CN1259013A - 除草剂组合物 - Google Patents
除草剂组合物 Download PDFInfo
- Publication number
- CN1259013A CN1259013A CN98805742A CN98805742A CN1259013A CN 1259013 A CN1259013 A CN 1259013A CN 98805742 A CN98805742 A CN 98805742A CN 98805742 A CN98805742 A CN 98805742A CN 1259013 A CN1259013 A CN 1259013A
- Authority
- CN
- China
- Prior art keywords
- ketone
- thiadiazoles
- methyl
- chloro
- phenyl
- 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.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 55
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 51
- 239000004009 herbicide Substances 0.000 claims abstract description 51
- 241000196324 Embryophyta Species 0.000 claims abstract description 17
- -1 aryl thiadiazoles ketone Chemical class 0.000 claims description 77
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 claims description 25
- 244000025254 Cannabis sativa Species 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 17
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 15
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 claims description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
- VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 claims description 14
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims description 12
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 claims description 12
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 claims description 10
- 239000005484 Bifenox Substances 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- FMGZEUWROYGLAY-UHFFFAOYSA-N Halosulfuron-methyl Chemical group ClC1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC FMGZEUWROYGLAY-UHFFFAOYSA-N 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 238000009333 weeding Methods 0.000 claims description 9
- OVXMBIVWNJDDSM-UHFFFAOYSA-N (benzhydrylideneamino) 2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate Chemical compound COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C(=O)ON=C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 OVXMBIVWNJDDSM-UHFFFAOYSA-N 0.000 claims description 8
- 239000005647 Chlorpropham Substances 0.000 claims description 8
- 239000005590 Oxyfluorfen Substances 0.000 claims description 8
- 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 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 8
- 150000003851 azoles Chemical class 0.000 claims description 8
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 claims description 8
- LLLFASISUZUJEQ-UHFFFAOYSA-N orbencarb Chemical compound CCN(CC)C(=O)SCC1=CC=CC=C1Cl LLLFASISUZUJEQ-UHFFFAOYSA-N 0.000 claims description 8
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 claims description 8
