JPS6168470A - 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 - Google Patents
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Info
- 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
- 239000003795 chemical substances by application Substances 0.000 abstract description 12
- 241000196324 Embryophyta Species 0.000 abstract description 7
- 240000008067 Cucumis sativus Species 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 6
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 5
- 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
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- -1 furoyl Chemical group 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 241000209094 Oryza Species 0.000 description 17
- 235000007164 Oryza sativa Nutrition 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 235000009566 rice Nutrition 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000007921 spray Substances 0.000 description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000004927 clay Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-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
- 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
- 239000003381 stabilizer Substances 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 244000052769 pathogen Species 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
- 244000052616 bacterial pathogen Species 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 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
- 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
- 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
- 239000005909 Kieselgur Substances 0.000 description 3
- 241000227653 Lycopersicon Species 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003905 agrochemical Substances 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
- 150000002170 ethers Chemical class 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000003973 irrigation Methods 0.000 description 3
- 230000002262 irrigation Effects 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- 241000235349 Ascomycota Species 0.000 description 2
- 241000221198 Basidiomycota Species 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000222235 Colletotrichum orbiculare Species 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 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
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 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
- 150000002334 glycols Chemical class 0.000 description 2
- 238000003898 horticulture Methods 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
- 238000002156 mixing Methods 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
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- 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
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- 150000003462 sulfoxides Chemical class 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 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
- 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
- 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
- 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
- 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
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-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
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 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 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
- 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
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
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- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241001450781 Bipolaris oryzae Species 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical class [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
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- 241000195493 Cryptophyta Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000223218 Fusarium Species 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
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- 150000003890 succinate salts Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 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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- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
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- 239000010455 vermiculite Substances 0.000 description 1
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- 239000010457 zeolite Substances 0.000 description 1
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 |
| GR852178A GR852178B (es) | 1984-09-11 | 1985-09-09 | |
| 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 |
| 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 |
| ES546847A ES8609271A1 (es) | 1984-09-11 | 1985-09-10 | Procedimiento para preparar derivados de carbamoilimidazol fungicidas |
| KR1019850006601A KR860002475A (ko) | 1984-09-11 | 1985-09-10 | 카르바모일이미다졸 유도체의 제조방법 |
| ZA856915A ZA856915B (en) | 1984-09-11 | 1985-09-10 | Carbamoylimidazol derivatives,a process for the preparation thereof and their use as agricultural horticultural fungicides |
| 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 true JPS6168470A (ja) | 1986-04-08 |
| JPH0519551B2 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) |
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/ja active Granted
-
1985
- 1985-09-10 ZA ZA856915A patent/ZA856915B/xx 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- (FLUOROALCOXY) PHENOXYALKYL] BENZAMIDE COMPOUNDS, INTERMEDIATES THEREOF, PROCESSES FOR PRODUCING THE SAME AND AGRICULTURAL AND HORTICOLIC PESTICIDES |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0519551B2 (es) | 1993-03-17 |
| ZA856915B (en) | 1986-05-28 |
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