KR102605762B1 - 살균성 조성물 - Google Patents
살균성 조성물 Download PDFInfo
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- KR102605762B1 KR102605762B1 KR1020187025799A KR20187025799A KR102605762B1 KR 102605762 B1 KR102605762 B1 KR 102605762B1 KR 1020187025799 A KR1020187025799 A KR 1020187025799A KR 20187025799 A KR20187025799 A KR 20187025799A KR 102605762 B1 KR102605762 B1 KR 102605762B1
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- KR
- South Korea
- Prior art keywords
- compound
- formula
- plants
- methyl
- pathogens
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- 239000000203 mixture Substances 0.000 title claims abstract description 74
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 170
- 238000000034 method Methods 0.000 claims abstract description 59
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- -1 manzeb Chemical compound 0.000 claims description 217
- 241000196324 Embryophyta Species 0.000 claims description 130
- 230000008569 process Effects 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 238000005507 spraying Methods 0.000 claims description 13
- 241000607479 Yersinia pestis Species 0.000 claims description 9
- 239000004615 ingredient Substances 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 238000010410 dusting Methods 0.000 claims description 8
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 claims description 8
- 239000005747 Chlorothalonil Substances 0.000 claims description 7
- 239000005808 Metalaxyl-M Substances 0.000 claims description 7
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 claims description 7
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- ZQEIXNIJLIKNTD-GFCCVEGCSA-N metalaxyl-M Chemical compound COCC(=O)N([C@H](C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-GFCCVEGCSA-N 0.000 claims description 7
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 claims description 6
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 claims description 6
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 claims description 6
- SOUGWDPPRBKJEX-UHFFFAOYSA-N 3,5-dichloro-N-(1-chloro-3-methyl-2-oxopentan-3-yl)-4-methylbenzamide Chemical compound ClCC(=O)C(C)(CC)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 SOUGWDPPRBKJEX-UHFFFAOYSA-N 0.000 claims description 6
- PCCSBWNGDMYFCW-UHFFFAOYSA-N 5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-1,3-oxazolidine-2,4-dione Chemical compound O=C1C(C)(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)N1NC1=CC=CC=C1 PCCSBWNGDMYFCW-UHFFFAOYSA-N 0.000 claims description 6
- 239000005730 Azoxystrobin Substances 0.000 claims description 6
- 239000005745 Captan Substances 0.000 claims description 6
- 239000005772 Famoxadone Substances 0.000 claims description 6
- 239000005774 Fenamidone Substances 0.000 claims description 6
- 239000005781 Fludioxonil Substances 0.000 claims description 6
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- 239000005867 Iprodione Substances 0.000 claims description 6
- 239000005797 Iprovalicarb Substances 0.000 claims description 6
- NWUWYYSKZYIQAE-ZBFHGGJFSA-N L-(R)-iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-ZBFHGGJFSA-N 0.000 claims description 6
- NQRFDNJEBWAUBL-UHFFFAOYSA-N N-[cyano(2-thienyl)methyl]-4-ethyl-2-(ethylamino)-1,3-thiazole-5-carboxamide Chemical compound S1C(NCC)=NC(CC)=C1C(=O)NC(C#N)C1=CC=CS1 NQRFDNJEBWAUBL-UHFFFAOYSA-N 0.000 claims description 6
- 240000007594 Oryza sativa Species 0.000 claims description 6
- 235000007164 Oryza sativa Nutrition 0.000 claims description 6
- 239000005816 Penthiopyrad Substances 0.000 claims description 6
- 229930182764 Polyoxin Natural products 0.000 claims description 6
- 239000005822 Propiconazole Substances 0.000 claims description 6
- 239000005823 Propineb Substances 0.000 claims description 6
- 239000005831 Quinoxyfen Substances 0.000 claims description 6
- 239000005839 Tebuconazole Substances 0.000 claims description 6
- 239000005857 Trifloxystrobin Substances 0.000 claims description 6
- 239000005860 Valifenalate Substances 0.000 claims description 6
- 239000005863 Zoxamide Substances 0.000 claims description 6
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 claims description 6
- 229940117949 captan Drugs 0.000 claims description 6
- 239000000645 desinfectant Substances 0.000 claims description 6
- LMVPQMGRYSRMIW-KRWDZBQOSA-N fenamidone Chemical compound O=C([C@@](C)(N=C1SC)C=2C=CC=CC=2)N1NC1=CC=CC=C1 LMVPQMGRYSRMIW-KRWDZBQOSA-N 0.000 claims description 6
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 claims description 6
- GBOYJIHYACSLGN-UHFFFAOYSA-N fluopicolide Chemical compound ClC1=CC(C(F)(F)F)=CN=C1CNC(=O)C1=C(Cl)C=CC=C1Cl GBOYJIHYACSLGN-UHFFFAOYSA-N 0.000 claims description 6
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 claims description 6
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 claims description 6
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 claims description 6
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 claims description 6
- CRFYLQMIDWBKRT-LPYMAVHISA-N pyribencarb Chemical compound C1=C(Cl)C(CNC(=O)OC)=CC(C(\C)=N\OCC=2N=C(C)C=CC=2)=C1 CRFYLQMIDWBKRT-LPYMAVHISA-N 0.000 claims description 6
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 claims description 6
- 235000009566 rice Nutrition 0.000 claims description 6
- 239000002689 soil Substances 0.000 claims description 6
- 238000003892 spreading Methods 0.000 claims description 6
- 230000007480 spreading Effects 0.000 claims description 6
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 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 claims description 6
- 239000005821 Propamocarb Substances 0.000 claims description 5
- 239000005842 Thiophanate-methyl Substances 0.000 claims description 5
- 238000007654 immersion Methods 0.000 claims description 5
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 claims description 5
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 claims description 5
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 238000005187 foaming Methods 0.000 claims description 4
- 235000019988 mead Nutrition 0.000 claims description 4
- NGUQQTZEJFXNMY-UHFFFAOYSA-N [3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl] methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=CC=2COC(OCC=21)C=1N=C(SC=1)C1CCN(CC1)C(CN1N=C(C=C1C(F)F)C(F)F)=O NGUQQTZEJFXNMY-UHFFFAOYSA-N 0.000 claims description 3
- ADQPPIFJMUMJDE-UHFFFAOYSA-N [3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazol-4-yl]-6-fluoro-1,5-dihydro-2,4-benzodioxepin-9-yl] methanesulfonate Chemical compound FC1=CC=C(C=2COC(OCC=21)C=1N=C(SC=1)C1CCN(CC1)C(CN1N=C(C=C1C(F)F)C(F)F)=O)OS(=O)(=O)C ADQPPIFJMUMJDE-UHFFFAOYSA-N 0.000 claims description 3
- MKHBUJATPVSVQB-UHFFFAOYSA-N [3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl] methanesulfonate Chemical compound CS(=O)(=O)OC1=CC=CC=2COC(OCC=21)C=1N=C(SC=1)C1CCN(CC1)C(CN1N=C(C=C1C)C(F)(F)F)=O MKHBUJATPVSVQB-UHFFFAOYSA-N 0.000 claims description 3
- UYWFLHVJGRXRHQ-UHFFFAOYSA-N [6-fluoro-3-[2-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]piperidin-4-yl]-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-9-yl] methanesulfonate Chemical compound FC1=CC=C(C=2COC(OCC=21)C=1N=C(SC=1)C1CCN(CC1)C(CN1N=C(C=C1C)C(F)(F)F)=O)OS(=O)(=O)C UYWFLHVJGRXRHQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000003958 fumigation Methods 0.000 claims description 3
- 238000010422 painting Methods 0.000 claims description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 32
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 25
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- 125000005843 halogen group Chemical group 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
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- 239000002585 base Substances 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
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- 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
- 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
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Classifications
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- 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
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- A—HUMAN NECESSITIES
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- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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- A—HUMAN NECESSITIES
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
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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
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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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
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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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
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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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
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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
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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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
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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
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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
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Abstract
식 [1] 로 나타내는 화합물 또는 그 염을 포함하는 살균성 조성물을 시용하는 공정을 포함하는 식물 병원성 미생물에 의해 발생하는 식물 병해를 방제하는 방법에 관한 것이다.
Description
본 발명은, 축합 11 원 고리 화합물, 그 에난티오머, 혹은 그들의 혼합물, 또는 그 농원예상 허용 가능한 염의 적어도 1 종과, 다른 농원예용 살균제 또는 그 염을 적어도 1 종을 함유하는 것을 특징으로 하는 살균성 조성물에 관한 것이다.
지금까지 많은 농원예용 살균제를 알아내 왔지만, 약제 감수성 저하의 문제, 효과의 지속성의 문제, 사용시의 안전성 (예를 들어, 작업자에 대한 안전성) 이나, 환경 영향면에서의 안전성으로부터, 지금 보다 효력이 높고, 안전성이 높은 신규 약제가 요구되고 있다. 또한, 식물 병원균이, 약제에 대한 내성, 저감수성을 획득하는 것을 방해하는 방제 방법이 요구되고 있다.
JANSEN, R. J. et al., Journal of Organic Chemistry, 2001, Vol.66, No.8, pp.2643-2653
AHAD, J. et al., Journal of the Chemical Society, Perkin Transactions 1 : Organic and Bio-organic Chemistry, 1980, No.11, pp.2445-2449
SANTOSO, H. et al., Organic & Biomolecular Chemistry, 2014, Vol.12, No.1, pp.171-176
BHATTACHARJEE, D. et al., Journal of Heterocyclic Chemistry, 1980, Vol.17, No.2, pp.315-320
MEISENHEIMER, P. L. et al., DRUG METABOLISM AND DISPOSITION, 2011, Vol.39, No.12, pp.2403-2410
FRAC 코드표 (2015년), FRAC (Fungicide Resistance Action Committee)
페스티사이드 매뉴얼 (2013년), 브리티시 크롭 프로텍션 카운실
쿠미아이 농약 총람 (2014년), 일본 전국 농업 협동 조합 연합회
SHIBUYA INDEX (제17판), 일본 전국 농촌 교육 협회
유용 작물의 병해 방제에는 많은 농원예용 살균 화합물이 사용되고 있고, 살균 활성 능력을 향상시키기 위해서 농원예용 살균 화합물을 혼합하여 농약 제제를 개발하는 것도 시도되고 있지만, 이들 방제 효과는 충분하다고는 할 수 없다. 본 발명은, 이러한 문제를 해결한 우수한 살균 활성을 갖는 신규의 살균성 조성물을 제공하는 것을 목적으로 한다.
본 발명자들은, 상기의 과제를 해결하기 위해서 예의 검토한 결과, 하기 식 [1] 에 나타내는 어느 종의 축합 11 원 고리 화합물과 다른 농원예용 살균 화합물을 조합하여 사용함으로써, 식물 병해를 효율적으로 방제할 수 있는 것을 알아냈다. 본 발명은 이 지견에 기초하는 것이다.
(1)
(a) 식 [1]
[화학식 1]
{식 중, T 는, CH 또는 질소 원자이고,
R1 은, 수소 원자, C1 ∼ C6 알킬, C2 ∼ C6 알케닐, C1 ∼ C6 할로알킬, C1 ∼ C6 알콕시, 할로겐 원자, 시아노 또는 하이드록시이고,
R2, R3, R4 및 R5 는, 각각 독립적으로 수소 원자, C1 ∼ C6 알킬, C3 ∼ C6 시클로알킬, C1 ∼ C6 할로알킬, C1 ∼ C6 알콕시, C1 ∼ C6 할로알콕시, 할로겐 원자, 시아노 또는 하이드록시이고, 또는 R2 와 R3 및 R4 와 R5 는 각각 독립적으로 그것들이 결합하는 탄소 원자와 하나가 되어 카르보닐기 (C=O) 를 형성하고,
R6 은, 각각 독립적으로 옥소, C1 ∼ C6 알킬, C2 ∼ C6 알케닐, C1 ∼ C6 할로알킬, C1 ∼ C6 알콕시, 할로겐 원자, 시아노 또는 하이드록시이고,
n 은, 0 ∼ 2 이고,
X1, X2, X3 및 X4 는 각각 독립적으로 수소 원자, 할로겐 원자, 시아노, 하이드록시, 니트로, 포르밀, 메르캅토, C1 ∼ C6 알킬, C2 ∼ C6 알케닐, C2 ∼ C6 알키닐, C1 ∼ C6 할로알킬, C2 ∼ C6 할로알케닐, C2 ∼ C6 할로알키닐, C1 ∼ C6 알콕시, C2 ∼ C6 알케닐옥시, C2 ∼ C6 알키닐옥시, C1 ∼ C6 할로알콕시, C2 ∼ C6 할로알케닐옥시, C2 ∼ C6 할로알키닐옥시, 카르복시, 카르바모일, C3 ∼ C6 시클로알킬, C3 ∼ C8 할로시클로알킬, C3 ∼ C6 시클로알콕시, C3 ∼ C8 할로시클로알콕시, C2 ∼ C6 알콕시알킬, C4 ∼ C10 시클로알콕시알킬, C2 ∼ C6 할로알콕시알킬, C4 ∼ C10 할로시클로알콕시알킬, C3 ∼ C8 알콕시알콕시알킬, C2 ∼ C6 알콕시알콕시, C4 ∼ C10 시클로알킬알콕시, C1 ∼ C6 하이드록시알킬, C4 ∼ C10 시클로알킬알킬, C4 ∼ C10 알킬시클로알킬, C6 ∼ C14 시클로알킬시클로알킬, C4 ∼ C10 할로시클로알킬알킬, C6 ∼ C14 할로시클로알킬시클로알킬, C4 ∼ C10 할로알킬시클로알킬, C5 ∼ C10 알킬시클로알킬알킬, C3 ∼ C8 시클로알케닐, C3 ∼ C8 할로시클로알케닐, -SR25, -S(O)R25, -S(O)2R25, -OS(O)2R25, -(C1 ∼ C6 알킬) S(O)2R25, C2 ∼ C6 알킬티오알킬, C2 ∼ C6 알킬술피닐알킬, C2 ∼ C6 알킬술포닐알킬, C2 ∼ C6 알킬카르보닐, C2 ∼ C6 할로알킬카르보닐, C4 ∼ C8 시클로알킬카르보닐, C2 ∼ C6 알콕시카르보닐, C2 ∼ C6 할로알콕시카르보닐, C4 ∼ C8 시클로알콕시카르보닐, C5 ∼ C10 시클로알킬알콕시카르보닐, C2 ∼ C6 알킬카르보닐옥시, C2 ∼ C6 할로알킬카르보닐옥시, C4 ∼ C8 시클로알킬카르보닐옥시, C2 ∼ C6 알콕시카르보닐옥시, C2 ∼ C6 할로알콕시카르보닐옥시, C4 ∼ C8 시클로알콕시카르보닐옥시, C3 ∼ C6 알킬카르보닐알콕시, -NR26R27, C2 ∼ C6 알킬아미노알킬, C3 ∼ C8 (디알킬아미노) 알킬, C2 ∼ C6 할로알킬아미노알킬, C4 ∼ C10 시클로알킬아미노알킬, C1 ∼ C6 알킬술포닐아미노, C1 ∼ C6 할로알킬술포닐아미노, C2 ∼ C6 알킬아미노카르보닐, C3 ∼ C10 (디알킬아미노) 카르보닐, C4 ∼ C8 시클로알킬아미노카르보닐, C2 ∼ C8 (N-알콕시-N-알킬) 아미노, C2 ∼ C8 (디알킬아미노) 옥시, C3 ∼ C10 트리알킬히드라지닐, C3 ∼ C10 트리알킬실릴, C4 ∼ C10 트리알킬실릴알킬, C5 ∼ C10 트리알킬실릴알키닐, C3 ∼ C10 트리알킬실릴옥시, C4 ∼ C12 트리알킬실릴알콕시, C5 ∼ C12 트리알킬실릴알콕시알킬, C5 ∼ C12 트리알킬실릴알키닐옥시, C2 ∼ C6 알킬술포닐옥시알킬, C2 ∼ C6 할로알킬술포닐옥시알킬, -C(=NOR28)R29, -C(=NR30)R29, C2 ∼ C6 시아노알킬, 페닐, 페녹시 또는 벤질이고, 또는 X1 및 X2, X2 및 X3 그리고 X3 및 X4 는, 하나가 되어 산소 원자, 황 원자, -NR31- 을 포함해도 되는 C2 ∼ C6 알킬렌 사슬을 형성하고, 또는 그것들이 결합하는 탄소 원자와 하나가 되어 티오펜 고리, 피리딘 고리, 피롤 고리, 이미다졸 고리, 벤젠 고리, 나프탈렌 고리, 피리미딘 고리, 푸란 고리, 피라진 고리, 피라졸 고리 또는 옥사졸 고리를 형성하고,
R25 는, C1 ∼ C8 알킬, C3 ∼ C8 시클로알킬, C1 ∼ C6 할로알킬, C3 ∼ C8 할로시클로알킬, C1 ∼ C6 알킬아미노, 페닐 또는 벤질이고, 페닐 또는 벤질은 1 이상의 R32 로 치환되어 있어도 되고,
R32 는, 각각 독립적으로 C1 ∼ C6 알킬, C3 ∼ C8 시클로알킬, C1 ∼ C6 할로알킬, C1 ∼ C6 알콕시, C1 ∼ C6 할로알콕시, C3 ∼ C8 시클로알콕시, C3 ∼ C8 할로시클로알킬, C1 ∼ C6 알킬티오, C1 ∼ C6 알킬술피닐, C1 ∼ C6 알킬술포닐, C1 ∼ C6 할로알킬티오, C1 ∼ C6 할로알킬술피닐, C1 ∼ C6 할로알킬술포닐, 할로겐 원자, 시아노 또는 하이드록시이고,
R26 및 R27 은, 각각 독립적으로 수소 원자, C1 ∼ C6 알킬, C3 ∼ C8 시클로알킬, C1 ∼ C6 할로알킬, C3 ∼ C8 할로시클로알킬, C1 ∼ C6 알콕시, C2 ∼ C8 디알킬아미노, C2 ∼ C6 알킬카르보닐, C2 ∼ C6 할로알킬카르보닐, C4 ∼ C8 시클로알킬카르보닐, C2 ∼ C6 알콕시카르보닐, C2 ∼ C6 할로알콕시카르보닐 또는 C3 ∼ C10 (디알킬아미노) 카르보닐이고,
R28 은, 수소 원자, C1 ∼ C6 알킬, C1 ∼ C6 할로알킬 또는 벤질이고,
R29 는, 수소 원자, C1 ∼ C6 알킬, C3 ∼ C8 시클로알킬, C1 ∼ C6 할로알킬, C3 ∼ C8 할로시클로알킬, C4 ∼ C10 시클로알킬알킬, 페닐 또는 벤질이고,
R30 은, C1 ∼ C6 알킬, C3 ∼ C8 시클로알킬, C1 ∼ C6 할로알킬, C3 ∼ C8 할로시클로알킬, 페닐 또는 벤질이고,
R31 은, 수소 원자, C1 ∼ C6 알킬, C2 ∼ C6 알케닐, C2 ∼ C6 알키닐, C1 ∼ C6 할로알킬, C2 ∼ C6 할로알케닐, C2 ∼ C6 할로알키닐, C2 ∼ C6 알콕시알킬, C3 ∼ C6 시클로알킬, C3 ∼ C6 할로시클로알킬, C2 ∼ C6 알킬티오알킬, C2 ∼ C6 알킬술피닐알킬, C2 ∼ C6 알킬술포닐알킬, C2 ∼ C6 알킬카르보닐, C2 ∼ C6 할로알킬카르보닐, C2 ∼ C6 알콕시카르보닐, C3 ∼ C6 알콕시카르보닐알킬, C2 ∼ C6 알킬아미노카르보닐, C3 ∼ C6 (디알킬아미노) 카르보닐, C1 ∼ C6 알킬술포닐 또는 C1 ∼ C6 할로알킬술포닐이고,
R7 및 R8 은, 각각 독립적으로 C1 ∼ C4 알킬, 할로겐 원자, C3 ∼ C6 시클로알킬 또는 C1 ∼ C4 할로알킬이고,
R9 및 R10 은, 각각 독립적으로 수소 원자, 할로겐 원자, 시아노, 하이드록시, C1 ∼ C6 알킬, C2 ∼ C6 알케닐, C2 ∼ C6 알키닐, C1 ∼ C6 할로알킬, C2 ∼ C6 할로알케닐, C2 ∼ C6 할로알키닐, C1 ∼ C6 알콕시, C1 ∼ C6 할로알콕시, C3 ∼ C6 시클로알킬, C1 ∼ C6 알킬티오, C1 ∼ C6 알킬술피닐, C1 ∼ C6 알킬술포닐, C1 ∼ C6 할로알킬티오, C1 ∼ C6 할로알킬술피닐 또는 C1 ∼ C6 할로알킬술포닐이고,
G1 은, 산소 원자 또는 황 원자이다}
로 나타내는 화합물, 그 에난티오머, 혹은 그들의 혼합물, 또는 그 농원예상 허용 가능한 염의 적어도 1 종과, (b) 농원예용 살균제 또는 그 염을 적어도 1 종을 포함하는 살균성 조성물.
(2)
식 [1] 의 화합물이
R1, R2, R3, R4 및 R5 는, 수소 원자이고,
n 은, 0 이고,
X1, X2, X3 및 X4 가 각각 독립적으로 수소 원자, 할로겐 원자, 시아노, 하이드록시, 니트로, 포르밀, C1 ∼ C4 알킬, C1 ∼ C4 할로알킬, C1 ∼ C4 하이드록시알킬, C1 ∼ C4 알콕시, C1 ∼ C4 할로알콕시, -SR25, -S(O)2R25, -OS(O)2R25, C2 ∼ C4 알킬카르보닐옥시, C2 ∼ C4 알콕시카르보닐옥시, 또는 -C(=NOR28)R29 이고,
R25 는 C1 ∼ C4 알킬, 시클로프로필 또는 C1 ∼ C4 할로알킬이고,
R28 및 R29 는, 각각 독립적으로 수소 원자 또는 메틸이고,
R7 및 R8 은, 각각 독립적으로 C1 ∼ C4 알킬, 할로겐 원자 또는 C1 ∼ C4 할로알킬이고,
R9 및 R10 은 수소 원자이고,
G1 은 산소 원자인
(1) 에 기재된 살균성 조성물.
(3)
식 [1] 의 화합물이
X1 은 -OS(O)2R25 이고,
X2 및 X3 은 수소 원자이고,
X4 는 수소 원자, 니트로, 불소 원자, 염소 원자, 브롬 원자, 메틸, 메톡시, 디플루오로메톡시, 트리플루오로메톡시 또는 -OS(O)2R25 이고,
R25 는 메틸이고,
R7 은, 트리플루오로메틸, 디플루오로메틸 또는 염소 원자이고,
R8 은, 각각 독립적으로 메틸, 트리플루오로메틸, 디플루오로메틸 또는 염소 원자인
(1) 또는 (2) 에 기재된 살균성 조성물.
(4)
식 [1] 의 화합물이
4-[4-(6-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘,
4-[4-(6-플루오로-9-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘,
4-[4-(6-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘, 및
4-[4-(6-플루오로-9-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘
혹은 이들의 혼합물에서 선택되는
(1) ∼ (3) 의 어느 하나에 기재된 살균성 조성물.
(5)
성분 (b) 가, 벤티아발리카르브, 발리페날레이트, 족사미드, 파목사돈, 이프로발리카르브, 페나미돈, 플루오피콜리드, 아메톡트라딘, 시아조파미드, 만디프로파미드, 메탈락실-M, 에타복삼, 디메토모르프, 시목사닐, 염기성 황산동, 클로로타로닐, 만제브, 프로피네브, 캡탄, 크레속심-메틸, 아족시스트로빈, 트리플록시스트로빈, 플루아지남, 피리벤카르브, 펜티오피라드, 퀴녹시펜, 피리오페논, 프로파모카르브, 포세틸-알루미늄, 이미녹타딘, 플루디옥소닐, 티오파네이트-메틸, 이프로디온, 테부코나졸, 시프로디닐, 아미술브롬, 트리시클라졸, 폴리옥신, 테부플로퀸, 프로피코나졸, 옥사티아피프롤린 또는 이들의 염에서 선택되는 적어도 1 종의 화합물을 포함하는, (1) ∼ (4) 의 어느 하나에 기재된 살균성 조성물.
(6)
농원예용 살균제로서 사용하는, (1) ∼ (5) 의 어느 하나에 기재된 살균성 조성물.
(7)
(a) (1) 에 기재된 식 [1] 로 나타내는 화합물, 및 (b) 농원예용 살균제 또는 그 염을, 식물 또는 식물 주변의 영역에 처리하는 공정을 포함하고, 성분 (a) 및 성분 (b) 가 동시에, 연속해서, 또는 따로따로 처리되는, 식물 유해 생물의 방제 방법.
(8)
상기 처리가, 분무, 산포, 살분, 스프레이, 확산, 침지, 관주, 주입, 살수 (침수), 발포, 도포, 분의, 코팅, 분사, 훈증, 훈연, 연무 및 도장으로 이루어지는 군에서 선택되는 적어도 1 개인, (7) 에 기재된 식물 유해 생물의 방제 방법.
(9)
상기 식물 주변의 영역이, 토양, 논, 수경 재배의 물, 및 재배 자재로 이루어지는 군에서 선택되는 적어도 1 개인, (7) 또는 (8) 에 기재된 식물 유해 생물의 방제 방법.
(10)
식 [1] 의 화합물이
4-[4-(6-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘,
4-[4-(6-플루오로-9-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘,
4-[4-(6-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘, 및
4-[4-(6-플루오로-9-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘,
혹은 이들의 혼합물에서 선택되는
(7) ∼ (9) 의 어느 하나에 기재된 식물 유해 생물의 방제 방법.
(11)
성분 (b) 가, 벤티아발리카르브, 발리페날레이트, 족사미드, 파목사돈, 이프로발리카르브, 페나미돈, 플루오피콜리드, 아메톡트라딘, 시아조파미드, 만디프로파미드, 메탈락실-M, 에타복삼, 디메토모르프, 시목사닐, 염기성 황산동, 클로로타로닐, 만제브, 프로피네브, 캡탄, 크레속심-메틸, 아족시스트로빈, 트리플록시스트로빈, 플루아지남, 피리벤카르브, 펜티오피라드, 퀴녹시펜, 피리오페논, 프로파모카르브, 포세틸-알루미늄, 이미녹타딘, 플루디옥소닐, 티오파네이트-메틸, 이프로디온, 테부코나졸, 시프로디닐, 아미술브롬, 트리시클라졸, 폴리옥신, 테부플로퀸, 프로피코나졸, 옥사티아피프롤린 또는 이들의 염에서 선택되는 적어도 1 종의 화합물을 포함하는,
(7) ∼ (10) 의 어느 하나에 기재된 식물 유해 생물의 방제 방법.
