JPS6168470A - Carbamoylimidazole derivative, its production and agricultural an horticultural fungicide - Google Patents
Carbamoylimidazole derivative, its production and agricultural an horticultural fungicideInfo
- Publication number
- JPS6168470A JPS6168470A JP59188778A JP18877884A JPS6168470A JP S6168470 A JPS6168470 A JP S6168470A JP 59188778 A JP59188778 A JP 59188778A JP 18877884 A JP18877884 A JP 18877884A JP S6168470 A JPS6168470 A JP S6168470A
- Authority
- JP
- Japan
- Prior art keywords
- lower alkyl
- formula
- alkyl group
- general formula
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- NMIZONYLXCOHEF-UHFFFAOYSA-N 1h-imidazole-2-carboxamide Chemical class NC(=O)C1=NC=CN1 NMIZONYLXCOHEF-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 230000000855 fungicidal effect Effects 0.000 title claims abstract description 13
- 239000000417 fungicide Substances 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 29
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 150000002460 imidazoles Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 7
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 30
- 201000010099 disease Diseases 0.000 abstract description 29
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- 238000002360 preparation method Methods 0.000 abstract description 6
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- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 241000233622 Phytophthora infestans Species 0.000 abstract description 2
- 240000007594 Oryza sativa Species 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 230000001276 controlling effect Effects 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
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- 239000000463 material Substances 0.000 abstract 1
- -1 furoyl Chemical group 0.000 description 29
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
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- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 241001330975 Magnaporthe oryzae Species 0.000 description 1
- 206010027146 Melanoderma Diseases 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241000231139 Pyricularia Species 0.000 description 1
- 241000221662 Sclerotinia Species 0.000 description 1
- 241001558929 Sclerotium <basidiomycota> Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
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- 239000003443 antiviral agent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 244000000005 bacterial plant pathogen Species 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- VNSBYDPZHCQWNB-UHFFFAOYSA-N calcium;aluminum;dioxido(oxo)silane;sodium;hydrate Chemical compound O.[Na].[Al].[Ca+2].[O-][Si]([O-])=O VNSBYDPZHCQWNB-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- SHFGJEQAOUMGJM-UHFFFAOYSA-N dialuminum dipotassium disodium dioxosilane iron(3+) oxocalcium oxomagnesium oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[Na+].[Na+].[Al+3].[Al+3].[K+].[K+].[Fe+3].[Fe+3].O=[Mg].O=[Ca].O=[Si]=O SHFGJEQAOUMGJM-UHFFFAOYSA-N 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
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- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
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- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002826 nitrites Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 150000004045 organic chlorine compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002898 organic sulfur compounds Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
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- 125000005359 phenoxyalkyl group Chemical class 0.000 description 1
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- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 description 1
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
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- 230000002194 synthesizing effect Effects 0.000 description 1
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- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000012749 thinning agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
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- 229940116362 tragacanth Drugs 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は新規なカルバモイルイミダゾール誘導体、その
製法及び農園芸用殺菌剤に関する。更に詳しくは、本発
明は下記式（Ｉ）で表わされるカルバモイルイミダゾー
ル誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel carbamoylimidazole derivative, a method for producing the same, and a fungicide for agricultural and horticultural use. More specifically, the present invention relates to a carbamoylimidazole derivative represented by the following formula (I).
一般式：
式中、Ｒ１は低級アルキル基、低級アルコキシ−低級ア
ルキル基又は炭素数３〜８のシクロアルキル基を示し、
Ｒ’はフルオル置換−低級アルキル基を示し、
Ｘは酸素原子又はイオウ原子を示し、
Ｙはハロゲン原子又は低級アルキル基を示し、
ｍは０．１又は２を示し、そして
ｎは２．３．４．５又は６を示す。General formula: In the formula, R1 represents a lower alkyl group, a lower alkoxy-lower alkyl group, or a cycloalkyl group having 3 to 8 carbon atoms, R' represents a fluoro-substituted lower alkyl group, and X is an oxygen atom or a sulfur atom. , Y represents a halogen atom or a lower alkyl group, m represents 0.1 or 2, and n represents 2.3.4.5 or 6.
上記一般式（Ｉ）の化合物は、例えば下記の方法によシ
製造することができ、本発明は斯る製法にも、関する。The compound of general formula (I) above can be produced, for example, by the method described below, and the present invention also relates to such a production method.
製法１）ニー
一般式：
式中、Ｒ” 、Ｘ、ＹＸｍ及びｎは前記と同じ、そして
Ｈａｌはハロゲン原子を示す、
で表わされる化合物と、
一般式：
％式％（［）
式中、Ｒ′は前記と同じ、
で表わされる化合物とを反応させ、次いで、Ｎ、Ｎ’−
力ルボニルジイミダゾールを反応させることを特徴とす
る前記一般式（Ｉ）のカルバモイルイミダゾール誘導体
の製造方法。Production method 1) General formula: In the formula, R'', X, YXm and n are the same as above, and Hal represents a halogen atom. ' is the same as above, react with the compound represented by, then N, N'-
A method for producing a carbamoylimidazole derivative of the general formula (I), which comprises reacting carbamoylimidazole with carbamoylimidazole.
また本発明は前記一般式（１）のカルバモイルイミダゾ
ール誘導体を有効成分として含有する農園芸用殺菌剤に
も関する。The present invention also relates to an agricultural and horticultural fungicide containing the carbamoylimidazole derivative of the general formula (1) as an active ingredient.
本願出願日前公知の刊行物、特開昭５０−３１０４７号
公報明細書には、
一般式：
％式％
式中、Ｘは酸素又はイオウ、
Ｒ１は場合によジ置換されているア
ルキル基、・・・・・
Ｒ１は場合によジ置換されているフ
ェノキシアルキル基、・・・・・
で表わされる化合物を包含する化合物が殺かび活性を有
する旨、記載されている。A publication known before the filing date of the present application, JP-A-50-31047, describes the general formula: % formula % where X is oxygen or sulfur, R1 is an optionally di-substituted alkyl group, ... R1 is an optionally di-substituted phenoxyalkyl group, ... It is described that compounds including compounds represented by the following have fungicidal activity.
そして、上記式囚の一般式に、本発明の一般式（１）は
概念上、包含されるものである。The general formula (1) of the present invention is conceptually included in the above general formula.
然しなから、該公報明細書中には、本発明の前記一般式
（Ｉ）で特定された化合物において、上記式は、概念上
、包含されるが、該基に関して具体的記載がなされてい
ないのはもちろんのこと、そのような基を示唆する記載
も全く存在しない。 ゛本発明者等は各種作物病に対し
、優れた防除活性を有する新規化合物を創製すべく、合
成並びに生物活性スクリニングを行なった結果、比変、
前記一般式（１）で表わされるカルノくモイルイミダゾ
ール誘導体を合成することに成功し、そして、該化合物
が、後に詳しく述べる如く、上記引例公報明細書記載の
化合物に比較し、低薬量で、完壁な防除効果を発現する
ことを発見した。本発明は斯る発見に基づき、完成され
たものである。However, in the specification of the publication, in the compound specified by the general formula (I) of the present invention, the above formula is conceptually included, but there is no specific description regarding the group. Of course, there is no description that suggests such a group.゛The present inventors performed synthesis and biological activity screening to create new compounds with excellent control activity against various crop diseases.
We have succeeded in synthesizing the carnocumoylimidazole derivative represented by the general formula (1), and as will be described in detail later, the compound has a lower dosage than the compound described in the specification of the cited publication, It was discovered that it has a perfect pest control effect. The present invention has been completed based on this discovery.
本発明者等によう、得られた知見によれば、詳しくは、
本発明一般式（Ｉ）の化合物は、前記の如く、本願出願
日前公知の特開昭５０−３１０４７号公報明細書記載の
一般式囚の化合物に、概念上、包含されるものである。According to the findings obtained by the present inventors, in detail,
As mentioned above, the compound of the general formula (I) of the present invention is conceptually included in the compounds of the general formula described in the specification of JP-A-50-31047, which was known before the filing date of the present application.
然しなかも、該公報明細書中には、本発明で特定された
一般式（１）において、その最大の特徴であ般的開示及
び具体的記載はもちろんのこと、何等の示唆もなされて
いない。However, in the specification of the publication, there is no general disclosure or specific description of the most important feature of the general formula (1) specified in the present invention, nor any suggestion whatsoever. .
即ち、本発明一般式（Ｉ）で特定された基：−Ｘ−Ｒ”
Ｋ対応する上記公報明細書中での具体的記載は、ハロゲ
ン原子、アルコキシ基、アルキル基、トリハロメチル基
、シアノ基、アルキルチオ基、ニトロ基、アルキルスル
ホニル基、アセチル基、アセドア、ミド基、アミノ基、
ジアルキルアミノ基よシ選ばれるもののみである。That is, the group specified by the general formula (I) of the present invention: -X-R"
K The specific descriptions in the corresponding specifications of the above publication include halogen atoms, alkoxy groups, alkyl groups, trihalomethyl groups, cyano groups, alkylthio groups, nitro groups, alkylsulfonyl groups, acetyl groups, acedoa, mido groups, amino basis,
Only dialkylamino groups are selected.
そして、本発明一般式（１）の化合物は、上記公報明細
書記載の化合物に比較し、後に挙げる生物試験実施例で
例証される通シ、植物病に対して、比較化合物が効果を
現わすことのできない低薬量濃度で極めて優れた殺菌活
性を維持し、且つ、全く予想外、且つ驚くべき完壁な防
除効力を発現するユニークな化合物である。Comparing the compound of the general formula (1) of the present invention with the compound described in the specification of the above-mentioned publication, the comparative compound exhibits effects against common plant diseases as illustrated in the biological test examples listed later. It is a unique compound that maintains extremely excellent bactericidal activity at extremely low drug concentrations and exhibits completely unexpected and surprising control efficacy.
