル基;(l17) ハロ(C1-C6)アルコキシ基;(l19) ハロ(C1-C6)アルキルスルファニル基;(l20) ハロ(C1-C6)アルキルスルフィニル基;(l21) ハロ(C1-C6)アルキルスルホニル基;(l23) (C1-C6)アルコキシカルボニル基;(l24) (C1-C6)アルキルカルボニルアミノ基;(l25) ハロ(C1-C6)アルキルカルボニルアミノ基;(l26) (C1-C6)アルキルスルホニルアミノ基;(l27) ハロ(C1-C6)アルキルスルホニルアミノ基;(l28) N‐(C1-C6)アルキルアミノカルボニル基;(l29) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);及び(l30) N‐ハロ(C1-C6)アルキルアミノカルボニル基からなり、
置換基群Dが、
(m1) ハロゲン原子;(m2) シアノ基;(m3) ニトロ基;(m7) (C1-C6)アルキル基;(m10) (C1-C6)アルコキシ基;(m12) (C1-C6)アルキルスルファニル基;(m13) (C1-C6)アルキルスルフィニル基;(m14) (C1-C6)アルキルスルホニル基;(m15) ハロ(C1-C6)アルキル基;(m18) ハロ(C1-C6)アルコキシ基;(m20) ハロ(C1-C6)アルキルスルファニル基;(m21) ハロ(C1-C6)アルキルスルフィニル基;(m22) ハロ(C1-C6)アルキルスルホニル基;(m26) (C1-C6)アルキルカルボニルアミノ基;(m27) ハロ(C1-C6)アルキルカルボニルアミノ基;(m28) (C1-C6)アルキルスルホニルアミノ基;(m29) ハロ(C1-C6)アルキルスルホニルアミノ基;(m30) (C1-C6)アルコキシカルボニル基;(m31) N‐(C1-C6)アルキルアミノカルボニル基;(m32) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(m33) N‐ハロ(C1-C6)アルキルアミノカルボニル基;及び(m36) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基からなり、
置換基群Eが、
(n1) ハロゲン原子;(n2) シアノ基;(n3) ニトロ基;(n7) (C1-C6)アルキル基;(n8) (C1-C6)アルコキシ基;(n9) (C3-C6)シクロアルキル基;(n10) (C1-C6)アルキルスルファニル基;(n11) (C1-C6)アルキルスルフィニル基;(n12) (C1-C6)アルキルスルホニル基;(n13) ハロ(C1-C6)アルキル基;(n14) ハロ(C1-C6)アルコキシ基;(n16) ハロ(C1-C6)アルキルスルファニル基;(n17) ハロ(C1-C6)アルキルスルフィニル基;(n18) ハロ(C1-C6)アルキルスルホニル基;(n19) (C1-C6)アルキルカルボニルアミノ基;(n20) ハロ(C1-C6)アルキルカルボニルアミノ基;(n21) (C1-C6)アルキルスルホニルアミノ基;(n22) ハロ(C1-C6)アルキルスルホニルアミノ基;(n23) (C1-C6)アルコキシカルボニル基;(n24) N‐(C1-C6)アルキルアミノカルボニル基;(n25) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(n26) N‐ハロ(C1-C6)アルキルアミノカルボニル基;(n27) フェニル基;(n28) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(n29) ピラゾリル基;(n30) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(n31) フェノキシ基;(n32) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェノキシ基;(n33) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基;(n34) N‐(C1-C6)アルキルアミノスルホニル基;及び(n35) N,N‐ジ(C1-C6)アルキルアミノスルホニル基(当該(C1-C6)アルキルは、同一又は異なってもよい)からなる、[1]に記載の化合物又はその塩類、 [2] R 1 is
(a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 -C 6 )cycloalkyl group; (a6) halo(C 1 -C 6 )alkyl group; (a10) substituted group having 1 to 3 substituents each independently selected from substituent group A (C 1 -C 6 ) alkyl group; (a12) (C 1 -C 6 ) alkoxycarbonyl group; (a14) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 ) alkyl group may be the same or different); (a15) phenylaminocarbonyl group; (a16) phenyl (C 1 -C 6 ) alkyl group; (a17) 1 to 5 groups each independently selected from substituent group C Substituted phenyl (C 1 -C 6 ) alkyl group having a substituent on the ring; (a18) Pyridyl (C 1 -C 6 ) alkyl group; (a19) 1 to 1 each independently selected from substituent group C; Substituted pyridyl (C 1 -C 6 ) alkyl group having 4 substituents on the ring; (a24) Pyrimidinyl (C 1 -C 6 ) alkyl group; (a25) each independently selected from substituent group C Substituted pyrimidinyl (C 1 -C 6 ) alkyl group having 1 to 3 substituents on the ring; (a26) Oxazolyl (C 1 -C 6 ) alkyl group; (a27) each independently selected from substituent group C a substituted oxazolyl (C 1 -C 6 ) alkyl group having 1 or 2 substituents on the ring; (a36) a thiadiazolyl (C 1 -C 6 ) alkyl group; (a37) a substituted oxazolyl (C 1 -C 6 ) alkyl group selected from substituent group C; a substituted thiadiazolyl (C 1 -C 6 ) alkyl group having one substituent on the ring; (a40) a triazolyl (C 1 -C 6 ) alkyl group; (a41) each independently selected from substituent group C; a substituted triazolyl (C 1 -C 6 ) alkyl group having 1 to 2 substituents on the ring; (a44) a phenyl group; (a45) 1 to 5 substituents each independently selected from substituent group D; Substituted phenyl group having a substituent on the ring; (a46) Pyridyl group; (a47) Substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from substituent group D; (a50) Pyrazinyl group; (a51) substituted pyrazinyl group having 1 to 3 substituents on the ring each independently selected from substituent group D; (a52) pyrimidinyl group; (a53) each independently from substituent group D Substituted pyrimidinyl group having 1 to 3 selected substituents on the ring; (a54) Oxazolyl group; (a55) 1 to 2 substituents each independently selected from Substituent Group D on the ring (a60) a thiazolyl group; (a61) a substituted thiazolyl group having on its ring one or two substituents each independently selected from substituent group D; (a64) a thiadiazolyl group; (a65) Substituted thiadiazolyl group having one substituent selected from substituent group D on the ring; (a66) Pyrazolyl group; (a67) Substituted thiadiazolyl group having one to three substituents each independently selected from substituent group D Substituted pyrazolyl group having on the ring; (a68) Triazolyl group; (a69) Substituted triazolyl group having 1 or 2 substituents each independently selected from Substituent Group D on the ring; (a72) Benzothiazolyl group; or (a73) a substituted benzothiazolyl group having 1 to 4 substituents selected from substituent group D on the ring;
R 2a is (b1) a hydrogen atom,
R 2b is (c1) a hydrogen atom,
R 3a is
(d1) Hydrogen atom; (d2) (C 1 -C 6 ) alkyl group; (d3) Phenyl group; or (d4) Halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) Substituted phenyl having 1 to 5 substituents on the ring, each independently selected from the group consisting of an alkoxy group, a halo(C 1 -C 6 )alkyl group, and a halo(C 1 -C 6 )alkoxy group is the basis,
R 3b is
(e1) a hydrogen atom; or (e2) a (C 1 -C 6 ) alkyl group,
R 4a is
(f1) a hydrogen atom; or (f2) a (C 1 -C 6 ) alkyl group,
R 4b is
(g1) a hydrogen atom; or (g2) a (C 1 -C 6 ) alkyl group;
R5 is
(h1) (C 1 -C 6 ) alkyl group; (h3) (C 2 -C 6 ) alkynyl group; (h4) (C 3 -C 6 ) cycloalkyl group; (h5) halo (C 1 -C 6 ) ) Alkyl group; (h11) phenyl group; (h12) substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from substituent group E; (h13) pyridyl group; (h14) substituted Substituted pyridyl group having 1 to 4 substituents each independently selected from group E on the ring; (h15) Pyridazinyl group; (h16) 1 to 3 substituents each independently selected from substituent group E Substituted pyrimidinyl group having on the ring a substituent; (h17) Pyrimidinyl group; (h18) Substituted pyrimidinyl group having 1 to 3 substituents on the ring, each independently selected from substituent group E; (h19) ) Pyrazinyl group; (h20) Substituted pyrazinyl group having 1 to 3 substituents on the ring each independently selected from substituent group E; (h25) oxazolyl group; (h26) each independently from substituent group E Substituted oxazolyl group having 1 to 2 substituents selected on the ring; (h27) Isoxazolyl group; (h31) a thiazolyl group; (h32) a substituted thiazolyl group having on its ring one or two substituents each independently selected from substituent group E; (h41) a tetrazolyl group; (h42) ) Substituted tetrazolyl group having one substituent selected from substituent group E on the ring; (h53) phenyl (C 1 - C 6 ) alkyl group; or (h54) each independently selected from substituent group E a substituted phenyl (C 1 -C 6 ) alkyl group having 1 to 5 substituents on the ring,
R 6 is
(i1) a hydrogen atom; or (i2) a (C 1 -C 6 ) alkyl group;
X is a hydroxyl group, a (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 )alkylsulfanyl group, a (C 1 -C 6 )alkylsulfinyl group, or a (C 1 -C 6 )alkylsulfonyl group; can be,
Y is an oxygen atom, a sulfur atom, or a NR 7 group (wherein R 7 is a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, and a halo(C 1 -C 6 ) alkyl group) represents a substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from the group.
Substituent group A is
(j1) Cyano group; (j5) (C 3 - C 6 ) cycloalkyl group; (j6) (C 1 - C 6 ) alkoxy group; (j7) (C 1 - C 6 ) alkylsulfanyl group; (j8) (C 1 -C 6 )alkylsulfinyl group; (j9) (C 1 -C 6 )alkylsulfonyl group; and (j18) (C 1 -C 6 )alkoxycarbonyl group,
Substituent group C is
(l1) Halogen atom; (l2) Cyano group; (l3) Nitro group; (l6) (C 1 -C 6 ) alkyl group; (l9) (C 1 -C 6 ) alkoxy group; (l11) (C 1 -C 6 ) alkylsulfanyl group; (l12) (C 1 -C 6 ) alkylsulfinyl group; (l13) (C 1 -C 6 ) alkylsulfonyl group; (l14) halo(C 1 -C 6 ) alkyl group; (l17) Halo(C 1 -C 6 )alkoxy group; (l19) Halo(C 1 -C 6 )alkylsulfanyl group; (l20) Halo(C 1 -C 6 )alkylsulfinyl group; (l21) Halo(C 1 - C 6 ) alkylsulfonyl group; (l23) (C 1 - C 6 ) alkoxycarbonyl group; (l24) (C 1 - C 6 ) alkylcarbonylamino group; (l25) halo(C 1 -C 6 ) alkyl Carbonylamino group; (l26) (C 1 - C 6 ) alkylsulfonylamino group; (l27) Halo (C 1 - C 6 ) alkylsulfonylamino group; (l28) N-(C 1 -C 6 ) alkylaminocarbonyl group; (l29) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkyl groups may be the same or different); and (l30) N-halo(C 1 -C 6 )alkylaminocarbonyl group,
The substituent group D is
(m1) Halogen atom; (m2) Cyano group; (m3) Nitro group; (m7) (C 1 - C 6 ) alkyl group; (m10) (C 1 - C 6 ) alkoxy group; (m12) (C 1 -C 6 ) alkylsulfanyl group; (m13) (C 1 -C 6 ) alkylsulfinyl group; (m14) (C 1 -C 6 ) alkylsulfonyl group; (m15) halo(C 1 -C 6 ) alkyl group; (m18) Halo(C 1 -C 6 )alkoxy group; (m20) Halo(C 1 -C 6 )alkylsulfanyl group; (m21) Halo(C 1 -C 6 )alkylsulfinyl group; (m22) Halo(C 1 - C 6 ) alkylsulfonyl group; (m26) (C 1 - C 6 ) alkylcarbonylamino group; (m27) halo (C 1 - C 6 ) alkylcarbonylamino group; (m28) (C 1 - C 6 ) Alkylsulfonylamino group; (m29) Halo(C 1 -C 6 )alkylsulfonylamino group; (m30) (C 1 -C 6 ) alkoxycarbonyl group; (m31) N-(C 1 -C 6 )alkylaminocarbonyl Group; (m32) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 ) alkyls may be the same or different); (m33) N-halo(C 1 -C 6 ) alkylaminocarbonyl group; and (m36) 1 to 1 selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group formed by two adjacent substituents together; Consists of a methylenedioxy group which may be substituted with two substituents,
The substituent group E is
(n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n7) (C 1 - C 6 ) alkyl group; (n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 -C 6 ) cycloalkyl group; (n10) (C 1 -C 6 ) alkylsulfanyl group; (n11) (C 1 -C 6 ) alkylsulfinyl group; (n12) (C 1 -C 6 ) alkylsulfonyl group; (n13) Halo (C 1 - C 6 ) alkyl group; (n14) Halo (C 1 - C 6 ) alkoxy group; (n16) Halo (C 1 - C 6 ) alkylsulfanyl group; (n17) Halo (C 1 -C 6 ) alkylsulfinyl group; (n18) halo(C 1 -C 6 )alkylsulfonyl group; (n19) (C 1 -C 6 ) alkylcarbonylamino group; (n20) halo(C 1 -C 6 ) alkyl Carbonylamino group; (n21) (C 1 - C 6 ) alkylsulfonylamino group; (n22) Halo (C 1 - C 6 ) alkylsulfonylamino group; (n23) (C 1 - C 6 ) alkoxycarbonyl group; ( n24) N-(C 1 -C 6 )alkylaminocarbonyl group; (n25) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkyl groups may be the same or different) (n26) N-halo(C 1 -C 6 )alkylaminocarbonyl group; (n27) Phenyl group; (n28) Halogen atom, cyano group, (C 1 -C 6 )alkyl group, (C 1 to 5 substituents each independently selected from the group consisting of a 1 -C 6 ) alkoxy group, a halo (C 1 -C 6 ) alkyl group, and a halo (C 1 -C 6 ) alkoxy group on the ring; Substituted phenyl group having; (n29) pyrazolyl group; (n30) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkyl group and a substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halo(C 1 -C 6 )alkoxy group; (n31) a phenoxy group; (n32) a halogen atom, a cyano atom; each independently from the group consisting of a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group, a halo(C 1 -C 6 )alkyl group and a halo(C 1 -C 6 )alkoxy group; Substituted phenoxy group having 1 to 5 selected substituents on the ring; (n33) Halogen atom and (C 1 -C 6 ) alkyl group formed by two adjacent substituents together a methylenedioxy group which may be substituted with one or two substituents selected from the group consisting of; (n34) N-(C 1 -C 6 ) alkylaminosulfonyl group; and (n35) N,N- The compound or salt thereof according to [1], consisting of a di(C 1 -C 6 )alkylaminosulfonyl group (the (C 1 -C 6 )alkyl may be the same or different);
(a1) 水素原子;(a2) (C1-C6)アルキル基;(a3) (C2-C6)アルケニル基;(a4) (C2-C6)アルキニル基;(a5) (C3-C6)シクロアルキル基;(a6) ハロ(C1-C6)アルキル基;(a10) 置換基群Aからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C1-C6)アルキル基;(a12) (C1-C6)アルコキシカルボニル基;(a14) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(a15) フェニルアミノカルボニル基;(a16) フェニル(C1-C6)アルキル基;(a17) 置換基群Cからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基;(a18) ピリジル(C1-C6)アルキル基;(a19) 置換基群Cからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル(C1-C6)アルキル基;(a24) ピリミジニル(C1-C6)アルキル基;(a25) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル(C1-C6)アルキル基;(a26) オキサゾリル(C1-C6)アルキル基;(a27) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル(C1-C6)アルキル基;(a36) チアジアゾリル(C1-C6)アルキル基;(a37) 置換基群Cから選択される1個の置換基を環上に有する置換チアジアゾリル(C1-C6)アルキル基;(a40) トリアゾリル(C1-C6)アルキル基;(a41) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル(C1-C6)アルキル基;(a44) フェニル基;(a45) 置換基群Dからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(a46) ピリジル基;(a47) 置換基群Dからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(a50) ピラジニル基;(a51) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル基;(a52) ピリミジニル基;(a53) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(a54) オキサゾリル基;(a55) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル基;(a60) チアゾリル基;(a61) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(a64) チアジアゾリル基;(a65) 置換基群Dから選択される1個の置換基を環上に有する置換チアジアゾリル基;(a66) ピラゾリル基;(a67) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(a68) トリアゾリル基;(a69) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル基;(a72) ベンゾチアゾリル基;又は(a73) 置換基群Dから選択される1乃至4個の置換基を環上に有する置換ベンゾチアゾリル基であり、
R2aが、(b1) 水素原子であり、
R2bが、(c1) 水素原子であり、
R3aが、
(d1) 水素原子;(d2) (C1-C6)アルキル基;(d3) フェニル基;又は(d4) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基であり、
R3bが、
(e1) 水素原子;又は(e2) (C1-C6)アルキル基であり、
R4aが、
(f1) 水素原子;又は(f2) (C1-C6)アルキル基であり、
R4bが、
(g1) 水素原子;又は(g2) (C1-C6)アルキル基であり、
R5が、
(h1) (C1-C6)アルキル基;(h3) (C2-C6)アルキニル基;(h4) (C3-C6)シクロアルキル基;(h5) ハロ(C1-C6)アルキル基;(h11) フェニル基;(h12) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(h13) ピリジル基;(h14) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(h15) ピリダジニル基;(h16) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル基;(h17) ピリミジニル基;(h18) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(h19) ピラジニル基;(h20) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル基;(h25) オキサゾリル基;(h26) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル基;(h27) イソキサゾリル基;(h28) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル基;(h31) チアゾリル基;(h32) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(h41) テトラゾリル基;(h42) 置換基群Eから選択される1個の置換基を環上に有する置換テトラゾリル基;(h53) フェニル(C1-C6)アルキル基;又は(h54) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基であり、
R6が、
(i1) 水素原子;又は(i2) (C1-C6)アルキル基であり、
Xが、ヒドロキシル基、(C1-C6)アルコキシ基、(C1-C6)アルキルスルファニル基、(C1-C6)アルキルスルフィニル基、又は(C1-C6)アルキルスルホニル基であり、
Yが、酸素原子、硫黄原子、又はNR7基(式中、R7は、ハロゲン原子、シアノ基、(C1-C6)アルキル基、及びハロ(C1-C6)アルキル基からなる群からそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基を示す。)であり、
置換基群Aが、
(j1) シアノ基;(j5) (C3-C6)シクロアルキル基;(j6) (C1-C6)アルコキシ基;(j7) (C1-C6)アルキルスルファニル基;(j8) (C1-C6)アルキルスルフィニル基;(j9) (C1-C6)アルキルスルホニル基;及び(j18) (C1-C6)アルコキシカルボニル基からなり、
置換基群Cが、
(l1) ハロゲン原子;(l2) シアノ基;(l3) ニトロ基;(l6) (C1-C6)アルキル基;(l9) (C1-C6)アルコキシ基;(l11) (C1-C6)アルキルスルファニル基;(l12) (C1-C6)アルキルスルフィニル基;(l13) (C1-C6)アルキルスルホニル基;(l14) ハロ(C1-C6)アルキル基;(l17) ハロ(C1-C6)アルコキシ基;(l19) ハロ(C1-C6)アルキルスルファニル基;(l20) ハロ(C1-C6)アルキルスルフィニル基;(l21) ハロ(C1-C6)アルキルスルホニル基;(l23) (C1-C6)アルコキシカルボニル基;(l24) (C1-C6)アルキルカルボニルアミノ基;(l25) ハロ(C1-C6)アルキルカルボニルアミノ基;(l26) (C1-C6)アルキルスルホニルアミノ基;(l27) ハロ(C1-C6)アルキルスルホニルアミノ基;(l28) N‐(C1-C6)アルキルアミノカルボニル基;(l29) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);及び(l30) N‐ハロ(C1-C6)アルキルアミノカルボニル基からなり、
置換基群Dが、
(m1) ハロゲン原子;(m2) シアノ基;(m3) ニトロ基;(m7) (C1-C6)アルキル基;(m10) (C1-C6)アルコキシ基;(m12) (C1-C6)アルキルスルファニル基;(m13) (C1-C6)アルキルスルフィニル基;(m14) (C1-C6)アルキルスルホニル基;(m15) ハロ(C1-C6)アルキル基;(m18) ハロ(C1-C6)アルコキシ基;(m20) ハロ(C1-C6)アルキルスルファニル基;(m21) ハロ(C1-C6)アルキルスルフィニル基;(m22) ハロ(C1-C6)アルキルスルホニル基;(m26) (C1-C6)アルキルカルボニルアミノ基;(m27) ハロ(C1-C6)アルキルカルボニルアミノ基;(m28) (C1-C6)アルキルスルホニルアミノ基;(m29) ハロ(C1-C6)アルキルスルホニルアミノ基;(m30) (C1-C6)アルコキシカルボニル基;(m31) N‐(C1-C6)アルキルアミノカルボニル基;(m32) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(m33) N‐ハロ(C1-C6)アルキルアミノカルボニル基;及び(m36) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基からなり、
置換基群Eが、
(n1) ハロゲン原子;(n2) シアノ基;(n3) ニトロ基;(n7) (C1-C6)アルキル基;(n8) (C1-C6)アルコキシ基;(n9) (C3-C6)シクロアルキル基;(n10) (C1-C6)アルキルスルファニル基;(n11) (C1-C6)アルキルスルフィニル基;(n12) (C1-C6)アルキルスルホニル基;(n13) ハロ(C1-C6)アルキル基;(n14) ハロ(C1-C6)アルコキシ基;(n16) ハロ(C1-C6)アルキルスルファニル基;(n17) ハロ(C1-C6)アルキルスルフィニル基;(n18) ハロ(C1-C6)アルキルスルホニル基;(n19) (C1-C6)アルキルカルボニルアミノ基;(n20) ハロ(C1-C6)アルキルカルボニルアミノ基;(n21) (C1-C6)アルキルスルホニルアミノ基;(n22) ハロ(C1-C6)アルキルスルホニルアミノ基;(n23) (C1-C6)アルコキシカルボニル基;(n24) N‐(C1-C6)アルキルアミノカルボニル基;(n25) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(n26) N‐ハロ(C1-C6)アルキルアミノカルボニル基;(n27) フェニル基;(n28) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(n29) ピラゾリル基;(n30) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(n31) フェノキシ基;(n32) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェノキシ基;(n33) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基;(n34) N‐(C1-C6)アルキルアミノスルホニル基;及び(n35) N,N‐ジ(C1-C6)アルキルアミノスルホニル基(当該(C1-C6)アルキルは、同一又は異なってもよい)からなる、[1]に記載の化合物又はその塩類、 [2] R 1 is
(a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 -C 6 )cycloalkyl group; (a6) halo(C 1 -C 6 )alkyl group; (a10) substituted group having 1 to 3 substituents each independently selected from substituent group A (C 1 -C 6 ) alkyl group; (a12) (C 1 -C 6 ) alkoxycarbonyl group; (a14) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 ) alkyl group may be the same or different); (a15) phenylaminocarbonyl group; (a16) phenyl (C 1 -C 6 ) alkyl group; (a17) 1 to 5 groups each independently selected from substituent group C Substituted phenyl (C 1 -C 6 ) alkyl group having a substituent on the ring; (a18) Pyridyl (C 1 -C 6 ) alkyl group; (a19) 1 to 1 each independently selected from substituent group C; Substituted pyridyl (C 1 -C 6 ) alkyl group having 4 substituents on the ring; (a24) Pyrimidinyl (C 1 -C 6 ) alkyl group; (a25) each independently selected from substituent group C Substituted pyrimidinyl (C 1 -C 6 ) alkyl group having 1 to 3 substituents on the ring; (a26) Oxazolyl (C 1 -C 6 ) alkyl group; (a27) each independently selected from substituent group C a substituted oxazolyl (C 1 -C 6 ) alkyl group having 1 or 2 substituents on the ring; (a36) a thiadiazolyl (C 1 -C 6 ) alkyl group; (a37) a substituted oxazolyl (C 1 -C 6 ) alkyl group selected from substituent group C; a substituted thiadiazolyl (C 1 -C 6 ) alkyl group having one substituent on the ring; (a40) a triazolyl (C 1 -C 6 ) alkyl group; (a41) each independently selected from substituent group C; a substituted triazolyl (C 1 -C 6 ) alkyl group having 1 to 2 substituents on the ring; (a44) a phenyl group; (a45) 1 to 5 substituents each independently selected from substituent group D; Substituted phenyl group having a substituent on the ring; (a46) Pyridyl group; (a47) Substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from substituent group D; (a50) Pyrazinyl group; (a51) substituted pyrazinyl group having 1 to 3 substituents on the ring each independently selected from substituent group D; (a52) pyrimidinyl group; (a53) each independently from substituent group D Substituted pyrimidinyl group having 1 to 3 selected substituents on the ring; (a54) Oxazolyl group; (a55) 1 to 2 substituents each independently selected from Substituent Group D on the ring (a60) a thiazolyl group; (a61) a substituted thiazolyl group having on its ring one or two substituents each independently selected from substituent group D; (a64) a thiadiazolyl group; (a65) Substituted thiadiazolyl group having one substituent selected from substituent group D on the ring; (a66) Pyrazolyl group; (a67) Substituted thiadiazolyl group having one to three substituents each independently selected from substituent group D Substituted pyrazolyl group having on the ring; (a68) Triazolyl group; (a69) Substituted triazolyl group having 1 or 2 substituents each independently selected from Substituent Group D on the ring; (a72) Benzothiazolyl group; or (a73) a substituted benzothiazolyl group having 1 to 4 substituents selected from substituent group D on the ring;
R 2a is (b1) a hydrogen atom,
R 2b is (c1) a hydrogen atom,
R 3a is
(d1) Hydrogen atom; (d2) (C 1 -C 6 ) alkyl group; (d3) Phenyl group; or (d4) Halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) Substituted phenyl having 1 to 5 substituents on the ring, each independently selected from the group consisting of an alkoxy group, a halo(C 1 -C 6 )alkyl group, and a halo(C 1 -C 6 )alkoxy group is the basis,
R 3b is
(e1) a hydrogen atom; or (e2) a (C 1 -C 6 ) alkyl group,
R 4a is
(f1) a hydrogen atom; or (f2) a (C 1 -C 6 ) alkyl group,
R 4b is
(g1) a hydrogen atom; or (g2) a (C 1 -C 6 ) alkyl group;
R5 is
(h1) (C 1 -C 6 ) alkyl group; (h3) (C 2 -C 6 ) alkynyl group; (h4) (C 3 -C 6 ) cycloalkyl group; (h5) halo (C 1 -C 6 ) ) Alkyl group; (h11) phenyl group; (h12) substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from substituent group E; (h13) pyridyl group; (h14) substituted Substituted pyridyl group having 1 to 4 substituents each independently selected from group E on the ring; (h15) Pyridazinyl group; (h16) 1 to 3 substituents each independently selected from substituent group E Substituted pyrimidinyl group having on the ring a substituent; (h17) Pyrimidinyl group; (h18) Substituted pyrimidinyl group having 1 to 3 substituents on the ring, each independently selected from substituent group E; (h19) ) Pyrazinyl group; (h20) Substituted pyrazinyl group having 1 to 3 substituents on the ring each independently selected from substituent group E; (h25) oxazolyl group; (h26) each independently from substituent group E Substituted oxazolyl group having 1 to 2 substituents selected on the ring; (h27) Isoxazolyl group; (h31) a thiazolyl group; (h32) a substituted thiazolyl group having on its ring one or two substituents each independently selected from substituent group E; (h41) a tetrazolyl group; (h42) ) Substituted tetrazolyl group having one substituent selected from substituent group E on the ring; (h53) phenyl (C 1 - C 6 ) alkyl group; or (h54) each independently selected from substituent group E a substituted phenyl (C 1 -C 6 ) alkyl group having 1 to 5 substituents on the ring,
R 6 is
(i1) a hydrogen atom; or (i2) a (C 1 -C 6 ) alkyl group;
X is a hydroxyl group, a (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 )alkylsulfanyl group, a (C 1 -C 6 )alkylsulfinyl group, or a (C 1 -C 6 )alkylsulfonyl group; can be,
Y is an oxygen atom, a sulfur atom, or a NR 7 group (wherein R 7 is a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, and a halo(C 1 -C 6 ) alkyl group) represents a substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from the group.
Substituent group A is
(j1) Cyano group; (j5) (C 3 - C 6 ) cycloalkyl group; (j6) (C 1 - C 6 ) alkoxy group; (j7) (C 1 - C 6 ) alkylsulfanyl group; (j8) (C 1 -C 6 )alkylsulfinyl group; (j9) (C 1 -C 6 )alkylsulfonyl group; and (j18) (C 1 -C 6 )alkoxycarbonyl group,
Substituent group C is
(l1) Halogen atom; (l2) Cyano group; (l3) Nitro group; (l6) (C 1 -C 6 ) alkyl group; (l9) (C 1 -C 6 ) alkoxy group; (l11) (C 1 -C 6 ) alkylsulfanyl group; (l12) (C 1 -C 6 ) alkylsulfinyl group; (l13) (C 1 -C 6 ) alkylsulfonyl group; (l14) halo(C 1 -C 6 ) alkyl group; (l17) Halo(C 1 -C 6 )alkoxy group; (l19) Halo(C 1 -C 6 )alkylsulfanyl group; (l20) Halo(C 1 -C 6 )alkylsulfinyl group; (l21) Halo(C 1 - C 6 ) alkylsulfonyl group; (l23) (C 1 - C 6 ) alkoxycarbonyl group; (l24) (C 1 - C 6 ) alkylcarbonylamino group; (l25) halo(C 1 -C 6 ) alkyl Carbonylamino group; (l26) (C 1 - C 6 ) alkylsulfonylamino group; (l27) Halo (C 1 - C 6 ) alkylsulfonylamino group; (l28) N-(C 1 -C 6 ) alkylaminocarbonyl group; (l29) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkyl groups may be the same or different); and (l30) N-halo(C 1 -C 6 )alkylaminocarbonyl group,
The substituent group D is
(m1) Halogen atom; (m2) Cyano group; (m3) Nitro group; (m7) (C 1 - C 6 ) alkyl group; (m10) (C 1 - C 6 ) alkoxy group; (m12) (C 1 -C 6 ) alkylsulfanyl group; (m13) (C 1 -C 6 ) alkylsulfinyl group; (m14) (C 1 -C 6 ) alkylsulfonyl group; (m15) halo(C 1 -C 6 ) alkyl group; (m18) Halo(C 1 -C 6 )alkoxy group; (m20) Halo(C 1 -C 6 )alkylsulfanyl group; (m21) Halo(C 1 -C 6 )alkylsulfinyl group; (m22) Halo(C 1 - C 6 ) alkylsulfonyl group; (m26) (C 1 - C 6 ) alkylcarbonylamino group; (m27) halo (C 1 - C 6 ) alkylcarbonylamino group; (m28) (C 1 - C 6 ) Alkylsulfonylamino group; (m29) Halo(C 1 -C 6 )alkylsulfonylamino group; (m30) (C 1 -C 6 ) alkoxycarbonyl group; (m31) N-(C 1 -C 6 )alkylaminocarbonyl Group; (m32) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 ) alkyls may be the same or different); (m33) N-halo(C 1 -C 6 ) alkylaminocarbonyl group; and (m36) 1 to 1 selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group formed by two adjacent substituents together; Consists of a methylenedioxy group which may be substituted with two substituents,
The substituent group E is
(n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n7) (C 1 - C 6 ) alkyl group; (n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 -C 6 ) cycloalkyl group; (n10) (C 1 -C 6 ) alkylsulfanyl group; (n11) (C 1 -C 6 ) alkylsulfinyl group; (n12) (C 1 -C 6 ) alkylsulfonyl group; (n13) Halo (C 1 - C 6 ) alkyl group; (n14) Halo (C 1 - C 6 ) alkoxy group; (n16) Halo (C 1 - C 6 ) alkylsulfanyl group; (n17) Halo (C 1 -C 6 ) alkylsulfinyl group; (n18) halo(C 1 -C 6 )alkylsulfonyl group; (n19) (C 1 -C 6 ) alkylcarbonylamino group; (n20) halo(C 1 -C 6 ) alkyl Carbonylamino group; (n21) (C 1 - C 6 ) alkylsulfonylamino group; (n22) Halo (C 1 - C 6 ) alkylsulfonylamino group; (n23) (C 1 - C 6 ) alkoxycarbonyl group; ( n24) N-(C 1 -C 6 )alkylaminocarbonyl group; (n25) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkyl groups may be the same or different) (n26) N-halo(C 1 -C 6 )alkylaminocarbonyl group; (n27) Phenyl group; (n28) Halogen atom, cyano group, (C 1 -C 6 )alkyl group, (C 1 to 5 substituents each independently selected from the group consisting of a 1 -C 6 ) alkoxy group, a halo (C 1 -C 6 ) alkyl group, and a halo (C 1 -C 6 ) alkoxy group on the ring; Substituted phenyl group having; (n29) pyrazolyl group; (n30) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkyl group and a substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halo(C 1 -C 6 )alkoxy group; (n31) a phenoxy group; (n32) a halogen atom, a cyano atom; each independently from the group consisting of a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group, a halo(C 1 -C 6 )alkyl group and a halo(C 1 -C 6 )alkoxy group; Substituted phenoxy group having 1 to 5 selected substituents on the ring; (n33) Halogen atom and (C 1 -C 6 ) alkyl group formed by two adjacent substituents together a methylenedioxy group which may be substituted with one or two substituents selected from the group consisting of; (n34) N-(C 1 -C 6 ) alkylaminosulfonyl group; and (n35) N,N- The compound or salt thereof according to [1], consisting of a di(C 1 -C 6 )alkylaminosulfonyl group (the (C 1 -C 6 )alkyl may be the same or different);
[3]R1が、
(a1) 水素原子;(a3) (C2-C6)アルケニル基;(a6) ハロ(C1-C6)アルキル基;(a10) 置換基群Aからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C1-C6)アルキル基;(a16) フェニル(C1-C6)アルキル基;(a17) 置換基群Cからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基;(a18) ピリジル(C1-C6)アルキル基;(a44) フェニル基;(a45) 置換基群Dからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(a46) ピリジル基;(a47) 置換基群Dからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(a50) ピラジニル基;(a61) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(a64) チアジアゾリル基;(a67) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(a69) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル基;又は(a72) ベンゾチアゾリル基であり、
R2aが、(b1) 水素原子であり、
R2bが、(c1) 水素原子であり、
R3aが、
(d1) 水素原子;又は(d2) (C1-C6)アルキル基であり、
R3bが、
(e1) 水素原子;又は(e2) (C1-C6)アルキル基であり、
R4aが、(f1) 水素原子であり、
R4bが、(g1) 水素原子であり、
R5が、
(h1) (C1-C6)アルキル基;(h11) フェニル基;(h12) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(h13) ピリジル基;(h14) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(h15) ピリダジニル基;(h16) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル基;(h18) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(h19) ピラジニル基;(h25) オキサゾリル基;(h28) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル基;(h31) チアゾリル基;(h42) 置換基群Eから選択される1個の置換基を環上に有する置換テトラゾリル基;又は(h53) フェニル(C1-C6)アルキル基であり、
R6が、(i1) 水素原子であり、
Xが、ヒドロキシル基であり、
Yが、酸素原子、又は硫黄原子であり、
置換基群Aが、(j5) (C3-C6)シクロアルキル基であり、
置換基群Cが、
(l1) ハロゲン原子;(l2) シアノ基;(l9) (C1-C6)アルコキシ基;(l11) (C1-C6)アルキルスルファニル基;(l14) ハロ(C1-C6)アルキル基;(l17) ハロ(C1-C6)アルコキシ基;(l19) ハロ(C1-C6)アルキルスルファニル基;及び(l20) ハロ(C1-C6)アルキルスルフィニル基からなり、
置換基群Dが、
(m7) (C1-C6)アルキル基;(m15) ハロ(C1-C6)アルキル基;(m18) ハロ(C1-C6)アルコキシ基;(m20) ハロ(C1-C6)アルキルスルファニル基;及び(m36) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基からなり、
置換基群Eが、
(n1) ハロゲン原子;(n2) シアノ基;(n3) ニトロ基;(n7) (C1-C6)アルキル基;(n8) (C1-C6)アルコキシ基;(n9) (C3-C6)シクロアルキル基;(n10) (C1-C6)アルキルスルファニル基;(n12) (C1-C6)アルキルスルホニル基;(n13) ハロ(C1-C6)アルキル基;(n14) ハロ(C1-C6)アルコキシ基;(n19) (C1-C6)アルキルカルボニルアミノ基;(n21) (C1-C6)アルキルスルホニルアミノ基;(n33) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基;及び(n34) N‐(C1-C6)アルキルアミノスルホニル基からなる、[1]に記載の化合物又はその塩類、 [3] R 1 is
(a1) Hydrogen atom; (a3) (C 2 -C 6 ) alkenyl group; (a6) Halo (C 1 -C 6 ) alkyl group; (a10) 1 to 3 each independently selected from substituent group A (a16) a phenyl (C 1 -C 6 ) alkyl group; (a17) a substituted (C 1 -C 6 ) alkyl group having 1 to 5 substituents, each independently selected from substituent group C; Substituted phenyl (C 1 - C 6 ) alkyl group having a substituent on the ring; (a18) Pyridyl (C 1 -C 6 ) alkyl group; (a44) Phenyl group; (a45) Each independently from substituent group D Substituted phenyl group having 1 to 5 selected substituents on the ring; (a46) Pyridyl group; (a47) 1 to 4 substituents independently selected from substituent group D on the ring a substituted pyridyl group; (a50) a pyrazinyl group; (a61) a substituted thiazolyl group having on the ring one or two substituents each independently selected from substituent group D; (a64) a thiadiazolyl group; (a67) Substituted pyrazolyl group having 1 to 3 substituents each independently selected from substituent group D on the ring; (a69) Substituted pyrazolyl group having 1 to 2 substituents each independently selected from substituent group D on the ring or (a72) a benzothiazolyl group,
R 2a is (b1) a hydrogen atom,
R 2b is (c1) a hydrogen atom,
R 3a is
(d1) a hydrogen atom; or (d2) a (C 1 -C 6 ) alkyl group,
R 3b is
(e1) a hydrogen atom; or (e2) a (C 1 -C 6 ) alkyl group,
R 4a is (f1) a hydrogen atom,
R 4b is (g1) a hydrogen atom,
R5 is
(h1) (C 1 -C 6 ) alkyl group; (h11) phenyl group; (h12) substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from substituent group E; h13) Pyridyl group; (h14) Substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from Substituent Group E; (h15) Pyridazinyl group; (h16) Each from Substituent Group E Substituted pyrimidinyl group having 1 to 3 independently selected substituents on the ring; (h18) Substituted pyrimidinyl group having 1 to 3 substituents on the ring, each independently selected from substituent group E ; (h19) pyrazinyl group; (h25) oxazolyl group; (h28) substituted isoxazolyl group having on the ring one or two substituents each independently selected from substituent group E; (h31) thiazolyl group; ( h42) a substituted tetrazolyl group having one substituent selected from substituent group E on the ring; or (h53) a phenyl (C 1 -C 6 ) alkyl group;
R 6 is (i1) a hydrogen atom,
X is a hydroxyl group,
Y is an oxygen atom or a sulfur atom,
Substituent group A is a (j5) (C 3 -C 6 ) cycloalkyl group,
Substituent group C is
(l1) Halogen atom; (l2) Cyano group; (l9) (C 1 - C 6 ) alkoxy group; (l11) (C 1 - C 6 ) alkylsulfanyl group; (l14) Halo (C 1 - C 6 ) Alkyl group; (l17) halo(C 1 -C 6 )alkoxy group; (l19) halo(C 1 -C 6 )alkylsulfanyl group; and (l20) halo(C 1 -C 6 )alkylsulfinyl group,
The substituent group D is
(m7) (C 1 -C 6 ) alkyl group; (m15) halo (C 1 -C 6 ) alkyl group; (m18) halo (C 1 -C 6 ) alkoxy group; (m20) halo (C 1 -C 6 ) Alkylsulfanyl group; and (m36) 1 to 2 selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group formed by two adjacent substituents together. Consists of a methylenedioxy group which may be substituted with a substituent,
The substituent group E is
(n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n7) (C 1 - C 6 ) alkyl group; (n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 -C 6 ) cycloalkyl group; (n10) (C 1 -C 6 ) alkylsulfanyl group; (n12) (C 1 -C 6 ) alkylsulfonyl group; (n13) halo(C 1 -C 6 ) alkyl group; (n14) Halo(C 1 -C 6 )alkoxy group; (n19) (C 1 -C 6 )alkylcarbonylamino group; (n21) (C 1 -C 6 )alkylsulfonylamino group; (n33) Adjacent A methylenedioxy group optionally substituted with 1 to 2 substituents selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group, formed by two substituents taken together; and (n34) the compound or salt thereof according to [1], consisting of an N-(C 1 -C 6 )alkylaminosulfonyl group,
(a1) 水素原子;(a3) (C2-C6)アルケニル基;(a6) ハロ(C1-C6)アルキル基;(a10) 置換基群Aからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C1-C6)アルキル基;(a16) フェニル(C1-C6)アルキル基;(a17) 置換基群Cからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基;(a18) ピリジル(C1-C6)アルキル基;(a44) フェニル基;(a45) 置換基群Dからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(a46) ピリジル基;(a47) 置換基群Dからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(a50) ピラジニル基;(a61) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(a64) チアジアゾリル基;(a67) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(a69) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル基;又は(a72) ベンゾチアゾリル基であり、
R2aが、(b1) 水素原子であり、
R2bが、(c1) 水素原子であり、
R3aが、
(d1) 水素原子;又は(d2) (C1-C6)アルキル基であり、
R3bが、
(e1) 水素原子;又は(e2) (C1-C6)アルキル基であり、
R4aが、(f1) 水素原子であり、
R4bが、(g1) 水素原子であり、
R5が、
(h1) (C1-C6)アルキル基;(h11) フェニル基;(h12) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(h13) ピリジル基;(h14) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(h15) ピリダジニル基;(h16) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル基;(h18) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(h19) ピラジニル基;(h25) オキサゾリル基;(h28) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル基;(h31) チアゾリル基;(h42) 置換基群Eから選択される1個の置換基を環上に有する置換テトラゾリル基;又は(h53) フェニル(C1-C6)アルキル基であり、
R6が、(i1) 水素原子であり、
Xが、ヒドロキシル基であり、
Yが、酸素原子、又は硫黄原子であり、
置換基群Aが、(j5) (C3-C6)シクロアルキル基であり、
置換基群Cが、
(l1) ハロゲン原子;(l2) シアノ基;(l9) (C1-C6)アルコキシ基;(l11) (C1-C6)アルキルスルファニル基;(l14) ハロ(C1-C6)アルキル基;(l17) ハロ(C1-C6)アルコキシ基;(l19) ハロ(C1-C6)アルキルスルファニル基;及び(l20) ハロ(C1-C6)アルキルスルフィニル基からなり、
置換基群Dが、
(m7) (C1-C6)アルキル基;(m15) ハロ(C1-C6)アルキル基;(m18) ハロ(C1-C6)アルコキシ基;(m20) ハロ(C1-C6)アルキルスルファニル基;及び(m36) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基からなり、
置換基群Eが、
(n1) ハロゲン原子;(n2) シアノ基;(n3) ニトロ基;(n7) (C1-C6)アルキル基;(n8) (C1-C6)アルコキシ基;(n9) (C3-C6)シクロアルキル基;(n10) (C1-C6)アルキルスルファニル基;(n12) (C1-C6)アルキルスルホニル基;(n13) ハロ(C1-C6)アルキル基;(n14) ハロ(C1-C6)アルコキシ基;(n19) (C1-C6)アルキルカルボニルアミノ基;(n21) (C1-C6)アルキルスルホニルアミノ基;(n33) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基;及び(n34) N‐(C1-C6)アルキルアミノスルホニル基からなる、[1]に記載の化合物又はその塩類、 [3] R 1 is
(a1) Hydrogen atom; (a3) (C 2 -C 6 ) alkenyl group; (a6) Halo (C 1 -C 6 ) alkyl group; (a10) 1 to 3 each independently selected from substituent group A (a16) a phenyl (C 1 -C 6 ) alkyl group; (a17) a substituted (C 1 -C 6 ) alkyl group having 1 to 5 substituents, each independently selected from substituent group C; Substituted phenyl (C 1 - C 6 ) alkyl group having a substituent on the ring; (a18) Pyridyl (C 1 -C 6 ) alkyl group; (a44) Phenyl group; (a45) Each independently from substituent group D Substituted phenyl group having 1 to 5 selected substituents on the ring; (a46) Pyridyl group; (a47) 1 to 4 substituents independently selected from substituent group D on the ring a substituted pyridyl group; (a50) a pyrazinyl group; (a61) a substituted thiazolyl group having on the ring one or two substituents each independently selected from substituent group D; (a64) a thiadiazolyl group; (a67) Substituted pyrazolyl group having 1 to 3 substituents each independently selected from substituent group D on the ring; (a69) Substituted pyrazolyl group having 1 to 2 substituents each independently selected from substituent group D on the ring or (a72) a benzothiazolyl group,
R 2a is (b1) a hydrogen atom,
R 2b is (c1) a hydrogen atom,
R 3a is
(d1) a hydrogen atom; or (d2) a (C 1 -C 6 ) alkyl group,
R 3b is
(e1) a hydrogen atom; or (e2) a (C 1 -C 6 ) alkyl group,
R 4a is (f1) a hydrogen atom,
R 4b is (g1) a hydrogen atom,
R5 is
(h1) (C 1 -C 6 ) alkyl group; (h11) phenyl group; (h12) substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from substituent group E; h13) Pyridyl group; (h14) Substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from Substituent Group E; (h15) Pyridazinyl group; (h16) Each from Substituent Group E Substituted pyrimidinyl group having 1 to 3 independently selected substituents on the ring; (h18) Substituted pyrimidinyl group having 1 to 3 substituents on the ring, each independently selected from substituent group E ; (h19) pyrazinyl group; (h25) oxazolyl group; (h28) substituted isoxazolyl group having on the ring one or two substituents each independently selected from substituent group E; (h31) thiazolyl group; ( h42) a substituted tetrazolyl group having one substituent selected from substituent group E on the ring; or (h53) a phenyl (C 1 -C 6 ) alkyl group;
R 6 is (i1) a hydrogen atom,
X is a hydroxyl group,
Y is an oxygen atom or a sulfur atom,
Substituent group A is a (j5) (C 3 -C 6 ) cycloalkyl group,
Substituent group C is
(l1) Halogen atom; (l2) Cyano group; (l9) (C 1 - C 6 ) alkoxy group; (l11) (C 1 - C 6 ) alkylsulfanyl group; (l14) Halo (C 1 - C 6 ) Alkyl group; (l17) halo(C 1 -C 6 )alkoxy group; (l19) halo(C 1 -C 6 )alkylsulfanyl group; and (l20) halo(C 1 -C 6 )alkylsulfinyl group,
The substituent group D is
(m7) (C 1 -C 6 ) alkyl group; (m15) halo (C 1 -C 6 ) alkyl group; (m18) halo (C 1 -C 6 ) alkoxy group; (m20) halo (C 1 -C 6 ) Alkylsulfanyl group; and (m36) 1 to 2 selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group formed by two adjacent substituents together. Consists of a methylenedioxy group which may be substituted with a substituent,
The substituent group E is
(n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n7) (C 1 - C 6 ) alkyl group; (n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 -C 6 ) cycloalkyl group; (n10) (C 1 -C 6 ) alkylsulfanyl group; (n12) (C 1 -C 6 ) alkylsulfonyl group; (n13) halo(C 1 -C 6 ) alkyl group; (n14) Halo(C 1 -C 6 )alkoxy group; (n19) (C 1 -C 6 )alkylcarbonylamino group; (n21) (C 1 -C 6 )alkylsulfonylamino group; (n33) Adjacent A methylenedioxy group optionally substituted with 1 to 2 substituents selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group, formed by two substituents taken together; and (n34) the compound or salt thereof according to [1], consisting of an N-(C 1 -C 6 )alkylaminosulfonyl group,
[4][1]乃至[3]の何れか一つに記載の化合物又はその塩類を有効成分として含有することを特徴とする有害生物防除剤、
[5][1]乃至[3]の何れか一つに記載の化合物又はその塩類を有効成分として含有することを特徴とする農園芸用害虫防除剤、
[6][1]乃至[3]の何れか一つに記載の化合物又はその塩類を有効成分として含有することを特徴とする動物用外部寄生虫防除剤、
[7][1]乃至[3]の何れか一つに記載の化合物又はその塩類を有効成分として含有することを特徴とする動物用内部寄生虫防除剤、
[8][5]に記載の農園芸用害虫防除剤の有効量を植物又は土壌に処理することを特徴とする農園芸用害虫の防除方法、
[9][6]に記載の動物用外部寄生虫防除剤の有効量を対象動物に、経口又は非経口投与することを特徴とする動物の外部寄生虫の防除方法、
[10][7]に記載の動物用内部寄生虫防除剤有効量を対象動物に、経口又は非経口投与することを特徴とする動物の内部寄生虫の防除方法、
[11][1]乃至[3]の何れか一つに記載の化合物又はその塩類の有害生物防除剤としての使用、
に関する。 [4] A pest control agent characterized by containing the compound described in any one of [1] to [3] or a salt thereof as an active ingredient,
[5] A pest control agent for agricultural and horticultural purposes, characterized by containing the compound or its salts described in any one of [1] to [3] as an active ingredient;
[6] An animal ectoparasite control agent characterized by containing the compound or salt thereof as an active ingredient according to any one of [1] to [3];
[7] An animal endoparasite control agent characterized by containing the compound or salt thereof as an active ingredient according to any one of [1] to [3];
[8] A method for controlling agricultural and horticultural pests, which comprises applying an effective amount of the agricultural and horticultural pest control agent according to [5] to plants or soil;
[9] A method for controlling animal ectoparasites, which comprises orally or parenterally administering an effective amount of the animal ectoparasiticide according to [6] to a target animal;
[10] A method for controlling endoparasites in animals, which comprises orally or parenterally administering an effective amount of the animal endoparasite control agent according to [7] to a target animal;
[11] Use of the compound or salt thereof according to any one of [1] to [3] as a pest control agent,
Regarding.
[5][1]乃至[3]の何れか一つに記載の化合物又はその塩類を有効成分として含有することを特徴とする農園芸用害虫防除剤、
[6][1]乃至[3]の何れか一つに記載の化合物又はその塩類を有効成分として含有することを特徴とする動物用外部寄生虫防除剤、
[7][1]乃至[3]の何れか一つに記載の化合物又はその塩類を有効成分として含有することを特徴とする動物用内部寄生虫防除剤、
[8][5]に記載の農園芸用害虫防除剤の有効量を植物又は土壌に処理することを特徴とする農園芸用害虫の防除方法、
[9][6]に記載の動物用外部寄生虫防除剤の有効量を対象動物に、経口又は非経口投与することを特徴とする動物の外部寄生虫の防除方法、
[10][7]に記載の動物用内部寄生虫防除剤有効量を対象動物に、経口又は非経口投与することを特徴とする動物の内部寄生虫の防除方法、
[11][1]乃至[3]の何れか一つに記載の化合物又はその塩類の有害生物防除剤としての使用、
に関する。 [4] A pest control agent characterized by containing the compound described in any one of [1] to [3] or a salt thereof as an active ingredient,
[5] A pest control agent for agricultural and horticultural purposes, characterized by containing the compound or its salts described in any one of [1] to [3] as an active ingredient;
[6] An animal ectoparasite control agent characterized by containing the compound or salt thereof as an active ingredient according to any one of [1] to [3];
[7] An animal endoparasite control agent characterized by containing the compound or salt thereof as an active ingredient according to any one of [1] to [3];
[8] A method for controlling agricultural and horticultural pests, which comprises applying an effective amount of the agricultural and horticultural pest control agent according to [5] to plants or soil;
[9] A method for controlling animal ectoparasites, which comprises orally or parenterally administering an effective amount of the animal ectoparasiticide according to [6] to a target animal;
[10] A method for controlling endoparasites in animals, which comprises orally or parenterally administering an effective amount of the animal endoparasite control agent according to [7] to a target animal;
[11] Use of the compound or salt thereof according to any one of [1] to [3] as a pest control agent,
Regarding.
本発明の化合物又はその塩類は有害生物防除剤として優れた効果を有する、一般式(1)で表されるアゼパンジオン誘導体を提供するものである。
The compound or salt thereof of the present invention provides an azepanedione derivative represented by the general formula (1), which has excellent effects as a pest control agent.
本発明化合物の一般式(1)の定義において、「ハロ」とは「ハロゲン原子」を意味し、塩素原子、臭素原子、ヨウ素原子又はフッ素原子を示す。
In the definition of the general formula (1) of the compound of the present invention, "halo" means a "halogen atom" and represents a chlorine atom, a bromine atom, an iodine atom, or a fluorine atom.
「(C1-C6)アルキル基」とは、例えば、メチル基、エチル基、ノルマルプロピル基、イソプロピル基、ノルマルブチル基、イソブチル基、セカンダリーブチル基、ターシャリーブチル基、ノルマルペンチル基、イソペンチル基、ターシャリーペンチル基、ネオペンチル基、2,3‐ジメチルプロピル基、1‐エチルプロピル基、1‐メチルブチル基、2‐メチルブチル基、ノルマルヘキシル基、イソヘキシル基、2‐ヘキシル基、3‐ヘキシル基、2‐メチルペンチル基、3‐メチルペンチル基、1,1,2‐トリメチルプロピル基、3,3‐ジメチルブチル基等の直鎖又は分岐鎖状の炭素原子数1~6個のアルキル基を示す。
"(C 1 -C 6 )alkyl group" means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group. group, tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group , 2-methylpentyl group, 3-methylpentyl group, 1,1,2-trimethylpropyl group, 3,3-dimethylbutyl group, etc. linear or branched alkyl group having 1 to 6 carbon atoms. show.
「(C2-C6)アルケニル基」とは、例えば、ビニル基、アリル基、イソプロペニル基、1‐ブテニル基、2‐ブテニル基、2‐メチル‐2‐プロペニル基、1‐メチル‐2‐プロペニル基、2‐メチル‐1‐プロペニル基、ペンテニル基、1‐ヘキセニル基、3,3‐ジメチル‐1‐ブテニル基等の直鎖又は分鎖状の炭素原子数2~6個のアルケニル基を示し、「(C2-C6)アルキニル基」とは、例えばエチニル基、1‐プロピニル基、2‐プロピニル基、1‐ブチニル基、2‐ブチニル基、3‐ブチニル基、3‐メチル‐1‐プロピニル基、2‐メチル‐3‐プロピニル基、ペンチニル基、1‐ヘキシニル基、3‐メチル‐1‐ブチニル基、3,3‐ジメチル‐1‐ブチニル基等の直鎖又は分鎖状の炭素原子数2~6個のアルキニル基を示す。
"(C 2 -C 6 )alkenyl group" means, for example, vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2 - Straight chain or branched alkenyl group having 2 to 6 carbon atoms such as propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group, 3,3-dimethyl-1-butenyl group, etc. "(C 2 -C 6 )alkynyl group" refers to, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 3-methyl- Straight chain or branched chain such as 1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, 3-methyl-1-butynyl group, 3,3-dimethyl-1-butynyl group Indicates an alkynyl group having 2 to 6 carbon atoms.
「(C3-C6)シクロアルキル基」とは、例えば、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の炭素原子数3~6個の環状のアルキル基を示す。
The term "(C 3 -C 6 )cycloalkyl group" refers to a cyclic alkyl group having 3 to 6 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
「(C1-C6)アルコキシ基」とは、例えば、メトキシ基、エトキシ基、ノルマルプロポキシ基、イソプロポキシ基、ノルマルブトキシ基、セカンダリーブトキシ基、ターシャリーブトキシ基、ノルマルペンチルオキシ基、イソペンチルオキシ基、ターシャリーペンチルオキシ基、ネオペンチルオキシ基、2,3‐ジメチルプロピルオキシ基、1‐エチルプロピルオキシ基、1‐メチルブチルオキシ基、ノルマルヘキシルオキシ基、イソヘキシルオキシ基、1,1,2‐トリメチルプロピルオキシ基等の直鎖又は分岐鎖状の炭素原子数1~6個のアルコキシ基を示す。
"(C 1 -C 6 )alkoxy group" means, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyl group. Oxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, 1,1 , 2-trimethylpropyloxy, and other linear or branched alkoxy groups having 1 to 6 carbon atoms.
「(C1-C6)アルキルスルファニル基」とは、例えば、メチルスルファニル基、エチルスルファニル基、ノルマルプロピルスルファニル基、イソプロピルスルファニル基、ノルマルブチルスルファニル基、セカンダリーブチルスルファニル基、ターシャリーブチルスルファニル基、ノルマルペンチルスルファニル基、イソペンチルスルファニル基、ターシャリーペンチルスルファニル基、ネオペンチルスルファニル基、2,3‐ジメチルプロピルスルファニル基、1‐エチルプロピルスルファニル基、1‐メチルブチルスルファニル基、ノルマルヘキシルスルファニル基、イソヘキシルスルファニル基、1,1,2‐トリメチルプロピルスルファニル基等の直鎖又は分岐鎖状の炭素原子数1~6個のアルキルスルファニル基を示す。
"(C 1 -C 6 )alkylsulfanyl group" means, for example, a methylsulfanyl group, an ethylsulfanyl group, a normal propylsulfanyl group, an isopropylsulfanyl group, a normal butylsulfanyl group, a secondary butylsulfanyl group, a tertiary butylsulfanyl group, Normal pentylsulfanyl group, isopentylsulfanyl group, tertiary pentylsulfanyl group, neopentylsulfanyl group, 2,3-dimethylpropylsulfanyl group, 1-ethylpropylsulfanyl group, 1-methylbutylsulfanyl group, normal hexylsulfanyl group, iso Indicates a linear or branched alkylsulfanyl group having 1 to 6 carbon atoms, such as a hexylsulfanyl group or a 1,1,2-trimethylpropylsulfanyl group.
「(C1-C6)アルキルスルフィニル基」とは、例えば、メチルスルフィニル基、エチルスルフィニル基、ノルマルプロピルスルフィニル基、イソプロピルスルフィニル基、ノルマルブチルスルフィニル基、セカンダリーブチルスルフィニル基、ターシャリーブチルスルフィニル基、ノルマルペンチルスルフィニル基、イソペンチルスルフィニル基、ターシャリーペンチルスルフィニル基、ネオペンチルスルフィニル基、2,3‐ジメチルプロピルスルフィニル基、1‐エチルプロピルスルフィニル基、1‐メチルブチルスルフィニル基、ノルマルヘキシルスルフィニル基、イソヘキシルスルフィニル基、1,1,2‐トリメチルプロピルスルフィニル基等の直鎖又は分岐鎖状の炭素原子数1~6個のアルキルスルフィニル基を示す。
"(C 1 -C 6 )alkylsulfinyl group" means, for example, a methylsulfinyl group, an ethylsulfinyl group, a normal propylsulfinyl group, an isopropylsulfinyl group, a normal butylsulfinyl group, a secondary butylsulfinyl group, a tertiary butylsulfinyl group, Normal pentylsulfinyl group, isopentylsulfinyl group, tertiary pentylsulfinyl group, neopentylsulfinyl group, 2,3-dimethylpropylsulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, iso It represents a linear or branched alkylsulfinyl group having 1 to 6 carbon atoms, such as a hexylsulfinyl group or a 1,1,2-trimethylpropylsulfinyl group.
「(C1-C6)アルキルスルホニル基」とは、例えば、メチルスルホニル基、エチルスルホニル基、ノルマルプロピルスルホニル基、イソプロピルスルホニル基、ノルマルブチルスルホニル基、セカンダリーブチルスルホニル基、ターシャリーブチルスルホニル基、ノルマルペンチルスルホニル基、イソペンチルスルホニル基、ターシャリーペンチルスルホニル基、ネオペンチルスルホニル基、2,3‐ジメチルプロピルスルホニル基、1‐エチルプロピルスルホニル基、1‐メチルブチルスルホニル基、ノルマルヘキシルスルホニル基、イソヘキシルスルホニル基、1,1,2‐トリメチルプロピルスルホニル基等の直鎖又は分岐鎖状の炭素原子数1~6個のアルキルスルホニル基を示す。
"(C 1 -C 6 )alkylsulfonyl group" means, for example, a methylsulfonyl group, an ethylsulfonyl group, a normal propylsulfonyl group, an isopropylsulfonyl group, a normal butylsulfonyl group, a secondary butylsulfonyl group, a tertiary butylsulfonyl group, Normal pentylsulfonyl group, isopentylsulfonyl group, tertiary pentylsulfonyl group, neopentylsulfonyl group, 2,3-dimethylpropylsulfonyl group, 1-ethylpropylsulfonyl group, 1-methylbutylsulfonyl group, normal hexylsulfonyl group, iso Indicates a linear or branched alkylsulfonyl group having 1 to 6 carbon atoms, such as a hexylsulfonyl group or a 1,1,2-trimethylpropylsulfonyl group.