식 [1] 로 나타내는 축합 11 원 고리 화합물 자체도 유해 생물, 즉, 농원예용 식물에 대한 병원균에 대하여 우수한 방제 효과를 나타내지만, 본 발명인 살균성 조성물로서 사용한 경우가 우수한 상승 효과를 발휘한다.
이하, 본 발명에 대하여 상세하게 설명한다.
본 발명에 있어서의 상기 축합 11 원 고리 화합물에는, 식 [1] 로 나타내는 축합 11 원 고리 화합물 외에, 당해 화합물의 염, 및 식 [1] 로 나타내는 축합 11 원 고리 화합물의 N-옥사이드도 포함된다. 여기서 염으로는 특별히 한정되지 않고, 예를 들어, 농약 제조상 허용되는 염을 들 수 있고, 구체적으로는, 나트륨염, 칼륨염, 마그네슘염, 칼슘염, 알루미늄염 등을 들 수 있다. 또한 본 발명 화합물에 존재하는 모든 가능한 입체 이성체 혹은 광학 이성체도, 식 [1] 로 나타내는 축합 11 원 고리 화합물의 범위에 포함된다.
본 발명의 축합 11 원 고리 화합물은, 비정성 물질 또는 결정의 형태로 사용되어도 되고, 수화물, 용매화물을 형성한 고체, 또는 용액, 현탁액의 형태로 사용할 수도 있다. 본 발명의 축합 11 원 고리 화합물은, 다른 성분과의 혼합물로서 사용해도 되는 것 외에, 식 [1] 의 화합물의 혼합물, 특히 라세미체 등의 에난티오머의 혼합물이나 디아스테레오머의 혼합물로서 사용하는 것도 포함된다.
식 [1] 은, 본 발명에 의해 사용할 수 있는 축합 11 원 고리 화합물의 일반적인 정의를 부여하고 있다. 상기 및 하기에 있어서 나타내는 식에 관한 기의 바람직한 정의에 대하여, 이하에 기재한다. 그러한 정의는, 식 [1] 로 나타내는 최종 생성물에 적용되고, 및, 동일하게, 모든 중간체에도 적용된다.
이하에 바람직한 형태를 기재한다.
T 는, 바람직하게는 CH 이다.
R1 은, 바람직하게는 수소 원자이다.
R2, R3, R4 및 R5 는, 바람직하게는 수소 원자 또는 메틸이고, 더욱 바람직하게는 수소 원자이다.
n 은, 바람직하게는 0 이다 (즉, R6 은, 바람직하게는 존재하지 않는다).
X1, X2, X3 및 X4 는 각각 독립적으로, 바람직하게는, 수소 원자, 할로겐 원자, 시아노, 하이드록시, 니트로, 포르밀, C1 ∼ C4 알킬, C1 ∼ C4 할로알킬, C1 ∼ C4 하이드록시알킬, C1 ∼ C4 알콕시, C1 ∼ C4 할로알콕시, -SR25, -S(O)2R25, -OS(O)2R25, C2 ∼ C4 알킬카르보닐옥시, C2 ∼ C4 알콕시카르보닐옥시, 또는 -C(=NOR28)R29 이고, 더욱 바람직하게는, X1, X2, X3 및 X4 중 적어도 1 개는 -OS(=O)2R25 이고, 특히 바람직하게는, X1 은, -OS(O)2R25 이고, 특히 바람직하게는, X2 및 X3 은, 수소 원자이고, 특히 바람직하게는, X4 는, 수소 원자, 니트로, 불소 원자, 브롬 원자, 메틸, 메톡시, 디플루오로메톡시, 트리플루오로메톡시 또는 -OS(O)2R25 이고, 가장 바람직하게는, X4 는, 수소 원자, 니트로, 메틸, 불소 원자 또는 메톡시이다.
R25 는, 바람직하게는, C1 ∼ C4 알킬, 시클로프로필 또는 C1 ∼ C4 할로알킬이고, 더욱 바람직하게는, 메틸이다.
R28 은, 바람직하게는, 수소 원자 또는 C1 ∼ C4 알킬이고, 더욱 바람직하게는, 수소 원자 또는 메틸이다.
R29 는, 바람직하게는, 수소 원자 또는 C1 ∼ C4 알킬이고, 더욱 바람직하게는, 수소 원자 또는 메틸이다.
R7, R8 은 각각 독립적으로, 바람직하게는, C1 ∼ C4 알킬, 할로겐 원자 또는 C1 ∼ C4 할로알킬이고, 더욱 바람직하게는, 메틸, 디플루오로메틸, 트리플루오로메틸 또는 염소 원자이다.
R9 및 R10 은, 바람직하게는 수소 원자이다.
G1 은, 바람직하게는 산소 원자이다.
일반적인 범위 또는 바람직한 범위에 있어서, 상기에서 나타내고 있는 기의 정의 및 설명은, 필요에 따라 서로 조합하는 것도 가능하다. 즉, 각각의 범위와 바람직한 범위의 사이에서 조합하는 것도 가능하다. 그것들은, 최종 생성물과 그에 대응하는 전구체 및 중간체의 양방에 적용된다.
바람직한 1 개의 양태는, 식 [1] {식 중, R7 은 트리플루오로메틸이고, R8 은 메틸을 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, R7 및 R8 은 트리플루오로메틸을 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, R7 및 R8 은 디플루오로메틸을 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, R7 및 R8 은 메틸을 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, R7 및 R8 은 염소 원자를 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, X1, X2, X3 및 X4 중 적어도 1 개는 메틸술포닐옥시를 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, X1 은 메틸술포닐옥시이고, X2, X3 및 X4 는 수소 원자를 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, X1 은 메틸술포닐옥시이고, X2 및 X3 은 수소 원자이고, X4 는 불소 원자를 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, X1 은 메틸술포닐옥시이고, X2 및 X3 은 수소 원자이고, X4 는 염소 원자를 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, X1 은 메틸술포닐옥시이고, X2 및 X3 은 수소 원자이고, X4 는 브롬 원자를 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, X1 은 메틸술포닐옥시이고, X2 및 X3 은 수소 원자이고, X4 는 메톡시를 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, X1 은 메틸술포닐옥시이고, X2 및 X3 은 수소 원자이고, X4 는 시아노를 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, X1 은 메틸술포닐옥시이고, X2 및 X3 은 수소 원자이고, X4 는 니트로를 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, X1 은 메틸술포닐옥시이고, X2 및 X3 은 수소 원자이고, X4 는 트리플루오로메톡시를 나타낸다} 로 나타내는 화합물이다.
바람직한 다른 양태는, 추가로 또한, 식 [1] {식 중, X1 및 X4 는 메틸술포닐옥시이고, X2 및 X3 은 수소 원자를 나타낸다} 로 나타내는 화합물이다.
본 명세서에 기재된 용어에 대하여 설명한다.
할로겐 원자란 불소 원자, 염소 원자, 브롬 원자 또는 요오드 원자를 포함 한다.
C1 ∼ C6 과 같은 원소 기호와 아래 첨자의 숫자에 의한 표기는, 이것에 이어서 표기되어 있는 기의 원소수가 아래 첨자의 숫자로 나타내는 범위인 것을 나타내고 있다. 예를 들어, 이 경우에서는 탄소수가 1 ∼ 6 인 것을 나타내고 있고, C2 ∼ C6 의 표기에서는 탄소수가 2 ∼ 6 인 것을 나타내고 있다.
C1 ∼ C6 과 같은 원소 기호와 아래 첨자의 숫자에 의한 표기에 이어서 복합 치환기가 표기되어 있는 경우, 복합 치환기 전체의 원소수가 아래 첨자의 숫자로 나타내는 범위인 것을 나타내고 있다. 예를 들어, C4 ∼ C8 시클로알킬카르보닐옥시에 있어서는, 시클로알킬카르보닐옥시 전체의 탄소수가 4 ∼ 8 인 것을 나타내고 있고, 시클로프로필카르보닐기 등을 포함한다. 또한, 예를 들어, C2 ∼ C8 시아노알킬에 있어서는, 시아노알킬 전체의 탄소수가 2 ∼ 8 인 것을 나타내고 있다. C2 ∼ C8 시아노알킬에 있어서는, 1 또는 복수의 시아노기를 포함하고 있어도 되고, 시아노메틸기 등을 포함한다.
알킬이란, 예를 들어, 탄소수가 1 ∼ 8, 바람직하게는 탄소수가 1 ∼ 6 인 직사슬 또는 분기 사슬형의 알킬을 의미하고, 예를 들어 메틸, 에틸, n-프로필, 이소부틸, n-부틸, sec-부틸, 이소부틸, tert-부틸, n-펜틸, 1-메틸부틸, 2-메틸부틸, 3-메틸부틸, 1-에틸프로필, 1,1-디메틸프로필, 1,2-디메틸프로필, 네오펜틸, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 3-메틸펜틸, 4-메틸펜틸, 1-에틸부틸, 2-에틸부틸, 1,1-디메틸부틸, 1,2-디메틸부틸, 1,3-디메틸부틸, 2,2-디메틸부틸, 2,3-디메틸부틸, 3,3-디메틸부틸, 1,1,2-트리메틸프로필, 1,2,2-트리메틸프로필, 1-에틸-1-메틸프로필, 1-에틸-2-메틸프로필 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로알킬, 알킬티오, 알킬카르보닐, 알킬술포닐옥시 등의 복합 치환기의 일부로서의 알킬에도 적용된다. 예를 들어 알킬시클로알킬과 같이, 알킬을 말단에 포함하는 복합 치환기의 경우, 시클로알킬의 그 부분은, 동일하거나 혹은 상이한 알킬에 의해 독립적으로 모노 치환 또는 다치환되어 있어도 된다. 다른 기, 예를 들어 알케닐, 알콕시, 하이드록시, 할로겐 원자 등이 말단에 있는 복합 치환기도 동일하게 해석된다.
시클로알킬이란, 예를 들어, 탄소수가 3 ∼ 8, 바람직하게는 탄소수가 3 ∼ 6 인 분기 사슬을 갖는 시클로알킬을 의미하고, 예를 들어 시클로프로필, 1-메틸시클로프로필, 2-메틸시클로프로필, 시클로부틸, 시클로펜틸, 시클로헥실, 4,4-디메틸시클로헥실 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로시클로알킬 등의 복합 치환기의 일부로서의 시클로알킬에도 적용된다.
시클로알케닐이란, 예를 들어, 탄소수가 3 ∼ 8, 바람직하게는 탄소수가 3 ∼ 6 인 분기 사슬을 갖는 시클로알케닐을 의미하고, 예를 들어 시클로프로페닐, 1-메틸시클로프로페닐, 시클로부테닐, 시클로펜테닐, 시클로헥세닐 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로시클로알케닐 등의 복합 치환기의 일부로서의 시클로알케닐에도 적용된다.
시클로알콕시란, 예를 들어, 탄소수가 3 ∼ 8, 바람직하게는 탄소수가 3 ∼ 6 인 분기 사슬을 갖는 시클로알콕시를 의미하고, 예를 들어 시클로프로필옥시, 1-메틸시클로프로필옥시, 시클로부틸옥시, 시클로펜틸옥시, 시클로헥실옥시 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로시클로알콕시 등의 복합 치환기의 일부로서의 시클로알콕시에도 적용된다.
「할로···」 (예를 들어, 「할로알킬」) 에 있어서의 「할로」 라는 용어는, 불소, 염소, 브롬 및 요오드를 포함한다. 「할로」 라는 접두어로 나타내는 할로 치환은, 모노 치환 또는 다치환을 포함하고, 바람직하게는 모노 치환, 디 치환 및 트리 치환을 포함한다.
할로알킬이란, 예를 들어, 탄소수가 1 ∼ 6 인 직사슬 또는 분기 사슬형의 알킬로서, 그들 기에 있어서의 수소 원자의 일부 또는 모두가 할로겐 원자에 의해 치환된 기를 의미하고, 예를 들어 플루오로메틸, 클로로메틸, 브로모메틸, 요오드메틸, 디플루오로메틸, 디클로로메틸, 디브로모메틸, 디요오드메틸, 트리플루오로메틸, 트리클로로메틸, 트리브로모메틸, 트리요오드메틸, 1-클로로에틸, 1-브로모에틸, 2-트리플루오로에틸, 3-클로로프로필, 3-브로모프로필, 4-클로로부틸, 4-브로모부틸, 4-트리플루오로부틸, 5-클로로펜틸, 6-클로로헥실 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로알킬카르보닐 등의 복합 치환기의 일부로서의 할로알킬에도 적용된다.
알케닐이란, 예를 들어, 탄소수가 2 ∼ 6 인 직사슬 또는 분기 사슬형의 알케닐을 의미하고, 예를 들어 비닐, 1-프로페닐, 2-프로페닐, 이소프로페닐, 3-부테닐, 1,3-부타디에닐, 4-펜테닐, 5-헥세닐 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로알케닐 등의 복합 치환기의 일부로서의 알케닐에도 적용된다.
알키닐이란, 예를 들어, 탄소수가 2 ∼ 6 인 직사슬 또는 분기 사슬형의 알키닐을 의미하고, 예를 들어 에티닐, 1-프로피닐, 2-프로피닐, 3-부티닐, 1-메틸-3-프로피닐, 4-펜티닐, 5-헥시닐 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로알키닐 등의 복합 치환기의 일부로서의 알키닐에도 적용된다.
알콕시란, 예를 들어, 탄소수가 1 ∼ 6 인 직사슬 또는 분기 사슬형의 알콕시를 의미하고, 예를 들어 메톡시, 에톡시, 프로폭시, 이소프로폭시, 부톡시, 이소부톡시, sec-부톡시, tert-부톡시, 펜틸옥시, 헥실옥시 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로알콕시, 알콕시카르보닐 등의 복합 치환기의 일부로서의 알콕시에도 적용된다.
할로알콕시란, 예를 들어, 1 개 이상, 바람직하게는 1 ∼ 10 개의 할로겐 원자에 의해 치환된 탄소수가 1 ∼ 6 인 직사슬 또는 분기 사슬형의 알콕시를 의미하고, 예를 들어 플루오로메톡시, 클로로메톡시, 브로모메톡시, 요오드메톡시, 디플루오로메톡시, 디클로로메톡시, 디브로모메톡시, 디요오드메톡시, 트리플루오로메톡시, 트리클로로메톡시, 트리브로모메톡시, 트리요오드메톡시, 1-클로로에톡시, 1-브로모에톡시, 2-트리플루오로에톡시, 3-클로로프로폭시, 3-브로모프로폭시, 4-클로로부톡시, 4-브로모부톡시, 4-트리플루오로부톡시, 5-클로로펜톡시, 6-클로로헥실옥시 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로알콕시카르보닐 등의 복합 치환기의 일부로서의 할로알콕시에도 적용된다.
알킬티오란, 예를 들어, 알킬 부분이 상기의 의미인 탄소수가 1 ∼ 6 인 (알킬)-S- 기를 의미하고, 예를 들어 메틸티오, 에틸티오, n-프로필티오, 이소프로필티오 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로알킬티오 등의 복합 치환기의 일부로서의 알킬티오에도 적용된다.
알킬술피닐이란, 예를 들어, 알킬 부분이 상기의 의미인 탄소수가 1 ∼ 6 인 (알킬)-SO- 기를 의미하고, 예를 들어 메틸술피닐, 에틸술피닐, n-프로필술피닐, 이소프로필술피닐 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로알킬술피닐 등의 복합 치환기의 일부로서의 알킬술피닐에도 적용된다.
알킬술포닐이란, 예를 들어, 알킬 부분이 상기의 의미인 탄소수가 1 ∼ 6 인 (알킬)-SO2- 기를 의미하고, 예를 들어 메틸술포닐, 에틸술포닐, n-프로필술포닐, 이소프로필술포닐 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로알킬술포닐 등의 복합 치환기의 일부로서의 알킬술포닐에도 적용된다.
하이드록시알킬이란, 1 ∼ 5 개의 히드록시기에 의해 치환된 탄소 원자수 1 ∼ 6 의 직사슬형 또는 분기형의 알킬기를 의미하고, 예를 들어, 하이드록시메틸, 하이드록시에틸, 하이드록시프로필 또는 하이드록시이소프로필 등을 들 수 있다.
알킬술포닐옥시란, 예를 들어, 알킬 부분이 상기의 의미인 탄소수가 1 ∼ 6 인 (알킬)-S(O)2O- 기를 의미하고, 예를 들어 메틸술포닐옥시, 에틸술포닐옥시, n-프로필술포닐옥시, 이소프로필술포닐옥시 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로알킬술포닐옥시 등의 복합 치환기의 일부로서의 알킬술포닐옥시에도 적용된다.
알킬카르보닐이란, 예를 들어, 알킬 부분이 상기의 의미인 (알킬)-C(=O)- 기를 의미하고, 예를 들어 포르밀, 아세틸, 프로피오닐, 부티릴, 피발로일 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로알킬카르보닐 등의 복합 치환기의 일부로서의 알킬카르보닐에도 적용된다.
알킬카르보닐옥시란, 예를 들어, 알킬 부분이 상기의 의미인 (알킬)-C(=O) O- 기를 의미하고, 예를 들어 메틸카르보닐옥시, 에틸카르보닐옥시, 프로필카르보닐옥시 등의 기를 들 수 있다. 이 정의는, 특별한 정의가 없는 한, 예를 들어 할로알킬카르보닐옥시 등의 복합 치환기의 일부로서의 알킬카르보닐옥시에도 적용된다.
본 발명에 관련된 반응에서 사용하는 산이란, 특별히 언급이 없으면, 반응계 중에서 프로톤을 방출하는 브뢴스테드산을 의미하고, 염산, 브롬화수소산, 황산 등의 무기산, 아세트산, 트리플루오로아세트산, p-톨루엔술폰산, 트리플루오로메탄술폰산 등의 유기산이 예시된다. 본 발명에 관련된 반응에서 사용하는 루이스산은, 수소 이온 이외에서 반응계 중에서 전자쌍 수용체로서 기능하는 화합물을 의미하고, 예를 들어 염화아연, 염화알루미늄, 염화주석, 삼염화붕소, 삼불화붕소, 트리플루오로메탄술폰산트리메틸실릴 등이 예시된다.
본 발명에 관련된 반응에서 사용하는 염기란, 특별히 언급이 없으면, 반응계 중에서 프로톤을 수취하는 화합물, 또는 반응계 중에서 전자쌍 공여체로서 기능하는 화합물을 의미하고, 트리에틸아민, 피리딘, 4-디메틸아미노피리딘, N,N-디메틸아닐린, 1,8-디아자비시클로[5,4,0]-7-운데센 등의 유기 아민류 ; 탄산나트륨, 탄산칼륨, 탄산마그네슘, 탄산칼슘 등의 금속 탄산염류 ; 탄산수소나트륨, 탄산수소 칼륨 등의 금속 탄산수소염류 ; 아세트산나트륨, 아세트산칼륨, 아세트산칼슘, 아세트산마그네슘 등의 금속 아세트산염류로 대표되는 카르복실산 금속염류 ; 나트륨메톡시드, 나트륨에톡시드, 나트륨 tert-부톡시드, 칼륨메톡시드, 칼륨 tert-부톡시드 등의 금속 알콕시드 ; 수산화나트륨, 수산화칼륨, 수산화칼슘, 수산화마그네슘 등의 금속 수산화물 ; 수소화리튬, 수소화나트륨, 수소화칼슘 등의 금속 수소화물 등이 예시된다.
본 명세서에 있어서의 표 중의 다음의 표기는 하기와 같이 각각 해당하는 기를 나타낸다.
예를 들어,
Me : 메틸기,
Et : 에틸기,
n-Pr : n-프로필기,
i-Pr : 이소프로필기,
c-Pr : 시클로프로필기,
n-Bu : n-부틸기,
i-Bu : 이소부틸기,
t-Bu : tert-부틸기,
n-Hex : n-헥실기,
Ph : 페닐기,
Bn : 벤질기.
식 [1] 로 나타내는 본 발명 화합물의 대표적인 제조 방법을 이하에 예시하지만, 이들 방법에 한정되는 것은 아니다.
<제조 방법 1>
식 [1] 로 나타내는 본 발명 화합물은 하기에 예시하는 반응식으로 이루어지는 방법에 의해 제조할 수 있다.
[화학식 2]
(식 중, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, G1, X1, X2, X3, X4, T 및 n 은 각각 [1] 에 정의한 바와 같다.)
식 [2] 로 나타내는 화합물과 식 [3] 으로 나타내는 화합물을, 용매 중, 산 또는 루이스산의 존재하, 바람직하게는 산의 존재하에서 반응시킴으로써, 식 [1] 로 나타내는 본 발명 화합물을 제조할 수 있다.
여기서 사용하는 식 [3] 의 화합물의 사용량은, 식 [2] 의 화합물 1 몰에 대하여 1.0 ∼ 10 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 1.0 ∼ 3.0 몰이다.
본 공정에서 사용할 수 있는 산으로는, 예를 들어 염산, 브롬화수소산, 황산 등의 무기산, 아세트산, 트리플루오로아세트산, p-톨루엔술폰산, 트리플루오로메탄술폰산 등의 유기산 등을 들 수 있다.
본 공정에서 사용할 수 있는 루이스산으로는, 예를 들어 염화아연, 염화알루미늄, 염화주석, 삼염화붕소, 삼불화붕소, 트리플루오로메탄술폰산트리메틸실릴 등을 들 수 있다.
산 또는 루이스산의 사용량은 식 [2] 의 화합물 1 몰에 대하여 0.01 ∼ 5 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 0.1 ∼ 1.0 몰이다.
본 공정에서 사용할 수 있는 용매로는, 본 반응의 진행을 저해하지 않는 것이면 되고, 예를 들어 아세토니트릴 등의 니트릴류 ; 디에틸에테르, 디이소프로필에테르, 테트라하이드로푸란, 디옥산, 모노 글라임, 디글라임 등의 에테르류 ; 디클로로메탄, 디클로로에탄, 클로로포름, 사염화탄소, 테트라클로로에탄 등의 할로겐화탄화수소류 ; 벤젠, 클로로벤젠, 니트로벤젠, 톨루엔 등의 방향족 탄화수소류 ; N,N-디메틸포름아미드, N,N-디메틸아세트아미드 등의 아미드류 ; 1,3-디메틸-2-이미다졸리논 등의 이미다졸리논류 ; 디메틸술폭시드 등의 황 화합물류 등을 사용할 수 있고, 또한 이들의 혼합 용매도 사용할 수 있다.
용매의 사용량은 식 [2] 의 화합물 1 몰에 대하여 0.01 ∼ 100 ℓ 의 범위에서 적절히 선택하면 되고, 바람직하게는 0.1 ∼ 10 ℓ 이다.
반응 온도는 -20 ℃ 내지 사용하는 불활성 용매의 비점역의 범위에서 선택하면 되고, 바람직하게는 0 ℃ ∼ 150 ℃ 의 범위에서 실시하는 것이 바람직하다.
반응 시간은 반응 온도, 반응 기질, 반응량 등에 따라 상이하지만, 통상적으로 10 분 ∼ 48 시간이다.
반응의 목적물인 식 [1] 의 화합물은, 반응 종료 후, 정법에 의해 반응계로부터 채취되고, 필요에 따라 칼럼 크로마토그래피, 재결정 등의 조작에 의해 정제할 수도 있다.
<제조 방법 2>
또한, 식 [1] 로 나타내는 본 발명 화합물은 하기에 예시하는 반응식으로 이루어지는 방법에 의해서도 제조할 수 있다.
[화학식 3]
(식 중, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, G1, X1, X2, X3, X4, T 및 n 은 각각 (1) 에 정의한 바와 같고, L1 은 염소 원자, 브롬 원자 등의 할로겐 원자를 나타낸다.)
(공정 1)
식 [1] 의 화합물은, 식 [4] 의 화합물과 식 [5] 의 화합물을, 염기의 존재하/비존재하, 탈수 축합제 존재하, 용매 중에서 반응시키는 것에 의해서도 제조할 수 있다.
본 공정에서 사용하는 식 [5] 의 화합물의 사용량은, 식 [4] 의 화합물 1 몰에 대하여 0.5 ∼ 10 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 1.0 ∼ 1.2 몰이다.
본 공정에서 사용할 수 있는 탈수 축합제로는, 디시클로헥실카르보디이미드 (DCC), N-(3-디메틸아미노프로필)-N'-에틸카르보디이미드 (EDC 또는 WSC), N,N-카르보닐디이미다졸, 2-클로로-1,3-디메틸이미다졸륨클로라이드, 요오드화-2-클로로-1-피리디늄 등을 사용할 수 있다.
본 반응에서 사용하는 탈수 축합제의 사용량은 식 [4] 의 화합물 1 몰에 대하여 1.0 ∼ 10 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 1.0 ∼ 3.0 몰이다.
본 공정에서 사용할 수 있는 염기로는, 예를 들어 트리에틸아민, 피리딘, 4-디메틸아미노피리딘, N,N-디메틸아닐린, 1,8-디아자비시클로[5,4,0]-7-운데센 등의 유기 아민류 ; 탄산나트륨, 탄산칼륨, 탄산마그네슘, 탄산칼슘 등의 금속 탄산염류 ; 탄산수소나트륨, 탄산수소칼륨 등의 금속 탄산수소염류 ; 아세트산나트륨, 아세트산칼륨, 아세트산칼슘, 아세트산마그네슘 등의 금속 아세트산염류로 대표되는 카르복실산 금속염류 ; 나트륨메톡시드, 나트륨에톡시드, 나트륨 tert-부톡시드, 칼륨메톡시드, 칼륨 tert-부톡시드 등의 금속 알콕시드 ; 수산화나트륨, 수산화칼륨, 수산화칼슘, 수산화마그네슘 등의 금속 수산화물 ; 수소화리튬, 수소화나트륨, 수소화칼슘 등의 금속 수소화물 등을 들 수 있다.
