WO1993011118A1 - Herbicides et fongicides derives de pyrole - Google Patents
Herbicides et fongicides derives de pyrole Download PDFInfo
- Publication number
- WO1993011118A1 WO1993011118A1 PCT/EP1992/002723 EP9202723W WO9311118A1 WO 1993011118 A1 WO1993011118 A1 WO 1993011118A1 EP 9202723 W EP9202723 W EP 9202723W WO 9311118 A1 WO9311118 A1 WO 9311118A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- compounds according
- propyl
- coor
- optionally substituted
- Prior art date
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- 239000004009 herbicide Substances 0.000 title description 7
- 239000000417 fungicide Substances 0.000 title description 5
- 150000007980 azole derivatives Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 9
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 125000005605 benzo group Chemical group 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- -1 phenylthio, benzyl Chemical group 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000004094 surface-active agent Substances 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- NZDCOCKQXFTXLD-UHFFFAOYSA-N ethyl 2-(benzenesulfonyl)-2-(2,4-dichlorophenyl)-3-(1,2,4-triazol-1-yl)propanoate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(S(=O)(=O)C=1C=CC=CC=1)(C(=O)OCC)CN1C=NC=N1 NZDCOCKQXFTXLD-UHFFFAOYSA-N 0.000 claims description 5
- 230000000855 fungicidal effect Effects 0.000 claims description 5
- YTMXXFCMOGCGSQ-UHFFFAOYSA-N dipropyl 2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)propanedioate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C(=O)OCCC)(C(=O)OCCC)CN1C=NC=N1 YTMXXFCMOGCGSQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- VUJYDSUGANHNOL-UHFFFAOYSA-N propyl 2-(benzenesulfonyl)-2-(2,4-dichlorophenyl)-3-(1,2,4-triazol-1-yl)propanoate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(S(=O)(=O)C=1C=CC=CC=1)(C(=O)OCCC)CN1C=NC=N1 VUJYDSUGANHNOL-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 14
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
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- PXNMFQMREJNQQT-UHFFFAOYSA-N 1-(chloromethyl)-1,2,4-triazole Chemical compound ClCN1C=NC=N1 PXNMFQMREJNQQT-UHFFFAOYSA-N 0.000 description 2
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- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 description 1
- 239000005591 Pendimethalin Substances 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 239000005594 Phenmedipham Substances 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- UNLYSVIDNRIVFJ-UHFFFAOYSA-N Piperophos Chemical compound CCCOP(=S)(OCCC)SCC(=O)N1CCCCC1C UNLYSVIDNRIVFJ-UHFFFAOYSA-N 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 description 1
- 239000004113 Sepiolite Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 239000005846 Triadimenol Substances 0.000 description 1
- HFBWPRKWDIRYNX-UHFFFAOYSA-N Trietazine Chemical compound CCNC1=NC(Cl)=NC(N(CC)CC)=N1 HFBWPRKWDIRYNX-UHFFFAOYSA-N 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 240000005592 Veronica officinalis Species 0.000 description 1
- 241000990144 Veronica persica Species 0.000 description 1
- 241000394440 Viola arvensis Species 0.000 description 1
- 244000225942 Viola tricolor Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- PPWBRCCBKOWDNB-UHFFFAOYSA-N bensulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C(O)=O)=N1 PPWBRCCBKOWDNB-UHFFFAOYSA-N 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-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
- 125000002091 cationic group Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 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
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 1
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002194 fatty esters Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 description 1
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 description 1
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 0.000 description 1
- 229940099607 manganese chloride Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- NDNKHWUXXOFHTD-UHFFFAOYSA-N metizoline Chemical compound CC=1SC2=CC=CC=C2C=1CC1=NCCN1 NDNKHWUXXOFHTD-UHFFFAOYSA-N 0.000 description 1
- 229960002939 metizoline Drugs 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- QXMNSBFBTDLEEC-UHFFFAOYSA-N propyl 2-(2,4-dichlorophenyl)acetate Chemical compound CCCOC(=O)CC1=CC=C(Cl)C=C1Cl QXMNSBFBTDLEEC-UHFFFAOYSA-N 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
Definitions
- This invention concerns new azole derivatives having herbicidal/fungicidal activity, processes for their preparation, and compositions containing them. Description
- the invention provides the compounds of the formula:
- Az is imidazol-1-yl or 1,2,4-triazol-1-yl
- each X represents halogen, carboxy, nitro, cyano, a group COR 5 , COOR 5 or S(O) p R 5 , or an optionally substituted alkyl, alkoxy, aryl or heteroaryl group; or two adjacent groups X together form a fused benzo group;
- R 1 represents a group CN, COR 5 , COOR 5 or S(O) p R 5 ;
- R 2 represents a group CN, COR 5 , COOR 5 , S(O) p R 5 ,
- R 3 and R 4 which may be the same or different, each represent hydrogen, or an optionally substituted alkyl, aryl or heteroaryl group;
- R 5 represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or heteroaryl group; or hydrogen (but only when p is 0);
- n 0 to 4.
