JPH0519551B2 - - Google Patents
Info
- Publication number
- JPH0519551B2 JPH0519551B2 JP59188778A JP18877884A JPH0519551B2 JP H0519551 B2 JPH0519551 B2 JP H0519551B2 JP 59188778 A JP59188778 A JP 59188778A JP 18877884 A JP18877884 A JP 18877884A JP H0519551 B2 JPH0519551 B2 JP H0519551B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl group
- lower alkyl
- formula
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 56
- -1 4-trifluoromethylthiophenoxy Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- NMIZONYLXCOHEF-UHFFFAOYSA-N 1h-imidazole-2-carboxamide Chemical class NC(=O)C1=NC=CN1 NMIZONYLXCOHEF-UHFFFAOYSA-N 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 230000000855 fungicidal effect Effects 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000000417 fungicide Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 150000002460 imidazoles Chemical class 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 201000010099 disease Diseases 0.000 description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 23
- 241000209094 Oryza Species 0.000 description 17
- 235000007164 Oryza sativa Nutrition 0.000 description 17
- 235000009566 rice Nutrition 0.000 description 17
- 238000000034 method Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 9
- 239000004927 clay Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000207961 Sesamum Species 0.000 description 6
- 235000003434 Sesamum indicum Nutrition 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000003905 agrochemical Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 244000052769 pathogen Species 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 240000008067 Cucumis sativus Species 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 5
- 241000233866 Fungi Species 0.000 description 5
- 230000003902 lesion Effects 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 235000009849 Cucumis sativus Nutrition 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000004372 Polyvinyl alcohol Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 description 4
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
- IUIKUBWZELWFSF-UHFFFAOYSA-N 2-(2-bromoethoxy)-1,3-dichloro-5-(2,2,2-trifluoroethylsulfanyl)benzene Chemical compound FC(F)(F)CSC1=CC(Cl)=C(OCCBr)C(Cl)=C1 IUIKUBWZELWFSF-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- 241000221778 Fusarium fujikuroi Species 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 241001330975 Magnaporthe oryzae Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 240000003768 Solanum lycopersicum Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 244000052616 bacterial pathogen Species 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 241000235349 Ascomycota Species 0.000 description 2
- 241000221198 Basidiomycota Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000317981 Podosphaera fuliginea Species 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229940072049 amyl acetate Drugs 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000003380 propellant Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000000391 smoking effect Effects 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- WWYNJERNGUHSAO-XUDSTZEESA-N (+)-Norgestrel Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 WWYNJERNGUHSAO-XUDSTZEESA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- JUYANBPYCKBJTI-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-chloro-4-(2,2,2-trifluoroethylsulfanyl)benzene Chemical compound FC(F)(F)CSC1=CC=C(OCCBr)C(Cl)=C1 JUYANBPYCKBJTI-UHFFFAOYSA-N 0.000 description 1