본 반응에서 사용하는 염기의 사용량은 식 [4] 의 화합물 1 몰에 대하여 0 ∼ 100 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 0 ∼ 10 몰이다.
본 공정에서 사용할 수 있는 용매로는, 제조 방법 1 에서 설명한 것과 동일한 것을 들 수 있다.
또한, 용매의 사용량은 식 [4] 의 화합물 1 몰에 대하여 0.01 ∼ 100 ℓ 의 범위에서 적절히 선택하면 되고, 바람직하게는 0.1 ∼ 10 ℓ 이다.
반응 온도는 -20 ℃ 내지 사용하는 불활성 용매의 비점역의 범위에서 선택하면 되고, 바람직하게는 0 ℃ ∼ 100 ℃ 의 범위에서 실시하는 것이 바람직하다.
반응 시간은 반응 온도, 반응 기질, 반응량 등에 따라 상이하지만, 통상적으로 10 분 ∼ 48 시간이다.
(공정 2)
식 [1] 의 화합물은, 식 [4] 의 화합물과 식 [6] 의 화합물을, 염기의 존재하, 용매 중에서 반응시키는 것에 의해서도 제조할 수 있다.
본 공정에서 사용하는 식 [6] 의 화합물의 사용량은, 식 [4] 의 화합물 1 몰에 대하여 0.5 ∼ 10 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 1.0 ∼ 1.2 몰이다.
본 공정에서 사용할 수 있는 염기로는, 공정 1 에서 설명한 것과 동일한 것을 들 수 있다.
본 반응에서 사용하는 염기의 사용량은 식 [4] 의 화합물 1 몰에 대하여 0 ∼ 100 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 0 ∼ 10 몰이다.
본 공정에서 사용할 수 있는 용매로는, 제조 방법 1 에서 설명한 것과 동일한 것을 들 수 있다.
또한, 용매의 사용량은 식 [4] 의 화합물 1 몰에 대하여 0.01 ∼ 100 ℓ 의 범위에서 적절히 선택하면 되고, 바람직하게는 0.1 ∼ 10 ℓ 이다.
반응 온도는 -20 ℃ 내지 사용하는 불활성 용매의 비점역의 범위에서 선택하면 되고, 바람직하게는 0 ℃ ∼ 100 ℃ 의 범위에서 실시하는 것이 바람직하다.
반응 시간은 반응 온도, 반응 기질, 반응량 등에 따라 상이하지만, 통상적으로 10 분 ∼ 48 시간이다.
반응의 목적물인 식 [1] 의 화합물은, 반응 종료 후, 정법에 의해 반응계로부터 채취되고, 필요에 따라 칼럼 크로마토그래피, 재결정 등의 조작에 의해 정제할 수도 있다.
<중간체 제조 방법 1>
[화학식 4]
(식 중, R1, R6, R7, R8, R9, R10, G1, T 및 n 은, 각각 (1) 에 정의한 바와 같고, L1 은 염소 원자, 브롬 원자 등의 할로겐 원자를 나타낸다.)
(공정 1)
식 [2] 의 화합물은, 식 [7] 의 화합물 (WO2008/013622 의 기재 등에 기초하여 제조 가능하다) 과 식 [5] 의 화합물을, 염기의 존재하/비존재하, 탈수 축합제 존재하, 용매 중에서 반응시키는 것에 의해 제조할 수 있다.
본 공정에서 사용하는 식 [5] 의 화합물의 사용량은, 식 [7] 의 화합물 1 몰에 대하여 0.5 ∼ 10 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 1.0 ∼ 1.2 몰이다.
본 공정에서 사용할 수 있는 탈수 축합제 및 염기로는, 제조 방법 2 공정 1 에서 설명한 것과 동일한 것을 들 수 있다.
본 반응에서 사용하는 탈수 축합제의 사용량은 식 [7] 의 화합물 1 몰에 대하여 1.0 ∼ 10 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 1.0 ∼ 3.0 몰이다.
본 반응에서 사용하는 염기의 사용량은 식 [7] 의 화합물 1 몰에 대하여 0 ∼ 100 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 0 ∼ 10 몰이다.
본 공정에서 사용할 수 있는 용매로는, 제조 방법 1 에서 설명한 것과 동일한 것을 들 수 있다.
본 반응에서 사용하는 용매의 사용량은 식 [7] 의 화합물 1 몰에 대하여 0.01 ∼ 100 ℓ 의 범위에서 적절히 선택하면 되고, 바람직하게는 0.1 ∼ 10 ℓ 이다.
반응 온도는 -20 ℃ 내지 사용하는 불활성 용매의 비점역의 범위에서 선택하면 되고, 바람직하게는 0 ℃ ∼ 100 ℃ 의 범위에서 실시하는 것이 바람직하다.
반응 시간은 반응 온도, 반응 기질, 반응량 등에 따라 상이하지만, 통상적으로 10 분 ∼ 48 시간이다.
(공정 2)
식 [2] 의 화합물은, 식 [7] 의 화합물과 식 [6] 의 화합물을, 염기의 존재하, 용매 중에서 반응시키는 것에 의해서도 제조할 수 있다.
본 공정에서 사용하는 식 [6] 의 화합물의 사용량은, 식 [7] 의 화합물 1 몰에 대하여 0.5 ∼ 10 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 1.0 ∼ 1.2 몰이다.
본 공정에서 사용할 수 있는 염기로는, 제조 방법 2 공정 1 에서 설명한 것과 동일한 것을 들 수 있다.
본 반응에서 사용하는 염기의 사용량은 식 [7] 의 화합물 1 몰에 대하여 0 ∼ 100 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 0 ∼ 10 몰이다.
본 공정에서 사용할 수 있는 용매로는, 제조 방법 1 에서 설명한 것과 동일한 것을 들 수 있다.
본 공정에서 사용하는 용매의 사용량은 식 [7] 의 화합물 1 몰에 대하여 0.01 ∼ 100 ℓ 의 범위에서 적절히 선택하면 되고, 바람직하게는 0.1 ∼ 10 ℓ 이다.
반응 온도는 -20 ℃ 내지 사용하는 불활성 용매의 비점역의 범위에서 선택하면 되고, 바람직하게는 0 ℃ ∼ 100 ℃ 의 범위에서 실시하는 것이 바람직하다.
반응 시간은 반응 온도, 반응 기질, 반응량 등에 따라 상이하지만, 통상적으로 10 분 ∼ 48 시간이다.
반응의 목적물인 식 [2] 의 화합물은, 반응 종료 후, 정법에 의해 반응계로부터 채취되고, 필요에 따라 칼럼 크로마토그래피, 재결정 등의 조작에 의해 정제할 수도 있다.
<중간체 제조 방법 2>
[화학식 5]
(식 중, R1, R2, R3, R4, R5, R6, X1, X2, X3, X4, T 및 n 은 각각 (1) 에 정의한 바와 같고, Y 는 1,1-디메틸에틸옥시카르보닐 또는 벤질 등의 아민 보호기를 나타낸다.)
식 [4] 로 나타내는 화합물은, 식 [9] 의 화합물을 적절한 방법을 사용하여 탈보호함으로써 조제할 수 있다 (아민 보호기의 방법에 대해서는, 예를 들어, T. W. Greene 및 P. G. Wuts 저, Protective Groups in Organic Synthesis, 제 4 판 ; Wiley : New York, 2007 을 참조). 아민의 보호기로는 다종 다양한 보호기가 적합하고, 적절한 보호기의 선택지는 화학 합성 분야의 당사자에게는 자명할 것이다. 탈보호 후, 종래 기술에 있어서 주지의 기본 방법에 의해, 식 [4] 의 아민을 산염 또는 유리 아민으로서 단리 가능하다.
식 [8] 로 나타내는 화합물과 식 [3] 으로 나타내는 화합물을, 용매 중, 산 또는 루이스산의 존재하에서 반응시킴으로써, 식 [9] 로 나타내는 본 발명 화합물을 제조할 수 있다.
여기서 사용하는 식 [3] 의 화합물의 사용량은, 식 [8] 의 화합물 1 몰에 대하여 1.0 ∼ 10 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 1.0 ∼ 3.0 몰이다.
본 공정에서 사용할 수 있는 산, 루이스산 및 용매는, 제조 방법 1 에서 설명한 것과 동일한 것을 들 수 있다.
산 또는 루이스산의 사용량은 식 [8] 의 화합물 1 몰에 대하여 0.01 ∼ 5 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 0.1 ∼ 1.0 몰이다.
용매의 사용량은 식 [8] 의 화합물 1 몰에 대하여 0.01 ∼ 100 ℓ 의 범위에서 적절히 선택하면 되고, 바람직하게는 0.1 ∼ 10 ℓ 이다.
반응 온도는 -20 ℃ 내지 사용하는 불활성 용매의 비점역의 범위에서 선택하면 되고, 바람직하게는 0 ℃ ∼ 150 ℃ 의 범위에서 실시하는 것이 바람직하다.
반응 시간은 반응 온도, 반응 기질, 반응량 등에 따라 상이하지만, 통상적으로 10 분 ∼ 48 시간이다.
반응의 목적물인 식 [9] 의 화합물은, 반응 종료 후, 정법에 의해 반응계로부터 채취되고, 필요에 따라 칼럼 크로마토그래피, 재결정 등의 조작에 의해 정제할 수도 있다.
<중간체 제조 방법 3>
[화학식 6]
(식 중, X1, X2, X3, X4 는 각각 (1) 에 정의한 바와 같다.)
식 [3a] 의 화합물은, 식 [10] 의 화합물을, 용매 중, 환원제를 사용하여 환원함으로써 제조할 수 있다.
본 공정에서 사용할 수 있는 환원제로는, 수소화알루미늄리튬, 수소화디이소부틸알루미늄, 보란 등을 들 수 있다.
환원제의 사용량은 식 [10] 의 화합물 1 몰에 대하여 1.0 ∼ 10 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 2.0 ∼ 5.0 몰이다.
본 공정에서 사용할 수 있는 용매로는, 제조 방법 1 에서 설명한 것과 동일한 것을 들 수 있다.
용매의 사용량은 식 [10] 의 화합물 1 몰에 대하여 0.01 ∼ 100 ℓ 의 범위에서 적절히 선택하면 되고, 바람직하게는 0.1 ∼ 10 ℓ 이다.
반응 온도는 -20 ℃ 내지 사용하는 불활성 용매의 비점역의 범위에서 선택하면 되고, 바람직하게는 0 ℃ ∼ 100 ℃ 의 범위에서 실시하는 것이 바람직하다.
반응 시간은 반응 온도, 반응 기질, 반응량 등에 따라 상이하지만, 통상적으로 10 분 ∼ 48 시간이다.
반응의 목적물인 식 [3a] 의 화합물은, 반응 종료 후, 정법에 의해 반응계로부터 채취되고, 필요에 따라 칼럼 크로마토그래피, 재결정 등의 조작에 의해 정제할 수도 있다.
<중간체 제조 방법 4>
[화학식 7]
(식 중, X1, X2, X3, X4 는 각각 (1) 에 정의한 바와 같고, R33 은 수소 원자 또는 C1 ∼ C4 알킬을 나타낸다.)
또한, 식 [3a] 의 화합물은, 식 [11] 의 화합물을, 용매 중, 환원제를 사용하여 환원하는 것에 의해서도 제조할 수 있다.
본 공정에서 사용할 수 있는 환원제로는, 중간체 제조 방법 3 에서 설명한 것과 동일한 것을 들 수 있다.
환원제의 사용량은 식 [11] 의 화합물 1 몰에 대하여 1.0 ∼ 10 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 2.0 ∼ 5.0 몰이다.
본 공정에서 사용할 수 있는 용매로는, 제조 방법 1 에서 설명한 것과 동일한 것을 들 수 있다.
용매의 사용량은 식 [11] 의 화합물 1 몰에 대하여 0.01 ∼ 100 ℓ 의 범위에서 적절히 선택하면 되고, 바람직하게는 0.1 ∼ 10 ℓ 이다.
반응 온도는 -20 ℃ 내지 사용하는 불활성 용매의 비점역의 범위에서 선택하면 되고, 바람직하게는 0 ℃ ∼ 100 ℃ 의 범위에서 실시하는 것이 바람직하다.
반응 시간은 반응 온도, 반응 기질, 반응량 등에 따라 상이하지만, 통상적으로 10 분 ∼ 48 시간이다.
반응의 목적물인 식 [3a] 의 화합물은, 반응 종료 후, 정법에 의해 반응계로부터 채취되고, 필요에 따라 칼럼 크로마토그래피, 재결정 등의 조작에 의해 정제할 수도 있다.
<중간체 제조 방법 5>
[화학식 8]
(식 중, R2, R3, X1, X2, X3, X4 는 각각 (1) 에 정의한 바와 같다.)
식 [3b] 의 화합물은, 식 [12] 의 화합물을, 용매 중, 환원제를 사용하여 환원함으로써 제조할 수 있다.
본 공정에서 사용할 수 있는 환원제로는, 중간체 제조 방법 3 에서 설명한 것과 동일한 것을 들 수 있다.
환원제의 사용량은 식 [12] 의 화합물 1 몰에 대하여 1.0 ∼ 10 몰의 범위에서 적절히 선택하면 되고, 바람직하게는 1.0 ∼ 3.0 몰이다.
본 공정에서 사용할 수 있는 용매로는, 제조 방법 1 에서 설명한 것과 동일한 것을 들 수 있다.
용매의 사용량은 식 [12] 의 화합물 1 몰에 대하여 0.01 ∼ 100 ℓ 의 범위에서 적절히 선택하면 되고, 바람직하게는 0.1 ∼ 10 ℓ 이다.
반응 온도는 -20 ℃ 내지 사용하는 불활성 용매의 비점역의 범위에서 선택하면 되고, 바람직하게는 0 ℃ ∼ 100 ℃ 의 범위에서 실시하는 것이 바람직하다.
반응 시간은 반응 온도, 반응 기질, 반응량 등에 따라 상이하지만, 통상적으로 10 분 ∼ 48 시간이다.
반응의 목적물인 식 [3b] 의 화합물은, 반응 종료 후, 정법에 의해 반응계로부터 채취되고, 필요에 따라 칼럼 크로마토그래피, 재결정 등의 조작에 의해 정제할 수도 있다.
식 [1] 의 화합물을 조제하기 위한 상기 서술한 몇 가지 시약 및 반응 조건이 중간체에 존재하는 특정한 관능기에 적합하지 않은 경우가 상정된다. 이들 예에 있어서, 합성에 보호/탈보호의 수법 또는 관능기의 상호 전환을 취입함으로써, 원하는 생성물을 얻을 수 있다. 보호기의 사용과 선택지에 대해서는 화학 합성 분야의 당업자이면 자명할 것이다 (예를 들어, T. W. Greene 및 P. G. Wuts 저, Protective Groups in Organic Synthesis, 제 4 판 ; Wiley : New York, 2007 을 참조). 경우에 따라서는, 개개의 스킴에서 설명한 바와 같이 특정한 시약을 도입 후, 식 [1] 의 화합물의 합성을 완료하기 위해서는 설명하지 않은 정법의 합성 공정을 추가로 실행할 필요가 있을 수 있는 것을 당업자는 인식할 것이다. 식 [1] 의 화합물을 조제하기 위해서 제안된 특정한 순서로 나타낸 것 이외의 순서로, 상기 스킴에 예시한 공정의 조합을 실행할 필요가 있을 수 있는 것도 당업자는 인식할 것이다.
본 명세서에 기재된 수법을 종래 기술에 있어서 주지의 방법과 병용함으로써, [표 1] ∼ [표 4] 에 나타내는 X1 ∼ X4 를 갖는 식 [1a] ∼ [1j] 화합물을 각각 조제 가능하다.
[화학식 9]
[표 1]
[표 2]
[표 3]
[표 4]
본 발명은, (a) 상기 식 [1] 로 나타내는 화합물 또는 그 농약상 허용되는 염을 적어도 1 종과, (b) 농원예용 살균 화합물 또는 그 염을 적어도 1 종을 활성 성분으로서 함유하는 것을 특징으로 하는 살균성 조성물이다. 구성 성분 (b) 는 FRAC (Fungicide Resistance Action Committee), 브리티시 크롭 프로텍션 카운실 발행의 페스티사이드 매뉴얼 (2013년), 일본 전국 농업 협동 조합 연합회 발행의 쿠미아이 농약 총람 (2014년) 및 일본 전국 농촌 교육 협회 발행의 SHIBUYA INDEX (제17판) 등으로 알려져 있는 화합물에서 선택할 수 있고, 하기에 FRAC 에 의한 예를 나타내지만, 이들에 한정되는 것은 아니다.
구성 성분 (b) 는, 「핵산 합성 저해제 (FRAC 코드 4, 8, 32, 31)」 : 베날락실 (benalaxyl), 베날락실-M (benalaxyl-M), 푸랄락실 (furalaxyl), 메탈락실 (metalaxyl), 메탈락실-M (metalaxyl-M), 옥사딕실 (oxadixyl), 오푸레이스 (ofurace), 부피리메이트 (bupirimate), 디메티리몰 (dimethirimol), 에티리몰 (ethirimol), 히멕사졸 (hymexazole), 옥틸리논 (octhilinone), 옥솔리닉산 (oxolinic acid) 등, 「유사 핵 분열과 세포 분열 저해제 (FRAC 코드 1, 10, 22, 20, 43, 39)」 : 베노밀 (benomyl), 카르벤다짐 (carbendazim), 푸베리다졸 (fuberidazole), 티아벤다졸 (thiabendazole), 티오파네이트 (thiophanate), 티오파네이트메틸 (thiophanate-methyl), 디에토펜카르브 (diethofencacrb), 족사미드 (zoxamide), 에타복삼 (ethaboxam), 펜시쿠론 (pencycuron), 플루오피콜리드 (fluopicolide) 등, 「호흡 저해제 (FRAC 코드 39, 7, 11, 21, 29, 30, 38, 45)」 : 디플루메토림 (diflumetorim), 톨펜피라드 (tolfenpyrad), 베노다닐 (benodanil), 플루톨라닐 (flutolanil), 메프로닐 (mepronil), 이소페타미드 (isofetamid), 플루오피람 (fluopyram), 펜푸람 (fenfuram), 카르복신 (carboxin), 옥시카르복신 (oxycarboxin), 티플루자미드 (thifluzamide), 벤조빈디플루피르 (benzovindiflupyr), 빅사펜 (bixafen), 플룩사피록사드 (fluxapyroxad), 푸라메트피르 (furametpyr), 이소피라잠 (isopyrazam), 펜플루펜 (penflufen), 펜티오피라드 (penthiopyrad), 세닥산 (sedaxane), 보스칼리드 (boscalid), 아족시스트로빈 (azoxystrobin), 쿠목시스트로빈 (coumoxystrobin), 에녹사스트로빈 (enoxastrobin), 플루페녹시스트로빈 (flufenoxystrobin), 피콕시스트로빈 (picoxystrobin), 피라클로스트로빈 (pyraclostrobin), 피라메토스트로빈 (pyrametostrobin), 트리클로피리카르브 (triclopyricarb), 크레속심메틸 (kresoxim-methyl), 트리플록시스트로빈 (trifloxystrobin), 디목시스트로빈 (dimoxystrobin), 페나민스트로빈 (fenaminstrobin), 메토미노스트로빈 (metominostrobin), 오리사스트로빈 (orysastrobin), 파목사돈 (famoxadone), 플루옥사스트로빈 (fluoxastrobin), 만데스트로빈 (mandestrobin), 피리미노스트로빈 (pyriminostrobin), 페나미돈 (fenamidone), 피리벤카르브 (pyribencarb), 시아조파미드 (cyazofamid), 아미술브롬 (amisulbrom), 아메톡트라딘 (ametoctradin) 등, 「아미노산 및 단백질 생합성 저해제 (FRAC 코드 9, 24, 25, 41)」 : 시프로디닐 (cyprodinil), 메파니피림 (mepanipyrim), 피리메타닐 (pyrimethanil), 블라스티사이딘-S (blasticidin-S), 카스가마이신 (kasugamycin), 스트렙토마이신 (streptomycin), 옥시테트라사이클린 (oxytetracycline) 등, 「시그널 전달 저해제 (FRAC 코드 13, 12, 2)」 : 퀴녹시펜 (quinoxyfen), 프로퀴나지드 (proquinazid), 펜피클로닐 (fenpiclonil), 플루디옥소닐 (fludioxonil), 클로졸리네이트 (chlozolinate), 이프로디온 (iprodione), 프로시미돈 (procymidone), 빈클로졸린 (vinclozolin) 등, 「지질 및 세포막 생합성 저해제 (FRAC 코드 6, 14, 28, 44)」 : 에디펜포스 (edifenphos), 이프로벤포스 (iprobenfos, IBP), 피라조포스 (pyrazophos), 이소프로티올란 (isoprothiolane), 비페닐 (biphenyl), 클로로네브 (chloroneb), 디클로란 (dicloran), 퀸토젠 (quintozene, PCNB), 테크나젠 (tecnazene, TCNB), 톨클로포스-메틸 (tolclofos-methyl), 에트리디아졸 (etridiazole), 이오도카르브 (iodocarb), 프로파마카르브 (propamacarb), 프로티오카르브 (prothiocarb), Bacillus subtilis syn., Bacillus amyloliquefaciens strain QST713, Bacillus amyloliquefaciens strain FZB24, Bacillus amyloliquefaciens strain MBI600, Bacillus amyloliquefaciens strain D747, extract from Melameuca alternifolia (tea tree) 등, 「세포막의 스테롤 생합성 저해제 (FRAC 코드 3, 5, 17, 18)」 : 트리포린 (triforine), 피리페녹스 (pyrifenox), 피리족사졸 (pyrizoxazole), 페나리몰 (fenarimol), 누아리몰 (nuarimol), 이마잘릴 (imazalil), 옥스포코나졸 (oxpoconazole), 페푸라조에이트 (pefurazoate), 프로클로라즈 (prochloraz), 트리플루미졸 (triflumizole), 아자코나졸 (azaconazole), 비테르타놀 (bitertanol), 브로무코나졸 (bromucoonazole), 시프로코나졸 (cyproconazoole), 디페노코나졸 (difenoconazole), 디니코나졸 (diniconazole), 에폭시코나졸 (epoxiconazole), 에타코나졸 (etaconazole), 펜부코나졸 (fenbuconazole), 플루퀸코나졸 (fluquinconazole), 플루실라졸 (flusilazole), 플루트리아홀 (flutriahol), 헥사코나졸 (hexaconazole), 이미벤코나졸 (imibenconazole), 입코나졸 (ipconazoole), 메토코나졸 (metconazole), 미클로부타닐 (myclobutanil), 펜코나졸 (penconazole), 프로피코나졸 (propiconazole), 시메코나졸 (simeconazole), 테부코나졸 (tebuconazole), 테트라코나졸 (tetraconazole), 트리아디메폰 (triadimefon), 트리아디메놀 (triadimenol), 트리티코나졸 (triticonazole), 프로티오코나졸 (prothioconazole), 알디모르프 (aldimorph), 도데모르프 (dodemorph), 펜프로피모르프 (fenpropimorph), 트리데모르프 (tridemorph), 펜프로피딘 (fenpropidin), 피페랄린 (piperalin), 스피록사민 (spiroxamine), 펜헥사미드 (fenhexamid), 펜피라자민 (fenpyrazamine), 피리부티카르브 (pyributicarb), 나프티핀 (naftifine), 테르비나핀 (terbinafine) 등, 「세포벽 생합성 저해제 (FRAC 코드 26, 19, 40)」 : 발리다마이신 (validamycin), 폴리옥신 (polyoxin), 디메토모르프 (dimethomorph), 플루모르프 (flumorph), 피리모르프 (pyrimorph), 벤티아발리카르브 (benthiavalicarb), 이프로발리카르브 (iprovalicarb), 발리페날레이트 (valifenalate), 만디프로파미드 (mandipropamid) 등, 「세포벽의 멜라닌 합성 저해제 (FRAC 코드 16.1, 16.2, 16.3)」 : 프탈라이드 (fthalide), 피로퀼론 (pyroquilon), 트리시클라졸 (tricyclazole), 카르프로파미드 (carpropamid), 디클로시메트 (diclocymet), 페녹사닐 (fenoxanil), 톨프로카르브 (tolprocarb) 등, 「숙주 식물의 저항성 유도제 (FRAC 코드 P1 ∼ P5)」 : 아시벤졸라르-S-메틸 (acibenzolar-S-methyl), 프로베나졸 (probenazole), 티아디닐 (tiadinil), 이소티아닐 (isotianil), 라미나린 (laminarin), extract from Reynoutria sachalinensis (giant knotweed) 등, 「다작용점 접촉 저해제 (FRAC 코드 M1 ∼ M11)」 : 동 (copper), 황 (sulphur), 파밤 (ferbam), 만제브 (mancozeb), 마네브 (maneb), 메티람 (metiram), 프로피네브 (propineb), 티람 (thiram), 지네브 (zineb), 지람 (ziram), 캡탄 (captan), 캡타폴 (captafol), 폴펫 (folpet), 클로로탈로닐 (chlorothalonil), 디클로플루아니드 (dichlofluanid), 톨리플루아니드 (tolyfluanid), 구아자틴 (guazatine), 이미녹타딘 (iminoctadine), 아닐라진 (anilazine), 디티아논 (dithianon), 퀴녹살린계 (chinomethioonat/quinomethionate), 플루오로이미드 (fluoroimide) 등, 「작용 기구 불명 (FRAC 코드 27, 33, 34, 35, 36, 37, 42, U6, U8, U12 ∼ U17)」 : 시목사닐 (cymoxanil), 포세틸-알루미늄 (fosetyl-Al), 아인산 (phosphorous acid and salts), 테클로프탈람 (teclofthalam), 트리아족시드 (triazoxide), 플루술파미드 (flusulfamide), 디클로메진 (diclomezine), 메타술포카르브 (methasulfocarb), 시플루페나미드 (cyflufenamid), 메트라페논 (metrafenone), 피리오페논 (pyriofenone), 도딘 (dodine), 플루티아닐 (flutianil), 페림존 (ferimzone), 테부플로퀸 (tebufloquin), 옥사티아피프롤린 (oxathiapiprolin), 피카르부트라족스 (picarbutrazox) 등. 이 밖에도, BAF-1107, BAF-1120, KUF-1411, MIF-1002, MIF-1102, NNF-0721, NC-233, NF-171, NF-180, S-2399, SYJ-247, SYJ-252, SYJ-264, SYJ-269 등을 조합예로서 들 수 있다.