本発明化合物唸、例えば、イネいもち病、イネごま葉枯
病、トマトの疫病、キュウリの炭そ病、キュウリのうど
んこ病、イネ馬鹿苗病に対して、上記公報明細書記載の
化合物に比較し、極めて優れた予想外且つ驚くべき防除
効力を発現する。Comparison of the compounds of the present invention against, for example, rice blast, rice sesame leaf blight, tomato late blight, cucumber anthracnose, cucumber powdery mildew, and rice bakanae disease compared to the compounds described in the above-mentioned publication specifications. It exhibits extremely excellent, unexpected and surprising pesticidal efficacy.
Ｑ＜て、本発明者等の研究によれば、特開昭５０−３１
０４７号が具体的開示も示唆もしていない式（１）の化
合物は、前記式囚に概念上、包含され得るものであるに
もかかわらず、該公報明細書で言及しなかった低薬量で
全く予想外且つ驚くべき優れた殺菌効力を発現するとい
う、該公報明細書で全く認識されなかった新たな技術的
効果を達成する化合物であることがわかった。Q<According to the research of the present inventors, JP-A-50-31
Although the compound of formula (1), which No. 047 does not specifically disclose or suggest, can conceptually be included in the above-mentioned formula compound, it is not mentioned in the specification of the publication at a low dose. It has been found that this compound achieves a new technical effect that was completely unrecognized in the specification of the publication, that is, it exhibits a completely unexpected and surprisingly excellent bactericidal effect.
従って、本発明の目的は、前記一般式（Ｉ）のカルバモ
イルイミダゾール誘導体、その製法及び農園芸用殺菌剤
としての利用を提供するにある。Therefore, an object of the present invention is to provide a carbamoylimidazole derivative of the general formula (I), a method for producing the same, and its use as a fungicide for agriculture and horticulture.
本発明の上記目的及び更に多くの他の目的並びに利点は
以下の記載から一層明らかとなるであろう。The above objects and many other objects and advantages of the present invention will become more apparent from the following description.
本発明化合物は農園芸上の作物のみならず、一般の植物
に対し、薬害を生じさせることなく、広範な植物病原菌
に対し、低薬量で、強い殺菌力を有し、広範な植物病害
防除に適用することができる。The compound of the present invention has strong bactericidal activity against a wide range of plant pathogenic bacteria at low doses, and can control a wide range of plant diseases, not only on agricultural and horticultural crops but also on general plants. It can be applied to
本発明化合物の殺菌スペクトルは例えば、古生菌〔アー
キミセテス（Ａｒｃｈｉｍｙｃｅｔｅｓ）：ｌ、藻菌〔
フイコミセテス（ｐｈｙｃｏｍｙｃｅｔｅｓ）］、子の
う菌〔アスコミセテス（Ａｓｃｏｍｙｃｅｔｅｓ）］、
担子菌［バシジオミセテス（Ｂａｓｉｄｉｏｍｙｃｅｔ
ｅｓ）］ 、不完全薗〔フンギ・イムパーツエフティ（
ＦｕｎｇｉＩｍｐｅｒｆｅｃｔｉ） ］、その他細菌類
による種々の植物病害に対して有効に使用できる。The bactericidal spectrum of the compound of the present invention is, for example, for archaeal bacteria [Archimycetes: l, algae [
phycomycetes], ascomycetes [Ascomycetes],
Basidiomycetes [Basidiomycetes]
es)], Imparte Sono [Fungi Imparts
[Fungi Imperfecti]] and various other plant diseases caused by bacteria.
そして、本発明化合物の殺菌スペクトルの代表例として
は、イネのいもち病（ＰｙｒｉｃｕｌａｒｉａＯｒ）’
ｚａｅ）、イネのごま葉枯病（Ｏｐｈｉｏｂｏｌｕｓｍ
ｉｙａｂｅａｎｕｓ）、イネの馬鹿苗病（Ｑｉｂｂｅｒ
ｅｌｌａｆｕｊｉｋｕｒｏｊ）、各種作物の菌核病（ｓ
ｃｌｅｒｏ−ｔｉｎｆａ ｓｃｌｅｒｏｔｉｏｒｕｍ）
、黒斑病（Ａｌ ｔ ｅ ｒｎ ａ−ｒｉａ ｂｒａｓ
ｓｉｃａｅ）、うどんこ病（Ｓｐｈａｅｒｏ−ｔｈｅｃ
ａ ｆｕｌｉｇｉｎｅａ）、灰色かび病（Ｂｏｔｒｙｔ
ｉｓｃｉｎｅｒｅａ）、ウリ類の炭そ病（Ｃｏｌｌｅｔ
ｏｔｒｉ−ｃｈｕｍ ｌａｇｅｎａｒｉｕｍ）、トマト
等の疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ ｊｎｆｅｓｔ
ａｎｓ）等を例示することができる。As a representative example of the fungicidal spectrum of the compound of the present invention, rice blast disease (Pyricularia Or')
zae), sesame leaf blight of rice (Ophiobolusm
iyabeanus), Qibber disease of rice
ellafujikuroj), sclerotium (sclerotinia) of various crops
clero-tinfa sclerotiorum)
, black spot disease
sicae), powdery mildew (Sphaero-thec
a fuliginea), gray mold (Botryt
iscinerea), anthracnose of cucurbits (Collet
otri-chum lagenarium), late blight of tomatoes, etc. (Phytophthora jnfest)
ans), etc.
本発明の一般式（１）の化合物は、例えば下記の方法に
よシ、容易に製造することができる。The compound of general formula (1) of the present invention can be easily produced, for example, by the following method.
製法１）：一
式中、Ｒ” 、Ｒ” 、Ｘ、 Ｙ、 ｍ、 ｎ及びＨａ
ｌは前記と同じ。Manufacturing method 1): In the set, R'', R'', X, Y, m, n and Ha
l is the same as above.
上記反応式にシいて、Ｒ１は具体的にはメチル、エチル
、フロビル、イソプロピル、ｎ−（ｉｓｏ−１ｓｅｃ
−又はｔｅｒｔ−）ブチル等の低級アルキル基、上記例
示と同様の低級アルキル基を有する低級アルコキシ−低
級アルキル基又はシクロプロピル、゛シクロブチル、シ
クロペンチル、シクロヘキシル、シクロヘプチルの炭素
数３〜８のシクロアルキル基を示し、
Ｒ１は、フルオル置換−低級アルキル基を示し、具体的
には、トリフルオロメチル、２，２．２−トリフルオル
エチル等を例示することができ、Ｘは酸素原子又はイオ
ウ原子を示し、
Ｙは具体的にはフルオル、クロル、ヨード、ブロムのハ
ロゲン原子又は上記例示と同様の低級アルキル基を示し
、
ｍは０，１又は２を示し、
ｎは２．３．４．５又は６を示し、そしてＨＩＬＬは上
記例示と同様のハロゲン原子を示し、好ましくはクロル
又はブロムを示す。In the above reaction formula, R1 specifically represents methyl, ethyl, furoyl, isopropyl, n-(iso-1sec
- or tert-) butyl, a lower alkoxy-lower alkyl group having the same lower alkyl group as exemplified above, or a cycloalkyl group having 3 to 8 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl. R1 represents a fluoro-substituted lower alkyl group, specific examples include trifluoromethyl, 2,2,2-trifluoroethyl, etc., and X represents an oxygen atom or a sulfur atom. Y specifically represents a halogen atom such as fluoro, chloro, iodo, or bromine, or a lower alkyl group as exemplified above, m represents 0, 1, or 2, and n represents 2.3.4.5 or 2.3.4.5 or 6, and HILL represents the same halogen atom as in the above example, preferably chloro or bromine.