- NSPLEROKSMHENN-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-chloro-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(OCCBr)C(Cl)=C1 NSPLEROKSMHENN-UHFFFAOYSA-N 0.000 description 1
- NVRPUDQHNWRASW-UHFFFAOYSA-N 1-(2-bromoethoxy)-4-(2,2,2-trifluoroethylsulfanyl)benzene Chemical compound FC(F)(F)CSC1=CC=C(OCCBr)C=C1 NVRPUDQHNWRASW-UHFFFAOYSA-N 0.000 description 1
- QESONWISJWXHAA-UHFFFAOYSA-N 1-(2-bromoethoxy)-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(OCCBr)C=C1 QESONWISJWXHAA-UHFFFAOYSA-N 0.000 description 1
- PUYQSEFBQVFXML-UHFFFAOYSA-N 1-(2-bromoethylsulfanyl)-2-chloro-4-(trifluoromethyl)benzene Chemical compound ClC1=C(SCCBr)C=CC(=C1)C(F)(F)F PUYQSEFBQVFXML-UHFFFAOYSA-N 0.000 description 1
- QCJHCGQPTBGUFH-UHFFFAOYSA-N 1-(2-bromoethylsulfanyl)-4-(trifluoromethyl)benzene Chemical compound FC(C1=CC=C(SCCBr)C=C1)(F)F QCJHCGQPTBGUFH-UHFFFAOYSA-N 0.000 description 1
- BNORLZXCTCAHFO-UHFFFAOYSA-N 1-(3-bromopropoxy)-2-chloro-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(OCCCBr)C(Cl)=C1 BNORLZXCTCAHFO-UHFFFAOYSA-N 0.000 description 1
- HRVXELKCNSUDPF-UHFFFAOYSA-N 1-(3-bromopropoxy)-4-(2,2,2-trifluoroethylsulfanyl)benzene Chemical compound FC(F)(F)CSC1=CC=C(OCCCBr)C=C1 HRVXELKCNSUDPF-UHFFFAOYSA-N 0.000 description 1
- RASDCGNENJFFNR-UHFFFAOYSA-N 1-(3-bromopropoxy)-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(OCCCBr)C=C1 RASDCGNENJFFNR-UHFFFAOYSA-N 0.000 description 1
- BTTMSHGRFGEYJN-UHFFFAOYSA-N 1-(3-bromopropylsulfanyl)-2-chloro-4-(trifluoromethyl)benzene Chemical compound ClC1=C(SCCCBr)C=CC(=C1)C(F)(F)F BTTMSHGRFGEYJN-UHFFFAOYSA-N 0.000 description 1
- JKBVYEHNIOEVOM-UHFFFAOYSA-N 1-(3-bromopropylsulfanyl)-4-(trifluoromethyl)benzene Chemical compound FC(C1=CC=C(SCCCBr)C=C1)(F)F JKBVYEHNIOEVOM-UHFFFAOYSA-N 0.000 description 1
- MDQZZBGGMITCTF-UHFFFAOYSA-N 1-(4-bromobutoxy)-2-chloro-4-(2,2,2-trifluoroethylsulfanyl)benzene Chemical compound FC(F)(F)CSC1=CC=C(OCCCCBr)C(Cl)=C1 MDQZZBGGMITCTF-UHFFFAOYSA-N 0.000 description 1
- VZTZNABJKHLBRE-UHFFFAOYSA-N 1-(4-bromobutoxy)-4-(2,2,2-trifluoroethylsulfanyl)benzene Chemical compound FC(F)(F)CSC1=CC=C(OCCCCBr)C=C1 VZTZNABJKHLBRE-UHFFFAOYSA-N 0.000 description 1
- HRMUGIMPMXWFJD-UHFFFAOYSA-N 1-(4-bromobutylsulfanyl)-2-chloro-4-(trifluoromethyl)benzene Chemical compound ClC1=C(SCCCCBr)C=CC(=C1)C(F)(F)F HRMUGIMPMXWFJD-UHFFFAOYSA-N 0.000 description 1
- GOZIPMPTEZTQLI-UHFFFAOYSA-N 1-(4-bromobutylsulfanyl)-4-(trifluoromethyl)benzene Chemical compound FC(C1=CC=C(SCCCCBr)C=C1)(F)F GOZIPMPTEZTQLI-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- QYLBRHUTIJBHPN-UHFFFAOYSA-N 2,6-dichloro-4-(2,2,2-trifluoroethylsulfanyl)phenol Chemical compound OC1=C(Cl)C=C(SCC(F)(F)F)C=C1Cl QYLBRHUTIJBHPN-UHFFFAOYSA-N 0.000 description 1
- SZRSKKGPFBJPJE-UHFFFAOYSA-N 2-(2-bromoethoxy)-1,3-dichloro-5-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC(Cl)=C(OCCBr)C(Cl)=C1 SZRSKKGPFBJPJE-UHFFFAOYSA-N 0.000 description 1