- 235000019260 propionic acid Nutrition 0.000 claims description 8
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 claims description 8
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 8
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 claims description 8
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 claims description 7
- 239000002890 Aclonifen Substances 0.000 claims description 7
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 claims description 7
- 239000005564 Halosulfuron methyl Substances 0.000 claims description 7
- 239000005625 Tri-allate Substances 0.000 claims description 7
- MWBPRDONLNQCFV-UHFFFAOYSA-N Tri-allate Chemical compound CC(C)N(C(C)C)C(=O)SCC(Cl)=C(Cl)Cl MWBPRDONLNQCFV-UHFFFAOYSA-N 0.000 claims description 7
- DDBMQDADIHOWIC-UHFFFAOYSA-N aclonifen Chemical compound C1=C([N+]([O-])=O)C(N)=C(Cl)C(OC=2C=CC=CC=2)=C1 DDBMQDADIHOWIC-UHFFFAOYSA-N 0.000 claims description 7
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 claims description 6
- NYRMIJKDBAQCHC-UHFFFAOYSA-N 5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]furan-3(2H)-one Chemical compound O1C(NC)=C(C=2C=C(C=CC=2)C(F)(F)F)C(=O)C1C1=CC=CC=C1 NYRMIJKDBAQCHC-UHFFFAOYSA-N 0.000 claims description 6
- DVOODWOZJVJKQR-UHFFFAOYSA-N 5-tert-butyl-3-(2,4-dichloro-5-prop-2-ynoxyphenyl)-1,3,4-oxadiazol-2-one Chemical group O=C1OC(C(C)(C)C)=NN1C1=CC(OCC#C)=C(Cl)C=C1Cl DVOODWOZJVJKQR-UHFFFAOYSA-N 0.000 claims description 6
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 6
- SPNQRCTZKIBOAX-UHFFFAOYSA-N Butralin Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(C)(C)C)C=C1[N+]([O-])=O SPNQRCTZKIBOAX-UHFFFAOYSA-N 0.000 claims description 6
- 239000005499 Clomazone Substances 0.000 claims description 6
- PTFJIKYUEPWBMS-UHFFFAOYSA-N Ethalfluralin Chemical compound CC(=C)CN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O PTFJIKYUEPWBMS-UHFFFAOYSA-N 0.000 claims description 6
- MNFMIVVPXOGUMX-UHFFFAOYSA-N Fluchloralin Chemical compound CCCN(CCCl)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O MNFMIVVPXOGUMX-UHFFFAOYSA-N 0.000 claims description 6
- 239000005559 Flurtamone Substances 0.000 claims description 6
- RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 claims description 6
- LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 claims description 6
- 240000007594 Oryza sativa Species 0.000 claims description 6
- 235000007164 Oryza sativa Nutrition 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 239000005591 Pendimethalin Substances 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 6
- 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 claims description 6
- MAHPNPYYQAIOJN-UHFFFAOYSA-N azimsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C2=NN(C)N=N2)C)=N1 MAHPNPYYQAIOJN-UHFFFAOYSA-N 0.000 claims description 6