「(C1-C6)アルキルカルボニル基」とは、例えば、アセチル基、プロパノイル基、ブタノイル基、2‐メチルプロパノイル基、ペンタノイル基、2‐メチルブタノイル基、3‐メチルブタノイル基、ピバロイル基、ヘキサノイル基等の前記(C1-C6)アルキル基を有するアルキルカルボニル基等の、炭素原子数2~7のアルキルカルボニル基を示す。
"(C 1 -C 6 )alkylcarbonyl group" includes, for example, acetyl group, propanoyl group, butanoyl group, 2-methylpropanoyl group, pentanoyl group, 2-methylbutanoyl group, 3-methylbutanoyl group, It refers to an alkylcarbonyl group having 2 to 7 carbon atoms, such as an alkylcarbonyl group having the above-mentioned (C 1 -C 6 ) alkyl group such as a pivaloyl group or a hexanoyl group.
「(C1-C6)アルキルカルボニルアミノ基」とは、例えば、アセチルアミノ基、プロパノイルアミノ基、ブタノイルアミノ基、2‐メチルプロパノイルアミノ基、ペンタノイルアミノ基、2‐メチルブタノイルアミノ基、3‐メチルブタノイルアミノ基、ピバロイルアミノ基、ヘキサノイルアミノ基等の前記(C1-C6)アルキル基を有するアルキルカルボニルアミノ基等の、炭素原子数2~7のアルキルカルボニルアミノ基を示す。
"(C 1 -C 6 )alkylcarbonylamino group" means, for example, acetylamino group, propanoylamino group, butanoylamino group, 2-methylpropanoylamino group, pentanoylamino group, 2-methylbutanoyl An alkylcarbonylamino group having 2 to 7 carbon atoms, such as an alkylcarbonylamino group having the above-mentioned (C 1 -C 6 ) alkyl group such as an amino group, 3-methylbutanoylamino group, pivaloylamino group, hexanoylamino group, etc. shows.
「(C1-C6)アルキルスルホニルアミノ基」とは、例えば、メチルスルホニルアミノ基、エチルスルホニルアミノ基、ノルマルプロピルスルホニルアミノ基、イソプロピルスルホニルアミノ基、ノルマルブチルスルホニルアミノ基、セカンダリーブチルスルホニルアミノ基、ターシャリーブチルスルホニルアミノ基、ノルマルペンチルスルホニルアミノ基、イソペンチルスルホニルアミノ基、ターシャリーペンチルスルホニルアミノ基、ネオペンチルスルホニルアミノ基、2,3‐ジメチルプロピルスルホニルアミノ基、1‐エチルプロピルスルホニルアミノ基、1‐メチルブチルスルホニルアミノ基、ノルマルヘキシルスルホニルアミノ基、イソヘキシルスルホニルアミノ基、1,1,2‐トリメチルプロピルスルホニルアミノ基等の直鎖又は分岐鎖状の炭素原子数1~6個のアルキルスルホニルアミノ基を示す。
"(C 1 -C 6 )alkylsulfonylamino group" means, for example, methylsulfonylamino group, ethylsulfonylamino group, normal propylsulfonylamino group, isopropylsulfonylamino group, normal butylsulfonylamino group, secondary butylsulfonylamino group , tertiary butylsulfonylamino group, normal pentylsulfonylamino group, isopentylsulfonylamino group, tertiary pentylsulfonylamino group, neopentylsulfonylamino group, 2,3-dimethylpropylsulfonylamino group, 1-ethylpropylsulfonylamino group , 1-methylbutylsulfonylamino group, n-hexylsulfonylamino group, isohexylsulfonylamino group, 1,1,2-trimethylpropylsulfonylamino group, etc. Straight chain or branched alkyl having 1 to 6 carbon atoms Indicates a sulfonylamino group.
「N‐(C1-C6)アルキルアミノカルボニル基」とは、例えばN‐メチル‐アミノカルボニル基、N‐エチルアミノカルボニル基、N‐ノルマルプロピルアミノカルボニル基、N‐イソプロピルアミノカルボニル基、N‐ノルマルブチルアミノカルボニル基、N‐イソブチルアミノカルボニル基、N‐セカンダリーブチルアミノカルボニル基、N‐ターシャリーブチルアミノカルボニル基、N‐ノルマルペンチルアミノカルボニル基、N‐イソペンチルアミノカルボニル基、N‐ターシャリーペンチルアミノカルボニル基、N‐ネオペンチアミノカルボニル基、N‐ノルマルヘキシルアミノカルボニル基、N‐イソヘキシルアミノカルボニル基等の直鎖又は分岐鎖状の炭素原子数1~6個のアルキル基を有する炭素原子数2~7個のアルキルアミノカルボニル基を示す。
"N-(C 1 -C 6 )alkylaminocarbonyl group" means, for example, N-methyl-aminocarbonyl group, N-ethylaminocarbonyl group, N-normalpropylaminocarbonyl group, N-isopropylaminocarbonyl group, -Normal butylaminocarbonyl group, N-isobutylaminocarbonyl group, N-secondary butylaminocarbonyl group, N-tertiary butylaminocarbonyl group, N-normalpentylaminocarbonyl group, N-isopentylaminocarbonyl group, N-tertiary Contains a linear or branched alkyl group having 1 to 6 carbon atoms, such as a liepentylaminocarbonyl group, N-neopentylaminocarbonyl group, N-normalhexylaminocarbonyl group, and N-isohexylaminocarbonyl group. It represents an alkylaminocarbonyl group having 2 to 7 carbon atoms.
「N,N‐ジ(C1-C6)アルキルアミノカルボニル基」とは、例えば、N,N‐ジメチル‐アミノカルボニル基、N,N‐ジエチルアミノカルボニル基、N,N‐ジノルマルプロピルアミノカルボニル基、N,N‐ジイソプロピルアミノカルボニル基、N,N‐ジノルマルブチルアミノカルボニル基、N,N‐ジセカンダリーブチルアミノカルボニル基、N,N‐ジターシャリーブチルアミノカルボニル基、N‐メチル‐N‐エチルアミノカルボニル基、N‐メチル‐N‐ノルマルプロピルアミノカルボニル基、N‐メチル‐N‐イソプロピルアミノカルボニル基、N‐メチル‐N‐ノルマルブチルアミノカルボニル基、N‐メチル‐N‐セカンダリーブチルアミノカルボニル基、N‐メチル‐N‐ターシャリーブチルアミノカルボニル基、N‐メチル‐N‐ノルマルペンチルアミノカルボニル基、N‐メチル‐N‐イソペンチルアミノカルボニル基、N‐メチル‐N‐ターシャリーペンチルアミノカルボニル基、N‐メチル‐N‐ネオペンチルアミノカルボニル基、N‐メチル‐N‐(2,3‐ジメチル‐プロピル)アミノカルボニル基、N‐メチル‐N‐(1‐エチルプロピル)アミノカルボニル基、N‐メチル‐N‐(1‐メチル‐ブチル)アミノカルボニル基、N‐メチル‐N‐ノルマルヘキシルアミノカルボニル基、N‐メチル‐N‐イソヘキシルアミノカルボニル基、N‐メチル‐N‐(1,1,2‐トリメチル‐プロピル)アミノカルボニル基等の直鎖又は分岐鎖状の炭素原子数1~6個のアルキル基を有する炭素原子数3~13個のジアルキルアミノカルボニル基を示す。
"N,N-di(C 1 -C 6 )alkylaminocarbonyl group" means, for example, N,N-dimethyl-aminocarbonyl group, N,N-diethylaminocarbonyl group, N,N-dinormalpropylaminocarbonyl group. group, N,N-diisopropylaminocarbonyl group, N,N-dinormalbutylaminocarbonyl group, N,N-dise-butylaminocarbonyl group, N,N-ditertiarybutylaminocarbonyl group, N-methyl-N- Ethylaminocarbonyl group, N-methyl-N-normalpropylaminocarbonyl group, N-methyl-N-isopropylaminocarbonyl group, N-methyl-N-normalbutylaminocarbonyl group, N-methyl-N-secondary butylaminocarbonyl group group, N-methyl-N-tert-butylaminocarbonyl group, N-methyl-N-normalpentylaminocarbonyl group, N-methyl-N-isopentylaminocarbonyl group, N-methyl-N-tert-pentylaminocarbonyl group group, N-methyl-N-neopentylaminocarbonyl group, N-methyl-N-(2,3-dimethyl-propyl)aminocarbonyl group, N-methyl-N-(1-ethylpropyl)aminocarbonyl group, N -Methyl-N-(1-methyl-butyl)aminocarbonyl group, N-methyl-N-normalhexylaminocarbonyl group, N-methyl-N-isohexylaminocarbonyl group, N-methyl-N-(1,1 , 2-trimethyl-propyl) aminocarbonyl group having a linear or branched alkyl group having 1 to 6 carbon atoms.
「(C1-C6)アルコキシカルボニル基」とは、例えば、メトキシカルボニル基、エトキシカルボニル基、ノルマルプロポキシカルボニル基、イソプロポキシカルボニル基、ノルマルブトキシカルボニル基、イソブトキシカルボニル基、セカンダリーブトキシカルボニル基、ターシャリーブトキシカルボニル基、ペンチルオキシカルボニル基等の前記(C1-C6)アルコキシ基を有するアルコキシカルボニル基等の、炭素原子数2~7のアルコキシカルボニル基を示す。
"(C 1 -C 6 )alkoxycarbonyl group" means, for example, methoxycarbonyl group, ethoxycarbonyl group, normal propoxycarbonyl group, isopropoxycarbonyl group, normal butoxycarbonyl group, isobutoxycarbonyl group, secondary butoxycarbonyl group, It refers to an alkoxycarbonyl group having 2 to 7 carbon atoms, such as an alkoxycarbonyl group having the above-mentioned (C 1 -C 6 ) alkoxy group, such as a tert-butoxycarbonyl group or a pentyloxycarbonyl group.
「N‐(C1-C6)アルキルアミノスルホニル基」とは、例えば、N‐メチルアミノスルホニル基、N‐エチルアミノスルホニル基、N‐ノルマルプロピルアミノスルホニル基、N‐イソプロピルアミノスルホニル基、N‐ノルマルブチルアミノスルホニル基、N‐セカンダリーブチルアミノスルホニル基、N‐ターシャリーブチルアミノスルホニル基、N‐ノルマルペンチルアミノスルホニル基、N‐イソペンチルアミノスルホニル基、N‐ターシャリーペンチルアミノスルホニル基、N‐ネオペンチルアミノスルホニル基、N‐(2,3‐ジメチルプロピル)アミノスルホニル基、N‐(1‐エチルプロピル)アミノスルホニル基、N‐(1‐メチルブチル)アミノスルホニル基、N‐ノルマルヘキシルアミノスルホニル基、N‐イソヘキシルアミノスルホニル基、N‐(1,1,2‐トリメチルプロピル)アミノスルホニル基等の直鎖又は分岐鎖状の炭素原子数1~6個のアルキルアミノスルホニル基を示す。
"N-(C 1 -C 6 )alkylaminosulfonyl group" means, for example, N-methylaminosulfonyl group, N-ethylaminosulfonyl group, N-normalpropylaminosulfonyl group, N-isopropylaminosulfonyl group, N-isopropylaminosulfonyl group, -Normal butylaminosulfonyl group, N-Secondary butylaminosulfonyl group, N-Tertiary butylaminosulfonyl group, N-Normalpentylaminosulfonyl group, N-Isopentylaminosulfonyl group, N-Tertiary pentylaminosulfonyl group, N -Neopentylaminosulfonyl group, N-(2,3-dimethylpropyl)aminosulfonyl group, N-(1-ethylpropyl)aminosulfonyl group, N-(1-methylbutyl)aminosulfonyl group, N-normalhexylaminosulfonyl group represents a linear or branched alkylaminosulfonyl group having 1 to 6 carbon atoms, such as N-isohexylaminosulfonyl group, N-(1,1,2-trimethylpropyl)aminosulfonyl group, etc.
「N,N‐ジ(C1-C6)アルキルアミノスルホニル基」とは、例えば、N,N‐ジメチルアミノスルホニル基、N,N‐ジエチルアミノスルホニル基、N,N‐ジノルマルプロピルアミノスルホニル基、N,N‐ジイソプロピルアミノスルホニル基、N,N‐ジノルマルブチルアミノスルホニル基、N,N‐ジセカンダリーブチルアミノスルホニル基、N,N‐ジターシャリーブチルアミノスルホニル基、N‐メチル-N‐エチルアミノスルホニル基、N‐メチル-N‐ノルマルプロピルアミノスルホニル基、N‐メチル-N‐イソプロピルアミノスルホニル基、N‐メチル-N‐ノルマルブチルアミノスルホニル基、N‐メチル-N‐セカンダリーブチルアミノスルホニル基、N‐メチル-N‐ターシャリーブチルアミノスルホニル基、N‐メチル-N‐ノルマルペンチルアミノスルホニル基、N‐メチル-N‐イソペンチルアミノスルホニル基、N‐メチル-N‐ターシャリーペンチルアミノスルホニル基、N‐メチル-N‐ネオペンチルアミノスルホニル基、N‐メチル-N‐(2,3‐ジメチルプロピル)アミノスルホニル基、N‐メチル-N‐(1‐エチルプロピル)アミノスルホニル基、N‐メチル-N‐(1‐メチルブチル)アミノスルホニル基、N‐メチル-N‐ノルマルヘキシルアミノスルホニル基、N‐メチル-N‐イソヘキシルアミノスルホニル基、N‐メチル-N‐(1,1,2‐トリメチルプロピル)アミノスルホニル基等の直鎖又は分岐鎖状の炭素原子数2~12個のジアルキルアミノスルホニル基を示す。
"N,N-di(C 1 -C 6 )alkylaminosulfonyl group" means, for example, N,N-dimethylaminosulfonyl group, N,N-diethylaminosulfonyl group, N,N-dinormalpropylaminosulfonyl group. , N,N-diisopropylaminosulfonyl group, N,N-di-n-butylaminosulfonyl group, N,N-dise-butylaminosulfonyl group, N,N-ditertiarybutylaminosulfonyl group, N-methyl-N-ethyl Aminosulfonyl group, N-methyl-N-normalpropylaminosulfonyl group, N-methyl-N-isopropylaminosulfonyl group, N-methyl-N-normalbutylaminosulfonyl group, N-methyl-N-secondary butylaminosulfonyl group , N-methyl-N-tert-butylaminosulfonyl group, N-methyl-N-normalpentylaminosulfonyl group, N-methyl-N-isopentylaminosulfonyl group, N-methyl-N-tert-pentylaminosulfonyl group , N-methyl-N-neopentylaminosulfonyl group, N-methyl-N-(2,3-dimethylpropyl)aminosulfonyl group, N-methyl-N-(1-ethylpropyl)aminosulfonyl group, N-methyl -N-(1-methylbutyl)aminosulfonyl group, N-methyl-N-normalhexylaminosulfonyl group, N-methyl-N-isohexylaminosulfonyl group, N-methyl-N-(1,1,2-trimethyl This refers to a straight-chain or branched dialkylaminosulfonyl group having 2 to 12 carbon atoms, such as a propyl)aminosulfonyl group.
上記「(C1-C6)アルキル基」、「(C2-C6)アルケニル基」、「(C2-C6)アルキニル基」、「(C1-C6)アルコキシ基」、「(C1-C6)アルキルスルファニル基」、「(C1-C6)アルキルスルフィニル基」、「(C1-C6)アルキルスルホニル基」、「(C3-C6)シクロアルキル基」、「(C1-C6)アルキルカルボニルアミノ基」、「(C1-C6)アルキルスルホニルアミノ基」、「N‐(C1-C6)アルキルアミノカルボニル基」、「(C1-C6)アルコキシカルボニル基」等の置換し得る位置に1又は2以上のハロゲン原子が置換されていても良く、置換されるハロゲン原子が2以上の場合は、ハロゲン原子は同一又は異なっても良い。
The above-mentioned "(C 1 -C 6 )alkyl group", "(C 2 -C 6 )alkenyl group", "(C 2 -C 6 )alkynyl group", "(C 1 -C 6 )alkoxy group", " (C 1 -C 6 )alkylsulfanyl group", "(C 1 -C 6 )alkylsulfinyl group", "(C 1 -C 6 )alkylsulfonyl group", "(C 3 -C 6 )cycloalkyl group" , "(C 1 -C 6 )alkylcarbonylamino group", "(C 1 -C 6 )alkylsulfonylamino group", "N-(C 1 -C 6 )alkylaminocarbonyl group", "(C 1 - One or more halogen atoms may be substituted at substitutable positions such as "C 6 ) alkoxycarbonyl group", and when there are two or more halogen atoms to be substituted, the halogen atoms may be the same or different. .
それぞれ、「ハロ(C1-C6)アルキル基」、「ハロ(C2-C6)アルケニル基」、「ハロ(C2-C6)アルキニル基」、「ハロ(C1-C6)アルコキシ基」、「ハロ(C1-C6)アルキルスルファニル基」、「ハロ(C1-C6)アルキルスルフィニル基」、「ハロ(C1-C6)アルキルスルホニル基」、「ハロ(C3-C6)シクロアルキル基」、「ハロ(C1-C6)アルキルカルボニルアミノ基」、「ハロ(C1-C6)アルキルスルホニルアミノ基」、「N‐ハロ(C1-C6)アルキルアミノカルボニル基」、「ハロ(C1-C6)アルコキシカルボニル基」等と示す。
"Halo(C 1 -C 6 )alkyl group", "Halo(C 2 -C 6 )alkenyl group", "Halo(C 2 -C 6 )alkynyl group", "Halo(C 1 -C 6 ) alkyl group", respectively. "alkoxy group", "halo(C 1 -C 6 )alkylsulfanyl group", "halo(C 1 -C 6 )alkylsulfinyl group", "halo(C 1 -C 6 )alkylsulfonyl group", "halo(C 6 )alkylsulfonyl group" 3 -C 6 )cycloalkyl group", "Halo(C 1 -C 6 )alkylcarbonylamino group", "Halo(C 1 -C 6 )alkylsulfonylamino group", "N-halo(C 1 -C 6 ) )alkylaminocarbonyl group", "halo(C 1 -C 6 )alkoxycarbonyl group", etc.
「(C1-C6)」、「(C2-C6)」、「(C3-C6)」等の表現は各種置換基の炭素原子数の範囲を示す。更に、上記置換基が連結した基についても上記定義を示すことができ、例えば、「(C1-C6)アルコキシ(C1-C6)アルキル基」の場合は直鎖又は分岐鎖状の炭素数1~6個のアルコキシ基が直鎖又は分岐鎖状の炭素数1~6個のアルキル基に結合していることを示す。
Expressions such as "(C 1 -C 6 )", "(C 2 -C 6 )", "(C 3 -C 6 )", etc. indicate the range of the number of carbon atoms of various substituents. Furthermore, the above definition can also be given to the group to which the above substituents are connected; for example, in the case of "(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group", a straight chain or branched chain Indicates that an alkoxy group having 1 to 6 carbon atoms is bonded to a linear or branched alkyl group having 1 to 6 carbon atoms.
本発明の一般式(1)で表される化合物の塩類としては、例えば塩酸塩、硫酸塩、硝酸塩、燐酸塩等の無機酸塩類、酢酸塩、フマル酸塩、マレイン酸塩、シュウ酸塩、メタンスルホン酸塩、ベンゼンスルホン酸塩、パラトルエンスルホン酸塩等の有機酸塩類、ナトリウムイオン、カリウムイオン、カルシウムイオン、トリメチルアンモニウム等の無機又は有機の塩基との塩類を例示することができる。
Examples of the salts of the compound represented by the general formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate, phosphate, acetate, fumarate, maleate, oxalate, Examples include organic acid salts such as methanesulfonate, benzenesulfonate, and paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium.
本発明の一般式(1)で表される化合物及びその塩類は、その構造式中に1つ又は複数個の不斉中心を有する場合があり、2種以上の光学異性体及びジアステレオマーが存在する場合もあり、本発明は各々の光学異性体及びそれらが任意の割合で含まれる混合物をも全て包含するものである。又、本発明の一般式(1)で表される化合物及びその塩類は、その構造式中に炭素‐炭素二重結合に由来する2種の幾何異性体が存在する場合もあるが、本発明は各々の幾何異性体及びそれらが任意の割合で含まれる混合物をも全て包含するものである。さらに、本発明の一般式(1)で表される化合物及びその塩類には、複数の互変異性体が存在する場合もあるが、本発明は各々の互変異性体及びそれらが任意の割合で含まれる混合物をも全て包含するものである。
The compound represented by the general formula (1) of the present invention and its salts may have one or more asymmetric centers in its structural formula, and may have two or more optical isomers and diastereomers. In some cases, optical isomers exist, and the present invention includes all optical isomers and mixtures containing them in arbitrary proportions. In addition, the compound represented by the general formula (1) of the present invention and its salts may have two types of geometric isomers derived from a carbon-carbon double bond in the structural formula, but the present invention It also includes all geometric isomers and mixtures containing them in arbitrary proportions. Further, the compound represented by the general formula (1) of the present invention and its salts may have a plurality of tautomers, but the present invention covers each tautomer and their arbitrary proportions. It also includes all mixtures contained in the above.
本発明の一般式(1)で表される化合物において、以下に好ましい態様を示す。
一般式(1)において、R1としては、上記の(a1)、(a2)、(a3)、(a4)、(a5)、(a6)、(a10)、(a12)、(a14)、(a15)、(a16)、(a17)、(a18)、(a19)、(a24)、(a25)、(a26)、(a27)、(a36)、(a37)、(a40)、(a41)、(a44)、(a45)、(a46)、(a47)、(a50)、(a51)、(a52)、(a53)、(a54)、(a55)、(a60)、(a61)、(a64)、(a65)、(a66)、(a67)、(a68)、(a69)、(a72)、又は(a73)の基が好ましく、上記の(a1)、(a3)、(a6)、(a10)、(a16)、(a17)、(a18)、(a44)、(a45)、(a46)、(a47)、(a50)、(a61)、(a64)、(a67)、(a69)、又は(a72)の基がより好ましい。 Preferred embodiments of the compound represented by general formula (1) of the present invention are shown below.
In general formula (1), R 1 is the above (a1), (a2), (a3), (a4), (a5), (a6), (a10), (a12), (a14), (a15), (a16), (a17), (a18), (a19), (a24), (a25), (a26), (a27), (a36), (a37), (a40), (a41 ), (a44), (a45), (a46), (a47), (a50), (a51), (a52), (a53), (a54), (a55), (a60), (a61), The groups (a64), (a65), (a66), (a67), (a68), (a69), (a72), or (a73) are preferred, and the above (a1), (a3), (a6) , (a10), (a16), (a17), (a18), (a44), (a45), (a46), (a47), (a50), (a61), (a64), (a67), ( a69) or (a72) is more preferred.
一般式(1)において、R1としては、上記の(a1)、(a2)、(a3)、(a4)、(a5)、(a6)、(a10)、(a12)、(a14)、(a15)、(a16)、(a17)、(a18)、(a19)、(a24)、(a25)、(a26)、(a27)、(a36)、(a37)、(a40)、(a41)、(a44)、(a45)、(a46)、(a47)、(a50)、(a51)、(a52)、(a53)、(a54)、(a55)、(a60)、(a61)、(a64)、(a65)、(a66)、(a67)、(a68)、(a69)、(a72)、又は(a73)の基が好ましく、上記の(a1)、(a3)、(a6)、(a10)、(a16)、(a17)、(a18)、(a44)、(a45)、(a46)、(a47)、(a50)、(a61)、(a64)、(a67)、(a69)、又は(a72)の基がより好ましい。 Preferred embodiments of the compound represented by general formula (1) of the present invention are shown below.
In general formula (1), R 1 is the above (a1), (a2), (a3), (a4), (a5), (a6), (a10), (a12), (a14), (a15), (a16), (a17), (a18), (a19), (a24), (a25), (a26), (a27), (a36), (a37), (a40), (a41 ), (a44), (a45), (a46), (a47), (a50), (a51), (a52), (a53), (a54), (a55), (a60), (a61), The groups (a64), (a65), (a66), (a67), (a68), (a69), (a72), or (a73) are preferred, and the above (a1), (a3), (a6) , (a10), (a16), (a17), (a18), (a44), (a45), (a46), (a47), (a50), (a61), (a64), (a67), ( a69) or (a72) is more preferred.
一般式(1)において、R2aとしては、上記の(b1) 水素原子が好ましい。
In general formula (1), R 2a is preferably the above-mentioned (b1) hydrogen atom.
一般式(1)において、R2bとしては、上記の(c1) 水素原子が好ましい。
In general formula (1), R 2b is preferably the above-mentioned (c1) hydrogen atom.
一般式(1)において、R3aとしては、上記の(d1)、(d2)、(d3)、又は(d4)の基が好ましく、上記の(d1)又は(d2)の基がより好ましい。
In general formula (1), R 3a is preferably the group (d1), (d2), (d3), or (d4) above, and more preferably the group (d1) or (d2) above.
一般式(1)において、R3bとしては、上記の(e1)又は(e2)の基が好ましい。
In general formula (1), R 3b is preferably the group (e1) or (e2) above.
一般式(1)において、R4aとしては、上記の(f1)又は(f2)の基が好ましく、上記の(f1)の基がより好ましい。
In general formula (1), R 4a is preferably the above group (f1) or (f2), and more preferably the above group (f1).
一般式(1)において、R4bとしては、上記の(g1)又は(g2)の基が好ましく、上記の(g1)の基がより好ましい。
In general formula (1), R 4b is preferably the group (g1) or (g2) above, and more preferably the group (g1) above.
一般式(1)において、R5としては、上記の(h1)、(h3)、(h4)、(h5)、(h11)、(h12)、(h13)、(h14)、(h15)、(h16)、(h17)、(h18)、(h19)、(h20)、(h25)、(h26)、(h27)、(h28)、(h31)、(h32)、(h41)、(h42)、(h53)、又は(h54)の基が好ましく、上記の(h1)、(h11)、(h12)、(h13)、(h14)、(h15)、(h16)、(h18)、(h19)、(h25)、(h28)、(h31)、(h42)、又は(h53)がより好ましい。
In general formula (1), R 5 includes the above (h1), (h3), (h4), (h5), (h11), (h12), (h13), (h14), (h15), (h16), (h17), (h18), (h19), (h20), (h25), (h26), (h27), (h28), (h31), (h32), (h41), (h42 ), (h53), or (h54) groups are preferred, and the above groups (h1), (h11), (h12), (h13), (h14), (h15), (h16), (h18), ( h19), (h25), (h28), (h31), (h42), or (h53) are more preferred.
一般式(1)において、R6としては、上記の(i1)又は(i2)の基が好ましく、上記の(i1)の基がより好ましい。
In general formula (1), R 6 is preferably the group (i1) or (i2) above, and more preferably the group (i1) above.
一般式(1)において、Xとしては、ヒドロキシル基、(C1-C6)アルコキシ基、(C1-C6)アルキルスルファニル基、(C1-C6)アルキルスルフィニル基、又は(C1-C6)アルキルスルホニル基が好ましく、ヒドロキシル基がより好ましい。
In general formula (1), X is a hydroxyl group, a (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 ) alkylsulfanyl group, a (C 1 -C 6 )alkylsulfinyl group, or a (C 1 -C 6 )alkylsulfinyl group. -C 6 )Alkylsulfonyl group is preferred, and hydroxyl group is more preferred.
一般式(1)において、Yとしては、酸素原子、硫黄原子、又はNR7基(式中、R7は、ハロゲン原子、シアノ基、(C1-C6)アルキル基、及びハロ(C1-C6)アルキル基からなる群からそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基を示す。)が好ましく、酸素原子又は硫黄原子がより好ましい。
In the general formula (1), Y is an oxygen atom, a sulfur atom, or an NR 7 group (wherein R 7 is a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, or a halo (C 1 -C 6 ) represents a substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from the group consisting of alkyl groups), and an oxygen atom or a sulfur atom is more preferable.
一般式(1)において、置換基群Aとしては、上記の(j1)、(j5)、(j6)、(j7)、(j8)、(j9)、及び(j18)の基からなることが好ましく、上記の(j5)であることがより好ましい。
In general formula (1), substituent group A may consist of the above groups (j1), (j5), (j6), (j7), (j8), (j9), and (j18). Preferably, the above (j5) is more preferable.
一般式(1)において、置換基群Bとしては、上記の(k1)、(k2)、(k3)、(k4)、(k5)、(k6)、(k7)、(k8)、(k9)、(k10)、(k11)、(k12)、(k13)、(k14)、(k15)、及び(k16)の基からなることが好ましい。
In general formula (1), substituent group B includes the above (k1), (k2), (k3), (k4), (k5), (k6), (k7), (k8), (k9). ), (k10), (k11), (k12), (k13), (k14), (k15), and (k16).
一般式(1)において、置換基群Cとしては、上記の(l1)、(l2)、(l3)、(l6)、(l9)、(l11)、(l12)、(l13)、(l14)、(l17)、(l19)、(l20)、(l21)、(l23)、(l24)、(l25)、(l26)、(l27)、(l28)、(l29)、及び(l30)の基からなることが好ましく、上記の(l1)、(l2)、(l9)、(l11)、(l14)、(l17)、(l19)、及び(l20)の基からなることがより好ましい。
In general formula (1), the substituent group C includes the above (l1), (l2), (l3), (l6), (l9), (l11), (l12), (l13), (l14 ), (l17), (l19), (l20), (l21), (l23), (l24), (l25), (l26), (l27), (l28), (l29), and (l30) It is preferably composed of the groups (l1), (l2), (l9), (l11), (l14), (l17), (l19), and (l20) described above. .
一般式(1)において、置換基群Dとしては、上記の(m1)、(m2)、(m3)、(m7)、(m10)、(m12)、(m13)、(m14)、(m15)、(m18)、(m20)、(m21)、(m22)、(m26)、(m27)、(m28)、(m29)、(m30)、(m31)、(m32)、(m33)、及び(m36)の基からなることが好ましく、上記の(m7)、(m15)、(m18)、(m20)、及び(m36)の基であることがより好ましい。
In general formula (1), the substituent group D includes the above (m1), (m2), (m3), (m7), (m10), (m12), (m13), (m14), (m15 ), (m18), (m20), (m21), (m22), (m26), (m27), (m28), (m29), (m30), (m31), (m32), (m33), and (m36), and more preferably the above-mentioned groups (m7), (m15), (m18), (m20), and (m36).
一般式(1)において、置換基群Eとしては、上記の(n1)、(n2)、(n3)、(n7)、(n8)、(n9)、(n10)、(n11)、(n12)、(n13)、(n14)、(n16)、(n17)、(n18)、(n19)、(n20)、(n21)、(n22)、(n23)、(n24)、(n25)、(n26)、(n27)、(n28)、(n29)、(n30)、(n31)、(n32)、(n33)、(n34)、及び(n35)の基からなることが好ましく、上記の(n1)、(n2)、(n3)、(n7)、(n8)、(n9)、(n10)、(n12)、(n13)、(n14)、(n19)、(n21)、(n33)、及び(n34)の基からなることがより好ましい。
In general formula (1), the substituent group E includes the above (n1), (n2), (n3), (n7), (n8), (n9), (n10), (n11), (n12 ), (n13), (n14), (n16), (n17), (n18), (n19), (n20), (n21), (n22), (n23), (n24), (n25), It preferably consists of the groups (n26), (n27), (n28), (n29), (n30), (n31), (n32), (n33), (n34), and (n35), and (n1), (n2), (n3), (n7), (n8), (n9), (n10), (n12), (n13), (n14), (n19), (n21), (n33 ), and (n34) are more preferable.
本発明の各種化合物は、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。
Various compounds of the present invention can be produced, for example, by the following production methods, but the present invention is not limited thereto.
製造方法1
本発明の一般式(1‐1)で表される化合物は、一般式(2)で表される化合物から、下記工程[a]により製造することができる。
Manufacturing method 1
The compound represented by the general formula (1-1) of the present invention can be produced from the compound represented by the general formula (2) by the following step [a].
本発明の一般式(1‐1)で表される化合物は、一般式(2)で表される化合物から、下記工程[a]により製造することができる。
The compound represented by the general formula (1-1) of the present invention can be produced from the compound represented by the general formula (2) by the following step [a].
{式中、R1、R2a、R2b、R3a、R3b、R4a、R4b、R5、及びYは前記に同じ。}
{In the formula, R 1 , R 2a , R 2b , R 3a , R 3b , R 4a , R 4b , R 5 and Y are the same as above. }
工程[a]の製造方法
一般式(2)で表される化合物を、塩基及び不活性溶媒存在下、一般式(3)で表される化合物と反応させることにより、本発明の一般式(1‐1)で表される化合物を製造することができる。 Manufacturing method of step [a] By reacting the compound represented by general formula (2) with the compound represented by general formula (3) in the presence of a base and an inert solvent, the general formula (1 A compound represented by -1) can be produced.
一般式(2)で表される化合物を、塩基及び不活性溶媒存在下、一般式(3)で表される化合物と反応させることにより、本発明の一般式(1‐1)で表される化合物を製造することができる。 Manufacturing method of step [a] By reacting the compound represented by general formula (2) with the compound represented by general formula (3) in the presence of a base and an inert solvent, the general formula (1 A compound represented by -1) can be produced.
本反応で使用できる塩基としては、例えば、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム等の水酸化物、ナトリウムメトキサイド、ナトリウムエトキサイド、ナトリウムターシャリーブトキサイド、カリウムターシャリーブトキサイド等のアルコキサイド、水素化ナトリウム、水素化カリウム等のアルカリ金属ヒドリド類、炭酸リチウム、炭酸水素リチウム、炭酸ナトリウム、炭酸水素ナトリウム、炭酸カリウム、炭酸水素カリウム、炭酸カルシウム、炭酸マグネシウム、炭酸セシウム等の炭酸塩、酢酸リチウム、酢酸ナトリウム、酢酸カリウム等の酢酸塩、ピリジン、ピコリン、ルチジン、トリエチルアミン、トリブチルアミン、N,N‐ジイソプロピルエチルアミン、1,8‐ジアザビシクロ[5.4.0]‐7‐ウンデセン(DBU)等の有機塩基等を挙げることができ、その使用量は一般式(2)で表される化合物に対して通常1倍モル~10倍モルの範囲で使用される。
Examples of bases that can be used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide. alkoxides such as side, alkali metal hydrides such as sodium hydride, potassium hydride, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate, cesium carbonate, etc. Carbonates, acetates such as lithium acetate, sodium acetate, potassium acetate, pyridine, picoline, lutidine, triethylamine, tributylamine, N,N-diisopropylethylamine, 1,8-diazabicyclo[5.4.0]-7-undecene Examples include organic bases such as (DBU), and the amount used is usually in the range of 1 to 10 times the mole of the compound represented by the general formula (2).
本反応で使用できる不活性溶媒としては、本反応の進行を著しく阻害しないものであればよく、例えば、ペンタン、ヘキサン、シクロヘキサン等の鎖状又は環状飽和炭化水素類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン、ジクロロベンゼン等のハロゲン化芳香族炭化水素類、ジエチルエーテル、メチルターシャリーブチルエーテル、ジオキサン、テトラヒドロフラン等の鎖状又は環状エーテル類等の不活性溶媒、アセトニトリル、プロピオニトリル等のニトリル類、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‐イミダゾリジノン等の非プロトン性極性溶媒、メタノール、エタノール、プロパノール、ブタノール、2‐プロパノール等のアルコール類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。その使用量は、一般式(2)で表される化合物1モルに対して通常0.1~100Lの範囲から適宜選択すればよい。
Inert solvents that can be used in this reaction may be those that do not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc. Aromatic hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, acetonitrile, propionitrile Nitriles such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone, methanol, ethanol, propanol, butanol, 2 Examples include alcohols such as -propanol, and these inert solvents can be used alone or in combination of two or more. The amount used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (2).
本反応は等モル反応であるので、各化合物を等モル使用すればよいが、いずれかの化合物を過剰に用いることもできる。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良く、反応時間は反応規模、反応温度等により変化し、一定ではないが、通常数分~48時間の範囲で適宜選択すれば良い。反応終了後、目的物を含む反応系から目的物を常法により単離すれば良く、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。
Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of each compound, but it is also possible to use an excess of either compound. 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., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate. 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
本発明の一般式(1‐2)で表される化合物は、一般式(2)で表される化合物から、下記工程[b]により製造することができる。
Manufacturing method 2
The compound represented by general formula (1-2) of the present invention can be produced from the compound represented by general formula (2) by the following step [b].
本発明の一般式(1‐2)で表される化合物は、一般式(2)で表される化合物から、下記工程[b]により製造することができる。
The compound represented by general formula (1-2) of the present invention can be produced from the compound represented by general formula (2) by the following step [b].
{式中、R1、R2a、R2b、R3a、R3b、R4a、R4b、R5、R6、及びYは前記に同じ。Lは例えば、塩素、臭素などハロゲン原子、イミダゾリル基、トリクロロメトキシ基等の脱離基を示す。}
{In the formula, R 1 , R 2a , R 2b , R 3a , R 3b , R 4a , R 4b , R 5 , R 6 and Y are the same as above. L represents, for example, a halogen atom such as chlorine or bromine, or a leaving group such as an imidazolyl group or a trichloromethoxy group. }
工程[b]の製造方法
一般式(2)で表される化合物を、不活性溶媒の存在下、塩基の存在又は非存在下、一般式(4)で表される化合物と一般式(5)で表される化合物との反応物と反応させることにより、一般式(1-2)で表される化合物を製造することができる。 Manufacturing method of step [b] A compound represented by general formula (2) is mixed with a compound represented by general formula (4) in the presence or absence of a base in the presence of an inert solvent and general formula (5). A compound represented by the general formula (1-2) can be produced by reacting with a reaction product of the compound represented by the formula (1-2).
一般式(2)で表される化合物を、不活性溶媒の存在下、塩基の存在又は非存在下、一般式(4)で表される化合物と一般式(5)で表される化合物との反応物と反応させることにより、一般式(1-2)で表される化合物を製造することができる。 Manufacturing method of step [b] A compound represented by general formula (2) is mixed with a compound represented by general formula (4) in the presence or absence of a base in the presence of an inert solvent and general formula (5). A compound represented by the general formula (1-2) can be produced by reacting with a reaction product of the compound represented by the formula (1-2).
本反応で使用できる塩基としては、例えば、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化カルシウム等の水酸化物、ナトリウムメトキサイド、ナトリウムエトキサイド、ナトリウムターシャリーブトキサイド、カリウムターシャリーブトキサイド等のアルコキサイド、水素化ナトリウム、水素化カリウム等のアルカリ金属ヒドリド類、炭酸リチウム、炭酸水素リチウム、炭酸ナトリウム、炭酸水素ナトリウム、炭酸カリウム、炭酸水素カリウム、炭酸カルシウム、炭酸マグネシウム、炭酸セシウム等の炭酸塩、酢酸リチウム、酢酸ナトリウム、酢酸カリウム等の酢酸塩、ピリジン、ピコリン、ルチジン、トリエチルアミン、トリブチルアミン、N,N‐ジイソプロピルエチルアミン、DBU等の有機塩基等を挙げることができ、その使用量は一般式(2)で表される化合物に対して通常1倍モル~10倍モルの範囲で使用される。
Examples of bases that can be used in this reaction include hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, and calcium hydroxide, sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide. alkoxides such as side, alkali metal hydrides such as sodium hydride, potassium hydride, lithium carbonate, lithium hydrogen carbonate, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, potassium hydrogen carbonate, calcium carbonate, magnesium carbonate, cesium carbonate, etc. Examples include carbonates, acetates such as lithium acetate, sodium acetate, and potassium acetate, and organic bases such as pyridine, picoline, lutidine, triethylamine, tributylamine, N,N-diisopropylethylamine, and DBU. It is usually used in an amount of 1 to 10 times the mole of the compound represented by general formula (2).
本反応で使用できる不活性溶媒としては、本反応の進行を著しく阻害しないものであればよく、例えば、ペンタン、ヘキサン、シクロヘキサン等の鎖状又は環状飽和炭化水素類、ベンゼン、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン、ジクロロベンゼン等のハロゲン化芳香族炭化水素類、ジエチルエーテル、メチルターシャリーブチルエーテル、ジオキサン、テトラヒドロフラン等の鎖状又は環状エーテル類等の不活性溶媒、アセトニトリル、プロピオニトリル等のニトリル類、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‐イミダゾリジノン等の非プロトン性極性溶媒、メタノール、エタノール、プロパノール、ブタノール、2‐プロパノール等のアルコール類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。その使用量は、一般式(2)で表される化合物1モルに対して通常0.1~100Lの範囲から適宜選択すればよい。
Inert solvents that can be used in this reaction may be those that do not significantly inhibit the progress of this reaction, such as linear or cyclic saturated hydrocarbons such as pentane, hexane, cyclohexane, benzene, toluene, xylene, etc. Aromatic hydrocarbons, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, inert solvents such as chain or cyclic ethers such as diethyl ether, methyl tert-butyl ether, dioxane, and tetrahydrofuran, acetonitrile, propionitrile Nitriles such as N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, aprotic polar solvents such as 1,3-dimethyl-2-imidazolidinone, methanol, ethanol, propanol, butanol, 2 Examples include alcohols such as -propanol, and these inert solvents can be used alone or in combination of two or more. The amount used may be appropriately selected from the range of usually 0.1 to 100 L per mol of the compound represented by the general formula (2).
本反応は等モル反応であるので、各化合物を等モル使用すればよいが、いずれかの化合物を過剰に用いることもできる。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良く、反応時間は反応規模、反応温度等により変化し、一定ではないが、通常数分~48時間の範囲で適宜選択すれば良い。反応終了後、目的物を含む反応系から目的物を常法により単離すれば良く、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。
Since this reaction is an equimolar reaction, it is sufficient to use equimolar amounts of each compound, but it is also possible to use an excess of any one of the compounds. 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., and is not constant, but is usually in the range of several minutes to 48 hours. You can choose as appropriate. 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.
出発原料の製造方法
本発明の一般式(1‐1)及び(1‐2)で表される化合物の出発原料である一般式(2)で表される化合物は、Tetrahedron Letters,1995,36,3659、又はJournal of Heterocyclic Chemistry,2017,54,1318記載の方法により、又はこれに準じて製造することができる。 Method for producing starting material The compound represented by general formula (2), which is the starting material for the compounds represented by general formulas (1-1) and (1-2) of the present invention, is prepared from Tetrahedron Letters, 1995, 36, 3659 or Journal of Heterocyclic Chemistry, 2017, 54, 1318, or according to the method described therein.
本発明の一般式(1‐1)及び(1‐2)で表される化合物の出発原料である一般式(2)で表される化合物は、Tetrahedron Letters,1995,36,3659、又はJournal of Heterocyclic Chemistry,2017,54,1318記載の方法により、又はこれに準じて製造することができる。 Method for producing starting material The compound represented by general formula (2), which is the starting material for the compounds represented by general formulas (1-1) and (1-2) of the present invention, is prepared from Tetrahedron Letters, 1995, 36, 3659 or Journal of Heterocyclic Chemistry, 2017, 54, 1318, or according to the method described therein.
以下に本発明の一般式(1)で表される化合物の代表例を第1表に例示するが、本発明は、これらに限定されるものではない。下記の表において、「Me」はメチル基、「Et」はエチル基、「c‐Pr」はシクロプロピル基、「n‐Bu」はノルマルブチル基、「c‐Hex」はシクロヘキシル基、「Ph」はフェニル基、「Bn」はベンジル基を示す。物性は融点(℃)又はH1‐NMRを示す。H1‐NMRデータは、第2表に示す。
Representative examples of the compounds represented by the general formula (1) of the present invention are shown below in Table 1, but the present invention is not limited thereto. In the table below, "Me" is a methyl group, "Et" is an ethyl group, "c-Pr" is a cyclopropyl group, "n-Bu" is a n-butyl group, "c-Hex" is a cyclohexyl group, "Ph ” represents a phenyl group, and “Bn” represents a benzyl group. Physical properties indicate melting point (°C) or H 1 -NMR. H 1 -NMR data are shown in Table 2.
本発明の一般式(1)で表される化合物又はその塩類を有効成分として含有する有害生物防除剤は、農園芸用害虫防除剤、動物用外部寄生虫防除剤及び動物用内部寄生虫防除剤として適用できる。農園芸用害虫防除剤としては、水稲、果樹、野菜、その他の作物及び花卉類を加害する各種農林、園芸、貯穀害虫や衛生害虫或いは線虫類等の害虫防除に適用できる。
また、本発明の一般式(1)で表される化合物又はその塩類を有効成分として含有する農園芸用殺虫剤は、各種の省力的な施用方法に適した物性、浸透移行活性、適切な土壌残留性など環境安全性に優れる。
さらに、本発明の一般式(1)で表される化合物又はその塩類を有効成分として含有する農園芸用殺虫剤は、天敵・セイヨウミツバチ、マルハナバチなどの有用昆虫・ユスリカなどの環境生物への影響が少ない。 Pest control agents containing the compound represented by general formula (1) or its salts as an active ingredient of the present invention include agricultural and horticultural pest control agents, ectoparasite control agents for animals, and endoparasite control agents for animals. Can be applied as As an agricultural and horticultural pest control agent, it can be applied to control various agricultural and forestry, horticultural, grain storage pests, sanitary pests, nematodes, and other pests that damage paddy rice, fruit trees, vegetables, other crops, and flowers.
In addition, agricultural and horticultural insecticides containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention have physical properties suitable for various labor-saving application methods, systemic transfer activity, and suitable soil Excellent environmental safety such as persistence.
Furthermore, the agricultural and horticultural insecticides containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention have no effect on natural enemies, useful insects such as the European honey bee and bumble bee, and environmental organisms such as midges. Less is.
また、本発明の一般式(1)で表される化合物又はその塩類を有効成分として含有する農園芸用殺虫剤は、各種の省力的な施用方法に適した物性、浸透移行活性、適切な土壌残留性など環境安全性に優れる。
さらに、本発明の一般式(1)で表される化合物又はその塩類を有効成分として含有する農園芸用殺虫剤は、天敵・セイヨウミツバチ、マルハナバチなどの有用昆虫・ユスリカなどの環境生物への影響が少ない。 Pest control agents containing the compound represented by general formula (1) or its salts as an active ingredient of the present invention include agricultural and horticultural pest control agents, ectoparasite control agents for animals, and endoparasite control agents for animals. Can be applied as As an agricultural and horticultural pest control agent, it can be applied to control various agricultural and forestry, horticultural, grain storage pests, sanitary pests, nematodes, and other pests that damage paddy rice, fruit trees, vegetables, other crops, and flowers.
In addition, agricultural and horticultural insecticides containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention have physical properties suitable for various labor-saving application methods, systemic transfer activity, and suitable soil Excellent environmental safety such as persistence.
Furthermore, the agricultural and horticultural insecticides containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention have no effect on natural enemies, useful insects such as the European honey bee and bumble bee, and environmental organisms such as midges. Less is.
上記害虫又は線虫類等として以下のものが例示される。
鱗翅目(チョウ目)害虫として例えば、アオイラガ(Parasa consocia)、アカキリバ(Anomis mesogona)、アゲハ(Papilio xuthus)、アズキサヤムシガ(Matsumuraeses azukivora)、アズキノメイガ(Ostrinia scapulalis)、アフリカヨトウ(Spodoptera exempta)、アメリカシロヒトリ(Hyphantria cunea)、アワノメイガ(Ostrinia furnacalis)、アワヨトウ(Pseudaletia separata)、イガ(Tinea translucens)、イグサシンムシガ(Bactra furfuryla)、イチモンジセセリ又はイネツトムシ(Parnara guttata)、イネタテハマキ(Marasmia exigua)、イネヨトウ(Sesamia inferens)、イモキバガ(Brachmia triannulella)、イラガ(Monema flavescens)、イラクサギンウワバ(Trichoplusia ni)、ウコンノメイガ(Pleuroptya ruralis)、ウメエダシャク(Cystidia couaggaria)、ウラナミシジミ(Lampides boeticus)、オオスカシバ(Cephonodes hylas)、オオタバコガ(Helicoverpa armigera)、オオトビモンシャチホコ(Phalerodonta manleyi)、オオミノガ(Eumeta japonica)、オオモンシロチョウ(Pieris brassicae)、オビカレハ(Malacosoma neustria testacea)、カキノヘタムシガ(Stathmopoda masinissa)、カキホソガ(Cuphodes diospyrosella)、カクモンハマキ(Archips xylosteanus)、カブラヤガ(Agrotis segetum)、カンショシンクイハマキ(Tetramoera schistaceana)、キアゲハ(Papilio machaon hippocrates)、キマダラコウモリ(Endoclyta sinensis)、ギンモンハモグリガ(Lyonetia prunifoliella)、キンモンホソガ(Phyllonorycter ringoneella)、クリミガ(Cydia kurokoi)、クリミドリシンクイガ(Eucoenogenes aestuosa)、グレープベリーモス(Lobesia botrana)、クロシタアオイラガ(Latoia sinica)、クロフタモンマダラメイガ(Euzophera batangensis)、クワイホソハマキ(Phalonidia mesotypa)、クワゴマダラヒトリ(Spilosoma imparilis)、クワノメイガ(Glyphodes pyloalis)、クワヒメハマキ(Olethreutes mori)、コイガ(Tineola bisselliella)、コウモリガ(Endoclyta excrescens)、コクガ(Nemapogon granellus)、コスカシバ(Synanthedon hector)、コドリンガ(Cydia pomonella)、コナガ(Plutella xylostella)、コブノメイガ(Cnaphalocrocis medinalis)、サザンピンクボーラー(Sesamia calamistis)、サンカメイガ(Scirpophaga incertulas)、シバツトガ(Pediasia teterrellus)、ジャガイモガ(Phthorimaea operculella)、シャチホコガ(Stauropus fagi persimilis)、シロイチモジマダラメイガ(Etiella zinckenella)、シロイチモジヨトウ(Spodoptera exigua)、シロテンコウモリ(Palpifer sexnotata)、シロナヨトウ(Spodoptera mauritia)、イネシロオオメイガ(Scirpophaga innotata)、シロモンヤガ(Xestia c-nigrum)、スジキリヨトウ(Spodoptera depravata)、スジコナマダラメイガ(Ephestia kuehniella)、スモモエダシャク(Angerona prunaria)、セグロシャチホコ(Clostera anastomosis)、ソイビーンルーパー(Pseudoplusia includens)、ダイズサヤムシガ(Matsumuraeses falcana)、タバコガ(Helicoverpa assulta)、タマナギンウワバ(Autographa nigrisigna)、タマナヤガ(Agrotis ipsilon)、チャドクガ(Euproctis pseudoconspersa)、チャノコカクモンハマキ(Adoxophyes orana)、チャノホソガ(Caloptilia theivora)、チャハマキ(Homona magnanima)、チャマダラメイガ(Ephestia elutella)、チャミノガ(Eumeta minuscula)、ツマアカシャチホコ(Clostera anachoreta)、ツメクサガ(Heliothis maritima)、テングハマキ(Sparganothis pilleriana)、トウモロコシメイガ(Busseola fusca)、ドクガ(Euproctis subflava)、トビモンオオエダシャク(Biston robustum)、トマトフルーツワーム(Heliothis zea)、ナカジロシタバ(Aedia leucomelas)、ナシイラガ(Narosoideus flavidorsalis)、ナシケンモン(Viminia rumicis)、ナシチビガ(Bucculatrix pyrivorella)、ナシヒメシンクイ(Grapholita molesta)、ナシホソガ(Spulerina astaurota)、ナシマダラメイガ(Ectomyelois pyrivorella)、ニカメイガ(Chilo suppressalis)、ネギコガ(Acrolepiopsis sapporensis)、ノシメマダラメイガ(Plodia interpunctella)、ハイマダラノメイガ(Hellula undalis)、バクガ(Sitotroga cerealella)、ハスモンヨトウ(Spodoptera litura)、ハマキガの一種(Eucosma aporema)、バラハマキ(Acleris comariana)、ヒメクロイラガ(Scopelodes contractus)、ヒメシロモンドクガ(Orgyia thyellina)、フォールアーミーワーム(Spodoptera frugiperda)、フキノメイガ(Ostrinia zaguliaevi)、フタオビコヤガ(Naranga aenescens)、フタテンカギバモドキ(Andraca bipunctata)、ブドウスカシバ(Paranthrene regalis)、ブドウスズメ(Acosmeryx castanea)、ブドウハモグリガ(Phyllocnistis toparcha)、ブドウヒメハマキ(Endopiza viteana)、ブドウホソハマキ(Eupoecillia ambiguella)、ベルベットビーンキャタピラー(Anticarsia gemmatalis)、ホソバハイイロハマキ(Cnephasia cinereipalpana)、マイマイガ(Lymantria dispar)、マツカレハ(Dendrolimus spectabilis)、マメシンクイガ(Leguminivora glycinivorella)、マメノメイガ(Maruca testulalis)、マメヒメサヤムシガ(Matsumuraeses phaseoli)、マメホソガ(Caloptilia soyella)、ミカンハモグリガ(Phyllocnistis citrella)、マエウスキノメイガ(Omiodes indicate)、ミダレカクモンハマキ(Archips fuscocupreanus)、ミツモンキンウワバ(Acanthoplusia agnata)、ミノガ(Bambalina sp.)、モモシンクイガ(Carposina niponensis)、モモノゴマダラノメイガ(Conogethes punctiferalis)、モモスカシバ類(Synanthedon sp.)、モモハモグリガ(Lyonetia clerkella)、モンキアゲハ(Papilio helenus)、モンキチョウ(Colias erate poliographus)、モンクロシャチホコ(Phalera flavescens)、モンシロチョウ(Pieris rapae crucivora)、モンシロチョウ(Pieris rapae)等のシロチョウ類、モンシロドクガ(Euproctis similis)、ヤマノイモコガ(Acrolepiopsis suzukiella)、ヨーロピアンコーンボーラー(Ostrinia nubilalis)、ヨトウガ(Mamestra brassicae)、ヨモギエダシャク(Ascotis selenaria)、ヨモギオオホソハマキ(Phtheochroides clandestina)、リンゴオオハマキ(Hoshinoa adumbratana)、リンゴカレハ(Odonestis pruni japonensis)、リンゴケンモン(Triaena intermedia)、リンゴコカクモンハマキ(Adoxophyes orana fasciata)、リンゴコシンクイ(Grapholita inopinata)、リンゴシロヒメハマキ(Spilonota ocellana)、リンゴハイイロハマキ(Spilonota lechriaspis)、リンゴハマキクロバ(Illiberis pruni)、リンゴヒメシンクイ(Argyresthia conjugella)、リンゴホソガ(Caloptilia zachrysa)、リンゴモンハマキ(Archips breviplicanus)、ワタアカキリバ(Anomis flava)、ワタアカミムシ(Pectinophora gossypiella)、ワタノメイガ(Notarcha derogata)、ワタヘリクロノメイガ(Diaphania indica)、ニセアメリカタバコガ(Heliothis virescens)、及びワタリンガ(Earias cupreoviridis)等が挙げられる。 The following are exemplified as the pests or nematodes.
Examples of Lepidoptera (Lepidoptera) pests include Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, Spodoptera exempta, and American white flycatcher. (Hyphantria cunea), Ostrinia furnacalis, Pseudaletia separata, Tinea translucens, Bactra furfuryla, Parnara guttata, Marasmia exigua, Sesamia inferens, potato Kibaga (Brachmia triannullella), Monema flavescens, Trichoplusia ni, Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Cephonodes hylas, Helicoverpa armigera , Phalerodonta manleyi, Eumeta japonica, Pieris brassicae, Malacosoma neustria testacea, Stathmopoda masinissa, Cuphodes diospyrosella, Archips xylosteanus, Archips xylosteanus Ga( Agrotis segetum), Tetramoera schistaceana, Papilio machaon hippocrates, Endoclyta sinensis, Lyonetia prunifoliella, Phyllonorycter ringoneella, Cydia kurokoi Eucoenogenes aestuosa, Grapeberry moss (Lobesia botrana), Latoia sinica, Euzophera batangensis, Phalonidia mesotypa, Spilosoma imparilis, Glyphodes pyloalis, Olethreutes mori, Tineola bisselliella, Endoclyta excrescens, Nemapogon granellus, Synanthedon hector, Cydia pomonella, Plutella xylostella, Cnaphalocrocis medinalis, Southern pink Borer (Sesamia calamistis), Scirpophaga incertulas, Pediasia teterrellus, potato moth (Phthorimaea operculella), Stauropus fagi persimilis, Etiella zinckenella, Spodoptera exigua, white marten Bat (Palpifer sexnotata), Spodoptera mauritia, Scirpophaga innotata, Xestia c-nigrum, Spodoptera depravata, Ephestia kuehniella, Angelona prunaria , Clostera anastomosis, Pseudoplusia includens, Matsumuraeses falcana, Helicoverpa assulta, Autographa nigrisigna, Agrotis ipsilon, Euproctis pseudoconspersa, and Euproctis pseudoconspersa. Adoxophyes orana), Caloptilia theivora, Homona magnanima, Ephestia elutella, Eumeta minuscula, Clostera anachoreta, Heliothis maritima, Sparganothis pilleriana, Busseola fusca, Euproctis subflava, Biston robustum, Heliothis zea, Aedia leucomelas, Narosoideus flavidorsalis, Viminia rumicis, Biston robustum Bucculatrix pyrivorella), Grapholita molesta, Spulerina astaurota, Ectomyelois pyrivorella, Chilo suppressalis, Acrolepiopsis sapporensis, Plodia interpunctella, Hellula undalis ), Sitotroga cerealella, Spodoptera litura, Eucosma aporema, Acleris comariana, Scopelodes contractus, Orgyia thyellina, Spodoptera frugiperda, Ostrinia zaguliaevi, Naranga aenescens, Andraca bipunctata, Paranthrene regalis, Acosmeryx castanea, Phyllocnistis toparcha, Endopiza viteana, Eupoecilia ambiguella, Anticarsia gemmatalis, Cnephasia cinereipalpana, Lymantria dispar, Dendrolimus spectabilis, Leguminivora glycinivorella, Maruca testulalis, Cnephasia cinereipalpana Matsumuraeses phaseoli, Caloptilia soyella, Phyllocnistis citrella, Omiodes indicate, Archips fuscocupreanus, Acanthoplusia agnata, Bambalina sp.), Carposina niponensis, Conogethes punctiferalis, Synanthedon sp., Lyonetia clerkella, Papilio helenus, Colias erate poliographus, Phalera Flavescens), Pieris rapae crucivora, Pieris rapae and other white butterflies, Euproctis similis, Acrolepiopsis suzukiella, European corn borer (Ostrinia nubilalis), Armyworm moth (Mamestra brassicae), Artemisia suzukiella (Euproctis similis), Acrolepiopsis suzukiella Ascotis selenaria), Phtheochroides clandestina, Hoshinoa adumbratana, Odonestis pruni japonensis, Triaena intermedia, Adoxophyes orana fasciata, Grapholita inopinata), Spilonota ocellana, Spilonota lechriaspis, Illiberis pruni, Argyrestia conjugella, Caloptilia zachrysa, Archips breviplicanus , Anomis flava, Pectinophora gossypiella, Notarcha derogata, Diaphania indica, Heliothis virescens, and Earias cupreoviridis.