본 발명에 의한 살균성 조성물은, 다종 다양한 군에서 선택되는 구성 성분 (b) 와 상기 식 [1] 을 조합하여 사용함으로써 우수한 상승 효과를 발휘한다.
본 발명의 살균성 조성물은, 식물 병원균에 대하여 매우 강력한 살균 활성을 가지고 있고, 식물 병원성 미생물, 예를 들어, 뿌리혹병균문 (Plasmodiophoromycota), 난균문 (Oomycota) 에 속하는 원생 생물, 접합균문 (Zygomycota), 자낭균문 (Ascomycota), 담자균문 (Basidiomycota), 및 불완전균문 (Deuteromycota) 등에 속하는 균류, 그리고, 예를 들어, 슈도모나스과 (Pseudomonadaceae), 리조븀과 (Rhizobiaceae), 장내 세균과 (Enterobacteriaceae), 코리네박테리움과 (Corynebacteriaceae) 및 스트렙토미세스과 (Streptomycetaceae) 등에 속하는 세균, 그리고 이들에 의해 발생하는 식물 병해를 방제하기 위해서 사용할 수 있다. 또한, 본 발명에 의한 살균성 조성물은, 뿌리혹병균문 및 난균문에 속하는 원생 생물에 특히 높은 상승적인 살균 활성을 나타내는 점에서, 이에 의해 발생하는 식물 병해가 우수한 방제 효과를 나타낸다.
이하에 본 발명에 따라 방제하는 것이 가능한 식물 병원성 미생물의 예를 들지만, 반드시 이들에 한정되는 것은 아니다.
난균문 (Oomycota) 에 속하는 병원성 미생물의 예로는 ;
흰녹가루병 (white rust) 의 병원체인 알부고 (Albugo) 속 원생 생물, 예를 들어 알부고 칸디다 (Albugo candida) ;
근부병 (root rot), 모잘록병 (damping-off) 의 병원체인 아파노미세스 (Aphanomyces) 속 원생 생물, 예를 들어 아파노미세스 에우테이케스 (Aphanomyces euteiches) ;
노균병 (downy mildew) 의 병원체인 브레미아 (Bremia) 속 원생 생물, 예를 들어 브레미아 락투카에 (Bremia lactucae) ;
노균병 (downy mildew) 의 병원체인 페로노스포라 (Peronospora) 속 원생 생물, 예를 들어 페로노스포라 피시 (Peronospora pisi), 페로노스포라 브라시카에 (Peronospora brassicae), 페로노스포라 파라시티카 (Peronospora parasitica), 페로노스포라 타바시나 (Peronospora tabacina) ;
노균병 (downy mildew) 의 병원체인 플라스모파라 (Plasmopara) 속 원생 생물, 예를 들어 플라스모파라 비티콜라 (Plasmopara viticola) ;
노균병 (downy mildew) 의 병원체인 프세우도페로노스포라 (Pseudoperonospora) 속 원생 생물, 예를 들어 프세우도페로노스포라 쿠벤시스 (Pseudoperonospora cubensis), 프세우도페로노스포라 후물리 (Pseudoperonospora humuli) ;
역병 (late blight, white powdery rot), 갈색 부패병 (brown rot), 근부역병 (red stele), 심부병 (heart rot), 면역병 (phytophthora rot) 의 병원체인 피토프토라 (Phytophthora) 속 원생 생물, 예를 들어 피토프토라 칵토룸 (Phytophthora cactorum), 피토프토라 캅시시 (Phytophthora capsici), 피토프토라 신나모니 (Phytophthora cinnamoni), 피토프토라 인페스탄스 (Phytophthora infestans), 피토프토라 메가스페르마 (Phytophthora megasperma), 피토프토라 파라시티카 (Phytophthora parasitica) ;
근부병 (root rot), 모잘록병 (damping-off), 근부병 (browning root rot), 무병 (bed rot) 의 병원체인 피티움 (Pythium) 속 원생 생물, 예를 들어 피티움 아파니데르마툼 (Pythium aphanidermatum), 피티움 울티뭄 (Pythium ultimum) 을 들 수 있다.
사족충문 (Cercozoa) 에 속하는 병원성 미생물의 예로는, 뿌리 혹병 (club root) 의 병원체인 플라스모디오포라 (Plasmodiophora) 속 원생 생물, 예를 들어 플라스모디오포라 브라시카에 (Plasmodiophora brassicae) 를 들 수 있다.
접합균문 (Zygomycota) 에 속하는 병원성 미생물의 예로는, 모잘록병 (seedling blight), 부패병 (bulb rot), 흑곰팡이병 (Rhizopus rot), 연부병 (soft rot) 의 병원체인 리조푸스 (Rhizopus) 속 균류, 예를 들어 리조푸스 스톨로니페르 (Rhizopus stolonifer) 를 들 수 있다.
자낭균문 (Ascomycota) 에 속하는 병원성 미생물의 예로는 ;
화부병 (ray blight), 갈반병 (brown spot), 윤문병 (Ascochyta leaf spot), 흑반병 (leaf spot) 의 병원체인 아스코키타 (Ascochyta) 속 균류, 예를 들어 아스코키타 렌티스 (Ascochyta lentis) ;
흰가루병 (powdery mildew) 의 병원체인 블루메리아 (Blumeria) 속 균류, 예를 들어 블루메리아 그라미니스 (Blumeria graminis) ;
맥각병 (ergot), 벼이삭누룩병 (false smut) 의 병원체인 클라비셉스 (Claviceps) 속 균류, 예를 들어 클라비셉스 푸르푸레아 (Claviceps purpurea) ;
깨시무늬병 (southern leaf blight), 반점병 (spot blotch), 갈조병 (brown stripe) 의 병원체인 코클리오볼루스 (Cochliobolus) 속 균류, 예를 들어 코클리오볼루스 사티부스 (Cochliobolus sativus), 코클리오볼루스 미야베아누스 (Cochliobolus miyabeanus), 코클리오볼루스 사티부스 (Cochliobolus sativus) ;
동고병 (diaporthe canker) 의 병원체인 디아포르테 (Diaporthe) 속 균류, 예를 들어 디아포르테 시트리 (Diaporthe citri) ;
흑두병 (anthracnose), 더뎅이병 (scab), 흑두병 (sphaceloma scab), 백색옴 (white scab), 검은무늬병 (leaf spot) 의 병원체인 엘시노에 (Elsinoe) 속 균류, 예를 들어 엘시노에 파우세티이 (Elsinoe fawcettii), 에리시페 그라미니스 (Erysiphe graminis), 에리시페 폴리고니 (Erysiphe polygoni) ;
입고병 (take-all) 의 병원체인 가에우만노미세스 (Gaeumannomyces) 속 균류, 예를 들어 가에우만노미세스 그라미니스 (Gaeumannomyces graminis) ;
아고병 (twig blight), 벼키다리병 (bakanae disease), 아부병 (bud rot), 입고병 (stub dieback) 의 병원체인 지베렐라 (Gibberella) 속 균류, 예를 들어 지베렐라 제아에 (Gibberella zeae) ;
탄저병 (anthracnose), 만부병 (ripe rot), 적부병 (red rot), 반점병 (leaf spot) 의 병원체인 글로메렐라 (Glomerella) 속 균류, 예를 들어 글로메렐라 신굴라타 (Glomerella cingulata) ;
구이그나르디아 (Guignardia) 속 균류, 예를 들어 구이그나르디아 비드웰리 (Guignardia bidwellii) ;
검은균핵병 (stem rot), 실버 스커프병 (silver scurf), 겹둥근무늬병 (zonate leaf spot) 의 병원체인 헬민토스포륨 (Helminthosporium) 속 균류, 예를 들어 헬민토스포륨 시그모이데움 (Helminthosporium sigmoideum), 헬민토스포륨 솔라니 (Helminthosporium solani), 헬민토스포륨 트리티시레펜티스 (Helminthosporium triticirepentis), 헬민토스포륨 조나툼 (Helminthosporium zonatum) ;
경고병 (blight), 윤반병 (ring spot) 의 병원체인 렙토스파에리아 (Leptosphaeria) 속 균류, 예를 들어 렙토스파에리아 준시나 (Leptosphaeria juncina), 렙토스파에리아 마쿨란스 (Leptosphaeria maculans), 렙토스파에리아 사카리 (Leptosphaeria sacchari) ;
소구균핵병 (stem rot) 의 병원체인 마그나포르테 (Magnaporthe) 속 균류, 예를 들어 마그나포르테 그리세아 (Magnaporthe grisea), 마그나포르테 살비니 (Magnaporthe salvinii) ;
회성병 (brown rot), 꽃부패병 (blossom blight) 의 병원체인 모닐리니아 (Monilinia) 속 균류, 예를 들어 모닐리니아 프룩티콜라 (Monilinia fructicola), 모닐리니아 락사 (Monilinia laxa), 모닐리니아 말리 (Monilinia mali) ;
갈색엽고병 (leaf scald), 홍색설부병 (snow mold) 의 병원체인 모노그라펠라 (Monographella) 속 균류, 예를 들어 모노그라펠라 알베센사 (Monographella albescensa), 모노그라펠라 니발리스 (Monographella nivalis) ;
흑삽병 (black leaf blight), 갈반병 (leaf spot) 의 병원체인 마이코스파에렐라 (Mycosphaerella) 속 균류, 예를 들어 마이코스파에렐라 아라키디콜라 (Mycosphaerella arachidicola), 마이코스파에렐라 피지엔시스 (Mycosphaerella fijiensis), 마이코스파에렐라 그라미니콜라 (Mycosphaerella graminicola) ;
파에오모니엘라 (Phaeomoniella) 병의 병원체인 파에오모니엘라 (Phaeomoniella) 속 균류, 예를 들어 파에오모니엘라 클라미도스포라 (Phaeomoniella chlamydospora) ;
밀껍질마름병 (glume blotch) 의 병원체인 파에오스파에리아 (Phaeosphaeria) 속 균류, 예를 들어 파에오스파에리아 노도룸 (Phaeosphaeria nodorum) ;
흰가루병 (powdery mildew) 의 병원체인 포도스파에라 (Podosphaera) 속 균류, 예를 들어 포도스파에라 레우코트리카 (Podosphaera leucotricha), 포도스파에라 트리닥틸라 (Podosphaera tridactyla) ;
반엽병 (stripe), 망반병 (net blotch) 의 병원체인 피레노포라 (Pyrenophora) 속 균류, 예를 들어 피레노포라 그라미네아 (Pyrenophora graminea), 피레노포라 테레스 (Pyrenophora teres) ;
황화 오갈병 (downy mildew), 균핵병 (sclerotinia rot) 의 병원체인 스클레로티니아 (Sclerotinia) 속 균류, 예를 들어 스클레로티니아 스클레로티오람 (Sclerotiniasclerotiorum) ;
백견병 (southern blight), 흑부균핵병 (white rot) 의 병원체인 스클레로티움 (Sclerotium) 속 균류, 예를 들어 스클레로티움 롤프시 (Sclerotium rolfsii) ;
흰가루병 (powdery mildew) 의 병원균인 스파에로테카 (Sphaerotheca) 속 균류, 예를 들어 스파에로테카 풀리기네아 (Sphaerotheca fuliginea), 스파셀로테카 레일리아나 (Sphacelotheca reiliana) ;
갈색점무늬병 (cercospora leaf spot) 의 병원체인 스파에룰리나 (Sphaerulina) 속 균류, 예를 들어 스파에룰리나 오리지나 (Sphaerulina oryzina) ;
타페시아 (Tapesia) 병의 병원균인 타페시아 (Tapesia) 속 균류, 예를 들어 타페시아 아쿠포르미스 (Tapesia acuformis) ;
축엽병 (leaf curl), 주머니병 (plum pockets) 의 병원체인 타프리나 (Taphrina) 속 균류, 예를 들어 타프리나 데포르만스 (Taphrina deformans), 타프리나 프루니 (Taphrina pruni) ;
흰가루병 (powdery mildew) 의 병원체인 운시눌라 (Uncinula) 속 균류, 예를 들어 운시눌라 네카토르 (Uncinula necator), 운시눌라 시물란스 (Uncinuliella simulans) ;
흑성병 (scab) 의 병원체인 벤투리아 (Venturia) 속 균류, 예를 들어 벤투리아 이나에쿠알리스 (Venturia inaequalis), 벤투리아 나시콜라 (Venturia nashicola) 를 들 수 있다.
담자균문 (Basidiomycota) 에 속하는 병원성 미생물의 예로는 ;
밑둥썩음병 (foot-rot), 동문고병 (winter stem rot) 의 병원체인 세라토바시디움 (Ceratobasidium) 속 균류, 예를 들어 세라토바시디움 그라미네람 (Ceratobasidium graminerum) ;
밑둥썩음병 (foot-rot), 동문고병 (winter stem rot) 의 병원체인 코르티시움 (Corticium) 속 균류, 예를 들어 코르티시움 그라미네람 (Corticium graminerum) ;
떡병 (leaf gall), 빗자루병 (witches broom), 망병병 (net blister blight) 의 병원체인 엑소바시디움 (Exobasidium) 속 균류, 예를 들어 엑소바시디움 펜타스포리움 (Exobasidium pentasporium), 엑소바시디움 레티쿨라탐 (Exobasidium reticulatum), 엑소바시디움 벡산스 (Exobasidium vexans) ;
오갈병 (Dwarf) 의 병원체인 포미티포리아 (Fomitiporia) 속 균류, 예를 들어 포미티포리아 메디테라네아 (Fomitiporia mediterranea) ;
영지버섯 (Stem rot) 의 병원체인 가노데르마 (Ganoderma) 속 균류, 예를 들어 가노데르마 보니넨세 (Ganoderma boninense) ;
빨간녹병 (rust) 의 병원균인 김노스포란기움 (Gymnosporangium) 속 균류, 예를 들어 김노스포란기움 사비나에 (Gymnosporangium sabinae), 김노스포란기움 사비나에 (Gymnosporangium sabinae) ;
녹병 (rust) 의 병원균인 헤밀레이아 (Hemileia) 속 균류, 예를 들어 헤밀레이아 바스타트릭스 (Hemileia vastatrix) ;
코랄 스폿병 (coral spot disease), 입고병 (nectria blight) 의 병원체인 넥트리아 (Nectria) 속 균류, 예를 들어 넥트리아 갈리게나 (Nectria galligena) ;
갈녹병, 녹병 (rust) 의 병원체인 파콥소라 (Phakopsora) 속 균류, 예를 들어 파콥소라 메이보미아에 (Phakopsora meibomiae), 파콥소라 파키리지 (Phakopsora pachyrhizi) ;
녹병 (rust), 흑녹병 (stem rust), 적녹병 (leaf rust) 의 병원체인 푸시니아 (Puccinia) 속 균류, 예를 들어 푸시니아 아라키디스 (Puccinia arachidis), 푸시니아 그라미니스 (Puccinia graminis), 푸시니아 호르데이 (Puccinia hordei), 푸시니아 레콘디타 (Puccinia recondita), 푸시니아 스트리이포르미스 (Puccinia striiformis) ;
비린깜부기병 (Stinking smut) 의 병원균인 틸레티아 (Tilletia) 속 균류, 예를 들어 틸레티아 카리에스 (Tilletia caries) ;
설부소립균핵병 (typhula snow blight), 소립균핵 부패병 (typhula rot) 의 병원체인 티풀라 (Typhula) 속 균류, 예를 들어 티풀라 인카르나타 (Typhula incarnata), 티풀라 이시카리엔시스 (Typhula ishikariensis) ;
깜부기병 (smut) 의 병원체인 우로시스티스 (Urocystis) 속 균류, 예를 들어 우로시스티스 세풀라에 (Urocystis cepulae), 우로시스티스 오쿨타 (Urocystis occulta) ;
녹병 (rust) 의 병원체인 우로미세스 (Uromyces) 속 균류, 예를 들어 우로미세스 아펜디쿨라쿠스 (Uromyces appendiculatus), 우로미세스 파세올리 (Uromyces phaseoli) ;
깜부기병 (smut), 겉깜부기병 (loose smut) 의 병원체인 우스틸라고 (Ustilago) 속 균류, 예를 들어 우스틸라고 마이디스 (Ustilago maydis), 우스틸라고 누다 (Ustilago nuda) 를 들 수 있다.
불완전균문 (Deuteromycota) 에 속하는 병원성 미생물의 예로는 ;
흑반병 (Alternaria blotch, Alternaria leaf spot, Alternaria black rot), 흑엽고병 (leaf blight), 여름 역병 (early blight), 윤문병 (early blight) 의 병원체인 알터나리아 (Alternaria) 속 균류, 예를 들어 알터나리아 브라시시콜라 (Alternaria brassicicola), 알터나리아 솔라니 (Alternaria solani) ;
흑곰팡이병 (crown rot) 의 병원체인 아스페르길루스 (Aspergillus) 속 균류, 예를 들어 아스페르길루스 플라부스 (Aspergillus flavus) ;
회색 곰팡이병 (gray mold), 회색 부패병 (neck rot), 적색 반점병 (red spot) 의 병원체인 보트리티스 (Botrytis) 속 균류, 예를 들어 보트리티스 시네레아 (Botrytis cinerea) ;
흑삽병 (leaf spot) 의 병원체인 세르코스포리디움 (Cercosporidium) 속 균류, 예를 들어 세르코스포리디움 페르소나툼 (Cercosporidium personatum) ;
반점병 (leaf spot), 갈반병 (leaf spot), 갈색 원성병 (brown round spot), 엽고병 (leaf blight), 자반병 (purple stain) 의 병원체인 세르코스포라 (Cercospora) 속 균류, 예를 들어 세르코스포라 아라키디콜라 (Cercospora arachidicola), 세르코스포라 베티콜라 (Cercospora beticola), 세르코스포라 차에 (Cercospora chaae), 세르코스포라 키쿠치 (Cercospora kikuchii) ;
흑성병 (scab), 가짜도열병 (false blast), 반엽병 (leaf blotch) 의 병원균인 클라도스포리움 (Cladosporium) 속 균류, 예를 들어 클라도스포리움 쿠쿠메리눔 (Cladosporium cucumerinum), 클라도스포리움 클라도스포리오이데스 (Cladosporium cladosporioides), 클라도스포리움 헤르바룸 (Cladosporium herbarum) ;
탄저병 (anthracnose), 만부병 (ripe rot) 의 병원균인 콜레토트리쿰 (Colletotrichum) 속 균류, 예를 들어 콜레토트리쿰 코코데스 (Colletotrichum coccodes), 콜레토트리쿰 그라미니콜라 (Colletotrichum graminicola), 콜레토트리쿰 린데무타니움 (Colletotrichum lindemuthanium), 콜레토트리쿰 오르비쿨라레 (Colletotrichum orbiculare) ;
위황병 (stem rot), 시들음병 (Fusarium wilt), 건부병 (dry rot), 근부위조병 (root rot), 입고병 (Fusarium wilt) 의 병원체인 푸사리움 (Fusarium) 속 균류, 예를 들어 푸사리움 쿨모룸 (Fusarium culmorum), 푸사리움 그라미네아룸 (Fusarium graminearum), 푸사리움 옥시스포룸 (Fusarium oxysporum), 푸사리움 로세움 (Fusarium roseum) ;
탄저병 (anthracnose) 의 병원체인 글로에오스포리움 (Gloeosporium) 속 균류, 예를 들어 글로에오스포리움 라에티콜로르 (Gloeosporium laeticolor) ;
반점병 (leaf spot), 백반병 (Macrophoma leaf spot), 동고병 (branch canker) 의 병원균인 마크로포미나 (Macrophomina) 속 균류, 예를 들어 마크로포미나 테이콜라 (Macrophoma theicola), 마크로포미나 파세올리나 (Macrophomina phaseolina) ;
천공병 (anthracnose) 의 병원체인 미크로도키움 (Microdochium) 속 균류, 예를 들어 미크로도키움 니발레 (Microdochium nivale) ;
푸른곰팡이병 (blue mold), 초록 곰팡이병 (common green mold) 의 병원체인 페니실리움 (Penicillium) 속 균류, 예를 들어 페니실리움 엑스판숨 (Penicillium expansum), 예를 들어 페니실리움 푸르푸로게눔 (Penicillium purpurogenum) ;
뱀눈무늬병 (leaf spot), 열매썩음병 (fruit rot), 근후병 (root rot) 의 병원체인 포마 (Phoma) 속 균류, 예를 들어 포마 린감 (Phoma lingam) ;
예를 들어 포마 다우시 (Phoma dauci) ;
동고병 (Phomopsis canker), 경고병 (stem blight) 의 병원체인 포몹시스 (Phomopsis) 속 균류, 예를 들어 포몹시스 소자에 (Phomopsis sojae), 포몹시스 비티콜라 (Phomopsis viticola) ;
안문병 (eye spot) 의 병원균인 프소이도세르코스포렐라 (Pseudocercosporella) 속 균류, 예를 들어 프소이도세르코스포렐라 헤르포트리코이데스 (Pseudocercosporella herpotrichoides) ;
도열병 (blast) 의 병원체인 피리쿨라리아 (Pyricularia) 속 균류, 예를 들어 피리쿨라리아 오리자에 (Pyricularia oryzae) ;
반점병 (Ramularia leaf spot) 의 병원체인 라물라리아 아레올라 (Ramularia) 속 균류, 예를 들어 라물라리아 아레올라 (Ramularia areola), 라물라리아 콜로-시그니 (Ramularia collo-cygni) ;
모잘록병 (damping-off), 근부병 (Rhizoctonia root rot), 경부병 (stem rot), 문고병 (sheath blight) 의 병원체인 리족토니아 (Rhizoctonia) 속 균류, 예를 들어 리조푸스 오리자에 (Rhizopus oryzae), 리족토니아 솔라니 (Rhizoctonia solani) ;
운형병 (leaf blotch) 의 병원체인 린코스포리움 (Rhynchosporium) 속 균류, 예를 들어 린코스포리움 세칼리스 (Rhynchosporium secalis) ;
엽초 부패병 (sheath rot) 의 병원체인 사로클라디움 (Sarocladium) 속 균류, 예를 들어 사로클라디움 오리자에 (Sarocladium oryzae) ;
흑점엽고병 (black spotted leaf blight), 엽고병 (leaf blight), 갈반병 (Septoria leaf spot) 의 병원체인 셉토리아 (Septoria) 속 균류, 예를 들어 셉토리아 아피이 (Septoria apii), 셉토리아 리코페르시시 (Septoria lycopersici), 셉토리아 노도룸 (Septoria nodorum), 셉토리아 트리티시 (Septoria tritici) ;
적반병 (red leaf spot), 반점병 (leaf scorch) 의 병원체인 스타고노스포라 (Stagonospora) 속 균류, 스타고노스포라 노도룸 (Stagonospora nodorum) ;
흑근병 (black root rot), 근부병 (root rot) 의 병원균인 티엘라비옵시스 (Thielaviopsis) 속 균류, 예를 들어 티엘라비옵시스 바시콜라 (Thielaviopsis basicola) ;
반신 위조병 (verticillium wilt) 의 병원체인 버티실리움 (Verticilium) 속 균류, 예를 들어 버티실리움 알보아트룸 (Verticilium alboatrum), 버티실리움 달리아에 (Verticillium dahliae) 를 들 수 있다.
크산토모나스과 (Xanthomonadaceae) 에 속하는 병원성 미생물의 예로는, 흰색엽고병 (bacterial leaf blight), 반점 세균병 (bacterial spot), 갈반 세균병 (bacterial brown spot) 의 병원체인 크산토모나스 (Xanthomonas) 속 세균, 예를 들어 크산토모나스 캄페스트리스 파소바 오리자에 (Xanthomonas campestris pv. oryzae), 크산토모나스 캄페스트리스 파소바 베시카토리아 (Xanthomonas campestris pv.. vesicatoria) 들 수 있다.
슈도모나스과 (Pseudomonadaceae) 에 속하는 병원성 미생물의 예로는, 엽초 갈변병 (sheath blown rot), 위조 세균병 (bacterial wilt) 의 병원체인 슈도모나스 (Pseudomonas) 속 세균, 예를 들어 슈도모나스 시린가에 파소바 라크리만스 (Pseudomonas syringae pv. lachrymans), 슈도모나스 시린가에 파소바 모리 (Pseudomonas syringae pv. mori) 를 들 수 있다.
장내 세균과 (Enterobacteriaceae) 에 속하는 병원성 미생물의 예로는, 연부병 (bacterial soft rot) 의 병원체인 에르비니아 (Ervinia) 속 세균, 예를 들어 에르비니아 아밀로보라 (Erwinia amylovora), 에르비니아 카로토보라 서브스피시즈 카로토보라 (Erwinia carotovora subsp. carotovora) 들 수 있다.
코리네박테리움과 (Corynebacteriaceae) 세균의 예로는, 대화병 (fasciation) 의 병원체인 코리네박테리움 (Corynebacterium) 속 세균, 예를 들어 코리네박테리움 파시안스 (Corynebacterium facians) 를 들 수 있다.
스트렙토마이세스과 (Streptomycetaceae) 에 속하는 병원성 미생물의 예로는, 토취황변미 (Soil smelling yellow rice) 의 병원체인 스트렙토마이세스속 (Streptmyces) 세균, 예를 들어 스트렙토마이세스 플라보비렌스 (Streptmyces flavovirens) 를 들 수 있다.
본 발명의 식물 유해 생물의 방제 방법에 있어서는, (a) 식 [1] 로 나타내는 화합물, 및 (b) 농원예용 살균제 또는 그 염을, 식물 또는 식물 주변의 영역에 처리하는 공정을 포함하고, 성분 (a) 및 성분 (b) 가 동시에, 연속해서, 또는 따로따로 처리된다. 여기서 식물이란, 야생 식물, 육성 식물, 자연 발생 식물 및 재배 식물 등의 식물 또는 식물군을 가리키고, 도입 육종법, 분리 육종법, 교잡 육종법, 잡종 강세 육종법, 돌연 변이 육종법, 배수성 육종법, 유전자 재조합 (유전자 도입) 법, 또는 마커 지원 선발 등의 육종법에 의해 작출된 식물도 포함된다. 또한, 처리하는 식물은, 식물의 전체 및 식물의 일부의 어느 것이어도 된다. 또한, 식물 주변의 영역이란, 토양 (종자를 파종하는 토양), 논, 수경 재배의 물, 재배 자재 등을 가리킨다. 더하여, 식물 또는 식물 주변의 영역에 대한 처리란, 분무, 산포, 살분, 스프레이, 확산, 침지, 관주, 주입, 살수 (침수), 발포, 도포, 분의, 코팅, 분사, 훈증, 훈연, 연무, 도장 등을 가리킨다.