上記反応式で示される本発明化合物の製法において、原
料である一般式（ＩＩ）の化合物の異体例としては、例
えば、
２−（４−（２、２、２−トリフルオロエチルチオ）フ
ェノキシフエチルブロマイド、２−（４−（２，２，２
−）リフルオロエチルチオ）−２−トロキシ〕エチルブ
ロマイド、２−［４−（２，２，２−）リフルオロエチ
ルチオ）−３、５−キシロキシ〕エチルブロマイド、２
−〔２−クロロ−４−（２，２ｊ２−トリフルオロエチ
ルチオ）フェノキシフエチルブロマイド、
２−Ｃ２、６−ジクロロ−４−（２，２，２−トリフル
オロエチルチオ）フェノキシフエチルブロマイド、
３−Ｃ４−（２、２、２−トリフルオロエチルチオ）フ
ェノキシフプロピルブロマイド、３−（２，６−ジクロ
ロ−４−（２，２，２−トリフルオロエチルチオ）フェ
ノキシフプロピルブロマイド、
４−〔４−（２、２、２−）リフルオロエチルチオ）フ
ェノキシコブチルブロマイド、４−Ｃ４−（２，２，２
−トリフルオロエチルチオ）−２−トロキシコブチルブ
ロマイド、４−（４−（２，２，２−トリフルオロエチ
ルチオ）−３，５−キシロキシコブチルブロマイド、４
−〔２−クロロ−４−（２，２，２−１リフルオロエチ
ルチオ）フェノキシコブチルブロマイド、
５−（４−（２，２，２−トリフルオロエチルチオ）フ
ェノキシ〕ペンチルブロマイド、５−（２，６−ジクロ
ロ−４−（２，２，２−トリフルオロエチルチオ）フェ
ノキシ〕ペンチルブロマイド、
６−［：４−（２，２，２−トリフルオロエチルチオ）
フェノキシ〕ヘキシルブロマイド、２−（４−トリフル
オロメチルチオフェノ牛シ）エチルブロマイド、
２−（２−クロロ−４−１リフルオロメチルチオフエノ
キシ）エチルブロマイド、
２−（２，６−ジクロｌ：ｌ−４−）リフルオロメチル
チオフェノキシ）エチルブロマイド、３−（４−）リフ
ルオロメチルチオフェノキシ）プロピルブロマイド、
３−（２−クロロ−４−トリフルオロメチルチオフェノ
キシ）プロピルブロマイド、
３−（２，６−ジクロロ−４−トリフルオロメチルチオ
フェノキシ）プロピルブロマイド、４−（４−）リフル
オロメチルチオフェノキシ）ブチルブロマイド、
４−（２−クロロ−４−トリフルオロメチルチオフェノ
キシ）ブチルブロマイド、
５−（４−トリフルオロメチルチオフェノキシ）ペンチ
ルブロマイド、
５−（２−クロロ−４−トリフルオロメチルチオフェノ
キシ）ペンチルブロマイド、
５−（２，６−ジクロロ−４−トリフルオロメチルチオ
フェノキシ）ペンチルブロマイド、２−（４−） ！Ｊ
フルオロメトキシフェノキシ）エチルブロマイド、
２−（２−クロロ−４−トリフルオロメトキシフェノキ
シ）エチルブロマイド、
２−（２，６−ジクロロ−４−トリフルオロメトキシフ
ェノキシ）エチルブロマイド、３−（４−）リフルオロ
メトキシフェノキシ）プロピルブロマイド、
３−（２−クロロ−４−トリフルオロメトキシフェノキ
シ）プロピルブロマイド、
３−（２，６−ジクロロ−４−トリフルオロメトキシフ
ェノキシ）プロピルブロマイド、５−（４−トリフルオ
ロメトキシフェノキシ）ペンチルブロマイド、
５−（２−クロロ−４−トリフルオロメトキシフェノキ
シ）ペンチルブロマイド、
５−（２，６−ジクロロ−４−トリフルオロメトキシフ
ェノキシ）ペンチルブロマイド等を例示することができ
、またブロマイド体の代わ）にそれらのクロライド体も
挙げることができる。In the method for producing the compound of the present invention represented by the above reaction formula, examples of isomers of the compound of general formula (II) as a raw material include, for example, 2-(4-(2,2,2-trifluoroethylthio)phenoxif Ethyl bromide, 2-(4-(2,2,2
-)lifluoroethylthio)-2-troxy]ethyl bromide, 2-[4-(2,2,2-)lifluoroethylthio)-3,5-xyloxy]ethyl bromide, 2
-[2-chloro-4-(2,2j2-trifluoroethylthio)phenoxyphethyl bromide, 2-C2,6-dichloro-4-(2,2,2-trifluoroethylthio)phenoxyphethyl bromide, 3-C4-(2,2,2-trifluoroethylthio)phenoxyfupropyl bromide, 3-(2,6-dichloro-4-(2,2,2-trifluoroethylthio)phenoxyfupropyl bromide, 4 -[4-(2,2,2-)lifluoroethylthio)phenoxycobutyl bromide, 4-C4-(2,2,2
-trifluoroethylthio)-2-troxycobutyl bromide, 4-(4-(2,2,2-trifluoroethylthio)-3,5-xyloxycobutyl bromide, 4
-[2-chloro-4-(2,2,2-1-trifluoroethylthio)phenoxycobutyl bromide, 5-(4-(2,2,2-trifluoroethylthio)phenoxy]pentyl bromide, 5- (2,6-dichloro-4-(2,2,2-trifluoroethylthio)phenoxy]pentyl bromide, 6-[:4-(2,2,2-trifluoroethylthio)
phenoxy]hexyl bromide, 2-(4-trifluoromethylthiophenoxy)ethyl bromide, 2-(2-chloro-4-1lifluoromethylthiophenoxy)ethyl bromide, 2-(2,6-dichlorol): l-4-)lifluoromethylthiophenoxy)ethyl bromide, 3-(4-)lifluoromethylthiophenoxy)propyl bromide, 3-(2-chloro-4-trifluoromethylthiophenoxy)propyl bromide, 3-(2,6) -dichloro-4-trifluoromethylthiophenoxy)propyl bromide, 4-(4-)lifluoromethylthiophenoxy)butyl bromide, 4-(2-chloro-4-trifluoromethylthiophenoxy)butyl bromide, 5-(4-trifluoromethylthiophenoxy)butyl bromide, Fluoromethylthiophenoxy)pentyl bromide, 5-(2-chloro-4-trifluoromethylthiophenoxy)pentyl bromide, 5-(2,6-dichloro-4-trifluoromethylthiophenoxy)pentyl bromide, 2-(4-)! J
Fluoromethoxyphenoxy)ethyl bromide, 2-(2-chloro-4-trifluoromethoxyphenoxy)ethyl bromide, 2-(2,6-dichloro-4-trifluoromethoxyphenoxy)ethyl bromide, 3-(4-)ly Fluoromethoxyphenoxy)propyl bromide, 3-(2-chloro-4-trifluoromethoxyphenoxy)propyl bromide, 3-(2,6-dichloro-4-trifluoromethoxyphenoxy)propyl bromide, 5-(4-trifluoro Examples include methoxyphenoxy)pentyl bromide, 5-(2-chloro-4-trifluoromethoxyphenoxy)pentyl bromide, 5-(2,6-dichloro-4-trifluoromethoxyphenoxy)pentyl bromide, and the like. In place of the bromide form, their chloride form can also be mentioned.
同様に原料である一般式儂）の化合物の具体例としては
、例えば、
メチルアミン、
エチルアミン、
ｎ−プロピルアミン、
イソプロピルアミン、
ｎ−ブチルアミン、
５ｅａ−ブチルアミン、
２−エトキシエチルアミン、
シクロペンチルアミン、
シクロヘキシルアミン
等を例示することができる。Specific examples of the compounds of the general formula (2) which are also raw materials include, for example, methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, 5ea-butylamine, 2-ethoxyethylamine, cyclopentylamine, cyclohexylamine. etc. can be exemplified.
次に代表例を示し、上記製法を具体的に説明する。Next, a representative example will be shown and the above manufacturing method will be specifically explained.
本発明式（１）化合物の上記製法Ｉ）は、望ましくは溶
媒または希釈剤を用いて実施できる。このためにはすべ
ての不活性溶媒、希釈剤を使用することができる。The above method I) for producing the compound of formula (1) of the present invention can be carried out desirably using a solvent or a diluent. All inert solvents and diluents can be used for this purpose.
かかる溶媒ないし希釈剤としては、水、脂肪族、環脂肪
族および芳香族炭化水素類（場合によっては塩素化され
てもよい）例えば、ヘキサン、シクロへキサン、石油エ
ーテル、リグロイン、ベンゼン、トルエン、キシレン、
メチレンクロライド、クロロホルム、四塩化炭素、エチ
レンクロライドおヨヒトリクロロエチレン、クロロベン
ゼン；そ−の他、エーテル類例えば、ジエチルエーテル
、メチルエチルエーテル、ジー１ＳＯ−プロピルエーテ
ル、ジブチルエーテル、ジオキサン、テトラヒドロフラ
ン；ケトン類例−２ばアセトン、メチルエチルケトン、
メチル−１ｓｏ−プロピルケトン、メチル−１ｓｏ−ブ
チルケトン； ニトリル類例えば、アセトニトリル、プ
ロピオニトリル、アクリロニトリル；アルコール類例え
ば、メタノール、エタノール、１ｓｏ−７’ロバノール
、ブタノール、 エチレングリコール；エステル類例え
ば、酢酸エチル、酢酸アミル；酸アミド類例えば、ジメ
チルホルムアミド、ジメチルアセトアミド；スルホン、
スルホキシド類例えば、ジメチルスルホキシド、スルホ
ラン；および塩基例えば、ピリジン等をあげることがで
きる。Such solvents or diluents include water, aliphatic, cycloaliphatic and aromatic hydrocarbons (which may optionally be chlorinated) such as hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene,
Methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichloroethylene, chlorobenzene; Other ethers, such as diethyl ether, methyl ethyl ether, di-1SO-propyl ether, dibutyl ether, dioxane, tetrahydrofuran; Ketones example 2 acetone, methyl ethyl ketone,
Methyl-1so-propyl ketone, methyl-1so-butylketone; Nitriles such as acetonitrile, propionitrile, acrylonitrile; Alcohols such as methanol, ethanol, 1so-7' lovanol, butanol, ethylene glycol; Esters such as ethyl acetate , amyl acetate; acid amides such as dimethylformamide, dimethylacetamide; sulfone,
Mention may be made of sulfoxides such as dimethyl sulfoxide, sulfolane; and bases such as pyridine.
また上記したように本発明の反応は酸結合剤の存在下で
行うことができる。かかる酸結合剤としては、普通一般
に用いられているアルカリ金属の水酸化物、炭酸塩、重
炭酸塩およびアルコラ°−ト等や、第３級アミン類例え
ば、トリエチルアミン、ジエチルアニリン、ピリジン等
をあげることができる。Furthermore, as described above, the reaction of the present invention can be carried out in the presence of an acid binder. Examples of such acid binders include commonly used alkali metal hydroxides, carbonates, bicarbonates, alcoholates, etc., and tertiary amines such as triethylamine, diethylaniline, pyridine, etc. be able to.
上記方法は、広い温度範囲内において実施することがで
きる。一般には約−２０℃と混合物の沸点との間で実施
でき、望ましくはＯ〜約１００℃の間で実施できる。ま
た、反応は常圧の下でおこなうのが望ましいが、加圧ま
たは減圧下で操作することも可能である。The above method can be carried out within a wide temperature range. Generally it can be carried out between about -20<0>C and the boiling point of the mixture, preferably between 0 and about 100<0>C. Further, although it is preferable to carry out the reaction under normal pressure, it is also possible to operate under increased pressure or reduced pressure.
上記製法１）は、中間生成物の一般式（ＩＴ）の化合物
を分離し、行なうこともでき、また分離せずに、連続反
応によシ行なうこともできる。The above production method 1) can be carried out after separating the compound of general formula (IT) as an intermediate product, or can be carried out by continuous reaction without separation.