- 235000013339 cereals Nutrition 0.000 claims description 6
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 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 claims description 6
- 238000002203 pretreatment Methods 0.000 claims description 6
- 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 claims description 6
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- NXQDBZGWYSEGFL-UHFFFAOYSA-N Anilofos Chemical compound COP(=S)(OC)SCC(=O)N(C(C)C)C1=CC=C(Cl)C=C1 NXQDBZGWYSEGFL-UHFFFAOYSA-N 0.000 claims description 5
- DXXVCXKMSWHGTF-UHFFFAOYSA-N Chlomethoxyfen Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 DXXVCXKMSWHGTF-UHFFFAOYSA-N 0.000 claims description 5
- LPXYXBZAXFTFKH-UHFFFAOYSA-N ClC=1C(=C(C(=NC1)C(=O)O)C(=O)O)Cl Chemical compound ClC=1C(=C(C(=NC1)C(=O)O)C(=O)O)Cl LPXYXBZAXFTFKH-UHFFFAOYSA-N 0.000 claims description 5
- NNYRZQHKCHEXSD-UHFFFAOYSA-N Daimuron Chemical compound C1=CC(C)=CC=C1NC(=O)NC(C)(C)C1=CC=CC=C1 NNYRZQHKCHEXSD-UHFFFAOYSA-N 0.000 claims description 5
- 239000005507 Diflufenican Substances 0.000 claims description 5
- BXEHUCNTIZGSOJ-UHFFFAOYSA-N Esprocarb Chemical compound CC(C)C(C)N(CC)C(=O)SCC1=CC=CC=C1 BXEHUCNTIZGSOJ-UHFFFAOYSA-N 0.000 claims description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 claims description 5
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- WLFDQEVORAMCIM-UHFFFAOYSA-N Metobromuron Chemical compound CON(C)C(=O)NC1=CC=C(Br)C=C1 WLFDQEVORAMCIM-UHFFFAOYSA-N 0.000 claims description 5
- UNLYSVIDNRIVFJ-UHFFFAOYSA-N Piperophos Chemical compound CCCOP(=S)(OCCC)SCC(=O)N1CCCCC1C UNLYSVIDNRIVFJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000005603 Prosulfocarb Substances 0.000 claims description 5
- VXMNDQDDWDDKOQ-UHFFFAOYSA-N Pyrazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C(O)=O)C)=N1 VXMNDQDDWDDKOQ-UHFFFAOYSA-N 0.000 claims description 5
- QHTQREMOGMZHJV-UHFFFAOYSA-N Thiobencarb Chemical compound CCN(CC)C(=O)SCC1=CC=C(Cl)C=C1 QHTQREMOGMZHJV-UHFFFAOYSA-N 0.000 claims description 5
- PHSUVQBHRAWOQD-UHFFFAOYSA-N Tiocarbazil Chemical compound CCC(C)N(C(C)CC)C(=O)SCC1=CC=CC=C1 PHSUVQBHRAWOQD-UHFFFAOYSA-N 0.000 claims description 5
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 claims description 5
- RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 claims description 5
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- BWUPSGJXXPATLU-UHFFFAOYSA-N dimepiperate Chemical compound C=1C=CC=CC=1C(C)(C)SC(=O)N1CCCCC1 BWUPSGJXXPATLU-UHFFFAOYSA-N 0.000 claims description 5
- ZZUUAHLFRDBNIS-UHFFFAOYSA-N diphenylmethanone;1h-pyrrole Chemical class C=1C=CNC=1.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 ZZUUAHLFRDBNIS-UHFFFAOYSA-N 0.000 claims description 5