- p is 0 to 2. Any alkyl group present in the molecule is
- the substituent groups may, for example, include halogen, alkoxy of 1 to 4 carbon atoms (eg methoxy or ethoxy), or aryl (eg phenyl).
- Any alkenyl or alkynyl group present in the molecule is preferably of 2 to 6 carbon atoms, eg vinyl, allyl or propargyl.
- Any cycloalkyl group present in the molecule is preferably of 3 to 7 carbon atoms, eg cyclopentyl or cyclohexyl.
- substituent groups may, for example, include halogen, alkyl of 1 to 4 carbon atoms (eg
- Any heteroaryl group present in the molecule is preferably thienyl, furyl or pyridyl.
- R 1 is preferably a group -COOR 5a (particularly where R 5a is alkyl of 1 to 8 carbon atoms, allyl, phenyl or benzyl), and especially such a group where R 5a is methyl, ethyl, n-propyl, iso-propyl or n-butyl.
- R 2 is preferably cyano, optionally substituted phenyl, benzoyl, optionally substituted phenylthio,
- R 5a is alkyl of 1 to 8 carbon atoms, methoxyethyl, cyclopentyl, allyl or benzyl, and especially methyl, ethyl, n-propyl, iso-propyl or
- R 5b is alkyl of 1 to 4 carbon atoms, phenyl, pyridyl or benzyl, especially phenyl).
- R 1 and R 2 are identical and each represents -COOR 5 or phenylthio, or one represents -COOR 5 and the other represents phenylsulphonyl.
- R 3 and R 4 are each preferably hydrogen.
- Az is preferably 1,2,4-triazol-1-yl.
- n is preferably 1 or 2.
- X n preferably represents substitution in the 2- position, or disubstitution in the 2,4- or 2,5-positions on the phenyl ring.
- Preferred substituent groups which X may represent include chloro, bromo, methoxy,
- substitution patterns are 2-methoxy, 2-carboxymethyl, 2- chloro, 2,4-dichloro, 2 ,4-dimethoxy, 2-nitro-4-chloro, 2- methoxy-5-chloro and 2-methoxy-5-bromo.
- the compounds of the invention may be prepared by a process in which a compound of the formula:
- reaction represents a leaving group (especially chlorine), in the presence of a strong base (eg sodium hydride).
- a strong base eg sodium hydride.
- the reaction is preferably effected in a suitable inert solvent medium, eg dimethylformamide.
- the compounds of formulae II and III are themselves either known compounds or may be made by processes analogous to those used for the preparation of similar known compounds.
- the compounds of the invention have activity as herbicides where they exhibit activity against a number of weed species when applied both pre- and post- emergence.
- the compounds are also comparatively safe to certain crop species, and may thus be of use as selective herbicides, particularly in the control of a range of weeds in cereals or other crops, eg wheat, barley, maize, soya beans, oilseed rape, cotton, sugar beet or,
- the compounds of the invention also have activity as fungicides, where their activity is manifested
- the invention also provides a method of combating weeds and/or fungi at a locus infested or liable to be infested therewith, which comprises applying thereto an effective amount of one or more compounds of formula I.
- the invention provides a herbicidal and/or fungicidal composition which comprises one or more compounds of formula I in association with a suitable carrier and/or surface active agent.
- compositions of the invention usually contain from 0.01 to 99% by weight of the present compounds, and are normally produced initially as concentrates
- ingredient comprises from 0.01 to 5% by weight of the formulation applied.