식물 병원 미생물 또는 그것에 의해 발생하는 식물 병해를 방제하기 위해서 본 발명에 의한 살균성 조성물을 처리하는 경우, 처리는 식물 병원성 미생물의 감염의 전후에 관계없이, 식물의 생육 기간 및 저장 기간을 통해서 실시할 수 있다. 여기서, 식물의 일부란, 식물의 잎, 줄기, 나무줄기, 가지, 꽃, 자실체, 과실, 종자, 뿌리, 덩이 줄기 및 뿌리 줄기 등, 식물을 구성하는 모든 부분 또는 그 조합을 의미한다.
식물 병원성 미생물 및 이에 의해 발생하는 식물 병해를 방제하기 위해서, 본 발명에 의한 살균성 조성물을 유효하지만 식물에 독성을 나타내지 않는 양이 되도록 처리량을 조정하여, 사용할 수 있다. 여기서, 유효하지만 식물에 독성을 나타내지 않는 양이란, 식물 병원성 미생물 또는 이에 의해 발생하는 식물 병해를 충분히 방제할 수 있고, 또한, 식물에 해를 주지 않는 양이고, 이 양은 방제하는 미생물, 적용하는 식물, 사용되는 자연 환경 및 본 발명에 의한 조성물의 성분에 따라, 비교적 넓은 범위에서 변동할 수 있다.
이하에, 본 발명에 의한 살균성 조성물로 처리할 수 있는 식물의 예를 들지만, 반드시 이것에 한정되는 것은 아니다.
즉 ;
아욱과 (Malvaceae) 식물, 예를 들어, 오크라, 목화 ;
벽오동과 (Sterculiaceae) 식물, 예를 들어, 카카오 나무 ;
아카자과 (Chenopodiaceae) 식물, 예를 들어, 시금치 ;
사포타과 (Sapotaceae) 식물, 예를 들어, 미러클 프루츠 ;
꼭두서니과 (Rubiaceae) 식물, 예를 들어, 커피나무, 로브스타 커피나무 ;
삼과 (Cannabaceae) 식물, 예를 들어, 홉 ;
십자화과 (Brassicaceae) 식물, 예를 들어, 유채, 순무, 콜리플라워, 양배추, 소송채, 무우, 청경채, 배추, 브로콜리 ;
벼과 (Poaceae) 식물, 예를 들어, 벼, 대맥, 밀, 사탕수수, 잔디, 옥수수, 호밀 ;
박과 (Cucurbitaceae) 식물, 예를 들어, 호박, 오이, 수박, 애호박, 동과, 여주, 차요태, 참외, 멜론, 박 ;
옻나무과 (Anacardiaceae) 식물, 예를 들어, 망고 ;
분꽃과 (Nyctaginaceae) 식물, 예를 들어, 땅두릅나무 ;
물레나물과 (Clusiaceae) 식물, 예를 들어, 망고스틴 ;
감나무과 (Ebenaceae) 식물, 예를 들어, 감나무 ;
국화과 (Asteraceae) 식물, 예를 들어, 상추, 잎상추, 양상추, 국화, 쑥갓, 치커리, 우엉, 해바라기, 머위 ;
자작나무과 (Betulaceae) 식물 ;
말피기과 (Malpighiaceae) 식물, 예를 들어, 아세롤라 ;
녹나무과 (Lauraceae) 식물 ;
보리수나무과 (Elaeagnaceae) 식물, 예를 들어, 가래나무, 블랙 월넛 ;
뽕나무과 (Moraceae) 식물, 예를 들어, 무화과나무, 고무나무 ;
잔고사리과 (Dennstaedtiaceae) 식물, 예를 들어, 고사리 ;
참깨과 (Pedaliaceae) 식물, 예를 들어, 참깨 ;
석류나무과 (Punicaceae) 식물, 예를 들어, 석류나무 ;
천남성과 (Araceae) 식물, 예를 들어, 곤약, 토란 ;
새깃아재비과 (Blechnaceae) 식물, 예를 들어, 사자두 ;
꿀풀과 (Lamiaceae) 식물, 예를 들어, 푸른차조기, 붉은차조기 ;
피나무과 (Tiliaceae) 식물, 예를 들어, 몰로헤이야 ;
생강과 (Zingiberaceae) 식물, 예를 들어, 울금, 진저, 생강, 양하 ;
산형과 (Apiaceae) 식물, 예를 들어, 파슬리, 샐러리, 당근 ;
마디풀과 (Polygonaceae) 식물, 예를 들어, 메밀 ;
진달래과 (Ericaceae) 식물, 예를 들어, 진달래 ;
동백나무과 (Theaceae) 식물, 예를 들어, 차나무 ;
가지과 (Solanaceae) 식물, 예를 들어, 담배, 고추, 피망, 토마토, 감자, 가지 ;
석죽과 (Caryophyllaceae) 식물, 예를 들어, 카네이션 ;
파인애플과 (Bromeliaceae) 식물, 예를 들어, 파인애플 ;
어항마름과 (Cabombaceae) 식물, 예를 들어, 순채 ;
파초과 (Musaceae) 식물, 예를 들어, 바나나 ;
파파야과 (Caricaceae) 식물, 예를 들어, 파파야 ;
장미과 (Rosaceae) 식물, 예를 들어, 살구, 딸기, 매화, 모과, 자두, 서양배, 배, 승도복숭아, 장미, 비파, 블랙 라즈베리, 마르멜로, 미니 장미, 복숭아, 사과 ;
메꽃과 (Convolvulaceae) 식물, 예를 들어, 고구마 ;
비름과 (Amaranthaceae) 식물, 예를 들어, 사탕무 ;
포도과 (Vitaceae) 식물, 예를 들어, 포도 ;
참나무과 (Fagaceae) 식물, 예를 들어, 밤 ;
돌나물과 (Crassulaceae) 식물, 예를 들어, 야츠가시라 (토란의 품종) ;
콩과 (Fabaceae) 식물, 예를 들어, 팥, 강낭콩, 완두, 검은팥, 광저기, 잠두콩, 대두, 블랙 빈, 땅콩 ;
운향과 (Rutaceae) 식물, 예를 들어, 탱자나무, 개량 여름귤나무, 오렌지, 금귤, 그레이프 푸르츠, 산초, 영귤, 다이다이, 홍귤나무, 타히티 라임, 여름귤나무, 팔삭귤, 귤, 포멜로, 폰깡 (귤의 일종), 유자, 라임, 레몬 ;
물푸레나무과 (Oleaceae) 식물, 예를 들어, 올리브 ;
종려과 (Arecaceae) 식물, 예를 들어, 야자나무 ;
수레나무과 (Trochodendraceae) 식물, 예를 들어, 자리공 ;
마과 (Dioscoreaceae) 식물, 예를 들어, 마, 참마 ;
백합과 (Liliaceae) 식물, 예를 들어, 아스파라거스, 튤립, 양파, 부추, 마늘, 파, 염교, 실파, 백합 ;
모링가과 (Moringaceae) 식물, 예를 들어, 고추냉이나무 ;
및 이들 식물의 각각의 유전자 재조합이 실시된 품종 등을 들 수 있다.
본 발명의 추가적인 양태는, 본 발명에 의한 살균성 조성물로 처리된 종자에 관한 것이다. 당해 종자는, 식물 병원성 미생물에 의한 식물 병해의 발생을 방지하기 위해서 사용된다. 식물 병원성 미생물이 감염 혹은 부착된 종자 (이하, 오염 종자) 가 건전한 종자에 혼입된 경우, 오염 종자가 식물 병원성 미생물의 감염원이 되어, 근방에서 육성되고 있는 건전한 식물에도 병해가 전파한다. 따라서, 식물 병해 미생물에 대한 살균 활성이 높은 본 발명에 의한 살균성 조성물로 처리된 종자는, 식물 병해의 발생과 건전한 식물에 대한 병원 미생물의 전파를 방지하는 유효한 수단이 된다.
본 발명에 의한 살균성 조성물은, 모든 식물의 종자에 사용할 수 있다. 특히 벼, 밀, 대맥, 호밀, 옥수수, 대두, 면, 감자, 사탕무 등은 재배 규모가 커서, 오염 종자에 의한 병해의 전파에 의한 피해의 확대도 커지기 때문에, 본 발명에 의한 종자는 식물 병원성 미생물에 의한 식물 병해의 발생 방지 수단으로서 유효하다. 더하여, 본 발명에 의한 살균성 조성물을 유전자 재조합 작물의 종자에 처리하는 것도, 식물 병원성 미생물에 의한 식물 병해의 발생 방지 수단으로서 유효하다.
이하에, 본 발명에 의한 살균성 조성물로 처리할 수 있는 유전자 재조합 식물의 예를 들지만, 반드시 이것에 한정되는 것은 아니다. 즉 ;
제초제에 대하여 내성을 나타내도록 형질 전환시킨 식물, 예로는 글리포세이트 내성 식물, 비알라포스 내성 식물, 브로목시닐 내성 식물, 술포닐우레아계 제초제 내성 작물, 이미다졸리논계 제초제 내성 작물, 2,4-D 내성 식물, 디캄바 내성 식물, 이속사플루톨 내성 식물, 메소트리온 내성 식물 등 ;
해충에 대하여 저항성을 나타내도록 형질 전환시킨 식물, 예로는 Bttoxin (바실러스 튜링겐시스의 살충성 독소) 를 생산하도록 형질 전환시킨 식물, 천적 유인 물질을 생산하도록 형질 전환시킨 식물 등 ;
식물 병해에 대하여 저항성을 나타내도록 형질 전환시킨 식물, 예로는 바이러스 저항성 식물, 디펜신을 생산하도록 형질 전환시킨 식물 등 ;
과실의 수확 적기를 확대시키고 보존성을 향상시키도록 형질 전환시킨 식물, 예로는 폴리갈락투로나아제의 생산을 억제하도록 형질 전환시킨 식물, 에틸렌 생합성 효소를 억제하도록 형질 전환시킨 식물 등 ;
수확물의 안전성을 높이도록 형질 전환시킨 식물, 예를 들어, 마이코톡신 분해 효소 생산 식물 등 ;
육종 상 유용해지도록 형질 전환시킨 식물, 예를 들어, 웅성 불임 형질을 나타내도록 형질 전환시킨 식물 등 ;
바이오 에탄올의 원료로서 유용한 형질을 부여한 형질 전환 식물, 예로는 내열성 α-아밀라제 생산 식물 등 ;
환경 스트레스에 대하여 내성을 나타내도록 형질 전환시킨 식물, 예를 들어 RNA 샤페론을 이용한 건조 내성을 나타내는 식물, 저온 내성의 식물에 많이 포함되는 적합 용질인 글리신 베타인을 축적하는 식물, 적합 용질인 프롤린을 축적하는 식물, 보수력이 강한 트레할로스를 축적하고, 건조 내성을 나타내는 식물, 활성 산소를 소거하는 효소를 과잉 생산하는 식물, 무지네산류를 생산함으로써 알칼리 토양에서의 철 결핍에 내성을 나타내는 식물, 무지네산류를 생산함으로써 철 결핍에 내성을 나타내는 식물 등 ;
특정한 기능성 영양소를 생산하도록 형질 전환시킨 식물, 예를 들어 올레산을 과잉으로 생산하는 식물, 스테아리돈산을 과잉으로 산생하는 식물, 리신을 과잉으로 산생하는 식물, 프로 비타민 A 강화 작물, 비타민 E 강화 식물, 안토시아닌을 과잉으로 산생하는 식물, 삼나무의 알레르겐을 산생하여 삼나무 꽃가루 알레르기를 완화하는 효과가 있는 식물 등 ;
을 들 수 있다.
본 발명에 의한 살균성 조성물은, 미생물에 대하여 높은 살균 효과를 나타내는 점에서, 산업 재료를 미생물의 번식으로부터 보호하기 위해서 사용할 수 있다. 여기서 산업 재료의 비한정적인 사례로는, 목재, 플라스틱 자재, 종이 자재, 가죽 자재, 타일, 도기, 시멘트, 페인트, 냉각 윤활제 및 접착제 등을 들 수 있다. 이들 산업 재료에 대한 처리는, 본 발명에 의한 살균성 조성물을 보호 대상물에 분무, 산포, 살분, 스프레이, 확산, 침지, 관주, 살수 (침수), 발포, 도포, 분의, 코팅, 분사, 훈증, 훈연, 연무, 도장 및 혼합함으로써 실시할 수 있다.
본 발명에 의한 살균성 조성물에는, 필요에 따라 농약 제제에 통상적으로 사용되는 첨가물을 함유할 수 있다. 이 첨가물로는, 고체 담체 또는 액체 담체 등의 담체, 계면 활성제, 결합제, 점착 부가제, 증점제, 착색제, 확전제, 동결 방지제, 고결 방지제, 붕괴제, 분해 방지제 등을 들 수 있고, 그 외 필요에 따라, 방부제나 식물편 등을 첨가 성분에 사용해도 된다.
이들 첨가물은 1 종 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다.
상기 첨가 성분에 대하여 설명한다.
고체 담체로는, 예를 들어 석영, 클레이, 카올리나이트, 피로필라이트, 세리사이트, 탤크, 초크, 벤토나이트, 아타풀자이트, 몬모릴로나이트, 산성 백토, 제올라이트, 천연암, 규조토, 방해석, 대리석, 경석, 해포석, 고회석, 등의 천연 광물질류 ; 탄산칼슘, 황산암모늄 또는 그 밖의 암모늄염, 황산나트륨, 염화칼슘, 염화칼륨 등의 무기 염류 ; 전분, 셀룰로오스, 식물 분말 등의 유기 고체 담체 ; 폴리에틸렌, 폴리프로필렌, 폴리염화비닐리덴 등의 플라스틱 담체 ; 그 외, 합성 규산, 합성 규산염, 알루미나, 미세 분말화 실리카, 실리케이트 등을 들 수 있다. 이들은 단독으로 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다.
액체 담체로는, 예를 들어 메탄올, 에탄올, 프로판올, 이소프로판올, 부탄올 등의 1 가 알코올류나, 에틸렌글리콜, 디에틸렌글리콜, 프로필렌글리콜, 헥실렌글리콜, 폴리에틸렌글리콜 ; 폴리프로필렌글리콜글리세린 등의 다가 알코올류로 크게 구별되는 알코올류, 프로필렌계 글리콜에테르 등의 다가 알코올 유도체류 ; 아세톤, 메틸에틸케톤, 메틸이소부틸케톤, 디이소부틸케톤, 시클로헥사논, 이소포론 등의 케톤류 ; 에틸에테르, 디옥산, 셀로솔브, 디프로필에테르, 테트라하이드로푸란 등의 에테르류 ; 노멀파라핀, 나프텐, 이소파라핀, 케로신, 광유 등의 지방족 탄화수소류 ; 벤젠, 톨루엔, 자일렌, 솔벤트나프타, 알킬나프탈렌 등의 방향족 탄화수소류, 디클로로에탄, 클로로포름, 사염화탄소 등의 할로겐화탄화수소류 ; 아세트산에틸, 디이소프로필프탈레이트, 디부틸프탈레이트, 디옥틸프탈레이트, 아디프산디메틸 등의 에스테르류 ; γ-부티로락톤 등의 락톤류 ; 디메틸포름아미드, 디에틸포름아미드, 디메틸아세트아미드, N-알킬피롤리딘 등의 아미드류 ; 아세토니트릴 등의 니트릴류 ; 디메틸술폭시드 등의 황 화합물류 ; 대두유, 유채씨유, 면실유, 피마자유 등의 식물유 ; 물 등을 들 수 있다. 이들은 단독으로 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다.
계면 활성제는 특별히 제한되지 않지만, 바람직하게는 수중에서 겔화하거나, 혹은 팽윤성을 나타내는 것이고, 예를 들어 소르비탄 지방산 에스테르, 폴리옥시에틸렌소르비탄 지방산 에스테르, 자당 지방산 에스테르, 폴리옥시에틸렌 지방산 에스테르, 폴리옥시에틸렌 수지산 에스테르, 폴리옥시에틸렌 지방산 디에스테르, 폴리옥시에틸렌알킬에테르, 폴리옥시에틸렌알킬페놀에테르, 폴리옥시에틸렌디알킬페닐에테르, 폴리옥시에틸렌알킬페놀 포르말린 축합물, 폴리옥시에틸렌폴리옥시프로필렌 블록 폴리머, 알킬폴리옥시에틸렌폴리프로필렌 블록 폴리머 에테르, 폴리옥시에틸렌알킬아민, 폴리옥시에틸렌 지방산 아미드, 폴리옥시에틸렌 지방산 비스페닐에테르, 폴리알킬렌벤질페닐에테르, 폴리옥시알킬렌스티렌페닐에테르, 아세틸렌디올, 폴리옥시알킬렌 부가 아세틸렌디올, 폴리옥시에틸렌에테르형 실리콘, 에스테르형 실리콘, 불소계 계면 활성제, 폴리옥시에틸렌 피마자유, 폴리옥시에틸렌 경화 피마자유 등의 비이온성 계면 활성제 ; 알킬황산염, 폴리옥시에틸렌알킬에테르 황산염, 폴리옥시에틸렌알킬페닐에테르 황산염, 알킬벤젠술폰산염, 리그닌술폰산염, 알킬술포숙신산염, 나프탈렌술폰산염, 알킬나프탈렌술폰산염, 나프탈렌술폰산의 포르말린 축합물의 염, 알킬나프탈렌술폰산의 포르말린 축합물의 염, 지방산염, 폴리카르복실산염, N-메틸-지방산 사르코시네이트, 수지산염, 폴리옥시에틸렌알킬에테르인산염, 폴리옥시에틸렌알킬페닐에테르인산염 등의 아니온성 계면 활성제 ; 라우릴아민염산염, 스테아릴아민염산염, 올레일아민염산염, 스테아릴아민아세트산염, 스테아릴아미노프로필아민염산염, 알킬트리메틸암모늄클로라이드, 알킬디메틸벤잘코늄클로라이드 등의 알킬아민염 등의 카티온성 계면 활성제 ; 및 아미노산형 또는 베타인형 등의 양쪽성 계면 활성제를 들 수 있다. 이들 계면 활성제는 1 종 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다.
또한, 결합제나 점착 부여물로는, 예를 들어 카르복시메틸셀룰로오스나 그 염, 덱스트린, 수용성 전분, 잔탄검, 구아검, 자당, 폴리비닐피롤리돈, 아라비아 고무, 폴리비닐알코올, 폴리비닐아세테이트, 폴리아크릴산나트륨, 평균 분자량 6000 ∼ 20000 의 폴리에틸렌글리콜, 평균 분자량 10 만 ∼ 500 만의 폴리에틸렌옥사이드, 천연 인지질 (예를 들어 세팔린산, 레시틴산 등) 등을 들 수 있다. 이들 결합제나 점착 부여물은 1 종 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다. 증점제로는, 예를 들어 잔탄검, 구아검, 카르복시메틸셀룰로오스, 폴리비닐피롤리돈, 카르복시비닐 폴리머, 아크릴계 폴리머, 전분 유도체, 다당류와 같은 수용성 고분자 ; 및 고순도 벤토나이트, 화이트 카본과 같은 무기 미세 분말 등을 들 수 있다. 이들 증점제는 1 종 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다. 착색제로는, 예를 들어 산화철, 산화티탄, 프루시안 블루와 같은 무기 안료 ; 및 알리자린 염료, 아조 염료, 금속 프탈로시아닌 염료와 같은 유기 염료 등을 들 수 있다. 이들 착색제는 1 종 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다.
확전제로는, 예를 들어 실리콘계 계면 활성제, 셀룰로오스 분말, 덱스트린, 가공 전분, 폴리아미노카르복실산 킬레이트 화합물, 가교 폴리비닐피롤리돈, 말레산과 스티렌산, 메타아크릴산 공중합체, 다가 알코올의 폴리머와 디카르복실산 무수물의 하프 에스테르, 폴리스티렌술폰산의 수용성 염 등을 들 수 있다. 이들 확전제는 1 종 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다. 전착제로는, 예를 들어 디알킬술포숙신산나트륨, 폴리옥시에틸렌알킬에테르, 폴리옥시에틸렌알킬페닐에테르, 폴리옥시에틸렌 지방산 에스테르 등의 다양한 계면 활성제 ; 파라핀, 테르펜, 폴리아미드 수지, 폴리아크릴산염, 폴리옥시에틸렌, 왁스, 폴리비닐알킬에테르, 알킬페놀 포르말린 축합물, 합성 수지 에멀션 등을 들 수 있다. 이들 전착제는 1 종 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다.
동결 방지제로는, 예를 들어 에틸렌글리콜, 디에틸렌글리콜, 프로필렌글리콜, 글리세린 등의 다가 알코올류 등을 들 수 있다. 이들 동결 방지제는 1 종 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다.
고결 방지제로는, 예를 들어 전분, 알긴산, 만노오스, 갈락토오스 등의 다당류, 폴리비닐피롤리돈, 화이트 카본, 에스테르검, 석유 수지 등을 들 수 있다. 이들 고결 방지제는 1 종 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다. 붕괴제로는, 예를 들어 트리폴리인산 소다, 헥산메탈린산 소다, 스테아르산 금속염, 셀룰로오스 분말, 덱스트린, 메타크릴산에스테르의 공중합체, 폴리비닐피롤리돈, 폴리아미노카르복실산 킬레이트 화합물, 술폰화 스티렌·이소부틸렌·무수 말레산 공중합체, 전분·폴리아크릴로니트릴 그래프트 공중합체 등을 들 수 있다. 이들 붕괴제는 1 종 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다.
분해 방지제로는, 예를 들어 제올라이트, 생 석회, 산화마그네슘과 같은 건조제, 페놀계, 아민계, 황계, 인산계 등의 산화 방지제, 살리실산계, 벤조페논계 등의 자외선 흡수제 등을 들 수 있다. 이들 분해 방지제는 1 종 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다.
방부제로는, 예를 들어 소르브산칼륨, 1,2-벤즈티아졸린-3-온 등을 들 수 있다. 이들 방부제는 1 종 사용해도 되고, 또한, 2 종 이상을 조합하여 사용해도 된다.
식물편으로는, 예를 들어 톱밥, 야자 찌꺼기, 옥수수속대, 담배 줄기 등을 들 수 있다.
본 발명의 살균성 조성물 또는 조합물에 있어서, 상기 첨가 성분을 함유시키는 경우, 그 함유 비율에 대해서는, 질량 기준으로, 담체에서는 통상적으로 5 ∼ 95 %, 바람직하게는 20 ∼ 90 %, 계면 활성제에서는 통상적으로 0.1 ∼ 30 %, 바람직하게는 0.5 ∼ 10 %, 그 밖의 첨가물은 0.1 ∼ 30 %, 바람직하게는 0.5 ∼ 10 % 의 범위에서 선택된다.
본 발명의 살균성 조성물은, 예를 들어, 입제, 분립제, 미립제, 액제, 수용제, 유제 (油劑), 유제 (乳劑), 서프제, 에멀션제, 마이크로 에멀션제, 서스포에멀션 제제, EW (emulsion oil in water) 제, 마이크로 캡슐제, 수화제, 현탁제, 플로어블제, 정제, 과립 수화제, 드라이 플로어블제, 수화성 과립제, 에어로졸, 페이스트제, 사이클로덱스트린 제제, 점보제, 팩제, 수용성 포장 제제, 분말제, 훈연제, 훈증제 등과 같은 농원예용 살균제에 적합한 약제로서 사용할 수 있다.
이와 같은 양태는, 식 [1] 에서 선택되는 적어도 1 종의 화합물과, 구성 성분 (b) 에서 선택되는 적어도 1 종의 적당한 고체 또는 액체의 담체류, 및 원하는 바에 따라, 유효 성분의 분산성이나, 다른 성질의 개선을 위해서 적당한 보조제 (예를 들어, 계면 활성제, 용제, 안정제) 와 함께 혼합하는 통상적인 방법에 의해 얻을 수 있다. 사용에 있어서는 적당한 농도로 희석하여 산포하거나 또는 직접 시용한다.
본 발명에 의한 살균성 조성물은, 살충제, 살진드기제, 살선충제, 살달팽이제, 섭식 저해제, 제초제, 살조제, 살진드기제, 살선충제, 생물 농약, 페로몬제, 천연 살균제, 천연 살충제와 같은 브리티시 크롭 프로텍션 카운실 발행의 페스티사이드 매뉴얼 (2013년), 일본 전국 농업 협동 조합 연합회 발행의 쿠미아이 농약 총람 (2014년) 및 일본 전국 농촌 교육 협회 발행의 SHIBUYA INDEX (제17판) 등에서 알려져 있는 성분을 공동 성분으로서 포함함으로써, 더욱 넓은 범위의 농업 보호를 가져오는 다구성 성분 유해 생물 방제제를 형성하는 것이 가능하다. 하기에 공동 성분의 예를 나타내지만, 이들에 한정되는 것은 아니다.