本発明化合物は別法として、下記反応式で示される方法
によっても製造することができる。Alternatively, the compound of the present invention can also be produced by the method shown in the following reaction formula.
別法ニ一
式中、Ｒ１、Ｒ” 、Ｘ％ ＹＮ ｍ及びｎは前記と同
じ、
Ｍは水素原子又はアルカリ金属原子を示す。In the alternative formula D, R1, R'', X% YN m and n are the same as above, M represents a hydrogen atom or an alkali metal atom.
上記反応式において、ホスゲン（ｃｏｃｌ、）の代わシ
にトリクロロメチルクロロホルメート（ｃｌ、Ｃ０ＣＯ
ＣＩ）を反応させることもできる。In the above reaction formula, trichloromethyl chloroformate (cl, COCO) is substituted for phosgene (cocl, ).
CI) can also be reacted.
本発明の式（Ｉ）化合物を、農園芸用殺菌剤として使用
する場合、そのｉｔ直接水で希釈して使用するか、また
は農薬補助剤を用いて農薬製造分野に於て一般に行なわ
れている方法により、種々の製剤形態にして使用するこ
とができる。これらの種種の製剤は、実際の使用に際し
ては、直接そのまま使用するか、または水で所望濃度に
希釈して使用することができる。ここに言う、農薬補助
剤としては、例えば、希釈剤（溶剤、増量剤、担体）、
界面活性剤（可溶化剤、乳化剤、分散剤、湿展剤）、安
定剤、固着剤、エーロゾル用噴射剤、共力剤を挙げるこ
とができる。When the compound of formula (I) of the present invention is used as a fungicide for agriculture and horticulture, it can be used by directly diluting it with water, or by using a pesticide auxiliary, which is generally done in the field of pesticide manufacturing. Depending on the method, it can be used in various formulation forms. In actual use, these various preparations can be used directly or diluted with water to a desired concentration. Examples of pesticide adjuvants mentioned here include diluents (solvents, fillers, carriers),
Mention may be made of surfactants (solubilizers, emulsifiers, dispersants, wetting agents), stabilizers, sticking agents, propellants for aerosols, synergists.
溶剤としては、水のほかに有機溶剤を例示でき、例えば
、炭化水素類〔例えば、ｎ−ヘキサン、石油エーテル、
ナフサ、石油留分（パラフィン蝋、灯油、軽油、中油、
重油）、ベンゼン、トルエン、キシレン類〕；ハロゲン
化炭化水素類〔例えば、クロロメチレン、四塩化炭素、
トリクロロエチレン１、エチレンクロライド、二夷化エ
チレン、クロロベンゼン、クロロホルム〕；アルコール
Ｗ４ Ｃ例エバ、メチルアルコール、エチルアルコール
、フロビルアルコール、エチレングリコール〕；エーテ
ル類〔例えば、エチルエーテル、エチレンオキシド、ジ
オキサン〕：アルコールエーテル類〔例エバ、エチレン
グリコールモノメチルエーテル〕；ケトン類〔例えば、
アセトン、イソホロン〕：エステル類〔例えば、酢酸エ
チル、酢酸アルキルアミン類〔例えば、ジメチルホルム
アミド、ジメチルアセトアミド〕；スルホキシド類〔例
えば、゛ジメチルスルホキシド〕；などを挙げることが
できる。Examples of the solvent include organic solvents in addition to water, such as hydrocarbons [e.g., n-hexane, petroleum ether,
Naphtha, petroleum distillates (paraffin wax, kerosene, light oil, medium oil,
heavy oil), benzene, toluene, xylenes]; halogenated hydrocarbons (e.g. chloromethylene, carbon tetrachloride,
Trichlorethylene 1, ethylene chloride, ethylene dichloride, chlorobenzene, chloroform]; Alcohol W4 C example Eva, methyl alcohol, ethyl alcohol, flobyl alcohol, ethylene glycol]; Ethers [e.g., ethyl ether, ethylene oxide, dioxane]: Alcohol Ethers [e.g. Eva, ethylene glycol monomethyl ether]; Ketones [e.g.
Acetone, isophorone]; Esters [eg, ethyl acetate, alkyl acetate [eg, dimethylformamide, dimethylacetamide]; Sulfoxides [eg, dimethyl sulfoxide]; and the like.
増量剤または担体としては、たとえば、消石灰、マグネ
シウム石灰、石膏、炭酸カルシウム、珪石、パーライト
、軽石、方解石、珪藻土、無晶形酸化ケイ素、アルミナ
、ゼオライト、粘土鉱物（例えば、パイロフィライト、
滑石、モンモリロナイト、バイデライト、バーミキュラ
イト、カオリナイト、雲母）などの如き無機質粉粒体；
たとえば、穀粉、殿粉、加工デンプン、砂糖、ブドウ糖
、植物茎幹破砕物などの如き植物性粉粒体；たとえば、
フェノール樹脂、尿素樹脂、塩化ビニル樹脂などの如き
合成樹脂の粉粒体；を挙げることができる。Extending agents or carriers include, for example, slaked lime, magnesium lime, gypsum, calcium carbonate, silica, perlite, pumice, calcite, diatomaceous earth, amorphous silicon oxide, alumina, zeolite, clay minerals (e.g. pyrophyllite,
Inorganic powder particles such as talc, montmorillonite, beidellite, vermiculite, kaolinite, mica);
For example, vegetable powder such as grain flour, starch, modified starch, sugar, glucose, crushed plant stems, etc.;
Examples include powders of synthetic resins such as phenol resins, urea resins, vinyl chloride resins, and the like.
界面活性剤としては、アニオン（陰イオン）界面活性剤
、たとえば、アルキル硫酸エステル類〔例えばラウリル
硫酸ナトリウム〕、アリールスルホン酸類Ｃ例えばアル
キルアリールスルホン酸塩、アルキルナフタレンスルホ
ン酸ナトリウム〕、コハク酸塩類、ポリエチレングリコ
ールアルキルアリールエーテル硫酸エステル塩類；カチ
オン（陽イオン）界面活性剤、たとえば、アルキルアミ
ン類〔例えば、ラウリルアミン、ステアリルトリメチル
アンモニウムクロライド、アルキルジメチルベンジルア
ンモニウムクロライド〕、ポリオキシエチレンアルキル
アミン類；非イオン界面活性剤、たとえば、ポリオキシ
エチレングリコールエ ｆｋｆｆ４ｃ例えば、ポリオキ
シエチレンアルキルアリールエーテル、およびその縮合
物〕、ポリオキシエチレングリコールエステル類Ｃ例ｔ
ば、ポリオキシエチレン脂肪酸エステル〕、多価アルコ
ールエステル類〔例えば、ポリオ中ジエチレンソルビタ
ンモノラウレート〕；両性界面活性剤；等を挙げること
ができる。Examples of the surfactant include anionic surfactants such as alkyl sulfates [e.g., sodium lauryl sulfate], aryl sulfonic acids (e.g., alkylaryl sulfonate, sodium alkylnaphthalene sulfonate), succinates, Polyethylene glycol alkylaryl ether sulfate salts; cationic surfactants, such as alkylamines [such as laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride], polyoxyethylene alkylamines; nonionic Surfactants, such as polyoxyethylene glycol esters, polyoxyethylene alkylaryl ethers, and condensates thereof], polyoxyethylene glycol esters C example t
Examples include polyoxyethylene fatty acid ester], polyhydric alcohol esters [for example, diethylene sorbitan monolaurate in polio]; amphoteric surfactants; and the like.
その他、安定剤、固着剤〔例えば、農業川石゛けん、カ
ゼイン石灰、アルギン酸ソーダ、ポリビニルアルコール
Ｃｐ ｖ Ａ） 、酢酸ビニル系接着剤、アクリル系接
着剤〕、エーロゾル用噴射剤〔例えば、トリクロロフル
オロメタン、ジクロロフルオルメタン、１，２．２−）
シクロロー１．１．２−ト！Ｊフルオロエタン、クロロ
ベンゼン、ＬＮＧ。In addition, stabilizers, fixing agents [e.g., agricultural soap, casein lime, sodium alginate, polyvinyl alcohol CpvA), vinyl acetate adhesives, acrylic adhesives], propellants for aerosols [e.g., trichlorofluoromethane] , dichlorofluoromethane, 1,2.2-)
Cycloro 1.1.2-to! J fluoroethane, chlorobenzene, LNG.
低級エーテル〕；（燻煙剤用）燃焼調節剤〔例えば、亜
硝酸塩、亜鉛末、ジシアンジアミド〕：酸素供給剤〔例
えば、塩素酸塩〕：効力延長剤：分散安定剤〔例えば、
カゼイン、トラガント、カルボキシメチルセルロース（
ＣＭＣ）、ポリビニルアルコール（ＰＶＡ）：］：共力
剤を挙げることができる。Lower ethers]; Combustion modifiers (for smokers) [e.g. nitrites, zinc dust, dicyandiamide]; Oxygen supply agents [e.g. chlorates]; Potency extenders; Dispersion stabilizers [e.g.
casein, tragacanth, carboxymethyl cellulose (
CMC), polyvinyl alcohol (PVA): ]: synergist.
本発明の化合物は、一般に農薬製造分野で行なわれてい
る方法によ）種々の製剤形態に製造することができる。The compounds of the present invention can be manufactured into various formulations (by methods generally practiced in the agricultural chemical manufacturing field).
製剤の形態としては、乳剤：油剤：水和剤：水溶剤：懸
濁剤：粉剤２粒材４粒剤、燻煙剤：錠剤：煙霧剤：糊状
剤：カプセル剤等を挙げることができる。Examples of formulation forms include emulsions: oils, wettable powders, aqueous solutions, suspensions: 2 powders, 4 grains, smoking agents: tablets, atomizers, pastes, capsules, etc. .
本発明の農園芸用殺菌剤は、前記活性成分を例えば約０
．１〜約９５重量％、好ましくは約０．５〜約９０重量
％含有することができる。The agricultural and horticultural fungicide of the present invention contains, for example, about 0% of the active ingredient.