- PXHWGKULVHQWNH-UHFFFAOYSA-N 2-(2-bromoethylsulfanyl)-1,3-dichloro-5-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=C(SCCBr)C(Cl)=C1 PXHWGKULVHQWNH-UHFFFAOYSA-N 0.000 description 1
- KCCPYVKWXFSHQE-UHFFFAOYSA-N 2-(3-bromopropoxy)-1,3-dichloro-5-(2,2,2-trifluoroethylsulfanyl)benzene Chemical compound FC(F)(F)CSC1=CC(Cl)=C(OCCCBr)C(Cl)=C1 KCCPYVKWXFSHQE-UHFFFAOYSA-N 0.000 description 1
- QFGRCMVECWOHAR-UHFFFAOYSA-N 2-(3-bromopropoxy)-1,3-dichloro-5-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC(Cl)=C(OCCCBr)C(Cl)=C1 QFGRCMVECWOHAR-UHFFFAOYSA-N 0.000 description 1
- CHQQPGWJOZYXNT-UHFFFAOYSA-N 2-(3-bromopropylsulfanyl)-1,3-dichloro-5-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Cl)=C(SCCCBr)C(Cl)=C1 CHQQPGWJOZYXNT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- BPGIOCZAQDIBPI-UHFFFAOYSA-N 2-ethoxyethanamine Chemical compound CCOCCN BPGIOCZAQDIBPI-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59188778A JPS6168470A (ja) | 1984-09-11 | 1984-09-11 | カルバモイルイミダゾ−ル誘導体、その製法及び農園芸用殺菌剤 |
| EP85110918A EP0175188A1 (de) | 1984-09-11 | 1985-08-30 | Carbamoylimidazol-Derivate |
| 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 |
| IL76330A IL76330A0 (en) | 1984-09-11 | 1985-09-09 | Carbamoylimidazole derivatives,their preparation and their use as fungicides |
| GR852178A GR852178B (es) | 1984-09-11 | 1985-09-09 | |
| KR1019850006601A KR860002475A (ko) | 1984-09-11 | 1985-09-10 | 카르바모일이미다졸 유도체의 제조방법 |
| BR8504352A BR8504352A (pt) | 1984-09-11 | 1985-09-10 | Derivados de carbamoilimidazol processo para sua preparacao,de composicoes fungicidas,uso,processo para combater doencas de plantas,compostos e processo para sua preparacao |
| DK411585A DK411585A (da) | 1984-09-11 | 1985-09-10 | Carbamoylimidazol-derivater |
| ZA856915A ZA856915B (en) | 1984-09-11 | 1985-09-10 | Carbamoylimidazol derivatives,a process for the preparation thereof and their use as agricultural horticultural fungicides |
| ES546847A ES8609271A1 (es) | 1984-09-11 | 1985-09-10 | Procedimiento para preparar derivados de carbamoilimidazol fungicidas |
| 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 (es) | 1984-09-11 | 1986-03-17 | Procedimiento para preparar derivados de carbamoilimidazol fungicidas |
| 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 (ja) | 1984-09-11 | 1984-09-11 | カルバモイルイミダゾ−ル誘導体、その製法及び農園芸用殺菌剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6168470A JPS6168470A (ja) | 1986-04-08 |
| JPH0519551B2 true JPH0519551B2 (es) | 1993-03-17 |
Family
ID=16229622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59188778A Granted JPS6168470A (ja) | 1984-09-11 | 1984-09-11 | カルバモイルイミダゾ−ル誘導体、その製法及び農園芸用殺菌剤 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS6168470A (es) |
| ZA (1) | ZA856915B (es) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0866056B1 (en) * | 1995-10-24 | 2003-01-08 | 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/ja active Granted
-
1985
- 1985-09-10 ZA ZA856915A patent/ZA856915B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA856915B (en) | 1986-05-28 |
| JPS6168470A (ja) | 1986-04-08 |
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