살충제, 살진드기제, 살선충제, 살달팽이제 및 섭식 저해제의 예로는, 1,2-디클로로프로판 (1,2-dichloropropane), 1,3-디클로로프로펜 (1,3-dichloropropene), 아바멕틴 (abamectin), 아세페이트 (acephate), 아세퀴노실 (acequinocyl), 아세타미프리드 (acetamiprid), 아세티온 (acethion), 아세토포스 (acetophos), 아세토프롤 (acetoprole), 아크리나트린 (acrinathrin), 아크릴로니트릴 (acrylonitrile), 아피도피로펜 (afidopyropen), 알라니카르브 (alanycarb), 알독시카르브 (aldoxycarb), 알레트린 (allethrin), 알리신 (allicin), 알로사미딘 (allosamidin), 알릭시카르브 (allyxycarb), 알파사이퍼메트린 (alpha-cypermethrin), 알파엔도술판 (alpha-endosulfan), 아미디티온 (amidithion), 아미도플루메트 (amidoflumet), 아미노카르브 (aminocarb), 아미톤 (amiton), 아미트라즈 (amitraz), 아나바신 (anabasine), 아라마이트 (aramite), 아티다티온 (athidathion), 아자디락틴 (azadirachtin), 아자메티포스 (azamethiphos), 아진포스에틸 (azinphos-ethyl), 아진포스메틸 (azinphos-methyl), 아조벤젠 (azobenzene), 아조시클로틴 (azocyclotin), 아조토에이트 (azothoate), 바실러스 튜링겐시스 쿠르스타키계 (Bacillus thuringiensis kurstaki), 바실러스 튜링겐시스 부이부이계 (Bacillus thuringiensis Buibui), 바실러스 튜링겐시스 아이자와이계 (Bacillus thuringiensis aisawai), 육불화규산바륨 (barium hexafluorosilicate), 바르트린 (barthrin), 벤클로티아즈 (benclothiaz), 벤디오카르브 (bendiocarb), 벤푸라카르브 (benfuracarb), 베녹사포스 (benoxafos), 벤술탑 (bensultap), 벤족시메이트 (benzoximate), 벤조산벤질 (benzyl benzoate), 베타시플루트린 (beta-cyfluthrin), 베타사이퍼메트린 (beta-cypermethrin), 비페나제이트 (bifenazate), 비펜트린 (bifenthrin), bifujunzhi, 비나파크릴 (binapacryl), 비오알레트린 (bioallethrin), 비오메타에트린 (bioethanomethrin), 비오퍼메트린 (biopermethrin), 비스트리플루론 (bistrifluron), 보락스 (borax), 붕산 (boric acid), 브로펜발레레이트 (brofenvalerate), 브로플라닐리드 (broflanilid), 브로플루트리네이트 (brofluthrinate), 브로메트린 (bromethrin), 브롬펜빈포스 (bromfenvinfos), 브로모아세타미드 (bromoacetamide), 브로모시클렌 (bromocyclen), 브로모 DDT (bromo-DDT), 브로모포스 (bromophos), 브로모포스에틸 (bromophos-ethyl), 브로모프로필레이트 (bromopropylate), 부펜카르브 (bufencarb), 부프로페진 (buprofezin), 부타카르브 (butacarb), 부타티오포스 (butathiofos), 부테트린 (butethrin), 부토카르복심 (butocarboxim), 부토네이트 (butonate), 부톡시카르복심 (butoxycarboxim), 카두사포스 (cadusafos), 다황산칼슘 (calcium polysulfide), 칼빈포스 (calvinphos), 캄페클로르 (camphechlor), 카르바놀레이트 (carbanolate), 카르바릴 (carbaryl), 카르보푸란 (carbofuran), 이황화탄소 (carbon disulfide), 사염화탄소 (carbon tetrachloride), 황화카르보닐 (carbonyl sulfide), 카르보페노티온 (carbophenothion), 카르보술판 (carbosulfan), 카르탑 (cartap), 카르바크롤 (carvacrol), 키노메티오나트 (chinomethionat), 클로라민포스포러스 (chloramine phosphorus), 클로란트라닐리프롤 (chlorantraniliprole), 클로르벤시드 (chlorbenside), 클로르벤주론 (chlorbenzuron), 클로르비시클렌 (chlorbicyclen), 클로르데콘 (chlordecone), 클로렘펜트린 (chlorempenthrin), 클로레톡시포스 (chlorethoxyfos), 클로르페나피르 (chlorfenapyr), 클로르페네톨 (chlorfenethol), 클로르펜손 (chlorfenson), 클로르펜술피드 (chlorfensulphide), 클로르펜빈포스 (chlorfenvinphos), 클로르플루아주론 (chlorfluazuron), 클로르메포스 (chlormephos), 클로로포름 (chloroform), 클로로메부포름 (chloromebuform), 클로로메티우론 (chloromethiuron), 클로로피크린 (chloropicrin), 클로로프랄레트린 (chloroprallethrin), 클로로프로필레이트 (chloropropylate), 클로르폭심 (chlorphoxim), 클로르프라조포스 (chlorprazophos), 클로르피리포스 (chlorpyrifos), 클로르피리포스메틸 (chlorpyrifos-methyl), 클로르티오포스 (chlorthiophos), 크로마페노지드 (chromafenozide), 시네린 I (cinerin I), 시네린 II (cinerin II), 시네린 복합체 (cinerins), 시스메트린 (cismethrin), 클렌피린 (clenpirin), 클로에토카르브 (cloethocarb), 클로펜테진 (clofentezine), 클로산텔 (closantel), 클로티아니딘 (clothianidin), 콜로포네이트 (colophonate), 나프텐산동 (copper naphthenate), 올레산동 (copper oleate), 황산동 (copper sulfate), 쿠마포스 (coumaphos), 쿠미토에이트 (coumithoate), CPMC, 크로타미톤 (crotamiton), 크로톡시포스 (crotoxyphos), 크루포메이트 (crufomate), 크리올라이트 (cryolite), 시아노펜포스 (cyanofenphos), 시아노겐 (cyanogen), 시아노포스 (cyanophos), 시안토에이트 (cyanthoate), 시안트라닐리프롤 (cyantraniliprole), 시클라닐리프롤 (cyclaniliprole), 시클레트린 (cyclethrin), 시클로프레이트 (cycloprate), 시클로프로트린 (cycloprothrin), 시에노피라펜 (cyenopyrafen), 시플루메토펜 (cyflumetofen), 시플루트린 (cyfluthrin), 시할로디아미드 (cyhalodiamide), 시할로트린 (cyhalothrin), 시헥사틴 (cyhexatin), 시미아졸 (cymiazole), 사이퍼메트린 (cypermethrin), 시로마진 (cyromazine), 시티오에이트 (cythioate), dayoutong, 다조메트 (dazomet), DBCP, DCIP, 데카르보푸란 (decarbofuran), 델타메트린 (deltamethrin), 데메피온 (demephion), 데메피온 O (demephion-O), 데메피온 S (demephion-S), 데메톤 (demeton), 데메톤메틸 (demeton-methyl), 데메톤 O (demeton-O), 데메톤 O 메틸 (demeton-O-methyl), 데메톤 S (demeton-S), 데메톤 S 메틸 (demeton-S-methyl), 데메톤 S 메틸술폰 (demeton-S-methylsulphon), d-fanshiluquebingjuzhi, 디아펜티우론 (diafenthiuron), 디알리포스 (dialifos), 디아미다포스 (diamidafos), 규조토 (diatomaceous earth), 디아지논 (diazinon), 디캡톤 (dicapthon), 디클로펜티온 (dichlofenthion), 디클로플루아니드 (dichlofluanid), 디클로르벤주론 (dichlorbenzuron), 디클로르보스 (dichlorvos), 디클로로메조티아즈 (dicloromezotiaz), 디코폴 (dicofol), 디크레실 (dicresyl), 디크로토포스 (dicrotophos), 디시클라닐 (dicyclanil), 디에노클로르 (dienochlor), 디플로비다진 (diflovidazin), 디플루벤주론 (diflubenzuron), 딜로르 (dilor), 디메플루트린 (dimefluthrin), 디메폭스 (dimefox), 디메탄 (dimetan), 디메타카르브 (dimethacarb), 디메토에이트 (dimethoate), 디메트린 (dimethrin), 디메틸빈포스 (dimethylvinphos), 디메틸란 (dimetilan), 디넥스 (dinex), 디노부톤 (dinobuton), 디노캅 (dinocap), 디노캅 4 (dinocap-4), 디노캅 6 (dinocap-6), 디녹톤 (dinocton), 디노펜톤 (dinopenton), 디노프롭 (dinoprop), 디노삼 (dinosam), 디노술폰 (dinosulfon), 디노테푸란 (dinotefuran), 디노테르본 (dinoterbon), 디오페놀란 (diofenolan), 디옥사벤조포스 (dioxabenzofos), 디옥사카르브 (dioxacarb), 디옥사티온 (dioxathion), 디페닐술폰 (diphenylsulfone), 디피메티트론 (dipymetitrone), 디술피람 (disulfiram), 디술포톤 (disulfoton), 디티크로포스 (dithicrofos), 디티오에테르 (dithioether), d-리모넨 (d-limonene), DNOC, 도페나핀 (dofenapyn), 도라멕틴 (doramectin), 에크디스테론 (ecdysterone), 에마멕틴 (emamectin), EMPC, 엠펜트린 (empenthrin), 엔도티온 (endothion), 엔드린 (endrin), EPN, 에포페노난 (epofenonane), 에프리노멕틴 (eprinomectin), 입실론메토플루트린 (epsilon-metofluthrin), 입실론몸플루오로트린 (epsilon-momfluorothrin), 에스데팔레트린 (esdepallethrine), 에스펜발레레이트 (esfenvalerate), 에타포스 (etaphos), 에티오펜카르브 (ethiofencarb), 에티온 (ethion), 에티프롤 (ethiprole), 에토에이트메틸 (ethoate-methyl), 에토프로포스 (ethoprophos), 포름산에틸 (ethyl formate), 에틸 DDD (ethyl-DDD), 이브롬화에틸렌 (ethylene dibromide), 이염화에틸렌 (ethylene dichloride), 에토펜프록스 (etofenprox), 에톡사졸 (etoxazole), 에트림포스 (etrimfos), EXD, 팜푸르 (famphur), 페나미포스 (fenamiphos), 페나자플로르 (fenazaflor), 페나자퀸 (fenazaquin), 산화펜부타주석 (fenbutatin oxide), 펜클로르포스 (fenchlorphos), 페네타카르브 (fenethacarb), 펜플루트린 (fenfluthrin), 페니트로티온 (fenitrothion), 페노부카르브 (fenobucarb), 페노티오카르브 (fenothiocarb), 페녹사크림 (fenoxacrim), 페녹시카르브 (fenoxycarb), 펜피리트린 (fenpirithrin), 펜프로파트린 (fenpropathrin), 펜피록시메이트 (fenpyroximate), 펜손 (fenson), 펜술포티온 (fensulfothion), 펜티온 (fenthion), 펜티온에틸 (fenthion-ethyl), 펜트리파닐 (fentrifanil), 펜발레레이트 (fenvalerate), 인산 제 2 철 (ferric phosphate), 피프로닐 (fipronil), 피프로닐 (fipronil), 플로메토퀸 (flometoquin), 플로니카미드 (flonicamid), 플루아크리피림 (fluacrypyrim), 플루아자인돌리진 (fluazaindolizine), 플루아주론 (fluazuron), 플루벤디아미드 (flubendiamide), 플루벤지민 (flubenzimine), 플루코푸론 (flucofuron), 플루시클록수론 (flucycloxuron), 플루시클록수론 (flucycloxuron), 플루시트리네이트 (flucythrinate), 플루에네틸 (fluenetil), 플루엔술폰 (fluensulfone), 플루페네림 (flufenerim), 플루페녹수론 (flufenoxuron), 플루페녹시스트로빈 (flufenoxystrobin), 플루펜프록스 (flufenprox), 플루피프롤 (flufiprole), 플루헥사폰 (fluhexafon), 플루메트린 (flumethrin), 플루오르벤시드 (fluorbenside), 플루피라디푸론 (flupyradifurone), 플루랄라네르 (fluralaner), 플루르술라미드 (flursulamid), 플루발리네이트 (fluvalinate), 플룩사메타미드 (fluxametamide), 포노포스 (fonofos), 포르메타네이트 (formetanate), 염산포르메타네이트 (formetanate hydrochloride), 포르모티온 (formothion), 포름파라네이트 (formparanate), 포스메틸란 (fosmethilan), 포스피레이트 (fospirate), 포스티아제이트 (fosthiazate), 포스티에탄 (fosthietan), 푸라메트린 (furamethrin), 푸란테부페노지드 (furantebufenozide), 푸라티오카르브 (furathiocarb), 푸레트린 (furethrin), 푸르푸랄 (furfural), 감마시할로트린 (gamma-cyhalothrin), 감마 HCH (gamma-HCH), 게니트 (genit), 구아자틴 (guazatine), 할펜프록스 (halfenprox), 할로페노지드 (halofenozide), HCH, HEOD, 헵타플루트린 (heptafluthrin), 헵테노포스 (heptenophos), 헤테로포스 (heterophos), 헥사클로로펜 (hexachlorophene), 헥사플루무론 (hexaflumuron), 헥시티아족스 (hexythiazox), HHDN, 히드라메틸논 (hydramethylnon), 하이드로프렌 (hydroprene), 히퀸카르브 (hyquincarb), 이미시아포스 (imicyafos), 이미다클로프리드 (imidacloprid), 이미다클로티즈 (imidaclothiz), 이미프로트린 (imiprothrin), 인독사카르브 (indoxacarb), IPSP, 이사미도포스 (isamidofos), 이사조포스 (isazofos), 이소벤잔 (isobenzan), 이소카르보포스 (isocarbophos), 이소드린 (isodrin), 이소펜포스 (isofenphos), 이소펜포스메틸 (isofenphos-methyl), 이솔란 (isolan), 이소프로카르브 (isoprocarb), 이소프로티올란 (isoprothiolane), 이소티오에이트 (isothioate), 이속사티온 (isoxathion), 이베르멕틴 (ivermectin), 자포트린스 (japothrins), 자스몰린 I (jasmolin I), 자스몰린 II (jasmolin II), jiahuangchongzong, 조드펜포스 (jodfenphos), 유약 호르몬 I (juvenile hormone I), 유약 호르몬 II (juvenile hormone II), 유약 호르몬 III (juvenile hormone III), 카데트린 (kadethrin), 캅파비펜트린 (kappa-bifenthrin), 캅파테플루트린 (kappa-tefluthrin), 켈레반 (kelevan), 키노프렌 (kinoprene), 람다시할로트린 (lambda-cyhalothrin), 레피멕틴 (lepimectin), 렙토포스 (leptophos), 리림포스 (lirimfos), 루페누론 (lufenuron), 리티다티온 (lythidathion), 말라티온 (malathion), 말로노벤 (malonoben), 말토덱스트린 (maltodextrin), 마트린 (matrine), 마지독스 (mazidox), 메카르밤 (mecarbam), 메카르폰 (mecarphon), 메디메포름 (medimeform), 메나존 (menazon), 메페르플루트린 (meperfluthrin), 메포스폴란 (mephosfolan), 메술펜 (mesulfen), 메술펜포스 (mesulfenfos), 메타플루미존 (metaflumizone), 메트알데히드 (metaldehyde), 메탐 (metam), 메타크리포스 (methacrifos), 메티다티온 (methidathion), 메티오카르브 (methiocarb), 메토크로토포스 (methocrotophos), 메토밀 (methomyl), 메토프렌 (methoprene), 메토트린 (methothrin), 메톡시클로르 (methoxychlor), 메톡시페노지드 (methoxyfenozide), 요오드화메틸 (methyl iodide), 이소티오시안산메틸 (methyl isothiocyanate), 메틸아세토포스 (methylacetophos), 메틸클로로포름 (methylchloroform), 염화메틸렌 (methylene chloride), 메토플루트린 (metofluthrin), 메톨카르브 (metolcarb), 메톡사디아존 (metoxadiazone), 메빈포스 (mevinphos), 멕사카르베이트 (mexacarbate), 밀베멕틴 (milbemectin), 밀베마이신옥심 (milbemycinoxime), 미파폭스 (mipafox), 미렉스 (mirex), MNAF, 몸플루오로트린 (momfluorothrin), 모르포티온 (morphothion), 목시덱틴 (moxidectin), 나프탈로포스 (naftalofos), 날레드 (naled), 나프탈렌 (naphthalene), 니클로사미드 (niclosamide), 니코틴 (nicotine), 니플루리디드 (nifluridide), 니코마이신 복합체 (nikkomycins), 니텐피람 (nitenpyram), 니티아진 (nithiazine), 니트릴라카르브 (nitrilacarb), 노르니코틴 (nornicotine), 노발루론 (novaluron), 노비플루무론 (noviflumuron), 오메토에이트 (omethoate), 옥사밀 (oxamyl), 옥시데메톤메틸 (oxydemeton-methyl), 옥시데프로포스 (oxydeprofos), 옥시디술포톤 (oxydisulfoton), 옥시마트린 (oxymatrine), paichongding, 파라디클로로벤젠 (para-dichlorobenzene), 펜플루론 (penfluron), 펜타클로로페놀 (pentachlorophenol), 펜트메트린 (pentmethrin), 페르메트린 (permethrin), 펜캡톤 (phenkapton), 페노트린 (phenothrin), 펜프록시드 (phenproxide), 펜토에이트 (phenthoate), 포레이트 (phorate), 포살론 (phosalone), 포스폴란 (phosfolan), 포스폴란메틸 (phosfolan-methyl), 포스글리신 (phosglycin), 포스메트 (phosmet), 포스니클로르 (phosnichlor), 포스핀 (phosphine), 포스포카르브 (phosphocarb), 포스틴 (phostin), 폭심 (phoxim), 폭심메틸 (phoxim-methyl), 피리메타포스 (pirimetaphos), 피리미노카르브 (pirimicarb), 피리미옥시포스 (pirimioxyphos), 피리미포스에틸 (pirimiphos-ethyl), 피리미포스메틸 (pirimiphos-methyl), 플리페네이트 (plifenate), 폴리티알란 (polythialan), 티오시안산칼륨 (potassium thiocyanate), 프랄레트린 (prallethrin), 프레코센 I (precocene I), 프레코센 II (precocene II), 프레코센 III (precocene III), 프리미도포스 (primidophos), 프로클로놀 (proclonol), 프로페노포스 (profenofos), 프로플루트린 (profluthrin), 프로마실 (promacyl), 프로메카르브 (promecarb), 프로파포스 (propaphos), 프로파르기트 (propargite), 프로파트린 (proparthrin), 프로페탐포스 (propetamphos), 프로폭수르 (propoxur), 프로폭수르 (propoxur), 프로티다티온 (prothidathion), 프로티오포스 (prothiofos), 프로토에이트 (prothoate), 프로트리펜부트 (protrifenbute), 피플루부미드 (pyflubumide), 피메트로진 (pymetrozine), 피라클로포스 (pyraclofos), 피라플루프롤 (pyrafluprole), 피라마트 (pyramat), 피라조포스 (pyrazophos), 피라조티온 (pyrazothion), 피레스메트린 (pyresmethrin), 피레트린 I (pyrethrin I), 피레트린 II (pyrethrin II), 피레트린 (pyrethrins), 피리다벤 (pyridaben), 피리달릴 (pyridalyl), 피리다펜티온 (pyridaphenthion), 피리플루퀴나존 (pyrifluquinazon), 피리미디펜 (pyrimidifen), 피리미노스트로빈 (pyriminostrobin), 피리미테이트 (pyrimitate), 피리프롤 (pyriprole), 피리프록시펜 (pyriproxyfen), 피롤란 (pyrolan), 콰시아 (quassia), 퀴날포스 (quinalphos), 퀴날포스메틸 (quinalphos-methyl), 퀴노티온 (quinothion), 퀸티오포스 (quintiofos), 라폭사니드 (rafoxanide), 레스메트린 (resmethrin), 로도자포닌 III (rhodojaponin-III), 로테논 (rotenone), 리아니아 (ryania), 사바딜라 (sabadilla), sanguinarine, 슈라단 (schradan), 셀라멕틴 (selamectin), 세미아미트라즈 (semiamitraz), 염화세미아미트라즈 (semiamitraz chloride), 실라플루오펜 (silafluofen), 실리카 겔 (silica gel), 불화나트륨 (sodium fluoride), 헥사플루오로규산나트륨 (sodium hexafluorosilicate), 클로로페놀나트륨 (sodium pentachlorophenoxide), 테트라티오탄산나트륨 (sodium tetrathiocarbonate), 티오시안산나트륨 (sodium thiocyanate), 소파미드 (sophamide), 스피네토람 (spinetoram), 스피노사드 (spinosad), 스피로디클로펜 (spirodiclofen), 스피로메시펜 (spiromesifen), 스피로테트라마트 (spirotetramat), 술코푸론 (sulcofuron), 술코푸론나트륨염 (sulcofuron-sodium), 술피람 (sulfiram), 술플루라미드 (sulfluramid), 술포텝 (sulfotep), 술폭사플로르 (sulfoxaflor), 술폭심 (sulfoxime), 황 (sulfur), 불화술푸릴 (sulfuryl fluoride), 술프로포스 (sulprofos), 타우플루발리네이트 (tau-fluvalinate), 타짐카르브 (tazimcarb), TDE, 테부페노지드 (tebufenozide), 테부펜피라드 (tebufenpyrad), 테부피림포스 (tebupirimfos), 테플루벤주론 (teflubenzuron), 테플루트린 (tefluthrin), 테메포스 (temephos), TEPP, 테랄레트린 (terallethrin), 테부포스 (terbufos), 테트라클로로에탄 (tetrachloroethane), 테트라클로로빈포스 (tetrachlorvinphos), 테트라디폰 (tetradifon), 테트라메트린 (tetramethrin), 테트라메틸플루트린 (tetramethylfluthrin), 테트라낙틴 (tetranactin), 테트라닐리프롤 (tetraniliprole), 테트라술 (tetrasul), 테트라사이퍼메트린 (theta-cypermethrin), 티아클로프리드 (thiacloprid), 티아메톡삼 (thiamethoxam), 티아프로닐 (thiapronil), 트리크로포스 (thicrofos), 티오카르복심 (thiocarboxime), 티오시클람 (thiocyclam), 티오디카르브 (thiodicarb), 티오파녹스 (thiofanox), 티오플루옥시메이트 (thiofluoximate), 티오메톤 (thiometon), 티오나진 (thionazin), 티오퀴녹스 (thioquinox), 티오술탑 (thiosultap), 티오술탑나트륨염 (thiosultap-sodium), 티옥사자펜 (tioxazafen), 티르파트 (tirpate), 톨펜피라드 (tolfenpyrad), 트랄로시트린 (tralocythrin), 트랄로메트린 (tralomethrin), 트랄로피릴 (tralopyril), 트랜스퍼메트린 (transpermethrin), 트리아라텐 (triarathene), 트리아자메이트 (triazamate), 트리아조포스 (triazophos), 트리클로르폰 (trichlorfon), 트리클로르메타포스 3 (trichlormetaphos-3), 트리클로로나트 (trichloronat), 트리펜모르프 (trifenmorph), 트리페노포스 (trifenofos), 트리플루메조피림 (triflumezopyrim), 트리플루무론 (triflumuron), 트리메타카르브 (trimethacarb), 트리프렌 (triprene), 트립톨리드 (triptolide), 발레레이트 (valerate), 바미도티온 (vamidothion), 바닐리프롤 (vaniliprole), xiaochongliulin, XMC, 자일레놀류 (xylenols), 자일릴카르브 (xylylcarb), yishijing, 제타사이퍼메트린 (zeta-cypermethrin), 졸라프로포스 (zolaprofos), 알파엑다이손 (α-ecdysone), AKD-1193, DKN-2601, IKI-3106, KUI-1103, KUI-1301, KYIF-1402, ME5382, MIE-1209, MIE-1405, MSI-1301, MSI-1302, NA-89, NC-515, ZDI-2501, ZDI-2502 등을 들 수 있다.