鱗翅目(チョウ目)害虫として例えば、アオイラガ(Parasa consocia)、アカキリバ(Anomis mesogona)、アゲハ(Papilio xuthus)、アズキサヤムシガ(Matsumuraeses azukivora)、アズキノメイガ(Ostrinia scapulalis)、アフリカヨトウ(Spodoptera exempta)、アメリカシロヒトリ(Hyphantria cunea)、アワノメイガ(Ostrinia furnacalis)、アワヨトウ(Pseudaletia separata)、イガ(Tinea translucens)、イグサシンムシガ(Bactra furfuryla)、イチモンジセセリ又はイネツトムシ(Parnara guttata)、イネタテハマキ(Marasmia exigua)、イネヨトウ(Sesamia inferens)、イモキバガ(Brachmia triannulella)、イラガ(Monema flavescens)、イラクサギンウワバ(Trichoplusia ni)、ウコンノメイガ(Pleuroptya ruralis)、ウメエダシャク(Cystidia couaggaria)、ウラナミシジミ(Lampides boeticus)、オオスカシバ(Cephonodes hylas)、オオタバコガ(Helicoverpa armigera)、オオトビモンシャチホコ(Phalerodonta manleyi)、オオミノガ(Eumeta japonica)、オオモンシロチョウ(Pieris brassicae)、オビカレハ(Malacosoma neustria testacea)、カキノヘタムシガ(Stathmopoda masinissa)、カキホソガ(Cuphodes diospyrosella)、カクモンハマキ(Archips xylosteanus)、カブラヤガ(Agrotis segetum)、カンショシンクイハマキ(Tetramoera schistaceana)、キアゲハ(Papilio machaon hippocrates)、キマダラコウモリ(Endoclyta sinensis)、ギンモンハモグリガ(Lyonetia prunifoliella)、キンモンホソガ(Phyllonorycter ringoneella)、クリミガ(Cydia kurokoi)、クリミドリシンクイガ(Eucoenogenes aestuosa)、グレープベリーモス(Lobesia botrana)、クロシタアオイラガ(Latoia sinica)、クロフタモンマダラメイガ(Euzophera batangensis)、クワイホソハマキ(Phalonidia mesotypa)、クワゴマダラヒトリ(Spilosoma imparilis)、クワノメイガ(Glyphodes pyloalis)、クワヒメハマキ(Olethreutes mori)、コイガ(Tineola bisselliella)、コウモリガ(Endoclyta excrescens)、コクガ(Nemapogon granellus)、コスカシバ(Synanthedon hector)、コドリンガ(Cydia pomonella)、コナガ(Plutella xylostella)、コブノメイガ(Cnaphalocrocis medinalis)、サザンピンクボーラー(Sesamia calamistis)、サンカメイガ(Scirpophaga incertulas)、シバツトガ(Pediasia teterrellus)、ジャガイモガ(Phthorimaea operculella)、シャチホコガ(Stauropus fagi persimilis)、シロイチモジマダラメイガ(Etiella zinckenella)、シロイチモジヨトウ(Spodoptera exigua)、シロテンコウモリ(Palpifer sexnotata)、シロナヨトウ(Spodoptera mauritia)、イネシロオオメイガ(Scirpophaga innotata)、シロモンヤガ(Xestia c-nigrum)、スジキリヨトウ(Spodoptera depravata)、スジコナマダラメイガ(Ephestia kuehniella)、スモモエダシャク(Angerona prunaria)、セグロシャチホコ(Clostera anastomosis)、ソイビーンルーパー(Pseudoplusia includens)、ダイズサヤムシガ(Matsumuraeses falcana)、タバコガ(Helicoverpa assulta)、タマナギンウワバ(Autographa nigrisigna)、タマナヤガ(Agrotis ipsilon)、チャドクガ(Euproctis pseudoconspersa)、チャノコカクモンハマキ(Adoxophyes orana)、チャノホソガ(Caloptilia theivora)、チャハマキ(Homona magnanima)、チャマダラメイガ(Ephestia elutella)、チャミノガ(Eumeta minuscula)、ツマアカシャチホコ(Clostera anachoreta)、ツメクサガ(Heliothis maritima)、テングハマキ(Sparganothis pilleriana)、トウモロコシメイガ(Busseola fusca)、ドクガ(Euproctis subflava)、トビモンオオエダシャク(Biston robustum)、トマトフルーツワーム(Heliothis zea)、ナカジロシタバ(Aedia leucomelas)、ナシイラガ(Narosoideus flavidorsalis)、ナシケンモン(Viminia rumicis)、ナシチビガ(Bucculatrix pyrivorella)、ナシヒメシンクイ(Grapholita molesta)、ナシホソガ(Spulerina astaurota)、ナシマダラメイガ(Ectomyelois pyrivorella)、ニカメイガ(Chilo suppressalis)、ネギコガ(Acrolepiopsis sapporensis)、ノシメマダラメイガ(Plodia interpunctella)、ハイマダラノメイガ(Hellula undalis)、バクガ(Sitotroga cerealella)、ハスモンヨトウ(Spodoptera litura)、ハマキガの一種(Eucosma aporema)、バラハマキ(Acleris comariana)、ヒメクロイラガ(Scopelodes contractus)、ヒメシロモンドクガ(Orgyia thyellina)、フォールアーミーワーム(Spodoptera frugiperda)、フキノメイガ(Ostrinia zaguliaevi)、フタオビコヤガ(Naranga aenescens)、フタテンカギバモドキ(Andraca bipunctata)、ブドウスカシバ(Paranthrene regalis)、ブドウスズメ(Acosmeryx castanea)、ブドウハモグリガ(Phyllocnistis toparcha)、ブドウヒメハマキ(Endopiza viteana)、ブドウホソハマキ(Eupoecillia ambiguella)、ベルベットビーンキャタピラー(Anticarsia gemmatalis)、ホソバハイイロハマキ(Cnephasia cinereipalpana)、マイマイガ(Lymantria dispar)、マツカレハ(Dendrolimus spectabilis)、マメシンクイガ(Leguminivora glycinivorella)、マメノメイガ(Maruca testulalis)、マメヒメサヤムシガ(Matsumuraeses phaseoli)、マメホソガ(Caloptilia soyella)、ミカンハモグリガ(Phyllocnistis citrella)、マエウスキノメイガ(Omiodes indicate)、ミダレカクモンハマキ(Archips fuscocupreanus)、ミツモンキンウワバ(Acanthoplusia agnata)、ミノガ(Bambalina sp.)、モモシンクイガ(Carposina niponensis)、モモノゴマダラノメイガ(Conogethes punctiferalis)、モモスカシバ類(Synanthedon sp.)、モモハモグリガ(Lyonetia clerkella)、モンキアゲハ(Papilio helenus)、モンキチョウ(Colias erate poliographus)、モンクロシャチホコ(Phalera flavescens)、モンシロチョウ(Pieris rapae crucivora)、モンシロチョウ(Pieris rapae)等のシロチョウ類、モンシロドクガ(Euproctis similis)、ヤマノイモコガ(Acrolepiopsis suzukiella)、ヨーロピアンコーンボーラー(Ostrinia nubilalis)、ヨトウガ(Mamestra brassicae)、ヨモギエダシャク(Ascotis selenaria)、ヨモギオオホソハマキ(Phtheochroides clandestina)、リンゴオオハマキ(Hoshinoa adumbratana)、リンゴカレハ(Odonestis pruni japonensis)、リンゴケンモン(Triaena intermedia)、リンゴコカクモンハマキ(Adoxophyes orana fasciata)、リンゴコシンクイ(Grapholita inopinata)、リンゴシロヒメハマキ(Spilonota ocellana)、リンゴハイイロハマキ(Spilonota lechriaspis)、リンゴハマキクロバ(Illiberis pruni)、リンゴヒメシンクイ(Argyresthia conjugella)、リンゴホソガ(Caloptilia zachrysa)、リンゴモンハマキ(Archips breviplicanus)、ワタアカキリバ(Anomis flava)、ワタアカミムシ(Pectinophora gossypiella)、ワタノメイガ(Notarcha derogata)、ワタヘリクロノメイガ(Diaphania indica)、ニセアメリカタバコガ(Heliothis virescens)、及びワタリンガ(Earias cupreoviridis)等が挙げられる。 The following are exemplified as the pests or nematodes.
Examples of Lepidoptera (Lepidoptera) pests include Parasa consocia, Anomis mesogona, Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, Spodoptera exempta, and American white flycatcher. (Hyphantria cunea), Ostrinia furnacalis, Pseudaletia separata, Tinea translucens, Bactra furfuryla, Parnara guttata, Marasmia exigua, Sesamia inferens, potato Kibaga (Brachmia triannullella), Monema flavescens, Trichoplusia ni, Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Cephonodes hylas, Helicoverpa armigera , Phalerodonta manleyi, Eumeta japonica, Pieris brassicae, Malacosoma neustria testacea, Stathmopoda masinissa, Cuphodes diospyrosella, Archips xylosteanus, Archips xylosteanus Ga( Agrotis segetum), Tetramoera schistaceana, Papilio machaon hippocrates, Endoclyta sinensis, Lyonetia prunifoliella, Phyllonorycter ringoneella, Cydia kurokoi Eucoenogenes aestuosa, Grapeberry moss (Lobesia botrana), Latoia sinica, Euzophera batangensis, Phalonidia mesotypa, Spilosoma imparilis, Glyphodes pyloalis, Olethreutes mori, Tineola bisselliella, Endoclyta excrescens, Nemapogon granellus, Synanthedon hector, Cydia pomonella, Plutella xylostella, Cnaphalocrocis medinalis, Southern pink Borer (Sesamia calamistis), Scirpophaga incertulas, Pediasia teterrellus, potato moth (Phthorimaea operculella), Stauropus fagi persimilis, Etiella zinckenella, Spodoptera exigua, white marten Bat (Palpifer sexnotata), Spodoptera mauritia, Scirpophaga innotata, Xestia c-nigrum, Spodoptera depravata, Ephestia kuehniella, Angelona prunaria , Clostera anastomosis, Pseudoplusia includens, Matsumuraeses falcana, Helicoverpa assulta, Autographa nigrisigna, Agrotis ipsilon, Euproctis pseudoconspersa, and Euproctis pseudoconspersa. Adoxophyes orana), Caloptilia theivora, Homona magnanima, Ephestia elutella, Eumeta minuscula, Clostera anachoreta, Heliothis maritima, Sparganothis pilleriana, Busseola fusca, Euproctis subflava, Biston robustum, Heliothis zea, Aedia leucomelas, Narosoideus flavidorsalis, Viminia rumicis, Biston robustum Bucculatrix pyrivorella), Grapholita molesta, Spulerina astaurota, Ectomyelois pyrivorella, Chilo suppressalis, Acrolepiopsis sapporensis, Plodia interpunctella, Hellula undalis ), Sitotroga cerealella, Spodoptera litura, Eucosma aporema, Acleris comariana, Scopelodes contractus, Orgyia thyellina, Spodoptera frugiperda, Ostrinia zaguliaevi, Naranga aenescens, Andraca bipunctata, Paranthrene regalis, Acosmeryx castanea, Phyllocnistis toparcha, Endopiza viteana, Eupoecilia ambiguella, Anticarsia gemmatalis, Cnephasia cinereipalpana, Lymantria dispar, Dendrolimus spectabilis, Leguminivora glycinivorella, Maruca testulalis, Cnephasia cinereipalpana Matsumuraeses phaseoli, Caloptilia soyella, Phyllocnistis citrella, Omiodes indicate, Archips fuscocupreanus, Acanthoplusia agnata, Bambalina sp.), Carposina niponensis, Conogethes punctiferalis, Synanthedon sp., Lyonetia clerkella, Papilio helenus, Colias erate poliographus, Phalera Flavescens), Pieris rapae crucivora, Pieris rapae and other white butterflies, Euproctis similis, Acrolepiopsis suzukiella, European corn borer (Ostrinia nubilalis), Armyworm moth (Mamestra brassicae), Artemisia suzukiella (Euproctis similis), Acrolepiopsis suzukiella Ascotis selenaria), Phtheochroides clandestina, Hoshinoa adumbratana, Odonestis pruni japonensis, Triaena intermedia, Adoxophyes orana fasciata, Grapholita inopinata), Spilonota ocellana, Spilonota lechriaspis, Illiberis pruni, Argyrestia conjugella, Caloptilia zachrysa, Archips breviplicanus , Anomis flava, Pectinophora gossypiella, Notarcha derogata, Diaphania indica, Heliothis virescens, and Earias cupreoviridis.
半翅目(カメムシ目)害虫として例えば、アオクサカメムシ(Nezara antennata)、アカスジカスミカメ(Stenotus rubrovittatus)、アカスジカメムシ(Graphosoma rubrolineatum)、アカヒゲホソミドリカスミカメ(Trigonotylus coelestialium)等、アカヒメヘリカメムシ(Aeschynteles maculatus)、アカホシカスミカメ(Creontiades pallidifer)、アカホシカメムシ(Dysdercus cingulatus)、アカホシマルカイアガラムシ(Chrysomphalus ficus)、アカマルカイガラムシ(Aonidiella aurantii)、アブラゼミ(Graptopsaltria nigrofuscata)、アメリカコバネナガカメムシ(Blissusleucopterus)、イセリヤカイガラムシ(Icerya purchasi)、イチモンジカメムシ(Piezodorus hybneri)、イネカメムシ(Lagynotomus elongatus)、イネキイロヒメヨコバイ(Thaia subrufa)、イネクロカメムシ(Scotinophara lurida)、イバラヒゲナガアブラムシ(Sitobion ibarae)、イワサキカメムシ(Stariodes iwasakii)、ウスイロマルカイガラムシ(Aspidiotus destructor)、ウスモンミドリカスミカメ(Taylorilygus pallidulus)、ウメコブアブラムシ(Myzusmumecola)、ウメシロカイガラムシ(Pseudaulacaspis prunicola)、エンドウヒゲナガアブラムシ(Acyrthosiphon pisum)、オオクモヘリカメムシ(Anacanthocoris striicornis)、オオクロトビカスミカメ(Ectometopterus micantulus)、オオトゲシラホシカメムシ(Eysarcoris lewisi)、オオヘリカメムシ(Molipteryx fuliginosa)、オオヨコバイ(Cicadella viridis)、オカボノアカアブラムシ(Rhopalosophum rufiabdominalis)、オリーブカタカイガラムシ(Saissetia oleate)、オンシツコナジラミ(Trialeurodes vaporariorum)、カシヒメヨコバイ(Aguriahana quercus)、カスミカメムシ類(Lygus spp.)、カバワタフキマダラアブラムシ(Euceraphis punctipennis)、カンキツカイガラムシ(Andaspis kashicola)、カンキツカタカイガラムシ(Coccus pseudomagnoliarum)、カンシャコバネナガカメムシ(Cavelerius saccharivorus)、キクグンバイ(Galeatus spinifrons)、キクヒメヒゲナガアブラムシ(Macrosiphoniella sanborni)、キマルカイガラムシ(Aonidiella citrina)、クサギカメムシ(Halyomorpha mista)、クスグンバイ(Stephanitis fasciicarina)、クストガリキジラミ(Trioza camphorae)、クモヘリカメムシ(Leptocorisa chinensis)、クリトガリキジラミ(Trioza quercicola)、クルミグンバイ(Uhlerites latius)、グレープリーフホッパー(Erythroneura comes)、クロアシホソナガカメムシ(Paromius exiguus)、クロカタマルカイガラムシ(Duplaspidiotus claviger)、クロスジツマグロヨコバイ(Nephotettix nigropictus)、クロトビカスミカメ(Halticiellus insularis)、クロフツノウンカ(Perkinsiella saccharicida)、クロリンゴキジラミ(Psylla malivorella)、クワキジラミ(Anomomeura mori)、クワコナカイガラムシ(Pseudococcus longispinis)、クワシロカイガラムシ(Pseudaulacaspis pentagona)、クワワタカイガラムシ(Pulvinaria kuwacola)、コアオカスミカメ(Apolygus lucorum)、コバネヒョウタンナガカメムシ(Togo hemipterus)、コミカンアブラムシ(Toxoptera aurantii)、サトウキビコナカイガラムシ(Saccharicoccus sacchari)、サトウキビネワタムシ(Geoica lucifuga)、サトウノウスイロウンカ(Numata muiri)、サンホーゼカイガラムシ(Comstockaspis perniciosa)、シトラススノースケール(Unaspis citri)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、シラホシカメムシ(Eysarcoris ventralis)、シルバーリーフコナジラミ(Bemisia argentifolii)、シロオオヨコバイ(Cicadella spectra)、シロマルカイガラムシ(Aspidiotus hederae)、スカシヒメヘリカメムシ(Liorhyssus hyalinus)、セグロヒメキジラミ(Calophya nigridorsalis)、セジロウンカ(Sogatella furcifera)、ソラマメヒゲナガアブラムシ(Megoura crassicauda)、ダイコンアブラムシ(Brevicoryne brassicae)、ダイズアブラムシ(Aphis glycines)、タイワンクモヘリカメムシ(Leptocorisa oratorius)、タイワンツマグロヨコバイ(Nephotettix virescens)、タイワンヒゲナガアブラムシ(Uroeucon formosanum)、タバコカスミカメ(Cyrtopeltis tennuis)、タバココナジラミ(Bemisia tabaci)、チャノカタカイガラムシ(Lecanium persicae)、チャノクロホシカイガラムシ(Parlatoria theae)、チャノマルカイガラムシ(Pseudaonidia paeoniae)、チャノミドリヒメヨコバイ(Empoasca onukii)、チャバネアオカメムシ(Plautia stali)、チューリップネアブラムシ(Dysaphis tulipae)、チューリップヒゲナガアブラムシ(Macrosiphum euphorbiae)、ツツジグンバイ(Stephanitis pyrioides)、ツノロウムシ(Ceroplastes ceriferus)、ツバキクロホシカイガラムシ(Parlatoria camelliae)、ツマグロアオカスミカメ(Apolygus spinolai)、ツマグロヨコバイ(Nephotettix cincticeps)、ツヤアオカメムシ(Glaucias subpunctatus)、テンサイカスミカメ(Orthotylus flavosparsus)、トウモロコシアブラムシ(Rhopalosiphum maidis)、トウモロコシウンカ(Peregrinus maidis)、トゲシラホシカメムシ(Eysarcoris parvus)、トコジラミ(Cimex lectularius)、トドキジラミ(Psylla abieti)、トビイロウンカ(Nilaparvata lugens)、トベラキジラミ(Psylla tobirae)、ナガメ(Eurydema rugosum)、ナシアブラムシ(Schizaphis piricola)、ナシキジラミ(Psylla pyricola)、ナシクロホシカイガラムシ(Parlatoreopsis pyri)、ナシグンバイ(Stephanitis nashi)、ナシコナカイガラムシ(Dysmicoccus wistariae)、ナシシロナガカイガラムシ(Lepholeucaspis japonica)、ナシマルアブラムシ(Sappaphis piri)、ニセダイコンアブラムシ(Lipaphis erysimi)、ネギアブラムシ(Neotoxoptera formosana)、ハスクビレアブラムシ(Rhopalosophum nymphaeae)、バラヒメヨコバイ(Edwardsianarosae)、ハランナガカイガラムシ(Pinnaspisaspidistrae)、ハンノキジラミ(Psylla alni)、ハンノナガヨコバイ(Speusotettix subfusculus)、ハンノヒメヨコバイ(Alnetoidia alneti)、ヒエウンカ(Sogatella panicicola)、ヒゲナガカスミカメ(Adelphocoris lineolatus)、ヒメアカホシカメムシ(Dysdercus poecilus)、ヒメクロカイガラムシ(Parlatoria ziziphi)、ヒメグンバイ(Uhlerites debile)、ヒメトビウンカ(Laodelphax striatellus)、ヒメナガメ(Eurydema pulchrum)、ヒメハリカメムシ(Cletus trigonus)、ヒメフタテンナガアワフキ(Clovia punctata)、ヒメヨコバイ類(Empoasca sp.)、ヒラタカタカイガラムシ(Coccus hesperidum)、ヒラタヒョウタンナガカメムシ(Pachybrachius luridus)、フジコナカイガラムシ(Planococcus kraunhiae)、フタスジカスミカメ(Stenotus binotatus)、フタテンヒメヨコバイ(Arboridia apicalis)、フタテンヨコバイ(Macrosteles fascifrons)、ブチヒゲカメムシ(Dolycoris baccarum)、ブチヒゲクロカスミカメ(Adelphocoris triannulatus)、ブドウネアブラムシ(Viteus vitifolii)、ホオズキカメムシ(Acanthocoris sordidus)、ホソクモヘリカメムシ(Leptocorisa acuta)、ホソコバネナガカメムシ(Macropes obnubilus)、ホソハリカメムシ(Cletus punctiger)、ホソヘリカメムシ(Riptortus clavatus)、ポテトピシリド(Paratrioza cockerelli)、マエキアワフキ(Aphrophora costalis)、マキバカスミカメ(Lygus disponsi)、マダラカスミカメ(Lygus saundersi)、マツコナカイガラムシ(Crisicoccus pini)、マツヒメヨコバイ(Empoasca abietis)、マツモトコナカイガラムシ(Crisicoccus matsumotoi)、マメアブラムシ(Aphis craccivora)、マルカメムシ(Megacopta punctatissimum)、マルシラホシカメムシ(Eysarcoris guttiger)、ミカンカキカイガラムシ(Lepidosaphes beckii)、ミカンキジラミ(Diaphorina citri)、ミカンクロアブラムシ(Toxoptera citricidus)、ミカンコナカイガラムシ(Planococcus citri)、ミカンコナジラミ(Dialeurodes citri)、ミカントゲコナジラミ(Aleurocanthus spiniferus)、ミカンヒメコナカイガラムシ(Pseudococcus citriculus)、ミカンヒメヨコバイ(Zyginella citri)、ミカンヒメワタカイガラムシ(Pulvinaria citricola)、ミカンヒラタカイガラムシ(Coccus discrepans)、ミカンマルカイガラムシ(Pseudaonidia duplex)、ミカンワタカイガラムシ(Pulvinaria aurantii)、ミズキカタカイガラムシ(Lecanium corni)、ミナミアオカメムシ(Nezara viridula)、ムギカスミカメ(Stenodema calcaratum)、ムギクビレアブラムシ(Rhopalosiphum padi)、ムギヒゲナガアブラムシ(Sitobion akebiae)、ムギミドリアブラムシ(Schizaphis graminum)、ムギヨコバイ(Sorhoanus tritici)、ムギワラギクオマルアブラムシ(Brachycaudus helichrysi)、ムラサキカメムシ(Carpocoris purpureipennis)、モモアカアブラムシ(Myzus persicae)、モモコフキアブラムシ(Hyalopterus pruni)、ヤナギアブラムシ(Aphis farinose yanagicola)、ヤナギグンバイ(Metasalis populi)、ヤノネカイガラムシ(Unaspis yanonensis)、ヤマアサキジラミ(Mesohomotoma camphorae)、ユキヤナギアブラムシ(Aphis spiraecola)、リンゴアブラムシ(Aphis pomi)、リンゴカキカイガラムシ(Lepidosaphes ulmi)、リンゴキジラミ(Psylla mali)、リンゴクロカスミカメ(Heterocordylus flavipes)、リンゴコブアブラムシ(Myzus malisuctus)、リンゴネアブラムシ(Aphidonuguis mali)、リンゴマダラヨコバイ(Orientus ishidai)、リンゴミドリアブラムシ(Ovatus malicolens)、リンゴワタムシ(Eriosoma lanigerum)、ルビーロウムシ(Ceroplastes rubens)、及びワタアブラムシ(Aphis gossypii)等が挙げられる。
Hemipteran pests include Nezara antennata, Stenotus rubrovittatus, Graphosoma rubrolineatum, Trigonotylus coelestialium, etc. Aeschynteles maculatus), Creontiades pallidifer, Dysdercus cingulatus, Chrysomphalus ficus, Aonidiella aurantii, Graptopsaltria nigrofuscata, Blissus leucopter us), Iseriya Icerya purchasi, Piezodorus hybneri, Lagynotomus elongatus, Thaia subrufa, Scotinophara lurida, Sitobion ibarae, Stariodes iwasaki i) , Aspidiotus destructor, Taylorilygus pallidulus, Myzusmumecola, Pseudaulacaspis prunicola, Acyrthosiphon pisum, Anacanthocoris striicornis , Ectometopterus micantulus, Eysarcoris lewisi, Molipteryx fuliginosa, Cicadella viridis, Rhopalosophum rufiabdominalis, Saissetia oleate, Trialeurodes vaporariorum, Aguriahana quercus, Lygus spp., Euceraphis punctipennis, Andaspis kashicola, Coccus pseudomagnoliarum, Lygus spp. Cavelerius saccharivorus, Galeatus spinifrons, Macrosiphoniella sanborni, Aonidiella citrina, Halyomorpha mista, Stephanitis fasciicarina, Trioza camphorae , spider Leptocorisa chinensis, Trioza quercicola, Uhlerites latius, Grapeleaf hopper (Erythroneura comes), Paromius exiguus, Duplaspidiotus claviger, Nephotettix nigropictus, Halticiellus insularis, Perkinsiella saccharicida, Psylla malivorella, Anomomeura mori, Pseudococcus longispinis, Pseudaulacaspi s pentagona ), Pulvinaria kuwacola, Apolygus lucorum, Togo hempterus, Toxoptera aurantii, Saccharicoccus sacchari, Geoica lucifuga , Numata muiri, Comstockaspis perniciosa, Citrus snowscale (Unaspis citri), Aulacorthum solani, Eysarcoris ventralis, Silverleaf whitefly (Bemisia argentifolii), Whitefly Cicadella spectra, Aspidiotus hederae, Liorhyssus hyalinus, Calophya nigridorsalis, Sogatella furcifera, Megoura crassicauda, Brevicoryne bras sicae ), Aphis glycines, Leptocorisa oratorius, Nephotettix virescens, Uroeucon formosanum, Cyrtopeltis tennuis, Bemisia tabaci, and tea leafhopper (Lecanium persicae), Parlatoria theae, Pseudaonidia paeoniae, Empoasca onukii, Plautia stali, Dysaphis tulipae, Tulip aphid (Macrosiphum euphorbiae), Stephanitis pyrioides, Ceroplastes ceriferus, Parlatoria camelliae, Apolygus spinolai, Nephotettix cincticeps, Glaucias subpunctatus, Sugar beet turtle ( Orthotylus flavosparsus), corn aphid (Rhopalosiphum maidis), corn planthopper (Peregrinus maidis), spiny stink bug (Eysarcoris parvus), bed bug (Cimex lectularius), brown brown planthopper (Psylla abieti), brown planthopper (Nilaparvata lugens), brown planthopper (Psylla to birae), Eurydema rugosum, Schizaphis piricola, Psylla pyricola, Parlatoreopsis pyri, Stephanitis nashi, Dysmicoccus wistariae, Lepholeucaspis japonica ) , Sappaphis piri, Lipaphis erysimi, Neotoxoptera formosana, Rhopalosophum nymphaeae, Edwardsianarosae, Pinnaspisaspidistrae, Psylla alni), Speusotettix subfusculus, Alnetoidia alneti, Sogatella panicicola, Adelphocoris lineolatus, Dysdercus poecilus, Parlatoria ziziphi, Uhlerites debile), Laodelphax striatellus, Eurydema pulchrum, Cletus trigonus, Clovia punctata, Empoasca sp., Coccus hesperidum , Pachybrachius luridus, Planococcus kraunhiae, Stenotus binotatus, Arboridia apicalis, Macrosteles fascifrons, Dolycoris baccarum, Adelphocoris triannulatus, Viteus vitifolii, Acanthocoris sordidus, Leptocorisa acuta, Macropes obnubilus, Cletus punctiger, Riptortus clavatus, Paratrioza cockerelli, Aphrophora costalis, Lygus disponsi, Lygus saundersi, Crisicoccus pini, Empoasca abietis, Crisicoccus matsumotoi, Aphis craccivora, Megacopta punctatissimum, Eysarcoris guttiger, Lepidosaphes beckii, Diaphorina citri, Toxopter a citricidus ), Planococcus citri, Dialeudes citri, Aleurocanthus spiniferus, Pseudococcus citriculus, Zyginella citri, Pulvinaria citricola , Coccus discrepans, Pseudaonidia duplex, Pulvinaria aurantii, Lecanium corni, Nezara viridula, Stenodema calcaratum, Pseudaonidia duplex Rhopalosiphum padi, Sitobion akebiae, Schizaphis graminum, Sorhoanus tritici, Brachycaudus helichrysi, Carpocoris purpureipennis, My peach aphid zus persicae) , Hyalopterus pruni, Aphis farinose yanagicola, Metasalis populi, Unaspis yanonensis, Mesohomotoma camphorae, Aphis spiraecola, Aphis pomi ), apple oyster scale insect (Lepidosaphes ulmi), apple oyster louse (Psylla mali), apple black-spotted turtle (Heterocordylus flavipes), apple knoll aphid (Myzus malisuctus), apple aphid (Aphidonuguis mali), apple leafhopper (Orientus ishidai), apple Examples include green aphid (Ovatus malicolens), apple boll beetle (Eriosoma lanigerum), ruby beetle (Ceroplastes rubens), and cotton aphid (Aphis gossypii).
鞘翅目(コウチュウ目)害虫として例えば、アオスジカミキリ(Xystrocera globosa)、アオバアリガタハネカクシ(Paederus fuscipes)、アオハナムグリ(Eucetonia roelofsi)、アズキゾウムシ(Callosobruchus chinensis)、アリモドキゾウムシ(Cylas formicarius)、アルファルファタコゾウムシ(Hypera postica)、イネゾウムシ(Echinocnemus squameus)、イネドロオイムシ(Oulema oryzae)、イネネクイハムシ(Donacia provosti)、イネミズゾウムシ(Lissorhoptrus oryzophilus)、イモサルハムシ(Colasposoma dauricum)、イモゾウムシ(Euscepes postfasciatus)、インゲンテントウ(Epilachna varivestis)、インゲンマメゾウムシ(Acanthoscelides obtectus)、ウエスタンコーンルートワーム(Diabrotica virgifera virgifera)、ウメチョッキリゾウムシ(Involvulus cupreus)、ウリハムシ(Aulacophora femoralis)、エンドウゾウムシ(Bruchus pisorum)、オオニジュウヤホシテントウ(Epilachna vigintioctomaculata)、ガイマイデオキスイ(Carpophilus dimidiatus)、カメノコハムシ(Cassida nebulosa)、キアシノミハムシ(Luperomorpha tunebrosa)、キスジノミハムシ(Phyllotreta striolata)、キボシカミキリ(Psacothea hilaris)、キマダラカミキリ(Aeolesthes chrysothrix)、クリシギゾウムシ(Curculio sikkimensis)、クリヤケシキスイ(Carpophilus hemipterus)、コアオハナムグリ(Oxycetonia jucunda)、コーンルートワーム類(Diabrotica spp.)、コガネムシ(Mimela splendens)、コクゾウムシ(Sitophilus zeamais)、コクヌストモドキ(Tribolium castaneum)、ココクゾウムシ(Sitophilus oryzae)、コヒメコクヌストモドキ(Palorus subdepressus)、コフキコガネ(Melolontha japonica)、ゴマダラカミキリ(Anoplophora malasiaca)、ゴミムシダマシ(Neatus picipes)、コロラドハムシ(Leptinotarsa decemlineata)、サザンコーンルートワーム(Diabrotica undecimpunctata howardi)、シバオサゾウムシ(Sphenophorus venatus)、ジュウシホシクビナガハムシ(Crioceris quatuordecimpunctata)、スモモゾウムシ(Conotrachelus nenuphar)、ダイコンサルゾウムシ(Ceuthorhynchidius albosuturalis)、ダイコンハムシ(Phaedon brassicae)、タバコシバンムシ(Lasioderma serricorne)、チビコフキゾウムシ(Sitona japonicus)、チャイロコガネ(Adoretus tenuimaculatus)、チャイロコメノゴミムシダマシ(Tenebrio molitor)、チャイロサルハムシ(Basilepta balyi)、ツメクサタコゾウムシ(Hypera nigrirostris)、テンサイトビハムシ(Chaetocnema concinna)、ドウガネブイブイ(Anomala cuprea)、ナガチャコガネ(Heptophylla picea)、ニジュウヤホシテントウ(Epilachna vigintioctopunctata)、ノーザンコーンルートワーム(Diabrotica longicornis)、ハナムグリ(Eucetonia pilifera)、ハリガネムシ類(Agriotes spp.)、ヒメカツオブシムシ(Attagenus unicolor japonicus)、ヒメキバネサルハムシ(Pagria signata)、ヒメコガネ(Anomala rufocuprea)、ヒメコクヌストモドキ(Palorus ratzeburgii)、ヒメゴミムシダマシ(Alphitobius laevigatus)、ヒメマルカツオブシムシ(Anthrenus verbasci)、ヒラタキクイムシ(Lyctus brunneus)、ヒラタコクヌストモドキ(Tribolium confusum)、フタスジヒメハムシ(Medythia nigrobilineata)、ブドウトラカミキリ(Xylotrechus pyrrhoderus)、ポテトフリービートル(Epitrix cucumeris)、マツノキクイムシ(Tomicus piniperda)、マツノマダラカミキリ(Monochamus alternatus)、マメコガネ(Popillia japonica)、マメハンミョウ(Epicauta gorhami)、メイズウィービル(Sitophilus zeamais)、モモチョッキリゾウムシ(Rhynchites heros)、ヤサイゾウムシ(Listroderes costirostris)、ヨツモンマメゾウムシ(Callosobruchus maculatus)、リンゴコフキゾウムシ(Phyllobius armatus)、リンゴハナゾウムシ(Anthonomus pomorum)、ルリハムシ(Linaeidea aenea)、及びワタミゾウムシ(Anthonomus grandis)等が挙げられる。
Examples of pests of the order Coleoptera include Xystrocera globosa, Paederus fuscipes, Eucetonia roelofsi, Callosobruchus chinensis, Cylas formicarius, and alfalfa weevil. (Hypera postica), rice weevil (Echinocnemus squameus), rice oulema (Oulema oryzae), rice weevil (Donacia provosti), rice water weevil (Lissorhoptrus oryzophilus), potato potato (Colasposoma dauricum), caterpillar weevil (Euscepes postfasciatus), kidney beetle (Epilachna) varivestis), kidney beans Weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), corn weevil (Involvulus cupreus), cucurbit beetle (Aulacophora femoralis), pea weevil (Bruchus pisorum), giant lady beetle (Epilachna vigintioctomaculata), snail beetle Carpophilus dimidiatus, Cassida nebulosa, Luperomorpha tunebrosa, Phyllotreta striolata, Psacothea hilaris, Aeolesthes chrysothrix, Curculio sikkimensis, Carpophilus hemipterus), Oxycetonia jucunda, Diabrotica spp., Mimela splendens, Sitophilus zeamais, Tribolium castaneum, Sitophilus oryzae, Sitophilus oryzae (Palorus subdepressus), Melolontha japonica, Anoplophora malasiaca, Neatus picipes, Colorado potato beetle (Leptinotarsa decemlineata), Southern corn rootworm (Diabrotica undecimpunctata howardi), Sphenophorus venatus, Crioceris quatuordecimpunctata, Conotrachelus nenuphar, Ceuthorhynchidius albosuturalis, Phaedon brassicae, Lasioderma serricorne, Sitona japonicus, Adoretus tenuimaculatus) , Tenebrio molitor, Basilepta balyi, Hypera nigrirostris, Chaetocnema concinna, Anomala cuprea, Heptophylla picea, Lady beetle (Epilachna vigintioctopunctata), Northern corn rootworm (Diabrotica longicornis), Honey beetle (Eucetonia pilifera), Agriotes spp., Attagenus unicolor japonicus, Pagria signata, Anomala rufocuprea), Palorus ratzeburgii, Alphitobius laevigatus, Anthrenus verbasci, Lyctus brunneus, Tribolium confusum, Medythia nigrobilineata ), grapes Xylotrechus pyrrhoderus, potato free beetle (Epitrix cucumeris), pine beetle (Tomicus piniperda), monochamus alternatus, populia japonica, epicauta gorhami, maize weevil (Sitophilus zeamais) , Rhynchites heros, Listroderes costirostris, Callosobruchus maculatus, Phyllobius armatus, Anthonomus pomorum, Linaeidea aenea, and Anthonomus pomorum. grandis), etc.
双翅目(ハエ目)害虫として例えば、アカイエカ(Culex pipiens pallens)、アカザモグリハナバエ(Pegomya hyoscyami)、アシグロハモグリバエ(Liriomyza huidobrensis)、イエバエ(Musca domestica)、イネキモグリバエ(Chlorops oryzae)、イネクキミギワバエ(Hydrellia sasakii)、イネハモグリバエ(Agromyza oryzae)、イネヒメハモグリバエ又はイネミギワバエ(Hydrellia griseola)、インゲンモグリバエ(Ophiomyia phaseoli)、ウリミバエ(Dacus cucurbitae)、オウトウショウジョウバエ(Drosophila suzukii)、オウトウハマダラミバエ(Rhacochlaena japonica)、オオイエバエ(Muscina stabulans)、オオキモンノミバエ(Megaselia spiracularis)等のノミバエ類、オオチョウバエ(Clogmia albipunctata)、キリウジガガンボ(Tipula aino)、クロキンバエ(Phormia regina)、コガタアカイエカ(Culex tritaeniorhynchus)、シナハマダラカ(Anopheles sinensis)、ダイコンバエ(Hylemya brassicae)、ダイズサヤタマバエ(Asphondylia sp.)、タネバエ(Delia platura)、タマネギバエ(Delia antiqua)、ヨーロッパオウトウミバエ(Rhagoletis cerasi)、チカイエカ(Culex pipiens molestus Forskal)、チチュウカイミバエ(Ceratitis capitata)、チビクロバネキノコバエ(Bradysia agrestis)、テンサイモグリハナバエ(Pegomya cunicularia)、トマトハモグリバエ(Liriomyza sativae)、ナスハモグリバエ(Liriomyza bryoniae)、ナモグリバエ(Chromatomyia horticola)、ネギハモグリバエ(Liriomyza chinensis)、ネッタイイエカ(Culex quinquefasciatus)、ネッタイシマカ(Aedes aegypti)、ヒトスジシマカ(Aedes albopictus)、マメハモグリバエ(Liriomyza trifolii)、トマトハモグリバエ(Liriomyza sativae)、ミカンコミバエ(Dacus dorsalis)、ミカンバエ(Dacus tsuneonis)、ムギアカタマバエ(Sitodiplosis mosellana)、ムギキモグリバエ(Meromuza nigriventris)、メキシコミバエ(Anastrepha ludens)、及びリンゴミバエ(Rhagoletis pomonella)等が挙げられる。
Diptera pests include Culex pipiens pallens, Pegomya hyoscyami, Liriomyza huidobrensis, Musca domestica, Chlorops oryzae, and Chlorops oryzae. Hydrellia sasakii, Agromyza oryzae, Hydrellia griseola, Ophiomyia phaseoli, Dacus cucurbitae, Drosophila suzukii, Drosophila suzukii (Rhacochlaena japonica ), Muscina stabulans, Megaselia spiracularis and other flea flies, Clogmia albipunctata, Tipula aino, Phormia regina, Culex tritaeniorhynchus, Anopheles sinensis), Hylemya brassicae, Asphondylia sp., Delia platura, Delia antiqua, Rhagoletis cerasi, Culex pipiens molestus Forskal, Ceratitis capitata ), Bradysia agrestis, Pegomya cunicularia, Liriomyza sativae, Liriomyza bryoniae, Chromatomyia horticola, Liriomyza chinensis, Culex quinquefasciat us ), Aedes aegypti, Aedes albopictus, Liriomyza trifolii, Liriomyza sativae, Dacus dorsalis, Dacus tsuneonis, Sitodiplosis mosellana, ( Examples include Meromuza nigriventris), Mexican fruit fly (Anastrepha ludens), and apple fruit fly (Rhagoletis pomonella).
膜翅目(ハチ目)害虫として例えば、アミメアリ(Pristomyrmex pungens)、アリガタバチ類、イエヒメアリ(Monomorium pharaohnis)、オオズアリ(Pheidole noda)、カブラハバチ(Athalia rosae)、クリタマバチ(Dryocosmus kuriphilus)、クロヤマアリ(Formica fusca japonica)、スズメバチ類、セグロカブラハバチ(Athalia infumata infumata)、チュウレンジハバチ(Arge pagana)、ニホンカブラハバチ(Athalia japonica)、ハキリアリ(Acromyrmex spp.)、ファイヤーアント(Solenopsis spp.)、リンゴハバチ(Arge mali)、及びルリアリ(Ochetellus glaber)等が挙げられる。
Hymenoptera (Hymenoptera) pests include, for example, Pristomyrmex pungens, wasps, Monomorium pharaohnis, Pheidole noda, Athalia rosae, Dryocosmus kuriphilus, and Formica fusca japonica. , Wasps, Athalia infumata infumata, Arge pagana, Athalia japonica, Acromyrmex spp., fire ant (Solenopsis spp.), Arge mali (Ochetellus glaber) etc.
直翅目(バッタ目)害虫として例えば、クサキリ(Homorocoryphus lineosus)、ケラ(Gryllotalpa sp.)、コイナゴ(Oxya hyla intricata)、コバネイナゴ(Oxya yezoensis)、トノサマバッタ(Locusta migratoria)、ハネナガイナゴ(Oxya japonica)、ヒメクサキリ(Homorocoryphus jezoensis)、及びエンマコオロギ(Teleogryllus emma)等が挙げられる。
Orthoptera pests include Homorocoryphus lineosus, Gryllotalpa sp., Oxya hyla intricata, Oxya yezoensis, Locusta migratoria, Oxya japonica, and Oxya japonica. (Homorocoryphus jezoensis), and Enma cricket (Teleogryllus emma).
アザミウマ目害虫として例えば、アカオビアザミウマ(Selenothrips rubrocinctus)、イネアザミウマ(Stenchaetothrips biformis)、イネクダアザミウマ(Haplothrips aculeatus)、カキクダアザミウマ(Ponticulothrips diospyrosi)、キイロハナアザミウマ(Thrips flavus)、クサキイロアザミウマ(Anaphothrips obscurus)、クスクダアザミウマ(Liothrips floridensis) 、グラジオラスアザミウマ(Thrips simplex)、クロゲハナアザミウマ(Thrips nigropilosus)、クロトンアザミウマ(Heliothrips haemorrhoidalis)、クワアザミウマ(Pseudodendrothrips mori)、コスモスアザミウマ(Microcephalothrips abdominalis)、シイオナガクダアザミウマ(Leeuwenia pasanii)、シイマルクダアザミウマ(Litotetothrips pasaniae)、シトラススリップス(Scirtothrips citri)、シナクダアザミウマ(Haplothrips chinensis)、ダイズアザミウマ(Mycterothrips glycines)、ダイズウスイロアザミウマ(Thrips setosus)、チャノキイロアザミウマ(Scirtothrips dorsalis)、チャノクロアザミウマ(Dendrothrips minowai)、ツメクサクダアザミウマ(Haplothrips niger)、ネギアザミウマ(Thrips tabaci)、ネギクロアザミウマ(Thrips alliorum)、ハナアザミウマ(Thrips hawaiiensis)、ハナクダアザミウマ(Haplothrips kurdjumovi)、ヒゲブトアザミウマ(Chirothrips manicatus)、ヒラズハナアザミウマ(Frankliniella intonsa)、ビワハナアザミウマ(Thrips coloratus)、ミカンキイロアザミウマ(Franklinella occidentalis)、ミナミキイロアザミウマ(Thrips palmi)、ユリキイロアザミウマ(Frankliniella lilivora)、及びユリノクダアザミウマ(Liothrips vaneeckei)等が挙げられる。
Examples of thrips pests include Selenothrips rubrocinctus, Stenchaetothrips biformis, Haplothrips aculeatus, Ponticulothrips diospyrosi, Thrips flavus, and Thrips flavus. Thrips (Anaphothrips obscurus) , Cusukuda thrips (Liothrips floridensis), Gladiolus thrips (Thrips simplex), Black thrips (Thrips nigropilosus), Croton thrips (Heliothrips haemorrhoidalis), Swamp thrips (Pseudodendrothrips mori), Cosmos thrips (Microcephalothrips Abdominalis) , Thrips ( Leeuwenia pasanii), Litotetothrips pasaniae, Scirtothrips citri, Haplothrips chinensis, Mycterothrips glycines, Thrips setosus, Tea thrips (Mycterothrips glycines) Scirtothrips dorsalis ), Choco Clothy Samewomes (DendrothRips Minowai), HaplothRips Niger (HAPLOTHRIPS NIGER), Negi Tabaci, Negikuro -Tabaci (Thrips Alliolum), Hana Azamium (Thrips Ha) Waiiensis), Hanakuda thigh (HAPLOTHRIPS KURDJUMOVI), Higebuto Thrips (Chirothrips manicatus), Thrips (Frankliniella intonsa), Thrips coloratus (Thrips coloratus), Orange thrips (Franklinella occidentalis), Southern yellow thrips (Thrips palmi), Black thrips (Frankliniella lilivora), and Liothrips vaneeckei) etc.
ダニ目害虫として例えば、アオツツガムシ(Leptotrombidium akamushi)、アシノワハダニ(Tetranychus ludeni)、アメリカンドックチック(Dermacentor variabilis)、イシイナミハダニ(Tetranychus truncatus)、イエダニ(Ornithonyssus bacoti)、イヌニキビダニ(Demodex canis)、オウトウハダニ(Tetranychus viennensis)、カンザワハダニ(Tetranychus kanzawai)、クリイロコイタマダニ(Rhipicephalus sanguineus)等のマダニ類、クワガタツメダニ(Cheyletus malaccensis)、ケナガコナダニ(Tyrophagus putrescentiae)、コナヒョウヒダニ(Dermatophagoides farinae)、セアカゴケグモ(Latrodectus hasseltii)、タイワンカクマダニ(Dermacentor taiwanicus)、チャノナガサビダニ(Acaphylla theavagrans)、チャノホコリダニ(Polyphagotarsonemus latus)、トマトサビダニ(Aculops lycopersici)、トリサシダニ(Ornithonyssus sylvairum)、ナミハダニ(Tetranychus urticae)、ニセナシサビダニ(Eriophyes chibaensis)、ヒゼンダニ(Sarcoptes scabiei)、フタトゲチマダニ(Haemaphysalis longicornis)、ブラックレッグドチック(Ixodes scapularis)、ホウレンソウケナガコナダニ(Tyrophagus similis)、ホソツメダニ(Cheyletus eruditus)、ミカンハダニ(Panonychus citri)、ミナミツメダニ(Cheyletus moorei)、ミナミヒメハダニ(Brevipalpus phoenicis)、ミミヒゼンダニ(Octodectes cynotis)、ヤケヒョウヒダニ(Dermatophagoides ptrenyssnus)、ヤマトチマダニ(Haemaphysalis flava)、ヤマトマダニ(Ixodes ovatus)、リュウキュウミカンサビダニ(Phyllocoptruta citri)、リンゴサビダニ(Aculus schlechtendali)、リンゴハダニ(Panonychus ulmi)、ローンスターチック(Amblyomma americanum)、及びワクモ(Dermanyssus gallinae)、ロビンネダニ(Rhyzoglyphus robini)、ネダニモドキの一種(Sancassania sp.)等が挙げられる。
Examples of insect pests in the order of Acari include Leptotrombidium akamushi, Tetranychus ludeni, Dermacentor variabilis, Tetranychus truncatus, Ornithonyssus bacoti, Demodex canis, and Demodex canis. Ticks such as Tetranychus viennensis, Tetranychus kanzawai, and Rhipicephalus sanguineus, Cheyletus malaccensis, Tyrophagus putrescentiae, Dermatophagoides farinae, and Latrodectus ha. selstii), Formosan cactus Dermacentor taiwanicus, Acaphylla theavagrans, Polyphagotarsonemus latus, Aculops lycopersici, Ornithonyssus sylvairum, Tetranychus urticae, Eriophyes chibaensis, Zendani (Sarcoptes) scabiei), Haemaphysalis longicornis, black-legged tick (Ixodes scapularis), Tyrophagus similis, Cheyletus eruditus, Panonychus citri, Cheyletus moorei, Brevipalpus phoenici s ), Octodectes cynotis, Dermatophagoides ptrenyssnus, Haemaphysalis flava, Ixodes ovatus, Phyllocoptruta citri, Aculus schlechtendali, Panonychus ulmi , loan Examples include star chick (Amblyomma americanum), red mite (Dermanyssus gallinae), robin mite (Rhyzoglyphus robini), and a type of mite (Sancassania sp.).
シロアリ目害虫として例えば、アマミシロアリ(Reticulitermes miyatakei)、アメリカカンザイシロアリ(Incisitermes minor)、イエシロアリ(Coptotermes formosanus)、オオシロアリ(Hodotermopsis japonica)、カンモンシロアリ(Reticulitermes sp.)、キアシシロアリ(Reticulitermes flaviceps amamianus)、クシモトシロアリ(Glyptotermes kushimensis)、コウシュウイエシロアリ(Coptotermes guangzhoensis)、コウシュンシロアリ(Neotermes koshunensis)、コダマシロアリ(Glyptotermes kodamai)、サツマシロアリ(Glyptotermes satsumensis)、ダイコクシロアリ(Cryptotermes domesticus)、タイワンシロアリ(Odontotermes formosanus)、ナカジマシロアリ(Glyptotermes nakajimai)、ニトベシロアリ(Pericapritermes nitobei)、及びヤマトシロアリ(Reticulitermes speratus)等が挙げられる。
Examples of termite pests include Reticulitermes miyatakei, Incisitermes minor, Coptotermes formosanus, Hodotermopsis japonica, Reticulitermes sp., and Reticulitermes flaviceps amamianus. , Glyptotermes kushimensis, Coptotermes guangzhoensis, Neotermes koshunensis, Glyptotermes kodamai, Glyptotermes satsumensis, Cryptotermes domesticus, Odon totermes formosanus) , Glyptotermes nakajimai, Pericapritermes nitobei, and Reticulitermes speratus.
ゴキブリ目害虫として例えば、クロゴキブリ(Periplaneta fuliginosa)、チャバネゴキブリ(Blattella germanica)、トウヨウゴキブリ(Blatta orientalis)、トビイロゴキブリ(Periplaneta brunnea)、ヒメチャバネゴキブリ(Blattella lituricollis)、ヤマトゴキブリ(Periplaneta japonica)、及びワモンゴキブリ(Periplaneta americana)等が挙げられる。
Examples of pests of the order Cockroaches include the black cockroach (Periplaneta fuliginosa), the German cockroach (Blattella germanica), the Japanese cockroach (Blatta orientalis), the brown cockroach (Periplaneta brunnea), the Japanese cockroach (Blattella lituricollis), the Japanese cockroach (Periplaneta japonica), and the American cockroach. (Periplaneta americana) etc.
線虫類として例えば、イチゴメセンチュウ(Nothotylenchus acris)、イネシンガレセンチュウ(Aphelenchoides besseyi)、キタネグサレセンチュウ(Pratylenchus penetrans)、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)、ジャガイモシストセンチュウ(Globodera rostochiensis)、ジャワネコブセンチュウ(Meloidogyne javanica)、ダイズシストセンチュウ(Heterodera glycines)、ミナミネグサレセンチュウ(Pratylenchus coffeae)、ムギネグサレセンチュウ(Pratylenchus neglectus)、及びミカンネセンチュウ(Tylenchus semipenetrans)等が挙げられる。
Examples of nematodes include the strawberry nematode (Nothotylenchus acris), the rice nematode (Aphelenchoides besseyi), the northern nematode (Pratylenchus penetrans), the northern nematode (Meloidogyne hapla), the sweet potato nematode (Meloidogyne incognita), and the potato cyst nematode (Globodera). rostochiensis), Javan cat nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), southern coffeae (Pratylenchus coffeae), barley coffeae (Pratylenchus neglectus), and citrus nematode (Tylenchus semipenetrans).
軟体動物類として例えば、スクミリンゴガイ(Pomacea canaliculata)、アフリカマイマイ(Achatina fulica)、ナメクジ(Meghimatium bilineatum)、チャコウラナメクジ(Lehmannina valentiana)、コウラナメクジ(Limax flavus)、及びウスカワマイマイ(Acusta despecta sieboldiana)等が挙げられる。
Examples of molluscs include Pomacea canaliculata, Achatina fulica, Meghimatium bilineatum, Lehmannina valentiana, Limax flavus, and Acusta despecta sieboldiana. can be mentioned.
また、本発明の農園芸用害虫防除剤は、その他の害虫としてトマトキバガ(Tuta absoluta)に対しても強い殺虫効果を有するものである。
Furthermore, the agricultural and horticultural pest control agent of the present invention has a strong insecticidal effect against other pests such as tomato absoluta (Tuta absoluta).
本発明の一般式(1)で表される化合物又はその塩類を有効成分とする農園芸用害虫防除剤は、水田作物、畑作物、果樹、野菜、その他の作物及び花卉等に被害を与える前記害虫に対して顕著な防除効果を有するので、害虫の発生が予測される時期に合わせて、害虫の発生前又は発生が確認された時点で育苗施設、水田、畑、果樹、野菜、その他の作物、花卉等の種子、水田水、茎葉又は土壌等の栽培担体等に処理することにより本発明の農園芸用害虫防除剤の所期の効果が奏せられるものである。中でも、作物、花卉等の育苗土壌、移植時の植え穴土壌、株元、灌漑水、水耕栽培における栽培水等に処理して、土壌を介し又は介さずして根から本発明化合物を吸収させることによるいわゆる浸透移行性を利用した施用が好ましい使用形態である。
The agricultural and horticultural pest control agent containing the compound represented by the general formula (1) or its salts as an active ingredient of the present invention is suitable for use in agricultural and horticultural pest control agents that cause damage to paddy crops, field crops, fruit trees, vegetables, other crops, flowers, etc. Because it has a remarkable control effect against pests, it is necessary to remove seedlings, paddy fields, fields, fruit trees, vegetables, and other crops before the outbreak of pests or when the outbreak of pests is confirmed. The intended effects of the agricultural and horticultural pest control agent of the present invention can be achieved by treating it on cultivation carriers such as seeds of flowers, paddy water, stems and leaves, or soil. Among them, the compound of the present invention can be absorbed through the roots through or without the soil by treating the soil for raising seedlings of crops, flowers, etc., the soil for planting holes during transplanting, the roots of plants, irrigation water, cultivation water for hydroponic cultivation, etc. A preferred form of use is application that takes advantage of the so-called permeation and migration properties.
本発明の農園芸用害虫防除剤を使用することができる有用植物は特に限定されるものではないが、例えば穀類(例えば、稲、大麦、小麦、ライ麦、オート麦、とうもろこし等)、豆類(大豆、小豆、そら豆、えんどう豆、いんげん豆、落花生等)、果樹・果実類(林檎、柑橘類、梨、葡萄、桃、梅、桜桃、胡桃、栗、アーモンド、バナナ等)、葉・果菜類(キャベツ、トマト、ほうれんそう、ブロッコリー、レタス、たまねぎ、ねぎ(あさつき、わけぎ)、ピーマン、なす、いちご、ペッパー、おくら、にら等)、根菜類(にんじん、馬鈴薯、さつまいも、さといも、だいこん、かぶ、れんこん、ごぼう、にんにく、らっきょう等)、加工用作物(棉、麻、ビート、ホップ、さとうきび、てんさい、オリーブ、ゴム、コーヒー、タバコ、茶等)、ウリ類(かぼちゃ、きゅうり、すいか、まくわうり、メロン等)、牧草類(オーチャードグラス、ソルガム、チモシー、クローバー、アルファルファ等)、芝類(高麗芝、ベントグラス等)、香料等鑑賞用作物(ラベンダー、ローズマリー、タイム、パセリ、胡椒、生姜等)、花卉類(きく、ばら、カーネーション、蘭、チューリップ、ゆり等)、庭木(いちょう、さくら類、あおき等)、林木(トドマツ類、エゾマツ類、松類、ヒバ、杉、桧、ユウカリ等)等の植物を挙げることができる。
Useful plants to which the agricultural and horticultural pest control agent of the present invention can be used are not particularly limited, but include, for example, cereals (e.g., rice, barley, wheat, rye, oats, corn, etc.), legumes (soybean, etc.) , adzuki beans, fava beans, peas, kidney beans, peanuts, etc.), fruit trees/fruits (apples, citrus fruits, pears, grapes, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves/fruit vegetables (cabbage) , tomatoes, spinach, broccoli, lettuce, onions, green onions (morning onions, spring onions), green peppers, eggplants, strawberries, peppers, okra, chives, etc.), root vegetables (carrots, potatoes, sweet potatoes, taro, radish, turnips, lotus root, etc.) burdock, garlic, rakkyo, etc.), processed crops (cotton, hemp, beets, hops, sugar cane, sugar beets, olives, rubber, coffee, tobacco, tea, etc.), cucurbits (pumpkin, cucumber, watermelon, melon, melon) etc.), grasses (orchard grass, sorghum, timothy, clover, alfalfa, etc.), grasses (Korea grass, bentgrass, etc.), ornamental crops such as spices (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), Flowers (flowers, roses, carnations, orchids, tulips, lilies, etc.), garden trees (gingko, cherry blossoms, blueberry, etc.), forest trees (sperm firs, spruces, pines, hiba, cedar, cypress, eucalyptus, etc.), etc. I can list plants.
上記「植物」には、イソキサフルトール等のHPPD阻害剤、イマゼタピル、チフェンスルフロンメチル等のALS阻害剤、グリホサート等のEPSP合成酵素阻害剤、グルホシネート等のグルタミン合成酵素阻害剤、セトキシジム等のアセチルCoAカルボキシラーゼ阻害剤、ブロモキシニル、ジカンバ、2,4‐D等の除草剤に対する耐性を古典的な育種法、もしくは遺伝子組換え技術により耐性を付与された植物も含まれる。
The above "plants" include HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthetase inhibitors such as glufosinate, and setoxydim. Also included are plants that have been made resistant to herbicides such as acetyl-CoA carboxylase inhibitors, bromoxynil, dicamba, and 2,4-D by classical breeding methods or genetic recombination techniques.
古典的な育種法により耐性を付与された「植物」の例としては、イマゼタピル等のイミダゾリノン系ALS阻害型除草剤に耐性のナタネ、コムギ、ヒマワリ、イネがありClearfield(登録商標)の商品名で既に販売されている。同様に古典的な育種法によるチフェンスルフロンメチル等のスルホニルウレア系ALS阻害型除草剤に耐性のダイズがあり、STSダイズの商品名で既に販売されている。同様に古典的な育種法によりトリオンオキシム系、アリールオキシフェノキシプロピオン酸系除草剤などのアセチルCoAカルボキシラーゼ阻害剤に耐性が付与された植物の例としてSRコーン等がある。
またアセチルCoAカルボキシラーゼ阻害剤に耐性が付与された植物はプロシーディングズ・オブ・ザ・ナショナル・アカデミー・オブ・サイエンシーズ・オブ・ザ・ユナイテッド・ステーツ・オブ・アメリカ(Proc.Natl.Acad.Sci.USA)87巻、7175~7179頁(1990年)等に記載されている。またアセチルCoAカルボキシラーゼ阻害剤に耐性の変異アセチルCoAカルボキシラーゼがウィード・サイエンス(Weed Science)53巻、728~746頁(2005年)等に報告されており、こうした変異アセチルCoAカルボキシラーゼ遺伝子を遺伝子組換え技術により植物に導入するかもしくは抵抗性付与に関わる変異を植物アセチルCoAカルボキシラーゼに導入する事により、アセチルCoAカルボキシラーゼ阻害剤に耐性の植物を作出することができ、さらに、キメラプラスティ技術(Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.)に代表される塩基置換変異導入核酸を植物細胞内に導入して植物のアセチルCoAカルボキシラーゼ遺伝子やALS遺伝子等に部位特異的アミノ酸置換変異を導入することにより、アセチルCoAカルボキシラーゼ阻害剤やALS阻害剤等に耐性の植物を作出することができ、これらの植物に対しても本発明の農園芸用害虫防除剤を使用することができる。 Examples of "plants" that have been made resistant through classical breeding methods include rapeseed, wheat, sunflower, and rice, which are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazethapyr, which is available under the trade name Clearfield (registered trademark). is already on sale. Similarly, there is a soybean resistant to sulfonylurea-based ALS-inhibiting herbicides such as thifensulfuron-methyl produced by classical breeding methods, and it is already sold under the trade name STS soybean. Similarly, SR corn is an example of a plant that has been made resistant to acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides through classical breeding methods.
In addition, plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors are listed in the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA) Vol. 87, pp. 7175-7179 (1990). In addition, mutant acetyl-CoA carboxylase that is resistant to acetyl-CoA carboxylase inhibitors has been reported in Weed Science, Vol. Plants resistant to acetyl-CoA carboxylase inhibitors can be created by introducing them into plants or by introducing mutations that confer resistance into plant acetyl-CoA carboxylase inhibitors.Furthermore, chimeraplasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.) is introduced into plant cells to introduce site-specific amino acids into plant acetyl-CoA carboxylase genes, ALS genes, etc. By introducing substitution mutations, it is possible to create plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, etc., and the agricultural and horticultural pest control agent of the present invention can also be used for these plants. can.
またアセチルCoAカルボキシラーゼ阻害剤に耐性が付与された植物はプロシーディングズ・オブ・ザ・ナショナル・アカデミー・オブ・サイエンシーズ・オブ・ザ・ユナイテッド・ステーツ・オブ・アメリカ(Proc.Natl.Acad.Sci.USA)87巻、7175~7179頁(1990年)等に記載されている。またアセチルCoAカルボキシラーゼ阻害剤に耐性の変異アセチルCoAカルボキシラーゼがウィード・サイエンス(Weed Science)53巻、728~746頁(2005年)等に報告されており、こうした変異アセチルCoAカルボキシラーゼ遺伝子を遺伝子組換え技術により植物に導入するかもしくは抵抗性付与に関わる変異を植物アセチルCoAカルボキシラーゼに導入する事により、アセチルCoAカルボキシラーゼ阻害剤に耐性の植物を作出することができ、さらに、キメラプラスティ技術(Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.)に代表される塩基置換変異導入核酸を植物細胞内に導入して植物のアセチルCoAカルボキシラーゼ遺伝子やALS遺伝子等に部位特異的アミノ酸置換変異を導入することにより、アセチルCoAカルボキシラーゼ阻害剤やALS阻害剤等に耐性の植物を作出することができ、これらの植物に対しても本発明の農園芸用害虫防除剤を使用することができる。 Examples of "plants" that have been made resistant through classical breeding methods include rapeseed, wheat, sunflower, and rice, which are resistant to imidazolinone-based ALS-inhibiting herbicides such as imazethapyr, which is available under the trade name Clearfield (registered trademark). is already on sale. Similarly, there is a soybean resistant to sulfonylurea-based ALS-inhibiting herbicides such as thifensulfuron-methyl produced by classical breeding methods, and it is already sold under the trade name STS soybean. Similarly, SR corn is an example of a plant that has been made resistant to acetyl-CoA carboxylase inhibitors such as trione oxime herbicides and aryloxyphenoxypropionic acid herbicides through classical breeding methods.
In addition, plants that have been conferred resistance to acetyl-CoA carboxylase inhibitors are listed in the Proceedings of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci. USA) Vol. 87, pp. 7175-7179 (1990). In addition, mutant acetyl-CoA carboxylase that is resistant to acetyl-CoA carboxylase inhibitors has been reported in Weed Science, Vol. Plants resistant to acetyl-CoA carboxylase inhibitors can be created by introducing them into plants or by introducing mutations that confer resistance into plant acetyl-CoA carboxylase inhibitors.Furthermore, chimeraplasty technology (Gura T. 1999. Repairing the Genome's Spelling Mistakes. Science 285: 316-318.) is introduced into plant cells to introduce site-specific amino acids into plant acetyl-CoA carboxylase genes, ALS genes, etc. By introducing substitution mutations, it is possible to create plants resistant to acetyl-CoA carboxylase inhibitors, ALS inhibitors, etc., and the agricultural and horticultural pest control agent of the present invention can also be used for these plants. can.