- 230000008029 eradication Effects 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 claims description 5
- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 claims description 5
- OQZCSNDVOWYALR-UHFFFAOYSA-N flurochloridone Chemical compound FC(F)(F)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 OQZCSNDVOWYALR-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 claims description 5
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 claims description 5
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 claims description 5
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- 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 claims description 5
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- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 claims description 4
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 claims description 4
- BDQWWOHKFDSADC-UHFFFAOYSA-N 2-(2,4-dichloro-3-methylphenoxy)-n-phenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C)OC1=CC=C(Cl)C(C)=C1Cl BDQWWOHKFDSADC-UHFFFAOYSA-N 0.000 claims description 4
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 claims description 4
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 claims description 4
- ADZSGNDOZREKJK-UHFFFAOYSA-N 4-amino-6-tert-butyl-3-ethylsulfanyl-1,2,4-triazin-5-one Chemical compound CCSC1=NN=C(C(C)(C)C)C(=O)N1N ADZSGNDOZREKJK-UHFFFAOYSA-N 0.000 claims description 4
- 239000005469 Azimsulfuron Substances 0.000 claims description 4
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 claims description 4
- 239000005472 Bensulfuron methyl Substances 0.000 claims description 4
- RRNIZKPFKNDSRS-UHFFFAOYSA-N Bensulide Chemical compound CC(C)OP(=S)(OC(C)C)SCCNS(=O)(=O)C1=CC=CC=C1 RRNIZKPFKNDSRS-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
除草剂组合物包含:(a)至少一种具有通式(Ⅰ)的芳基噻二唑酮;(b)一种或多种已知的除草剂。上述除草剂组合物可用于防治农业作物的杂草。
Description
本发明涉及除草剂组合物。
更具体地说,本发明涉及含有至少一种芳基噻二唑酮和一种或多种已知除草剂的除草组合物,以及它们在防治农作物杂草上的应用。
实际上,本申请人已发现含有一种或多种已知除草剂和至少一种属于3-芳基-1,3,4-噻二唑-2(3H)-酮类化合物的除草剂组合物,对各种杂草具有令人惊奇的除草活性,而且对重要的农业作物没有药害。
因此本发明的除草剂组合物含有:
-R代表直链或支链C1-C6烷基或卤代烷基;或C3-C6环烷基或卤代环烷基;所述的烷基或卤代烷基、环烷基或卤代环烷基可任选地被直链或支链C1-C3烷基取代;
-X代表卤素原子,如氯或氟;
-Y代表卤素原子,如氯、氟、溴或碘;直链或支链C1-C4烷基或卤代烷基;直链或支链C1-C4烷氧基或卤代烷氧基;
-R1代表氢原子或甲基;