제초제 및 살조제의 예로는, 2,3,6-TBA, 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, 아세토클로르 (acetochlor), 아시플루오르펜 (acifluorfen), 아클로니펜 (aclonifen), 아크롤레인 (acrolein), 알리도클로르 (allidochlor), 알록시딤 (alloxydim), 알릴알코올 (allylalcohol), 알로락 (alorac), 아메트리디온 (ametridione), 아메트린 (ametryn), 아미부진 (amibuzin), 아미카르바존 (amicarbazone), 아미도술푸론 (amidosulfuron), 아미노시클로피라클로르 (aminocyclopyrachlor), 아미노피랄리드 (aminopyralid), 아미프로포스-메틸 (amiprofos-methyl), 아미프로포스 (amiprophos), 아미트롤 (amitrole), 술팜산암모늄 (ammonium sulfamate), 아닐로포스 (anilofos), 아니수론 (anisuron), 아술람 (asulam), 아트라톤 (atraton), 아트라진 (atrazine), 아자페니딘 (azafenidin), 아짐술푸론 (azimsulfuron), 아지프로트린 (aziprotryne), 바반 (barban), BCPC, 베플루부타미드 (beflubutamid), 베나졸린 (benazolin), 벤카르바존 (bencarbazone), 벤플루랄린 (benfluralin), 벤푸레세이트 (benfuresate), 벤술푸론 (bensulfuron), 벤술리드 (bensulide), 벤타존 (bentazone), 벤트라닐 (bentranil), 벤자독스 (benzadox), 염화벤잘코늄 (benzalkonium chloride), 벤즈펜디존 (benzfendizone), 벤지프람 (benzipram), 벤조비시클론 (benzobicyclon), 벤조페납 (benzofenap), 벤조플루오르 (benzofluor), 벤조일프롭 (benzoylprop), 벤즈티아주론 (benzthiazuron), 베톡사진 (bethoxazin), 비시클로피론 (bicyclopyrone), 비페녹스 (bifenox), 빌라나포스 (bilanafos), 비스피리백 (bispyribac), 붕사 (borax), 브로마실 (bromacil), 브로모보닐 (bromobonil), 브로모부티드 (bromobutide), 브로모페녹심 (bromofenoxim), 브로목시닐 (bromoxynil), 브롬피라존 (brompyrazon), 부타클로르 (butachlor), 부타페나실 (butafenacil), 부타미포스 (butamifos), 부테나클로르 (butenachlor), 부티아졸 (buthidazole), 부티우론 (buthiuron), 부트랄린 (butralin), 부트록시딤 (butroxydim), 부투론 (buturon), 부틸레이트 (butylate), 카코딜산 (cacodylic acid), 카펜스트롤 (cafenstrole), 염소산칼슘 (calcium chlorate), 칼슘시아나미드 (calcium cyanamide), 캄벤디클로르 (cambendichlor), 카르바술람 (carbasulam), 카르베타미드 (carbetamide), 카르복사졸 (carboxazole), 카르펜트라존 (carfentrazone), CDEA, CEPC, 클로메톡시펜 (chlomethoxyfen), 클로람벤 (chloramben), 클로라노크릴 (chloranocryl), 클로라지폽 (chlorazifop), 클로라진 (chlorazine), 클로르브로무론 (chlorbromuron), 클로르부팜 (chlorbufam), 클로레투론 (chloreturon), 클로르페낙 (chlorfenac), 클로르펜프롭 (chlorfenprop), 클로르플루라졸 (chlorflurazole), 클로르플루레놀 (chlorflurenol), 클로리다존 (chloridazon), 클로리무론 (chlorimuron), 클로르니딘 (chlornidine), 클로르니트로펜 (chlornitrofen), 클로로폰 (chloropon), 클로로톨루론 (chlorotoluron), 클로록수론 (chloroxuron), 클로록시닐 (chloroxynil), 클로르프로카르브 (chlorprocarb), 클로르프로팜 (chlorpropham), 클로르술푸론 (chlorsulfuron), 클로르탈 (chlorthal), 클로르티아미드 (chlorthiamid), 시니돈에틸 (cinidon-ethyl), 신메틸린 (cinmethylin), 시노술푸론 (cinosulfuron), 시사닐리드 (cisanilide), 클라시포스 (clacyfos), 클레토딤 (clethodim), 클리오디네이트 (cliodinate), 클로디나폽 (clodinafop), 클로폽 (clofop), 클로마존 (clomazone), 클로메프롭 (clomeprop), 클로프롭 (cloprop), 클로프록시딤 (cloproxydim), 클로피랄리드 (clopyralid), 클로란술람 (cloransulam), CMA, 황산동 (copper sulfate), CPMF, CPPC, 크레다진 (credazine), 크레졸 (cresol), 쿠밀루론 (cumyluron), 시아나미드 (cyanamide), 시아나트린 (cyanatryn), 시아나진 (cyanazine), 시아노겐 (cyanogen), 시부트린 (cybutryne), 시클로에이트 (cycloate), 시클로피리모레이트 (cyclopyrimorate), 시클로술파무론 (cyclosulfamuron), 시클록시딤 (cycloxydim), 시클루론 (cycluron), 시할로폽 (cyhalofop), 사이퍼콰트 (cyperquat), 시프라진 (cyprazine), 시프라졸 (cyprazole), 시프로미드 (cypromid), 다이무론 (daimuron), 달라폰 (dalapon), 다조메트 (dazomet), 델라클로르 (delachlor), 데스메디팜 (desmedipham), 데스메트린 (desmetryn), 디알레이트 (di-allate), 디캄바 (dicamba), 디클로베닐 (dichlobenil), 디클론 (dichlone), 디클로랄우레아 (dichloralurea), 디클로메이트 (dichlormate), 디클로로펜 (dichlorophen), 디클로르프롭 (dichlorprop), 디클로르프롭-P (dichlorprop-P), 디클로폽 (diclofop), 디클로술람 (diclosulam), 디에탐콰트 (diethamquat), 디에타틸에틸 (diethatyl), 디페노펜텐 (difenopenten), 디페녹수론 (difenoxuron), 디펜조콰트 (difenzoquat), 디플루페니칸 (diflufenican), 디플루펜조피르 (diflufenzopyr), 디메푸론 (dimefuron), 디메피페레이트 (dimepiperate), 디메타클로르 (dimethachlor), 디메타메트린 (dimethametryn), 디메테나미드 (dimethenamid), 디메테나미드-P (dimethenamid-P), 디멕사노 (dimexano), 디미다존 (dimidazon), 디니트라민 (dinitramine), 디노페네이트 (dinofenate), 디노프롭 (dinoprop), 디노삼 (dinosam), 디노테르브 (dinoterb), 디페나미드 (diphenamid), 디프로팔린 (dipropalin), 디프로페트린 (dipropetryn), 디콰트 (diquat), 디술 (disul), 디티오에테르 (dithioether), 디티오피르 (dithiopyr), 디우론 (diuron), DMPA, DNOC, DSMA, EBEP, 에글리나진 (eglinazine), 엔도탈 (endothal), 에프로나즈 (epronaz), EPTC, 에르본 (erbon), erlujixiancaoan, 에스프로카르브 (esprocarb), 에타클로르 (ethachlor), 에탈플루랄린 (ethalfluralin), 에타메트술푸론 (ethametsulfuron), 에타프로클로르 (ethaprochlor), 에티디무론 (ethidimuron), 에티올레이트 (ethiolate), 에티오진 (ethiozin), 에토푸메세이트 (ethofumesate), 에톡시펜 (ethoxyfen), 에톡시술푸론 (ethoxysulfuron), 에티노펜 (etinofen), 에트니프로미드 (etnipromid), 에토벤자니드 (etobenzanid), EXD, 페나술람 (fenasulam), 페노프롭 (fenoprop), 페녹사프롭 (fenoxaprop), 페녹사프롭-P (fenoxaprop-P), 페녹사술폰 (fenoxasulfone), 펜퀴노트리온 (fenquinotrione), 펜테라콜 (fenteracol), 펜티아프롭 (fenthiaprop), 주석 (fentin), 펜트라자미드 (fentrazamide), 페누론 (fenuron), 황산철 (ferrous sulfate), 플람프롭 (flamprop), 플람프롭-M (flamprop-M), 플라자술푸론 (flazasulfuron), 플로라술람 (florasulam), 플루아지폽 (fluazifop), 플루아지폽-P (fluazifop-P), 플루아졸레이트 (fluazolate), 플루카르바존 (flucarbazone), 플루세토술푸론 (flucetosulfuron), 플루클로랄린 (fluchloralin), 플루페나세트 (flufenacet), 플루페니칸 (flufenican), 플루펜피르 (flufenpyr), 플루메트술람 (flumetsulam), 플루메진 (flumezin), 플루마이클로락 (flumiclorac), 플루미옥사진 (flumioxazin), 플루미프로핀 (flumipropyn), 플루오메투론 (fluometuron), 플루오로디펜 (fluorodifen), 플루오로글리코펜 (fluoroglycofen), 플루오로미딘 (fluoromidine), 플루오로니트로펜 (fluoronitrofen), 플루오티우론 (fluothiuron), 플루폭삼 (flupoxam), 플루프로파실 (flupropacil), 플루프로파네이트 (flupropanate), 플루피르술푸론 (flupyrsulfuron), 플루리돈 (fluridone), 플루로클로리돈 (flurochloridone), 플루록시피르 (fluroxypyr), 플루르타몬 (flurtamone), 플루티아세트 (fluthiacet), 포메사펜 (fomesafen), 포람술푸론 (foramsulfuron), 포사민 (fosamine), 푸카오징 (fucaojing), 푸카오미 (fucaomi), 푸나이헤카올링 (funaihecaoling), 푸릴옥시펜 (furyloxyfen), 글루포시네이트 (glufosinate), 글루포시네이트-P (glufosinate-P), 글리포세이트 (glyphosate), 할라욱시펜 (halauxifen), 할로사펜 (halosafen), 할로술푸론 (halosulfuron), 할록시딘 (haloxydine), 할록시폽 (haloxyfop), 할록시폽-P (haloxyfop-P), 하비마이신 (herbimycin), 헥사클로로아세톤 (hexachloroacetone), 헥사플루레이트 (hexaflurate), 헥사지논 (hexazinone), 후안카이오 (huancaiwo), 후앙카올링 (huangcaoling), 소석회 (hydrated lime), 이마자메타벤즈 (imazamethabenz), 이마자목스 (imazamox), 이마자픽 (imazapic), 이마자피르 (imazapyr), 이마자퀸 (imazaquin), 이마제타피르 (imazethapyr), 이마조술푸론 (imazosulfuron), 인다노판 (indanofan), 인다지플람 (indaziflam), 이오도보닐 (iodobonil), 이오도술푸론메틸 (iodosulfuron), 이오펜술푸론 (iofensulfuron), 이옥시닐 (ioxynil), 이파진 (ipazine), 입펜카르바존 (ipfencarbazone), 이프리미담 (iprymidam), 이소카르바미드 (isocarbamid), 이소실 (isocil), 이소메티오진 (isomethiozin), 이소노루론 (isonoruron), 이소폴리네이트 (isopolinate), 이소프로팔린 (isopropalin), 이소프로투론 (isoproturon), 이소우론 (isouron), 이속사벤 (isoxaben), 이속사클로르톨 (isoxachlortole), 이속사플루톨 (isoxaflutole), 이속사피리폽 (isoxapyrifop), 카르부틸레이트 (karbutilate), 케토스피라독스 (ketospiradox), 쿠이카옥시 (kuicaoxi), 락토펜 (lactofen), 레나실 (lenacil), 리누론 (linuron), MAA, MAMA, MCPA, MCPA-티오에틸 (MCPA-thioethyl), MCPB, 메코프롭 (mecoprop), 메코프롭-P (mecoprop-P), 메디노테르브 (medinoterb), 메페나세트 (mefenacet), 메플루이디드 (mefluidide), 메소프라진 (mesoprazine), 메소술푸론 (mesosulfuron), 메소트리온 (mesotrione), 메탐 (metam), 메타미폽 (metamifop), 메타미트론 (metamitron), 메타자클로르 (metazachlor), 메타조술푸론 (metazosulfuron), 메트플루라존 (metflurazon), 메타벤즈티아주론 (methabenzthiazuron), 메탈프로팔린 (methalpropalin), 메타졸 (methazole), 메티오벤카르브 (methiobencarb), 메티오피리술푸론 (methiopyrisulfuron), 메티오졸린 (methiozolin), 메티우론 (methiuron), 메토메톤 (methometon), 메토프로트린 (methoprotryne), 메톡시페논 (methoxyphenone), 브롬화메틸 (methyl bromide), 요오드화메틸 (methyl iodide), 이소티오시안산메틸 (methyl isothiocyanate), 메틸다임론 (methyldymron), 메토벤주론 (metobenzuron), 메토브로무론 (metobromuron), 메톨라클로르 (metolachlor), 메토술람 (metosulam), 메톡수론 (metoxuron), 메트리부진 (metribuzin), 메트술푸론 (metsulfuron), 몰리네이트 (molinate), 모날리드 (monalide), 모니소우론 (monisouron), 모노클로로아세트산 (monochloroacetic acid), 모노리누론 (monolinuron), 모노술푸론 (monosulfuron), 모누론 (monuron), 모르팜콰트 (morfamquat), MSMA, 나밤 (nabam), 나프로아닐리드 (naproanilide), 나프로파미드-M (napropamide-M), 납탈람 (naptalam), 네부론 (neburon), 니코술푸론 (nicosulfuron), 니피라클로펜 (nipyraclofen), 니트랄린 (nitralin), 니트로펜 (nitrofen), 니트로플루오르펜 (nitrofluorfen), 노르플루라존 (norflurazon), 노루론 (noruron), OCH, 오르벤카르브 (orbencarb), o-디클로로벤젠 (ortho-dichlorobenzene), 오르토술파무론 (orthosulfamuron), 오리잘린 (oryzalin), 옥사디아르길 (oxadiargyl), 옥사디아존 (oxadiazon), 옥사피라존 (oxapyrazon), 옥사술푸론 (oxasulfuron), 옥사지클로메폰 (oxaziclomefone), 옥시플루오르펜 (oxyfluorfen), 파라플루론 (parafluron), 파라콰트 (paraquat), 페불레이트 (pebulate), 펠라르곤산 (pelargonic acid), 펜디메탈린 (pendimethalin), 페녹스술람 (penoxsulam), 라우르산펜타클로로페닐 (pentachlorophenyl laurate), 펜타노클로르 (pentanochlor), 펜톡사존 (pentoxazone), 퍼플루이돈 (perfluidone), 페톡사미드 (pethoxamid), 페니소팜 (phenisopham), 펜메디팜 (phenmedipham), 펜메디팜-에틸 (phenmedipham-ethyl), 페노벤주론 (phenobenzuron), 피클로람 (picloram), 피콜리나펜 (picolinafen), 피녹사덴 (pinoxaden), 피페로포스 (piperophos), 프레틸라클로르 (pretilachlor), 프리미술푸론 (primisulfuron), 프로시아진 (procyazine), 프로디아민 (prodiamine), 프로플루아졸 (profluazol), 프로플루랄린 (profluralin), 프로폭시딤 (profoxydim), 프로글리나진 (proglinazine), 프로메톤 (prometon), 프로메트린 (prometryn), 프로파클로르 (propachlor), 프로파닐 (propanil), 프로파퀴자폽 (propaquizafop), 프로파진 (propazine), 프로팜 (propham), 프로피소클로르 (propisochlor), 프로폭시카르바존 (propoxycarbazone), 프로피리술푸론 (propyrisulfuron), 프로피자미드 (propyzamide), 프로술팔린 (prosulfalin), 프로술포카르브 (prosulfocarb), 프로술푸론 (prosulfuron), 프록산 (proxan), 프리나클로르 (prynachlor), 피다논 (pydanon), 피라클로닐 (pyraclonil), 피라플루펜 (pyraflufen), 피라술포톨 (pyrasulfotole), 피라졸리네이트 (pyrazolynate), 피라조술푸론 (pyrazosulfuron), 피라족시펜 (pyrazoxyfen), 피리밤벤즈-이소프로필 (pyribambenz-isopropyl), 피리밤벤즈-프로필 (pyribambenz-propyl), 피리벤족심 (pyribenzoxim), 피리벤카르브 (pyributicarb), 피리클로르 (pyriclor), 피리다폴 (pyridafol), 피리데이트 (pyridate), 피리프탈리드 (pyriftalid), 피리미노박 (pyriminobac), 피리미술판 (pyrimisulfan), 피리티오백 (pyrithiobac), 피록사술폰 (pyroxasulfone), 피록시술람 (pyroxsulam), 퀸클로락 (quinclorac), 퀸메락 (quinmerac), 퀴노클라민 (quinoclamine), 퀴노나미드 (quinonamid), 퀴잘로폽 (quizalofop), 퀴잘로폽-P (quizalofop-P), 로데타닐 (rhodethanil), 림술푸론 (rimsulfuron), 사플루페나실 (saflufenacil), 세부틸라진 (sebuthylazine), 섹부메톤 (secbumeton), 세톡시딤 (sethoxydim), shuangjiaancaolin, 시두론 (siduron), 시마진 (simazine), 시메톤 (simeton), 시메트린 (simetryn), SMA, S-메톨라클로르 (S-metolachlor), 염소산나트륨 (sodium chlorate), 술코트리온 (sulcotrione), 술팔레이트 (sulfallate), 술펜트라존 (sulfentrazone), 술포메투론 (sulfometuron), 술포술푸론 (sulfosulfuron), 술글리카핀 (sulglycapin), 스웹 (swep), 태브론 (tavron), TCA, 테부탐 (tebutam), 테부티우론 (tebuthiuron), 테푸릴트리온 (tefuryltrione), 템보트리온 (tembotrione), 테프랄록시딤 (tepraloxydim), 테르바실 (terbacil), 테르부카르브 (terbucarb), 테르부클로르 (terbuchlor), 테르부메톤 (terbumeton), 테르부틸라진 (terbuthylazine), 테르부트린 (terbutryn), 테르부트린 (terbutryn), 테트라플루론 (tetrafluron), 테닐클로르 (thenylchlor), 티아자플루론 (thiazafluron), 티아조피르 (thiazopyr), 티디아지민 (thidiazimin), 티디아주론 (thidiazuron), 티엔카르바존 (thiencarbazone), 티펜술푸론 (thifensulfuron), 티오벤카르브 (thiobencarb), 티아페나실 (tiafenacil), 티오카르바질 (tiocarbazil), 티오클로림 (tioclorim), 톨피랄레이트 (tolpyralate), 토프라메존 (topramezone), 트랄콕시딤 (tralkoxydim), 트리아파몬 (triafamone), 트리알레이트 (tri-allate), 트리아술푸론 (triasulfuron), 트리아지플람 (triaziflam), 트리베누론 (tribenuron), 트리캄바 (tricamba), 트리클로피르 (triclopyr), 트리디판 (tridiphane), 트리에타진 (trietazine), 트리플록시술푸론 (trifloxysulfuron), 트리플루디목사진 (trifludimoxazin), 트리플루랄린 (trifluralin), 트리플루술푸론 (triflusulfuron), 트리폽 (trifop), 트리폽심 (trifopsime), 트리하이드록시트리아진 (trihydroxytriazine), 트리메투론 (trimeturon), 트리프로핀단 (tripropindan), 트리탁 (tritac), 트리토술푸론 (tritosulfuron), 버놀레이트 (vernolate), 크실라클로르 (xylachlor), zuomihuanglong, DAH-500, SL-261 등을 들 수 있다.
생물 농약의 예로는, 핵다각체 바이러스 (Nuclear polyhedrosis virus, NPV), 과립병 바이러스 (Granulosis virus, GV), 세포질 다각체병 바이러스 (Cytoplasmic polyhedrosis virus, CPV), 스테이너네마 카포캅사에 (Steinernema carpocapsae), 스테이너네마 글라세라이 (Steinernema glaseri), 모노크로스포리움 피마토파감 (Monacrosporium phymatophagum), 스테이너네마 쿠시다이 (Steinernema kushidai), 파스테우리아 페네트란스 (Pasteuria penetrans), 아그로박테리움 라디오박터 (Agrobacterium radiobacter), 바실러스 섭틸리스 (Bacillus subtilis), 바실러스 아밀로리퀘파시엔스 (Bucillus amyloliquefaciens), 에르비니아 카로토보라 (Erwinia carotovora), 슈도모나스 플루오레센스 (Pseudomonas fluorescens), 탈라로마이세스 플라부스 (Talaromyces flavus), 트리코데르마 아트로비리데 (Trichoderma atroviride), 바실러스 튜링겐시스 (Bacillus thuringiensis), 보베리아 브론니아르티 (Beauveria brongniartii), 보베리아 바시아나 (Beauveria bassiana), 파에실로마이세스 푸모소로세우스 (Paecilomyces fumosoroseus), 버티실리움 레카니 (Verticillium lecanii), 크산토모나스 캄페스트리스 (Xanthomonas campestris), 온실가루이좀벌 (Encarsia formosa), 황온좀벌 (Eretmocerus eremicus), 담배가루이좀벌 (Eretmocerus mundus), 콜레마니진디벌 (Aphidoletes aphidimyza), 진디혹파리 (Aphidoletes aphidimyza), 굴파리좀벌 (Diglyphus isaea), 잎굴파리고치벌 (Dacnusa sibirica), 칠레이리응애 (Phytoseiulus persimilis), 오이이리응애 (Amblyseius cucumeris), 사막이리응애 (Amblyseius californicus), 으뜸애꽃노린재 (Orius strigicollis) 등을 들 수 있다.
페로몬제 (해충 유인제) 의 예로는, 브레비코민 (brevicomin), 세랄루어 (ceralure), 코들레루어 (codlelure), 큐루어 (cue-lure), 디스팔루어 (disparlure), 도미니칼루어 1 (dominicalure-1), 오이게놀 (eugenol), 프론탈린 (frontalin), 고시플루어 (gossyplure), 그란딜루어 (grandlure), 헥사루어 (hexalure), 입스디에놀 (ipsdienol), 입세놀 (ipsenol), 자포닐루어 (japonilure), 라틸루어 (latilure), 리네아틴 (lineatin), 리틀루어 (litlure), 루플루어 (looplure), 메들루어 (medlure), 메가토모산 (megatomoic acid), 메틸오이게놀 (methyl eugenol), moguchun, 무스칼루어 (muscalure), 오르프랄루어 (orfralure), 오릭탈루어 (oryctalure), 오스트라몬 (ostramone), 레스칼루어 (rescalure), 시글루어 (siglure), 술카톨 (sulcatol), 트리메들루어 (trimedlure), 트런크콜 (trunc-call), α-멀티스트리아틴 (α-multistriatin) 등을 들 수 있다.
페로몬제 (해충 기피제) 로는, 아크렙 (acrep), 부토피로녹실 (butopyronoxyl), 캄퍼 (camphor), d-캄퍼 (d-camphor), 카르복시미드 (carboxide), 프탈산디부틸 (dibutyl phthalate), 디에틸톨루아미드 (diethyltoluamide), 탄산디메틸 (dimethyl carbate), 프탈산디메틸 (dimethyl phthalate), 숙신산디부틸 (dibutyl succinate), 에토헥사디올 (ethohexadiol), 헥산산아미드 (hexamide), 이카리딘 (icaridin), 메토퀸-부틸 (methoquin-butyl), 메틸네오데카나미드 (methylneodecanamide), 2-(메틸티오)에탄올 (2-(octylthio)ethanol), 옥사메이트 (oxamate), 쿠웬치 (quwenzhi), 쿠잉딩 (quyingding), 레베미드 (rebemide), zengxiaoan 등을 들 수 있다.
천연 살균제·천연 살충제의 예로는, 머신유 (machine oils), 메틸페닐아세테이트 (methylphenyl acetate), α-피넨 (α-pinene), 단백 가수 분해물 (protein hydrolysate), (Z)-1-테트라데켄-1-올 ((Z)-1-Tetradecen-1-ol), 테르핀유 (Turpentine) 등을 들 수 있다.
본 발명에 의한 살균성 조성물은 또한, 필요에 따라 발근 촉진제 등의 식물 성장 조정제, 식물 영양분 등의 비료 등의 적어도 1 종의 생물학적으로 유효한 성분을 공동 성분으로서 포함함으로써, 더욱 넓은 범위의 농업 보호를 가져오는 다구성 성분 유해 생물 방제제를 형성하는 것도 가능하다.
본 발명의 살균성 조성물에 있어서의 구성 성분 (a) 식 [1] 로 나타내는 화합물 또는 그 염과 구성 성분 (b) 로 나타내는 농원예용 살균제 또는 그 염의 중합 혼합비는 1 : 3000 ∼ 3000 : 1 의 비율이고, 바람직하게는 1 : 1000 ∼ 1000 : 1 이다.
본 발명의 살균성 조성물의 시용량은, 대상 작물, 대상 병해, 발생 경향, 환경 조건 그리고 사용하는 제형 등에 따라 바뀌지만, 분말제 및 입제 등과 같이 그대로 사용하는 경우에는, 유효 성분으로서 1 헥타르당 1 g ∼ 50 ㎏, 바람직하게는 10 g ∼ 10 ㎏ 의 범위에서 적절히 선택하는 것이 바람직하다. 또한, 유제, 수화제 및 플로어블제 등으로 하는 경우와 같이 액상으로 사용하는 경우에는, 0.1 ∼ 50,000 ppm, 바람직하게는 10 ∼ 10,000 ppm 의 범위에서 적절히 선택하는 것이 바람직하다.
실시예
본 명세서에 기재된 식 [1] 의 화합물 및 중간체에 대하여, 다양한 구전자 반응, 구핵 반응, 라디칼 반응, 유기 금속 반응, 산화 반응, 환원 반응을 실시하고, 치환기를 추가하거나 기존의 치환기를 수식할 수 있는 것은, 당업자이면 인식할 것이다.
더 이상 상세하게 설명하지 않아도, 상기 서술한 설명을 사용하는 당업자이면, 본 발명을 최대한으로 이용할 수 있을 것으로 생각된다. 따라서, 이하의 실시예는 단순히 예시적인 것으로 해석되고, 본 개시를 전혀 한정하는 것이 아니다. 이하의 예에서의 공정은 전체적인 합성 전개에 있어서의 각 공정의 순서를 설명하는 것으로, 각 공정의 출발 원료가, 다른 예 또는 공정에 순서를 기재한 특정한 조제의 실시에 의해 반드시 조제될 필요는 없다.
또한, 이하의 설명에 있어서 「%」 는 중량 백분율을 나타내고, 「부」 는 중량부를 나타낸다.
실시예 1 : 4-[4-(6,9-디플루오로-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (화합물 1-3) 의 조제
4-(4-포르밀-2-티아졸릴)-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (210 ㎎) (WO2008/013622호에 기재된 화합물) 과, 3,6-디플루오로-1,2-벤젠디메탄올 (210 ㎎) 과, 파라톨루엔술폰산 1 수화물 (11 ㎎) 을, 톨루엔 (15 ㎖) 에 용해시키고, Dean-Stark 장치를 사용하여 1 시간 가열 환류하였다. 반응액을 실온까지 냉각 후, 아세트산에틸로 희석하고, 물 및 포화 식염수로 세정하였다. 유기층을 무수 황산나트륨으로 건조시키고, 무기물을 여과 분리한 후, 감압하 용매를 증류 제거하였다. 잔류물을 플래시 자동 정제 장치 (biotage AB 사 제조/IsoleraTM) 에 의한 플래시 실리카 겔 칼럼 크로마토그래피 (아세트산에틸-헥산 : 40 % - 100 % 로 용출) 를 사용하여 정제함으로써 표제 화합물을 백색 아모르퍼스상 고체 (245 ㎎, 수율 83 %) 로서 얻었다.
실시예 2 : 4-[4-(6-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (화합물 1-6) 의 조제
4-(4-포르밀-2-티아졸릴)-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (200 ㎎) 과, 3-메틸술포닐옥시-1,2-벤젠디메탄올 (121 ㎎) 과, 파라톨루엔술폰산 1 수화물 (20 ㎎) 을, 톨루엔 (20 ㎖) 에 용해시키고, 화합물 1-3 의 조제에 있어서의 반응과 동일하게 반응시키고, 정제함으로써, 표제 화합물을 백색 아모르퍼스상 고체 (298 ㎎, 수율 96 %) 로서 얻었다.
실시예 3 : 4-[4-(6-플루오로-9-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (화합물 1-8) 의 조제
4-(4-포르밀-2-티아졸릴)-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (220 ㎎) 과, 3-플루오로-6-메틸술포닐옥시-1,2-벤젠디메탄올 (150 ㎎) 과, 파라톨루엔술폰산 1 수화물 (20 ㎎) 을, 톨루엔 (15 ㎖) 에 용해시키고, 화합물 1-3 의 조제에 있어서의 반응과 동일하게 반응시키고, 정제함으로써, 표제 화합물을 백색 아모르퍼스상 고체 (297 ㎎, 수율 84 %) 로서 얻었다. 얻어진 수지상물에 메탄올을 첨가하고, 가열 환류하 용해시킨 후에, 실온에서 정치함으로써 백색 고체 (융점 151 ℃) 를 얻었다.