- the carrier may be water, in which case an organic solvent may also be present, though this is not usually employed.
- a flowable suspension concentrate may be formed by grinding the compound with water, a wetting agent and a suspending agent, eg xanthan gum.
- the carrier may alternatively be a water immiscible organic solvent, eg a hydrocarbon which boils within the range 130-270C, eg xylene, in which the compound is dissolved or suspended.
- An emulsifiable concentrate containing a water immiscible solvent may be formed with a surface active agent so that the concentrate acts as a self-emulsifiable oil on admixture with water.
- the carrier may alternatively be a water-miscible organic solvent eg 2-methoxy ethanol, methanol, propylene glycol, diethylene glycol, diethylene glycol monoethyl ether, methylformamide or dimethylformamide.
- a water-miscible organic solvent eg 2-methoxy ethanol, methanol, propylene glycol, diethylene glycol, diethylene glycol monoethyl ether, methylformamide or dimethylformamide.
- the carrier may alternatively be a solid, which may be finely divided or granular.
- suitable solids are limestone, clays, sand, mica, chalk,
- the carrier can be of natural or synthetic origin or can be modified natural material.
- Wettable powders soluble or dispersible in water may be formed by admixing the compound in particulate form with a particulate carrier or spraying molten compound on to the carrier, admixing a wetting agent and a dispersing agent and finely grinding the whole powder mixture.
- An aerosol composition may be formed by admixing the compound with a propellant, eg a polyhalogenated alkane such as dichlorofluoromethane, and suitably also with a solvent.
- 'surface active agent' is used in the broad sense to include materials variously called emulsifying agents, dispersing agents and wetting agents. Such agents are well known in the art.
- the surface active agents used may comprise anionic surface active agents, for example mono- or di-esters of phosphoric acid with a fatty alcohol ethoxylate, or salts of such esters, fatty alcohol sulfates such as sodium dodecyl sulfate, ethoxylated fatty alcohol sulfates, ethoxylated alkylphenol sulfates, lignin sulfates, petroleum sulfonates, alkylaryl sulfonates such as alkyl-benzene sulfonates or lower alkylnaphthalene sulfonates, salts of sulfonated naphthaleneformaldehyde condensates, salts of sulfonated phenolformaldehyde condensates, or more complex sulfonates such as the amide sulfonates, eg the sulfonated condensation product of oleic acid and N-methyl taurine or
- sulfosuccinates eg the sodium sulfonate of dioctyl
- the surface active agents may also comprise
- non-ionic agents for example condensation products or fatty aeid esters, fatty alcohols, fatty acid amides or alkyl-substitutedphenols with ethylene oxide, fatty esters of polyhydric alcohol ethers eg sorbitan fatty acid esters, condensation products of such esters with ethylene oxide eg polyoxyethylene sorbitan fatty acid esters, block copolymers of ethylene oxide and propylene oxide, acetylenic glycols such as 2,4,7,9-tetramethyl-5- decyn-4,7-diol, or ethoxylated acetylenic glycols.
- condensation products or fatty aeid esters for example condensation products or fatty aeid esters, fatty alcohols, fatty acid amides or alkyl-substitutedphenols with ethylene oxide, fatty esters of polyhydric alcohol ethers eg sorbitan fatty acid esters, condensation products of such est
- the surface active agents may also comprise cationic agents, for example alkyl- and/or aryl-substituted quaternary ammonium compounds such as cetyl
- Preferred surface active agents include ethoxylated fatty alcohol sulfates, lignin sulfonates, alkyl-aryl sulfonates, salts of sulfonated naphthaleneformaldehyde condensates, salts of sulfonated phenolformaldehyde condensates, sodium oleoyl N-methyltauride, dialkyl sulfosuccinates, alkyl phenol ethoxylates, and fatty alkyl ethoxylates.
- the present active compounds may be admixed with another pesticide, eg a herbicide, fungicide or
- herbicide or a plant growth regulator, particularly another herbicide.