更に遺伝子組換え植物で発現される毒素として、バチルス・セレウスやバチルス・ポピリエ由来の殺虫性タンパク;バチルス・チューリンゲンシス由来のCry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1又はCry9C等のδ‐エンドトキシン、VIP1、VIP2、VIP3又はVIP3A等の殺虫タンパク;線虫由来の殺虫タンパク;さそり毒素、クモ毒素、ハチ毒素又は昆虫特異的神経毒素等動物によって産生される毒素;糸状菌類毒素;植物レクチン;アグルチニン;トリプシン阻害剤、セリンプロテアーゼ阻害剤、パタチン、シスタチン、パパイン阻害剤等のプロテアーゼ阻害剤;リシン、トウモロコシ-RIP、アブリン、ルフィン、サポリン、ブリオジン等のリボゾーム不活性化タンパク(RIP);3‐ヒドロキシステロイドオキシダーゼ、エクジステロイド‐UDP‐グルコシルトランスフェラーゼ、コレステロールオキシダーゼ等のステロイド代謝酵素;エクダイソン阻害剤;HMG‐CoAリダクターゼ;ナトリウムチャネル、カルシウムチャネル阻害剤等のイオンチャネル阻害剤;幼若ホルモンエステラーゼ;利尿ホルモン受容体;スチルベンシンターゼ;ビベンジルシンターゼ;キチナーゼ;グルカナーゼ等が挙げられる。
Furthermore, as toxins expressed in genetically modified plants, insecticidal proteins derived from Bacillus cereus and Bacillus popilliae; δ- such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis; Insecticidal proteins such as endotoxin, VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins derived from nematodes; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, and papain inhibitors; ribosome inactivating proteins (RIPs) such as ricin, corn-RIP, abrin, ruffin, saporin, and bryodin; 3- Steroid metabolic enzymes such as hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, and cholesterol oxidase; ecdysone inhibitors; HMG-CoA reductase; ion channel inhibitors such as sodium channel and calcium channel inhibitors; juvenile hormone esterase; diuresis Examples include hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase.
またこの様な遺伝子組換え植物で発現される毒素として、Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1、Cry9C、Cry34Ab又はCry35Ab等のδ‐エンドトキシンタンパク、VIP1、VIP2、VIP3又はVIP3A等の殺虫タンパクのハイブリッド毒素、一部を欠損した毒素、修飾された毒素も含まれる。ハイブリッド毒素は組換え技術を用いて、これらタンパクの異なるドメインの新しい組み合わせによって作り出される。一部を欠損した毒素としては、アミノ酸配列の一部を欠損したCry1Abが知られている。修飾された毒素としては、天然型の毒素のアミノ酸の1つ又は複数が置換されている。
これら毒素の例及びこれら毒素を合成する事ができる組換え植物は、EP‐A‐0 374 753、WO 93/07278、WO 95/34656、EP‐A‐0 427 529、EP‐A‐451 878、WO 03/052073等に記載されている。 In addition, toxins expressed in such genetically modified plants include δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, VIP1, VIP2, VIP3, or VIP3A, etc. Hybrid toxins, partially deleted toxins, and modified toxins of insecticidal proteins are also included. Hybrid toxins are created by new combinations of different domains of these proteins using recombinant technology. Cry1Ab, which has a partially deleted amino acid sequence, is known as a partially deleted toxin. A modified toxin has one or more amino acids substituted for the naturally occurring toxin.
Examples of these toxins and recombinant plants capable of synthesizing these toxins are found in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 , WO 03/052073, etc.
これら毒素の例及びこれら毒素を合成する事ができる組換え植物は、EP‐A‐0 374 753、WO 93/07278、WO 95/34656、EP‐A‐0 427 529、EP‐A‐451 878、WO 03/052073等に記載されている。 In addition, toxins expressed in such genetically modified plants include δ-endotoxin proteins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab, or Cry35Ab, VIP1, VIP2, VIP3, or VIP3A, etc. Hybrid toxins, partially deleted toxins, and modified toxins of insecticidal proteins are also included. Hybrid toxins are created by new combinations of different domains of these proteins using recombinant technology. Cry1Ab, which has a partially deleted amino acid sequence, is known as a partially deleted toxin. A modified toxin has one or more amino acids substituted for the naturally occurring toxin.
Examples of these toxins and recombinant plants capable of synthesizing these toxins are found in EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878 , WO 03/052073, etc.
これらの組換え植物に含まれる毒素は、特に、甲虫目害虫、半翅目害虫、双翅目害虫、鱗翅目害虫、線虫類への耐性を植物に付与する。本発明の農園芸用害虫防除剤はそれらの技術と併用、あるいは体系化して用いることもできる。
The toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera, Diptera, Lepidoptera, and nematodes. The agricultural and horticultural pest control agent of the present invention can be used in combination with or systematized with those techniques.
本発明の農園芸用害虫防除剤は各種害虫を防除するためにそのまま、又は水等で適宜希釈し、若しくは懸濁させた形で害虫あるいは線虫防除に有効な量を当該害虫及び線虫の発生が予測される植物に使用すればよく、例えば果樹、穀類、野菜等において発生する害虫及び線虫に対しては茎葉部に散布する他に、種子の薬剤への浸漬、種子粉衣、カルパー処理等の種子処理、土壌全層混和、作条施用、床土混和、セル苗処理、植え穴処理、株元処理、トップドレス、イネの箱処理、水面施用等、土壌等に処理して根から吸収させて使用することもできる。加えて、養液(水耕)栽培における養液への施用、くん煙あるいは樹幹注入等による使用もできる。
更に、本発明の農園芸用害虫防除剤は、そのまま、又は水等で適宜希釈し、若しくは懸濁させた形で害虫防除に有効な量を当該害虫の発生が予測される場所に使用すればよく、例えば貯穀害虫、家屋害虫、衛生害虫、森林害虫等に散布する他に、家屋建材への塗布、くん煙、ベイト等として使用することもできる。 The agricultural and horticultural pest control agent of the present invention is used as it is, or diluted or suspended with water etc. in an effective amount to control various pests and nematodes. It can be used on plants where outbreaks are predicted. For example, for pests and nematodes that occur in fruit trees, grains, vegetables, etc., in addition to spraying on the stems and leaves, soaking seeds in chemicals, seed dressing, and cultivating methods can be used. Treatments such as seed treatment, soil full layer mixing, cropping application, bed soil mixing, cell seedling treatment, planting hole treatment, plant base treatment, top dressing, rice box treatment, water surface application, etc. It can also be absorbed and used. In addition, it can also be applied to a nutrient solution in hydroponic cultivation, smoked, or injected into a tree trunk.
Furthermore, the agricultural and horticultural pest control agent of the present invention can be used as it is, diluted with water, etc., or suspended in an effective amount for pest control in a place where the pests are expected to occur. For example, in addition to spraying on grain storage pests, house pests, sanitary pests, forest pests, etc., it can also be used as a coating on house building materials, smoke, bait, etc.
更に、本発明の農園芸用害虫防除剤は、そのまま、又は水等で適宜希釈し、若しくは懸濁させた形で害虫防除に有効な量を当該害虫の発生が予測される場所に使用すればよく、例えば貯穀害虫、家屋害虫、衛生害虫、森林害虫等に散布する他に、家屋建材への塗布、くん煙、ベイト等として使用することもできる。 The agricultural and horticultural pest control agent of the present invention is used as it is, or diluted or suspended with water etc. in an effective amount to control various pests and nematodes. It can be used on plants where outbreaks are predicted. For example, for pests and nematodes that occur in fruit trees, grains, vegetables, etc., in addition to spraying on the stems and leaves, soaking seeds in chemicals, seed dressing, and cultivating methods can be used. Treatments such as seed treatment, soil full layer mixing, cropping application, bed soil mixing, cell seedling treatment, planting hole treatment, plant base treatment, top dressing, rice box treatment, water surface application, etc. It can also be absorbed and used. In addition, it can also be applied to a nutrient solution in hydroponic cultivation, smoked, or injected into a tree trunk.
Furthermore, the agricultural and horticultural pest control agent of the present invention can be used as it is, diluted with water, etc., or suspended in an effective amount for pest control in a place where the pests are expected to occur. For example, in addition to spraying on grain storage pests, house pests, sanitary pests, forest pests, etc., it can also be used as a coating on house building materials, smoke, bait, etc.
種子処理の方法としては、例えば、液状又は固体状の製剤を希釈又は希釈せずして液体状態にて種子を浸漬して薬剤を浸透させる方法、固形製剤又は液状製剤を種子と混和、粉衣処理して種子の表面に付着させる方法、樹脂、ポリマー等の付着性の担体と混和して種子にコーティングする方法、植え付けと同時に種子付近に散布する方法等が挙げられる。
当該種子処理を行う「種子」とは、植物の繁殖に用いられる栽培初期の植物体を意味し、例えば、種子の他、球根、塊茎、種芋、株芽、むかご、鱗茎、あるいは挿し木栽培用の栄養繁殖用の植物体を挙げることができる。
本発明の使用方法を実施する場合の植物の「土壌」又は「栽培担体」とは、作物を栽培するための支持体、特に根を生えさせる支持体を示すものであり、材質は特に制限されないが、植物が生育しうる材質であれば良く、いわゆる土壌、育苗マット、水等であっても良く、具体的な素材としては例えば、砂、軽石、バーミキュライト、珪藻土、寒天、ゲル状物質、高分子物質、ロックウール、グラスウール、木材チップ、バーク等であっても良い。 Seed treatment methods include, for example, diluting a liquid or solid preparation or immersing the seeds in an undiluted liquid state to infiltrate the seeds, mixing a solid or liquid preparation with the seeds, or coating the seeds with powder. Examples include a method of treating and adhering to the surface of seeds, a method of mixing with an adhesive carrier such as a resin or polymer and coating the seeds, and a method of spraying near the seeds at the same time as planting.
The term "seed" used for the seed treatment refers to plants in the early stage of cultivation used for plant propagation, such as seeds, bulbs, tubers, seed potatoes, shoots, bulbs, scales, or cuttings for cultivation. Examples include plants for vegetative propagation.
The term "soil" or "cultivation carrier" for plants when carrying out the method of use of the present invention refers to a support for cultivating crops, especially a support for growing roots, and the material is not particularly limited. However, any material that plants can grow on may be used, such as soil, seedling mats, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, and high-quality materials. It may also be a molecular substance, rock wool, glass wool, wood chips, bark, etc.
当該種子処理を行う「種子」とは、植物の繁殖に用いられる栽培初期の植物体を意味し、例えば、種子の他、球根、塊茎、種芋、株芽、むかご、鱗茎、あるいは挿し木栽培用の栄養繁殖用の植物体を挙げることができる。
本発明の使用方法を実施する場合の植物の「土壌」又は「栽培担体」とは、作物を栽培するための支持体、特に根を生えさせる支持体を示すものであり、材質は特に制限されないが、植物が生育しうる材質であれば良く、いわゆる土壌、育苗マット、水等であっても良く、具体的な素材としては例えば、砂、軽石、バーミキュライト、珪藻土、寒天、ゲル状物質、高分子物質、ロックウール、グラスウール、木材チップ、バーク等であっても良い。 Seed treatment methods include, for example, diluting a liquid or solid preparation or immersing the seeds in an undiluted liquid state to infiltrate the seeds, mixing a solid or liquid preparation with the seeds, or coating the seeds with powder. Examples include a method of treating and adhering to the surface of seeds, a method of mixing with an adhesive carrier such as a resin or polymer and coating the seeds, and a method of spraying near the seeds at the same time as planting.
The term "seed" used for the seed treatment refers to plants in the early stage of cultivation used for plant propagation, such as seeds, bulbs, tubers, seed potatoes, shoots, bulbs, scales, or cuttings for cultivation. Examples include plants for vegetative propagation.
The term "soil" or "cultivation carrier" for plants when carrying out the method of use of the present invention refers to a support for cultivating crops, especially a support for growing roots, and the material is not particularly limited. However, any material that plants can grow on may be used, such as soil, seedling mats, water, etc. Specific materials include, for example, sand, pumice, vermiculite, diatomaceous earth, agar, gel-like substances, and high-quality materials. It may also be a molecular substance, rock wool, glass wool, wood chips, bark, etc.
作物茎葉部又は貯穀害虫、家屋害虫、衛生害虫若しくは森林害虫等への散布方法としては、乳剤、フロアブル剤等の液体製剤又は水和剤もしくは顆粒水和剤等の固形製剤を水で適宜希釈し、散布する方法、粉剤を散布する方法、又はくん煙等が挙げられる。
土壌への施用方法としては、例えば、液体製剤を水に希釈又は希釈せずして植物体の株元又は育苗用苗床等に施用する方法、粒剤を植物体の株元又は育苗のための苗床等に散布する方法、播種前又は移植前に粉剤、水和剤、顆粒水和剤、粒剤等を散布し土壌全体と混和する方法、播種前又は植物体を植える前に植え穴、作条等に粉剤、水和剤、顆粒水和剤、粒剤等を散布する方法等が挙げられる。 To spray on crop foliage or stored grain pests, household pests, sanitary pests, forest pests, etc., liquid preparations such as emulsions and flowables, or solid preparations such as wettable powders or granule wettable powders, are diluted with water as appropriate. , a method of spraying, a method of spraying a powder, a method of smoking, etc.
Methods for applying to soil include, for example, applying liquid preparations to the base of plants or seedling beds without diluting them with water, or applying granules to the base of plants or seedling beds for raising seedlings. Methods of spraying on seedbeds, etc., methods of spraying powders, wettable powders, granule wettable powders, granules, etc. before sowing or transplanting and mixing them with the entire soil, methods of spraying in planting holes, etc. before sowing or transplanting plants, etc. Examples include methods of dispersing powders, wettable powders, hydrated granules, granules, etc. in strips.
土壌への施用方法としては、例えば、液体製剤を水に希釈又は希釈せずして植物体の株元又は育苗用苗床等に施用する方法、粒剤を植物体の株元又は育苗のための苗床等に散布する方法、播種前又は移植前に粉剤、水和剤、顆粒水和剤、粒剤等を散布し土壌全体と混和する方法、播種前又は植物体を植える前に植え穴、作条等に粉剤、水和剤、顆粒水和剤、粒剤等を散布する方法等が挙げられる。 To spray on crop foliage or stored grain pests, household pests, sanitary pests, forest pests, etc., liquid preparations such as emulsions and flowables, or solid preparations such as wettable powders or granule wettable powders, are diluted with water as appropriate. , a method of spraying, a method of spraying a powder, a method of smoking, etc.
Methods for applying to soil include, for example, applying liquid preparations to the base of plants or seedling beds without diluting them with water, or applying granules to the base of plants or seedling beds for raising seedlings. Methods of spraying on seedbeds, etc., methods of spraying powders, wettable powders, granule wettable powders, granules, etc. before sowing or transplanting and mixing them with the entire soil, methods of spraying in planting holes, etc. before sowing or transplanting plants, etc. Examples include methods of dispersing powders, wettable powders, hydrated granules, granules, etc. in strips.
水稲の育苗箱への施用方法としては、剤型は、例えば播種時施用、緑化期施用、移植時施用などの施用時期により異なる場合もあるが、粉剤、顆粒水和剤、粒剤等の剤型で施用すればよい。培土との混和によっても施用することができ、培土と粉剤、顆粒水和剤又は粒剤等との混和、例えば、床土混和、覆土混和、培土全体への混和等することができる。単に、培土と各種製剤を交互に層状にして施用してもよい。
水田への施用方法としては、ジャンボ剤、パック剤、粒剤、顆粒水和剤等の固形製剤、フロアブル、乳剤等の液体状製剤を、通常は、湛水状態の水田に散布する。その他、田植え時には、適当な製剤をそのまま、あるいは、肥料に混和して土壌に散布、注入することもできる。また、水口や灌漑装置等の水田への水の流入元に乳剤、フロアブル等の薬液を利用することにより、水の供給に伴い省力的に施用することもできる。 As for the method of application to paddy rice seedling boxes, the dosage form may vary depending on the time of application, such as application at sowing, application during greening, application at transplanting, etc. It can be applied in a mold. It can also be applied by mixing with the soil, and it can be mixed with the soil and a powder, a granular wettable powder, a granule, etc., such as mixing with bed soil, mixing with soil covering, and mixing with the entire soil. You may simply apply the soil and various preparations in alternating layers.
As for the method of application to rice fields, solid preparations such as jumbo preparations, pack preparations, granules, and wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded rice fields. In addition, at the time of rice planting, a suitable formulation can be sprayed or injected into the soil as it is or mixed with fertilizer. In addition, by using a chemical solution such as an emulsion or a flowable at a source where water flows into a rice field, such as a water outlet or an irrigation system, it can be applied in a labor-saving manner as water is supplied.
水田への施用方法としては、ジャンボ剤、パック剤、粒剤、顆粒水和剤等の固形製剤、フロアブル、乳剤等の液体状製剤を、通常は、湛水状態の水田に散布する。その他、田植え時には、適当な製剤をそのまま、あるいは、肥料に混和して土壌に散布、注入することもできる。また、水口や灌漑装置等の水田への水の流入元に乳剤、フロアブル等の薬液を利用することにより、水の供給に伴い省力的に施用することもできる。 As for the method of application to paddy rice seedling boxes, the dosage form may vary depending on the time of application, such as application at sowing, application during greening, application at transplanting, etc. It can be applied in a mold. It can also be applied by mixing with the soil, and it can be mixed with the soil and a powder, a granular wettable powder, a granule, etc., such as mixing with bed soil, mixing with soil covering, and mixing with the entire soil. You may simply apply the soil and various preparations in alternating layers.
As for the method of application to rice fields, solid preparations such as jumbo preparations, pack preparations, granules, and wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded rice fields. In addition, at the time of rice planting, a suitable formulation can be sprayed or injected into the soil as it is or mixed with fertilizer. In addition, by using a chemical solution such as an emulsion or a flowable at a source where water flows into a rice field, such as a water outlet or an irrigation system, it can be applied in a labor-saving manner as water is supplied.
畑作物においては、播種から育苗期において、種子又は植物体に近接する栽培担体等へ処理ができる。畑に直接播種する植物においては、種子への直接処理の他、栽培中の植物の株元への処理が好適である。粒剤を用いて散布処理又は水に希釈あるいは希釈しない薬剤を液状にて潅注処理を行うこと等ができる。粒剤を播種前の栽培担体と混和させた後、播種するのも好ましい処理である。
移植を行う栽培植物の播種、育苗期の処理としては、種子への直接処理の他、育苗用苗床への、液状とした薬剤の潅注処理又は粒剤の散布処理が好ましい。また、定植時に粒剤を植え穴に処理をしたり、移植場所近辺の栽培担体に混和することも好ましい処理である。
本発明の農園芸用害虫防除剤は、農薬製剤上の常法に従い使用上都合の良い形状に製剤して使用するのが一般的である。
即ち、本発明の一般式(1)で表される化合物又はその塩類はこれらを適当な不活性担体に、又は必要に応じて補助剤と一緒に適当な割合に配合して溶解、分離、懸濁、混合、含浸、吸着若しくは付着させて適宜の剤型、例えば懸濁剤、乳剤、液剤、水和剤、顆粒水和剤、粒剤、粉剤、錠剤、パック剤等に製剤して使用すれば良い。 In field crops, seeds or cultivation carriers close to the plants can be treated during the seeding to seedling-raising period. For plants that are directly sown in fields, in addition to direct treatment to seeds, treatment to the roots of plants under cultivation is suitable. Spraying treatment can be performed using granules, or irrigation treatment can be carried out in liquid form by diluting or not diluting the agent with water. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow the seeds.
Treatments during the sowing and seedling-raising stages of cultivated plants to be transplanted include direct treatment of seeds, as well as irrigation treatment with liquid chemicals or spraying treatment with granules on seedling beds. It is also preferable to apply granules to the planting hole at the time of planting, or to mix them into the cultivation carrier near the transplant site.
The agricultural and horticultural pest control agent of the present invention is generally formulated into a form convenient for use according to conventional methods for pesticide formulations.
That is, the compound represented by the general formula (1) of the present invention or its salts can be dissolved, separated, or suspended by blending them in an appropriate inert carrier or with an adjuvant as necessary in an appropriate ratio. It can be used by clouding, mixing, impregnating, adsorbing or adhering it into an appropriate dosage form, such as suspension, emulsion, liquid, wettable powder, wettable powder, granule, powder, tablet, pack, etc. Good.
移植を行う栽培植物の播種、育苗期の処理としては、種子への直接処理の他、育苗用苗床への、液状とした薬剤の潅注処理又は粒剤の散布処理が好ましい。また、定植時に粒剤を植え穴に処理をしたり、移植場所近辺の栽培担体に混和することも好ましい処理である。
本発明の農園芸用害虫防除剤は、農薬製剤上の常法に従い使用上都合の良い形状に製剤して使用するのが一般的である。
即ち、本発明の一般式(1)で表される化合物又はその塩類はこれらを適当な不活性担体に、又は必要に応じて補助剤と一緒に適当な割合に配合して溶解、分離、懸濁、混合、含浸、吸着若しくは付着させて適宜の剤型、例えば懸濁剤、乳剤、液剤、水和剤、顆粒水和剤、粒剤、粉剤、錠剤、パック剤等に製剤して使用すれば良い。 In field crops, seeds or cultivation carriers close to the plants can be treated during the seeding to seedling-raising period. For plants that are directly sown in fields, in addition to direct treatment to seeds, treatment to the roots of plants under cultivation is suitable. Spraying treatment can be performed using granules, or irrigation treatment can be carried out in liquid form by diluting or not diluting the agent with water. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow the seeds.
Treatments during the sowing and seedling-raising stages of cultivated plants to be transplanted include direct treatment of seeds, as well as irrigation treatment with liquid chemicals or spraying treatment with granules on seedling beds. It is also preferable to apply granules to the planting hole at the time of planting, or to mix them into the cultivation carrier near the transplant site.
The agricultural and horticultural pest control agent of the present invention is generally formulated into a form convenient for use according to conventional methods for pesticide formulations.
That is, the compound represented by the general formula (1) of the present invention or its salts can be dissolved, separated, or suspended by blending them in an appropriate inert carrier or with an adjuvant as necessary in an appropriate ratio. It can be used by clouding, mixing, impregnating, adsorbing or adhering it into an appropriate dosage form, such as suspension, emulsion, liquid, wettable powder, wettable powder, granule, powder, tablet, pack, etc. Good.
本発明の農園芸用害虫防除剤は、有効成分の他に必要に応じて農薬製剤に通常用いられる添加成分を含有することができる。この添加成分としては、固体担体、液体担体等の担体、界面活性剤、分散剤、湿潤剤、結合剤、粘着付与剤、増粘剤、着色剤、拡展剤、展着剤、凍結防止剤、固結防止剤、崩壊剤、分解防止剤等が挙げられる。その他必要に応じ、防腐剤、植物片等を添加成分に用いてもよい。これらの添加成分は単独で用いてもよいし、また、2種以上を組み合わせて用いてもよい。
In addition to the active ingredients, the agricultural and horticultural pest control agent of the present invention may contain additive components commonly used in agricultural chemical formulations, if necessary. These additive components include carriers such as solid carriers and liquid carriers, surfactants, dispersants, wetting agents, binders, tackifiers, thickeners, colorants, spreading agents, spreading agents, and antifreeze agents. , anti-caking agents, disintegrants, anti-decomposition agents and the like. Other additives such as preservatives and plant pieces may be used as necessary. These additive components may be used alone or in combination of two or more.
固体担体としては、例えば石英、クレー、カオリナイト、ピロフィライト、セリサイト、タルク、ベントナイト、酸性白土、アタパルジャイト、ゼオライト、珪藻土等の天然鉱物類、炭酸カルシウム、硫酸アンモニウム、硫酸ナトリウム、塩化カリウム等の無機塩類、合成ケイ酸、合成ケイ酸塩、デンプン、セルロース、植物粉末(例えばおがくず、ヤシガラ、トウモロコシ穂軸、タバコ茎等)等の有機固体担体、ポリエチレン、ポリプロピレン、ポリ塩化ビニリデン等のプラスチック担体、尿素、無機中空体、プラスチック中空体、フュームド シリカ(fumed silica, ホワイトカーボン)等が挙げられる。これらは単独で用いてもよいし、また、2種以上を組み合わせて用いてもよい。
Examples of solid carriers include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, and diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride. , synthetic silicic acid, synthetic silicates, starch, cellulose, organic solid carriers such as vegetable powders (e.g. sawdust, coconut shell, corncob, tobacco stalk, etc.), plastic carriers such as polyethylene, polypropylene, polyvinylidene chloride, urea, Examples include inorganic hollow bodies, plastic hollow bodies, fumed silica (white carbon), etc. These may be used alone or in combination of two or more.
液体担体としては、例えば、メタノール、エタノール、プロパノール、イソプロパノール、ブタノール等の一価アルコール類や、エチレングリコール、ジエチレングリコール、プロピレングリコール、ヘキシレングリコール、ポリエチレングリコール、ポリプロピレングリコール、グリセリン等の多価アルコール類のようなアルコール類、プロピレングリコールエーテル等の多価アルコール化合物類、アセトン、メチルエチルケトン、メチルイソブチルケトン、ジイソブチルケトン、シクロヘキサノン等のケトン類、エチルエーテル、ジオキサン、エチレングリコールモノエチルエーテル、ジプロピルエーテル、THF等のエーテル類、ノルマルパラフィン、ナフテン、イソパラフィン、ケロシン、鉱油等の脂肪族炭化水素類、ベンゼン、トルエン、キシレン、ソルベントナフサ、アルキルナフタレン等の芳香族炭化水素類、ジクロロメタン、クロロホルム、四塩化炭素等のハロゲン化炭化水素類、酢酸エチル、ジイソプロピルフタレート、ジブチルフタレート、ジオクチルフタレート、アジピン酸ジメチル等のエステル類、γ‐ブチロラクトン等のラクトン類、ジメチルホルムアミド、ジエチルホルムアミド、ジメチルアセトアミド、N‐アルキルピロリジノン等のアミド類、アセトニトリル等のニトリル類、ジメチルスルホキシド等の硫黄化合物類、大豆油、ナタネ油、綿実油、ヒマシ油等の植物油、水等を挙げることができる。これらは単独で用いてもよいし、また、2種以上を組み合わせて用いてもよい。
Examples of liquid carriers include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin. alcohols, polyhydric alcohol compounds such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, THF, etc. ethers, normal paraffin, naphthene, isoparaffin, kerosene, aliphatic hydrocarbons such as mineral oil, aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, dichloromethane, chloroform, carbon tetrachloride, etc. Halogenated hydrocarbons, esters such as ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, lactones such as γ-butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, etc. Examples include nitriles such as acetonitrile, sulfur compounds such as dimethyl sulfoxide, vegetable oils such as soybean oil, rapeseed oil, cottonseed oil, and castor oil, and water. These may be used alone or in combination of two or more.
分散剤や湿展剤として用いる界面活性剤としては、例えばソルビタン脂肪酸エステル、ポリオキシエチレンソルビタン脂肪酸エステル、ショ糖脂肪酸エステル、ポリオキシエチレン脂肪酸エステル、ポリオキシエチレン樹脂酸エステル、ポリオキシエチレン脂肪酸ジエステル、ポリオキシエチレンアルキルエーテル、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンアルキルフェニルエーテル、ポリオキシエチレンジアルキルフェニルエーテル、ポリオキシエチレンアルキルフェニルエーテルホルマリン縮合物、ポリオキシエチレンポリオキシプロピレンブロックコポリマー、ポリスチレンポリオキシエチレンブロックポリマー、アルキルポリオキシエチレンポリプロピレンブロックコポリマーエーテル、ポリオキシエチレンアルキルアミン、ポリオキシエチレン脂肪酸アミド、ポリオキシエチレン脂肪酸ビスフェニルエーテル、ポリアルキレンベンジルフェニルエーテル、ポリオキシアルキレンスチリルフェニルエーテル、アセチレンジオール、ポリオキシアルキレン付加アセチレンジオール、ポリオキシエチレンエーテル型シリコーン、エステル型シリコーン、フッ素系界面活性剤、ポリオキシエチレンひまし油、ポリオキシエチレン硬化ひまし油等の非イオン性界面活性剤、アルキル硫酸塩、ポリオキシエチレンアルキルエーテル硫酸塩、ポリオキシエチレンアルキルフェニルエーテル硫酸塩、ポリオキシエチレンスチリルフェニルエーテル硫酸塩、アルキルベンゼンスルホン酸塩、アルキルアリールスルホン酸塩、リグニンスルホン酸塩、アルキルスルホコハク酸塩、ナフタレンスルホン酸塩、アルキルナフタレンスルホン酸塩、ナフタレンスルホン酸のホルマリン縮合物の塩、アルキルナフタレンスルホン酸のホルマリン縮合物の塩、脂肪酸塩、ポリカルボン酸塩、ポリアクリル酸塩、N‐メチル‐脂肪酸サルコシネート、樹脂酸塩、ポリオキシエチレンアルキルエーテルリン酸塩、ポリオキシエチレンアルキルフェニルエーテルリン酸塩等のアニオン性界面活性剤、ラウリルアミン塩酸塩、ステアリルアミン塩酸塩、オレイルアミン塩酸塩、ステアリルアミン酢酸塩、ステアリルアミノプロピルアミン酢酸塩、アルキルトリメチルアンモニウムクロライド、アルキルジメチルベンザルコニウムクロライド等のアルキルアミン塩等のカチオン界面活性剤、アミノ酸型又はベタイン型等の両性界面活性剤等が挙げられる。これらの界面活性剤は単独で用いてもよいし、また、2種以上を組み合わせて用いてもよい。
Examples of surfactants used as dispersants and wetting agents include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, Polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzylphenyl ether, polyoxyalkylene styryl phenyl ether, acetylene diol, polyoxy Alkylene-added acetylene diol, polyoxyethylene ether silicone, ester silicone, fluorine surfactant, nonionic surfactant such as polyoxyethylene castor oil, polyoxyethylene hydrogenated castor oil, alkyl sulfate, polyoxyethylene alkyl ether Sulfate, polyoxyethylene alkylphenyl ether sulfate, polyoxyethylene styryl phenyl ether sulfate, alkylbenzene sulfonate, alkylaryl sulfonate, lignin sulfonate, alkyl sulfosuccinate, naphthalene sulfonate, alkylnaphthalene sulfone acid salts, salts of formalin condensates of naphthalenesulfonic acids, salts of formalin condensates of alkylnaphthalenesulfonic acids, fatty acid salts, polycarboxylic acid salts, polyacrylates, N-methyl-fatty acid sarcosinates, resinates, polyoxy Anionic surfactants such as ethylene alkyl ether phosphate, polyoxyethylene alkyl phenyl ether phosphate, laurylamine hydrochloride, stearylamine hydrochloride, oleylamine hydrochloride, stearylamine acetate, stearylamine propylamine acetate, Examples include cationic surfactants such as alkylamine salts such as alkyltrimethylammonium chloride and alkyldimethylbenzalkonium chloride, and amphoteric surfactants such as amino acid type or betaine type. These surfactants may be used alone or in combination of two or more.
結合剤や粘着付与剤としては、例えばカルボキシメチルセルロースやその塩、デキストリン、水溶性デンプン、キサンタンガム、グアーガム、蔗糖、ポリビニルピロリドン、アラビアゴム、ポリビニルアルコール、ポリビニルアセテート、ポリアクリル酸ナトリウム、平均分子量6000~20000のポリエチレングリコール、平均分子量10万~500万のポリエチレンオキサイド、燐脂質(例えばセファリン、レシチン等)セルロース粉末、デキストリン、加工デンプン、ポリアミノカルボン酸キレート化合物、架橋ポリビニルピロリドン、マレイン酸とスチレン類の共重合体、(メタ)アクリル酸系共重合体、多価アルコールからなるポリマーとジカルボン酸無水物とのハーフエステル、ポリスチレンスルホン酸の水溶性塩、パラフィン、テルペン、ポリアミド樹脂、ポリアクリル酸塩、ポリオキシエチレン、ワックス、ポリビニルアルキルエーテル、アルキルフェノールホルマリン縮合物、合成樹脂エマルション等が挙げられる。
Examples of binders and tackifiers include carboxymethylcellulose and its salts, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinylpyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and average molecular weight of 6,000 to 20,000. polyethylene glycol, polyethylene oxide with an average molecular weight of 100,000 to 5 million, phospholipids (e.g. cephalin, lecithin, etc.) cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compounds, cross-linked polyvinylpyrrolidone, copolymerization of maleic acid and styrenes. (meth)acrylic acid copolymers, half esters of polyhydric alcohol polymers and dicarboxylic anhydrides, water-soluble salts of polystyrene sulfonic acid, paraffins, terpenes, polyamide resins, polyacrylates, polyoxy Examples include ethylene, wax, polyvinyl alkyl ether, alkylphenol formalin condensate, and synthetic resin emulsion.
増粘剤としては、例えばキサンタンガム、グアーガム、ダイユウタンガム、カルボキシメチルセルロース、ポリビニルピロリドン、カルボキシビニルポリマー、アクリル系ポリマー、デンプン化合物、多糖類のような水溶性高分子、高純度ベントナイト、フュームド シリカ(fumed silica, ホワイトカーボン)のような無機微粉等が挙げられる。
Examples of thickeners include water-soluble polymers such as xanthan gum, guar gum, diurtan gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymers, acrylic polymers, starch compounds, polysaccharides, high-purity bentonite, and fumed silica. Inorganic fine powders such as silica, white carbon, etc.
着色剤としては、例えば酸化鉄、酸化チタン、プルシアンブルーのような無機顔料、アリザリン染料、アゾ染料、金属フタロシアニン染料のような有機染料等が挙げられる。
Examples of the coloring agent include inorganic pigments such as iron oxide, titanium oxide, and Prussian blue, and organic dyes such as alizarin dyes, azo dyes, and metal phthalocyanine dyes.
凍結防止剤としては、例えば、エチレングリコール、ジエチレングリコール、プロピレングリコール、グリセリン等の多価アルコール類等が挙げられる。
Examples of antifreeze agents include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
固結防止や崩壊促進のための補助剤としては、例えばデンプン、アルギン酸、マンノース、ガラクトース等の多糖類、ポリビニルピロリドン、フュームド シリカ(fumed silica, ホワイトカーボン)、エステルガム、石油樹脂、トリポリリン酸ナトリウム、ヘキサメタリン酸ナトリウム、ステアリン酸金属塩、セルロース粉末、デキストリン、メタクリル酸エステルの共重合体、ポリビニルピロリドン、ポリアミノカルボン酸キレート化合物、スルホン化スチレン・イソブチレン・無水マレイン酸共重合体、デンプン・ポリアクリロニトリルグラフト共重合体等が挙げられる。
Examples of adjuvants to prevent caking and promote disintegration include starch, alginic acid, polysaccharides such as mannose and galactose, polyvinylpyrrolidone, fumed silica (white carbon), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylic acid ester copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene/isobutylene/maleic anhydride copolymer, starch/polyacrylonitrile graft copolymer Examples include polymers.
分解防止剤としては、例えばゼオライト、生石灰、酸化マグネシウムのような乾燥剤、フェノール化合物、アミン化合物、硫黄化合物、リン酸化合物等の酸化防止剤、サリチル酸化合物、ベンゾフェノン化合物等の紫外線吸収剤等が挙げられる。
Examples of decomposition inhibitors include drying agents such as zeolite, quicklime, and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds, and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It will be done.
防腐剤としては、例えばソルビン酸カリウム、1,2‐ベンゾチアゾリン‐3‐オン等が挙げられる。
更に必要に応じて機能性展着剤、ピペロニルブトキサイド等の代謝分解阻害剤等の活性増強剤、プロピレングリコール等の凍結防止剤、BHT等の酸化防止剤、紫外線吸収剤等その他の補助剤も使用することができる。 Examples of preservatives include potassium sorbate and 1,2-benzothiazolin-3-one.
Furthermore, as necessary, other aids such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreeze agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers, etc. Agents can also be used.
更に必要に応じて機能性展着剤、ピペロニルブトキサイド等の代謝分解阻害剤等の活性増強剤、プロピレングリコール等の凍結防止剤、BHT等の酸化防止剤、紫外線吸収剤等その他の補助剤も使用することができる。 Examples of preservatives include potassium sorbate and 1,2-benzothiazolin-3-one.
Furthermore, as necessary, other aids such as functional spreading agents, activity enhancers such as metabolic decomposition inhibitors such as piperonyl butoxide, antifreeze agents such as propylene glycol, antioxidants such as BHT, and ultraviolet absorbers, etc. Agents can also be used.
有効成分化合物の配合割合は必要に応じて加減することができ、本発明の農園芸用害虫防除剤100重量部中、0.01~90重量部の範囲から適宜選択して使用すれば良く、例えば、粉剤、粒剤、乳剤又は水和剤とする場合は0.01~50重量部(農園芸用害虫防除剤全体の重量に対して0.01~50重量%)が適当である。
The blending ratio of the active ingredient compound can be adjusted as necessary, and it may be used by appropriately selecting from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural pest control agent of the present invention. For example, when preparing powders, granules, emulsions, or wettable powders, the appropriate amount is 0.01 to 50 parts by weight (0.01 to 50% by weight based on the total weight of the agricultural and horticultural pest control agent).
本発明の農園芸用害虫防除剤の使用量は種々の因子、例えば目的、対象害虫、作物の生育状況、害虫の発生傾向、天候、環境条件、剤型、施用方法、施用場所、施用時期等により変動するが、有効成分化合物として10アール当たり0.001g~10kg、好ましくは0.01g~1kgの範囲から目的に応じて適宜選択すれば良い。
本発明の農園芸用害虫防除剤は、防除対象病害虫、防除適期の拡大のため、或いは薬量の低減をはかる目的で他の農園芸用殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、生物農薬等と混合して使用することも可能であり、また、使用場面に応じて除草剤、植物成長調節剤、肥料等と混合して使用することも可能である。 The amount of the agricultural and horticultural pest control agent of the present invention to be used depends on various factors, such as purpose, target pests, crop growth conditions, pest outbreak trends, weather, environmental conditions, dosage form, application method, application location, application timing, etc. Depending on the purpose, the amount of the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, per 10 ares.
The agricultural and horticultural pest control agent of the present invention can be used in combination with other agricultural and horticultural insecticides, acaricides, nematicides, and fungicides for the purpose of expanding the pests to be controlled and the appropriate period for control, or reducing the amount of pesticides. , biological pesticides, etc., and can also be used in combination with herbicides, plant growth regulators, fertilizers, etc. depending on the usage situation.
本発明の農園芸用害虫防除剤は、防除対象病害虫、防除適期の拡大のため、或いは薬量の低減をはかる目的で他の農園芸用殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、生物農薬等と混合して使用することも可能であり、また、使用場面に応じて除草剤、植物成長調節剤、肥料等と混合して使用することも可能である。 The amount of the agricultural and horticultural pest control agent of the present invention to be used depends on various factors, such as purpose, target pests, crop growth conditions, pest outbreak trends, weather, environmental conditions, dosage form, application method, application location, application timing, etc. Depending on the purpose, the amount of the active ingredient compound may be appropriately selected from the range of 0.001 g to 10 kg, preferably 0.01 g to 1 kg, per 10 ares.
The agricultural and horticultural pest control agent of the present invention can be used in combination with other agricultural and horticultural insecticides, acaricides, nematicides, and fungicides for the purpose of expanding the pests to be controlled and the appropriate period for control, or reducing the amount of pesticides. , biological pesticides, etc., and can also be used in combination with herbicides, plant growth regulators, fertilizers, etc. depending on the usage situation.
かかる目的で使用する他の農園芸殺虫剤、殺ダニ剤、殺線虫剤として例えば、3,5-キシリルメチルカルバメイト(3,5-xylyl methylcarbamate,XMC)、フェノブカルブ(fenobucarb,BPMC)、Btトキシン系殺虫性化合物、CPCBS(chlorfenson)、DCIP(dichlorodiisopropyl ether)、D-D(1,3-Dichloropropene)、DDT、NAC、O-4-dimethylsulfamoylphenyl O,O-diethyl phosphorothioate(DSP)、O-ethyl O-4-nitrophenyl phenylphosphonothioate(EPN)、tripropylisocyanurate(TPIC)、アクリナトリン(acrinathrin)、アザディラクチン(azadirachtin)、アシノナピル(acynonapyr) 、アジンホス・メチル(azinphos-methyl)、アセキノシル(acequinocyl)、アセタミプリド(acetamiprid)、アセトプロール(acetoprole)、アセフェート(acephate)、アバメクチン(abamectin)、アフィドピロペン(afidopyropen)、アベルメクチン(avermectin-B)、アミドフルメット(amidoflumet)、アミトラズ(amitraz)、アラニカルブ(alanycarb)、アルジカルブ(aldicarb)、アルドキシカルブ(aldoxycarb)、アルドリン(aldrin)、アルファーエンドスルファン(alpha-endosulfan)、アルファシペルメトリン(alpha-cypermethrin)、アルベンダゾール(albendazole)、アレスリン(allethrin)、イサゾホス(isazofos)、イサミドホス(isamidofos)、イソアミドホス(isoamidofos)、イソキサチオン(isoxathion)、イソシクロセラム(isocycloseram) 、イソフェンホス(isofenphos)、イソプロカルブ(isoprocarb: MIPC)、イプシロン-メトフルトリン(epsilon-metofluthrin)、イプシロン-モンフルトリン(epsilon-momfluorothrin)、イベルメクチン(ivermectin)、イミシアホス(imicyafos)、イミダクロプリド(imidac1oprid)、イミプロトリン(imiprothrin)、インダザピロキサメト(indazapyroxamet)、インドキサカルブ(indoxacarb)、エスフェンバレレート(esfenvalerate)、エチオフェンカルブ(ethiofencarb)、エチオン(ethion)、エチプロール(ethiprole)、エトキサゾール(etoxazole)、エトフェンプロックス(ethofenprox)、エトプロホス(ethoprophos)、エトリムホス(etrimfos)、エマメクチン(emamectin)、エマメクチンベンゾエート(emamectin-benzoate)、エンドスルファン(endosulfan)、エンペントリン(empenthrin)、オキサゾスルフィル(oxazosulfyl) 、オキサミル(oxamyl)、オキシジメトン・メチル(oxydemeton-methyl)、オキシデプロホス(oxydeprofos: ESP)、オキシベンダゾール(oxibendazole)、オクスフェンダゾール(oxfendazole)、オレイン酸カリウム(Potassium oleate)、オレイン酸ナトリウム(sodium oleate)、カズサホス(cadusafos)、カッパ-ビフェントリン(kappa-bifenthrin)、カルタップ(cartap)、カルバリル(carbary1)、カルボスルファン(carbosulfan)、カルボフラン(carbofuran)、ガンマシハロトリン(gamma-cyhalothrin)、キシリルカルブ(xylylcarb)、キナルホス(quinalphos)、キノプレン(kinoprene)、キノメチオネート(chinomethionat)、クロエトカルブ(cloethocarb)、クロチアニジン(clothianidin)、クロフェンテジン(clofentezine)、クロマフェノジド(chromafenozide)、クロラントラニリプロール(chlorantraniliprole)、クロルエトキシホス(chlorethoxyfos)、クロルジメホルム(chlordimeform)、クロルデン(chlordane)、クロルピリホス(chlorpyrifos)、クロルピリホス-メチル(chlorpyrifos-methyl)、クロルフェナピル(chlorphenapyr)、クロルフェンソン(chlorfenson)、クロルフェンビンホス(ch1orfenvinphos)、クロルフルアズロン(chlorfluazuron)、クロルベンジレート(chlorobenzilate)、クロロベンゾエート(chlorobenzoate)、クロロプラレトリン(chloroprallethrin)、ケルセン(ジコホル: dicofol)、サリチオン(salithion)、シハロジアミド(cyhalodiamide)、シアノホス(cyanophos: CYAP)、ジアフェンチウロン(diafenthiuron)、ジアミダホス(diamidafos)、シアントラニリプロール(cyantraniliprole)、シータ-シペルメトリン(theta-cypermethrin)、ジエノクロル(dienochlor)、シエトピラフェン(cyetpyrafen)、シエノピラフェン(cyenopyrafen)、ジオキサベンゾホス(dioxabenzofos)、ジオフェノラン(diofenolan)、シグマ-シペルメトリン(sigma-cypermethrin)、シクラニリプロール(cyclaniliprole)、ジクロフェンチオン(dichlofenthion: ECP)、シクロプロトリン(cycloprothrin)、ジクロルボス(dichlorvos: DDVP)、ジクロロメゾティアズ(dicloromezotiaz)、ジスルホトン(disulfoton)、ジノテフラン(dinotefuran)、シハロジアミド(cyhalodiamide)、シハロトリン(cyhalothrin)、シフェノトリン(cyphenothrin)、シフルトリン(cyfluthrin)、ジフルベンズロン(diflubenzuron)、シフルメトフェン(cyflumetofen)、ジフロビダジン(diflovidazin)、シプロフラニリド(cyproflanilide)、シヘキサチン(cyhexatin)、シペルメトリン(cypermethrin)、ジメチルビンホス(dimethylvinphos)、ジメトエート(dimethoate)、ジムプロピリダヅ(dimpropyridaz) 、ジメフルスリン(dimefluthrin)、シラフルオフェン(silafluofen)、シロマジン(cyromazine)、スピドキサマト(spidoxamat)、スピネトラム(spinetoram)、スピノサッド(spinosad)、スピロジクロフェン(spirodiclofen)、スピロテトラマト(spirotetramat)、スピロピジオン(spiropidion)、スピロブジフェン(spirobudifen)、スピロメシフェン(spiromesifen)、スルフィフラミン(sulfiflumin)、スルフルラミド(sulfluramid)、スルプロホス(sulprofos)、スルホキサフロール(sulfoxaflor)、ゼータ-シペルメトリン(zeta-cypermethrin)、ダイアジノン(diazinon)、タウフルバリネート(tau-fluvalinate)、ダゾメット(dazomet)、チアクロプリド(thiacloprid)、チアメトキサム(thiamethoxam)、チオキサザフェン(tioxazafen)、チオジカルブ(thiodicarb)、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)、チオナジン(thionazin)、チオメトン(thiometon)、チオラントラニリプロール(tiorantraniliprole)、ディート(deet)、ディルドリン(dieldrin)、テトラクロラントラニリプロール(tetrachlorantraniliprole)、チクロピラゾフロル(tyclopyrazoflor)、テトラクロルビンホス(tetrach1orvinphos)、テトラジホン(tetradifon)、テトラニリプロール(tetraniliprole)、テトラメチルフルトリン(tetramethylfluthrin)、テトラメトリン(tetramethrin)、テブピリムホス(tebupirimfos)、テブフェノジド(tebufenozide)、テブフェンピラド(tebufenpyrad)、テフルトリン(tefluthrin)、テフルベンズロン(teflubenzuron)、デメトン-S-メチル(demeton-S-methyl)、テメホス(temephos)、デルタメトリン(deltamethrin)、テルブホス(terbufos)、ドラメクチン(doramectin)、トラロピリル(tralopyril)、トラロメトリン(tralomethrin)、トランスフルトリン(transfluthrin)、トリアザメート(triazamate)、トリアズロン(triazuron)、トリクラミド(trichlamide)、トリクロルホン(trichlorphon: DEP)、トリフルエンフロネート(trifluenfuronate)、トリフルメゾピリム(triflumezopyrium)、トリフルムロン(triflumuron)、トルフェンピラド(tolfenpyrad)、ナレッド(naled: BRP)、ニコフルプロール(nicofluprole)、ニチアジン(nithiazine)、ニテンピラム(nitenpyram)、ノバルロン(novaluron)、ノビフルムロン(noviflumuron)、ハイドロプレン(hydroprene)、バニリプロール(vaniliprole)、バミドチオン(vamidothion)、パラチオン(parathion)、パラチオン-メチル(parathion-methyl)、ハルフェンプロックス(halfenprox)、ハロフェノジド(halofenozide)、ビストリフルロン(bistrifluron)、ビスルタップ(bisultap)、ヒドラメチルノン(hydramethylnon)、ヒドロキシプロピルデンプン(hydroxy propyl starch)、ビナパクリル(binapacryl)、ピフルブミド(pyflubumide)、ビフェナゼート(bifenazate)、ビフェントリン(bifenthrin)、ピメトロジン(pymetrozine)、ピラクロホス(pyraclorfos)、ピラフルプロール(pyrafluprole)、ピリダフェンチオン(pyridafenthion)、ピリダベン(pyridaben)、ピリダリル(pyridalyl)、ピリフルキナゾン(pyrifluquinazon)、ピリプロール(pyriprole)、ピリプロキシフェン(pyriproxyfen)、ピリミカーブ(pirimicarb)、ピリミジフェン(pyrimidifen)、ピリミノストロビン(pyriminostrobin)、ピリミホスメチル(pirimiphos-methy1)、ピレトリン(pyrethrins)、フィプロニル(fiproni1)、フェナザキン(fenazaquin)、フェナミフォス(fenamiphos)、フェニソブロモレート(bromopropylate)、フェニトロチオン(fenitrothion: MEP)、フェノキシカルブ(fenoxycarb)、フェノチオカルブ(fenothiocarb)、フェノトリン(phenothrin)、フェノブカルブ(fenobucarb)、フェンスルフォチオン(fensulfothion)、フェンチオン(fenthion: MPP)、フェントエート(phenthoate: PAP)、フェンバレレート(fenvalerate)、フェンピロキシメート(fenpyroximate)、フェンプロパトリン(fenpropathrin)、フェンベンダゾール(fenbendazole)、フェンメゾジチアズ(fenmezoditiaz)、フォスチアゼート(fosthiazate)、フォルメタネート(formetanate)、ブタチオホス(butathiofos) 、ブプロフェジン(buprofezin)、フラチオカルブ(furathiocarb)、プラレトリン(prallethrin)、フルアクリピリム(fluacrypyrim)、フラザインドリジン(fluazaindolizine)、フルアジナム(fluazinam)、フルアズロン(fluazuron)、フルエンスルホン(fluensulfone)、フルキサメタミド(fluxametamide)、フルクロルジニリプロール(fluchlordiniliprole)、フルシクロクスロン(flucycloxuron)、フルシトリネート(flucythrinate)、フルバリネート(fluvalinate)、フルピラジフロン(flupyradifurone)、フルフィプロール(flufiprole)、フルピラジフロン(flupyradifurone)、フルピラゾホス(flupyrazofos)、フルピリミン(flupyrimin)、フルピロキシストロビン(flupyroxysrobin)、フルフェネリム(flufenerim)、フルフェノキシストロビン(flufenoxystrobin)、フルフェノクスロン(flufenoxuron)、フルフェンジン(flufenzine)、フルフェンプロックス(flufenoprox)、フルプロキシフェン(fluproxyfen)、フルブロシスリネート(flubrocythrinate)、フルヘキサホン(fluhexafon)、フルベンジアミド(flubendiamide)、フルペンチオフェノックス(flupentiofenox)、フルメトリン(flumethrin)、フルリムフェン(flurimfen)、プロチオホス(prothiofos)、プロトリフェンブト(protrifenbute)、フロニカミド(flonicamid)、プロパホス(propaphos)、プロパルギット(propargite: BPPS)、プロフェノホス(profenofos)、ブロフラニリド(broflanilide)、プロフルスリン(profluthrin)、プロポキスル(propoxur: PHC)、フロメトキン(flometoquin)、α-ブロマディオロン(alpha-bromadiolone)、ブロモプロピレート(bromopropylate)、ベータ-シフルトリン(beta-cyfluthrin)、ヘキサフルムロン(hexaflumuron)、ヘキシチアゾクス(hexythiazox)、ヘプタフルトリン(heptafluthrin)、ヘプテノホス(heptenophos)、ペルメトリン(permethrin)、ベンクロチアズ(benclothiaz)、ベンジオカルブ(bendiocarb)、ベンズピリモキサン(benzpyrimoxan)、ベンスルタップ(bensu1tap)、ベンゾキシメート(benzoximate)、ベンフラカルブ(benfuracarb)、ホキシム(phoxim)、ホサロン(phosalone)、ホスチアゼート(fosthiazate)、ホスチエタン(fosthietan)、ホスファミドン(phosphamidon)、ホスホカルブ(phosphocarb)、ホスメット(phosmet: PMP)、ポリナクチン複合体(polynactins)、ホルメタネート(formetanate)、ホルモチオン(formothion)、ホレート(phorate)、マシン油(machine oil)、マラチオン(malathion)、ミルベマイシン(milbemycin)、ミルベマイシンA(milbemycin-A)、ミルベメクチン(milbemectin)、メカルバム(mecarbam)、メスルフェンホス(mesulfenfos)、メソミル(methomyl)、メタアルデヒド(metaldehyde)、メタフルミゾン(metaflumizone)、メタミドホス(methamidophos)、メタム・アンモニウム(metam-ammonium)、メタム・ナトリウム(metam-sodium)、メチオカルブ(methiocarb)、メチダチオン(methidathion: DMTP)、メチルイソチオシアネート(methylisothiocyanate)、メチルネオデカナミド(methylneodecanamide)、メチル
パラチオン(methylparathion)、メトキサジアゾン(metoxadiazone)、メトキシクロル(methoxychlor)、メトキシフェノジド(methoxyfenozide)、メトフルトリン(metofluthrin)、メトプレン(methoprene)、メトルカルブ(metolcarb)、メペルフルスリン(meperfluthrin)、メビンホス(mevinphos)、モノクロトホス(monocrotophos)、モノスルタップ(monosultap)、モムフルオロスリン(momfluorothrin)、ラムダ-シハロトリン(lambda-cyhalothrin)、リアノジン(ryanodine)、ルフェヌロン(lufenuron)、レスカルール(rescalure)、レスメトリン(resmethrin)、レピメクチン(lepimectin)、ロテノン(rotenone)、塩酸レバミゾール(levamisol hydrochloride)、酸化フェンブタスズ(fenbutatin oxide)、酒石酸モランテル(morantel tartarate)、臭化メチル(methyl bromide)、水酸化トリシクロヘキシルスズ(cyhexatin)、石灰窒素(calcium cyanamide)、石灰硫黄合剤(calcium polysulfide)、硫黄(sulfur)、及び硫酸ニコチン(nicotine-sulfate)等を例示することができる。 Other agricultural and horticultural insecticides, acaricides, and nematicides used for this purpose include, for example, 3,5-xylyl methylcarbamate (XMC), fenobucarb (BPMC), Bt toxin insecticidal compounds, CPCBS (chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1,3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), O-ethyl O -4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, acynonapyr, azinphos-methyl, acequinocyl, acetamiprid, Acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanycarb, aldicarb, aldo aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isamidophos (isoamidofos), isoxathion, isocycloseram, isofenphos, isoprocarb (MIPC), epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin , imicyafos, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, esfenvalerate, ethiofencarb, ethion, ethiprole (ethiprole), etoxazole, etofenprox, ethoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, oxa Oxazosulfyl, oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfendazole, Potassium oleate oleate), sodium oleate, cadusafos, kappa-bifenthrin, cartap, carbary1, carbosulfan, carbofuran, gamma cyhalo gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionat, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorfenapyr, chlorfenson , chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, dicofol, salithion, cyhalodiamide (cyhalodiamide), cyanophos (CYAP), diafenthiuron, diamidafos, cyantraniliprole, theta-cypermethrin, dienochlor, cyetpyrafen ), cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, dichlofenthion (ECP), cycloprothrin ), dichlorvos (DDVP), dichloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron ( diflubenzuron), cyflumetofen, diflovidazin, cyproflanilide, cyhexatin, cypermethrin, dimethylvinphos, dimethoate, dimpropyridaz, dimefluthrin rin) , silafluofen, cyromazine, spidoxamat, spinetoram, spinosad, spirodiclofen, spirotetramat, spiropidion, spirobudifen, Spiromesifen, sulfiflumin, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, taufluvalinate ( tau-fluvalinate), dazomet, thiacloprid, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap-sodium, thionazin, thiometon, tiorantraniliprole, DEET, dieldrin, tetrachlorantraniliprole, tyclopyrazoflor, tetrachlorbin Tetrach1orvinphos, tetradifon, tetraniliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, Teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, doramectin, tralopyril, tralomethrin, transflu Transfluthrin, triazamate, triazuron, trichlamide, trichlorphon (DEP), trifluenfuronate, triflumezopyrium, triflumuron, tolfenpyrad ), naled (BRP), nicofluprole, nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, vamidothion ), parathion, parathion-methyl, halfenprox, halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxypropyl starch (hydroxy propyl starch), binapacryl, pyflubumide, bifenazate, bifenthrin, pymetrozine, pyraclorfos, pyrafluprole, pyridafenthion, pyridaben ( pyridaben), pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methy1, Pyrethrins, fipronil, fenazaquin, fenamiphos, bromopropylate, fenitrothion (MEP), fenoxycarb, fenothiocarb, phenothrin , fenobucarb, fensulfothion, fenthion (MPP), phenthoate (PAP), fenvalerate, fenpyroximate, fenpropathrin, fenbendazole ), fenmezoditiaz, fosthiazate, formetate, butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim, furazindo Lysine, fluazinam, fluazuron, fluensulfone, fluxametamide, fluchlordiniliprole, flucycloxuron, flucythrinate, fluvalinate, flupyradifurone, flufiprole, flupyradifurone, flupyrazofos, flupyrimin, flupyroxysrobin, flufenerim, flufenoxystrobin (flufenoxystrobin), flufenoxuron, flufenzine, flufenprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flupentiophenox, flumethrin, flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite (BPPS), profenofos (profenofos), broflanilide, profluthrin, propoxur (PHC), flometoquin, alpha-bromadiolone, bromopropylate, beta-cyfluthrin (beta- cyfluthrin), hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiaz, bendiocarb, benzpyrimoxan, bensultap, benzoximate, benfuracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet : PMP), polynactins, formetanate, formothion, phorate, machine oil, malathion, milbemycin, milbemycin-A , milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam sodium ( metam-sodium), methiocarb, methidathion (DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, metoxadiazone, methoxychlor, methoxyphenozide ( methoxyfenozide), metofluthrin, methoprene, metolcarb, meperfluthrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin ( lambda-cyhalothrin), ryanodine, lufenuron, rescalure, resmethrin, lepimectin, rotenone, levamisol hydrochloride, fenbutatin oxide, tartaric acid Morantel tartarate, methyl bromide, cyhexatin hydroxide, calcium cyanamide, calcium polysulfide, sulfur, and nicotine sulfate. sulfate), etc.