．． It can contain from 1 to about 95% by weight, preferably from about 0.5 to about 90% by weight.
実際の使用に際しては、前記した種々の製剤および散布
用調製物（ｒｅａｄｙ−ｔｏ−ｕｓｅ−ｐｒｅｐａｒａ
−ｔｉｏｎ） 中の活性化合物含量は、一般に約０．
０００１〜約２０重量％、好ましくは約０．００５〜約
１０重量−の範囲が適当である。In actual use, the various formulations and spray preparations described above are used.
-tion) is generally about 0.
A range of from about 0.0001 to about 20% by weight, preferably from about 0.005 to about 10% by weight, is suitable.
これら活性成分の含有量は、製剤の形態および施用する
方法、目的、時期、場所および病害の発生状況等によっ
て適当に変更できる。The content of these active ingredients can be appropriately changed depending on the form of the preparation, the method of application, purpose, timing, location, and disease occurrence situation.
本発明の化合物は、更に必要ならば、他の農薬、例えば
、殺虫剤、殺菌剤、殺ダニ剤、殺線虫剤、抗ウィルス剤
、除草剤、植物生長調整剤、誘引剤〔例えば、有機燐酸
エステル系化合物、カーバメート系化合物、ジチオ（ま
たはチオール）カーバメート系化合物、有機塩素系化合
物、ジニトロ系化合物、有機硫黄または金属系化合物、
抗生物質、置換ジフェニルエーテル系化合物、尿素系化
合物、トリアジン系化合物〕または／および肥料等を共
存させることもできる。The compounds of the present invention may also be used, if necessary, with other agricultural chemicals, such as insecticides, fungicides, acaricides, nematicides, antiviral agents, herbicides, plant growth regulators, attractants [e.g. Phosphoric ester compounds, carbamate compounds, dithio (or thiol) carbamate compounds, organochlorine compounds, dinitro compounds, organic sulfur or metal compounds,
Antibiotics, substituted diphenyl ether compounds, urea compounds, triazine compounds] or/and fertilizers can also be present.
本発明の前記活性成分を含有する種々の製剤または散布
用調整物（ｒｅａｄｙ−ｔｏ−ｕｓｅ−ｐｒｅｐａｒａ
−ｔｉｏｎ）は農薬製造分野にて通常一般に行なわれて
いる施用方法、散布、〔例えば液剤散布（噴霧）ミステ
ィング（ｍｉｓｔｉｎｇ）、アトマイズイング（ａｔｏ
ｍｉｚｉｎｇ）、散粉、散粒、水百施用、ボアリング（
ｐｏｕｒｉｎｇ） ］ ：燻煙：土壌施用、〔例えば、
混入、スプリンクリング（ｓｐｒｉｎｋｌｉｎｇ）、燻
蒸（ｖａｐｏｒｉｎｇ）、潅注〕二表面施用〔例えば、
塗布、巻付け（ｂｉｎｄｉｎｇ）、粉衣、被覆〕：浸漬
等によシ施用することができる。またいわゆる超高濃度
少量散布法（ｕｌ ｔｒａ−１ｏｗ−ｖｏｌｕｍｅ）に
よシ施用することもできる。この方法においては、活性
成分を１００チ含有することが可能である。Various formulations or ready-to-use preparations containing the active ingredients of the invention are available.
Application methods, spraying, spraying, misting, atomizing, etc., which are commonly used in the field of agricultural chemical manufacturing.
mizing), dusting, powdering, water application, boring (
pouring)] : Smoking: Soil application, [e.g.
mixing, sprinkleling, vaping, irrigation] dual surface application [e.g.
Application, binding, dressing, coating]: Can be applied by dipping, etc. It can also be applied by the so-called ultra-low-volume spraying method. In this way it is possible to contain 100 grams of active ingredient.
単位面積当シの施用量は適宜に選択でき、１ヘクタ一ル
当シ活性化合物として例えば約０．０３〜約１０ｋｇ、
好ましくは約０．１〜約６ｋｌ？ｌが例示できる。しか
しながら特別の場合には、これらの範囲を超えることが
、または下まわることが可能であシ、また時には必要で
さえある。The application amount per unit area can be selected as appropriate; for example, about 0.03 to about 10 kg of active compound per hectare,
Preferably about 0.1 to about 6 kl? An example is l. However, in special cases it may be possible, and sometimes even necessary, to exceed or fall below these ranges.
本発明によれば、活性成分として前記一般式（Ｉ）の化
合物を含み、且つ希釈剤（溶剤および／または増量剤お
よび／ｌたは担体）および／または界面活性剤、更に必
要ならば、例えば安定剤、固着剤、共力剤を含む農園芸
用殺菌組成物が提供できる。According to the invention, it comprises a compound of general formula (I) as an active ingredient, and also contains diluents (solvents and/or fillers and/or carriers) and/or surfactants, if necessary, e.g. An agricultural and horticultural fungicidal composition containing a stabilizer, a fixing agent, and a synergist can be provided.
更に、本発明によれば、病原菌および／またはその発生
並びに作物病の発生個所に前記一般式（■）の化合物を
単独に１または希釈剤（溶剤および／または増量剤およ
び／または担体）および／または界面活性剤、更に必要
ならば、安定剤、固着剤、共力剤とを混合して施用する
作物病防除方法が提供できる。Furthermore, according to the present invention, the compound of the general formula (■) is applied alone or to a diluent (solvent and/or filler and/or carrier) and/or to the site of pathogenic bacteria and/or their outbreak and crop disease. Alternatively, a method for controlling crop diseases can be provided in which a surfactant and, if necessary, a stabilizer, a fixing agent, and a synergist are mixed and applied.
次に実施例によ）本発明の内容を具体的に説明するが、
本発明はこれのみに限定されるべきものではない。Next, the content of the present invention will be specifically explained with reference to Examples.
The present invention should not be limited to this only.
実施例Ｌ
２−［２，６−ジクロロ−４−（２，２，２−トリフル
オロエチルチオ）フェノキシ〕エチルブロマイド（λ３
８ｆ）に、ｎ−プロピルアミン（５ｆ）を加え、室温で
８時間、還流下に３時間攪拌後、過剰のｎ−プロピルア
ミンを留去する。Example L 2-[2,6-dichloro-4-(2,2,2-trifluoroethylthio)phenoxy]ethyl bromide (λ3
N-propylamine (5f) was added to 8f), and after stirring at room temperature for 8 hours and under reflux for 3 hours, excess n-propylamine was distilled off.
残渣に水（２０ａｊ）、５％水酸化カリウム水溶液（２
０ｓｄ）及びトルエン（１０（１７）を加え、攪拌し、
有機層を分取する。有機層を水洗後、無水硫酸ナトリウ
ムで乾燥する。減圧下に低沸点物を留去して得られる残
渣（λ１６ｆ）はｎ ２０１．５２１０の屈折率を示す
Ｎ−（２−Ｃ２，６−ジクロロ−４−（２，２，２−ト
リフルオロエチルチオ）フェノキシ〕エチル）−Ｎ−プ
ロピルアミンであるが、精製せずに、との残渣（Ｚｌ
６ Ｆ）にトルエン（１０ｊ）とＮ、Ｎ’−カルボニル
ジイミダゾール（１７Ｆ ）とを加え、５０℃に３時間
、還流下に６時間攪拌する。冷却後、トルエン（６０ｍ
）を追加し、水洗後、無水硫酸ナトリウムで乾燥する。Water (20aj) and 5% potassium hydroxide aqueous solution (20aj) were added to the residue.
Add 0sd) and toluene (10 (17), stir,
Separate the organic layer. After washing the organic layer with water, it is dried over anhydrous sodium sulfate. The residue (λ16f) obtained by distilling off low boilers under reduced pressure is N-(2-C2,6-dichloro-4-(2,2,2-trifluoroethyl) having a refractive index of n201.5210. thio)phenoxy]ethyl)-N-propylamine, but without purification, the residue (Zl
Toluene (10j) and N,N'-carbonyldiimidazole (17F) are added to 6F), and the mixture is stirred at 50°C for 3 hours and under reflux for 6 hours. After cooling, toluene (60m
), washed with water, and dried with anhydrous sodium sulfate.
トルエンを留去すると、下記式で示される目的の１−Ｉ
Ｎ−２−Ｃ２，６−ジクロロ−４−（２，２，２−）リ
クロロエチルチオ）フェノキシ〕−エチルーＮ−７’ロ
ピルカルパモイル）イミダゾール（λ２ｔ）が得られる
。When toluene is distilled off, the desired 1-I shown by the following formula is obtained.
N-2-C2,6-dichloro-4-(2,2,2-)lichloroethylthio)phenoxy]-ethyl-N-7'ropylcarpamoyl)imidazole (λ2t) is obtained.
（化合物ＡＩ）
上記実施例と同様の方法で合成した、本発明化合物を下
記第１表に示す。(Compound AI) Compounds of the present invention synthesized in the same manner as in the above examples are shown in Table 1 below.
前記実施例１で合成原料として、用いられる２−（２，
６−ジクロロ−４−（２，２，２−トリフルオロ・エチ
ルチオ）フェノキシ〕エチルブロマイドの合成例を下記
参考例として示す。2-(2,
A synthesis example of 6-dichloro-4-(2,2,2-trifluoroethylthio)phenoxy]ethyl bromide is shown below as a reference example.