- Suitable further herbicides include trietazine, linuron, MCPA, dichlorprop, isoxaben, diflufenican, metolachlor, fluometuron, oxyfluorfen, fomesafen, bentazone, prometryne, norflurazon,
- chlomazone EPTC, imazaquin, and especially isoproturon, methabenzthiazuron, trifluralin, ioxynil, bromoxynil, benazolin, mecoprop, fluroxypyr, alachlor, acifluorfen, lactofen, metribuzin, pendimethalin, ethofumesate, benfuresate, phenmedipham, benzophenap, butachlor, chlomethoxyfen, dimepiperate, mefenacet, molinate, naproanilide, oxadiazon, piperophos, prometryne,
- simetryne simetryne, pyrazolate, pretilachlor, thiobencarb and pyributicarb.
- Suitable further fungicides include fenpropimorph, propiconazole, triadimefon, triadimenol, diclobutrazol, prochloraz (and metal complexes of this eg the manganese chloride complex), and guazatine.
- the present compound may be applied to plants, the soil, land or aquatic areas, and particularly to a locus at which a crop is growing. Examples
- Benzenethiol (3.86g) was added to a solution of potassium hydroxide (1.9g) in ethanol (100ml) and the mixture was stirred for 30 minutes.
- Ethyl bromo(2,4- dichlorophenyl) acetate (9.4g) was added dropwise and the mixture was then heated at reflux for 4 hours. After cooling, the mixture was concentrated in vacuo and the residue partitioned between dichloromethane (100ml) and water (100ml). The organic layer was separated and the aqueous solution extracted further with dichloromethane (2 x 100ml). The organic extracts were combined, dried with magnesium sulfate and concentrated in vacuo. The resulting liquid was distilled to give 8.5g of the desired compound, bp 128-45°C at 0.1 mmHg.
- Seeds of the test species listed below were each sown in 8.5cm square pots filled to within 2cm of the top with sterile loam, and were covered with a 2-5mm layer of loam. The pots were watered, and then treated by
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
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Abstract
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR9206862A BR9206862A (pt) | 1991-12-04 | 1992-11-25 | Compostos herbicidas e fungicidas,derivados de azol, e, composição herbicida e/ou fungicida |
JP5509801A JPH07501801A (ja) | 1991-12-04 | 1992-11-25 | アゾール誘導体の除草剤および殺カビ剤 |
EP92923799A EP0619812A1 (fr) | 1991-12-04 | 1992-11-25 | Herbicides et fongicides derives de pyrole |
FI942596A FI942596A0 (fi) | 1991-12-04 | 1994-06-02 | Atsolijohdannaisherbisidit ja fungisidit |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9125791.5 | 1991-12-04 | ||
GB919125791A GB9125791D0 (en) | 1991-12-04 | 1991-12-04 | Herbicides |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1993011118A1 true WO1993011118A1 (fr) | 1993-06-10 |
Family
ID=10705689
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1992/002723 WO1993011118A1 (fr) | 1991-12-04 | 1992-11-25 | Herbicides et fongicides derives de pyrole |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP0619812A1 (fr) |
JP (1) | JPH07501801A (fr) |
CN (1) | CN1075478A (fr) |
AU (1) | AU2945892A (fr) |
BR (1) | BR9206862A (fr) |
CA (1) | CA2124940A1 (fr) |
CZ (1) | CZ129894A3 (fr) |
FI (1) | FI942596A0 (fr) |
GB (1) | GB9125791D0 (fr) |
HU (1) | HUT68182A (fr) |
RU (1) | RU94030811A (fr) |
TW (1) | TW231966B (fr) |
WO (1) | WO1993011118A1 (fr) |
ZA (1) | ZA929336B (fr) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0575122A2 (fr) * | 1992-06-17 | 1993-12-22 | Rohm And Haas Company | Ethyl (2-aryl-2-substitué)-1,2,4-triazoles, fongicides |