パラチオン(methylparathion)、メトキサジアゾン(metoxadiazone)、メトキシクロル(methoxychlor)、メトキシフェノジド(methoxyfenozide)、メトフルトリン(metofluthrin)、メトプレン(methoprene)、メトルカルブ(metolcarb)、メペルフルスリン(meperfluthrin)、メビンホス(mevinphos)、モノクロトホス(monocrotophos)、モノスルタップ(monosultap)、モムフルオロスリン(momfluorothrin)、ラムダ-シハロトリン(lambda-cyhalothrin)、リアノジン(ryanodine)、ルフェヌロン(lufenuron)、レスカルール(rescalure)、レスメトリン(resmethrin)、レピメクチン(lepimectin)、ロテノン(rotenone)、塩酸レバミゾール(levamisol hydrochloride)、酸化フェンブタスズ(fenbutatin oxide)、酒石酸モランテル(morantel tartarate)、臭化メチル(methyl bromide)、水酸化トリシクロヘキシルスズ(cyhexatin)、石灰窒素(calcium cyanamide)、石灰硫黄合剤(calcium polysulfide)、硫黄(sulfur)、及び硫酸ニコチン(nicotine-sulfate)等を例示することができる。 Other agricultural and horticultural insecticides, acaricides, and nematicides used for this purpose include, for example, 3,5-xylyl methylcarbamate (XMC), fenobucarb (BPMC), Bt toxin insecticidal compounds, CPCBS (chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1,3-Dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), O-ethyl O -4-nitrophenyl phenylphosphonothioate (EPN), tripropylisocyanurate (TPIC), acrinathrin, azadirachtin, acynonapyr, azinphos-methyl, acequinocyl, acetamiprid, Acetoprole, acephate, abamectin, afidopyropen, avermectin-B, amidoflumet, amitraz, alanycarb, aldicarb, aldo aldoxycarb, aldrin, alpha-endosulfan, alpha-cypermethrin, albendazole, allethrin, isazofos, isamidofos, isamidophos (isoamidofos), isoxathion, isocycloseram, isofenphos, isoprocarb (MIPC), epsilon-metofluthrin, epsilon-momfluorothrin, ivermectin , imicyafos, imidacloprid, imiprothrin, indazapyroxamet, indoxacarb, esfenvalerate, ethiofencarb, ethion, ethiprole (ethiprole), etoxazole, etofenprox, ethoprophos, etrimfos, emamectin, emamectin-benzoate, endosulfan, empenthrin, oxa Oxazosulfyl, oxamyl, oxydemeton-methyl, oxydeprofos (ESP), oxibendazole, oxfendazole, Potassium oleate oleate), sodium oleate, cadusafos, kappa-bifenthrin, cartap, carbary1, carbosulfan, carbofuran, gamma cyhalo gamma-cyhalothrin, xylylcarb, quinalphos, kinoprene, chinomethionat, cloethocarb, clothianidin, clofentezine, chromafenozide, chlorantraniliprole, chlorethoxyfos, chlordimeform, chlordane, chlorpyrifos, chlorpyrifos-methyl, chlorfenapyr, chlorfenson , chlorfenvinphos, chlorfluazuron, chlorobenzilate, chlorobenzoate, chloroprallethrin, dicofol, salithion, cyhalodiamide (cyhalodiamide), cyanophos (CYAP), diafenthiuron, diamidafos, cyantraniliprole, theta-cypermethrin, dienochlor, cyetpyrafen ), cyenopyrafen, dioxabenzofos, diofenolan, sigma-cypermethrin, cyclaniliprole, dichlofenthion (ECP), cycloprothrin ), dichlorvos (DDVP), dichloromezotiaz, disulfoton, dinotefuran, cyhalodiamide, cyhalothrin, cyphenothrin, cyfluthrin, diflubenzuron ( diflubenzuron), cyflumetofen, diflovidazin, cyproflanilide, cyhexatin, cypermethrin, dimethylvinphos, dimethoate, dimpropyridaz, dimefluthrin rin) , silafluofen, cyromazine, spidoxamat, spinetoram, spinosad, spirodiclofen, spirotetramat, spiropidion, spirobudifen, Spiromesifen, sulfiflumin, sulfluramid, sulprofos, sulfoxaflor, zeta-cypermethrin, diazinon, taufluvalinate ( tau-fluvalinate), dazomet, thiacloprid, thiamethoxam, tioxazafen, thiodicarb, thiocyclam, thiosultap, thiosultap-sodium, thionazin, thiometon, tiorantraniliprole, DEET, dieldrin, tetrachlorantraniliprole, tyclopyrazoflor, tetrachlorbin Tetrach1orvinphos, tetradifon, tetraniliprole, tetramethylfluthrin, tetramethrin, tebupirimfos, tebufenozide, tebufenpyrad, tefluthrin, Teflubenzuron, demeton-S-methyl, temephos, deltamethrin, terbufos, doramectin, tralopyril, tralomethrin, transflu Transfluthrin, triazamate, triazuron, trichlamide, trichlorphon (DEP), trifluenfuronate, triflumezopyrium, triflumuron, tolfenpyrad ), naled (BRP), nicofluprole, nithiazine, nitenpyram, novaluron, noviflumuron, hydroprene, vaniliprole, vamidothion ), parathion, parathion-methyl, halfenprox, halofenozide, bistrifluron, bisultap, hydramethylnon, hydroxypropyl starch (hydroxy propyl starch), binapacryl, pyflubumide, bifenazate, bifenthrin, pymetrozine, pyraclorfos, pyrafluprole, pyridafenthion, pyridaben ( pyridaben), pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, pirimicarb, pyrimidifen, pyriminostrobin, pirimiphos-methy1, Pyrethrins, fipronil, fenazaquin, fenamiphos, bromopropylate, fenitrothion (MEP), fenoxycarb, fenothiocarb, phenothrin , fenobucarb, fensulfothion, fenthion (MPP), phenthoate (PAP), fenvalerate, fenpyroximate, fenpropathrin, fenbendazole ), fenmezoditiaz, fosthiazate, formetate, butathiofos, buprofezin, furathiocarb, prallethrin, fluacrypyrim, furazindo Lysine, fluazinam, fluazuron, fluensulfone, fluxametamide, fluchlordiniliprole, flucycloxuron, flucythrinate, fluvalinate, flupyradifurone, flufiprole, flupyradifurone, flupyrazofos, flupyrimin, flupyroxysrobin, flufenerim, flufenoxystrobin (flufenoxystrobin), flufenoxuron, flufenzine, flufenprox, fluproxyfen, flubrocythrinate, fluhexafon, flubendiamide, flupentiophenox, flumethrin, flurimfen, prothiofos, protrifenbute, flonicamid, propaphos, propargite (BPPS), profenofos (profenofos), broflanilide, profluthrin, propoxur (PHC), flometoquin, alpha-bromadiolone, bromopropylate, beta-cyfluthrin (beta- cyfluthrin), hexaflumuron, hexythiazox, heptafluthrin, heptenophos, permethrin, benclothiaz, bendiocarb, benzpyrimoxan, bensultap, benzoximate, benfuracarb, phoxim, phosalone, fosthiazate, fosthietan, phosphamidon, phosphocarb, phosmet : PMP), polynactins, formetanate, formothion, phorate, machine oil, malathion, milbemycin, milbemycin-A , milbemectin, mecarbam, mesulfenfos, methomyl, metaldehyde, metaflumizone, methamidophos, metam-ammonium, metam sodium ( metam-sodium), methiocarb, methidathion (DMTP), methylisothiocyanate, methylneodecanamide, methylparathion, metoxadiazone, methoxychlor, methoxyphenozide ( methoxyfenozide), metofluthrin, methoprene, metolcarb, meperfluthrin, mevinphos, monocrotophos, monosultap, momfluorothrin, lambda-cyhalothrin ( lambda-cyhalothrin), ryanodine, lufenuron, rescalure, resmethrin, lepimectin, rotenone, levamisol hydrochloride, fenbutatin oxide, tartaric acid Morantel tartarate, methyl bromide, cyhexatin hydroxide, calcium cyanamide, calcium polysulfide, sulfur, and nicotine sulfate. sulfate), etc.
同様の目的で使用する農園芸用殺菌剤として例えば、アウレオフンギン(aureofungin)、アザコナゾール(azaconazole)、アジチラム(azithiram)、アシペタックス(acypetacs)、アシベンゾラル(acibenzolar)、アシベンゾラルSメチル(acibenzolar-S-methyl)、アゾキシストロビン(azoxystrobin)、アニラジン(anilazine)、アミスルブロム(amisulbrom)、アムプロピルホス(ampropylfos)、アメトクトラジン(ametoctradin)、アリルアルコール(allyl alcohol)、アルジモルフ(aldimorph)、アンバム(amobam)、イソチアニル(isotianil)、イソバレジオン(isovaledione)、イソピラザム(isopyrazam)、イソフェタミド(isofetamid)、イソフルシプラム(isoflucypram)、イソプロチオラン(isoprothiolane)、イプコナゾール(ipconazole)、イプフェントリフルコナゾール(ipfentrifluconazole)、イプフルフェノキン(ipflufenoquin)、イプロジオン(iprodione)、イプロバリカルブ(iprovalicarb)、イプロベンホス(iprobenfos)、イマザリル(imazalil)、イミノクタジン(iminoctadine)、メタム(metam)、イミノクタジンアルベシル酸塩(iminoctadine-albesilate)、イミノクタジン酢酸塩(iminoctadine-triacetate)、イミベンコナゾール(imibenconazole)、インピルフルキサム(inpyrfluxam)、ウニコナゾール(uniconazole)、ウニコナゾール-P(uniconazole-P)、エクロメゾール(echlomezole)、エジフェンホス(edifenphos)、エタコナゾール(etaconazole)、エタボキサム(ethaboxam)、エチリモール(ethirimol)、エテム(etem)、エトキシキン(ethoxyquin)、エトリジアゾール(etridiazole)、エネストロブリン(enestroburin)、エノキサストロビン(enoxastrobin)、エポキシコナゾール(epoxiconazole)、オキサジキシル(oxadixyl)、オキサチアピプロリン(oxathiapiprolin)、オキシカルボキシン(oxycarboxin)、オキシキノリン銅(copper-8-quinolinolate)、オキシテトラサイクリン(oxytetracycline)、オキシン銅(copper-oxinate)、オキスポコナゾール(oxpoconazole)、オキスポコナゾールフマル酸塩(oxpoconazole-fumarate)、オキソリニック酸(oxolinic acid)、オクチリノン(octhilinone)、オフラセ(ofurace)、オリサストロビン(orysastrobin)、カーバム(carbam、metam-sodium)、カスガマイシン(kasugamycin)、カルバモルフ(carbamorph)、カルプロパミド(carpropamid)、カルベンダジム(carbendazim)、カルボキシン(carboxin)、カルボン(carvone)、キナザミド(quinazamid)、キナセトール(quinacetol)、キノキシフェン(quinoxyfen)、キノフメリン(quinofumelin)、キノメチオネート(chinomethionat 、quinomethionate)、キャプタホール(captafol)、キャプタン(captan)、キララキシル(kiralaxyl)、キンコナゾール(quinconazole)、キントゼン(quintozene)、グアザチン(guazatine)、クフラネブ(cufraneb)、クプロバム(cuprobam)、クモキシストロビン(coumoxystrobin)、グリオジン(glyodin)、グリセオフルビン(griseofulvin)、クリムバゾール(climbazole)、クレゾール(cresol)、クレソキシム-メチル(kresoxim-methyl)、クロゾリネート(chlozolinate)、クロトリマゾール(clotrimazole)、クロベンチアゾン(chlobenthiazone)、クロラニホルメタン(chloraniformethan)、クロラニル(chloranil)、クロルキノックス(chlorquinox)、クロルピクリン(chloropicrin)、クロルフェナゾール(chlorfenazole)、クロロインコナジド(chloroinconazide)、クロロジニトロナフタレン(chlorodinitronaphthalene)、クロロタロニル(chlorothalonil)、クロロネブ(chloroneb)、サリチルアニリド(salicylanilide)、ザリラミド(zarilamid)、シアゾファミド(cyazofamid)、ジエチルピロカーボナート(diethyl pyrocarbonate)、ジエトフェンカルブ(diethofencarb)、シクラフラミド(cyclafuramid)、ジクロシメット(diclocymet)、ジクロゾリン(dichlozoline)、ジクロブトラゾール(diclobutrazol)、シクロブトリフルラム(cyclobutrifluram)、ジクロフルアニド(dichlofluanid)、シクロヘキシミド(cycloheximide)、ジクロベンチアゾクス(dichlobentiazox)、ジクロメジン(diclomezine)、ジクロラン(dicloran)、ジクロロフェン(dichlorophen)、ジクロン(dichlone)、ジスルフィラム(disulfiram)、ジタリムフォス(ditalimfos)、ジチアノン(dithianon)、ジニコナゾール(diniconazole)、ジニコナゾール-M(diniconazole-M)、ジネブ(zineb)、ジノカップ(dinocap)、ジノクトン(dinocton)、ジノスルホン(dinosulfon)、ジノテルボン(dinoterbon)、ジノブトン(dinobuton)、ジノペントン(dinopenton)、ジピメチトロン(dipymetitrone)、ジピリチオン(dipyrithione)、ジフェニルアミン(diphenylamine)、ジフェノコナゾール(difenoconazole)、シフルフェナミド(cyflufenamid)、ジフルメトリム(diflumetorim)、シプロコナゾール(cyproconazole)、シプロジニル(cyprodinil)、シプロフラム(cyprofuram)、シペンダゾール(cypendazole)、シメコナゾール(simeconazole)、ジメチリモール(dimethirimol)、ジメトモルフ(dimethomorph)、シモキサニル(cymoxanil)、ジモキシストロビン(dimoxystrobin)、ジラム(ziram)、シルチオファム(silthiofam)、ストレプトマイシン(streptomycin)、スピロキサミン(spiroxamine)、スルトロペン(sultropen)、セダキサン(sedaxane)、ゾキサミド(zoxamide)、ダゾメット(dazomet)、チアジアジン(thiadiazin)、チアジニル(tiadinil)、チアジフルオル(thiadifluor)、チアベンダゾール(thiabendazole)、チオキシミド(tioxymid)、チオクロルフェンフィム(thiochlorfenphim)、チオファネート(thiophanate)、チオファネート-メチル(thiophanate-methyl)、チフルザミド(thifluzamide)、チシオフェン(thicyofen)、チオキノックス(thioquinox)、チラム(thiram)、デカフェンチン(decafentin)、テクナゼン(tecnazene)、テクロフタラム(tecloftalam)、テコラム(tecoram)、テトラコナゾール(tetraconazole)、デバカルブ(debacarb)、デヒドロ酢酸(dehydroacetic acid)、テブコナゾール(tebuconazole)、テブフロキン(tebufloquin)、ドジシン(dodicin)、ドジン(dodine)、ドデシルベンゼンスルホン酸ビスエチレンジアミン銅錯塩(II)(DBEDC)、ドデモルフ(dodemorph)、ドラゾキソロン(drazoxolon)、トリアジメノール(triadimenol)、トリアジメホン(triadimefon)、トリアズブチル(triazbutil)、トリアゾキシド(triazoxide)、トリアミホス(triamiphos)、トリアリモール(triarimol)、トリクラミド(trichlamide)、トリクロピリカルブ(triclopyricarb)、トリシクラゾール(tricyclazole)、トリチコナゾール(triticonazole)、トリデモルフ(tridemorph)、トリブチルチンオキシド(tributyltin oxide)、トリフルミゾール(triflumizole)、トリフロキシストロビン(trifloxystrobin)、トリホリン(triforine)、トリルフルアニド(tolylfluanid)、トルクロホスメチル(tolclofos-methyl)、トルプロカルブ(tolprocarb)、ナタマイシン(natamycin)、ナバム(nabam)、ニトロスチレン(nitrostyrene)、ニトロタールイソプロピル(nitrothal-isopropyl)、ヌアリモール(nuarimol)、ノニルフェノールスルホン酸銅(copper nonylphenol sulfonate)、ハラクリネート(halacrinate)、バリダマイシン(validamycin)、バリフェナラート(valifenalate)、ハルピンタンパク(harpin protein)、ピカルブトラゾクス(picarbutrazox)、ビキサフェン(bixafen)、ピコキシストロビン(picoxystrobin)、ピコベンザミド(picobenzamide)、ピジフルメトフェン(pydiflumetofen)、ビチオノール(bithionol)、ビテルタノール(bitertanol)、ヒドロキシイソキサゾール(hydroxyisoxazole)、ヒドロキシイソキサゾール-カリウム(hydroisoxazole-potassium)、ビナパクリル(binapacryl)、ビフェニル(biphenyl)、ピペラリン(piperalin)、ヒメキサゾール(hymexazol)、ピラオキシストロビン(pyraoxystrobin)、ピラカルボリド(pyracarbolid)、ピラクロストロビン(pyraclostrobin)、ピラジフルミド(pyraziflumid)、ピラゾホス(pyrazophos)、ピラプロポイン(pyrapropoyne)、ピラメトストロビン(pyrametostrobin)、ピリオフェノン(pyriofenone)、ピリジニトリル(pyridinitril)、ピリジフルメトフェン(pydiflumetofen)、ピリソキサゾール(pyrisoxazole)、ピリダクロメチル(pyridachlometyl)、ピリフェノックス(pyrifenox)、ピリベンカルブ(pyribencarb)、ピリミノストロビン(pyriminostrobin)、ピリメタニル(pyrimethanil)、ピロキシクロル(pyroxychlor)、ピロキシフル(pyroxyfur)、ピロキロン(pyroquilon)、ビンクロゾリン(vinclozolin)、ファーバム(ferbam)、ファモキサドン(famoxadone)、フェナパニル(fenapanil)、フェナミドン(fenamidone)、フェナミノスルフ(fenaminosulf)、フェナミンストロビン(fenaminstrobin)、フェナリモール(fenarimol)、フェニトロパン(fenitropan)、フェノキサニル(fenoxanil)、フェリムゾン(ferimzone)、フェルバム(ferbam)、フェンチン(fentin)、フェンピクロニル(fenpiclonil)、フェンピコキサミド(fenpicoxamid)、フェンピラザミン(fenpyrazamine)、フェンブコナゾール(fenbuconazole)、フェンフラム(fenfuram)、フェンプロピジン(fenpropidin)、フェンプロピモルフ(fenpropimorph)、フェンヘキサミド(fenhexamid)、フタリド(phthalide)、ブチオベート(buthiobate)、ブチルアミン(butylamine)、ブピリメート(bupirimate)、フベリダゾール(fuberidazole)、ブラストサイジンS(blasticidin-S)、フラメトピル(furametpyr)、フララキシル(furalaxyl)、フルアクリピリム(fluacrypyrim)、フルアジナム(fluazinam)、フルインダピル(fluindapyr)、フルオキサストロビン(fluoxastrobin)、フルオキサピプロリン(fluoxapiprolin)、フルオキシチオコナゾール(fluoxytioconazole)、フルオトリマゾール(fluotrimazole)、フルオピコリド(fluopicolide)、フルオピモミド(Fluopimomide)、フルオピラム(fluopyram)、フルオロイミド(fluoroimide)、フルカルバニル(furcarbanil)、フルキサピロキサド(fluxapyroxad)、フルキンコナゾール(fluquinconazole)、フルコナゾール(furconazole)、フルコナゾール-シス(furconazole-cis)、フルジオキソニル(fludioxonil)、フルシラゾール(flusilazole)、フルスルファミド(flusulfamide)、フルチアニル(flutianil)、フルトラニル(flutolanil)、フルトリアホール(flutriafol)、フルフェノキサジアザム(flufenoxadiazam)、フルフェノキシストロビン(flufenoxystrobin)、フルフラール(furfural)、フルベネテラム(flubeneteram)、フルメシクロックス(furmecyclox)、フルメチルスルフォリム(flumetylsulforim)、フルメットベル(flumetover)、フルモルフ(flumorph)、プロキナジド(proquinazid)、プロクロラズ(prochloraz)、プロシミドン(procymidone)、プロチオカルブ(prothiocarb)、プロチオコナゾール(prothioconazole)、プロニトリジン(pronitridine)、プロパモカルブ(propamocarb)、プロピコナゾール(propiconazole)、プロピネブ(propineb)、フロファネート(furophanate)、プロベナゾール(probenazole)、ブロムコナゾール(bromuconazole)、フロリルピコキサミド(florylpicoxamid)、ヘキサクロロブタジエン(hexachlorobutadiene)、ヘキサコナゾール(hexaconazole)、ヘキシルチオホス(hexylthiofos)、ベトキサジン(bethoxazin)、ベナラキシル(benalaxyl)、ベナラキシル-M(benalaxyl-M)、ベノダニル(benodanil)、ベノミル(benomyl)、ペフラゾエート(pefurazoate)、ベンキノックス(benquinox)、ペンコナゾール(penconazole)、ベンザモルフ(benzamorf)、ペンシクロン(pencycuron)、ベンゾヒドロキサム酸(benzohydroxamic acid)、ベンゾビンジフルピル(b
enzovindiflupyr)、ベンタルロン(bentaluron)、ベンチアゾール(benthiazole)、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)、ペンチオピラド(penthiopyrad)、ペンフルフェン(penflufen)、ボスカリド(boscalid)、ホスジフェン(phosdiphen)、ホセチル(fosetyl)、ホセチル-アルミニウム(fosetyl‐Al)、ポリオキシン(polyoxins)、ポリオキソリン(polyoxorim)、ポリカーバメート(polycarbamate)、ホルペット(folpet)、ホルムアルデヒド(formaldehyde)、マシン油(machine oil)、マネブ(maneb)、マンコゼブ(mancozeb)、マンジプロパミド(mandipropamid)、マンデストロビン(mandestrobin)、ミクロゾリン(myclozolin)、ミクロブタニル(myclobutanil)、ミルディオマイシン(mildiomycin)、ミルネブ(milneb)、メカルビンジド(mecarbinzid)、メタスルホカルブ(methasulfocarb)、メタゾキソロン(metazoxolon)、メタム(metam)、メタムナトリウム塩(metam‐sodium)、メタラキシル(metalaxyl)、メタラキシル-M(metalaxyl-M)、メタリルピコキサミド(metarylpicoxamid)、メチラム(metiram)、メチルイソチオシアナート(methyl isothiocyanate)、メチルジノカップ(mepthyldinocap)、メチルテトラプロール(Metyltetraprole)、メトコナゾール(metconazole)、メトスルホバックス(metsulfovax)、メトフロキサム(methfuroxam)、メトミノストロビン(metominostrobin)、メトラフェノン(metrafenone)、メパニピリム(mepanipyrim)、メフェノキサム(mefenoxam)、メフェントリフルコナゾール(mefentrifluconazole)、メプチルジノカップ(meptyldinocap)、メプロニル(mepronil)、メベニル(mebenil)、ヨウ化メチル(iodomethane)、ラベンザゾール(rabenzazole)、臭化メチル(methyl bromide)、塩化ベンザルコニウム(benzalkonium chloride)、塩基性塩化銅(basic copper chloride)、塩基性硫酸銅(basic copper sulfate)、金属銀(silver)などの無機殺菌剤、次亜塩素酸ナトリウム(sodium hypochlorote)、水酸化第二銅(cupric hydroxide)、水和硫黄剤(wettable sulfur)、石灰硫黄合剤(calcium polysulfide)、炭酸水素カリウム(potassium hydrogen carbonate)、炭酸水素ナトリウム(sodium hydrogen carbonate)、無機硫黄(sulfur)、無水硫酸銅(copper sulfate anhydride)、ジメチルジチオカルバミド酸ニッケル(nickel dimethyldithiocarbamate)、8-ヒドロキシキノリン銅(oxine copper)のような銅系化合物、硫酸亜鉛(zinc sulfate)、硫酸銅五水塩(copper sulfate pentahydrate)等を例示することができる。 Examples of agricultural and horticultural fungicides used for similar purposes include aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, and acibenzolar-S-methyl. ), azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isotianil isotianil, isovaledione, isopyrazam, isofetamid, isoflucypram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin ), iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-albesilate, iminoctadine-triacetate ), imibenconazole, inpyrfluxam, uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole, ethaboxam , ethirimol, etem, ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxiconazole, oxadixyl, oxathiapi Proline (oxathiapiprolin), oxycarboxin (oxycarboxin), oxyquinoline copper (copper-8-quinolinolate), oxytetracycline (oxytetracycline), oxine copper (copper-oxinate), oxpoconazole, oxpoconazole fumar Oxpoconazole-fumarate, oxolinic acid, octhilinone, ofurace, orysastrobin, carbam, metam-sodium, kasugamycin, carbamorph, carpropamide (carpropamid), carbendazim, carboxin, carvone, quinazamid, quinacetol, quinoxyfen, quinofumelin, chinomethionat, quinomethionate, capta captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine, cufraneb, cuprobam, coumoxystrobin, gliozin (glyodin), griseofulvin, climbazole, cresol, kresoxim-methyl, chlozolinate, clotrimazole, clobenthiazone, chloraniform chloraniformethan, chloranil, chlorquinox, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, chloroneb ( chloroneb), salicylanilide, zarilamid, cyazofamid, diethyl pyrocarbonate, diethofencarb, cyclafuramid, diclocymet, dichlozoline, diclob Torazol, cyclobutrifluram, dichlofluanid, cycloheximide, dichlobentiazox, diclomezine, dicloran, dichlorophen, dichlone, disulfiram, ditalimfos, dithianon, diniconazole, diniconazole-M, zineb, dinocap, dinocton, dinosulfone (dinosulfon), dinoterbon, dinobuton, dinopenton, dipymethitrone, dipyrithione, diphenylamine, difenoconazole, cyflufenamide, diflumetorim, cyproconazole, cyprodinil, cyprofuram, cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, diram (ziram), silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazin, tiadinil, thiadifluor (thiadifluor), thiabendazole, thioxymid, thiochlorfenphim, thiophanate, thiophanate-methyl, thifluzamide, thicyofen, thioquinox , thiram, decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid, tebuconazole , tebufloquin, dodicin, dodine, dodecylbenzenesulfonic acid bisethylenediamine copper complex (II) (DBEDC), dodemorph, drazoxolon, triadimenol, triadimefon ( triadimefon), triazbutil, triazoxide, triamiphos, triarimol, trichlamide, triclopyricarb, tricyclazole, triticonazole, tridemorph (tridemorph), tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb ), natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin ), valifenalate, harpin protein, picarbutrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroisoxazole-potassium, binapacryl, biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyraziflumid, pyrazophos, pyrapropoyne, pyrametostrobin, pyriofenone, pyridinitril ), pydiflumetofen, pyrisoxazole, pyridachlomethyl, pyrifenox, pyribencarb, pyriminostrobin, pyrimethanil, pyroxychlor ), pyroxyfur, pyroquilon, vinclozolin, ferbam, famoxadone, fenapanil, fenamidone, fenaminosulf, fenaminstrobin, fenarimol (fenarimol), fenitropan, fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpicoxamid, fenpyrazamine, fenbuco fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate , fuberidazole, blasticidin-S, furametpyr, furalaxyl, fluacrypyrim, fluazinam, fluindapyr, fluoxastrobin, flu oxapiprolin, fluoxytioconazole, fluotrimazole, fluopicolide, fluopimomide, fluopyram, fluoroimide, furcarbanil, flu fluxapyroxad, fluquinconazole, fluconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil ( flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, furfural, flubeneteram, furmecyclox, flumetylsulforim ), flumetover, flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole, pronitridine, propamocarb, propiconazole, propineb, furophanate, probenazole, bromuconazole, florylpicoxamid, hexachlorobutadiene, hexaconazole , hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox, penconazole , benzamorf, pencycuron, benzohydroxamic acid, benzobine diflupyr (b
enzovindiflupyr), bentaluron, benthiazole, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, fosdifen (phosdiphen), fosetyl, fosetyl-Al, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil ), maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid , methasulfocarb, metazoxolon, metam, metam-sodium, metalaxyl, metalaxyl-M, metarylpicoxamide , metiram, methyl isothiocyanate, mepthyldinocap, methyltetraprole, metconazole, metsulfovax, methfuroxam, metominostrobin ( metominostrobin, metrafenone, mepanipyrim, mefenoxam, mefentrifluconazole, meptyldinocap, mepronil, mebenil, iodomethane , rabenzazole, methyl bromide, benzalkonium chloride, basic copper chloride, basic copper sulfate, metallic silver, etc. Inorganic disinfectants, sodium hypochlorote, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate copper-based compounds such as sodium hydrogen carbonate, inorganic sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, and oxine copper. , zinc sulfate, copper sulfate pentahydrate, and the like.
enzovindiflupyr)、ベンタルロン(bentaluron)、ベンチアゾール(benthiazole)、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)、ペンチオピラド(penthiopyrad)、ペンフルフェン(penflufen)、ボスカリド(boscalid)、ホスジフェン(phosdiphen)、ホセチル(fosetyl)、ホセチル-アルミニウム(fosetyl‐Al)、ポリオキシン(polyoxins)、ポリオキソリン(polyoxorim)、ポリカーバメート(polycarbamate)、ホルペット(folpet)、ホルムアルデヒド(formaldehyde)、マシン油(machine oil)、マネブ(maneb)、マンコゼブ(mancozeb)、マンジプロパミド(mandipropamid)、マンデストロビン(mandestrobin)、ミクロゾリン(myclozolin)、ミクロブタニル(myclobutanil)、ミルディオマイシン(mildiomycin)、ミルネブ(milneb)、メカルビンジド(mecarbinzid)、メタスルホカルブ(methasulfocarb)、メタゾキソロン(metazoxolon)、メタム(metam)、メタムナトリウム塩(metam‐sodium)、メタラキシル(metalaxyl)、メタラキシル-M(metalaxyl-M)、メタリルピコキサミド(metarylpicoxamid)、メチラム(metiram)、メチルイソチオシアナート(methyl isothiocyanate)、メチルジノカップ(mepthyldinocap)、メチルテトラプロール(Metyltetraprole)、メトコナゾール(metconazole)、メトスルホバックス(metsulfovax)、メトフロキサム(methfuroxam)、メトミノストロビン(metominostrobin)、メトラフェノン(metrafenone)、メパニピリム(mepanipyrim)、メフェノキサム(mefenoxam)、メフェントリフルコナゾール(mefentrifluconazole)、メプチルジノカップ(meptyldinocap)、メプロニル(mepronil)、メベニル(mebenil)、ヨウ化メチル(iodomethane)、ラベンザゾール(rabenzazole)、臭化メチル(methyl bromide)、塩化ベンザルコニウム(benzalkonium chloride)、塩基性塩化銅(basic copper chloride)、塩基性硫酸銅(basic copper sulfate)、金属銀(silver)などの無機殺菌剤、次亜塩素酸ナトリウム(sodium hypochlorote)、水酸化第二銅(cupric hydroxide)、水和硫黄剤(wettable sulfur)、石灰硫黄合剤(calcium polysulfide)、炭酸水素カリウム(potassium hydrogen carbonate)、炭酸水素ナトリウム(sodium hydrogen carbonate)、無機硫黄(sulfur)、無水硫酸銅(copper sulfate anhydride)、ジメチルジチオカルバミド酸ニッケル(nickel dimethyldithiocarbamate)、8-ヒドロキシキノリン銅(oxine copper)のような銅系化合物、硫酸亜鉛(zinc sulfate)、硫酸銅五水塩(copper sulfate pentahydrate)等を例示することができる。 Examples of agricultural and horticultural fungicides used for similar purposes include aureofungin, azaconazole, azithiram, acypetacs, acibenzolar, and acibenzolar-S-methyl. ), azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isotianil isotianil, isovaledione, isopyrazam, isofetamid, isoflucypram, isoprothiolane, ipconazole, ipfentrifluconazole, ipflufenoquin ), iprodione, iprovalicarb, iprobenfos, imazalil, iminoctadine, metam, iminoctadine-albesilate, iminoctadine-triacetate ), imibenconazole, inpyrfluxam, uniconazole, uniconazole-P, echlomezole, edifenphos, etaconazole, ethaboxam , ethirimol, etem, ethoxyquin, etridiazole, enestroburin, enoxastrobin, epoxiconazole, oxadixyl, oxathiapi Proline (oxathiapiprolin), oxycarboxin (oxycarboxin), oxyquinoline copper (copper-8-quinolinolate), oxytetracycline (oxytetracycline), oxine copper (copper-oxinate), oxpoconazole, oxpoconazole fumar Oxpoconazole-fumarate, oxolinic acid, octhilinone, ofurace, orysastrobin, carbam, metam-sodium, kasugamycin, carbamorph, carpropamide (carpropamid), carbendazim, carboxin, carvone, quinazamid, quinacetol, quinoxyfen, quinofumelin, chinomethionat, quinomethionate, capta captafol, captan, kiralaxyl, quinconazole, quintozene, guazatine, cufraneb, cuprobam, coumoxystrobin, gliozin (glyodin), griseofulvin, climbazole, cresol, kresoxim-methyl, chlozolinate, clotrimazole, clobenthiazone, chloraniform chloraniformethan, chloranil, chlorquinox, chloropicrin, chlorfenazole, chloroinconazide, chlorodinitronaphthalene, chlorothalonil, chloroneb ( chloroneb), salicylanilide, zarilamid, cyazofamid, diethyl pyrocarbonate, diethofencarb, cyclafuramid, diclocymet, dichlozoline, diclob Torazol, cyclobutrifluram, dichlofluanid, cycloheximide, dichlobentiazox, diclomezine, dicloran, dichlorophen, dichlone, disulfiram, ditalimfos, dithianon, diniconazole, diniconazole-M, zineb, dinocap, dinocton, dinosulfone (dinosulfon), dinoterbon, dinobuton, dinopenton, dipymethitrone, dipyrithione, diphenylamine, difenoconazole, cyflufenamide, diflumetorim, cyproconazole, cyprodinil, cyprofuram, cypendazole, simeconazole, dimethirimol, dimethomorph, cymoxanil, dimoxystrobin, diram (ziram), silthiofam, streptomycin, spiroxamine, sultropen, sedaxane, zoxamide, dazomet, thiadiazin, tiadinil, thiadifluor (thiadifluor), thiabendazole, thioxymid, thiochlorfenphim, thiophanate, thiophanate-methyl, thifluzamide, thicyofen, thioquinox , thiram, decafentin, tecnazene, tecloftalam, tecoram, tetraconazole, debacarb, dehydroacetic acid, tebuconazole , tebufloquin, dodicin, dodine, dodecylbenzenesulfonic acid bisethylenediamine copper complex (II) (DBEDC), dodemorph, drazoxolon, triadimenol, triadimefon ( triadimefon), triazbutil, triazoxide, triamiphos, triarimol, trichlamide, triclopyricarb, tricyclazole, triticonazole, tridemorph (tridemorph), tributyltin oxide, triflumizole, trifloxystrobin, triforine, tolylfluanid, tolclofos-methyl, tolprocarb ), natamycin, nabam, nitrostyrene, nitrothal-isopropyl, nuarimol, copper nonylphenol sulfonate, halacrinate, validamycin ), valifenalate, harpin protein, picarbutrazox, bixafen, picoxystrobin, picobenzamide, pydiflumetofen, bithionol, bitertanol, hydroxyisoxazole, hydroisoxazole-potassium, binapacryl, biphenyl, piperalin, hymexazol, pyraoxystrobin, pyracarbolid, pyraclostrobin, pyraziflumid, pyrazophos, pyrapropoyne, pyrametostrobin, pyriofenone, pyridinitril ), pydiflumetofen, pyrisoxazole, pyridachlomethyl, pyrifenox, pyribencarb, pyriminostrobin, pyrimethanil, pyroxychlor ), pyroxyfur, pyroquilon, vinclozolin, ferbam, famoxadone, fenapanil, fenamidone, fenaminosulf, fenaminstrobin, fenarimol (fenarimol), fenitropan, fenoxanil, ferimzone, ferbam, fentin, fenpiclonil, fenpicoxamid, fenpyrazamine, fenbuco fenbuconazole, fenfuram, fenpropidin, fenpropimorph, fenhexamid, phthalide, buthiobate, butylamine, bupirimate , fuberidazole, blasticidin-S, furametpyr, furalaxyl, fluacrypyrim, fluazinam, fluindapyr, fluoxastrobin, flu oxapiprolin, fluoxytioconazole, fluotrimazole, fluopicolide, fluopimomide, fluopyram, fluoroimide, furcarbanil, flu fluxapyroxad, fluquinconazole, fluconazole, furconazole-cis, fludioxonil, flusilazole, flusulfamide, flutianil, flutolanil ( flutolanil, flutriafol, flufenoxadiazam, flufenoxystrobin, furfural, flubeneteram, furmecyclox, flumetylsulforim ), flumetover, flumorph, proquinazid, prochloraz, procymidone, prothiocarb, prothioconazole, pronitridine, propamocarb, propiconazole, propineb, furophanate, probenazole, bromuconazole, florylpicoxamid, hexachlorobutadiene, hexaconazole , hexylthiofos, bethoxazin, benalaxyl, benalaxyl-M, benodanil, benomyl, pefurazoate, benquinox, penconazole , benzamorf, pencycuron, benzohydroxamic acid, benzobine diflupyr (b
enzovindiflupyr), bentaluron, benthiazole, benthiavalicarb, benthiavalicarb-isopropyl, penthiopyrad, penflufen, boscalid, fosdifen (phosdiphen), fosetyl, fosetyl-Al, polyoxins, polyoxorim, polycarbamate, folpet, formaldehyde, machine oil ), maneb, mancozeb, mandipropamid, mandestrobin, myclozolin, myclobutanil, mildiomycin, milneb, mecarbinzid , methasulfocarb, metazoxolon, metam, metam-sodium, metalaxyl, metalaxyl-M, metarylpicoxamide , metiram, methyl isothiocyanate, mepthyldinocap, methyltetraprole, metconazole, metsulfovax, methfuroxam, metominostrobin ( metominostrobin, metrafenone, mepanipyrim, mefenoxam, mefentrifluconazole, meptyldinocap, mepronil, mebenil, iodomethane , rabenzazole, methyl bromide, benzalkonium chloride, basic copper chloride, basic copper sulfate, metallic silver, etc. Inorganic disinfectants, sodium hypochlorote, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate copper-based compounds such as sodium hydrogen carbonate, inorganic sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, and oxine copper. , zinc sulfate, copper sulfate pentahydrate, and the like.
同様に除草剤として例えば、1-ナフチルアセトアミド、2,4-PA、2,3,6-TBA、2,4,5-T、2,4,5-TB、2,4-D、2,4-DB、2,4-DEB、2,4-DEP、3,4-DA、3,4-DB、3,4-DP、4-CPA、4-CPB、4-CPP、MCP、MCPA、MCPAチオエチル、MCPB、アイオキシニル(ioxynil)、アイカフォリン(icafolin)、アイカフォリン‐メチル(icafolin-methyl)、アクロニフェン(aclonifen)、アザフェニジン(azafenidin)、アシフルオルフェン(acifluorfen)、アジプロトリン(aziprotryne)、アジムスルフロン(azimsulfuron)、アシュラム(asulam)、アセトクロール(acetochlor)、アトラジン(atrazine)、アトラトン(atraton)、アニスロン(anisuron)、アニロホス(anilofos)、アビグリシン(aviglycine)、アブシジン酸(abscisic acid)、アミカルバゾン(amicarbazone)、アミドスルフロン(amidosulfuron)、アミトロール(amitrole)、アミノシクロピラクロール(aminocyclopyrachlor)、アミノピラリド(aminopyralid)、アミブジン(amibuzin)、アミプロホスメチル(amiprophos-methyl)、アメトリジオン(ametridione)、アメトリン(ametryn)、アラクロール(alachlor)、アリドクロール(allidochlor)、アロキシジム(alloxydim)、アロラック(alorac)、イオフェンスルフロン(iofensulfuron)、イソウロン(isouron)、イソカルバミド(isocarbamid)、イソキサクロルトール(isoxachlortole)、イソキサピリホップ(isoxapyrifop)、イソキサフルトール(isoxaflutole)、イソキサベン(isoxaben)、イソシル(isocil)、イソノルロン(isonoruron)、イソプロツロン(isoproturon)、イソプロパリン(isopropalin)、イソポリナート(isopolinate)、イソメチオジン(isomethiozin)、イナベンフィド(inabenfide)、イパジン(ipazine)、イプトリアゾピリド(iptriazopyrid)、イプフェンカルバゾン(ipfencarbazone)、イプリミダム(iprymidam)、イマザキン(imazaquin)、イマザピック(imazapic)、イマザピル(imazapyr)、イマザメタピル(imazamethapyr)、イマザメタベンズ(imazamethabenz)、イマザメタベンズ-メチル(imazamethabenz-methyl)、イマザモックス(imazamox)、イマゼタピル(imazethapyr)、イマゾスルフロン(imazosulfuron)、インダジフラム(indaziflam)、インダノファン(indanofan)、インドラウキシピル(indolauxipyr)、インドラウキシピル‐シアノメチル(indolauxipyr-syanomethyl)、インドール酪酸(indolebutyric acid)、ウニコナゾール-P(uniconazole-P)、エグリナジン(eglinazine)、エスプロカルブ(esprocarb)、エタメスルフロン(ethametsulfuron)、エタメトスルフロン-メチル(ethametsulfuron-methyl)、エタルフルラリン(ethalfluralin)、エチオレート(ethiolate)、エチクロゼート-エチル(ethychlozate-ethyl)、エチジムロン(ethidimuron)、エチノフェン(etinofen)、エテホン(ethephon)、エトキシスルフロン(ethoxysulfuron)、エトキシフェン(ethoxyfen)、エトニプロミド(etnipromid)、エトフメセート(ethofumesate)、エトベンザニド(etobenzanid)、エピリフェナシル(epyrifenacil)、エプロナズ(epronaz)、エルボン(erbon)、エンドタール(endothal)、オキサジアゾン(oxadiazon)、オキサジアルギル(oxadiargyl)、オキサジクロメホン(oxaziclomefone)、オキサスルフロン(oxasulfuron)、オキサピラゾン(oxapyrazon)、オキシフルオルフェン(oxyfluorfen)、オリザリン(oryzalin)、オルソスルファムロン(orthosulfamuron)、オルベンカルブ(orbencarb)、カフェンストロール(cafenstrole)、カムベンジクロール(cambendichlor)、カルバスラム(carbasulam)、カルフェントラゾン(carfentrazone)、カルフェントラゾン-エチル(carfentrazone-ethyl)、カルブチレート(karbutilate)、カルベタミド(carbetamide)、カルボキサゾール(carboxazole)、キザロホップ(quizalofop)、キザロホップ-P(quizalofop-P)、キザロホップ-エチル(quizalofop-ethyl)、キシラクロール(xylachlor)、キノクラミン(quinoclamine)、キノナミド(quinonamid)、キンクロラック(quinclorac)、キンメラック(quinmerac)、クミルロン(cumyluron)、クラシホス(clacyfos)、クリオジネート(cliodinate)、グリホサート(glyphosate)、グルホシネート(glufosinate)、グルホシネート-P(glufosinate-P)、クレダジン(credazine)、クレトジム(clethodim)、クロキシホナック(cloxyfonac)、クロジナホップ(clodinafop)、クロジナホップ-プロパルギル(clodinafop-propargyl)、クロトルロン(chlorotoluron)、クロピラリド(clopyralid)、クロプロキシジム(cloproxydim)、クロプロップ(cloprop)、クロブロムロン(chlorbromuron)、クロホップ(clofop)、クロマゾン(clomazone)、クロメトキシニル(chlomethoxyni1)、クロメトキシフェン(chlomethoxyfen)、クロメプロップ(clomeprop)、クロラジホップ(chlorazifop)、クロラジン(chlorazine)、クロラノクリル(chloranocryl)、クロラムベン(chloramben)、クロランスラム(cloransulam)、クロランスラム-メチル(cloransulam-methyl)、クロリダゾン(chloridazon)、クロリムロン(chlorimuron)、クロリムロン-エチル(chlorimuron-ethyl)、クロルスルフロン(chlorsulfuron)、クロルタール(chlorthal)、クロルチアミド(chlorthiamid)、クロルトルロン(chlortoluron)、クロルニトロフェン(chlornitrofen)、クロルフェナック(chlorfenac)、クロルフェンプロップ(chlorfenprop)、クロルブファム(chlorbufam)、クロルフタリム(chlorphthalim)、クロルフルラゾール(chlorflurazole)、クロルフルレノール(chlorflurenol)、クロルプロカルブ(chlorprocarb)、クロルプロファム(chlorpropham)、クロルメコート(chlormequat)、クロレツロン(chloreturon)、クロロキシニル(chloroxynil)、クロロクスロン(chloroxuron)、クロロトルロン(chlorotoluron)、クロロポン(chloropon)、サフルフェナシル(saflufenacil)、シアナジン(cyanazine)、シアナトリン(cyanatryn)、ジアレート(di-allate)、ジウロン(diuron)、ジエタムコート(diethamquat)、ジオキソピリトリオン(dioxopyritrione)、ジカンバ(dicamba)、シクルロン(cycluron)、シクロエート(cycloate)、シクロキシジム(cycloxydim)、ジクロスラム(diclosulam)、シクロスルファムロン(cyclosulfamuron)、シクロピラニル(cyclopyranil) 、シクロピリモレート(cyclopyrimorate)、ジクロプロップ(dichlorprop)、ジクロプロップ-P(dichlorprop-P)、ジクロベニル(dichlobenil)、ジクロホップ(diclofop)、ジクロホップ-メチル(diclofop-methyl)、ジクロメート(dichlormate)、ジクロラルウレア(dichloralurea)、ジクワット(diquat)、シサニリド(cisanilide)、ジスル(disul)、シズロン(siduron)、ジチオピル(dithiopyr)、ジニトラミン(dinitramine)、シニドンエチル(cinidon-ethyl)、ジノサム(dinosam)、シノスルフロン(cinosulfuron)、ジノセブ(dinoseb)、ジノテルブ(dinoterb)、ジノフェナート(dinofenate)、ジノプロップ(dinoprop)、シハロホップブチル(cyhalofop-butyl)、シピラフルオン(cypyrafluone)、ジフェナミド(diphenamid)、ジフェノクスロン(difenoxuron)、ジフェノペンテン(difenopenten)、ジフェンゾコート(difenzoquat)、シブトリン(cybutryne)、シプラジン(cyprazine)、シプラゾール(cyprazole)、ジフルフェニカン(diflufenican)、ジフルフェンゾピル(diflufenzopyr)、ジプロペトリン(dipropetryn)、シプロミド(cypromid)、シペルコート(cyperquat)、ジベレリン(gibberellin)、シマジン(simazine)、ジメキサノ(dimexano)、ジメスルファゼト(dimesulfazet)、ジメタクロール(dimethachlor)、ジミダゾン(dimidazon)、ジメタメトリン(dimethametryn)、ジメテナミド(dimethenamid)、シメトリン(simetryn)、シメトン(simeton)、ジメピペレート(dimepiperate)、ジメフロン(dimefuron)、シンメチリン(cinmethylin)、スエップ(swep)、スルグリカピン(sulglycapin)、スルコトリオン(sulcotrione)、スルファレート(sulfallate)、スルフェントラゾン(sulfentrazone)、スルホスルフロン(sulfosulfuron)、スルホメツロン(sulfometuron)、スルホメツロンメチル(sulfometuron-methyl)、セクブメトン(secbumeton)、セトキシジム(sethoxydim)、セブチラジン(sebuthylazine)、ターバシル(terbacil)、ダイムロン(daimuron)、ダゾメット(dazomet)、ダラポン(dalapon)、チアザフルロン(thiazafluron)、チアゾピル(thiazopyr)、チアフェナシル(tiafenacil)、チエンカルバゾン(thiencarbazone)、チエンカルバゾン-メチル(thiencarbazone-methyl)、チオカルバジル(tiocarbazil)、チオクロリム(tioclorim)、チオベンカルブ(thiobencarb)、チジアジミン(thidiazimin)、チジアズロン(thidiazuron)、チフェンスルフロン(thifensulfuron)、チフェンスルフロン-メチル(thifensulfuron-methyl)、デスメディファム(desmedipham)、デスメトリン(desmetryn)、テトフルピロリメツ(tetflupyrolimet)、テトラフルロン(tetrafluron)、テニルクロール(thenylchlor)、テブタム(tebutam)、テブチウロン(tebuthiuron)、テルブメトン(terbumeton)、テプラロキシジム(tepraloxydim)、テフリールトリオン(tefuryltrione)、テムボトリオン(tembotrione)、デラクロール(delachlor)、テルバシル(terbacil)、テルブカルブ(terbucarb)、テルブクロール(terbuchlor)、テルブチラジン(terbuthylazine)、テルブトリン(terbutryn)、トプラメゾン(topramezone)、トラルコキシジム(tralkoxydim)、トリアジフラム(triaziflam)、トリアスルフロン(triasulfuron)、トリアファモン(triafamone)、トリアレート(tri-allate)、トリエタジン(trietazine)、トリカンバ(tricamba)、トリクロピル(triclopyr)、トリジファン(tridiphane)、トリタック(tritac)、トリトスルフロン(tritosulfuron)、トリピラスルホン(tripyrasulfone)、トリフルジモキサジン(trifludimoxazin)、トリフルスルフロン(triflusulfuron)、トリフルスルフロン-メチル(triflusulfuron-methyl)、トリフルラリン(trifluralin)、トリフロキシスルフロン(trifloxysulfuron)、トリプロピンダン(tripropindan)、トリベヌロン(tribenuron)、トリベヌロン-メチル(tribenuron-methyl)、トリホップ(trifop)、トリホプシメ(trifopsime)、トリメツロン(trimeturon)、トルピラレート(tolpyralate)、ナプタラム(naptalam)、ナプロアニリド(naproanilide)、ナプロパミド(napropamide)、ニコスルフロン(nicosulfuron)、ニトラリン(nitralin)、ニトロフェン(nitrofen)、ニトロフルオルフェン(nitrofluorfen)、ニピラクロフェン(nipyraclofen)、ネブロン(neburon)、ノルフルラゾン(norflurazon)、ノルロン(noruron)、バーバン(barban)、パクロブトラゾール(paclobutrazol)、パラコート(paraquat)、パラフルロン(parafluron)、ハロキシジン(haloxydine)、ハロキシフェン(halauxifen)、ハロキシホップ(haloxyfop)、ハロキシホップ-P(haloxyfop-P)、ハロキシホップ-メチル(haloxyfop-methyl)、ハロサフェン(halosafen)、ハロスルフロン(halosulfuron)、ハロスルフロン-メチル(halosulfuron-methyl)、ビアラホス(bilanafos)、ビクスロゾン(bixlozone)、ピクロラム(picloram)、ピコリナフェン(picolinafen)、ビシクロピロン(bicyclopyrone)、ビスピリバック(bispyribac)、ビスピリバック-ナトリウム(bispyribac-sodium)、ピダノン(pydanon)、ピノキサデン(pinoxaden)、ビピラゾン(bipyrazone)、ビフェノックス(bifenox)、ピペロホス(piperophos)、ヒメキサゾール(hymexazol)、ピラキネート(pyraquinate)、ピラクロニル(pyraclonil)、ピラスルホトール(pyrasulfotole)、ピラゾキシフェン(pyrazoxyfen)、ピラゾスルフロン(pyrazosulfuron)、ピラゾスルフロン-エチル(pyrazosulfuron-ethyl)、ピラゾ
レート(pyrazolate)、ビラナホス(bilanafos)、ピラフルフェン(pyraflufen)、ピラフルフェン-エチル(pyraflufen-ethyl)、ピリクロール(pyriclor)、ピリダホール(pyridafol)、ピリチオバック(pyrithiobac)、ピリチオバック-ナトリウム(pyrithiobac-sodium)、ピリデート(pyridate)、ピリフタリド(pyriftalid)、ピリブチカルブ(pyributicarb)、ピリベンゾキシム(pyribenzoxim)、ピリフルベンゾキシム(pyriflubenzoxim)、ピリミスルファン(pyrimisulfan)、ピリミスルフロン(primisulfuron)、ピリミノバックメチル(pyriminobac-methyl)、ピロキサスルホン(pyroxasulfone)、ピロクスラム(pyroxsulam)、フェナスラム(fenasulam)、フェニソファム(phenisopham)、フェヌロン(fenuron)、フェノキサスルホン(fenoxasulfone)、フェノキサプロップ(fenoxaprop)、フェノキサプロップ-P(fenoxaprop-P)、フェノキサプロップ-エチル(fenoxaprop-ethyl)、フェノチオール(phenothio1)、フェノプロップ(fenoprop)、フェノベンズロン(phenobenzuron)、フェンキノトリオン(fenquinotrione)、フェンチアプロップ(fenthiaprop)、フェンテラコール(fenteracol)、フェントラザミド(fentrazamide)、フェンピラゾン(fenpyrazone)、フェンメディファム(phenmedipham)、フェンメディファム-エチル(phenmedipham-ethyl)、ブタクロール(butachlor)、ブタフェナシル(butafenacil)、ブタミホス(butamifos)、ブチウロン(buthiuron)、ブチダゾール(buthidazole)、ブチレート(butylate)、ブツロン(buturon)、ブテナクロール(butenachlor)、ブトキシジム(butroxydim)、ブトラリン(butralin)、ブトロキシジム(butroxydim)、フラザスルフロン(flazasulfuron)、フラムプロップ(flamprop)、フリロオキシフェン(furyloxyfen)、プリナクロール(prynachlor)、プリミスルフロンメチル(primisulfuron-methyl)、フルアジホップ(fluazifop)、フルアジホップ-P(fluazifop-P)、フルアジホップ-ブチル(fluazifop-butyl)、フルアゾレート(fluazolate)、フルロキシピル(fluroxypyr)、フルオチウロン(fluothiuron)、フルオメツロン(fluometuron)、フルオログリコフェン(fluoroglycofen)、フルロクロリドン(flurochloridone)、フルオロジフェン(fluorodifen)、フルオロニトロフェン(fluoronitrofen)、フルオロミジン(fluoromidine)、フルカルバゾン(flucarbazone)、フルカルバゾン-ナトリウム(flucarbazone-sodium)、フルクロラミノピル(fluchloraminopyr)、フルクロラミノピル‐テフリル(fluchloraminopyr-tefuryl)、フルクロラリン(fluchloralin)、フルセトスルフロン(flucetosulfuron)、フルチアセット(fluthiacet)、フルチアセット-メチル(fluthiacet-methyl)、フルピルスルフロン(flupyrsulfuron)、フルフェナセット(flufenacet)、フルフェニカン(flufenican)、フルフェンピル(flufenpyr)、フルプロパシル(flupropacil)、フルプロパナート(flupropanate)、フルポキサム(flupoxam)、フルミオキサジン(flumioxazin)、フルミクロラック(flumiclorac)、フルミクロラック-ペンチル(flumiclorac-pentyl)、フルミプロピン(flumipropyn)、フルメジン(flumezin)、フルオメツロン(fluometuron)、フルクロラミノピル(fluchloraminopyr)、フルクロラミノピル‐テフリル(fluchloraminopyr-tefuryl)、フルスルフィナム(flusulfinam)、フルフェノキシマシル(flufenoximacil)、フルメトスラム(flumetsulam)、フルリドン(fluridone)、フルルタモン(flurtamone)、フルロキシピル(fluroxypyr)、プレチラクロール(pretilachlor)、プロキサン(proxan)、プログリナジン(proglinazine)、ブロクロゾン(broclozone)、プロシアジン(procyazine)、プロジアミン(prodiamine)、プロスルファリン(prosulfalin)、プロスルフロン(prosulfuron)、プロスルホカルブ(prosulfocarb)、プロパキザホップ(propaquizafop)、プロパクロール(propachlor)、プロパジン(propazine)、プロパニル(propanil)、プロピザミド(propyzamide)、プロピソクロール(propisochlor)、プロヒドロジャスモン(prohydrojasmon)、プロピリスルフロン(propyrisulfuron)、プロファム(propham)、プロフルアゾール(profluazol)、プロフルラリン(profluralin)、プロヘキサジオン-カルシウム(prohexadione-calcium)、プロポキシカルバゾン(propoxycarbazone)、プロポキシカルバゾン-ナトリウム(propoxycarbazone-sodium)、プロホキシジム(profoxydim)、ブロマシル(bromacil)、ブロムピラゾン(brompyrazon)、プロメトリン(prometryn)、プロメトン(prometon)、ブロモキシニル(bromoxynil)、ブロモフェノキシム(bromofenoxim)、ブロモブチド(bromobutide)、ブロモボニル(bromobonil)、フロラスラム(florasulam)、フロルピラウキシフェン(florpyrauxifen)、ヘキサクロロアセトン(hexachloroacetone)、ヘキサジノン(hexazinone)、ペトキサミド(pethoxamid)、ベナゾリン(benazolin)、ペノクスラム(penoxsulam)、ペブレート(pebulate)、ベフルブタミド(beflubutamid)、ベフルブタミド-M(beflubutamid-M)、ベルノレート(vernolate)、ペルフルイドン(perfluidone)、ベンカルバゾン(bencarbazone)、ベンクワイトリオン(benquitrione)、ベンザドックス(benzadox)、ベンジプラム(benzipram)、ベンジルアミノプリン(benzylaminopurine)、ベンズチアズロン(benzthiazuron)、ベンズフェンジゾン(benzfendizone)、ベンスリド(bensulide)、ベンスルフロンメチル(bensulfuron-methyl)、ベンゾイルプロップ(benzoylprop)、ベンゾビシクロン(benzobicyclon)、ベンゾフェナップ(benzofenap)、ベンゾフルオール(benzofluor)、ベンタゾン(bentazone)、ペンタノクロール(pentanochlor)、ベンチオカーブ(benthiocarb)、ペンディメタリン(pendimethalin)、ペントキサゾン(pentoxazone)、ベンフラリン(benfluralin)、ベンフレセート(benfuresate)、ホサミン(fosamine)、ホメサフェン(fomesafen)、ホラムスルフロン(foramsulfuron)、ホルクロルフェニュロン(forchlorfenuron)、マレイン酸ヒドラジド(maleic hydrazide)、メコプロップ(mecoprop)、メコプロップ-P(mecoprop-P)、メジノテルブ(medinoterb)、メソスルフロン(mesosulfuron)、メソスルフロン-メチル(mesosulfuron-methyl)、メソトリオン(mesotrione)、メソプラジン(mesoprazine)、メソプロトリン(methoprotryne)、メタザクロール(metazachlor)、メタゾール(methazole)、メタゾスルフロン(metazosulfuron)、メタベンズチアズロン(methabenzthiazuron)、メタミトロン(metamitron)、メタミホップ(metamifop)、メタム(metam)、メタルプロパリン(methalpropalin)、メチウロン(methiuron)、メチオゾリン(methiozolin)、メチオベンカルブ(methiobencarb)、メチルダイムロン(methyldymron)、メトクスロン(metoxuron)、メトスラム(metosulam)、メトスルフロン(metsulfuron)、メトスルフロン-メチル(metsu1furon-methy1)、メトフルラゾン(metflurazon)、メトブロムロン(metobromuron)、メトベンズロン(metobenzuron)、メトメトン(methometon)、メトラクロール(metolachlor)、メトリブジン(metribuzin)、メピコートクロリド(mepiquat-chloride)、メフェナセット(mefenacet)、メフルイジド(mefluidide)、モナリド(monalide)、モニソウロン(monisouron)、モニュヌロン(monuron)、モノクロル酢酸(monochloroacetic acid)、モノリニュヌロン(monolinuron)、モリネート(molinate)、モルファムコート(morfamquat)、ヨードスルフロン(iodosulfuron)、ヨードスルフロンメチルナトリウム(iodosulfuron-methyl-sodium)、ヨードボニル(iodobonil)、ヨードメタン(iodomethane)、ラクトフェン(lactofen)、ランコトリオン(lancotrione)、リヌロン(linuron)、リミソキサフェン(rimisoxafen)、リムスルフロン(rimsulfuron)、レナシル(lenacil)、ローデタニル(rhodethanil)、過酸化カルシウム(calcium peroxide)、臭化メチル(methyl bromide)等を例示することができる。 Similarly, herbicides such as 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2, 4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, icafolin, icafolin-methyl, aclonifen, azafenidin, acifluorfen, aziprotrine, azimus azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone ( amicarbazone), amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, ametrine ( ametryn), alachlor, allidochlor, alloxydim, alorac, iofensulfuron, isouron, isocarbamid, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin ), inabenfide, ipazine, iptriazopyrid, ipfencarbazone, iprymidam, imazaquin, imazapic, imazapyr, imazametapyr (imazamethapyr), imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolauxipyr , indolauxipyr-cyanomethyl, indolebutyric acid, uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron- ethametsulfuron-methyl, ethalfluralin, ethiolate, ethychlozate-ethyl, ethidimuron, etinofen, ethephon, ethoxysulfuron, ethoxyfen, etnipromid, etofumesate, etobenzanid, epyrifenacil, epronaz, erbon, endothal, oxadiazon, oxadiargyl ), oxaziclomefone, oxasulfuron, oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, cafenstrole, cambenge cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop ), quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron ( cumyluron), clacyfos, cliodinate, glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop (clodinafop), clodinafop-propargyl, chlorotoluron, clopyralid, cloproxydim, cloprop, chlorbromuron, clofop, clomazone , chlomethoxyni1, chlomethoxyfen, clomeprop, chlorazifop, chlorazine, chloranocryl, chloramben, chloransulam, chloransulam-methyl ), chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlortoluron, chlornitrofen, chlorfe chlorfenac, chlorfenprop, chlorbufam, chlorphthalim, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil, chloroxuron, chlorotoluron, chloropon, saflufenacil, cyanazine, cyanatryn, di-allate ), diuron, diethamquat, dioxopyritrione, dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron ( cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlorprop, dichlorprop-P, dichlobenil, diclofop, diclofop-methyl , dichlormate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosum (dinosam), cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, cypyrafluone, diphenamide, difenoxuron (difenoxuron), difenopenten, difenzoquat, cybutryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromide (cypromid), cyperquat, gibberellin, simazine, dimexano, dimesulfazet, dimethachlor, dimidazon, dimethametryn, dimethenamid, simetrine simetryn, simeton, dimepiperate, dimefuron, cinmethylin, swep, sulglycapin, sulcotrione, sulfalate, sulfentrazone ( sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton, setthoxydim, sebuthylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr, tiafenacil, thiencarbazone, thiencarbazone-methyl, tiocarbazil, tioclorim, thiobencarb (thiobencarb), thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet ), tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delachlor , terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone ( triafamone, tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron, tripyrasulfone, trifludimoxazin, triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron , tribenuron-methyl, trifop, trifopsime, trimeturon, tolpyralate, naptalam, naproanilide, napropamide, nicosulfuron ), nitralin, nitrofen, nitrofluorfen, nipyraclofen, neburon, norflurazon, noruron, barban, paclobutrazol ), paraquat, parafluron, haloxydine, haloxifen, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, bilanafos, bixlozone, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium (bispyribac-sodium), pydanon, pinoxaden, bipyrazone, bifenox, piperophos, hymexazol, pyraquinate, pyraclonil, pyrasulfotol ( pyrasulfotole), pyrazoxyfen, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, bilanafos, pyraflufen, pyraflufen-ethyl, pyriclor , pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyribenzoxim, pyriflubenzoxim, pyrimisul pyrimisulfan, primisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisopham, fenuron, phenox fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, phenothiol (phenothio1), fenoprop, phenobenzuron (phenobenzuron), fenquinotrione, fenthiaprop, fenteracol, fentrazamide, fenpyrazone, phenmedipham, phenmedipham-ethyl ), butachlor, butafenacil, butamifos, buthiuron, buthidazole, butylate, buturon, butenachlor, butroxydim, butralin ), butroxydim, flazasulfuron, flamprop, furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop, fluazifop- P (fluazifop-P), fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium, fluchloraminopyr, fluchloraminopyr-tefuryl tefuryl), fluchloralin, flucetosulfuron, fluthiacet, fluthiacet-methyl, flupyrsulfuron, flufenacet, flufenican, flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn , flumezin, fluometuron, fluchloraminopyr, fluchloraminopyr-tefuryl, flusulfinam, flufenoximacil, flumetsulam , fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proglinazine, broclozone, procyazine, prodiamine, prosulfarin (prosulfalin), prosulfuron (prosulfuron), prosulfocarb (prosulfocarb), propaquizafop (propaquizafop), propachlor (propachlor), propazine (propazine), propanil (propanil), propyzamide, propisochlor ), prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin, prohexadione-calcium, propoxycarbazone , propoxycarbazone-sodium, profoxydim, bromacil, brompyrazone, prometryn, prometon, bromoxynil, bromofenoxim, bromobutide (bromobutide), bromobonil, florasulam, florpyrauxifen, hexachloroacetone, hexazinone, petoxamide, benazolin, penoxsulam, pebrate ( pebulate), beflubutamide, beflubutamid-M, vernolate, perfluidone, bencarbazone, benquitrione, benzadox, benzipram , benzylaminopurine, benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl, benzoylprop, benzobicyclon, benzophe benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate , fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazide, mecoprop, mecoprop-P, mezinoterb (medinoterb), mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprazine, mesoprotryne, metazachlor, methazole, metazosulfuron, meth methabenzthiazuron, metamitron, metamifop, metam, methalpropalin, methiuron, methiozolin, methiobencarb, methyldymron ), metoxuron, metosulam, metsulfuron, metsulfuron-methyl (metsu1furon-methy1), metflurazon, metobromuron, metobenzuron, methometon, metolachlor ), metribuzin, mepiquat-chloride, mefenacet, mefluidide, monalide, monisouron, monuron, monochloroacetic acid, monolinuron (monolinuron), molinate, morphamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen , lancotrione, linuron, rimisoxafen, rimsulfuron, lenacil, rhodethanil, calcium peroxide, methyl bromide, etc. I can give an example.