参考例
金属ナトリウム（０，７Ｆ）をエタノール（５０ｄ）に
溶かして得たナトリウムエチラートのエタノール溶液に
、２，６−ジクロロ−４−（２，２゜２−トリフルオロ
エチルチオ）フェノール（８，９ｔ）とエチレンブロマ
イド（２０Ｆ）とを加え、４０℃に２時間、還流下に４
時間攪拌する。エタノール及び過剰のエチレンブロマイ
ドを留去して得られる残渣をトルエン（１５（１７）に
採シ、５チ水酸化カリウム水溶液、水の順に洗浄し、無
水硫酸ナトリウムで乾燥する。トルエンを留去後、減圧
下に蒸留すると、下記式で示される２−（２゜６−ジク
ロロ−４−（２、２、２−トリフルオロエチルチオ）フ
ェノキシ〕エチルブロマイド（７，２ｆ）が得られる。Reference Example 2,6-dichloro-4-(2,2゜2-trifluoroethylthio)phenol (8 , 9t) and ethylene bromide (20F) and heated to 40°C for 2 hours under reflux for 4 hours.
Stir for an hour. The residue obtained by distilling off ethanol and excess ethylene bromide is taken up in toluene (15 (17), washed with aqueous potassium hydroxide solution and water in this order, and dried over anhydrous sodium sulfate. After distilling off the toluene , and distilled under reduced pressure to obtain 2-(2<6-dichloro-4-(2,2,2-trifluoroethylthio)phenoxy]ethyl bromide (7,2f) shown by the following formula.
ｂｐ、 １２４〜１２６℃１０．８寵ＨＰ
Ｉ
Ｉ
（合成原料■−１）
上記参考例と同様の方法によシ、本発明一般式（１）の
化合物の合成原料である前記一般式（ＩＩ）の化合物を
合成した。その結果を下記第２表に示す。bp, 124-126°C, 10.8°C HP II (Synthesis raw material ■-1) By the same method as in the above reference example, the above general formula (II), which is a raw material for synthesis of the compound of general formula (1) of the present invention, ) was synthesized. The results are shown in Table 2 below.
実施例２（水利剤）
本発明化合物４１．１５部、粉末けい藻土と粉末クレー
との混合物（１：５）、８０部、アルキルベンゼンスル
ホン酸ナトリウム、２部、アルキルナフタレンスルホン
酸ナトリウムホルマリン縮合物、３部を粉砕混合し、水
利剤とする。これを水で希釈して、病原菌および／また
はその発生並びに作物病の発生個所に噴霧処理する。Example 2 (Irrigation agent) 41.15 parts of the compound of the present invention, 80 parts of a mixture of powdered diatomaceous earth and powdered clay (1:5), 2 parts of sodium alkylbenzenesulfonate, formalin condensate of sodium alkylnaphthalenesulfonate , 3 parts are ground and mixed to make an irrigation agent. This is diluted with water and sprayed onto locations where pathogenic bacteria and/or their outbreaks and crop diseases occur.
実施例３（乳剤）
本発明化合物／ｌ＆２．３０部、キシレン、５５部、ポ
リオキシエチレンアルキルフェニルエーテル、８部、ア
ルキルベンゼンスルホン酸カルシウム、７部を混合攪拌
して乳剤とする。これを水で希釈して、病原菌および／
または、その発生並びに作物病の発生個所に噴霧処理す
る。Example 3 (Emulsion) An emulsion was prepared by mixing and stirring 2.30 parts/l of the compound of the present invention, 55 parts of xylene, 8 parts of polyoxyethylene alkylphenyl ether, and 7 parts of calcium alkylbenzenesulfonate. Dilute this with water to remove pathogens and/or
Alternatively, spray the area where the disease occurs or where the crop disease occurs.
実施例４（粉剤）
本発明化合物Ａ３．２部、粉末クレー、９８部を粉砕混
合して粉剤とする。これを病原菌および／″またけ、そ
の発生、並びに作物病の発生個所に散粉する。Example 4 (Powder) 3.2 parts of the compound A of the present invention and 98 parts of powdered clay were pulverized and mixed to prepare a powder. This is sprinkled on pathogens and/or areas where pathogens and crop diseases occur.
実施例５（粉剤）
本発明化合物Ａ４．１．５部、イソプロビルノ１イドロ
ゲンホス７エー）（ＰＡＰ）、０．５部、粉末クレー、
９８部を粉砕混合して粉剤とし、病原菌および／または
、その発生、並びに作物病の発生個所に散粉する。Example 5 (powder) 4.1.5 parts of the present compound A, 0.5 parts of isoprobyl-hydrogenphos-7-A (PAP), powdered clay,
98 parts are ground and mixed to make a powder, and the powder is sprinkled on areas where pathogenic bacteria and/or their outbreaks and crop diseases occur.
実施例６（粒剤）
本発明化合物＆３．１０部、ベントナイト（モンモリロ
ナイト）、３０部、タルク（滑石）、５８部、リグニン
スルホン酸塩、２部の混合物に、水、２５部を加え、良
く捏化し、押し出し式造粒機Ｋ１）、１０〜４０メツシ
ユの粒状として、４０〜５０℃で乾燥して粒剤とする。Example 6 (granules) To a mixture of 3.10 parts of the compound of the present invention, 30 parts of bentonite (montmorillonite), 58 parts of talc, and 2 parts of lignin sulfonate, 25 parts of water was added, and the mixture was mixed well. The mixture is kneaded and made into 10 to 40 mesh granules using an extrusion granulator K1), and dried at 40 to 50°C to form granules.
これを病原菌および／ｌたはその発生、並びに作物病の
発生個所に散粒する。This is sprinkled on areas where pathogens and/or their outbreaks and crop diseases occur.
実施例フ
イネいもち病に→する茎葉散布効力試験供試化合物の調
製
活性化合物＝５０重量部
担 体：珪藻土とカオリンとの混合物（１：５）４
５重量部
乳化剤：ポリオキシエチレンアルキルフェニルエーテル
５重量部
上述した量の活性化合物、担体および乳化剤を粉砕混合
して水利剤とし、その所定薬量を水で希釈して調製する
。Example: Preparation of test compound for foliar application efficacy test against Finne blast disease Active compound = 50 parts by weight Carrier: mixture of diatomaceous earth and kaolin (1:5) 4
5 parts by weight Emulsifier: 5 parts by weight of polyoxyethylene alkyl phenyl ether The above-mentioned amounts of the active compound, carrier and emulsifier are pulverized and mixed to form an aquarium, which is prepared by diluting the prescribed amount with water.
試験方法
水稲（品種：朝日）を直径１２ｃＩｒＬの素焼鉢に截培
し、その３〜４葉期に上記のように調製した供試化合物
の所定濃度希釈液を３鉢当、９５０ｓｄ散布した。翌日
人工培養した稲いもち病菌（Ｐｙｒｉｃｕ−１ａｒｉａ
ｏｒｙｚａｅ）胞子の懸濁液を噴霧接種（２回）し、
２５℃、相対湿度１００％の温室に保ち感染せしめた。Test method Paddy rice (variety: Asahi) was cultivated in clay pots with a diameter of 12 cIrL, and at the 3rd to 4th leaf stage, a diluted solution of the test compound at a predetermined concentration prepared as described above was sprayed at 950 sd per 3 pots. The next day, the rice blast fungus (Pyricu-1aria) was artificially cultured.
oryzae) by spray inoculation (twice) with a spore suspension,
The plants were kept in a greenhouse at 25°C and 100% relative humidity to allow infection.
接種７日後、鉢当シの罹病程度を下記の基準によシ類別
評価し、更に防除価（４）を求めた。また薬害も同時に
調査した。Seven days after inoculation, the degree of morbidity of the potted beetles was evaluated according to the following criteria, and the control value (4) was determined. At the same time, drug damage was also investigated.
０．５ ２以下
１ ３〜５
２ ６〜１０
３ １１〜２０
４ ２１〜４０
５ ４１以上
本試験は１区３鉢の結果である。その結果を第３表に示
す。0.5 2 or less 1 3-5 2 6-10 3 11-20 4 21-40 5 41 or more This test is the result of 3 pots in 1 section. The results are shown in Table 3.
第３表
註） 比較Ａ−１：
特開昭５０−３１０４７号公報明細書記載化合物実施例
８
トマトのえき病に対する防除試験
９儂の素焼鉢で栽培したトマト（品種：粟原）Ｋ１実施
例３に準じて調製した乳剤形態の供試化合物をスプレー
ガンを用いて散布した。散布１日後、本病菌の胞子懸濁
液を接種し、２２℃、湿度 。Notes to Table 3) Comparison A-1: Compound described in the specification of JP-A-50-31047 Example 8 Control test against tomato blight blight Tomatoes grown in 9I clay pots (variety: Awahara) K1 Example 3 A test compound in the form of an emulsion prepared according to the method was sprayed using a spray gun. One day after spraying, a spore suspension of this disease bacterium was inoculated and kept at 22°C and humidity.
９０％以上の恒温室内にて一夜放置したのち、５日後に
病斑面積歩合によシ、罹病度を下記基準によシ類別評価
し、防除価を求めた。After being left overnight in a temperature controlled room of 90% or higher, after 5 days, the disease severity was evaluated based on the lesion area ratio and the disease severity according to the following criteria, and the control value was determined.
Ｏ ０，５２以下 １ ３〜５ ２ ６〜１５ ３ １６〜３０ ４ ３１〜５０ ５ ５１以上 その結果を第４表に示す。O 0.52 or less 1 3-5 2 6-15 3 16-30 4 31-50 5 51 or more The results are shown in Table 4.
第４表 註） 比較Ａ−１は第３表と同じ。Table 4 Note) Comparison A-1 is the same as Table 3.
特開昭５０−３１０４７号公報明細書記載化合物実施例
９
キュウリ炭そ病防除試験ニー
試験方法：
化合物をスプレーガンを用いて散布した。散布１日後、
本病原菌（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ ｌａｇｅｎ
ａ−ｒｉｕｍ） の胞子液を噴霧接種し、２３℃、湿度
９０チ以上の恒温室内に一夜放置した後、６日後に実施
例８と同様に、病斑面積歩合によシ発病度を求め、防除
効果を算出した。Example 9 Compound described in JP-A-50-31047 Cucumber anthracnose control test Knee test method: The compound was sprayed using a spray gun. One day after spraying,
This pathogenic bacterium (Colletotrichum lagen)
a-rium) was spray inoculated and left overnight in a constant temperature room at 23°C and humidity of 90°C or higher. After 6 days, the disease severity was determined based on the lesion area ratio in the same manner as in Example 8. The control effect was calculated.