EP0576199A2 (fr) * | 1992-06-25 | 1993-12-29 | Rohm And Haas Company | Triazoles fongicides et herbicides |
EP0606748A1 (fr) * | 1993-01-15 | 1994-07-20 | Rohm And Haas Company | Cyanosulphonyléthyl-triazoles et leur application comme fongicides |
EP1088827A1 (fr) * | 1999-09-29 | 2001-04-04 | SSP Co., Ltd. | Dérivées d'azoles ou leurs sels |
US7595338B2 (en) | 2005-04-29 | 2009-09-29 | Wyeth | Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles |
WO2019093522A1 (fr) * | 2017-11-13 | 2019-05-16 | 株式会社クレハ | Dérivé d'azole, composé intermédiaire, procédé de production d'un dérivé d'azole, agent à usage agricole et horticole, et agent de protection de matériau à usage industriel |
WO2020213739A1 (fr) * | 2019-04-19 | 2020-10-22 | 株式会社クレハ | Agent bactéricide à usage agricole ou horticole, procédé de lutte contre les maladies des plantes et utilisation de produit de lutte contre les maladies de plantes |
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EP0000112A1 (fr) * | 1977-06-01 | 1978-12-20 | BASF Aktiengesellschaft | Dérivés soufrés substitués par le triazol, leur préparation et utilisation comme fongicides |
US4167576A (en) * | 1977-10-06 | 1979-09-11 | Rohm And Haas Company | Cyanoaralkylheterocyclic compounds |
DE2831235A1 (de) * | 1978-07-15 | 1980-01-31 | Basf Ag | Neue azolyl- beta -dicarbonyl-verbindungen |
EP0016587A1 (fr) * | 1979-03-09 | 1980-10-01 | Syntex (U.S.A.) Inc. | Dérivés de 1-((naphtyl-substitué)éthyl)-imidazole, compositions pharmaceutiques les contenant et procédés pour leur préparation |
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EP0251775A2 (fr) * | 1986-07-02 | 1988-01-07 | Rohm And Haas Company | Alpha-aryl-alpha-phénéthyl-1H-1,2,4-triazol-1-propane-nitriles |
-
1991
- 1991-12-04 GB GB919125791A patent/GB9125791D0/en active Pending
-
1992
- 1992-11-05 CA CA002124940A patent/CA2124940A1/fr not_active Abandoned
- 1992-11-25 JP JP5509801A patent/JPH07501801A/ja active Pending
- 1992-11-25 WO PCT/EP1992/002723 patent/WO1993011118A1/fr not_active Application Discontinuation
- 1992-11-25 HU HU9401466A patent/HUT68182A/hu active IP Right Revival
- 1992-11-25 AU AU29458/92A patent/AU2945892A/en not_active Abandoned
- 1992-11-25 CZ CZ941298A patent/CZ129894A3/cs unknown
- 1992-11-25 RU RU94030811/04A patent/RU94030811A/ru unknown
- 1992-11-25 EP EP92923799A patent/EP0619812A1/fr not_active Withdrawn
- 1992-11-25 BR BR9206862A patent/BR9206862A/pt not_active Application Discontinuation
- 1992-12-02 ZA ZA929336A patent/ZA929336B/xx unknown
- 1992-12-04 CN CN92115306A patent/CN1075478A/zh active Pending
- 1992-12-10 TW TW081109903A patent/TW231966B/zh active
-
1994
- 1994-06-02 FI FI942596A patent/FI942596A0/fi not_active Application Discontinuation
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US4073921A (en) * | 1975-03-12 | 1978-02-14 | Rohm And Haas Company | Substituted arylcyanoalkyl and diarylcyanoalkylimidazoles and fungical compositions and methods utilizing them |
EP0000112A1 (fr) * | 1977-06-01 | 1978-12-20 | BASF Aktiengesellschaft | Dérivés soufrés substitués par le triazol, leur préparation et utilisation comme fongicides |
US4167576A (en) * | 1977-10-06 | 1979-09-11 | Rohm And Haas Company | Cyanoaralkylheterocyclic compounds |
DE2831235A1 (de) * | 1978-07-15 | 1980-01-31 | Basf Ag | Neue azolyl- beta -dicarbonyl-verbindungen |
EP0016587A1 (fr) * | 1979-03-09 | 1980-10-01 | Syntex (U.S.A.) Inc. | Dérivés de 1-((naphtyl-substitué)éthyl)-imidazole, compositions pharmaceutiques les contenant et procédés pour leur préparation |