レート(pyrazolate)、ビラナホス(bilanafos)、ピラフルフェン(pyraflufen)、ピラフルフェン-エチル(pyraflufen-ethyl)、ピリクロール(pyriclor)、ピリダホール(pyridafol)、ピリチオバック(pyrithiobac)、ピリチオバック-ナトリウム(pyrithiobac-sodium)、ピリデート(pyridate)、ピリフタリド(pyriftalid)、ピリブチカルブ(pyributicarb)、ピリベンゾキシム(pyribenzoxim)、ピリフルベンゾキシム(pyriflubenzoxim)、ピリミスルファン(pyrimisulfan)、ピリミスルフロン(primisulfuron)、ピリミノバックメチル(pyriminobac-methyl)、ピロキサスルホン(pyroxasulfone)、ピロクスラム(pyroxsulam)、フェナスラム(fenasulam)、フェニソファム(phenisopham)、フェヌロン(fenuron)、フェノキサスルホン(fenoxasulfone)、フェノキサプロップ(fenoxaprop)、フェノキサプロップ-P(fenoxaprop-P)、フェノキサプロップ-エチル(fenoxaprop-ethyl)、フェノチオール(phenothio1)、フェノプロップ(fenoprop)、フェノベンズロン(phenobenzuron)、フェンキノトリオン(fenquinotrione)、フェンチアプロップ(fenthiaprop)、フェンテラコール(fenteracol)、フェントラザミド(fentrazamide)、フェンピラゾン(fenpyrazone)、フェンメディファム(phenmedipham)、フェンメディファム-エチル(phenmedipham-ethyl)、ブタクロール(butachlor)、ブタフェナシル(butafenacil)、ブタミホス(butamifos)、ブチウロン(buthiuron)、ブチダゾール(buthidazole)、ブチレート(butylate)、ブツロン(buturon)、ブテナクロール(butenachlor)、ブトキシジム(butroxydim)、ブトラリン(butralin)、ブトロキシジム(butroxydim)、フラザスルフロン(flazasulfuron)、フラムプロップ(flamprop)、フリロオキシフェン(furyloxyfen)、プリナクロール(prynachlor)、プリミスルフロンメチル(primisulfuron-methyl)、フルアジホップ(fluazifop)、フルアジホップ-P(fluazifop-P)、フルアジホップ-ブチル(fluazifop-butyl)、フルアゾレート(fluazolate)、フルロキシピル(fluroxypyr)、フルオチウロン(fluothiuron)、フルオメツロン(fluometuron)、フルオログリコフェン(fluoroglycofen)、フルロクロリドン(flurochloridone)、フルオロジフェン(fluorodifen)、フルオロニトロフェン(fluoronitrofen)、フルオロミジン(fluoromidine)、フルカルバゾン(flucarbazone)、フルカルバゾン-ナトリウム(flucarbazone-sodium)、フルクロラミノピル(fluchloraminopyr)、フルクロラミノピル‐テフリル(fluchloraminopyr-tefuryl)、フルクロラリン(fluchloralin)、フルセトスルフロン(flucetosulfuron)、フルチアセット(fluthiacet)、フルチアセット-メチル(fluthiacet-methyl)、フルピルスルフロン(flupyrsulfuron)、フルフェナセット(flufenacet)、フルフェニカン(flufenican)、フルフェンピル(flufenpyr)、フルプロパシル(flupropacil)、フルプロパナート(flupropanate)、フルポキサム(flupoxam)、フルミオキサジン(flumioxazin)、フルミクロラック(flumiclorac)、フルミクロラック-ペンチル(flumiclorac-pentyl)、フルミプロピン(flumipropyn)、フルメジン(flumezin)、フルオメツロン(fluometuron)、フルクロラミノピル(fluchloraminopyr)、フルクロラミノピル‐テフリル(fluchloraminopyr-tefuryl)、フルスルフィナム(flusulfinam)、フルフェノキシマシル(flufenoximacil)、フルメトスラム(flumetsulam)、フルリドン(fluridone)、フルルタモン(flurtamone)、フルロキシピル(fluroxypyr)、プレチラクロール(pretilachlor)、プロキサン(proxan)、プログリナジン(proglinazine)、ブロクロゾン(broclozone)、プロシアジン(procyazine)、プロジアミン(prodiamine)、プロスルファリン(prosulfalin)、プロスルフロン(prosulfuron)、プロスルホカルブ(prosulfocarb)、プロパキザホップ(propaquizafop)、プロパクロール(propachlor)、プロパジン(propazine)、プロパニル(propanil)、プロピザミド(propyzamide)、プロピソクロール(propisochlor)、プロヒドロジャスモン(prohydrojasmon)、プロピリスルフロン(propyrisulfuron)、プロファム(propham)、プロフルアゾール(profluazol)、プロフルラリン(profluralin)、プロヘキサジオン-カルシウム(prohexadione-calcium)、プロポキシカルバゾン(propoxycarbazone)、プロポキシカルバゾン-ナトリウム(propoxycarbazone-sodium)、プロホキシジム(profoxydim)、ブロマシル(bromacil)、ブロムピラゾン(brompyrazon)、プロメトリン(prometryn)、プロメトン(prometon)、ブロモキシニル(bromoxynil)、ブロモフェノキシム(bromofenoxim)、ブロモブチド(bromobutide)、ブロモボニル(bromobonil)、フロラスラム(florasulam)、フロルピラウキシフェン(florpyrauxifen)、ヘキサクロロアセトン(hexachloroacetone)、ヘキサジノン(hexazinone)、ペトキサミド(pethoxamid)、ベナゾリン(benazolin)、ペノクスラム(penoxsulam)、ペブレート(pebulate)、ベフルブタミド(beflubutamid)、ベフルブタミド-M(beflubutamid-M)、ベルノレート(vernolate)、ペルフルイドン(perfluidone)、ベンカルバゾン(bencarbazone)、ベンクワイトリオン(benquitrione)、ベンザドックス(benzadox)、ベンジプラム(benzipram)、ベンジルアミノプリン(benzylaminopurine)、ベンズチアズロン(benzthiazuron)、ベンズフェンジゾン(benzfendizone)、ベンスリド(bensulide)、ベンスルフロンメチル(bensulfuron-methyl)、ベンゾイルプロップ(benzoylprop)、ベンゾビシクロン(benzobicyclon)、ベンゾフェナップ(benzofenap)、ベンゾフルオール(benzofluor)、ベンタゾン(bentazone)、ペンタノクロール(pentanochlor)、ベンチオカーブ(benthiocarb)、ペンディメタリン(pendimethalin)、ペントキサゾン(pentoxazone)、ベンフラリン(benfluralin)、ベンフレセート(benfuresate)、ホサミン(fosamine)、ホメサフェン(fomesafen)、ホラムスルフロン(foramsulfuron)、ホルクロルフェニュロン(forchlorfenuron)、マレイン酸ヒドラジド(maleic hydrazide)、メコプロップ(mecoprop)、メコプロップ-P(mecoprop-P)、メジノテルブ(medinoterb)、メソスルフロン(mesosulfuron)、メソスルフロン-メチル(mesosulfuron-methyl)、メソトリオン(mesotrione)、メソプラジン(mesoprazine)、メソプロトリン(methoprotryne)、メタザクロール(metazachlor)、メタゾール(methazole)、メタゾスルフロン(metazosulfuron)、メタベンズチアズロン(methabenzthiazuron)、メタミトロン(metamitron)、メタミホップ(metamifop)、メタム(metam)、メタルプロパリン(methalpropalin)、メチウロン(methiuron)、メチオゾリン(methiozolin)、メチオベンカルブ(methiobencarb)、メチルダイムロン(methyldymron)、メトクスロン(metoxuron)、メトスラム(metosulam)、メトスルフロン(metsulfuron)、メトスルフロン-メチル(metsu1furon-methy1)、メトフルラゾン(metflurazon)、メトブロムロン(metobromuron)、メトベンズロン(metobenzuron)、メトメトン(methometon)、メトラクロール(metolachlor)、メトリブジン(metribuzin)、メピコートクロリド(mepiquat-chloride)、メフェナセット(mefenacet)、メフルイジド(mefluidide)、モナリド(monalide)、モニソウロン(monisouron)、モニュヌロン(monuron)、モノクロル酢酸(monochloroacetic acid)、モノリニュヌロン(monolinuron)、モリネート(molinate)、モルファムコート(morfamquat)、ヨードスルフロン(iodosulfuron)、ヨードスルフロンメチルナトリウム(iodosulfuron-methyl-sodium)、ヨードボニル(iodobonil)、ヨードメタン(iodomethane)、ラクトフェン(lactofen)、ランコトリオン(lancotrione)、リヌロン(linuron)、リミソキサフェン(rimisoxafen)、リムスルフロン(rimsulfuron)、レナシル(lenacil)、ローデタニル(rhodethanil)、過酸化カルシウム(calcium peroxide)、臭化メチル(methyl bromide)等を例示することができる。 Similarly, herbicides such as 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2, 4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, icafolin, icafolin-methyl, aclonifen, azafenidin, acifluorfen, aziprotrine, azimus azimsulfuron, asulam, acetochlor, atrazine, atraton, anisuron, anilofos, aviglycine, abscisic acid, amicarbazone ( amicarbazone), amidosulfuron, amitrole, aminocyclopyrachlor, aminopyralid, amibuzin, amiprophos-methyl, ametridione, ametrine ( ametryn), alachlor, allidochlor, alloxydim, alorac, iofensulfuron, isouron, isocarbamid, isoxachlortole, isoxapyrifop, isoxaflutole, isoxaben, isocil, isonoruron, isoproturon, isopropalin, isopolinate, isomethiozin ), inabenfide, ipazine, iptriazopyrid, ipfencarbazone, iprymidam, imazaquin, imazapic, imazapyr, imazametapyr (imazamethapyr), imazamethabenz, imazamethabenz-methyl, imazamox, imazethapyr, imazosulfuron, indaziflam, indanofan, indolauxipyr , indolauxipyr-cyanomethyl, indolebutyric acid, uniconazole-P, eglinazine, esprocarb, ethametsulfuron, ethametsulfuron- ethametsulfuron-methyl, ethalfluralin, ethiolate, ethychlozate-ethyl, ethidimuron, etinofen, ethephon, ethoxysulfuron, ethoxyfen, etnipromid, etofumesate, etobenzanid, epyrifenacil, epronaz, erbon, endothal, oxadiazon, oxadiargyl ), oxaziclomefone, oxasulfuron, oxapyrazon, oxyfluorfen, oryzalin, orthosulfamuron, orbencarb, cafenstrole, cambenge cambendichlor, carbasulam, carfentrazone, carfentrazone-ethyl, karbutilate, carbetamide, carboxazole, quizalofop ), quizalofop-P, quizalofop-ethyl, xylachlor, quinoclamine, quinonamid, quinclorac, quinmerac, cumyluron ( cumyluron), clacyfos, cliodinate, glyphosate, glufosinate, glufosinate-P, credazine, clethodim, cloxyfonac, clodinafop (clodinafop), clodinafop-propargyl, chlorotoluron, clopyralid, cloproxydim, cloprop, chlorbromuron, clofop, clomazone , chlomethoxyni1, chlomethoxyfen, clomeprop, chlorazifop, chlorazine, chloranocryl, chloramben, chloransulam, chloransulam-methyl ), chloridazon, chlorimuron, chlorimuron-ethyl, chlorsulfuron, chlorthal, chlorthiamid, chlortoluron, chlornitrofen, chlorfe chlorfenac, chlorfenprop, chlorbufam, chlorphthalim, chlorflurazole, chlorflurenol, chlorprocarb, chlorpropham, chlormequat, chloreturon, chloroxynil, chloroxuron, chlorotoluron, chloropon, saflufenacil, cyanazine, cyanatryn, di-allate ), diuron, diethamquat, dioxopyritrione, dicamba, cycluron, cycloate, cycloxydim, diclosulam, cyclosulfamuron ( cyclosulfamuron, cyclopyranil, cyclopyrimorate, dichlorprop, dichlorprop-P, dichlobenil, diclofop, diclofop-methyl , dichlormate, dichloralurea, diquat, cisanilide, disul, siduron, dithiopyr, dinitramine, cinidon-ethyl, dinosum (dinosam), cinosulfuron, dinoseb, dinoterb, dinofenate, dinoprop, cyhalofop-butyl, cypyrafluone, diphenamide, difenoxuron (difenoxuron), difenopenten, difenzoquat, cybutryne, cyprazine, cyprazole, diflufenican, diflufenzopyr, dipropetryn, cypromide (cypromid), cyperquat, gibberellin, simazine, dimexano, dimesulfazet, dimethachlor, dimidazon, dimethametryn, dimethenamid, simetrine simetryn, simeton, dimepiperate, dimefuron, cinmethylin, swep, sulglycapin, sulcotrione, sulfalate, sulfentrazone ( sulfentrazone, sulfosulfuron, sulfometuron, sulfometuron-methyl, secbumeton, setthoxydim, sebuthylazine, terbacil, daimuron, dazomet, dalapon, thiazafluron, thiazopyr, tiafenacil, thiencarbazone, thiencarbazone-methyl, tiocarbazil, tioclorim, thiobencarb (thiobencarb), thidiazimin, thidiazuron, thifensulfuron, thifensulfuron-methyl, desmedipham, desmetryn, tetflupyrolimet ), tetrafluron, thenylchlor, tebutam, tebuthiuron, terbumeton, tepraloxydim, tefuryltrione, tembotrione, delachlor , terbacil, terbucarb, terbuchlor, terbuthylazine, terbutryn, topramezone, tralkoxydim, triaziflam, triasulfuron, triafamone ( triafamone, tri-allate, trietazine, tricamba, triclopyr, tridiphane, tritac, tritosulfuron, tripyrasulfone, trifludimoxazin, triflusulfuron, triflusulfuron-methyl, trifluralin, trifloxysulfuron, tripropindan, tribenuron , tribenuron-methyl, trifop, trifopsime, trimeturon, tolpyralate, naptalam, naproanilide, napropamide, nicosulfuron ), nitralin, nitrofen, nitrofluorfen, nipyraclofen, neburon, norflurazon, noruron, barban, paclobutrazol ), paraquat, parafluron, haloxydine, haloxifen, haloxyfop, haloxyfop-P, haloxyfop-methyl, halosafen, halosulfuron, halosulfuron-methyl, bilanafos, bixlozone, picloram, picolinafen, bicyclopyrone, bispyribac, bispyribac-sodium (bispyribac-sodium), pydanon, pinoxaden, bipyrazone, bifenox, piperophos, hymexazol, pyraquinate, pyraclonil, pyrasulfotol ( pyrasulfotole), pyrazoxyfen, pyrazosulfuron, pyrazosulfuron-ethyl, pyrazolate, bilanafos, pyraflufen, pyraflufen-ethyl, pyriclor , pyridafol, pyrithiobac, pyrithiobac-sodium, pyridate, pyriftalid, pyributicarb, pyribenzoxim, pyriflubenzoxim, pyrimisul pyrimisulfan, primisulfuron, pyriminobac-methyl, pyroxasulfone, pyroxsulam, fenasulam, phenisopham, fenuron, phenox fenoxasulfone, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, phenothiol (phenothio1), fenoprop, phenobenzuron (phenobenzuron), fenquinotrione, fenthiaprop, fenteracol, fentrazamide, fenpyrazone, phenmedipham, phenmedipham-ethyl ), butachlor, butafenacil, butamifos, buthiuron, buthidazole, butylate, buturon, butenachlor, butroxydim, butralin ), butroxydim, flazasulfuron, flamprop, furyloxyfen, prynachlor, primisulfuron-methyl, fluazifop, fluazifop- P (fluazifop-P), fluazifop-butyl, fluazolate, fluroxypyr, fluothiuron, fluometuron, fluoroglycofen, flurochloridone, fluorodifen, fluoronitrofen, fluoromidine, flucarbazone, flucarbazone-sodium, fluchloraminopyr, fluchloraminopyr-tefuryl tefuryl), fluchloralin, flucetosulfuron, fluthiacet, fluthiacet-methyl, flupyrsulfuron, flufenacet, flufenican, flufenpyr, flupropacil, flupropanate, flupoxam, flumioxazin, flumiclorac, flumiclorac-pentyl, flumipropyn , flumezin, fluometuron, fluchloraminopyr, fluchloraminopyr-tefuryl, flusulfinam, flufenoximacil, flumetsulam , fluridone, flurtamone, fluroxypyr, pretilachlor, proxan, proglinazine, broclozone, procyazine, prodiamine, prosulfarin (prosulfalin), prosulfuron (prosulfuron), prosulfocarb (prosulfocarb), propaquizafop (propaquizafop), propachlor (propachlor), propazine (propazine), propanil (propanil), propyzamide, propisochlor ), prohydrojasmon, propyrisulfuron, propham, profluazol, profluralin, prohexadione-calcium, propoxycarbazone , propoxycarbazone-sodium, profoxydim, bromacil, brompyrazone, prometryn, prometon, bromoxynil, bromofenoxim, bromobutide (bromobutide), bromobonil, florasulam, florpyrauxifen, hexachloroacetone, hexazinone, petoxamide, benazolin, penoxsulam, pebrate ( pebulate), beflubutamide, beflubutamid-M, vernolate, perfluidone, bencarbazone, benquitrione, benzadox, benzipram , benzylaminopurine, benzthiazuron, benzfendizone, bensulide, bensulfuron-methyl, benzoylprop, benzobicyclon, benzophe benzofenap, benzofluor, bentazone, pentanochlor, benthiocarb, pendimethalin, pentoxazone, benfluralin, benfuresate , fosamine, fomesafen, foramsulfuron, forchlorfenuron, maleic hydrazide, mecoprop, mecoprop-P, mezinoterb (medinoterb), mesosulfuron, mesosulfuron-methyl, mesotrione, mesoprazine, mesoprotryne, metazachlor, methazole, metazosulfuron, meth methabenzthiazuron, metamitron, metamifop, metam, methalpropalin, methiuron, methiozolin, methiobencarb, methyldymron ), metoxuron, metosulam, metsulfuron, metsulfuron-methyl (metsu1furon-methy1), metflurazon, metobromuron, metobenzuron, methometon, metolachlor ), metribuzin, mepiquat-chloride, mefenacet, mefluidide, monalide, monisouron, monuron, monochloroacetic acid, monolinuron (monolinuron), molinate, morphamquat, iodosulfuron, iodosulfuron-methyl-sodium, iodobonil, iodomethane, lactofen , lancotrione, linuron, rimisoxafen, rimsulfuron, lenacil, rhodethanil, calcium peroxide, methyl bromide, etc. I can give an example.
また、生物農薬として例えば、核多角体ウイルス(Nuclear polyhedrosis virus、NPV)、顆粒病ウイルス(Granulosis virus、GV)、細胞質多角体病ウイルス(Cytoplasmic polyhedrosis virus、CPV)、昆虫ポックスウイルス(Entomopoxi virus 、EPV)等のウイルス製剤、モナクロスポリウム・フィマトパガム(Monacrosporium phymatophagum)、スタイナ-ネマ・カーポカプサエ(Steinernema carpocapsae)、スタイナ-ネマ・クシダエ(Steinernema kushidai)、パスツーリア・ペネトランス(Pasteuria penetrans)等の殺虫又は殺線虫剤として利用される微生物農薬、トリコデルマ・リグノラン(Trichoderma lignorum)、アグロバクテリウウム・ラジオバクター(Agrobacterium radiobactor)、非病原性エルビニア・カロトボーラ(Erwinia carotovora)、バチルス・ズブチリス(Bacillus subtilis)等の殺菌剤として使用される微生物農薬、ザントモナス・キャンペストリス(Xanthomonas campestris)等の除草剤として利用される生物農薬などと混合して使用することにより、同様の効果が期待できる。
In addition, biopesticides include, for example, nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), and entomopoxi virus (EPV). ), insecticides or nematicides such as Monacrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasteuria penetrans, etc. As a microbial pesticide, used as a fungicide for Trichoderma lignorum, Agrobacterium radiobacter, non-pathogenic Erwinia carotovora, Bacillus subtilis, etc. A similar effect can be expected by mixing the microbial pesticides used in this invention with biological pesticides used as herbicides such as Xanthomonas campestris.
更に、生物農薬として例えば、オンシツツヤコバチ(Encarsia formosa)、コレマンアブラバチ(Aphidius colemani)、ショクガタマバエ(Aphidoletes aphidimyza)、イサエアヒメコバチ(Diglyphus isaea)、ハモグリコマユバチ(Dacnusa sibirica)、チリカブリダニ(Phytoseiulus persimilis)、ククメリスカブリダニ(Amblyseius cucumeris)、ナミヒメハナカメムシ(Orius sauteri)等の天敵生物、ボーベリア・ブロンニアティ(Beauveria brongniartii)等の微生物農薬、(Z)-10-テトラデセニル=アセタート、(E,Z)-4,10-テトラデカジニエル=アセタート、(Z)-8-ドデセニル=アセタート、(Z)-11-テトラデセニル=アセタート、(Z)-13-イコセン-10-オン、14-メチル-1-オクタデセン等のフェロモン剤と併用することも可能である。
In addition, biopesticides such as Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusa sibirica, Phytoseiulus natural enemy organisms such as Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z)-10-tetradecenyl acetate, (E,Z )-4,10-tetradecadinyl acetate, (Z)-8-dodecenyl acetate, (Z)-11-tetradecenyl acetate, (Z)-13-icocen-10-one, 14-methyl-1 - It is also possible to use it in combination with a pheromone agent such as octadecene.
また、本発明の一般式(1)で表される化合物又はその塩は、動物の寄生虫防除にも適している。動物の寄生虫は、宿主動物の体内又は体表に生息し、宿主動物に不利益をもたらすものであり、宿主動物の体表に生息する外部寄生虫と体内に生息する内部寄生虫とに大別され、本発明の一般式(1)で表される化合物又はその塩は、動物用外部寄生虫防除剤又は動物用内部寄生虫防除剤としても適用できる。
Furthermore, the compound represented by general formula (1) of the present invention or a salt thereof is also suitable for controlling parasites in animals. Animal parasites live in or on the host animal's body and cause a disadvantage to the host animal. The compound represented by the general formula (1) of the present invention or a salt thereof can also be applied as an animal ectoparasiticide or an animal endoparasite controller.
本発明の一般式(1)で表される化合物又はその塩を、動物用外部寄生虫防除剤又は動物用内部寄生虫防除剤として適用する場合、適用できる動物としては、例えば、豚、馬、牛、羊、山羊、兎、ラクダ、水牛、鹿、ミンク、チンチラなどの家畜、犬、猫、小鳥、猿などの愛玩動物、ラット、マウス、ゴールデンハムスター、モルモットなどの実験動物、鶏、カモ、合鴨、ウズラ、アヒル、ガチョウ、七面鳥などの家禽、ヒトなどが挙げられるが、これらに限定されるものではない。また、タイ、ヒラメ、マグロ、ハマチ、ウナギなどの養殖魚類、エビ、カニ、ホタテ、カキ、アサリ、ハマグリなどの甲殻類や貝類にも適用できる。
When the compound represented by the general formula (1) of the present invention or a salt thereof is applied as an animal ectoparasite control agent or an animal endoparasite control agent, examples of applicable animals include pigs, horses, Livestock such as cows, sheep, goats, rabbits, camels, water buffalo, deer, mink, and chinchillas, pet animals such as dogs, cats, small birds, and monkeys, laboratory animals such as rats, mice, golden hamsters, and guinea pigs, chickens, ducks, Examples include, but are not limited to, poultry such as ducks, quail, ducks, geese, and turkeys, and humans. It can also be applied to farmed fish such as sea bream, flounder, tuna, yellowtail, and eel, as well as crustaceans and shellfish such as shrimp, crab, scallops, oysters, clams, and clams.
本発明の動物用外部寄生虫防除剤が防除可能な外部寄生虫としては、例えば、Rhipicephalus属(Rhipicaphalus(Boophilus) microplus、Rhipicephalus sanguineusなど)、Amblyomma属、Dermacentor属、Haemaphysalis属、Hyalomma属、Ixodes属、Rhipicentor属、Margaropus属、Argas属、Otobius属、Ornithodoros属、Chorioptes属(Chorioptes bovisなど)、Psoroptes属(Psoroptes ovisなど)、Cheyletiella属、Dermanyssus属(Dermanyssus gallinaeなど)、Ortnithonyssus属、Demodex属(Demodex canisなど)、Sarcoptes属(Sarcoptes scabieiなど)、Psorergates属、Siphonaptera目(Ctenocephalides felis、Ctenocephalides canisなど)、Diptera目(Musca spp、Gasterophilus intestinalis、Oestrus ovisなど)、Phthiraptera目(Bovicola Ovis、Bovicola Bovisなど)、Lepidoptera目、Coleoptera目、Homoptera目、Haematopota属、Tabunus属、Haematobia属(Haematobia irritansなど)、Stomoxys属、Lucilia属、Lepeophtheirus属などが挙げられるがこれらに限定されるものではない。
Examples of ectoparasites that can be controlled by the animal ectoparasite control agent of the present invention include the genus Rhipicephalus (Rhipicaphalus (Boophilus) microplus, Rhipicephalus sanguineus, etc.), the genus Amblyomma, the genus Dermacentor, the genus Haemaphysalis, the genus Hyalomma, and the genus Ixodes. , Rhipicentor, Margaropus, Argas, Otobius, Ornithodoros, Chorioptes (such as Chorioptes bovis), Psoroptes (such as Psoroptes ovis), Cheyletiella, Dermanyssus (such as Dermanyssus gallinae), Ortnithonyssus, Demodex canis), Sarcoptes (e.g. Sarcoptes scabiei), Psorergates, order Siphonaptera (e.g. Ctenocephalides felis, Ctenocephalides canis), order Diptera (e.g. Musca spp, Gasterophilus intestinalis, Oestrus ovis), order Phthiraptera (e.g. Bovicola Ovis, Bovicola Bovis) , the order Lepidoptera, the order Coleoptera, the order Homoptera, the genus Haematopota, the genus Tabunus, the genus Haematobia (such as Haematobia irritans), the genus Stomoxys, the genus Lucilia, and the genus Lepeophtheirus.
さらに具体的には、ダニ類として例えば、オウシマダニ(Boophilus microplus)、クリイロコイタマダニ(Rhipicephalus sanguineus)、フタトゲチマダニ(Haemaphysalis longicornis)、キチマダニ(Haemaphysalis flava)、ツリガネチマダニ(Haemaphysaliscampanulata)、イスカチマダニ(Haemaphysalis concinna)、ヤマトチマダニ(Haemaphysalisjaponica)、ヒゲナガチマダニ(Haemaphysalis kitaokai)、イヤスチマダニ(Haemaphysalis ias)、ヤマトマダニ(Ixodes ovatus)、タネガタマダニ(Ixodes nipponensis)、シュルツェマダニ(Ixodespersulcatus)、タカサゴキララマダニ(Amblyommatestudinarium)、オオトゲチマダニ(Haemaphysalis megaspinosa)、アミノカクマダニ(Dermacentor reticulatus)、及びタイワンカクマダニ(Dermacentor taiwanesis)のようなマダニ類、ワクモ(Dermanyssus gallinae)、トリサシダニ(Ornithonyssus sylviarum)、及びミナミトリサシダニ(Ornithonyssus bursa)のようなトリサシダニ類、ナンヨウツツガムシ(Eutrombicula wichmanni)、アカツツガムシ(Leptotrombidium akamushi)、フトゲツツガムシ(Leptotrombidium pallidum)、フジツツガムシ(Leptotrombidium fuji)、トサツツガムシ(Leptotrombidium tosa)、ヨーロッパアキダニ(Neotrombicula autumnalis)、アメリカツツガムシ(Eutrombicula alfreddugesi)、及びミヤガワタマツツガムシ(Helenicula miyagawai)のようなツツガムシ類、イヌツメダニ(Cheyletiella yasguri)、ウサギツメダニ(Cheyletiella parasitivorax)、及びネコツメダニ(Cheyletiella blakei)のようなツメダニ類、ウサギキュウセンダニ(Psoroptes cuniculi)、ウシショクヒダニ(Chorioptes bovis)、イヌミミヒゼンダニ(Otodectes cynotis)、ヒゼンダニ(Sarcoptes scabiei)、及びネコショウセンコウヒゼンダニ(Notoedres cati)のようなヒゼンダニ類、並びにイヌニキビダニ(Demodex canis)のようなニキビダニ類などが挙げられる。
More specifically, examples of mites include Boophilus microplus, Rhipicephalus sanguineus, Haemaphysalis longicornis, Haemaphysalis flava, Haemaphysalis campanulata, and Haemaphysalis concinna. , Haemaphysalis japonica, Haemaphysalis kitaokai, Haemaphysalis ias, Ixodes ovatus, Ixodes nipponensis, Ixodespersulcatus, Amblyommatestudinarium, Haemaphysalis megaspinosa , Dermacentor reticulatus, and Dermacentor taiwanesis; Dermacentor mites such as Dermanyssus gallinae, Ornithonyssus sylviarum, and Ornithonyssus bursa; (Eutrombicula wichmanni), Leptotrombidium akamushi, Leptotrombidium pallidum, Leptotrombidium fuji, Leptotrombidium tosa, European red mite (Neotrombicula autumnalis), American chigger (Eutrombicula alfredduge) si), and Chiggers such as Helenicula miyagawai, Chrysanthemum mites such as Cheyletiella yasguri, Cheyletiella parasitivorax, and Cheyletiella blakei, Psoroptes cuniculi, Chorioptes bovis ), Demodex mites such as Otodectes cynotis, Sarcoptes scabiei, and Notoedres cati, and Demodex mites such as Demodex canis.
ノミ類として例えば、ヒトノミ科(Pulicidae)、及びナガノミ科(Ceratephyllus)などが挙げられる。ヒトノミ科に属するノミ類としては、例えば、イヌノミ(Ctenocephalidescanis)、ネコノミ(Ctenocephalides felis)、ヒトノミ(Pulex irritans)、ニワトリフトノミ(Echidnophaga gallinacea)、ケオプスネズミノミ(Xenopsylla cheopis)、メクラネズミノミ(Leptopsylla segnis)、ヨーロッパネズミノミ(Nosopsyllus fasciatus)、及びヤマトネズミノミ(Monopsyllus anisus)などが挙げられる。
Examples of fleas include Pulicidae and Ceratephyllus. Examples of fleas belonging to the human flea family include dog flea (Ctenocephalidescanis), cat flea (Ctenocephalides felis), human flea (Pulex irritans), chicken flea (Echidnophaga gallinacea), Cheops rat flea (Xenopsylla cheopis), and blind rat flea (Leptopsylla segnis), the European rat flea (Nosopsyllus fasciatus), and the mountain rat flea (Monopsyllus anisus).
また、ウシジラミ(Haematopinus eurysternus)、ウマジラミ(Haematopinus asini)、ヒツジジラミ(Dalmalinia ovis)、ウシホソジラミ(Linognathus vituli)、ブタジラミ(Haematopinus suis)、ケジラミ(Phthirus pubis)、及びアタマジラミ(Pediculus capitis)のようなシラミ類、並びにイヌハジラミ(Trichodectes canis)のようなハジラミ類、ウシアブ(Tabanus trigonus)、ウアイヌカカ(Culicoides schultzei)、及びツメトゲブユ(Simulium ornatum)のような吸血性双翅目害虫なども本発明の動物用外部寄生虫防除剤によって防除できる外部寄生虫として挙げられる。
Also, lice such as cow lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), cow lice (Linognathus vituli), pig lice (Haematopinus suis), pubic lice (Phthirus pubis), and head lice (Pediculus capitis), Also, lice such as Trichodectes canis, blood-sucking Diptera pests such as Tabanus trigonus, Culicoides schultzei, and Simulium ornatum can also be treated with the animal ectoparasit control method of the present invention. It is listed as an ectoparasite that can be controlled by anti-inflammatory agents.
本発明の動物用外部寄生虫防除剤は、通常使用される製剤処方に従って適当な固体担体又は液体担体を使用し、必要に応じて補助剤などと共に適当な割合に配合して溶解、懸濁、混合、含浸、吸着又は付着させ、使用目的に応じて適当な剤形、例えば液剤、乳化剤、クリーム、軟膏、懸濁剤、エアゾール剤に調製して使用すればよい。これら製剤中の有効成分の配合量は、製剤100質量部中に有効成分として0.01~80.0質量部の範囲で配合することができる。使用する固体担体又は液体担体としては、通常動物用薬剤に使用される担体を使用すればよく、対象動物への処理のし易さから液体担体を使用するのがよい。液体担体としては、例えば、メチルアルコール、エチルアルコール、イソプロピルアルコール、ターシャリーブチルアルコール、ベンジルアルコールなどのアルコール類、炭酸プロピレン、N‐メチル‐2‐ピロリドン、水などが挙げられる。必要に応じて補助剤を使用することができ、補助剤として界面活性剤、酸化防止剤、乳化剤などを使用することができ、例えば、ポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンソルビタンモノラウレート、アルキルアリルソルビタンモノラウレート、アルキルベンゼンスルホン酸塩、アルキルナフタレンスルホン酸、リグニンスルホン酸塩高級アルコール硫酸エステル塩、グリコールモノアルキルエーテル、グリコール類などの界面活性剤、モノオイレン酸ソルビタン、モノラウリン酸ソルビタン、カプリル酸モノグリセライド、カプリン酸モノグリセライド、イソステアリン酸モノグリセライド、モノカプリル酸プロピレングリコールなどの乳化剤、BHA、BHTなどの酸化防止剤が挙げられる。
The animal ectoparasiticide of the present invention can be prepared by using a suitable solid or liquid carrier in accordance with a commonly used pharmaceutical formulation, blending the agent in an appropriate proportion with an auxiliary agent as necessary, and dissolving, suspending, They may be mixed, impregnated, adsorbed or adhered, and prepared into a suitable dosage form, such as a liquid, emulsifier, cream, ointment, suspension, or aerosol, depending on the purpose of use. The amount of the active ingredient in these preparations can range from 0.01 to 80.0 parts by weight per 100 parts by weight of the preparation. As the solid carrier or liquid carrier used, carriers commonly used for veterinary drugs may be used, and liquid carriers are preferably used because they are easier to treat on target animals. Examples of the liquid carrier include alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, tertiary butyl alcohol, and benzyl alcohol, propylene carbonate, N-methyl-2-pyrrolidone, and water. Auxiliary agents can be used as necessary, and surfactants, antioxidants, emulsifiers, etc. can be used as adjuvants, such as polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monolaurate, Surfactants such as alkylaryl sorbitan monolaurate, alkylbenzene sulfonate, alkylnaphthalene sulfonic acid, lignosulfonate higher alcohol sulfate ester salt, glycol monoalkyl ether, glycols, sorbitan monooleate, sorbitan monolaurate, caprylic acid Examples include emulsifiers such as monoglyceride, capric acid monoglyceride, isostearic acid monoglyceride, and propylene glycol monocaprylate, and antioxidants such as BHA and BHT.
本発明の動物用外部寄生虫防除剤は、局所的、経口的、非経口的、及び皮下的などの所望の効果を有する経路で動物に投与すればよく、特に限定されないが、局所投与が好ましい。局所投与には、対象動物の肩甲背部の皮膚などに液状の薬剤を滴下するスポットオン処理、対象動物の背中線に沿って液状の薬剤を処理するポアオン処理、スプレーなどで液体のエアゾール薬剤を処理するスプレーオンやスプレーレース、薬浴(ディップ)、薬剤を担持させたイヤータグ又は首輪(カラー)などを用いた処理方法で投与することができる。その施用量は、対象動物の体重1kg当たり、有効成分化合物として、通常約0.1~500mg、本発明防除剤として、通常約0.01~20mlの範囲から適宜選択して処理すればよい。
The animal ectoparasiticide of the present invention may be administered to animals by a route that has the desired effect, such as locally, orally, parenterally, or subcutaneously, and is not particularly limited, but local administration is preferred. . For local administration, spot-on treatment involves dropping a liquid drug onto the skin of the dorsal region of the target animal, pour-on treatment, which involves applying a liquid drug along the back line of the target animal, and administering a liquid aerosol drug using a spray method. It can be administered by a treatment method using a spray-on, spray lace, medicinal bath (dip), ear tag or collar carrying a medicinal agent, or the like. The application amount may be appropriately selected from the range of usually about 0.1 to 500 mg of the active ingredient compound and usually about 0.01 to 20 ml of the pesticidal agent of the present invention per kg of body weight of the target animal.
また、必要に応じて他の活性成分を併用することができ、例えば、アフォキソラネル(afoxolaner)、ウミフォキソラネル(umifoxolaner)、チゴラネル(tigolaner)、フルララネル(fluralaner)、ミヴォリラネル(mivorilaner)、モドフラネル(modoflaner)、ロチラネル(lotilaner)、スロラネル(surolaner)、アルベンダゾール、カムベンダゾール、フェンベンダゾール、フルベンダゾール、メベンダゾール、オキシフェンダゾール、パラベンダゾール、チアベンダゾール、トリクラベンダゾール、アミトラズ、デミジトラズ(demiditraz)、クロルスロン、クロサンテル、オキシクロナジド、ラフォキサニド、シフェノトリン(cyphenothrin)、フルメトリン(flumethrin)、ペルメトリン(permethrin)、シロマジン(cyromazine)、デルクアンテル(derquantel)、ジアンフェネチド(diamphenetide)、ジシクラニル(dicyclanil)、ジノテフラン(dinotefuran)、イミダクロプリド(imidacloprid)、ニテンピラム(nitenpyram)、チアメトキサム(thiamethoxam)、アバメクチン(abamectin)、ドラメクチン(doramectin)、エマメクチン(emamectin)、エプリノメクチン(eprinomectin)、イベルメクチン、モキシデクチン、セラメクチン、ミルベマイシンオキシム(milbemycin oxime)、エモデプシド、エプシプランテル、フィプロニル、フルアズロン、フルヘキサホン(fluhexafon)、インドキサカルブ、レバミゾール、ルフェヌロン、メタフルミゾン、メトプレン、モネパンテル、モランテル、ニクロサミド、ニトロスカナート(nitroscanate)、ニトロキシニル、ノバルロン、オキサンテル、プラジカンテル、ピランテル、ピリプロール、ピリプロキシフェン、シサプロニル、スピノサド、スピネトラム、トリフルメゾピリムなどが挙げられる。併用にあたっては投与前に2種以上の有効成分を混合した製剤でもよく、異なる2種以上の製剤を別々に投与してもよい。
In addition, other active ingredients can be used in combination if necessary, such as afoxolaner, umifoxolaner, tigolaner, fluralaner, mivorilaner, modoflaner. ), lotilaner, surolaner, albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxifendazole, parabendazole, thiabendazole, triclabendazole, amitraz, demiditraz, clorsulon, closantel, oxyclonazide, lafoxanide, cyphenothrin, flumethrin, permethrin, cyromazine, derquantel, diamphenetide, dicyclanil, dinotefuran, imidacloprid ), nitenpyram, thiamethoxam, abamectin, doramectin, emamectin, eprinomectin, ivermectin, moxidectin, selamectin, milbemycin oxime, emodepside, epcipplantel, fipronil , fluazuron, fluhexafon, indoxacarb, levamisole, lufenuron, metaflumizone, methoprene, monepantel, morantel, niclosamide, nitroscanate, nitroxynil, novaluron, oxantel, praziquantel, pyrantel, pyriprole, pyriproxyfen, cisapronil , spinosad, spinetoram, and triflumezopyrim. When used in combination, two or more active ingredients may be mixed together before administration, or two or more different formulations may be administered separately.
本発明の動物用内部寄生虫防除剤が防除可能な内部寄生虫としては、原虫類及び蠕虫類に大別される。ヒトに寄生する原虫類としては、例えば、赤痢アメーバなどのアメーバ類(Rhizopoda)、リーシュマニア、トリパノソーマ、トリコモナスなどの鞭毛虫類(Mastigophora)、マラリア原虫、トキソプラズマなどの胞子虫類(Sporozoea)、大腸バランチジウムなどの繊毛虫類(Ciliophora)が挙げられ、ヒトに寄生する蠕虫類としては、例えば、蛔虫、アニサキス、イヌ蛔虫、毛様線虫、蟯虫、鉤虫(ズビニ鉤虫、アメリカ鉤虫、ブラジル鉤虫など)、住血線虫、顎口虫、糸状虫(フィラリア、バンクロフト糸状虫、マレー糸状虫など)、回施糸状虫(オンコセルカ)、メジナ虫、施毛虫、糞線虫などの線虫類(Nematoda)、大鉤頭虫などの鉤頭虫類(Acannthocephala)、ハリガネムシなどの鉄線虫類(Gordiacea)、チスイビルなどのヒル類(Hirudinea)、日本住血吸虫、マンソン住血吸虫、ビルハルツ住血吸虫、肝吸虫、異形吸虫、蛭状吸虫、肺吸虫などの吸虫類(Trematoda)、広節烈頭条虫、マンソン狐虫、芽殖狐虫、大複殖門条虫、テニア属条虫、(無鉤条虫、有鉤条虫、包虫(エキノコックス)など)、模様条虫、瓜実条虫、有線条虫、サル裸頭条虫、ニベリン条虫などの条虫類(Cestoda)が挙げられるが、これらに限定されるものではない。
The endoparasites that can be controlled by the animal endoparasite control agent of the present invention are broadly classified into protozoa and helminths. Protozoa that parasitic humans include, for example, amoeba (Rhizopoda) such as Entamoeba histolytica, flagellates (Mastigophora) such as Leishmania, trypanosoma, and trichomonas, sporozoa (Sporozoea) such as malaria parasites and Toxoplasma gondii, and large intestine. Ciliophora such as Balantidium are included, and helminths that parasitize humans include, for example, helminths, Anisakid, canis, hairy nematodes, pinworms, and hookworms (Zubini hookworm, American hookworm, Brazilian hookworm, etc.) , nematodes such as nematodes, gnathostomes, threadworms (filaria, Bancroft threadworms, Malayan threadworms, etc.), roundworms (Onchocerca), schizozoans, tricholates, strongyloids, etc. ), Acannthocephala (Acannthocephala), Gordiacea (Gordiacea), Hirudinea (Hirudinea), Schistosoma japonica, Schistosoma mansoni, Schistosoma bilharzia, Liver fluke, Trematodes (Trematoda) such as trematodes, leech-like trematodes, and lung flukes, tapeworms such as tapeworms, tapeworms mansoni, budworms, tapeworms great, tapeworms of the genus Taenia, tapeworms of the genus Taenia, (taenia taeniae, These include tapeworms (Cestoda) such as Taenia solium, hydatid (Echinococcus, etc.), patterned tapeworm, melid tapeworm, wire tapeworm, monkey bareheaded tapeworm, and tapeworm Nibellina. It is not limited.
ヒト以外の哺乳類又は鳥類に属する動物に寄生する原虫類としては、アピコンプレックス類(Apicomplexa)として、コクシジウム(Eimeria)、イソスポラ(Isospora)、トキソプラズマ(Toxoplasma)、ネオスポラ(Neospora)、サルコシスチス(Sarcocystis)、ベスノイチア(Besnoitia)、ハモンディア(Hammondia)、クリプトスポリジウム(Cryptosporidium)、カリオスポラ(Caryospora)などのコクシジウム類(Cocidia)、ロイコチトゾーン(Leucocytozoon)、マラリア原虫(Plasmodium)などの住血胞子虫類(Haemosporina)、ピロプラズマ(Theileria)、アナプラズマ(Anaplasma)、エペリスロゾーン(Eperythrozoon)、ヘモバルトネラ(Heamobartonella)、エールリッヒア(Rhrlichia)などのピロプラズマ類(Piroplasma)など、その他のアピコンプレックス類として、ヘパトゾーン(Hepatozoon)、ヘモグリガリナ(Haemogregarina)など、微胞子虫類(Microspora)として、エンケファリトゾーン(Encephalitozoon)、ノセマ(Nosema)など、鞭毛虫類(Mastigophora)として、トリパノソーマ(Trypanosoma)、リーシュマニア(Leishmania)などのトリパノソーマ類(Trypanosomatid)、キロマスティクス(Chilomastix)、トリコモナス(Trichomonas)、モノセルコモナス(Monocercomonas)、ヒストモナス(Histomonas)などのトリコモナス類(Trichomonadida)、ヘキサミタ(Hexamita)、ジアルジア(Giardia)、などのディプロモナス類(Diplomonadida)、肉質虫類(Sarcodina)として、赤痢アメーバ(Entamoeba)などのアメーバ類など、繊毛虫類(Ciliophora)として、大腸バランチジウム(Balantidium)、バクストネラ(Buxtonella)、ルーメン内繊毛虫(Entodinium)など、
Protozoa that parasitize animals belonging to mammals or birds other than humans include coccidia (Eimeria), Isospora (Isospora), Toxoplasma (Toxoplasma), Neospora (Neospora), Sarcocystis (Sarcocystis), Coccidia such as Besnoitia, Hammondia, Cryptosporidium, and Caryospora; Haemosporina such as Leucocytozoon and Plasmodium; ), Piroplasma such as Theileria, Anaplasma, Eperythrozoon, Heamobartonella, Rhrlichia, and other apicomplexans such as Hepatozoon. , Haemogregarina, Microspora, Encephalitozoon, Nosema, etc. Flagellates, Mastigophora, Trypanosoma, Leishmania, etc. Trichomonads such as Trypanosomatid, Chilomastix, Trichomonas, Monocercomonas, Histomonas, Diplomonas such as Hexamita, Giardia, etc. Diplomonadida, Sarcodina, amoebas such as Entamoeba, Ciliophora, Balantidium, Buxtonella, Entodinium. Such,
ヒト以外の哺乳類又は鳥類に属する動物に寄生する蠕虫類としては、例えば、線虫類として、豚蛔虫(Ascaris)、犬蛔虫及び猫蛔虫(Toxocara)、犬小蛔虫(Toxascaris)、馬蛔虫(Parascaris)、鶏蛔虫(Ascaridia)、鶏盲腸虫(Heterakis)、アニサキス(Anisakis)などの回虫類(Ascarida)、馬蟯虫(Oxyuris)、ウサギ蟯虫(Passalurus)などの蟯虫類(Oxyurida)、馬円虫(Strongylus)、捻転胃虫(Haemonchus)、牛のオクテルターグ胃虫(Ostertagia)、蛇状毛様線虫(Trichostrongylus)、点状毛様線虫(Cooperia)、細頸毛様線虫(Nematodirus)、紅色毛様線虫(Hystrongylus)、牛腸結節虫(Oesophagostomum)、大口腸線虫(Chabertia)、犬鉤虫(Ancylostoma)、狭頭鉤虫(Uncinaria)、アメリカ鉤虫(Necator)、牛鉤虫(Bunostomum)、牛肺虫(Dictyocaulus)、豚肺虫(Metastrongylus)、犬肺虫(Filaroides)、猫肺虫(Aelurostrongulus)、広東住血線虫(Angiostrongylus)、気管開嘴虫(Syngamus)、豚腎虫(Stephanurus)などの円虫類(Strongylida)、糞線虫(Strongyloides)、ミクロネマ(Micronema)などの桿線虫類(Rhabditida)、ロデシア眼虫(Thelazia)、マンソン眼虫(Oxyspirura)、血色食道虫(Spirocerca)、美麗食道虫(Gongylonema)、大口馬胃虫(Draschia)、小口馬胃虫(Habronema)、類円豚胃虫(Ascarops)、猫胃虫(Physaloptera)、有棘顎口虫(Gnathostoma)などの旋尾線虫類(Spirurida)、犬糸条虫(Dirofilaria)、馬糸条虫(Setaria)、ディペタロネマ(Dipetalonema)、多乳頭糸状虫(Parafilaria)、頸部糸状虫(Onchocerca)などの糸状虫類(Filariida)、パラフィラリア(Parafilaria)、沖縄糸状虫(Stephanofilaria)、犬鞭虫(Trichuris)、牛毛細線虫(Capillaria)、ネズミ膀胱毛細線虫(Trichosomoides)、旋毛虫(Trichinella)、腎虫(Dioctophyma)などのエノプリダ類(Enoplida)など、
Examples of helminths that parasitize animals belonging to mammals or birds other than humans include nematodes such as Ascaris, Toxocara, Toxascaris, and Parascaris. ), roundworms (Ascarida) such as Ascaridia, Heterakis and Anisakis, Oxyurida such as Oxyuris and Passalurus, strongyles ( strongylus), Haemonchus, bovine Ostertagia, Trichostrongylus, Cooperia, Nematodirus, red Hystrongylus, Oesophagostomum, Chabertia, Ancylostoma, Uncinaria, Necator, Bunostomum, Bovine Lungworm (Dictyocaulus), pig lungworm (Metastrongylus), dog lungworm (Filaroides), cat lungworm (Aelurostrongulus), Cantonese schistosome (Angiostrongylus), tracheostomy beak (Syngamus), pig kidneyworm (Stephanurus), etc. Strongylida, Strongyloides, Micronema and other rod nematodes, Thelazia, Oxyspirura, Spirocerca, Beautiful Circulating tails of esophagus (Gongylonema), large-mouthed horse stomach worm (Draschia), small-mouthed horse stomach worm (Habronema), ascarops (Ascarops), cat stomach worm (Physaloptera), gnathostoma (Gnathostoma), etc. Filariida, such as Spirurida, Dirofilaria, Setaria, Dipetalonema, Parafilaria, Onchocerca, etc. ), Parafilaria, Stephanofilaria, Trichuris, Capillaria, Trichosomoides, Trichinella, Dioctophyma, etc. Enoplida, etc.
吸虫類として、肝蛭(Fasciola)、肥大吸虫(Fasciolopsis)などの肝蛭類(Fasciolata)、平腹双口吸虫(Homalogaster)などの双口吸虫類(Paramphistomatidae)、膵蛭(Eurytrema)、槍形吸虫(Dicrocoelium)などの二腔吸虫類(Dicrocoelata)、壺形吸虫(Pharyngostomum)、アラリア(Alaria)などの重口吸虫類(Diplostomata)、浅田棘口吸虫(Echinostoma)、エキノカスムス(Echinochasmus)、などの棘口吸虫類(Echinostomata)、肺吸虫(Paragonimus)、サケ中毒吸虫(Nanophyetus)などの住胞吸虫類(Troglotrematoidea)、肝吸虫(Clonorchis)などの後睾吸虫類(Opisthorchiida)、異形吸虫(Heterophyes)、横河吸虫(Metagonimus)などの異形吸虫類(Heterophyida)、鶏卵吸虫(Prosthogonimus)などの斜睾吸虫類(Plagiorchiida)、日本住血吸虫(Schistoma)などの住血吸虫類(Schistosoma)など、条虫類として、日本海裂頭条虫(Diphyllobothrium)、マンソン裂頭条虫(Spirometra)などの擬葉類(Pseudophylidea)、葉状条虫(Anoplocephara)、乳頭条虫(Paranoplocephala)、ベネデン条虫(Moniezia)、犬条虫(Dipylidium)、有線条虫(Mesocestoides)、豆状条虫、胞状条虫(Tenia)、猫条虫(Hydatigera)、多頭条虫(Multiceps)、単包条虫(Echinococcus)、多包条虫(Echinococcus)、有鉤条虫(Taenia)、無鉤条虫(Taeniarhynchus)、縮小条虫(Hymenolepis)、小形条虫(Vampirolepis)、方形条虫(Raillietina)、楔形条虫(Amoebotaenia)などの円葉類(Cyclophyllidea)など、鉤頭虫類として、犬鉤頭虫(Macracanthorhynchus)、鎖状鉤頭虫(Moniliformis)など、舌虫類として、犬舌虫(Linguatula)など、その他種々の寄生虫が挙げられるが、これらに限定されるものではない。
Flukes include Fasciolata, such as Fasciola and Fasciolopsis, Paramphistomatidae, such as Homalogaster, Eurytrema, and lanceolates. Diplocoelata such as Dicrocoelium, Pharyngostomum, Diplostomata such as Alaria, Echinostoma, Echinochasmus, etc. Troglotrematoidea such as Echinostomata, Paragonimus, and Nanophyetus; Opisthorchiida such as Clonorchis; Heterophyes. , Heterophyida such as Metagonimus, Plagiorchiida such as Prosthogonimus, Schistosoma such as Schistoma, and tapeworms. Pseudophylidea such as Diphyllobothrium, Spirometra, Anoplocephara, Paranoplocephala, Moniezia, Dog tapeworms (Dipylidium), wired tapeworms (Mesocestoides), legume-like tapeworms, hydatid tapeworms (Tenia), cat tapeworms (Hydatigera), multicephalic tapeworms (Multiceps), monocystic tapeworms (Echinococcus), polycystic tapeworms Echinococcus, Taenia, Taeniarhynchus, Hymenolepis, Vampirolepis, Raillietina, Amoebotaenia, etc. Cyclophyllidea, etc., Macracanthorhynchus, Moniliformis, etc., and tongue worms, such as Linguatula, and various other parasitic organisms. Examples include, but are not limited to, insects.
さらに蠕虫類として別呼称では、例えば、線虫類のエノプリダ属(Enoplida)として、鞭虫種(Trichuris spp.)、カピラリア種(Capillaria spp.)、トリコモソイデス種(Trichomosoides spp.)、トリキネラ種(Trichinella spp.)などが挙げられ、ラブディティア属(Rhabditia)として、例えば、ミクロネマ種(Micronema spp.)及びストロンギロイデス種(Strongyloides spp.)などが挙げられ、ストロンギリダ属(Strongylida)として、例えば、ストロニルス種(Stronylus spp.)、トリオドントホルス種(Triodontophorus spp.)、オエソファゴドントウス種(Oesophagodontus spp.)、トリコネマ種(Trichonema spp.)、ジアロセファルス種(Gyalocephalus spp.)、シリンドロフアリンクス種(Cylindropharynx spp.)、ポテリオストムム種(Poteriostomum spp.)、シクロコセルクス種(Cyclococercus spp.)、シリコステファヌス種(Cylicostephanus spp.)、オエソファゴストムム種(Oesophagostomum spp.)、カベルチア種(Chabertia spp.)、ステファヌルス種(Stephanurus spp.)、鉤虫種(Ancylostoma spp.)、有鉤虫種(Uncinaria spp.)、ブノストムム種(Bunostomum spp.)、グロボセファルス種(Globocephalus spp.)、シンガムス種(Syngamus spp.)、シアトストマ種(Cyathostoma spp.)、メタストロンギルス種(Metastrongylus spp.)、ジクチオカウルス種(Dictyocaulus spp.)、ムエレリウス種(Muellerius spp.)、プロトストロンギルス種(Protostrongylus spp.)、ネオストロンギルス種(Neostrongylus spp.)、シストカウルス種(Cystocaulus spp.)、ニューモストロンギルス種(Pneumostrongylus spp.)、スピコカウルス種(Spicocaulus spp.)、エラフォストロンギルス種(Elaphostrongylus spp.)、パレラフォストロンギルス種(Parelaphostrongylus spp.)、クレノソマ種(Crenosoma spp.)、パラクレノソマ種(Paracrenosoma spp.)、アンジオストロンギルス種(Angiostrongylus spp.)、アエルロストロンギルス種(Aelurostrongylus spp.)、フィラロイデス種(Filaroides spp.)、パラフィラロイデス種(Parafilaroides spp.)、トリコストロンギルス種(Trichostrongylus spp.)、ヘモンクス種(Haemonchus spp.)、オステルタギア種(Ostertagia spp.)、マーシャラギア種(Marshallagia spp.)、クーペリア種(Cooperia spp.)、ネマトディルス種(Nematodirus spp.)、ヒオストロンギルス種(Hyostrongylus spp.)、オベリスコイデス種(Obeliscoides spp.)、アミドストムム種(Amidostomum spp.)及びオルラヌス種(Ollulanus spp.)などが挙げられ、
Other names for helminths include, for example, the nematode genus Enoplida, Trichuris spp., Capillaria spp., Trichomosoides spp., Trichinella spp. spp.), examples of the genus Rhabditia include Micronema spp. and Strongyloides spp., and examples of the genus Strongylida include, for example, Stronylus. Species (Stronylus spp.), Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindrophorahynchus spp. Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Chabertia spp., Stephanus Stephanurus spp., Ancylostoma spp., Uncinaria spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp. ), Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Paraphylloides spp. (Parafilaroides spp.), Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Marshallagia spp., Cooperia spp., Nematodilus Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp. and Ollulanus spp.
蟯虫属(Oxyurida)として、例えば、オキシウリス種(Oxyuris spp.)、エンテロビウス種(Enterobius spp.)、パサルルス種(Passalurus spp.)、サイファシア種(Syphacia spp.)、アスピキュルリス種(Aspiculuris spp.)及びヘテラキス種(Heterakis spp.)などが挙げられ、蛔虫科(Ascaridia)として、例えば、アスカリス種(Ascaris spp.)、トキサスカリス種(Toxascaris spp.)、トキソカラ種(Toxocara spp.)、パラスカリス種(Parascaris spp.)、アニサキス種(Anisakis spp.)及びアスカリディア種(Ascaridia spp.)などが挙げられ、スピルリダ属(Spiruride)として、例えば、顎口虫種(Gnathosma spp.)、フィサロプテラ種(Physaloptera spp.)、テラジア種(Thelazia spp.)、ゴンギロネマ種(Gongylonema spp.)、ハブロネマ種(Habronema spp.)、パラグロネマ種(Parabronema spp.)、ドラシア種(Draschia spp.)及びドラクンクルス種(Dracunculus spp.)などが挙げられ、フィラリイダ属(Filariida)として、例えば、ステファノフィラリア種(Stephanofilaria spp.)、パラフィラリア種(Parafilaria spp.)、セタリア種(Setaria spp.)、ロア種(Loa spp.)、デイロフィラリア種(Dirofilaria spp.)、リトモソイデス種(Litomosoides spp.)、ブルギア種(Brugia spp.)、ウチエレリア種(Wuchereria spp.)、オンコセルカ種(Onchocerca spp.)などが挙げられ、
As the pinworm genus (Oxyurida), for example, Oxyuris spp., Enterobius spp., Passalurus spp., Syphacia spp., Aspiculuris spp. and Heterakis spp., and Ascaridiae include, for example, Ascaris spp., Toxascaris spp., Toxocara spp., Parascaris spp. spp.), Anisakis spp., and Ascaridia spp.; examples of the Spiruride genus include Gnathosma spp., Physaloptera spp. ), Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp., etc. Examples of the genus Filariida include Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., and Deirofilaria. Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp., etc.