その結果を第５表に示す。The results are shown in Table 5.
第５表 註） Ａ−１及びＡ−２は第４表と同じ。Table 5 Note) A-1 and A-2 are the same as Table 4.
実施例１０
キュウリうどんこ病防除試験
試験方法：
９ｃｒｒＬ素焼鉢で栽培した２葉期のキュウリ（品種と
きわ地這）に実施例３に順じて調製した乳剤形態の供試
化合物をスプレーガンを用いて散布した。Example 10 Cucumber powdery mildew control test Test method: A test compound in the form of an emulsion prepared in accordance with Example 3 was applied to two-leaf stage cucumbers (variety Tokiwa Jiyo) grown in a 9crrL clay pot using a spray gun. It was sprayed.
散布１日後、本病原菌（Ｓｐｈａｅｒｏｔｈｅｃａ ｆ
ｕｌｉ−ｇｉｎｅａ）の胞子液を噴霧接種し、２３℃の
恒温室内に放置した後、１０日後に実施例８と同様に病
斑面積歩合により発病度を求め、防除効果を算出した。One day after spraying, this pathogen (Sphaerotheca f.
uli-ginea) was spray inoculated and left in a constant temperature room at 23° C. After 10 days, the disease severity was determined based on the lesion area ratio in the same manner as in Example 8, and the control effect was calculated.
その結果を第６表に示す。The results are shown in Table 6.
第６表 第 ６ 表 （続） 註） Ａ−１及びＡ−２は第４表と同じ。Table 6 Table 6 (continued) Note) A-1 and A-2 are the same as Table 4.
実施例１１
稲ごま葉枯病に対する茎葉散布効力試験水稲（品種：く
さぶえ）を直径１２ｃｒｒＬの素焼鉢に栽培し、その３
〜４葉期に実施例２に準じて、調製した供試化合物の所
定濃度希釈液を３鉢当り５０ａｊ散布した。翌日人工培
養した稲ごま葉枯病菌胞子の懸濁液を噴霧接種（２回）
Ｌ、２５℃、相対湿度１００％の温室に保ち感染せしめ
た。接種７日後、°鉢当シの罹病程度を下記の基準によ
り類別評価し、更に防除価（４）を求めた。Example 11 Efficacy test of foliar spraying against rice sesame leaf blight Paddy rice (variety: Kusabue) was cultivated in a clay pot with a diameter of 12 crrL,
At the ~4-leaf stage, a diluted solution of a test compound prepared at a predetermined concentration according to Example 2 was sprayed at 50 aj per 3 pots. The next day, spray inoculation with a suspension of artificially cultured rice sesame leaf blight fungus spores (twice)
L, kept in a greenhouse at 25°C and 100% relative humidity and allowed to infect. Seven days after inoculation, the degree of morbidity of the pestle was graded and evaluated according to the following criteria, and the control value (4) was determined.
罹病度 発病程度
０ 発病なし
１微
２少
３中
４多
５甚
本試験は１区３鉢の結果である。その結果を第７表に示
す。Disease severity: 0, no disease, 1, slight, 2, 3, 4, 5, 5. The results of this test are 3 pots in 1 area. The results are shown in Table 7.
第７表 註） 比較Ａ−１及びＡ−２は第４表と同じ。Table 7 Note) Comparisons A-1 and A-2 are the same as Table 4.
実施例１２
イネ苗ごま葉枯病防除試験（種子処理）イネごま葉枯病
菌（Ｈｅｌｍｉｎｔｈｏｓｐｏｒ ｉｕｍｏｒｙｚａｅ
）に高率に自然感染した１子（品種：コシヒカリ）を次
表に示す濃度、方法で実施例２に準じた方法で調製した
所定濃度希釈液で処理し、翌日育苗箱に播種し、通常の
方法で育苗管理した。Example 12 Rice seedling sesame leaf blight control test (seed treatment) Rice seedling sesame leaf blight control test (Helminthospor iumoryzae)
) was naturally infected at a high rate (variety: Koshihikari) with a predetermined concentration diluted solution prepared in accordance with Example 2 at the concentration and method shown in the table below, and the next day, the seedlings were sown in seedling boxes. Seedlings were raised and managed using the following method.
播種１５日後に１全苗を抜き取って罹病苗と健全苗に類
別し、播種粒数に対する健全百本から次式によシ防除価
を算出し、その結果を第８表に示す。Fifteen days after sowing, all the seedlings were taken out and classified into diseased and healthy seedlings, and the pesticidal control value was calculated from the number of sown seeds versus 100 healthy seedlings using the following formula, and the results are shown in Table 8.
１００−（無処理区の健全百本） 表中、処理方法の項は下記の方法を示す。100- (100 healthy trees in untreated area) In the table, the treatment method section indicates the following method.
Ｍ−１：％時間浸種
Ｍ−２：２０時間浸漬
Ｍ−３二種子粉衣
実施例１３
イネ馬鹿苗病防除試験（種子処理）
イネ馬鹿苗病（Ｇｉｂｂｅｒｅｌｌａ ｆｕｊｉｋｕｒ
ｏｉ）に自然感染した種子（品種：コシヒカリ）を次表
に示す濃度、方法で実施例２に準じた方で調製した所定
濃度希釈液に浸漬処理し、種子消毒処理終了後風乾し、
イネ用育苗箱に播種し、通常の方法で育苗管理し、播種
２０日後まで経時的に罹病苗を抜き取り調査し、次式に
よシ防除価（４）を算出し、その結果を第９表に示す。M-1: Seed soaked for % time M-2: Soaked for 20 hours M-3 Two seeds powder coating Example 13 Rice baka-nae disease control test (seed treatment) Rice baka-seed disease (Gibberella fujikur)
Seeds naturally infected with O.i.
The seeds were sown in rice seedling boxes, the seedlings were raised and managed in the usual manner, and diseased seedlings were sampled and investigated over time until 20 days after sowing, and the pest control value (4) was calculated using the following formula, and the results are shown in Table 9. Shown below.
防除価は、１区３００粒の３試験区の平均値を示す。The control value shows the average value of 3 test plots with 300 grains per plot.
第 ９ 表 第 ９ 表 （続） 註） Ａ−１は第３表と同じ。Table 9 Table 9 (continued) Note) A-1 is the same as Table 3.
実施例１４
耐性イネ馬鹿苗病試験（種子処理）
ＭＢＣ耐性の馬鹿苗病菌（：ｂｅｎｏｍｙｌに対する１
ｎｖｉｔｒｏ のＭＩＣ値（生育最小阻止濃度）８００
ｐｐｍ）をイネ（品種：コシヒカリ）の開花期に噴霧
接種して得た感染種子に対する浸漬消毒試験を実施例１
３と同様な方法で実施した。その結果を第１０表に示す
。防除価は、１区３００粒の３試験区の平均値を示す。Example 14 Resistant rice bakanae disease test (seed treatment)
nvitro MIC value (minimum inhibitory concentration) 800
Example 1 A immersion disinfection test was conducted on infected seeds obtained by spray inoculating rice (variety: Koshihikari) with ppm) during the flowering period.
It was carried out in the same manner as in 3. The results are shown in Table 10. The control value shows the average value of 3 test plots with 300 grains per plot.
註） ＭＢＣ耐性菌とは、ｂｅｎｏｍｙｌ、 ｔｈｉ
ｓｐｈａ−ｎａｔｅｍｅｔｈｙｌ及びその類縁化合物に
対して耐性を示す菌を意味する。Note) MBC-resistant bacteria include benomyl, thi
It means a bacterium that is resistant to spha-natemethyl and its related compounds.
第 １０ 表 註） Ａ−１は第３表と同じ。Table 10 Note) A-1 is the same as Table 3.
以上、詳細な説明の項で述べた本発明を要約すれば次の
通シである。The present invention described above in the detailed description section can be summarized as follows.
（１）一般式：
式中、Ｒ１は低級アルキル基、低級アルコキシ−低級ア
ルキル基又は炭素数３〜８のシクロアルキル基を示し、
Ｒ２はフルオル置換−低級アルキル基を示し、
Ｘは酸素原子又はイオウ原子を示し、
Ｙはハロゲン原子又は低級アルキル基を示し、
ｍは０．１又は２を示し、そして
ｎは２．３．４．５又は６を示す、
で表わされるカルバモイルイミダゾール誘導体。(1) General formula: In the formula, R1 represents a lower alkyl group, a lower alkoxy-lower alkyl group, or a cycloalkyl group having 3 to 8 carbon atoms, R2 represents a fluoro-substituted lower alkyl group, and X represents an oxygen atom or A carbamoylimidazole derivative represented by: a sulfur atom, Y represents a halogen atom or a lower alkyl group, m represents 0.1 or 2, and n represents 2.3.4.5 or 6.
（２） 一般式：
式中、Ｒ”、ＸＳｌ’、ｍ及びｎは前記と同じ、そして
Ｈａｌはハロゲン原子を示す、
で表わされる化合物と、
一般式：
％式％（
式中、Ｒ１は前記と同じ、
で表わされる化合物とを反応させ、次いで、Ｎ、Ｎ’−
カルボニルジイミダゾールを反応させることを特徴とす
る前記一般式（Ｉ）のカルバモイルイミダゾール誘導体
の製造方法。(2) A compound represented by the general formula: where R'', XSl', m and n are the same as above, and Hal represents a halogen atom; The same compound as is reacted with, and then N,N'-
A method for producing a carbamoylimidazole derivative of the general formula (I), which comprises reacting carbonyldiimidazole.
（３） 前記一般式（Ｉ）のカルバモイルイミダゾー
ル誘導体を有効成分として含有する農園芸用殺菌剤。(3) An agricultural and horticultural fungicide containing the carbamoylimidazole derivative of the general formula (I) as an active ingredient.