EP0022531A1 (fr) * | 1979-07-17 | 1981-01-21 | Bayer Ag | 1-(2,4-Dichlorophényl)-1-(2,6-dihalogéno benzylmercapto)-2-(1,2,4 triazol 1-yl)-éthanes, procédé pour leur préparation et leur utilisation comme fongicides |
EP0061794A1 (fr) * | 1981-03-27 | 1982-10-06 | Janssen Pharmaceutica N.V. | Dérivés d'imidazole antimicrobiens |
EP0061840A2 (fr) * | 1981-03-30 | 1982-10-06 | Imperial Chemical Industries Plc | Composés de triazole, procédé pour leur préparation, leur application comme fungicides de plantes et leurs compositions fongicides |
EP0251775A2 (fr) * | 1986-07-02 | 1988-01-07 | Rohm And Haas Company | Alpha-aryl-alpha-phénéthyl-1H-1,2,4-triazol-1-propane-nitriles |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0575122A2 (fr) * | 1992-06-17 | 1993-12-22 | Rohm And Haas Company | Ethyl (2-aryl-2-substitué)-1,2,4-triazoles, fongicides |
EP0575122A3 (en) * | 1992-06-17 | 1994-05-25 | Rohm & Haas | Fungicidal (2-aryl-2-substituted) ethyl-1,2,4-triazoles |
TR26895A (tr) * | 1992-06-17 | 1994-08-22 | Rohm & Haas Comp | Fungisidal (2-aril-2-ikame-edilmis)etil-1,2,4-triazoller. |
EP0576199A2 (fr) * | 1992-06-25 | 1993-12-29 | Rohm And Haas Company | Triazoles fongicides et herbicides |
EP0576199A3 (en) * | 1992-06-25 | 1994-05-18 | Rohm & Haas | Fungicidal and herbicidal triazoles |
EP0606748A1 (fr) * | 1993-01-15 | 1994-07-20 | Rohm And Haas Company | Cyanosulphonyléthyl-triazoles et leur application comme fongicides |
EP1088827A1 (fr) * | 1999-09-29 | 2001-04-04 | SSP Co., Ltd. | Dérivées d'azoles ou leurs sels |
US6528500B1 (en) | 1999-09-29 | 2003-03-04 | Ssp Co., Ltd. | Azole derivatives or salts thereof |
US7595338B2 (en) | 2005-04-29 | 2009-09-29 | Wyeth | Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles |
WO2019093522A1 (fr) * | 2017-11-13 | 2019-05-16 | 株式会社クレハ | Dérivé d'azole, composé intermédiaire, procédé de production d'un dérivé d'azole, agent à usage agricole et horticole, et agent de protection de matériau à usage industriel |
AU2018365928B2 (en) * | 2017-11-13 | 2020-02-27 | Kureha Corporation | Azole derivative, intermediate compound, method for producing azole derivative, agent for agricultural and horticultural use, and material protection agent for industrial use |
US10945434B2 (en) | 2017-11-13 | 2021-03-16 | Kureha Corporation | Azole derivative, intermediate compound, method for producing azole derivative, agricultural or horticultural chemical agent, and protective agent for industrial material |
WO2020213739A1 (fr) * | 2019-04-19 | 2020-10-22 | 株式会社クレハ | Agent bactéricide à usage agricole ou horticole, procédé de lutte contre les maladies des plantes et utilisation de produit de lutte contre les maladies de plantes |
KR20210141781A (ko) * | 2019-04-19 | 2021-11-23 | 가부시끼가이샤 구레하 | 농원예용 살균제, 식물 병해 방제 방법 및 식물 병해 방제용 제품 |
KR102404296B1 (ko) | 2019-04-19 | 2022-05-31 | 가부시끼가이샤 구레하 | 농원예용 살균제, 식물 병해 방제 방법 및 식물 병해 방제용 제품 |
Also Published As
Publication number | Publication date |
---|---|
CA2124940A1 (fr) | 1993-06-10 |
FI942596A (fi) | 1994-06-02 |
HU9401466D0 (en) | 1994-08-29 |
JPH07501801A (ja) | 1995-02-23 |
HUT68182A (en) | 1995-03-13 |
RU94030811A (ru) | 1996-04-20 |
EP0619812A1 (fr) | 1994-10-19 |
CZ129894A3 (en) | 1994-12-15 |
TW231966B (fr) | 1994-10-11 |
ZA929336B (en) | 1993-08-02 |
GB9125791D0 (en) | 1992-02-05 |
CN1075478A (zh) | 1993-08-25 |
FI942596A0 (fi) | 1994-06-02 |
AU2945892A (en) | 1993-06-28 |
BR9206862A (pt) | 1995-11-21 |
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