鉤頭虫類(Acanthocephala)として、例えば、フィリコリス種(Filicollis spp.)、モニリホルミス種(Moniliformis spp.)、マクラカントルヒンクス種(Macracanthorhynchus spp.)、プロステノルチス種(Prosthenorchis spp.)などが挙げられ、吸虫類の単生類(Monogenea)の亜綱として、例えば、ジロダクチルス種(Gyrodactylus spp.)、ダクチロギルス種(Dactylogyrusspp.)及びポリストマ種(Polystoma spp.)などが挙げられ、二生類の亜綱として、例えば、ディプロストムム種(Diplostomum spp.)、ポストディプロストムム種(Posthodiplostomum spp.)、住血吸虫種(Schistosomaspp.)、トリコビルハルジア種(Trichobilharzia spp.)、オルニトビルハルジア種(Ornithbilharzia spp.)、オーストロビルハルジア種(Austrobilharzia spp.)、ジガントビルハルジア種(Gigantobilharziaspp.)、ロイコクロリジウム種(Leucochloridium spp.)、ブラキライマ種(Brachylaima spp.)、棘口吸虫種(Echinostoma spp.)、エノキパリフィウム種(Echinoparyphium spp.)、エキノカスムス種(Echinochasmus spp.)、ヒポデレウム種(Hypoderaeum spp.)、ファスキオラ種(Fasciola spp.)、ファスキオリデス種(Fasciolides spp.)、肥大吸虫種(Fasciolopsis spp.)、シクロコエルム種(Cyclocoelum spp.)、チフロコエルム種(Typhlocoelum spp.)、パラムフィストムム種(Paramphistomum spp.)、カリコフオロン種(Calicophoron spp.)、コチロホロン種(Cotylophoron spp.)、ジガントコチレ種(Gigantcotyle spp.)、フィスコエデリウム種(Fischoederius spp.)、ガストロチラクス種(Gastrothylacus spp.)、ノトコチルス種(Notocotylus spp.)、カタトロピス種(Catatropis spp.)、プラジオルキス種(Plagiorchis spp.)、プロストゴニムス種(Prosthogonimus spp.)、ジクロコエリウム種(Dicrocoelium spp.)、ユーリトレマ種(Eurytrema spp.)、トログロトレマ種(Troglotrema spp.)、肺吸虫種(Paragonimus spp.)、コリリクルム種(Collyriclum spp.)、ナノフィエトウス種(Nanophyetus spp.)、オピストルキス種(Opisthorchis spp.)、クロノルキス種(Clonorchis spp.)、メトルキス種(Metorchis spp.)、異形吸虫種(Heterophyes spp.)及びメタゴニムス種(Metagonimus spp.)などが挙げられ、
Examples of Acanthocephala include Filicollis spp., Moniliformis spp., Macracanthorhynchus spp., Prosthenorchis spp. Subclasses of Monogenea of trematodes include, for example, Gyrodactylus spp., Dactylogyrusspp., and Polystoma spp., and subclasses of Digenea include, for example. , Diplostomum spp., Posthodiplostomum spp., Schistosomaspp., Trichobilharzia spp., Ornithbilharzia spp. ), Austrobilharzia spp., Gigantobilharziaspp., Leucochloridium spp., Brachylaima spp., Echinostoma spp. spp.), Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fasciolides spp., Hypertrophic fluke spp. (Fasciolopsis spp.), Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp. (Gigantcotyle spp.), Fischoederius spp., Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum spp., Nano Nanophyetus spp., Opisthorchis spp., Clonorchis spp., Metorchis spp., Heterophyes spp., Metagonimus spp., etc. are mentioned,
条虫類の擬葉目(Pseudophyllidea)として、例えば、裂頭条虫属種(Diphyllobothrium spp.)、スピロメトラ種(Spirometra spp.)、シストセファルス種(Schistocephalus spp.)、リグラ条虫種(Ligula spp.)、ボトリジウム種(Bothridium spp.)及び大複殖門条虫種(Diplogonoporus spp.)が挙げられ、円葉目(Cyclophyllidea)として、例えば、メソセストイデス種(Mesocestoides spp.)、裸頭条虫種(Anoplocephala spp.)、パラノプロセフアラ種(Paranoplocehala spp.)、モニエジア種(Moniezia spp.)、チサノソムサ種(Thysanosomsa spp.)、チサニエジア種(Thysaniezia spp.)、アビテリナ種(Avitellina spp.)、ステレシア種(Stilesia spp.)、シトテニア種(Cittotaenia spp.)、アンディラ種(Andyra spp.)、ベルチエラ種(Bertiella spp.)、チーニア種(taenia spp.)エキノコッカス種(Echinococcus spp.)、ヒダチゲラ種(Hydatigera spp.)、ダヴェネア種(Davainea spp.)、方形条虫種(Raillietina spp.)、模様条虫種(Hymenolepis spp.)、エキノレビス種(Echinolepis spp.)、エキノコチレ種(Echinocotyle spp.)、ジオルキス種(Diorchisspp.)、ジピリジウム種(Dipylidium spp.)、ジョイオイキシェラ種(Joyeuxiella spp.)及びジプロピリジウム種(Diplopylidium spp.)などの種に属する寄生虫や、その他鉤頭虫類、舌虫類に属する種々の寄生虫が挙げられるが、これらに限定されるものではない。
Examples of tapeworms in the order Pseudophyllidea include Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., and Ligula spp. spp.), Bothridium spp., and Diplogonoporus spp., and in the Cyclophyllidea order, for example, Mesocestoides spp., Nachocephalic tapeworms. species (Anoplocephala spp.), Paranoplocehala spp., Moniezia spp., Thysanosomsa spp., Thysaniezia spp., Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., taenia spp., Echinococcus spp., Echinococcus spp. (Hydatigera spp.), Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp. Parasites belonging to species such as Diorchisspp., Dipylidium spp., Joyeuxiella spp., and Diplopylidium spp., as well as other talcocephaloids and tongue worms. Examples include, but are not limited to, various parasites belonging to the genus.
本発明の動物用内部寄生虫防除剤は、中間宿主及び終宿主の体内に生息する寄生虫だけでなく、保虫宿主生体内の寄生虫の防除にも効果を発現する。また、本発明の一般式(1)で表される化合物は、寄生虫のすべての発育段階に於いて防除効果を発現する。例えば、原虫類では嚢子、前被嚢型、栄養型或いは無性生殖期の分裂体、アメーバ体、有性生殖期の生殖母体、生殖体、融合体、胞子体などである。線虫類では、卵、幼虫、成虫である。さらに、本発明に係わる化合物は、生体内の寄生虫を駆除するだけでなく、感染経路となる環境中に施用する事で予防的に寄生虫の感染を防ぐことが可能である。例えば、畑、公園の土壌からの土壌伝播感染、河川、湖沼、湿地、水田などの水系からの経皮感染、イヌ、ネコなどの動物の糞からの経口的感染、海水魚、淡水魚、甲殻類、貝類、家畜の生肉などからの経口的感染、蚊、アブ、ハエ、ゴキブリ、ダニ、ノミ、シラミ、サシガメ、ツツガムシなどからの感染などを未然に予防することが可能である。
The animal endoparasite control agent of the present invention is effective in controlling not only parasites living in the bodies of intermediate hosts and definitive hosts, but also parasites in the host organism. Furthermore, the compound represented by the general formula (1) of the present invention exhibits a controlling effect on parasites at all stages of development. For example, in protozoa, these include cysts, pretunicate types, trophozoites, meristems in the asexual stage, amoeboid bodies, gametocytes, gametes, fusion bodies, and sporophytes in the sexual stage. In nematodes, they are eggs, larvae, and adults. Furthermore, the compound according to the present invention not only exterminates parasites within a living body, but also prevents parasite infection by applying it to the environment, which is a route of infection. For example, soil-transmitted infection from soil in fields and parks, percutaneous infection from water systems such as rivers, lakes, wetlands, and rice fields, oral infection from feces of animals such as dogs and cats, saltwater fish, freshwater fish, and crustaceans. It is possible to prevent oral infections from shellfish, raw livestock meat, etc., and infections from mosquitoes, horseflies, flies, cockroaches, ticks, fleas, lice, assassin bugs, chiggers, etc.
本発明の動物用内部寄生虫防除剤は、ヒト、ヒト以外の哺乳類又は鳥類に属する動物の医薬品として寄生虫症の治療又は予防の目的で投与することが可能である。投与方法は、経口投与又は非経口投与のいずれも可能である。経口投与の場合は、カプセル剤、錠剤、丸剤、粉剤、顆粒剤、細粒剤、散剤、シロップ、腸溶剤、懸濁剤、ペースト或いは動物用の液体飲料又は飼料中に配合することにより、投与することが可能である。非経口投与の場合は、注射剤、点滴剤、座薬、乳剤、懸濁剤、滴下剤、軟膏剤、クリーム剤、液剤、ローション剤、スプレー剤、エアゾル剤、パップ剤、テープ剤として、粘膜又は経皮吸収が維持できるような剤型で投与される。
The animal endoparasite control agent of the present invention can be administered to humans, non-human mammals, or birds as a pharmaceutical for the purpose of treating or preventing parasitic diseases. The administration method can be either oral administration or parenteral administration. For oral administration, by incorporating into capsules, tablets, pills, powders, granules, fine granules, powders, syrups, enteric-coated agents, suspensions, pastes, or liquid drinks or feed for animals. It is possible to administer For parenteral administration, injections, drops, suppositories, emulsions, suspensions, drops, ointments, creams, liquids, lotions, sprays, aerosols, poultices, and tapes can be administered to mucous membranes or It is administered in a dosage form that maintains percutaneous absorption.
本発明の動物用内部寄生虫防除剤をヒト、ヒト以外の哺乳類又は鳥類に属する動物の医薬品として使用する場合、有効成分の最適量(有効量)は治療又は予防の別、感染寄生虫の種類、感染の型及び程度、剤型などにより変化するが、一般に経口投与の場合は、1日当たり約0.0001から10000mg/kg体重の範囲である。非経口投与の場合は、1日当たり約0.0001から10000mg/kg体重の範囲であり、単回或いは分割して投与される。
When the animal endoparasite control agent of the present invention is used as a drug for humans, non-human mammals, or birds, the optimal amount (effective amount) of the active ingredient should be determined depending on the type of infecting parasite, whether for treatment or prevention. The dosage varies depending on the type and degree of infection, dosage form, etc., but in general, in the case of oral administration, it is in the range of about 0.0001 to 10,000 mg/kg body weight per day. For parenteral administration, the dose ranges from about 0.0001 to 10,000 mg/kg body weight per day, administered in a single dose or in divided doses.
本発明の動物用内部寄生虫防除剤中の有効成分の濃度は、一般に0.001~100質量%、好ましくは0.001~99%、さらに好ましくは0.005~20質量%程度である。本発明の動物用内部寄生虫防除剤は、そのまま投与する組成物でもよく、使用時に適当な濃度に希釈して使用される高濃度な組成物でもよい。
The concentration of the active ingredient in the animal internal parasite control agent of the present invention is generally about 0.001 to 100% by mass, preferably about 0.001 to 99%, and more preferably about 0.005 to 20% by mass. The animal endoparasite control agent of the present invention may be a composition to be administered as it is, or may be a highly concentrated composition that is diluted to an appropriate concentration before use.
また、本発明の動物用内部寄生虫防除剤の効果を補強又は補完する目的で必要に応じて前記の他の活性成分を併用することもできる。併用にあたっては投与前に2種以上の有効成分を混合した製剤でもよく、異なる2種以上の製剤を別々に投与してもよい。
Furthermore, the other active ingredients described above can be used in combination as necessary for the purpose of reinforcing or supplementing the effects of the animal endoparasite control agent of the present invention. When used in combination, two or more active ingredients may be mixed together before administration, or two or more different formulations may be administered separately.
以下に本発明の代表的な実施例を例示するが、本発明はこれらに限定されるものではない。
Representative examples of the present invention are illustrated below, but the present invention is not limited thereto.
製造実施例1
N‐(4‐フルオロフェニル)‐4‐ヒドロキシ‐2‐オキソ‐1‐(4‐(トリフルオロメチル)ベンジル)‐2,5,6,7‐テトラヒドロ‐1H‐アゼピン‐3‐カルボキサミド(化合物番号1‐52)の製造
Manufacturing example 1
N-(4-fluorophenyl)-4-hydroxy-2-oxo-1-(4-(trifluoromethyl)benzyl)-2,5,6,7-tetrahydro-1H-azepine-3-carboxamide (compound no. 1-52) Production
N‐(4‐フルオロフェニル)‐4‐ヒドロキシ‐2‐オキソ‐1‐(4‐(トリフルオロメチル)ベンジル)‐2,5,6,7‐テトラヒドロ‐1H‐アゼピン‐3‐カルボキサミド(化合物番号1‐52)の製造
N-(4-fluorophenyl)-4-hydroxy-2-oxo-1-(4-(trifluoromethyl)benzyl)-2,5,6,7-tetrahydro-1H-azepine-3-carboxamide (compound no. 1-52) Production
1‐(4‐(トリフルオロメチル)ベンジル)アゼパン‐2,4‐ジオン(280mg,0.982mmol)をN,N‐ジメチルアセトアミド(2mL)に溶解させ、イソシアン酸‐4‐フルオロフェニル(202mg,1.47mmol)、水素化ナトリウム(51.0mg,1.28mmol)を室温で加えた。反応液を室温で1時間撹拌した後、飽和塩化アンモニウム水溶液を加えた。その後、反応液に1N塩酸水溶液を加え、酢酸エチルで3回抽出した。有機層を減圧濃縮することにより得られた粗生成物をシリカゲルカラムクロマトグラフィーで精製することにより、N‐(4‐フルオロフェニル)‐4‐ヒドロキシ‐2‐オキソ‐1‐(4‐(トリフルオロメチル)ベンジル)‐2,5,6,7‐テトラヒドロ‐1H‐アゼピン‐3‐カルボキサミド(61.0mg,0.144mmol)を得た。
収率:15%
物性:1H‐NMR(CDCl3):δ 16.0(s,1H),10.6 (s,1H),7.63(d,2H),7.53-7.48(m,2H),7.45(d,2H),7.04(t,2H),4.77(s,2H),3.43(t,2H),2.55(t,2H),2.07-1.95(m,2H) 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione (280 mg, 0.982 mmol) was dissolved in N,N-dimethylacetamide (2 mL), and 4-fluorophenyl isocyanate (202 mg, 1.47 mmol) and sodium hydride (51.0 mg, 1.28 mmol) were added at room temperature. After stirring the reaction solution at room temperature for 1 hour, a saturated aqueous ammonium chloride solution was added. Thereafter, 1N aqueous hydrochloric acid solution was added to the reaction solution, and the mixture was extracted three times with ethyl acetate. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain N-(4-fluorophenyl)-4-hydroxy-2-oxo-1-(4-(trifluorophenyl) methyl)benzyl)-2,5,6,7-tetrahydro-1H-azepine-3-carboxamide (61.0 mg, 0.144 mmol) was obtained.
Yield: 15%
Physical properties: 1 H-NMR (CDCl 3 ): δ 16.0 (s, 1H), 10.6 (s, 1H), 7.63 (d, 2H), 7.53-7.48 (m, 2H ), 7.45 (d, 2H), 7.04 (t, 2H), 4.77 (s, 2H), 3.43 (t, 2H), 2.55 (t, 2H), 2.07 -1.95 (m, 2H)
収率:15%
物性:1H‐NMR(CDCl3):δ 16.0(s,1H),10.6 (s,1H),7.63(d,2H),7.53-7.48(m,2H),7.45(d,2H),7.04(t,2H),4.77(s,2H),3.43(t,2H),2.55(t,2H),2.07-1.95(m,2H) 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione (280 mg, 0.982 mmol) was dissolved in N,N-dimethylacetamide (2 mL), and 4-fluorophenyl isocyanate (202 mg, 1.47 mmol) and sodium hydride (51.0 mg, 1.28 mmol) were added at room temperature. After stirring the reaction solution at room temperature for 1 hour, a saturated aqueous ammonium chloride solution was added. Thereafter, 1N aqueous hydrochloric acid solution was added to the reaction solution, and the mixture was extracted three times with ethyl acetate. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain N-(4-fluorophenyl)-4-hydroxy-2-oxo-1-(4-(trifluorophenyl) methyl)benzyl)-2,5,6,7-tetrahydro-1H-azepine-3-carboxamide (61.0 mg, 0.144 mmol) was obtained.
Yield: 15%
Physical properties: 1 H-NMR (CDCl 3 ): δ 16.0 (s, 1H), 10.6 (s, 1H), 7.63 (d, 2H), 7.53-7.48 (m, 2H ), 7.45 (d, 2H), 7.04 (t, 2H), 4.77 (s, 2H), 3.43 (t, 2H), 2.55 (t, 2H), 2.07 -1.95 (m, 2H)
製造実施例2
N‐(5‐フルオロピリジン‐2‐イル)‐4‐ヒドロキシ‐2‐オキソ‐1‐(4‐(トリフルオロメチル)ベンジル)‐2,5,6,7‐テトラヒドロ‐1H‐アゼピン‐3‐カルボキサミド(化合物番号1‐55)の製造
Manufacturing example 2
N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1-(4-(trifluoromethyl)benzyl)-2,5,6,7-tetrahydro-1H-azepine-3- Production of carboxamide (compound number 1-55)
N‐(5‐フルオロピリジン‐2‐イル)‐4‐ヒドロキシ‐2‐オキソ‐1‐(4‐(トリフルオロメチル)ベンジル)‐2,5,6,7‐テトラヒドロ‐1H‐アゼピン‐3‐カルボキサミド(化合物番号1‐55)の製造
N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1-(4-(trifluoromethyl)benzyl)-2,5,6,7-tetrahydro-1H-azepine-3- Production of carboxamide (compound number 1-55)
5‐フルオロ‐2‐アミノピリジン(235mg,2.10mmol)をN,N‐ジメチルアセトアミド(15.0mL)に溶解させ、トリエチルアミン(585μL,4.20mmol)、カルボニルジイミダゾール(372mg,2.31mmol)を室温で加えた。反応液を室温で2時間撹拌した後、1‐(4‐(トリフルオロメチル)ベンジル)アゼパン‐2,4‐ジオン(300mg,1.05mmol)、DBU(300μL,2.10mmol)を加えた。反応液を室温で15時間撹拌した後、1N塩酸水溶液を加え、酢酸エチルで3回抽出した。有機層を減圧濃縮することにより得られた粗生成物をシリカゲルカラムクロマトグラフィーで精製することにより、N‐(5‐フルオロピリジン‐2‐イル)‐4‐ヒドロキシ‐2‐オキソ‐1‐(4‐(トリフルオロメチル)ベンジル)‐2,5,6,7‐テトラヒドロ‐1H‐アゼピン‐3‐カルボキサミド(52.0mg,0.123mmol)を得た。
収率:12%
物性:1H‐NMR(CDCl3):δ 15.7(s,1H),11.0(s,1H),8.20(d,1H),8.13(dd,1H),7.62(d,2H),7.50-7.39(m,3H),4.78(s,2H),3.41(t,2H),2.55(t,2H),2.03-1.94(m,2H) 5-fluoro-2-aminopyridine (235 mg, 2.10 mmol) was dissolved in N,N-dimethylacetamide (15.0 mL), triethylamine (585 μL, 4.20 mmol), carbonyldiimidazole (372 mg, 2.31 mmol) was added at room temperature. After stirring the reaction solution at room temperature for 2 hours, 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione (300 mg, 1.05 mmol) and DBU (300 μL, 2.10 mmol) were added. After stirring the reaction solution at room temperature for 15 hours, 1N aqueous hydrochloric acid solution was added, and the mixture was extracted three times with ethyl acetate. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1-(4 -(trifluoromethyl)benzyl)-2,5,6,7-tetrahydro-1H-azepine-3-carboxamide (52.0 mg, 0.123 mmol) was obtained.
Yield: 12%
Physical properties: 1 H-NMR (CDCl 3 ): δ 15.7 (s, 1H), 11.0 (s, 1H), 8.20 (d, 1H), 8.13 (dd, 1H), 7. 62 (d, 2H), 7.50-7.39 (m, 3H), 4.78 (s, 2H), 3.41 (t, 2H), 2.55 (t, 2H), 2.03 -1.94 (m, 2H)
収率:12%
物性:1H‐NMR(CDCl3):δ 15.7(s,1H),11.0(s,1H),8.20(d,1H),8.13(dd,1H),7.62(d,2H),7.50-7.39(m,3H),4.78(s,2H),3.41(t,2H),2.55(t,2H),2.03-1.94(m,2H) 5-fluoro-2-aminopyridine (235 mg, 2.10 mmol) was dissolved in N,N-dimethylacetamide (15.0 mL), triethylamine (585 μL, 4.20 mmol), carbonyldiimidazole (372 mg, 2.31 mmol) was added at room temperature. After stirring the reaction solution at room temperature for 2 hours, 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione (300 mg, 1.05 mmol) and DBU (300 μL, 2.10 mmol) were added. After stirring the reaction solution at room temperature for 15 hours, 1N aqueous hydrochloric acid solution was added, and the mixture was extracted three times with ethyl acetate. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain N-(5-fluoropyridin-2-yl)-4-hydroxy-2-oxo-1-(4 -(trifluoromethyl)benzyl)-2,5,6,7-tetrahydro-1H-azepine-3-carboxamide (52.0 mg, 0.123 mmol) was obtained.
Yield: 12%
Physical properties: 1 H-NMR (CDCl 3 ): δ 15.7 (s, 1H), 11.0 (s, 1H), 8.20 (d, 1H), 8.13 (dd, 1H), 7. 62 (d, 2H), 7.50-7.39 (m, 3H), 4.78 (s, 2H), 3.41 (t, 2H), 2.55 (t, 2H), 2.03 -1.94 (m, 2H)
製造実施例3
N‐(4‐フルオロフェニル)‐4‐ヒドロキシ‐2‐オキソ‐1‐(4‐(トリフルオロメチル)フェニル)‐2,5,6,7‐テトラヒドロ‐1H‐アゼピン‐3‐カルボキサミド(化合物番号1‐20)の製造
Manufacturing example 3
N-(4-fluorophenyl)-4-hydroxy-2-oxo-1-(4-(trifluoromethyl)phenyl)-2,5,6,7-tetrahydro-1H-azepine-3-carboxamide (compound no. 1-20) Manufacturing
N‐(4‐フルオロフェニル)‐4‐ヒドロキシ‐2‐オキソ‐1‐(4‐(トリフルオロメチル)フェニル)‐2,5,6,7‐テトラヒドロ‐1H‐アゼピン‐3‐カルボキサミド(化合物番号1‐20)の製造
N-(4-fluorophenyl)-4-hydroxy-2-oxo-1-(4-(trifluoromethyl)phenyl)-2,5,6,7-tetrahydro-1H-azepine-3-carboxamide (compound no. 1-20) Manufacturing
1‐(4‐(トリフルオロメチル)フェニル)アゼパン‐2,4‐ジオン(300mg,1.11mmol)をN,N‐ジメチルアセトアミド(5mL)に溶解させ、イソシアン酸‐4‐フルオロフェニル(265mg,1.94mmol)、水素化ナトリウム(67.1mg,1.68mmol)を室温で加えた。反応液を室温で1時間撹拌した後、飽和塩化アンモニウム水溶液を加えた。その後、1N塩酸水溶液を加え、酢酸エチルで3回抽出した。有機層を減圧濃縮することにより得られた粗生成物をシリカゲルカラムクロマトグラフィーで精製することにより、N‐(4‐フルオロフェニル)‐4‐ヒドロキシ‐2‐オキソ‐1‐(4‐(トリフルオロメチル)フェニル)‐2,5,6,7‐テトラヒドロ‐1H‐アゼピン‐3‐カルボキサミド(215mg,0.526mmol)を得た。
収率:47%
物性:融点112-113℃ 1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione (300 mg, 1.11 mmol) was dissolved in N,N-dimethylacetamide (5 mL), and 4-fluorophenyl isocyanate (265 mg, 1.94 mmol) and sodium hydride (67.1 mg, 1.68 mmol) were added at room temperature. After stirring the reaction solution at room temperature for 1 hour, a saturated aqueous ammonium chloride solution was added. Then, 1N aqueous hydrochloric acid solution was added, and the mixture was extracted three times with ethyl acetate. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain N-(4-fluorophenyl)-4-hydroxy-2-oxo-1-(4-(trifluorophenyl) methyl)phenyl)-2,5,6,7-tetrahydro-1H-azepine-3-carboxamide (215 mg, 0.526 mmol) was obtained.
Yield: 47%
Physical properties: melting point 112-113℃
収率:47%
物性:融点112-113℃ 1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione (300 mg, 1.11 mmol) was dissolved in N,N-dimethylacetamide (5 mL), and 4-fluorophenyl isocyanate (265 mg, 1.94 mmol) and sodium hydride (67.1 mg, 1.68 mmol) were added at room temperature. After stirring the reaction solution at room temperature for 1 hour, a saturated aqueous ammonium chloride solution was added. Then, 1N aqueous hydrochloric acid solution was added, and the mixture was extracted three times with ethyl acetate. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain N-(4-fluorophenyl)-4-hydroxy-2-oxo-1-(4-(trifluorophenyl) methyl)phenyl)-2,5,6,7-tetrahydro-1H-azepine-3-carboxamide (215 mg, 0.526 mmol) was obtained.
Yield: 47%
Physical properties: melting point 112-113℃
製造実施例4
N‐(4‐フルオロフェニル)‐4‐ヒドロキシ‐6,6‐ジメチル‐2‐オキソ‐1‐(4‐(トリフルオロメチル)フェニル)‐2,5,6,7‐テトラヒドロ‐1H‐アゼピン‐3‐カルボチオアミド(化合物番号1‐24)の製造
Manufacturing example 4
N-(4-fluorophenyl)-4-hydroxy-6,6-dimethyl-2-oxo-1-(4-(trifluoromethyl)phenyl)-2,5,6,7-tetrahydro-1H-azepine- Production of 3-carbothioamide (compound number 1-24)
N‐(4‐フルオロフェニル)‐4‐ヒドロキシ‐6,6‐ジメチル‐2‐オキソ‐1‐(4‐(トリフルオロメチル)フェニル)‐2,5,6,7‐テトラヒドロ‐1H‐アゼピン‐3‐カルボチオアミド(化合物番号1‐24)の製造
N-(4-fluorophenyl)-4-hydroxy-6,6-dimethyl-2-oxo-1-(4-(trifluoromethyl)phenyl)-2,5,6,7-tetrahydro-1H-azepine- Production of 3-carbothioamide (compound number 1-24)
6,6‐ジメチル‐1‐(4‐(トリフルオロメチル)フェニル)アゼパン‐2,4‐ジオン(62.3mg,0.208mmol)をN,N‐ジメチルアセトアミド(1mL)に溶解させ、チオイソシアン酸‐4‐フルオロフェニル(47.8mg,0.312mmol)、DBU(58.6μL,0.416mmol)を室温で加えた。反応液を室温で1時間撹拌した後、飽和塩化アンモニウム水溶液を加え、酢酸エチルで3回抽出した。有機層を減圧濃縮することにより得られた粗生成物をシリカゲルカラムクロマトグラフィーで精製することにより、N‐(4‐フルオロフェニル)‐4‐ヒドロキシ‐6,6‐ジメチル‐2‐オキソ‐1‐(4‐(トリフルオロメチル)フェニル)‐2,5,6,7‐テトラヒドロ‐1H‐アゼピン‐3‐カルボチオアミド(80.0mg,0.177mmol)を得た。
収率:15%
物性:融点112-113℃ 6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione (62.3 mg, 0.208 mmol) was dissolved in N,N-dimethylacetamide (1 mL), and thioisocyanate was added. 4-fluorophenyl acid (47.8 mg, 0.312 mmol) and DBU (58.6 μL, 0.416 mmol) were added at room temperature. After stirring the reaction solution at room temperature for 1 hour, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted three times with ethyl acetate. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain N-(4-fluorophenyl)-4-hydroxy-6,6-dimethyl-2-oxo-1- (4-(trifluoromethyl)phenyl)-2,5,6,7-tetrahydro-1H-azepine-3-carbothioamide (80.0 mg, 0.177 mmol) was obtained.
Yield: 15%
Physical properties: melting point 112-113℃
収率:15%
物性:融点112-113℃ 6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione (62.3 mg, 0.208 mmol) was dissolved in N,N-dimethylacetamide (1 mL), and thioisocyanate was added. 4-fluorophenyl acid (47.8 mg, 0.312 mmol) and DBU (58.6 μL, 0.416 mmol) were added at room temperature. After stirring the reaction solution at room temperature for 1 hour, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted three times with ethyl acetate. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain N-(4-fluorophenyl)-4-hydroxy-6,6-dimethyl-2-oxo-1- (4-(trifluoromethyl)phenyl)-2,5,6,7-tetrahydro-1H-azepine-3-carbothioamide (80.0 mg, 0.177 mmol) was obtained.
Yield: 15%
Physical properties: melting point 112-113℃
参考実施例1
1‐(4‐(トリフルオロメチル)ベンジル)アゼパン‐2,4‐ジオンの製造
参考実施例1‐1
4‐エトキシ‐1‐(4‐(トリフルオロメチル)ベンジル)‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オンの製造
Reference example 1
Reference Example 1-1 for the production of 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione
Production of 4-ethoxy-1-(4-(trifluoromethyl)benzyl)-6,7-dihydro-1H-azepin-2(5H)-one
1‐(4‐(トリフルオロメチル)ベンジル)アゼパン‐2,4‐ジオンの製造
参考実施例1‐1
4‐エトキシ‐1‐(4‐(トリフルオロメチル)ベンジル)‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オンの製造
Reference Example 1-1 for the production of 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione
Production of 4-ethoxy-1-(4-(trifluoromethyl)benzyl)-6,7-dihydro-1H-azepin-2(5H)-one
4‐エトキシ‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オン(300mg,1.93mmol)をN,N‐ジメチルアセトアミド(10mL)に溶解させ、4‐フルオロベンジルブロミド(692mg,2.90mmol)、水素化ナトリウム(101mg,2.51mmol)を室温で加えた。反応液を室温で3時間撹拌した後、飽和塩化アンモニウム水溶液を加え、酢酸エチルで3回抽出した。有機層を減圧濃縮することにより得られた粗生成物をシリカゲルカラムクロマトグラフィーで精製することにより、4‐エトキシ‐1‐(4‐(トリフルオロメチル)ベンジル)‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オン(599mg,1.91mmol)を得た。
収率:99%
物性:1H‐NMR(CDCl3):δ 7.58(d,2H),7.42(d,2H),5.17(s,1H),4.72(s,2H),3.83(q,2H),3.37-3.29(m,2H),2.40(t,2H),1.90-1.80(m,2H),1.34(t,3H) 4-Ethoxy-6,7-dihydro-1H-azepin-2(5H)-one (300 mg, 1.93 mmol) was dissolved in N,N-dimethylacetamide (10 mL) and 4-fluorobenzyl bromide (692 mg, 2 .90 mmol) and sodium hydride (101 mg, 2.51 mmol) were added at room temperature. After stirring the reaction solution at room temperature for 3 hours, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted three times with ethyl acetate. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain 4-ethoxy-1-(4-(trifluoromethyl)benzyl)-6,7-dihydro-1H- Azepin-2(5H)-one (599 mg, 1.91 mmol) was obtained.
Yield: 99%
Physical properties: 1 H-NMR (CDCl 3 ): δ 7.58 (d, 2H), 7.42 (d, 2H), 5.17 (s, 1H), 4.72 (s, 2H), 3. 83 (q, 2H), 3.37-3.29 (m, 2H), 2.40 (t, 2H), 1.90-1.80 (m, 2H), 1.34 (t, 3H)
収率:99%
物性:1H‐NMR(CDCl3):δ 7.58(d,2H),7.42(d,2H),5.17(s,1H),4.72(s,2H),3.83(q,2H),3.37-3.29(m,2H),2.40(t,2H),1.90-1.80(m,2H),1.34(t,3H) 4-Ethoxy-6,7-dihydro-1H-azepin-2(5H)-one (300 mg, 1.93 mmol) was dissolved in N,N-dimethylacetamide (10 mL) and 4-fluorobenzyl bromide (692 mg, 2 .90 mmol) and sodium hydride (101 mg, 2.51 mmol) were added at room temperature. After stirring the reaction solution at room temperature for 3 hours, a saturated aqueous ammonium chloride solution was added, and the mixture was extracted three times with ethyl acetate. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain 4-ethoxy-1-(4-(trifluoromethyl)benzyl)-6,7-dihydro-1H- Azepin-2(5H)-one (599 mg, 1.91 mmol) was obtained.
Yield: 99%
Physical properties: 1 H-NMR (CDCl 3 ): δ 7.58 (d, 2H), 7.42 (d, 2H), 5.17 (s, 1H), 4.72 (s, 2H), 3. 83 (q, 2H), 3.37-3.29 (m, 2H), 2.40 (t, 2H), 1.90-1.80 (m, 2H), 1.34 (t, 3H)
参考実施例1‐2
1‐(4‐(トリフルオロメチル)ベンジル)アゼパン‐2,4‐ジオンの製造
Reference example 1-2
Production of 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione
1‐(4‐(トリフルオロメチル)ベンジル)アゼパン‐2,4‐ジオンの製造
Production of 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione
4‐エトキシ‐1‐(4‐(トリフルオロメチル)ベンジル)‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オン(599mg,1.91mmol)をテトラヒドロフラン(5mL)、3M塩酸水溶液に溶解させ、室温で1時間撹拌した後、酢酸エチルで3回抽出した。有機層を減圧濃縮することで得られた1‐(4‐(トリフルオロメチル)ベンジル)アゼパン‐2,4‐ジオンの粗生成物(529mg,1.85mmol)は精製することなくそのまま次の反応に用いた。
収率:97%
物性:1H‐NMR(CDCl3):δ 7.61(d,2H),7.42(d,2H),4.71(s,2H),3.66(s,2H),3.56(t,2H),2.59(t,2H),1.94―1.84(m,2H) 4-Ethoxy-1-(4-(trifluoromethyl)benzyl)-6,7-dihydro-1H-azepin-2(5H)-one (599 mg, 1.91 mmol) was added to tetrahydrofuran (5 mL) and 3M aqueous hydrochloric acid solution. After dissolving and stirring at room temperature for 1 hour, it was extracted three times with ethyl acetate. The crude product of 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione (529 mg, 1.85 mmol) obtained by concentrating the organic layer under reduced pressure was directly used in the next reaction without purification. It was used for.
Yield: 97%
Physical properties: 1 H-NMR (CDCl 3 ): δ 7.61 (d, 2H), 7.42 (d, 2H), 4.71 (s, 2H), 3.66 (s, 2H), 3. 56 (t, 2H), 2.59 (t, 2H), 1.94-1.84 (m, 2H)
収率:97%
物性:1H‐NMR(CDCl3):δ 7.61(d,2H),7.42(d,2H),4.71(s,2H),3.66(s,2H),3.56(t,2H),2.59(t,2H),1.94―1.84(m,2H) 4-Ethoxy-1-(4-(trifluoromethyl)benzyl)-6,7-dihydro-1H-azepin-2(5H)-one (599 mg, 1.91 mmol) was added to tetrahydrofuran (5 mL) and 3M aqueous hydrochloric acid solution. After dissolving and stirring at room temperature for 1 hour, it was extracted three times with ethyl acetate. The crude product of 1-(4-(trifluoromethyl)benzyl)azepane-2,4-dione (529 mg, 1.85 mmol) obtained by concentrating the organic layer under reduced pressure was directly used in the next reaction without purification. It was used for.
Yield: 97%
Physical properties: 1 H-NMR (CDCl 3 ): δ 7.61 (d, 2H), 7.42 (d, 2H), 4.71 (s, 2H), 3.66 (s, 2H), 3. 56 (t, 2H), 2.59 (t, 2H), 1.94-1.84 (m, 2H)
参考実施例2
1‐(4‐(トリフルオロメチル)フェニル)アゼパン‐2,4‐ジオンの製造
参考実施例2‐1
4‐エトキシ‐1‐(4‐(トリフルオロメチル)フェニル)‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オンの製造
Reference example 2
Reference Example 2-1 for the production of 1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione
Production of 4-ethoxy-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H-azepin-2(5H)-one
1‐(4‐(トリフルオロメチル)フェニル)アゼパン‐2,4‐ジオンの製造
参考実施例2‐1
4‐エトキシ‐1‐(4‐(トリフルオロメチル)フェニル)‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オンの製造
Reference Example 2-1 for the production of 1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione
Production of 4-ethoxy-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H-azepin-2(5H)-one
4‐エトキシ‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オン(1.00 g, 6.44 mmol) をN,N‐ジメチルアセトアミド(10.0mL)に溶解させヨウ化銅(I)(245mg,1.29mmol)、リン酸カリウム(2.73g,12.9mmol)、N,N‐ジメチルエチレンジアミン(139μL,1.29mmol)、4‐トリフルオロメチルヨードベンゼン(2.63g,9.66mmol)を室温で加えた。反応液を110℃まで加熱し3時間撹拌したが、原料が消失していなかったため、反応液にヨウ化銅(I)(1.23g,6.44mmol)、N,N‐ジメチルエチレンジアミン (692 μL,6.44mmol)を追加し、140℃で8時間加熱した。その後、反応液を室温まで放冷し、酢酸エチルを用いて分液操作を行った。有機層を減圧濃縮することにより得られた粗生成物をシリカゲルカラムクロマトグラフィーで精製することにより、4‐エトキシ‐1‐(4‐(トリフルオロメチル)フェニル)‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オン(748mg,2.50mmol)を得た。
収率:40%
物性:1H‐NMR(CDCl3):δ 7.63(d,2H),7.42(d,2H),5.22(s,1H),3.92-3.80(m,4H),2.58(t,2H),2.17―2.08(m,2H),1.38(t,3H) 4-Ethoxy-6,7-dihydro-1H-azepin-2(5H)-one (1.00 g, 6.44 mmol) was dissolved in N,N-dimethylacetamide (10.0 mL) and copper(I) iodide (245 mg , 1.29 mmol), potassium phosphate (2.73 g, 12.9 mmol), N,N-dimethylethylenediamine (139 μL, 1.29 mmol), 4-trifluoromethyliodobenzene (2.63 g, 9.66 mmol). Added at room temperature. The reaction solution was heated to 110°C and stirred for 3 hours, but since the raw materials had not disappeared, copper(I) iodide (1.23 g, 6.44 mmol) and N,N-dimethylethylenediamine (692 μL) were added to the reaction solution. , 6.44 mmol) and heated at 140° C. for 8 hours. Thereafter, the reaction solution was allowed to cool to room temperature, and a liquid separation operation was performed using ethyl acetate. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain 4-ethoxy-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H- Azepin-2(5H)-one (748 mg, 2.50 mmol) was obtained.
Yield: 40%
Physical properties: 1 H-NMR (CDCl 3 ): δ 7.63 (d, 2H), 7.42 (d, 2H), 5.22 (s, 1H), 3.92-3.80 (m, 4H ), 2.58 (t, 2H), 2.17-2.08 (m, 2H), 1.38 (t, 3H)
収率:40%
物性:1H‐NMR(CDCl3):δ 7.63(d,2H),7.42(d,2H),5.22(s,1H),3.92-3.80(m,4H),2.58(t,2H),2.17―2.08(m,2H),1.38(t,3H) 4-Ethoxy-6,7-dihydro-1H-azepin-2(5H)-one (1.00 g, 6.44 mmol) was dissolved in N,N-dimethylacetamide (10.0 mL) and copper(I) iodide (245 mg , 1.29 mmol), potassium phosphate (2.73 g, 12.9 mmol), N,N-dimethylethylenediamine (139 μL, 1.29 mmol), 4-trifluoromethyliodobenzene (2.63 g, 9.66 mmol). Added at room temperature. The reaction solution was heated to 110°C and stirred for 3 hours, but since the raw materials had not disappeared, copper(I) iodide (1.23 g, 6.44 mmol) and N,N-dimethylethylenediamine (692 μL) were added to the reaction solution. , 6.44 mmol) and heated at 140° C. for 8 hours. Thereafter, the reaction solution was allowed to cool to room temperature, and a liquid separation operation was performed using ethyl acetate. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain 4-ethoxy-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H- Azepin-2(5H)-one (748 mg, 2.50 mmol) was obtained.
Yield: 40%
Physical properties: 1 H-NMR (CDCl 3 ): δ 7.63 (d, 2H), 7.42 (d, 2H), 5.22 (s, 1H), 3.92-3.80 (m, 4H ), 2.58 (t, 2H), 2.17-2.08 (m, 2H), 1.38 (t, 3H)
参考実施例2‐2
1‐(4‐(トリフルオロメチル)フェニル)アゼパン‐2,4‐ジオンの製造
Reference example 2-2
Production of 1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione
1‐(4‐(トリフルオロメチル)フェニル)アゼパン‐2,4‐ジオンの製造
Production of 1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione
4‐エトキシ‐1‐(4‐(トリフルオロメチル)フェニル)‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オン(748 mg, 2.50 mmol)をテトラヒドロフラン(5mL)、3M塩酸水溶液に溶解させ、室温で1時間撹拌した後、酢酸エチルで3回抽出した。得られた1‐(4‐(トリフルオロメチル)フェニル)アゼパン‐2,4‐ジオンの粗生成物(651mg,2.40mmol)は精製することなくそのまま次の反応に用いた。
収率:96% 4-Ethoxy-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H-azepin-2(5H)-one (748 mg, 2.50 mmol) in tetrahydrofuran (5 mL) and 3M hydrochloric acid. The mixture was dissolved in an aqueous solution, stirred at room temperature for 1 hour, and then extracted three times with ethyl acetate. The obtained crude product of 1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione (651 mg, 2.40 mmol) was used as it was in the next reaction without being purified.
Yield: 96%
収率:96% 4-Ethoxy-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H-azepin-2(5H)-one (748 mg, 2.50 mmol) in tetrahydrofuran (5 mL) and 3M hydrochloric acid. The mixture was dissolved in an aqueous solution, stirred at room temperature for 1 hour, and then extracted three times with ethyl acetate. The obtained crude product of 1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione (651 mg, 2.40 mmol) was used as it was in the next reaction without being purified.
Yield: 96%
参考実施例3
6,6‐ジメチル‐1‐(4‐(トリフルオロメチル)フェニル)アゼパン‐2,4‐ジオンの製造
参考実施例3‐1
4‐エトキシ‐6,6‐ジメチル‐1‐(4‐(トリフルオロメチル)フェニル)‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オンの製造
Reference example 3
Production reference example 3-1 of 6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione
Production of 4-ethoxy-6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H-azepin-2(5H)-one
6,6‐ジメチル‐1‐(4‐(トリフルオロメチル)フェニル)アゼパン‐2,4‐ジオンの製造
参考実施例3‐1
4‐エトキシ‐6,6‐ジメチル‐1‐(4‐(トリフルオロメチル)フェニル)‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オンの製造
Production reference example 3-1 of 6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione
Production of 4-ethoxy-6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H-azepin-2(5H)-one
4‐エトキシ‐6,6‐ジメチル‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オン(654mg,3.57mmol)をN,N‐ジメチルアセトアミド(5mL)に溶解させヨウ化銅(I)(1.02g,5.35mmol)、リン酸カリウム(1.52g,7.14mmol)、N,N‐ジメチルエチレンジアミン(576μL,5.36mmol)、4‐トリフルオロメチルヨードベンゼン(1.94g,7.14mmol)を室温で加えた。反応液を110℃まで加熱し5時間した。その後、反応液を室温まで放冷し、水、酢酸エチルを加え分液操作を行った。有機層を減圧濃縮することにより得られた粗生成物をシリカゲルカラムクロマトグラフィーで精製することにより、4‐エトキシ‐6,6‐ジメチル‐1‐(4‐(トリフルオロメチル)フェニル)‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オン(527mg,1.61mmol)を得た。
収率:45%
物性:物性:融点45-46℃ 4-Ethoxy-6,6-dimethyl-6,7-dihydro-1H-azepin-2(5H)-one (654 mg, 3.57 mmol) was dissolved in N,N-dimethylacetamide (5 mL) and copper iodide ( I) (1.02g, 5.35mmol), potassium phosphate (1.52g, 7.14mmol), N,N-dimethylethylenediamine (576μL, 5.36mmol), 4-trifluoromethyliodobenzene (1.94g) , 7.14 mmol) was added at room temperature. The reaction solution was heated to 110°C for 5 hours. Thereafter, the reaction solution was allowed to cool to room temperature, and water and ethyl acetate were added to perform a liquid separation operation. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain 4-ethoxy-6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)-6, 7-dihydro-1H-azepin-2(5H)-one (527 mg, 1.61 mmol) was obtained.
Yield: 45%
Physical properties: Physical properties: Melting point 45-46℃
収率:45%
物性:物性:融点45-46℃ 4-Ethoxy-6,6-dimethyl-6,7-dihydro-1H-azepin-2(5H)-one (654 mg, 3.57 mmol) was dissolved in N,N-dimethylacetamide (5 mL) and copper iodide ( I) (1.02g, 5.35mmol), potassium phosphate (1.52g, 7.14mmol), N,N-dimethylethylenediamine (576μL, 5.36mmol), 4-trifluoromethyliodobenzene (1.94g) , 7.14 mmol) was added at room temperature. The reaction solution was heated to 110°C for 5 hours. Thereafter, the reaction solution was allowed to cool to room temperature, and water and ethyl acetate were added to perform a liquid separation operation. The crude product obtained by concentrating the organic layer under reduced pressure was purified by silica gel column chromatography to obtain 4-ethoxy-6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)-6, 7-dihydro-1H-azepin-2(5H)-one (527 mg, 1.61 mmol) was obtained.
Yield: 45%
Physical properties: Physical properties: Melting point 45-46℃
参考実施例3‐2
6,6‐ジメチル‐1‐(4‐(トリフルオロメチル)フェニル)アゼパン‐2,4‐ジオンの製造
Reference example 3-2
Production of 6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione
6,6‐ジメチル‐1‐(4‐(トリフルオロメチル)フェニル)アゼパン‐2,4‐ジオンの製造
Production of 6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione
4‐エトキシ‐6,6‐ジメチル‐1‐(4‐(トリフルオロメチル)フェニル)‐6,7‐ジヒドロ‐1H‐アゼピン‐2(5H)‐オン(527 mg, 1.61 mmol)をテトラヒドロフラン(5mL)、3M塩酸水溶液に溶解させ、室温で5時間撹拌した後、酢酸エチルで3回抽出した。有機層を減圧濃縮することで得られた6,6‐ジメチル‐1‐(4‐(トリフルオロメチル)フェニル)アゼパン‐2,4‐ジオンの粗生成物(482mg,1.61mmol)は精製することなくそのまま次の反応に用いた。
収率:100% 4-ethoxy-6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H-azepin-2(5H)-one (527 mg, 1.61 mmol) was dissolved in tetrahydrofuran. (5 mL) was dissolved in a 3M aqueous hydrochloric acid solution, stirred at room temperature for 5 hours, and extracted three times with ethyl acetate. The crude product (482 mg, 1.61 mmol) of 6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione obtained by concentrating the organic layer under reduced pressure is purified. It was used for the next reaction as it was.
Yield: 100%
収率:100% 4-ethoxy-6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)-6,7-dihydro-1H-azepin-2(5H)-one (527 mg, 1.61 mmol) was dissolved in tetrahydrofuran. (5 mL) was dissolved in a 3M aqueous hydrochloric acid solution, stirred at room temperature for 5 hours, and extracted three times with ethyl acetate. The crude product (482 mg, 1.61 mmol) of 6,6-dimethyl-1-(4-(trifluoromethyl)phenyl)azepane-2,4-dione obtained by concentrating the organic layer under reduced pressure is purified. It was used for the next reaction as it was.
Yield: 100%
以下に、製剤例を示すが、これらに限定されるものではない。製剤例中、部とあるのは重量部を示す。
Formulation examples are shown below, but are not limited to these. In the formulation examples, parts indicate parts by weight.
製剤例1.
本発明化合物 10部
キシレン 70部
N‐メチルピロリドン 10部
ポリオキシエチレンノニルフェニルエーテルと
アルキルベンゼンスルホン酸カルシウムとの混合物 10部
以上を均一に混合溶解して乳剤とする。 Formulation example 1.
Compound of the present invention: 10 parts Xylene: 70 parts N-methylpyrrolidone: 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate: 10 parts The above ingredients are uniformly mixed and dissolved to obtain an emulsion.
本発明化合物 10部
キシレン 70部
N‐メチルピロリドン 10部
ポリオキシエチレンノニルフェニルエーテルと
アルキルベンゼンスルホン酸カルシウムとの混合物 10部
以上を均一に混合溶解して乳剤とする。 Formulation example 1.
Compound of the present invention: 10 parts Xylene: 70 parts N-methylpyrrolidone: 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate: 10 parts The above ingredients are uniformly mixed and dissolved to obtain an emulsion.
製剤例2.
本発明化合物 3部
クレー粉末 82部
珪藻土粉末 15部
以上を均一に混合粉砕して粉剤とする。 Formulation example 2.
Compound of the present invention: 3 parts Clay powder: 82 parts Diatomaceous earth powder: 15 parts The above ingredients are uniformly mixed and pulverized to obtain a powder.
本発明化合物 3部
クレー粉末 82部
珪藻土粉末 15部
以上を均一に混合粉砕して粉剤とする。 Formulation example 2.
Compound of the present invention: 3 parts Clay powder: 82 parts Diatomaceous earth powder: 15 parts The above ingredients are uniformly mixed and pulverized to obtain a powder.
製剤例3.
本発明化合物 5部
ベントナイトとクレーの混合粉末 90部
リグニンスルホン酸カルシウム 5部
以上を均一に混合し、適量の水を加えて混練し、造粒、乾燥して粒剤とする。 Formulation example 3.
Compound of the present invention: 5 parts Mixed powder of bentonite and clay: 90 parts Calcium ligninsulfonate: 5 parts The above ingredients are mixed uniformly, an appropriate amount of water is added, kneaded, granulated, and dried to obtain granules.
本発明化合物 5部
ベントナイトとクレーの混合粉末 90部
リグニンスルホン酸カルシウム 5部
以上を均一に混合し、適量の水を加えて混練し、造粒、乾燥して粒剤とする。 Formulation example 3.
Compound of the present invention: 5 parts Mixed powder of bentonite and clay: 90 parts Calcium ligninsulfonate: 5 parts The above ingredients are mixed uniformly, an appropriate amount of water is added, kneaded, granulated, and dried to obtain granules.
製剤例4.
本発明化合物 20部
カオリンと合成高分散珪酸 75部
ポリオキシエチレンノニルフェニルエーテルと
アルキルベンゼンスルホン酸カルシウムとの混合物 5部
以上を均一に混合粉砕して水和剤とする。 Formulation example 4.
Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above are uniformly mixed and pulverized to prepare a wettable powder.
本発明化合物 20部
カオリンと合成高分散珪酸 75部
ポリオキシエチレンノニルフェニルエーテルと
アルキルベンゼンスルホン酸カルシウムとの混合物 5部
以上を均一に混合粉砕して水和剤とする。 Formulation example 4.
Compound of the present invention 20 parts Kaolin and synthetic highly dispersed silicic acid 75 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 5 parts The above are uniformly mixed and pulverized to prepare a wettable powder.
以下に、生物試験の実施例を示すが、本発明はこれらに限定されるわけではない
Examples of biological tests are shown below, but the present invention is not limited thereto.
試験例1.コナガ(Plutella xylostella) に対する殺虫試験
ハクサイ実生にコナガの成虫を放飼して産卵させ、放飼2日後に産下卵の付いたハクサイ実生を本発明の一般式(1)で表される化合物を有効成分とする薬剤を500ppmに希釈した薬液に約30秒間浸漬し、風乾後に25℃の恒温室に静置した。薬液浸漬6日後に生存虫数を調査し、下記の式により補正死虫率を算出し、下記の判定基準に従って判定を行った。1区10頭3連制。 Test example 1. Insecticidal test against diamondback moth (Plutella xylostella) Adult diamondback moths were released on Chinese cabbage seedlings to lay eggs, and two days after the release, the Chinese cabbage seedlings with eggs were treated with the compound represented by the general formula (1) of the present invention. The sample was immersed for about 30 seconds in a drug solution containing a drug as an active ingredient diluted to 500 ppm, air-dried, and then left in a constant temperature room at 25°C. The number of surviving insects was investigated after 6 days of immersion in the chemical solution, and the corrected mortality rate was calculated using the following formula, and judgment was made according to the following criteria. 1 ward 10 horses 3 consecutive races.
ハクサイ実生にコナガの成虫を放飼して産卵させ、放飼2日後に産下卵の付いたハクサイ実生を本発明の一般式(1)で表される化合物を有効成分とする薬剤を500ppmに希釈した薬液に約30秒間浸漬し、風乾後に25℃の恒温室に静置した。薬液浸漬6日後に生存虫数を調査し、下記の式により補正死虫率を算出し、下記の判定基準に従って判定を行った。1区10頭3連制。 Test example 1. Insecticidal test against diamondback moth (Plutella xylostella) Adult diamondback moths were released on Chinese cabbage seedlings to lay eggs, and two days after the release, the Chinese cabbage seedlings with eggs were treated with the compound represented by the general formula (1) of the present invention. The sample was immersed for about 30 seconds in a drug solution containing a drug as an active ingredient diluted to 500 ppm, air-dried, and then left in a constant temperature room at 25°C. The number of surviving insects was investigated after 6 days of immersion in the chemical solution, and the corrected mortality rate was calculated using the following formula, and judgment was made according to the following criteria. 1 ward 10 horses 3 consecutive races.
判定基準. A・・・死虫率100%
B・・・死虫率99%~90%
C・・・死虫率89%~80%
D・・・死虫率79%~50%
E・・・死虫率49%~0% Judgment criteria. A... Mortality rate 100%
B... Mortality rate 99% to 90%
C... Mortality rate 89% to 80%
D... Mortality rate 79% to 50%
E... Mortality rate 49% to 0%
B・・・死虫率99%~90%
C・・・死虫率89%~80%
D・・・死虫率79%~50%
E・・・死虫率49%~0% Judgment criteria. A... Mortality rate 100%
B... Mortality rate 99% to 90%
C... Mortality rate 89% to 80%
D... Mortality rate 79% to 50%
E... Mortality rate 49% to 0%
その結果、本発明の一般式(1)で表される化合物は有意な殺虫活性を示し、特に化合物番号1‐52、1‐53、1‐54、1‐55、1‐58、1‐111、1‐112、1‐118、1‐121、1‐124、1‐127及び1‐128の化合物はコナガに対して、B判定以上の優れた活性を示した。
As a result, the compounds represented by the general formula (1) of the present invention exhibited significant insecticidal activity, especially compound numbers 1-52, 1-53, 1-54, 1-55, 1-58, 1-111. , 1-112, 1-118, 1-121, 1-124, 1-127, and 1-128 showed excellent activity against diamondback moths with a grade of B or better.
試験例2.犬糸状虫(Dirofilaria immitis)の発育に対する影響評価試験
24穴プレート1穴毎に所定の調整液、犬糸状虫のL‐3ステージ幼虫8-20頭及び本発明の化合物のDMSO希釈溶液を加えて最終濃度を10μMとした。その7日後にL‐4ステージに発育した幼虫を計数し、L3ステージ幼虫からL4ステージ幼虫への発育阻害率を算出した。 Test example 2. Test for evaluating the effect on the growth of Dirofilaria immitis A prescribed adjustment solution, 8-20 L-3 stage larvae of Dirofilaria immitis, and a DMSO diluted solution of the compound of the present invention were added to each hole of a 24-well plate. The final concentration was 10 μM. Seven days later, the larvae that had developed to the L-4 stage were counted, and the rate of growth inhibition from the L3 stage larva to the L4 stage larva was calculated.
24穴プレート1穴毎に所定の調整液、犬糸状虫のL‐3ステージ幼虫8-20頭及び本発明の化合物のDMSO希釈溶液を加えて最終濃度を10μMとした。その7日後にL‐4ステージに発育した幼虫を計数し、L3ステージ幼虫からL4ステージ幼虫への発育阻害率を算出した。 Test example 2. Test for evaluating the effect on the growth of Dirofilaria immitis A prescribed adjustment solution, 8-20 L-3 stage larvae of Dirofilaria immitis, and a DMSO diluted solution of the compound of the present invention were added to each hole of a 24-well plate. The final concentration was 10 μM. Seven days later, the larvae that had developed to the L-4 stage were counted, and the rate of growth inhibition from the L3 stage larva to the L4 stage larva was calculated.
その結果、本発明の一般式(1)で表される化合物のうち、化合物番号1‐5、1‐9、1‐10、1‐11、1‐12、1‐13、1‐14、1‐20、1‐21、1‐40、1‐43、1‐44、1‐46、1‐48、1‐49、1‐50、1‐51、1‐55、1‐56、1‐57、1‐58及び1‐117の化合物は、50%以上の発育阻害率を示した。
As a result, among the compounds represented by the general formula (1) of the present invention, compound numbers 1-5, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1 -20, 1-21, 1-40, 1-43, 1-44, 1-46, 1-48, 1-49, 1-50, 1-51, 1-55, 1-56, 1-57 , 1-58 and 1-117 showed a growth inhibition rate of 50% or more.
本発明の化合物並びにその塩は有害生物防除剤として優れた効果を有する。
The compounds of the present invention and their salts have excellent effects as pest control agents.