（４）前記一般式（Ｉ）のカルバモイルイミダゾール誘
導体を単独に、または希釈剤（溶剤および／または禮量
剤および／または担体）および／または界面活性剤、更
に必要ならば、安定剤、固着剤、共方剤とを混合して施
用する作物病防除方法。(4) The carbamoylimidazole derivative of the general formula (I) may be used alone, or a diluent (solvent and/or thinning agent and/or carrier) and/or surfactant, and if necessary, a stabilizer and a fixing agent. , a crop disease control method that involves applying a mixture of , and a symbiotic agent.
Claims (1)
アルキル基又は炭素数３〜８の シクロアルキル基を示し、 Ｒ＾２はフルオル置換−低級アルキル基を示し、 Ｘは酸素原子又はイオウ原子を示し、 Ｙはハロゲン原子又は低級アルキル基を示 し、 ｍは０、１又は２を示し、そして ｎは２、３、４、５又は６を示す、 で表わされるカルバモイルイミダゾール誘導体。 ２）式： ▲数式、化学式、表等があります▼ で表わされる特許請求の範囲第１項記載の１−｛Ｎ−２
−〔２，６−ジクロロ−４−（２，２，２−トリフルオ
ロエチルチオ）フェノキシ〕エチル−Ｎ−プロピルカル
バモイル｝イミダゾール。 ３）式： ▲数式、化学式、表等があります▼ で表わされる特許請求の範囲第１項記載の１−〔Ｎ−２
−（２，６−ジクロロ−４−トリフルオロメチルチオフ
ェノキシ）エチル−Ｎ−プロピルカルバモイル〕イミダ
ゾール。 ４）式： ▲数式、化学式、表等があります▼ で表わされる特許請求の範囲第１項記載の１−〔Ｎ−２
−（２，６−ジクロロ−４−トリフルオロメトキシフェ
ノキシ）エチル−Ｎ−プロピルカルバモイル〕イミダゾ
ール。 ５）一般式： ▲数式、化学式、表等があります▼ 式中、Ｒ＾２はフルオル置換−低級アルキル基を示し、 Ｘは酸素原子又はイオウ原子を示し、 Ｙはハロゲン原子又は低級アルキル基を示 し、 ｍは０、１又は２を示し、 ｎは２、３、４、５又は６を示し、そして Ｈａｌはハロゲン原子を示す、 で表わされる化合物と、 一般式：Ｒ＾１−ＮＨ＿２ 式中、Ｒ＾１は低級アルキル基、低級アルコキシ−低級
アルキル基又は炭素数３〜８の シクロアルキル基を示す、 で表わされる化合物とを反応させ、次いでＮ，Ｎ′−カ
ルボニルジイミダゾールを反応させることを特徴とする
、 一般式： ▲数式、化学式、表等があります▼ 式中、Ｒ＾１、Ｒ＾２、Ｘ、Ｙ、ｍ及びｎは前記と同じ
、 で表わされるカルバモイルイミダゾール誘導体の製造方
法。 ６）一般式： ▲数式、化学式、表等があります▼ 式中、Ｒ＾１は低級アルキル基、低級アルコキシ−低級
アルキル基又は炭素数３〜８の シクロアルキル基を示し、 Ｒ＾２はフルオル置換−低級アルキル基を示し、 Ｘは酸素原子又はイオウ原子を示し、 Ｙはハロゲン原子又は低級アルキル基を示 し、 ｍは０、１又は２を示し、そして ｎは２、３、４、５又は６を示す、 で表わされるカルバモイルイミダゾール誘導体を有効成
分として含有する農園芸用殺菌剤。[Claims] 1) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, R^1 represents a lower alkyl group, a lower alkoxy-lower alkyl group, or a cycloalkyl group having 3 to 8 carbon atoms. , R^2 represents a fluoro-substituted lower alkyl group, X represents an oxygen atom or a sulfur atom, Y represents a halogen atom or a lower alkyl group, m represents 0, 1 or 2, and n represents 2, A carbamoylimidazole derivative represented by: 3, 4, 5 or 6. 2) Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ 1-{N-2 described in claim 1 expressed by
-[2,6-dichloro-4-(2,2,2-trifluoroethylthio)phenoxy]ethyl-N-propylcarbamoyl}imidazole. 3) Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ 1-[N-2 described in claim 1, expressed as
-(2,6-dichloro-4-trifluoromethylthiophenoxy)ethyl-N-propylcarbamoyl]imidazole. 4) Formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ 1-[N-2 described in claim 1 expressed by
-(2,6-dichloro-4-trifluoromethoxyphenoxy)ethyl-N-propylcarbamoyl]imidazole. 5) General formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, R^2 represents a fluoro-substituted lower alkyl group, X represents an oxygen atom or a sulfur atom, and Y represents a halogen atom or a lower alkyl group. and m represents 0, 1 or 2, n represents 2, 3, 4, 5 or 6, and Hal represents a halogen atom, and a compound represented by the general formula: R^1-NH_2 in the formula , R^1 represents a lower alkyl group, a lower alkoxy-lower alkyl group, or a cycloalkyl group having 3 to 8 carbon atoms, and then reacting with N,N'-carbonyldiimidazole. A method for producing a carbamoylimidazole derivative represented by a general formula: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ In the formula, R^1, R^2, X, Y, m and n are the same as above. . 6) General formula: ▲There are numerical formulas, chemical formulas, tables, etc.▼ In the formula, R^1 represents a lower alkyl group, a lower alkoxy-lower alkyl group, or a cycloalkyl group having 3 to 8 carbon atoms, and R^2 represents fluorocarbon. represents a substituted lower alkyl group, X represents an oxygen atom or a sulfur atom, Y represents a halogen atom or a lower alkyl group, m represents 0, 1 or 2, and n represents 2, 3, 4, 5 or 6, an agricultural and horticultural fungicide containing a carbamoylimidazole derivative represented by the following as an active ingredient.
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59188778A JPS6168470A (en) | 1984-09-11 | 1984-09-11 | Carbamoylimidazole derivative, its production and agricultural an horticultural fungicide |
| EP85110918A EP0175188A1 (en) | 1984-09-11 | 1985-08-30 | Carbamoylimidazole derivatives |
| PT81072A PT81072B (en) | 1984-09-11 | 1985-09-02 | Process for the preparation of a fungicidal composition with carbamoylimidazole derivatives |
| US06/774,206 US4609669A (en) | 1984-09-11 | 1985-09-09 | Carbamoylimidazole derivatives and fungicidal use thereof |
| GR852178A GR852178B (en) | 1984-09-11 | 1985-09-09 | |
| IL76330A IL76330A0 (en) | 1984-09-11 | 1985-09-09 | Carbamoylimidazole derivatives,their preparation and their use as fungicides |
| KR1019850006601A KR860002475A (en) | 1984-09-11 | 1985-09-10 | Method for preparing carbamoylimidazole derivatives |
| ES546847A ES8609271A1 (en) | 1984-09-11 | 1985-09-10 | Carbamoylimidazole derivatives. |
| ZA856915A ZA856915B (en) | 1984-09-11 | 1985-09-10 | Carbamoylimidazol derivatives,a process for the preparation thereof and their use as agricultural horticultural fungicides |
| DK411585A DK411585A (en) | 1984-09-11 | 1985-09-10 | Carbamoyl imidazole DERIVATIVES |
| BR8504352A BR8504352A (en) | 1984-09-11 | 1985-09-10 | CARBAMOYLIMIDAZOL DERIVATIVES PROCESS FOR ITS PREPARATION, OF FUNGICIDAL COMPOSITIONS, USE, PROCESS TO COMBAT PLANT DISEASES, COMPOUNDS AND PROCESS FOR ITS PREPARATION |
| AU47381/85A AU573032B2 (en) | 1984-09-11 | 1985-09-11 | Carbamoylimidazole derivatives |
| HU853429A HUT39326A (en) | 1984-09-11 | 1985-09-11 | Fungicides containing as reagent derivatives of carbomoil-imidazol and process for production of this reagent |
| ES553067A ES8800168A1 (en) | 1984-09-11 | 1986-03-17 | Carbamoylimidazole derivatives. |
| US06/847,419 US4700006A (en) | 1984-09-11 | 1986-04-03 | Carbamoylimidazole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59188778A JPS6168470A (en) | 1984-09-11 | 1984-09-11 | Carbamoylimidazole derivative, its production and agricultural an horticultural fungicide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6168470A true JPS6168470A (en) | 1986-04-08 |
| JPH0519551B2 JPH0519551B2 (en) | 1993-03-17 |
Family
ID=16229622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59188778A Granted JPS6168470A (en) | 1984-09-11 | 1984-09-11 | Carbamoylimidazole derivative, its production and agricultural an horticultural fungicide |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6168470A (en) |
| ZA (1) | ZA856915B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0866056A1 (en) * | 1995-10-24 | 1998-09-23 | Ube Industries, Ltd. | N- (fluoroalkoxy)phenoxyalkyl]benzamide compounds, intermediates thereof, process for producing the same, and agricultural and horticultural pesticides |
-
1984
- 1984-09-11 JP JP59188778A patent/JPS6168470A/en active Granted
-
1985
- 1985-09-10 ZA ZA856915A patent/ZA856915B/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0866056A1 (en) * | 1995-10-24 | 1998-09-23 | Ube Industries, Ltd. | N- (fluoroalkoxy)phenoxyalkyl]benzamide compounds, intermediates thereof, process for producing the same, and agricultural and horticultural pesticides |
| EP0866056A4 (en) * | 1995-10-24 | 2000-05-24 | Ube Industries | N- (fluoroalkoxy)phenoxyalkyl]benzamide compounds, intermediates thereof, process for producing the same, and agricultural and horticultural pesticides |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA856915B (en) | 1986-05-28 |
| JPH0519551B2 (en) | 1993-03-17 |
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