실시예 4 : 4-[4-(6-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (화합물 1-38) 의 조제
4-(4-포르밀-2-티아졸릴)-1-[2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (202 ㎎) (WO2010/066353호에 기재된 화합물) 과, 3-메틸술포닐옥시-1,2-벤젠디메탄올 (232 ㎎) 과, 파라톨루엔술폰산 1 수화물 (5 ㎎) 을, 톨루엔 (15 ㎖) 에 용해시키고, 화합물 1-3 의 조제에 있어서의 반응과 동일하게 반응시키고, 정제함으로써, 표제 화합물을 백색 아모르퍼스상 고체 (164 ㎎, 수율 53 %) 로서 얻었다.
실시예 5 : 4-[4-(6-메톡시-9-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (화합물 1-39) 의 조제
4-(4-포르밀-2-티아졸릴)-1-[2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (202 ㎎) 과, 3-메톡시-6-메틸술포닐옥시-1,2-벤젠디메탄올 (232 ㎎) 과, 파라톨루엔술폰산 1 수화물 (5 ㎎) 을, 톨루엔 (15 ㎖) 에 용해시키고, 화합물 1-3 의 조제에 있어서의 반응과 동일하게 반응시키고, 정제함으로써, 표제 화합물을 백색 아모르퍼스상 고체 (268 ㎎, 수율 75 %) 로서 얻었다. 얻어진 수지상물에 메탄올을 첨가하고, 가열 환류하 용해시킨 후에, 실온에서 정치 (靜置) 함으로써 백색 고체 (융점 123 - 125 ℃) 를 얻었다.
실시예 6 : 4-[4-(6-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[3,5-비스(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (화합물 1-42) 의 조제
4-(4-포르밀-2-티아졸릴)-1-[2-[3,5-비스(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (200 ㎎) (4-(4-포르밀-2-티아졸릴)-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘과 동일한 방법으로 합성하였다) 과, 3-메틸술포닐옥시-1,2-벤젠디메탄올 (109 ㎎) 과, 파라톨루엔술폰산 1 수화물 (5 ㎎) 을, 톨루엔 (100 ㎖) 에 용해시키고, 화합물 1-3 의 조제에 있어서의 반응과 동일하게 반응시키고, 정제함으로써, 표제 화합물을 백색 아모르퍼스상 고체 (96 ㎎, 수율 31 %) 로서 얻었다.
실시예 7 : 4-[4-(6,9-디플루오로-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[3,5-비스(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (화합물 1-50) 의 조제
4-(4-포르밀-2-티아졸릴)-1-[2-[3,5-비스(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (200 ㎎) 과, 3,6-디플루오로-1,2-벤젠디메탄올 (82 ㎎) 과, 파라톨루엔술폰산 1 수화물 (5 ㎎) 을, 톨루엔 (100 ㎖) 에 용해시키고, 화합물 1-3 의 조제에 있어서의 반응과 동일하게 반응시키고, 정제함으로써, 표제 화합물을 백색 아모르퍼스상 고체 (183 ㎎, 수율 53 %) 로서 얻었다.
실시예 8 : 4-[4-(6-플루오로-9-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (화합물 1-62) 의 조제
4-(4-포르밀-2-티아졸릴)-1-[2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘 (202 ㎎) 과, 3-플루오로-6-메틸술포닐옥시-1,2-벤젠디메탄올 (250 ㎎) 과, 파라톨루엔술폰산 1 수화물 (5 ㎎) 을, 톨루엔 (15 ㎖) 에 용해시키고, 화합물 1-3 의 조제에 있어서의 반응과 동일하게 반응시키고, 정제함으로써, 표제 화합물을 백색 아모르퍼스상 고체 (105 ㎎, 수율 33 %) 로서 얻었다.
이하의 실시예 9 ∼ 12 에, 상기 실시예 1 ∼ 8 에 있어서 사용한 제조 출발 물질의 제조예를 나타낸다.
실시예 9 : 3,6-디플루오로-1,2-벤젠디메탄올의 조제
테트라하이드로푸란 27 ㎖ 에 수소화알루미늄리튬 (870 ㎎) 과 3,6-디플루오로프탈산 무수물을, 빙냉하, 순서대로 용해시키고, 반응액을 2 시간 가열 환류하였다. 반응액을 실온까지 냉각 후, 빙냉하, 물을 첨가하고 실온에서 1 시간 교반하였다. 셀라이트를 사용하여 용액을 여과하고, 감압하 용매를 증류 제거함으로써 표제 화합물을 백색 고체 (640 ㎎, 수율 68 %) 로서 얻었다.
1H-NMR (CDCl3/TMS δ(ppm) 치) : 2.89(brs, 2H), 4.84(s, 4H), 7.03(dd, 2H)
실시예 10 : 3-메틸술포닐옥시-1,2-벤젠디메탄올의 조제
3-메틸술포닐옥시프탈산 무수물 (2.2 g) (WO2004/000796호에 기재된 화합물) 을 테트라하이드로푸란 (60 ㎖) 에 용해시키고, 보란테트라하이드로푸란 착물 (0.9 M 테트라하이드로푸란 용액, 50 ㎖) 을 첨가하고, 60 ℃ 에서 6 시간 교반하였다. 반응 종료 후, 빙냉하 메탄올을 첨가하고, 감압하 용매를 증류 제거하였다. 잔류물을 아세트산에틸로 희석하고, 1 N 염산, 포화 식염수로 세정하였다. 유기층을 무수 황산나트륨으로 건조시키고, 무기물을 여과 분리한 후, 감압하 용매를 증류 제거하였다. 잔류물을 플래시 자동 정제 장치 (biotage AB 사 제조/IsoleraTM) 에 의한 플래시 실리카 겔 크로마토그래피 (아세트산에틸-헥산 : 30 % - 100 % 로 용출) 를 사용하여 정제함으로써 3-메틸술포닐옥시-1,2-벤젠디메탄올을 백색 고체 (1.36 ㎎, 수율 64 %, 융점 56 ∼ 58 ℃) 로서 얻었다.
1H-NMR (DMSO-d6/TMS δ (ppm) 치) : 3.42(s, 3H), 4.57(d, 2H), 4.70(d, 2H), 4.98(t, 1H), 5.27(t, 1H), 7.25(d, 1H), 7.36(t, 1H), 7.46(d, 1H)
실시예 11 : 3-플루오로-6-메틸술포닐옥시-1,2-벤젠디메탄올의 조제
공정 1 : 5-플루오로-2-메틸술포닐옥시프탈리드의 조제
5-플루오로-2-하이드록시프탈리드 (200 ㎎) (WO2003/076424호에 기재된 화합물) 를 N,N-디메틸포름아미드 (10 ㎖) 에 용해시키고, 메틸술포닐클로라이드 (150 ㎎) 와 트리에틸아민 (133 ㎎) 을 첨가하고, 실온에서 하룻밤 교반하였다. 반응액을 아세트산에틸로 희석하고, 포화 식염수로 세정하였다. 유기층을 무수 황산나트륨으로 건조시키고, 무기물을 여과 분리한 후, 감압하 용매를 증류 제거함으로써 5-플루오로-2-메틸술포닐옥시프탈리드를 백색 고체 (290 ㎎, 수율 100 %) 로서 얻었다.
공정 2 : 3-플루오로-6-메틸술포닐옥시-1,2-벤젠디메탄올의 조제
5-플루오로-2-메틸술포닐옥시프탈리드 (290 ㎎) 를 테트라하이드로푸란 (10 ㎖) 에 용해시키고, 수소화알루미늄리튬 (45 ㎎) 을 첨가하고, 실온에서 30 분 교반하였다. 반응액에, 빙냉하, 1 N 염산을 첨가하고 실온에서 1 시간 교반하였다. 반응액을 디클로로메탄을 사용하여 추출하고, 포화 식염수로 세정하였다. 유기층을 무수 황산나트륨으로 건조시키고, 무기물을 여과 분리한 후, 감압하 용매를 증류 제거함으로써 3-플루오로-6-메틸술포닐옥시-1,2-벤젠디메탄올을 백색 고체 (290 ㎎, 수율 100 %, 융점 85 ∼ 87 ℃) 로서 얻었다.
1H-NMR (CDCl3/TMS δ (ppm) 치) : 3.28(s, 3H), 3.45(brs, 2H), 4.84(s, 4H), 7.11(dd, 1H), 7.25 ∼ 7.28(m, 1H)
실시예 12 : 3-메톡시-6-메틸술포닐옥시-1,2-벤젠디메탄올의 조제
공정 1 : 2,3-비스(메톡시카르보닐)-1-메톡시-4-메틸술포닐옥시벤젠의 조제
2,3-비스(메톡시카르보닐)-4-메톡시페놀 (2.0 g) (Synthetic Communication, 43(2), 260-267 ; 2013에 기재된 화합물) 을 테트라하이드로푸란 (30 ㎖) 에 용해시키고, 메틸술포닐클로라이드 (1.05 g) 와 트리에틸아민 (1.01 g) 을 첨가하고, 실온에서 1 시간 교반하였다. 반응액에 물을 첨가하고, 아세트산에틸로 추출한 후, 포화 식염수로 세정하였다. 유기층을 무수 황산나트륨으로 건조시키고, 무기물을 여과 분리한 후, 감압하 용매를 증류 제거함으로써 2,3-비스(메톡시카르보닐)-1-메톡시-4-메틸술포닐옥시벤젠을 백색 고체 (2.5 g, 수율 100 %) 로서 얻었다.
공정 2 : 3-메톡시-6-메틸술포닐옥시-1,2-벤젠디메탄올의 조제
2,3-비스(메톡시카르보닐)-1-메톡시-4-메틸술포닐옥시벤젠 (2.5 g) 을 테트라하이드로푸란 (30 ㎖) 에 용해시키고, 빙냉하, 수소화알루미늄리튬 (620 ㎎) 을 첨가하고, 빙냉하에서 1 시간 교반하였다. 반응액에, 빙냉하, 1 N 염산을 첨가하고 실온에서 1 시간 교반하였다. 반응액을 아세트산에틸을 사용하여 추출하고, 포화 식염수로 세정하였다. 유기층을 무수 황산나트륨으로 건조시키고, 무기물을 여과 분리한 후, 감압하 용매를 증류 제거하였다. 잔류물을 플래시 자동 정제 장치 (biotage AB 사 제조/IsoleraTM) 에 의한 플래시 실리카 겔 크로마토그래피 (아세트산에틸-헥산 : 30 % - 100 % 로 용출) 를 사용하여 정제함으로써 3-메톡시-6-메틸술포닐옥시-1,2-벤젠디메탄올을 백색 고체 (906 ㎎, 수율 42 %) 로서 얻었다.
1H-NMR(DMSO-d6/TMS δ (ppm) 치) : 3.39(s, 3H), 3.81(s, 3H), 4.62 ∼ 4.64(m, 4H), 4.84(t, 1H), 5.06(t, 1H), 7.03(d, 1H), 7.28(d, 1H)
동일한 제조법에 의해, [표 5] 내지 [표 8] 에 나타내는 화합물 1-1, 1-2, 1-4, 1-5, 1-7, 1-9 ∼ 1-37, 1-40, 1-41, 1-43 ∼ 1-49, 1-51 ∼ 1-61, 및 1-63 ∼ 1-161 을 합성하였다.
[표 5]
[표 6]
[표 7]
[표 8]
상기 실시예에서 얻어진 화합물 및 동일한 방법으로 제조한 본 발명 화합물의 1H-NMR 데이터 (CDCl3/TMS δ (ppm) 치) 를 [표 9] 내지 [표 18] 에 나타낸다.
[표 9]
[표 10]
[표 11]
[표 12]
[표 13]
[표 14]
[표 15]
[표 16]
[표 17]
[표 18]
다음으로, 본 발명의 제제화 실시예를 기재한다.
<제제예 1> 수화제
본 발명의 화합물 5 부, 메탈락실-M 5 부, 라우릴황산나트륨 2 부, 리그닌 술폰산나트륨 4 부, 화이트 카본 20 부 및 클레이 64 부를 혼합하고, 분쇄하여 10 % 수화제를 얻었다.
<제제예 2> 플로어블제
본 발명의 화합물 5 부, 클로로타로닐 5 부, 폴리옥시에틸렌알릴페닐에테르설페이트 4 부, 폴리옥시에틸렌알킬에테르 5 부, 프로필렌글리콜 5 부, 실리콘계 소포제 0.2 부, 나트륨몬모릴로나이트 0.8 부, 물 50 부를 첨가하고 혼합하여 다이노밀을 사용하여 습식 분쇄하여 분쇄 현탁액을 얻었다.
분쇄 현탁액 75 부에, 잔탄검, 2-벤즈이소티아졸린-3-온을 각각 0.2 부, 0.1 부를 포함하는 잔탄검 용액 10 부와 물 15 부를 첨가한 후, 혼합하여 10 % 수성 현탁상 농약 조성물을 얻었다.
<제제예 3> 유제
본 발명의 화합물 5 부, 아족시스트로빈 5 부, 도데실벤젠술폰산칼슘 2 부, 피마자유 에톡실레이트 15 부를 방향족 탄화수소 혼합물 73 부와 혼합하여 용해시켜 균질의 10 % 가 (可) 유화 유상 액체를 얻었다.
<제제예 4> 과립 수화제
본 발명의 화합물 5 부, 벤티아발리카르브이소프로필 5 부, 리그닌 술폰산나트륨 20 부, 나프탈렌술폰산 축합물의 나트륨염 10 부, 알킬벤젠술폰산나트륨 3 부, 실리콘계 소포제 0.5 부, 규조토 5 부, 황산암모늄 10 부, 탤크 10 부, 클레이 31.5 부를 첨가하여 충분히 교혼합하여 분쇄하여 분쇄물을 얻었다. 분쇄물에 필요에 따라 적당량의 물을 첨가하여 조립기로 조립하고, 건조 후에 체로 걸러 10 % 수화성 세립을 얻었다.
<제제예 5> 에멀션제
본 발명의 화합물 5 부, 시아조파미드 5 부, 방향족 탄화수소 혼합물 15 부, 도데실벤젠술폰산칼슘 2 부, 폴리옥시에틸렌 피마자유 20 부, 프로필렌글리콜 4 부 첨가하여 용해시켜 혼합액을 얻었다. 물 49 부에 혼합액을 첨가하고 호모게나이저를 사용하여 혼합하여 균질의 10 % 유탁액체를 얻었다.
<제제예 6> 입제
본 발명의 화합물 5 부, 아미술브롬 5 부, 폴리카르복실산형 아니온 계면 활성제 3 부, 디옥틸술포숙시네이트나트륨 0.2 부, 덱스트린 2 부, 벤토나이트 나트륨 15 부, 탄산칼슘 69.8 부를 첨가하여 균일 혼합한 후 적당량의 물을 첨가하여 혼련하고, 바스켓형 조립기로 압출 조립하여 건조 후에 체로 걸러 10 % 세립을 얻었다.
<제제예 7> 마이크로 에멀션제
본 발명의 화합물 5 부, 만디프로파미드 5 부와 지방산 디메틸아미드 12 부, 시클로헥사논 10 부, 아릴페놀에톡실레이트 15 부를 혼합하고, 알코올에톡실레이트 10 부 및 물을 43 부 첨가하여 가온하에서 수분간 교반하여, 안정적인 10 % 수용성 액체를 얻었다.
다음으로, 본 발명의 생물학적 실시예를 기재한다.
(1) 시험 현탁액의 조제의 실시 순서
시험 1 ∼ 2 용의 시험 현탁액을 조정하기 위해서, 제제예 1 에 따라, 본 발명의 화합물 10 부를, 라우릴황산나트륨 2 부, 리그닌 술폰산나트륨 4 부, 화이트 카본 20 부 및 클레이 64 부를 혼합하고, 분쇄하여 각 화합물 10 % 수화제로서 제작하였다. 구성 성분 (b) 중, 벤티아발리카르브, 발리페날레이트, 족사미드, 파목사돈, 이프로발리카르브, 페나미돈, 플루오피콜리드, 아메톡트라딘, 옥사티아피프롤린을 미배합의 공업 그레이드 재료로서 입수하고, 상기 예에 따라 10 % 수화제로서 제작하였다. 또한, 시아조파미드, 만디프로파미드, 메탈락실-M, 에타복삼, 디메토모르프, 시목사닐, 염기성 황산동, 클로로타로닐, 만제브, 프로피네브, 캡탄, 크레속심-메틸, 아족시스트로빈, 트리플록시스트로빈, 플루아지남, 피리벤카르브, 펜티오피라드, 퀴녹시펜, 피리오페논, 프로파모카르브, 포세틸-알루미늄, 이미녹타딘, 플루디옥소닐, 티오파네이트-메틸, 이프로디온, 테부코나졸, 시프로디닐, 아미술브롬, 트리시클라졸, 폴리옥신, 테부플로퀸, 프로피코나졸은, 각각 시판되고 있는 제품으로서 입수하였다. 각 화합물은, 각각 증류수 중에 분산시켜 원하는 농도로 조정하고, 얻어진 시험 현탁액을 시험 1 ∼ 2 에 사용하였다. 시험 현탁액 중에는 유기 용제, 계면 활성제 등은 첨가하지 않았다.
(2) 식물 병해에 대한 방제 효과의 평가 시험 순서
<시험 1 토마토 역병에 대한 방제 효과 시험>
5 엽기의 토마토 (품종 : 레지나) 에 시험 현탁액을 1 모종 당 20 ㎖ 산포하였다. 산포 1 일 후에 1.0 × 105 개/㎖ 의 농도로 조제한 피토프토라인 페스탄스 (Phytophthorain festans) 의 유주자 현탁액을 분무 접종하고, 22 ℃ 로 조절한 습실에 16 시간 인큐베이트하였다. 그 후, 실내에서 발병을 촉진시키고, 접종으로부터 4 일 후에 잎에 발생한 병반 면적률을 조사하고, 이하의 식을 사용하여 방제가를 산출하였다.
방제가의 산출식 : 방제가치 = {1 - 시험 약제를 산포한 잎의 발병 면적률/무처리의 발병 면적률} × 100
<시험 2 오이노균병에 대한 방제 효과 시험>
2 엽기의 오이 (품종 : 사가미 한지로) 에 시험 현탁액을 1 모종 당 20 ㎖ 산포하였다. 산포 1 일 후에 1.0 × 104 개/㎖ 의 농도로 조제한 프세우도페로노스포라 쿠벤시스 (Pseudoperonospora cubensis) 의 유주자낭 현탁액을 분무 접종하고, 22 ℃ 로 조절한 습실에 16 시간 인큐베이트하였다. 그 후, 실내에서 발병을 촉진시키고, 접종으로부터 5 일 후에 잎에 발생한 병반 면적률을 조사하고, 이하의 식을 사용하여 방제가를 산출하였다.
방제가의 산출식 : 방제가치 = {1 - 시험 약제를 산포한 잎의 발병 면적률/무처리의 발병 면적률} × 100
(3) 상승 효과의 평가 시험 순서
2 종의 화합물 처방 성분간의 상승 효과의 존재는, 이하의 Colby 식 (Colby, S. R. 「Calculating of Herbicide Combinations」, Weeds, (1967년), 15, 20 ∼ 22 페이지를 참조할 것) 을 사용하여 확정하였다.
Colby 법을 사용함으로써, 2 종의 화합물 처방 성분 사이에 있어서의 상승적 상호 작용의 존재는, 먼저, 단독으로 적용된 2 종의 구성 성분의 활성에 기초하여, 혼합물의 예측된 활성 p 를 산출하는 것에 의해 확정된다. p 가 실험적으로 확정된 효과보다 낮으면, 상승 작용이 발생한 것이 된다. 상기 식에 있어서, A 는, 비율 x 로 단독으로 적용된 제 1 구성 성분의 방제 비율에서의 살균·살곰팡이 활성이다. B 는, 비율 y 로 적용된 제 2 구성 성분의 방제 비율에서의 살균·살곰팡이 활성이다. 이 식은, 효과가 엄밀하게 상가적이어서 상호 작용이 발생하지 않은 경우의, 비율 x 에서의 A 와 비율 y 에서의 B 의 혼합물의 예측된 살균·살곰팡이 활성 p 를 추정한다.
(4) 식물 병해 <시험 1> 및 <시험 2> 에 대한 결과
먼저, 본 발명의 화합물의 결과를 이하에 나타낸다. 여기서는 4 ppm 의 시험 현탁액을 사용했을 때에 방제가 90 이상을 나타낸 화합물 No. 를 기재한다. <시험 1> 에 있어서는 화합물 No. 1-1 ∼ 1-42, 1-44 ∼ 1-88 및 1-90 ∼ 161 이었다. 또한, <시험 2> 에 있어서는 화합물 No. 1-1 ∼ 1-8 및 1-10 ∼ 1-161 이었다.
다음으로, 상승 효과의 결과를 [표 19] 내지 [표 28] 에 나타낸다. 각 표는, 동시에 실시한 일련의 평가에 상당한다. <시험 1> 및 <시험 2> 의 난에 기재한 숫자는 방제가를 나타내고, 「실측」 이라고 나타낸 난은, 3 회의 반복으로부터 얻어진 결과의 평균치이고, 「예측」 이라고 나타낸 난은, Colby 식을 사용하여 산출한 각 처리 조성물에 대한 예측치를 나타낸다.
[표 19-1]
[표 19-2]
[표 20-1]
[표 20-2]
[표 21-1]
[표 21-2]
[표 22-1]
[표 22-2]
[표 23-1]
[표 23-2]
[표 24-1]
[표 24-2]
[표 25-1]
[표 25-2]
[표 26-1]
[표 26-2]
[표 27-1]
[표 27-2]
[표 28-1]
[표 28-2]
본 발명의 살균성 조성물은, 우수한 상승 효과를 나타내고, 특히 농원예용 식물을 침범하는 병원균에 대하여 우수한 효과를 나타내기 때문에, 신규의 살균성 조성물로서 매우 유용하고, 산업상의 이용 가능성을 갖는다.
Claims (9)
- (a) 4-[4-(6-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘,
4-[4-(6-플루오로-9-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[5-메틸-3-(트리플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘,
4-[4-(6-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘, 및
4-[4-(6-플루오로-9-메틸술포닐옥시-1,5-디하이드로-3H-2,4-벤조디옥세핀-3-일)-2-티아졸릴]-1-[2-[3,5-비스(디플루오로메틸)-1H-피라졸-1-일]아세틸]피페리딘,
혹은 이들의 혼합물에서 선택되는 화합물, 그 에난티오머, 혹은 그들의 혼합물, 또는 그 농원예상 허용 가능한 염의 적어도 1 종과, (b) 농원예용 살균제 또는 그 염을 적어도 1 종을 포함하는 살균성 조성물. - 제 1 항에 있어서,
성분 (b) 가, 벤티아발리카르브, 발리페날레이트, 족사미드, 파목사돈, 이프로발리카르브, 페나미돈, 플루오피콜리드, 아메톡트라딘, 시아조파미드, 만디프로파미드, 메탈락실-M, 에타복삼, 디메토모르프, 시목사닐, 염기성 황산동, 클로로타로닐, 만제브, 프로피네브, 캡탄, 크레속심-메틸, 아족시스트로빈, 트리플록시스트로빈, 플루아지남, 피리벤카르브, 펜티오피라드, 퀴녹시펜, 피리오페논, 프로파모카르브, 포세틸-알루미늄, 이미녹타딘, 플루디옥소닐, 티오파네이트-메틸, 이프로디온, 테부코나졸, 시프로디닐, 아미술브롬, 트리시클라졸, 폴리옥신, 테부플로퀸, 프로피코나졸, 옥사티아피프롤린 또는 이들의 염에서 선택되는 적어도 1 종의 화합물을 포함하는, 살균성 조성물. - 제 1 항에 있어서,
농원예용 살균제로서 사용하는, 살균성 조성물. - 제 1 항에 기재된 성분 (a) 및 성분 (b) 를, 식물 또는 식물 주변의 영역에 처리하는 공정을 포함하고, 성분 (a) 및 성분 (b) 가 동시에, 연속해서, 또는 따로따로 처리되는, 식물 유해 생물의 방제 방법.
- 제 4 항에 있어서,
상기 처리가, 분무, 산포, 살분, 스프레이, 확산, 침지, 관주, 주입, 살수 (침수), 발포, 도포, 분의, 코팅, 분사, 훈증, 훈연, 연무 및 도장으로 이루어지는 군에서 선택되는 적어도 1 개인, 식물 유해 생물의 방제 방법. - 제 4 항에 있어서,
상기 식물 주변의 영역이, 토양, 논, 수경 재배의 물, 및 재배 자재로 이루어지는 군에서 선택되는 적어도 1 개인, 식물 유해 생물의 방제 방법. - 제 4 항 내지 제 6 항 중 어느 한 항에 있어서,
성분 (b) 가, 벤티아발리카르브, 발리페날레이트, 족사미드, 파목사돈, 이프로발리카르브, 페나미돈, 플루오피콜리드, 아메톡트라딘, 시아조파미드, 만디프로파미드, 메탈락실-M, 에타복삼, 디메토모르프, 시목사닐, 염기성 황산동, 클로로타로닐, 만제브, 프로피네브, 캡탄, 크레속심-메틸, 아족시스트로빈, 트리플록시스트로빈, 플루아지남, 피리벤카르브, 펜티오피라드, 퀴녹시펜, 피리오페논, 프로파모카르브, 포세틸-알루미늄, 이미녹타딘, 플루디옥소닐, 티오파네이트-메틸, 이프로디온, 테부코나졸, 시프로디닐, 아미술브롬, 트리시클라졸, 폴리옥신, 테부플로퀸, 프로피코나졸, 옥사티아피프롤린 또는 이들의 염에서 선택되는 적어도 1 종의 화합물을 포함하는, 식물 유해 생물의 방제 방법. - 삭제
- 삭제
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EP3415008A1 (en) | 2018-12-19 |
EP3415008A4 (en) | 2019-09-11 |
AU2016392652B2 (en) | 2021-01-21 |
CN108601353A (zh) | 2018-09-28 |
JPWO2017138069A1 (ja) | 2018-11-29 |
AR107545A1 (es) | 2018-05-09 |
PH12018501543A1 (en) | 2019-06-03 |
CN108601353B (zh) | 2024-04-05 |
US11903387B2 (en) | 2024-02-20 |
AU2016392652A1 (en) | 2018-08-09 |
WO2017138069A1 (ja) | 2017-08-17 |
JP6649967B2 (ja) | 2020-02-19 |
US20210045386A1 (en) | 2021-02-18 |
KR20180105718A (ko) | 2018-09-28 |
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