Claims (11)
- 一般式(1)
R1は、
(a1) 水素原子;(a2) (C1-C6)アルキル基;(a3) (C2-C6)アルケニル基;(a4) (C2-C6)アルキニル基;(a5) (C3-C6)シクロアルキル基;(a6) ハロ(C1-C6)アルキル基;(a7) ハロ(C2-C6)アルケニル基;(a8) ハロ(C2-C6)アルキニル基;(a9) ハロ(C3-C6)シクロアルキル基;(a10) 置換基群Aからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C1-C6)アルキル基;(a11) 置換基群Bからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C3-C6)シクロアルキル基;(a12) (C1-C6)アルコキシカルボニル基;(a13) N‐(C1-C6)アルキルアミノカルボニル基;(a14) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(a15) フェニルアミノカルボニル基;(a16) フェニル(C1-C6)アルキル基;(a17) 置換基群Cからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基;(a18) ピリジル(C1-C6)アルキル基;(a19) 置換基群Cからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル(C1-C6)アルキル基;(a20) ピリダジニル(C1-C6)アルキル基;(a21) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル(C1-C6)アルキル基;(a22) ピラジニル(C1-C6)アルキル基;(a23) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル(C1-C6)アルキル基;(a24) ピリミジニル(C1-C6)アルキル基;(a25) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル(C1-C6)アルキル基;(a26) オキサゾリル(C1-C6)アルキル基;(a27) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル(C1-C6)アルキル基;(a28) イソキサゾリル(C1-C6)アルキル基;(a29) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル(C1-C6)アルキル基;(a30) チエニル(C1-C6)アルキル基;(a31) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換チエニル(C1-C6)アルキル基;(a32) チアゾリル(C1-C6)アルキル基;(a33) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル(C1-C6)アルキル基;(a34) イソチアゾリル(C1-C6)アルキル基;(a35) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソチアゾリル(C1-C6)アルキル基;(a36) チアジアゾリル(C1-C6)アルキル基;(a37) 置換基群Cから選択される1個の置換基を環上に有する置換チアジアゾリル(C1-C6)アルキル基;(a38) ピラゾリル(C1-C6)アルキル基;(a39) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル(C1-C6)アルキル基;(a40) トリアゾリル(C1-C6)アルキル基;(a41) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル(C1-C6)アルキル基;(a42) テトラゾリル(C1-C6)アルキル基;(a43) 置換基群Cから選択される1個の置換基を環上に有する置換テトラゾリル(C1-C6)アルキル基;(a44) フェニル基;(a45) 置換基群Dからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(a46) ピリジル基;(a47) 置換基群Dからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(a48) ピリダジニル基;(a49) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル基;(a50) ピラジニル基;(a51) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル基;(a52) ピリミジニル基;(a53) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(a54) オキサゾリル基;(a55) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル基;(a56) イソキサゾリル基;(a57) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル基;(a58) チエニル基;(a59) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換チエニル基;(a60) チアゾリル基;(a61) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(a62) イソチアゾリル基;(a63) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソチアゾリル基;(a64) チアジアゾリル基;(a65) 置換基群Dから選択される1個の置換基を環上に有する置換チアジアゾリル基;(a66) ピラゾリル基;(a67) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(a68) トリアゾリル基;(a69) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル基;(a70) テトラゾリル基;(a71) 置換基群Dから選択される1個の置換基を環上に有する置換テトラゾリル基;(a72) ベンゾチアゾリル基;又は(a73) 置換基群Dから選択される1乃至4個の置換基を環上に有する置換ベンゾチアゾリル基を示す。
R2aは、
(b1) 水素原子;又は(b2) (C1-C6)アルキル基を示す。
R2bは、
(c1) 水素原子;又は(c2) (C1-C6)アルキル基を示す。
R3aは、
(d1) 水素原子;(d2) (C1-C6)アルキル基;(d3) フェニル基;又は(d4) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基を示す。
R3bは、
(e1) 水素原子;又は(e2) (C1-C6)アルキル基を示す。
R4aは、
(f1) 水素原子;又は(f2) (C1-C6)アルキル基を示す。
R4bは、
(g1) 水素原子;又は(g2) (C1-C6)アルキル基を示す。
R5は、
(h1) (C1-C6)アルキル基;(h2) (C2-C6)アルケニル基;(h3) (C2-C6)アルキニル基;(h4) (C3-C6)シクロアルキル基;(h5) ハロ(C1-C6)アルキル基;(h6) ハロ(C2-C6)アルケニル基;(h7) ハロ(C2-C6)アルキニル基;(h8) ハロ(C3-C6)シクロアルキル基;(h9) 置換基群Aからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C1-C6)アルキル基;(h10) 置換基群Bからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換(C3-C6)シクロアルキル基;(h11) フェニル基;(h12) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(h13) ピリジル基;(h14) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(h15) ピリダジニル基;(h16) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル基;(h17) ピリミジニル基;(h18) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(h19) ピラジニル基;(h20) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル基;(h21) トリアジニル基;(h22) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアジニル基;(h23) フラニル基;(h24) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換フラニル基;(h25) オキサゾリル基;(h26) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル基;(h27) イソキサゾリル基;(h28) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル基;(h29) チエニル基;(h30) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換チエニル基;(h31) チアゾリル基;(h32) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(h33) イソチアゾリル基;(h34) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソチアゾリル基;(h35) チアジアゾリル基;(h36) 置換基群Eから選択される1個の置換基を環上に有する置換チアジアゾリル基;(h37) ピラゾリル基;(h38) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(h39) トリアゾリル基;(h40) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル基;(h41) テトラゾリル基;(h42) 置換基群Eから選択される1個の置換基を環上に有する置換テトラゾリル基;(h43) ベンゾオキサゾリル基;(h44) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ベンゾオキサゾリル基;(h45) ベンゾチアゾリル基;(h46) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ベンゾチアゾリル基;(h47) キノリニル基;(h48) 置換基群Eからそれぞれ独立に選択される1乃至6個の置換基を環上に有する置換キノリニル基;(h49) ナフチル基;(h50) 置換基群Eからそれぞれ独立に選択される1乃至7個の置換基を環上に有する置換ナフチル基;(h51) テトラヒドロナフチル基;(h52) 置換基群Eからそれぞれ独立に選択される1乃至10個の置換基を環上に有する置換テトラヒドロナフチル基;(h53) フェニル(C1-C6)アルキル基;(h54) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基;(h55) ピリジル(C1-C6)アルキル基;(h56) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル(C1-C6)アルキル基;(h57) ピリダジニル(C1-C6)アルキル基;(h58) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル(C1-C6)アルキル基;(h59) ピラジニル(C1-C6)アルキル基;(h60) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル(C1-C6)アルキル基;(h61) ピリミジニル(C1-C6)アルキル基;又は(h62) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル(C1-C6)アルキル基を示す。
R6は、
(i1) 水素原子;(i2) (C1-C6)アルキル基;(i3) (C3-C6)シクロアルキル基;(i4) (C1-C6)アルコキシ基;又は(i5) (C1-C6)アルキルカルボニル基を示す。
Xは、ヒドロキシル基、(C1-C6)アルコキシ基、(C1-C6)アルキルスルファニル基、(C1-C6)アルキルスルフィニル基、又は(C1-C6)アルキルスルホニル基を示す。
Yは、酸素原子、硫黄原子、又はNR7基(式中、R7は、水素原子、(C1-C6)アルキル基、又はハロゲン原子、シアノ基、(C1-C6)アルキル基、及びハロ(C1-C6)アルキル基からなる群からそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基を示す。)を示す。
置換基群Aは、
(j1) シアノ基;(j2) (C1-C6)アルキル基;(j3) (C2-C6)アルケニル基;(j4) (C2-C6)アルキニル基;(j5) (C3-C6)シクロアルキル基;(j6) (C1-C6)アルコキシ基;(j7) (C1-C6)アルキルスルファニル基;(j8) (C1-C6)アルキルスルフィニル基;(j9) (C1-C6)アルキルスルホニル基;(j10) ハロ(C1-C6)アルキル基;(j11) ハロ(C2-C6)アルケニル基;(j12) ハロ(C2-C6)アルキニル基;(j13) ハロ(C3-C6)シクロアルキル基;(j14) ハロ(C1-C6)アルコキシ基;(j15) ハロ(C1-C6)アルキルスルファニル基;(j16) ハロ(C1-C6)アルキルスルフィニル基;(j17) ハロ(C1-C6)アルキルスルホニル基;(j18) (C1-C6)アルコキシカルボニル基;及び(j19) ハロ(C1-C6)アルコキシカルボニル基からなる。
置換基群Bは、
(k1) シアノ基;(k2) (C1-C6)アルキル基;(k3) (C2-C6)アルケニル基;(k4) (C2-C6)アルキニル基;(k5) (C3-C6)シクロアルキル基;(k6) (C1-C6)アルコキシ基;(k7) (C1-C6)アルキルスルファニル基;(k8) (C1-C6)アルキルスルフィニル基;(k9) (C1-C6)アルキルスルホニル基;(k10) ハロ(C1-C6)アルキル基;(k11) ハロ(C3-C6)シクロアルキル基;(k12) ハロ(C1-C6)アルコキシ基;(k13) ハロ(C1-C6)アルキルスルファニル基;(k14) ハロ(C1-C6)アルキルスルフィニル基;(k15) ハロ(C1-C6)アルキルスルホニル基;及び(k16) フェニル基からなる。
置換基群Cは、
(l1) ハロゲン原子;(l2) シアノ基;(l3) ニトロ基;(l4) ヒドロキシル基;(l5) カルボキシル基;(l6) (C1-C6)アルキル基;(l7) (C2-C6)アルケニル基;(l8) (C2-C6)アルキニル基;(l9) (C1-C6)アルコキシ基;(l10) (C3-C6)シクロアルキル基;(l11) (C1-C6)アルキルスルファニル基;(l12) (C1-C6)アルキルスルフィニル基;(l13) (C1-C6)アルキルスルホニル基;(l14) ハロ(C1-C6)アルキル基;(l15) ハロ(C2-C6)アルケニル基;(l16) ハロ(C2-C6)アルキニル基;(l17) ハロ(C1-C6)アルコキシ基;(l18) ハロ(C3-C6)シクロアルキル基;(l19) ハロ(C1-C6)アルキルスルファニル基;(l20) ハロ(C1-C6)アルキルスルフィニル基;(l21) ハロ(C1-C6)アルキルスルホニル基;(l22) (C1-C6)アルキルカルボニル基;(l23) (C1-C6)アルコキシカルボニル基;(l24) (C1-C6)アルキルカルボニルアミノ基;(l25) ハロ(C1-C6)アルキルカルボニルアミノ基;(l26) (C1-C6)アルキルスルホニルアミノ基;(l27) ハロ(C1-C6)アルキルスルホニルアミノ基;(l28) N‐(C1-C6)アルキルアミノカルボニル基;(l29) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(l30) N‐ハロ(C1-C6)アルキルアミノカルボニル基;(l31) N‐(C1-C6)アルキルアミノスルホニル基;及び(l32) N,N‐ジ(C1-C6)アルキルアミノスルホニル基(当該(C1-C6)アルキルは、同一又は異なってもよい)からなる。
置換基群Dは、
(m1) ハロゲン原子;(m2) シアノ基;(m3) ニトロ基;(m4) アミノ基;(m5) ヒドロキシル基;(m6) カルボキシル基;(m7) (C1-C6)アルキル基;(m8) (C2-C6)アルケニル基;(m9) (C2-C6)アルキニル基;(m10) (C1-C6)アルコキシ基;(m11) (C3-C6)シクロアルキル基;(m12) (C1-C6)アルキルスルファニル基;(m13) (C1-C6)アルキルスルフィニル基;(m14) (C1-C6)アルキルスルホニル基;(m15) ハロ(C1-C6)アルキル基;(m16) ハロ(C2-C6)アルケニル基;(m17) ハロ(C2-C6)アルキニル基;(m18) ハロ(C1-C6)アルコキシ基;(m19) ハロ(C3-C6)シクロアルキル基;(m20) ハロ(C1-C6)アルキルスルファニル基;(m21) ハロ(C1-C6)アルキルスルフィニル基;(m22) ハロ(C1-C6)アルキルスルホニル基;(m23) シアノ基、(C1-C6)アルキル基、ハロ(C1-C6)アルキル基、(C1-C6)アルコキシ基及び(C1-C6)アルキルカルボニル基からなる群からそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換(C3-C6)シクロアルキル基;(m24) (C1-C6)アルコキシ(C1-C6)アルキル基;(m25) (C1-C6)アルコキシ(C1-C6)アルコキシ基;(m26) (C1-C6)アルキルカルボニルアミノ基;(m27) ハロ(C1-C6)アルキルカルボニルアミノ基;(m28) (C1-C6)アルキルスルホニルアミノ基;(m29) ハロ(C1-C6)アルキルスルホニルアミノ基;(m30) (C1-C6)アルコキシカルボニル基;(m31) N‐(C1-C6)アルキルアミノカルボニル基;(m32) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(m33) N‐ハロ(C1-C6)アルキルアミノカルボニル基;(m34) N‐(C1-C6)アルキルアミノスルホニル基;(m35) N,N‐ジ(C1-C6)アルキルアミノスルホニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);及び(m36) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基からなる。
置換基群Eは、
(n1) ハロゲン原子;(n2) シアノ基;(n3) ニトロ基;(n4) アミノ基;(n5) ヒドロキシル基;(n6) カルボキシル基;(n7) (C1-C6)アルキル基;(n8) (C1-C6)アルコキシ基;(n9) (C3-C6)シクロアルキル基;(n10) (C1-C6)アルキルスルファニル基;(n11) (C1-C6)アルキルスルフィニル基;(n12) (C1-C6)アルキルスルホニル基;(n13) ハロ(C1-C6)アルキル基;(n14) ハロ(C1-C6)アルコキシ基;(n15) ハロ(C3-C6)シクロアルキル基;(n16) ハロ(C1-C6)アルキルスルファニル基;(n17) ハロ(C1-C6)アルキルスルフィニル基;(n18) ハロ(C1-C6)アルキルスルホニル基;(n19) (C1-C6)アルキルカルボニルアミノ基;(n20) ハロ(C1-C6)アルキルカルボニルアミノ基;(n21) (C1-C6)アルキルスルホニルアミノ基;(n22) ハロ(C1-C6)アルキルスルホニルアミノ基;(n23) (C1-C6)アルコキシカルボニル基;(n24) N‐(C1-C6)アルキルアミノカルボニル基;(n25) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(n26) N‐ハロ(C1-C6)アルキルアミノカルボニル基;(n27) フェニル基;(n28) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(n29) ピラゾリル基;(n30) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(n31) フェノキシ基;(n32) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェノキシ基;(n33) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基;(n34) N‐(C1-C6)アルキルアミノスルホニル基;及び(n35) N,N‐ジ(C1-C6)アルキルアミノスルホニル基(当該(C1-C6)アルキルは、同一又は異なってもよい)からなる。
但し、R1の(a45)置換フェニル基、(a47)置換ピリジル基、(a49)置換ピリダジニル基、(a51)置換ピラジニル基、(a53)置換ピリミジニル基、(a55)置換オキサゾリル基、(a57)置換イソキサゾリル基、(a59)置換チエニル基、(a61)置換チアゾリル基、(a63)置換イソチアゾリル基、(a65)置換チアジアゾリル基、(a67)置換ピラゾリル基、(a69)置換トリアゾリル基、(a71)置換テトラゾリル基、及び(a73)置換ベンゾチアゾリル基は、アゼパン‐2,4‐ジオン環との結合原子の隣接原子に(C1-C6)アルキルスルホニル基、ハロ(C1-C6)アルキルスルホニル基、N‐(C1-C6)アルキルアミノスルホニル基、又はN,N‐ジ(C1-C6)アルキルアミノスルホニル基は置換しない。
}で表される化合物又はその塩類。 General formula (1)
R1 is
(a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 - C 6 ) cycloalkyl group; (a6) halo (C 1 - C 6 ) alkyl group; (a7) halo (C 2 - C 6 ) alkenyl group; (a8) halo (C 2 - C 6 ) alkynyl group (a9) halo(C 3 -C 6 )cycloalkyl group; (a10) substituted (C 1 -C 6 )alkyl group having 1 to 3 substituents each independently selected from substituent group A; (a11) Substituted (C 3 - C 6 ) cycloalkyl group having 1 to 3 substituents each independently selected from substituent group B; (a12) (C 1 -C 6 ) alkoxycarbonyl group; ( a13) N-(C 1 -C 6 )alkylaminocarbonyl group; (a14) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkyl groups are the same or different) (a15) phenylaminocarbonyl group; (a16) phenyl (C 1 -C 6 ) alkyl group; (a17) 1 to 5 substituents independently selected from substituent group C; Substituted phenyl (C 1 -C 6 ) alkyl group possessed above; (a18) Pyridyl (C 1 -C 6 ) alkyl group; (a19) 1 to 4 substituents each independently selected from Substituent Group C Substituted pyridyl (C 1 -C 6 ) alkyl group having on the ring; (a20) pyridazinyl (C 1 -C 6 ) alkyl group; (a21) 1 to 3 groups each independently selected from substituent group C; Substituted pyridazinyl (C 1 -C 6 ) alkyl group having a substituent on the ring; (a22) Pyrazinyl (C 1 -C 6 ) alkyl group; (a23) 1 to 3 each independently selected from substituent group C Substituted pyrazinyl (C 1 -C 6 ) alkyl group having 3 substituents on the ring; (a24) Pyrimidinyl (C 1 -C 6 ) alkyl group; (a25) 1 each independently selected from substituent group C; Substituted pyrimidinyl (C 1 -C 6 ) alkyl group having from 3 substituents on the ring; (a26) oxazolyl (C 1 -C 6 ) alkyl group; (a27) each independently selected from substituent group C; a substituted oxazolyl (C 1 -C 6 ) alkyl group having 1 or 2 substituents on the ring; (a28) an isoxazolyl (C 1 -C 6 ) alkyl group; (a29) each independently from substituent group C; Substituted isoxazolyl (C 1 -C 6 ) alkyl group having 1 or 2 selected substituents on the ring; (a30) Thienyl (C 1 -C 6 ) alkyl group; (a31) Each from substituent group C Substituted thienyl (C 1 -C 6 ) alkyl group having 1 to 3 independently selected substituents on the ring; (a32) Thiazolyl (C 1 -C 6 ) alkyl group; (a33) Substituent group C Substituted thiazolyl (C 1 -C 6 ) alkyl group having 1 or 2 substituents on the ring, each independently selected from; (a34) Isothiazolyl (C 1 -C 6 ) alkyl group; (a35) Substituent Substituted isothiazolyl (C 1 -C 6 ) alkyl group having 1 to 2 substituents independently selected from Group C on the ring; (a36) Thiadiazolyl (C 1 -C 6 ) alkyl group; (a37) Substituted thiadiazolyl (C 1 -C 6 ) alkyl group having one substituent selected from substituent group C on the ring; (a38) Pyrazolyl (C 1 -C 6 ) alkyl group; (a39) Substituent group Substituted pyrazolyl (C 1 -C 6 ) alkyl group having 1 to 3 substituents independently selected from C on the ring; (a40) Triazolyl (C 1 -C 6 ) alkyl group; (a41) Substituted Substituted triazolyl (C 1 -C 6 ) alkyl group having 1 or 2 substituents independently selected from group C on the ring; (a42) Tetrazolyl (C 1 -C 6 ) alkyl group; (a43) ) a substituted tetrazolyl (C 1 -C 6 ) alkyl group having one substituent selected from substituent group C on the ring; (a44) a phenyl group; (a45) each independently selected from substituent group D; Substituted phenyl group having 1 to 5 substituents on the ring; (a46) Pyridyl group; (a47) Substituted phenyl group having 1 to 4 substituents on the ring, each independently selected from Substituent Group D Pyridyl group; (a48) Pyridazinyl group; (a49) Substituted pyridazinyl group having 1 to 3 substituents on the ring, each independently selected from Substituent Group D; (a50) Pyrazinyl group; (a51) Substituent Substituted pyrazinyl group having 1 to 3 substituents each independently selected from Group D on the ring; (a52) Pyrimidinyl group; (a53) 1 to 3 substituents each independently selected from Substituent Group D Substituted pyrimidinyl group having a substituent on the ring; (a54) Oxazolyl group; (a55) Substituted oxazolyl group having one or two substituents on the ring, each independently selected from Substituent Group D; (a56) Isoxazolyl group; (a57) Substituted isoxazolyl group having 1 or 2 substituents on the ring each independently selected from Substituent Group D; (a58) Thienyl group; (a59) Each independently from Substituent Group D Substituted thienyl group having 1 to 3 selected substituents on the ring; (a60) Thiazolyl group; (a61) 1 to 2 substituents each independently selected from Substituent Group D on the ring a substituted thiazolyl group; (a62) an isothiazolyl group; (a63) a substituted isothiazolyl group having on its ring one or two substituents each independently selected from substituent group D; (a64) a thiadiazolyl group; (a65) Substituted thiadiazolyl group having one substituent selected from substituent group D on the ring; (a66) Pyrazolyl group; (a67) Substituted thiadiazolyl group having one to three substituents each independently selected from substituent group D Substituted pyrazolyl group having on the ring; (a68) Triazolyl group; (a69) Substituted triazolyl group having 1 to 2 substituents each independently selected from Substituent Group D on the ring; (a70) Tetrazolyl group; (a71) Substituted tetrazolyl group having one substituent selected from substituent group D on the ring; (a72) benzothiazolyl group; or (a73) 1 to 4 substituents selected from substituent group D represents a substituted benzothiazolyl group having on the ring.
R 2a is
(b1) A hydrogen atom; or (b2) a (C 1 -C 6 ) alkyl group.
R2b is
(c1) A hydrogen atom; or (c2) a (C 1 -C 6 ) alkyl group.
R 3a is
(d1) Hydrogen atom; (d2) (C 1 -C 6 ) alkyl group; (d3) Phenyl group; or (d4) Halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) Substituted phenyl having 1 to 5 substituents on the ring, each independently selected from the group consisting of an alkoxy group, a halo(C 1 -C 6 )alkyl group, and a halo(C 1 -C 6 )alkoxy group Indicates the group.
R 3b is
(e1) A hydrogen atom; or (e2) (C 1 -C 6 ) alkyl group.
R 4a is
(f1) Hydrogen atom; or (f2) (C 1 -C 6 ) alkyl group.
R 4b is
(g1) A hydrogen atom; or (g2) a (C 1 -C 6 ) alkyl group.
R5 is
(h1) (C 1 -C 6 ) alkyl group; (h2) (C 2 -C 6 ) alkenyl group; (h3) (C 2 -C 6 ) alkynyl group; (h4) (C 3 -C 6 ) cyclo Alkyl group; (h5) halo (C 1 - C 6 ) alkyl group; (h6) halo (C 2 - C 6 ) alkenyl group; (h7) halo (C 2 - C 6 ) alkynyl group; (h8) halo ( C 3 -C 6 ) cycloalkyl group; (h9) substituted (C 1 -C 6 ) alkyl group having 1 to 3 substituents each independently selected from substituent group A; (h10) substituent group Substituted (C 3 - C 6 ) cycloalkyl group having 1 to 3 substituents on the ring, each independently selected from B; (h11) phenyl group; (h12) each independently selected from substituent group E a substituted phenyl group having 1 to 5 substituents on the ring; (h13) a pyridyl group; (h14) having 1 to 4 substituents on the ring, each independently selected from substituent group E; Substituted pyridyl group; (h15) pyridazinyl group; (h16) substituted pyridazinyl group having 1 to 3 substituents on the ring, each independently selected from substituent group E; (h17) pyrimidinyl group; (h18) substituted Substituted pyrimidinyl group having 1 to 3 substituents each independently selected from group E on the ring; (h19) Pyrazinyl group; (h20) 1 to 3 substituents each independently selected from substituent group E Substituted pyrazinyl group having on the ring a substituent; (h21) Triazinyl group; (h22) Substituted triazinyl group having one or two substituents on the ring, each independently selected from substituent group E; (h23) ) Furanyl group; (h24) Substituted furanyl group having 1 to 3 substituents on the ring, each independently selected from Substituent Group E; (h25) Oxazolyl group; (h26) Each independently from Substituent Group E Substituted oxazolyl group having 1 to 2 substituents selected on the ring; (h27) Isoxazolyl group; (h29) a thienyl group; (h30) a substituted thienyl group having on its ring 1 to 3 substituents each independently selected from substituent group E; (h31) a thiazolyl group; (h32) ) Substituted thiazolyl group having 1 to 2 substituents on the ring, each independently selected from substituent group E; (h33) Isothiazolyl group; (h34) 1 to 2 each independently selected from substituent group E Substituted isothiazolyl group having two substituents on the ring; (h35) Thiadiazolyl group; (h36) Substituted thiadiazolyl group having one substituent selected from Substituent Group E on the ring; (h37) Pyrazolyl group (h38) Substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from substituent group E; (h39) Triazolyl group; (h40) Substituted pyrazolyl group, each independently selected from substituent group E Substituted triazolyl group having one or two substituents on the ring; (h41) Tetrazolyl group; (h42) Substituted tetrazolyl group having one substituent selected from substituent group E on the ring; (h43) ) Benzoxazolyl group; (h44) Substituted benzoxazolyl group having 1 to 4 substituents on the ring, each independently selected from Substituent Group E; (h45) Benzothiazolyl group; (h46) Substituted Substituted benzothiazolyl group having 1 to 4 substituents each independently selected from group E on the ring; (h47) Quinolinyl group; (h48) 1 to 6 substituents each independently selected from substituent group E Substituted quinolinyl group having on the ring a substituent; (h49) Naphthyl group; (h50) Substituted naphthyl group having 1 to 7 substituents on the ring, each independently selected from substituent group E; (h51 ) Tetrahydronaphthyl group; (h52) Substituted tetrahydronaphthyl group having 1 to 10 substituents on the ring, each independently selected from Substituent Group E; (h53) Phenyl (C 1 -C 6 ) alkyl group; (h54) Substituted phenyl (C 1 -C 6 ) alkyl group having 1 to 5 substituents on the ring, each independently selected from substituent group E; (h55) Pyridyl (C 1 -C 6 ) alkyl group Group; (h56) Substituted pyridyl (C 1 -C 6 ) alkyl group having on the ring 1 to 4 substituents each independently selected from Substituent Group E; (h57) Pyridazinyl (C 1 -C 6 ) alkyl group; (h58) substituted pyridazinyl (C 1 -C 6 ) alkyl group having on the ring 1 to 3 substituents each independently selected from substituent group E; (h59) pyrazinyl (C 1 - C 6 ) alkyl group; (h60) substituted pyrazinyl (C 1 -C 6 ) alkyl group having on the ring 1 to 3 substituents each independently selected from substituent group E; (h61) pyrimidinyl (C 1 -C 6 ) alkyl group; or (h62) represents a substituted pyrimidinyl (C 1 -C 6 ) alkyl group having 1 to 3 substituents independently selected from substituent group E on the ring.
R6 is
(i1) Hydrogen atom; (i2) (C 1 -C 6 ) alkyl group; (i3) (C 3 -C 6 ) cycloalkyl group; (i4) (C 1 -C 6 ) alkoxy group; or (i5) (C 1 -C 6 ) represents an alkylcarbonyl group.
X is a hydroxyl group, a (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 )alkylsulfanyl group, a (C 1 -C 6 )alkylsulfinyl group, or a (C 1 -C 6 )alkylsulfonyl group. show.
Y is an oxygen atom, a sulfur atom, or an NR 7 group (wherein R 7 is a hydrogen atom, a (C 1 -C 6 ) alkyl group, or a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group) , and a halo(C 1 -C 6 )alkyl group, each having 1 to 4 substituents on the ring.
Substituent group A is
(j1) Cyano group; (j2) (C 1 -C 6 ) alkyl group; (j3) (C 2 -C 6 ) alkenyl group; (j4) (C 2 -C 6 ) alkynyl group; (j5) (C 3 - C6 ) cycloalkyl group; (j6) ( C1 - C6 ) alkoxy group; (j7) ( C1 - C6 ) alkylsulfanyl group; (j8) ( C1 - C6 ) alkylsulfinyl group; (j9) (C 1 -C 6 )alkylsulfonyl group; (j10) Halo (C 1 -C 6 ) alkyl group; (j11) Halo (C 2 -C 6 ) alkenyl group; (j12) Halo (C 2 - C 6 ) alkynyl group; (j13) halo(C 3 -C 6 )cycloalkyl group; (j14) halo(C 1 -C 6 )alkoxy group; (j15) halo(C 1 -C 6 )alkylsulfanyl group; (j16) halo(C 1 -C 6 )alkylsulfinyl group; (j17) halo(C 1 -C 6 )alkylsulfonyl group; (j18) (C 1 -C 6 )alkoxycarbonyl group; and (j19) halo( C 1 -C 6 ) alkoxycarbonyl group.
Substituent group B is
(k1) Cyano group; (k2) (C 1 -C 6 ) alkyl group; (k3) (C 2 -C 6 ) alkenyl group; (k4) (C 2 -C 6 ) alkynyl group; (k5) (C 3 - C6 ) cycloalkyl group; (k6) ( C1 - C6 ) alkoxy group; (k7) ( C1 - C6 ) alkylsulfanyl group; (k8) ( C1 - C6 ) alkylsulfinyl group; (k9) (C 1 - C 6 ) alkylsulfonyl group; (k10) halo (C 1 - C 6 ) alkyl group; (k11) halo (C 3 - C 6 ) cycloalkyl group; (k12) halo (C 1 -C 6 ) alkoxy group; (k13) halo(C 1 -C 6 )alkylsulfanyl group; (k14) halo(C 1 -C 6 )alkylsulfinyl group; (k15) halo(C 1 -C 6 )alkylsulfonyl and (k16) a phenyl group.
Substituent group C is
(l1) Halogen atom; (l2) Cyano group; (l3) Nitro group; (l4) Hydroxyl group; (l5) Carboxyl group; (l6) (C 1 - C 6 ) alkyl group; (l7) (C 2 - C 6 ) alkenyl group; (l8) (C 2 -C 6 ) alkynyl group; (l9) (C 1 -C 6 ) alkoxy group; (l10) (C 3 -C 6 ) cycloalkyl group; (l11) ( C 1 -C 6 )alkylsulfanyl group; (l12) (C 1 -C 6 )alkylsulfinyl group; (l13) (C 1 -C 6 )alkylsulfonyl group; (l14) halo(C 1 -C 6 )alkyl Group; (l15) Halo (C 2 - C 6 ) alkenyl group; (l16) Halo (C 2 - C 6 ) alkynyl group; (l17) Halo (C 1 - C 6 ) alkoxy group; (l18) Halo (C 3 -C 6 )cycloalkyl group; (l19) halo(C 1 -C 6 )alkylsulfanyl group; (l20) halo(C 1 -C 6 )alkylsulfinyl group; (l21) halo(C 1 -C 6 ) Alkylsulfonyl group; (l22) (C 1 - C 6 ) alkylcarbonyl group; (l23) (C 1 - C 6 ) alkoxycarbonyl group; (l24) (C 1 - C 6 ) alkylcarbonylamino group; (l25) Halo(C 1 -C 6 )alkylcarbonylamino group; (l26) (C 1 -C 6 )alkylsulfonylamino group; (l27) Halo(C 1 -C 6 )alkylsulfonylamino group; (l28) N-( C 1 -C 6 ) alkylaminocarbonyl group; (l29) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 ) alkyl groups may be the same or different); (l30) N-halo(C 1 -C 6 )alkylaminocarbonyl group; (l31) N-(C 1 -C 6 )alkylaminosulfonyl group; and (l32) N,N-di(C 1 -C 6 ) alkylaminosulfonyl group (the (C 1 -C 6 )alkyl groups may be the same or different).
Substituent group D is
(m1) Halogen atom; (m2) Cyano group; (m3) Nitro group; (m4) Amino group; (m5) Hydroxyl group; (m6) Carboxyl group; (m7) (C 1 - C 6 ) alkyl group; ( m8) (C 2 - C 6 ) alkenyl group; (m9) (C 2 - C 6 ) alkynyl group; (m10) (C 1 - C 6 ) alkoxy group; (m11) (C 3 - C 6 ) cycloalkyl Group; (m12) (C 1 -C 6 )alkylsulfanyl group; (m13) (C 1 -C 6 )alkylsulfinyl group; (m14) (C 1 -C 6 )alkylsulfonyl group; (m15) Halo (C 1 - C 6 ) alkyl group; (m16) halo (C 2 - C 6 ) alkenyl group; (m17) halo (C 2 - C 6 ) alkynyl group; (m18) halo (C 1 - C 6 ) alkoxy group; (m19) Halo(C 3 -C 6 )cycloalkyl group; (m20) Halo(C 1 -C 6 )alkylsulfanyl group; (m21) Halo(C 1 -C 6 )alkylsulfinyl group; (m22) Halo( C 1 -C 6 )alkylsulfonyl group; (m23) cyano group, (C 1 -C 6 ) alkyl group, halo (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group and (C 1 Substituted (C 3 -C 6 ) cycloalkyl group having on the ring 1 to 3 substituents each independently selected from the group consisting of -C 6 ) alkylcarbonyl group; (m24) (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (m25) (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkoxy group; (m26) (C 1 -C 6 ) alkylcarbonylamino group; (m27 ) Halo(C 1 -C 6 )alkylcarbonylamino group; (m28) (C 1 -C 6 )alkylsulfonylamino group; (m29) Halo(C 1 -C 6 )alkylsulfonylamino group; (m30) (C 1 -C 6 )alkoxycarbonyl group; (m31) N-(C 1 -C 6 )alkylaminocarbonyl group; (m32) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkylaminocarbonyl group; -C 6 ) alkyl may be the same or different); (m33) N-halo(C 1 -C 6 ) alkylaminocarbonyl group; (m34) N-(C 1 -C 6 ) alkylaminosulfonyl group; (m35) N,N-di(C 1 -C 6 )alkylaminosulfonyl group (the (C 1 -C 6 )alkyl groups may be the same or different); and (m36) two adjacent substitutions The group consists of a methylenedioxy group which is optionally substituted with one or two substituents selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group.
The substituent group E is
(n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n4) Amino group; (n5) Hydroxyl group; (n6) Carboxyl group; (n7) (C 1 - C 6 ) alkyl group; ( n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 - C 6 ) cycloalkyl group; (n10) (C 1 - C 6 ) alkylsulfanyl group; (n11) (C 1 - C 6 ) Alkylsulfinyl group; (n12) (C 1 - C 6 ) alkyl sulfonyl group; (n13) halo (C 1 - C 6 ) alkyl group; (n14) halo (C 1 - C 6 ) alkoxy group; (n15) halo (C 3 - C 6 ) cycloalkyl group; (n16) halo (C 1 - C 6 ) alkylsulfanyl group; (n17) halo (C 1 - C 6 ) alkyl sulfinyl group; (n18) halo (C 1 - C 6 ) Alkylsulfonyl group; (n19) (C 1 - C 6 ) alkylcarbonylamino group; (n20) Halo (C 1 - C 6 ) alkylcarbonylamino group; (n21) (C 1 - C 6 ) alkylsulfonylamino group Group; (n22) Halo(C 1 -C 6 )alkylsulfonylamino group; (n23) (C 1 -C 6 ) alkoxycarbonyl group; (n24) N-(C 1 -C 6 )alkylaminocarbonyl group; ( n25) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkyl groups may be the same or different); (n26) N-halo(C 1 -C 6 ) alkylaminocarbonyl group; (n27) phenyl group; (n28) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkyl Substituted phenyl group having 1 to 5 substituents on the ring each independently selected from the group consisting of C 1 - C 6 alkoxy groups; (n29) pyrazolyl group; (n30) halogen atom, each independently from the group consisting of a cyano group, a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group, a halo(C 1 -C 6 )alkyl group and a halo(C 1 -C 6 )alkoxy group; Substituted pyrazolyl group having 1 to 3 substituents selected on the ring; (n31) Phenoxy group; (n32) Halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) Substituted phenoxy having 1 to 5 substituents on the ring, each independently selected from the group consisting of an alkoxy group, a halo(C 1 -C 6 )alkyl group, and a halo(C 1 -C 6 )alkoxy group Group; (n33) Substituted with one or two substituents selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group formed by two adjacent substituents together. optional methylenedioxy group; (n34) N-(C 1 -C 6 ) alkylaminosulfonyl group; and (n35) N,N-di(C 1 -C 6 )alkylaminosulfonyl group (the (C 1 -C 6 )alkyl may be the same or different).
However, R 1 's (a45) substituted phenyl group, (a47) substituted pyridyl group, (a49) substituted pyridazinyl group, (a51) substituted pyrazinyl group, (a53) substituted pyrimidinyl group, (a55) substituted oxazolyl group, (a57) Substituted isoxazolyl group, (a59) substituted thienyl group, (a61) substituted thiazolyl group, (a63) substituted isothiazolyl group, (a65) substituted thiadiazolyl group, (a67) substituted pyrazolyl group, (a69) substituted triazolyl group, (a71) substituted Tetrazolyl group and (a73) substituted benzothiazolyl group have a (C 1 -C 6 )alkylsulfonyl group or a halo(C 1 -C 6 )alkylsulfonyl group on the atom adjacent to the atom bonded to the azepane-2,4-dione ring. , N-(C 1 -C 6 )alkylaminosulfonyl group, or N,N-di(C 1 -C 6 )alkylaminosulfonyl group is not substituted.
} or its salts. - R1が、
(a1) 水素原子;(a2) (C1-C6)アルキル基;(a3) (C2-C6)アルケニル基;(a4) (C2-C6)アルキニル基;(a5) (C3-C6)シクロアルキル基;(a6) ハロ(C1-C6)アルキル基;(a10) 置換基群Aからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C1-C6)アルキル基;(a12) (C1-C6)アルコキシカルボニル基;(a14) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(a15) フェニルアミノカルボニル基;(a16) フェニル(C1-C6)アルキル基;(a17) 置換基群Cからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基;(a18) ピリジル(C1-C6)アルキル基;(a19) 置換基群Cからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル(C1-C6)アルキル基;(a24) ピリミジニル(C1-C6)アルキル基;(a25) 置換基群Cからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル(C1-C6)アルキル基;(a26) オキサゾリル(C1-C6)アルキル基;(a27) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル(C1-C6)アルキル基;(a36) チアジアゾリル(C1-C6)アルキル基;(a37) 置換基群Cから選択される1個の置換基を環上に有する置換チアジアゾリル(C1-C6)アルキル基;(a40) トリアゾリル(C1-C6)アルキル基;(a41) 置換基群Cからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル(C1-C6)アルキル基;(a44) フェニル基;(a45) 置換基群Dからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(a46) ピリジル基;(a47) 置換基群Dからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(a50) ピラジニル基;(a51) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル基;(a52) ピリミジニル基;(a53) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(a54) オキサゾリル基;(a55) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル基;(a60) チアゾリル基;(a61) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(a64) チアジアゾリル基;(a65) 置換基群Dから選択される1個の置換基を環上に有する置換チアジアゾリル基;(a66) ピラゾリル基;(a67) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(a68) トリアゾリル基;(a69) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル基;(a72) ベンゾチアゾリル基;又は(a73) 置換基群Dから選択される1乃至4個の置換基を環上に有する置換ベンゾチアゾリル基であり、
R2aが、(b1) 水素原子であり、
R2bが、(c1) 水素原子であり、
R3aが、
(d1) 水素原子;(d2) (C1-C6)アルキル基;(d3) フェニル基;又は(d4) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基であり、
R3bが、
(e1) 水素原子;又は(e2) (C1-C6)アルキル基であり、
R4aが、
(f1) 水素原子;又は(f2) (C1-C6)アルキル基であり、
R4bが、
(g1) 水素原子;又は(g2) (C1-C6)アルキル基であり、
R5が、
(h1) (C1-C6)アルキル基;(h3) (C2-C6)アルキニル基;(h4) (C3-C6)シクロアルキル基;(h5) ハロ(C1-C6)アルキル基;(h11) フェニル基;(h12) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(h13) ピリジル基;(h14) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(h15) ピリダジニル基;(h16) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル基;(h17) ピリミジニル基;(h18) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(h19) ピラジニル基;(h20) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラジニル基;(h25) オキサゾリル基;(h26) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換オキサゾリル基;(h27) イソキサゾリル基;(h28) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル基;(h31) チアゾリル基;(h32) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(h41) テトラゾリル基;(h42) 置換基群Eから選択される1個の置換基を環上に有する置換テトラゾリル基;(h53) フェニル(C1-C6)アルキル基;又は(h54) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基であり、
R6が、
(i1) 水素原子;又は(i2) (C1-C6)アルキル基であり、
Xが、ヒドロキシル基、(C1-C6)アルコキシ基、(C1-C6)アルキルスルファニル基、(C1-C6)アルキルスルフィニル基、又は(C1-C6)アルキルスルホニル基であり、
Yが、酸素原子、硫黄原子、又はNR7基(式中、R7は、ハロゲン原子、シアノ基、(C1-C6)アルキル基、及びハロ(C1-C6)アルキル基からなる群からそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基を示す。)であり、
置換基群Aが、
(j1) シアノ基;(j5) (C3-C6)シクロアルキル基;(j6) (C1-C6)アルコキシ基;(j7) (C1-C6)アルキルスルファニル基;(j8) (C1-C6)アルキルスルフィニル基;(j9) (C1-C6)アルキルスルホニル基;及び(j18) (C1-C6)アルコキシカルボニル基からなり、
置換基群Cが、
(l1) ハロゲン原子;(l2) シアノ基;(l3) ニトロ基;(l6) (C1-C6)アルキル基;(l9) (C1-C6)アルコキシ基;(l11) (C1-C6)アルキルスルファニル基;(l12) (C1-C6)アルキルスルフィニル基;(l13) (C1-C6)アルキルスルホニル基;(l14) ハロ(C1-C6)アルキル基;(l17) ハロ(C1-C6)アルコキシ基;(l19) ハロ(C1-C6)アルキルスルファニル基;(l20) ハロ(C1-C6)アルキルスルフィニル基;(l21) ハロ(C1-C6)アルキルスルホニル基;(l23) (C1-C6)アルコキシカルボニル基;(l24) (C1-C6)アルキルカルボニルアミノ基;(l25) ハロ(C1-C6)アルキルカルボニルアミノ基;(l26) (C1-C6)アルキルスルホニルアミノ基;(l27) ハロ(C1-C6)アルキルスルホニルアミノ基;(l28) N‐(C1-C6)アルキルアミノカルボニル基;(l29) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);及び(l30) N‐ハロ(C1-C6)アルキルアミノカルボニル基からなり、
置換基群Dが、
(m1) ハロゲン原子;(m2) シアノ基;(m3) ニトロ基;(m7) (C1-C6)アルキル基;(m10) (C1-C6)アルコキシ基;(m12) (C1-C6)アルキルスルファニル基;(m13) (C1-C6)アルキルスルフィニル基;(m14) (C1-C6)アルキルスルホニル基;(m15) ハロ(C1-C6)アルキル基;(m18) ハロ(C1-C6)アルコキシ基;(m20) ハロ(C1-C6)アルキルスルファニル基;(m21) ハロ(C1-C6)アルキルスルフィニル基;(m22) ハロ(C1-C6)アルキルスルホニル基;(m26) (C1-C6)アルキルカルボニルアミノ基;(m27) ハロ(C1-C6)アルキルカルボニルアミノ基;(m28) (C1-C6)アルキルスルホニルアミノ基;(m29) ハロ(C1-C6)アルキルスルホニルアミノ基;(m30) (C1-C6)アルコキシカルボニル基;(m31) N‐(C1-C6)アルキルアミノカルボニル基;(m32) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(m33) N‐ハロ(C1-C6)アルキルアミノカルボニル基;及び(m36) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基からなり、
置換基群Eが、
(n1) ハロゲン原子;(n2) シアノ基;(n3) ニトロ基;(n7) (C1-C6)アルキル基;(n8) (C1-C6)アルコキシ基;(n9) (C3-C6)シクロアルキル基;(n10) (C1-C6)アルキルスルファニル基;(n11) (C1-C6)アルキルスルフィニル基;(n12) (C1-C6)アルキルスルホニル基;(n13) ハロ(C1-C6)アルキル基;(n14) ハロ(C1-C6)アルコキシ基;(n16) ハロ(C1-C6)アルキルスルファニル基;(n17) ハロ(C1-C6)アルキルスルフィニル基;(n18) ハロ(C1-C6)アルキルスルホニル基;(n19) (C1-C6)アルキルカルボニルアミノ基;(n20) ハロ(C1-C6)アルキルカルボニルアミノ基;(n21) (C1-C6)アルキルスルホニルアミノ基;(n22) ハロ(C1-C6)アルキルスルホニルアミノ基;(n23) (C1-C6)アルコキシカルボニル基;(n24) N‐(C1-C6)アルキルアミノカルボニル基;(n25) N,N‐ジ(C1-C6)アルキルアミノカルボニル基(当該(C1-C6)アルキルは、同一又は異なってもよい);(n26) N‐ハロ(C1-C6)アルキルアミノカルボニル基;(n27) フェニル基;(n28) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(n29) ピラゾリル基;(n30) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(n31) フェノキシ基;(n32) ハロゲン原子、シアノ基、(C1-C6)アルキル基、(C1-C6)アルコキシ基、ハロ(C1-C6)アルキル基及びハロ(C1-C6)アルコキシ基からなる群からそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェノキシ基;(n33) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基;(n34) N‐(C1-C6)アルキルアミノスルホニル基;及び(n35) N,N‐ジ(C1-C6)アルキルアミノスルホニル基(当該(C1-C6)アルキルは、同一又は異なってもよい)からなる、請求項1に記載の化合物又はその塩類。 R 1 is
(a1) Hydrogen atom; (a2) (C 1 -C 6 ) alkyl group; (a3) (C 2 -C 6 ) alkenyl group; (a4) (C 2 -C 6 ) alkynyl group; (a5) (C 3 -C 6 )cycloalkyl group; (a6) halo(C 1 -C 6 )alkyl group; (a10) substituted (C 1 ) having 1 to 3 substituents each independently selected from substituent group A; -C 6 ) alkyl group; (a12) (C 1 -C 6 ) alkoxycarbonyl group; (a14) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 ) alkyl group may be the same or different); (a15) phenylaminocarbonyl group; (a16) phenyl (C 1 -C 6 ) alkyl group; (a17) 1 to 5 groups each independently selected from substituent group C Substituted phenyl (C 1 -C 6 ) alkyl group having a substituent on the ring; (a18) Pyridyl (C 1 -C 6 ) alkyl group; (a19) 1 to 1 each independently selected from substituent group C; Substituted pyridyl (C 1 -C 6 ) alkyl group having 4 substituents on the ring; (a24) Pyrimidinyl (C 1 -C 6 ) alkyl group; (a25) each independently selected from substituent group C Substituted pyrimidinyl (C 1 -C 6 ) alkyl group having 1 to 3 substituents on the ring; (a26) Oxazolyl (C 1 -C 6 ) alkyl group; (a27) each independently selected from substituent group C a substituted oxazolyl (C 1 -C 6 ) alkyl group having 1 or 2 substituents on the ring; (a36) a thiadiazolyl (C 1 -C 6 ) alkyl group; (a37) a substituted oxazolyl (C 1 -C 6 ) alkyl group selected from substituent group C; a substituted thiadiazolyl (C 1 -C 6 ) alkyl group having one substituent on the ring; (a40) a triazolyl (C 1 -C 6 ) alkyl group; (a41) each independently selected from substituent group C; a substituted triazolyl (C 1 -C 6 ) alkyl group having 1 to 2 substituents on the ring; (a44) a phenyl group; (a45) 1 to 5 substituents each independently selected from substituent group D; Substituted phenyl group having a substituent on the ring; (a46) Pyridyl group; (a47) Substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from substituent group D; (a50) Pyrazinyl group; (a51) substituted pyrazinyl group having 1 to 3 substituents on the ring each independently selected from substituent group D; (a52) pyrimidinyl group; (a53) each independently from substituent group D Substituted pyrimidinyl group having 1 to 3 selected substituents on the ring; (a54) Oxazolyl group; (a55) 1 to 2 substituents each independently selected from Substituent Group D on the ring (a60) a thiazolyl group; (a61) a substituted thiazolyl group having on its ring one or two substituents each independently selected from substituent group D; (a64) a thiadiazolyl group; (a65) Substituted thiadiazolyl group having one substituent selected from substituent group D on the ring; (a66) Pyrazolyl group; (a67) Substituted thiadiazolyl group having one to three substituents each independently selected from substituent group D Substituted pyrazolyl group having on the ring; (a68) Triazolyl group; (a69) Substituted triazolyl group having 1 or 2 substituents each independently selected from Substituent Group D on the ring; (a72) Benzothiazolyl group; or (a73) a substituted benzothiazolyl group having 1 to 4 substituents selected from substituent group D on the ring;
R 2a is (b1) a hydrogen atom,
R 2b is (c1) a hydrogen atom,
R 3a is
(d1) Hydrogen atom; (d2) (C 1 -C 6 ) alkyl group; (d3) Phenyl group; or (d4) Halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) Substituted phenyl having 1 to 5 substituents on the ring, each independently selected from the group consisting of an alkoxy group, a halo(C 1 -C 6 )alkyl group, and a halo(C 1 -C 6 )alkoxy group is the basis,
R 3b is
(e1) a hydrogen atom; or (e2) a (C 1 -C 6 ) alkyl group,
R 4a is
(f1) a hydrogen atom; or (f2) a (C 1 -C 6 ) alkyl group,
R 4b is
(g1) a hydrogen atom; or (g2) a (C 1 -C 6 ) alkyl group,
R5 is
(h1) (C 1 -C 6 ) alkyl group; (h3) (C 2 -C 6 ) alkynyl group; (h4) (C 3 -C 6 ) cycloalkyl group; (h5) halo (C 1 -C 6 ) ) Alkyl group; (h11) phenyl group; (h12) substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from substituent group E; (h13) pyridyl group; (h14) substituted Substituted pyridyl group having 1 to 4 substituents each independently selected from group E on the ring; (h15) Pyridazinyl group; (h16) 1 to 3 substituents each independently selected from substituent group E Substituted pyrimidinyl group having on the ring a substituent; (h17) Pyrimidinyl group; (h18) Substituted pyrimidinyl group having 1 to 3 substituents on the ring, each independently selected from substituent group E; (h19) ) Pyrazinyl group; (h20) Substituted pyrazinyl group having 1 to 3 substituents on the ring each independently selected from substituent group E; (h25) oxazolyl group; (h26) each independently from substituent group E Substituted oxazolyl group having 1 to 2 substituents selected on the ring; (h27) Isoxazolyl group; (h31) a thiazolyl group; (h32) a substituted thiazolyl group having on its ring one or two substituents each independently selected from substituent group E; (h41) a tetrazolyl group; (h42) ) Substituted tetrazolyl group having one substituent selected from substituent group E on the ring; (h53) phenyl (C 1 - C 6 ) alkyl group; or (h54) each independently selected from substituent group E a substituted phenyl (C 1 -C 6 ) alkyl group having 1 to 5 substituents on the ring,
R 6 is
(i1) a hydrogen atom; or (i2) a (C 1 -C 6 ) alkyl group,
X is a hydroxyl group, a (C 1 -C 6 ) alkoxy group, a (C 1 -C 6 )alkylsulfanyl group, a (C 1 -C 6 )alkylsulfinyl group, or a (C 1 -C 6 )alkylsulfonyl group; can be,
Y is an oxygen atom, a sulfur atom, or a NR 7 group (wherein R 7 is a halogen atom, a cyano group, a (C 1 -C 6 ) alkyl group, and a halo(C 1 -C 6 ) alkyl group) (represents a substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from the group),
Substituent group A is
(j1) Cyano group; (j5) (C 3 - C 6 ) cycloalkyl group; (j6) (C 1 - C 6 ) alkoxy group; (j7) (C 1 - C 6 ) alkylsulfanyl group; (j8) (C 1 -C 6 )alkylsulfinyl group; (j9) (C 1 -C 6 )alkylsulfonyl group; and (j18) (C 1 -C 6 )alkoxycarbonyl group,
Substituent group C is
(l1) Halogen atom; (l2) Cyano group; (l3) Nitro group; (l6) (C 1 -C 6 ) alkyl group; (l9) (C 1 -C 6 ) alkoxy group; (l11) (C 1 -C 6 ) alkylsulfanyl group; (l12) (C 1 -C 6 ) alkylsulfinyl group; (l13) (C 1 -C 6 ) alkylsulfonyl group; (l14) halo(C 1 -C 6 ) alkyl group; (l17) Halo(C 1 -C 6 )alkoxy group; (l19) Halo(C 1 -C 6 )alkylsulfanyl group; (l20) Halo(C 1 -C 6 )alkylsulfinyl group; (l21) Halo(C 1 - C 6 ) alkylsulfonyl group; (l23) (C 1 - C 6 ) alkoxycarbonyl group; (l24) (C 1 - C 6 ) alkylcarbonylamino group; (l25) halo(C 1 -C 6 ) alkyl Carbonylamino group; (l26) (C 1 - C 6 ) alkylsulfonylamino group; (l27) Halo (C 1 - C 6 ) alkylsulfonylamino group; (l28) N-(C 1 -C 6 ) alkylaminocarbonyl group; (l29) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkyl groups may be the same or different); and (l30) N-halo(C 1 -C 6 )alkylaminocarbonyl group,
The substituent group D is
(m1) Halogen atom; (m2) Cyano group; (m3) Nitro group; (m7) (C 1 - C 6 ) alkyl group; (m10) (C 1 - C 6 ) alkoxy group; (m12) (C 1 -C 6 ) alkylsulfanyl group; (m13) (C 1 -C 6 ) alkylsulfinyl group; (m14) (C 1 -C 6 ) alkylsulfonyl group; (m15) halo(C 1 -C 6 ) alkyl group; (m18) Halo(C 1 -C 6 )alkoxy group; (m20) Halo(C 1 -C 6 )alkylsulfanyl group; (m21) Halo(C 1 -C 6 )alkylsulfinyl group; (m22) Halo(C 1 - C 6 ) alkylsulfonyl group; (m26) (C 1 - C 6 ) alkylcarbonylamino group; (m27) halo (C 1 - C 6 ) alkylcarbonylamino group; (m28) (C 1 - C 6 ) Alkylsulfonylamino group; (m29) Halo(C 1 -C 6 )alkylsulfonylamino group; (m30) (C 1 -C 6 ) alkoxycarbonyl group; (m31) N-(C 1 -C 6 )alkylaminocarbonyl Group; (m32) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 ) alkyls may be the same or different); (m33) N-halo(C 1 -C 6 ) alkylaminocarbonyl group; and (m36) 1 to 1 selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group formed by two adjacent substituents together; Consists of a methylenedioxy group which may be substituted with two substituents,
The substituent group E is
(n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n7) (C 1 - C 6 ) alkyl group; (n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 -C 6 ) cycloalkyl group; (n10) (C 1 -C 6 ) alkylsulfanyl group; (n11) (C 1 -C 6 ) alkylsulfinyl group; (n12) (C 1 -C 6 ) alkylsulfonyl group; (n13) Halo (C 1 - C 6 ) alkyl group; (n14) Halo (C 1 - C 6 ) alkoxy group; (n16) Halo (C 1 - C 6 ) alkylsulfanyl group; (n17) Halo (C 1 -C 6 ) alkylsulfinyl group; (n18) halo(C 1 -C 6 )alkylsulfonyl group; (n19) (C 1 -C 6 ) alkylcarbonylamino group; (n20) halo(C 1 -C 6 ) alkyl Carbonylamino group; (n21) (C 1 - C 6 ) alkylsulfonylamino group; (n22) Halo (C 1 - C 6 ) alkylsulfonylamino group; (n23) (C 1 - C 6 ) alkoxycarbonyl group; ( n24) N-(C 1 -C 6 )alkylaminocarbonyl group; (n25) N,N-di(C 1 -C 6 )alkylaminocarbonyl group (the (C 1 -C 6 )alkyl groups may be the same or different) (n26) N-halo(C 1 -C 6 )alkylaminocarbonyl group; (n27) Phenyl group; (n28) Halogen atom, cyano group, (C 1 -C 6 )alkyl group, (C 1 to 5 substituents each independently selected from the group consisting of a 1 -C 6 ) alkoxy group, a halo (C 1 -C 6 ) alkyl group, and a halo (C 1 -C 6 ) alkoxy group on the ring; Substituted phenyl group having; (n29) pyrazolyl group; (n30) halogen atom, cyano group, (C 1 -C 6 ) alkyl group, (C 1 -C 6 ) alkoxy group, halo (C 1 -C 6 ) alkyl group and a substituted pyrazolyl group having 1 to 3 substituents on the ring, each independently selected from the group consisting of a halo(C 1 -C 6 ) alkoxy group; (n31) a phenoxy group; (n32) a halogen atom, a cyano atom; each independently from the group consisting of a (C 1 -C 6 )alkyl group, a (C 1 -C 6 )alkoxy group, a halo(C 1 -C 6 )alkyl group and a halo(C 1 -C 6 )alkoxy group; Substituted phenoxy group having 1 to 5 selected substituents on the ring; (n33) Halogen atom and (C 1 -C 6 ) alkyl group formed by two adjacent substituents together a methylenedioxy group which may be substituted with one or two substituents selected from the group consisting of; (n34) N-(C 1 -C 6 ) alkylaminosulfonyl group; and (n35) N,N- The compound or salt thereof according to claim 1, which consists of a di(C 1 -C 6 )alkylaminosulfonyl group (the (C 1 -C 6 )alkyl groups may be the same or different). - R1が、
(a1) 水素原子;(a3) (C2-C6)アルケニル基;(a6) ハロ(C1-C6)アルキル基;(a10) 置換基群Aからそれぞれ独立に選択される1乃至3個の置換基を有する置換(C1-C6)アルキル基;(a16) フェニル(C1-C6)アルキル基;(a17) 置換基群Cからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル(C1-C6)アルキル基;(a18) ピリジル(C1-C6)アルキル基;(a44) フェニル基;(a45) 置換基群Dからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(a46) ピリジル基;(a47) 置換基群Dからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(a50) ピラジニル基;(a61) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換チアゾリル基;(a64) チアジアゾリル基;(a67) 置換基群Dからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピラゾリル基;(a69) 置換基群Dからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換トリアゾリル基;又は(a72) ベンゾチアゾリル基であり、
R2aが、(b1) 水素原子であり、
R2bが、(c1) 水素原子であり、
R3aが、
(d1) 水素原子;又は(d2) (C1-C6)アルキル基であり、
R3bが、
(e1) 水素原子;又は(e2) (C1-C6)アルキル基であり、
R4aが、(f1) 水素原子であり、
R4bが、(g1) 水素原子であり、
R5が、
(h1) (C1-C6)アルキル基;(h11) フェニル基;(h12) 置換基群Eからそれぞれ独立に選択される1乃至5個の置換基を環上に有する置換フェニル基;(h13) ピリジル基;(h14) 置換基群Eからそれぞれ独立に選択される1乃至4個の置換基を環上に有する置換ピリジル基;(h15) ピリダジニル基;(h16) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリダジニル基;(h18) 置換基群Eからそれぞれ独立に選択される1乃至3個の置換基を環上に有する置換ピリミジニル基;(h19) ピラジニル基;(h25) オキサゾリル基;(h28) 置換基群Eからそれぞれ独立に選択される1乃至2個の置換基を環上に有する置換イソキサゾリル基;(h31) チアゾリル基;(h42) 置換基群Eから選択される1個の置換基を環上に有する置換テトラゾリル基;又は(h53) フェニル(C1-C6)アルキル基であり、
R6が、(i1) 水素原子であり、
Xが、ヒドロキシル基であり、
Yが、酸素原子、又は硫黄原子であり、
置換基群Aが、(j5) (C3-C6)シクロアルキル基であり、
置換基群Cが、
(l1) ハロゲン原子;(l2) シアノ基;(l9) (C1-C6)アルコキシ基;(l11) (C1-C6)アルキルスルファニル基;(l14) ハロ(C1-C6)アルキル基;(l17) ハロ(C1-C6)アルコキシ基;(l19) ハロ(C1-C6)アルキルスルファニル基;及び(l20) ハロ(C1-C6)アルキルスルフィニル基からなり、
置換基群Dが、
(m7) (C1-C6)アルキル基;(m15) ハロ(C1-C6)アルキル基;(m18) ハロ(C1-C6)アルコキシ基;(m20) ハロ(C1-C6)アルキルスルファニル基;及び(m36) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基からなり、
置換基群Eが、
(n1) ハロゲン原子;(n2) シアノ基;(n3) ニトロ基;(n7) (C1-C6)アルキル基;(n8) (C1-C6)アルコキシ基;(n9) (C3-C6)シクロアルキル基;(n10) (C1-C6)アルキルスルファニル基;(n12) (C1-C6)アルキルスルホニル基;(n13) ハロ(C1-C6)アルキル基;(n14) ハロ(C1-C6)アルコキシ基;(n19) (C1-C6)アルキルカルボニルアミノ基;(n21) (C1-C6)アルキルスルホニルアミノ基;(n33) 隣り合った2個の置換基が一緒になって形成した、ハロゲン原子及び(C1-C6)アルキル基からなる群から選択される1乃至2個の置換基で置換されてもよいメチレンジオキシ基;及び(n34) N‐(C1-C6)アルキルアミノスルホニル基からなる、請求項1に記載の化合物又はその塩類。 R 1 is
(a1) Hydrogen atom; (a3) (C 2 -C 6 ) alkenyl group; (a6) Halo (C 1 -C 6 ) alkyl group; (a10) 1 to 3 each independently selected from substituent group A (a16) a phenyl (C 1 -C 6 ) alkyl group; (a17) a substituted (C 1 -C 6 ) alkyl group having 1 to 5 substituents, each independently selected from substituent group C; Substituted phenyl (C 1 - C 6 ) alkyl group having a substituent on the ring; (a18) Pyridyl (C 1 -C 6 ) alkyl group; (a44) Phenyl group; (a45) Each independently from substituent group D Substituted phenyl group having 1 to 5 selected substituents on the ring; (a46) Pyridyl group; (a47) 1 to 4 substituents independently selected from substituent group D on the ring a substituted pyridyl group; (a50) a pyrazinyl group; (a61) a substituted thiazolyl group having on the ring one or two substituents each independently selected from substituent group D; (a64) a thiadiazolyl group; (a67) Substituted pyrazolyl group having 1 to 3 substituents each independently selected from substituent group D on the ring; (a69) Substituted pyrazolyl group having 1 to 2 substituents each independently selected from substituent group D on the ring or (a72) a benzothiazolyl group,
R 2a is (b1) a hydrogen atom,
R 2b is (c1) a hydrogen atom,
R 3a is
(d1) a hydrogen atom; or (d2) a (C 1 -C 6 ) alkyl group,
R 3b is
(e1) a hydrogen atom; or (e2) a (C 1 -C 6 ) alkyl group,
R 4a is (f1) a hydrogen atom,
R 4b is (g1) a hydrogen atom,
R5 is
(h1) (C 1 -C 6 ) alkyl group; (h11) phenyl group; (h12) substituted phenyl group having 1 to 5 substituents on the ring, each independently selected from substituent group E; h13) Pyridyl group; (h14) Substituted pyridyl group having 1 to 4 substituents on the ring, each independently selected from Substituent Group E; (h15) Pyridazinyl group; (h16) Each from Substituent Group E Substituted pyrimidinyl group having 1 to 3 independently selected substituents on the ring; (h18) Substituted pyrimidinyl group having 1 to 3 substituents on the ring, each independently selected from substituent group E ; (h19) pyrazinyl group; (h25) oxazolyl group; (h28) substituted isoxazolyl group having on the ring one or two substituents each independently selected from substituent group E; (h31) thiazolyl group; ( h42) a substituted tetrazolyl group having one substituent selected from substituent group E on the ring; or (h53) a phenyl (C 1 -C 6 ) alkyl group;
R 6 is (i1) a hydrogen atom,
X is a hydroxyl group,
Y is an oxygen atom or a sulfur atom,
Substituent group A is a (j5) (C 3 -C 6 ) cycloalkyl group,
Substituent group C is
(l1) Halogen atom; (l2) Cyano group; (l9) (C 1 - C 6 ) alkoxy group; (l11) (C 1 - C 6 ) alkylsulfanyl group; (l14) Halo (C 1 - C 6 ) Alkyl group; (l17) halo(C 1 -C 6 )alkoxy group; (l19) halo(C 1 -C 6 )alkylsulfanyl group; and (l20) halo(C 1 -C 6 )alkylsulfinyl group,
The substituent group D is
(m7) (C 1 -C 6 ) alkyl group; (m15) halo (C 1 -C 6 ) alkyl group; (m18) halo (C 1 -C 6 ) alkoxy group; (m20) halo (C 1 -C 6 ) Alkylsulfanyl group; and (m36) 1 to 2 selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group formed by two adjacent substituents together. Consists of a methylenedioxy group which may be substituted with a substituent,
The substituent group E is
(n1) Halogen atom; (n2) Cyano group; (n3) Nitro group; (n7) (C 1 - C 6 ) alkyl group; (n8) (C 1 - C 6 ) alkoxy group; (n9) (C 3 -C 6 ) cycloalkyl group; (n10) (C 1 -C 6 ) alkylsulfanyl group; (n12) (C 1 -C 6 ) alkylsulfonyl group; (n13) halo(C 1 -C 6 ) alkyl group; (n14) Halo(C 1 -C 6 )alkoxy group; (n19) (C 1 -C 6 )alkylcarbonylamino group; (n21) (C 1 -C 6 )alkylsulfonylamino group; (n33) Adjacent A methylenedioxy group optionally substituted with 1 to 2 substituents selected from the group consisting of a halogen atom and a (C 1 -C 6 ) alkyl group, formed by two substituents taken together; and (n34) N-(C 1 -C 6 )alkylaminosulfonyl group or a salt thereof according to claim 1. - 請求項1乃至3の何れか一項に記載の化合物又はその塩類を有効成分として含有することを特徴とする有害生物防除剤。 A pest control agent comprising the compound or salt thereof according to any one of claims 1 to 3 as an active ingredient.
- 請求項1乃至3の何れか一項に記載の化合物又はその塩類を有効成分として含有することを特徴とする農園芸用害虫防除剤。 An agricultural and horticultural pest control agent characterized by containing the compound or its salts according to any one of claims 1 to 3 as an active ingredient.
- 請求項1乃至3の何れか一項に記載の化合物又はその塩類を有効成分として含有することを特徴とする動物用外部寄生虫防除剤。 An animal ectoparasite control agent comprising the compound or salt thereof according to any one of claims 1 to 3 as an active ingredient.
- 請求項1乃至3の何れか一項に記載の化合物又はその塩類を有効成分として含有することを特徴とする動物用内部寄生虫防除剤。 An animal endoparasite control agent characterized by containing the compound or its salt according to any one of claims 1 to 3 as an active ingredient.
- 請求項5に記載の農園芸用害虫防除剤の有効量を植物又は土壌に処理することを特徴とする農園芸用害虫の防除方法。 A method for controlling agricultural and horticultural pests, which comprises applying an effective amount of the agricultural and horticultural pest control agent according to claim 5 to plants or soil.
- 請求項6に記載の動物用外部寄生虫防除剤の有効量を対象動物に、経口又は非経口投与することを特徴とする動物の外部寄生虫の防除方法。 A method for controlling ectoparasites in animals, which comprises orally or parenterally administering an effective amount of the animal ectoparasiticide according to claim 6 to a target animal.
- 請求項7に記載の動物用内部寄生虫防除剤有効量を対象動物に、経口又は非経口投与することを特徴とする動物の内部寄生虫の防除方法。 A method for controlling endoparasites in animals, which comprises orally or parenterally administering an effective amount of the animal endoparasite control agent according to claim 7 to a target animal.
- 請求項1乃至3の何れか一項に記載の化合物又はその塩類の有害生物防除剤としての使用。 Use of the compound or salt thereof according to any one of claims 1 to 3 as a pest control agent.
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