(b)一种或多种选自下列的除草剂:草灭畏、敌草索、麦草畏、萘草胺、草芽平、二氯吡啶酸、二氟草灭(diflufenzopyr(SAN 835 H))、氟硫草定、氨氯吡啶酸、噻唑烟酸(MON 13200)、二氯喹啉酸、氯甲喹啉酸、印丹丰(indanofan(MK-243))、草除灵、氯甲丹、茅草枯、茵多酸、氟燕灵、麦草氟甲酯、四氟丙酸、芴丁酯、三氯醋酸钠、溴丁酰草胺、氯硫酰草胺、吡氟酰草胺、双苯酰草胺、ethabenzanid(HW52)、异噁草胺(isoxaben)、苯噻酰草胺、庚酰草胺、甲氯酰草胺、敌稗、炔苯酰草胺、牧草胺、氟硫胺(fluthiamide(BAY FOE 5043))、炔草酯、稗草胺、氰氟草酯、2,4-滴、2,4-滴丁酸、2,4-滴丙酸、精2,4-滴丙酸、禾草灵、恶唑禾草灵、精恶唑禾草灵、吡氟禾草灵、精吡氟禾草灵、氯氟吡氧乙酸、吡氟氯禾灵、氟吡甲禾灵、异恶草醚、二甲四氯、二甲四氯乙硫酯(MCPA-thioethyl)、二甲四氯丁酸、二甲四氯丙酸、精二甲四氯丙酸、萘丙胺、敌草胺、恶草酸、喹禾灵、精喹禾灵、三氯吡氧乙酸、喹禾糖酯、溴酚肟、溴苯腈、敌草腈、碘苯腈、敌草快、百草枯、磺草灵、丁草特、双酰草胺、氯炔灵、氯苯胺灵、环草敌、甜菜安、哌草丹、茵草敌、戊草丹、禾草敌、坪草丹、克草敌、甜菜宁、苯胺灵、苄草丹、稗草丹、禾草丹、仲草丹、野燕畏、灭草敌、禾草灭、butroxydim、烯草酮、噻草酮、稀禾啶、磺草酮、三甲苯草酮、乙草胺、甲草胺、丁草胺、丁烯草胺、乙酰甲草胺、二甲草胺、二甲吩草胺、吡唑胺、异丙甲草胺、丙草胺、毒草胺、异丙草胺、杀草胺(tenylchlor(NSK-850))、三氟羧草醚、苯草醚、甲羧除草醚、甲氧除草醚、草枯醚、athoxyfen-ethyl(HC-252)、乙羧氟草醚、氟除草醚、氟磺胺草醚、呋氧草醚、乳氟禾草灵、氟草醚、乙氧氟草醚、乙丁氟灵、仲丁灵、dintramide、乙丁烯氟灵、氯乙氟灵、异丙乐灵、氨磺乐灵、二甲戊乐灵、氨基丙氟灵、氟乐灵、地乐酚、地乐酯、特乐酚、杀草强、呋草黄、灭草松、吡草酮、苯酮唑、carfentrazone-ethyl(F-8426)、氯草敏、环庚草醚、异噁草酮、野燕枯、乙氧呋草黄、pyraflufen-ethyl(ET-751)、氟烯草酸、丙炔氟草胺、flumipropin、胺草唑、氟啶草酮、氟咯草酮、呋草酮、嗪草酸、噁氟酮(isoxaflutone(RPA 201772))、灭草唑、氟氯草胺、哒草伏、oxadiargyl、恶草酮、oxaziclomefone(MY-100)、戊噁草酮(pentoxazone(KPP-314))、吡唑特、苄草唑、哒草特、甲磺草胺、thidiazimin、莎稗磷、地散磷、双丙氨酰膦、抑草磷、膦铵素、草铵膦、草甘膦、磺草膦、哌草磷、咪草酸、甲咪唑烟酸、imazamox(AC-299,263)、咪唑烟酸、灭草喹、咪草烟、双草醚、pyribenzoxim(LGC-40863)、嘧草醚、嘧草硫醚、嘧草胺、cloransulam-methyl(XDE-565)、diclosulam(XDE-564)、唑嘧磺草胺、磺草唑胺、酰嘧磺隆、四唑嘧磺隆、苄嘧磺隆、氯嘧磺隆、氯磺隆、醚磺隆、环丙嘧磺隆、胺苯磺隆、乙氧嘧磺隆、啶嘧磺隆、flupyrsufuron(DPX-KE459)、氯吡嘧磺隆、唑吡嘧磺隆、甲黄隆、唑嘧磺隆、烟嘧磺隆、噁磺隆(oxasulfuron(CGA-277476))、氟嘧磺隆、氟磺隆、吡嘧磺隆、砜嘧磺隆、甲嘧磺隆、草磺隆(sulfosulfuron(MON-37500))、噻吩磺隆、醚苯磺隆、苯磺隆、氟胺磺隆、莠灭净、莠去津、叠氮净、氰草津、敌草净、二甲丙乙净、异丙净、甘草津、甲氧丙净、甘扑津、扑灭通、扑草净、扑灭津、西玛津、西草净、特丁通、特丁津、特丁净、triaziflam(IDH-1105)、草达津、乙嗪草酮、环嗪酮、苯嗪草酮、嗪草酮、除草定、环草啶、特草定、苯噻隆、氯秀隆、枯草隆、绿麦隆、除草隆(cumyluron(JC-940))、杀草隆、枯莠隆、恶唑隆、敌草隆、磺噻隆、非草隆、氟草隆、异丙隆(isoproturon)、异恶隆、利谷隆、甲基苯噻隆、甲基杀草隆、吡喃隆、秀谷隆、甲氧隆、绿谷隆、草不隆、环草隆、丁噻隆、噻氟隆、异丙唑(isopropazol(JV485))、KPP 300、KPP 421、BAY YRL 2388、DPXT 5975、azafenidin。
可用于本发明目的的式(I)芳基噻二唑酮的具体实施例为:
3-[2,4-二氯-5-(2-丙炔氧基)苯基]-5-(1,1-二甲基乙基)-1,3,4-噻二唑-2(3H)-酮(化合物1);
3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-5-(1,1-二甲基乙基)-1,3,4-噻二唑-2(3H)-酮(化合物2);
5-环丙基-3-[2,4-二氯-5-(2-丙炔氧基)苯基]-1,3,4-噻二唑-2(3H)-酮(化合物3);
5-环丙基-3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-1,3,4-噻二唑-2(3H)-酮(化合物4);
3-[2,4-二氯-5-(2-丙炔氧基)苯基]-5-(1-甲基乙基)-1,3,4-噻二唑-2(3H)-酮(化合物5);
3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-5-(1-甲基乙基)-1,3,4-噻二唑-2(3H)-酮(化合物6);
3-[2,4-二氯-5-(2-丙炔氧基)苯基]-5-乙基-1,3,4-噻二唑-2(3H)-酮(化合物7);
3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-5-乙基-1,3,4-噻二唑-2(3H)-酮(化合物8);
3-[2,4-二氯-5-(2-丙炔氧基)苯基]-5-(1-甲基环丙基)-1,3,4-噻二唑-2(3H)-酮(化合物9);
3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-5-(1-甲基环丙基)-1,3,4-噻二唑-2(3H)-酮(化合物10);
(±)-3-[2,4-二氯苯基-5-(1-甲基-2-丙炔氧基)苯基]-5-(1,1-二甲基乙基)-1,3,4-噻二唑-2(3H)-酮(化合物11);
(±)-3-[4-氯-2-氟-5-(1-甲基-2-丙炔氧基)苯基]-5-(1,1-二甲基乙基)-1,3,4-噻二唑-2(3H)-酮(化合物12);
(±)-5-环丙基-3-[2,4-二氯-5-(1-甲基-2-丙炔氧基)苯基]-1,3,4-噻二唑-2(3H)-酮(化合物13);
(±)-5-环丙基-3-[4-氯-2-氟-5-(1-甲基-2-丙炔氧基)苯基]-1,3,4-噻二唑-2(3H)-酮(化合物14);
(±)-3-[2,4-二氯-5-(1-甲基-2-丙炔氧基)苯基]-5-(1-甲基乙基)-1,3,4-噻二唑-2(3H)-酮(化合物15);
(±)-3-[4-氯-2-氟-5-(1-甲基-2-丙炔氧基)苯基]-5-(1-甲基乙基)-1,3,4-噻二唑-2(3H)-酮(化合物16);
(±)-3-[2,4-二氯-5-(1-甲基-2-丙炔氧基)苯基]-5-乙基-1,3,4-噻二唑-2(3H)-酮(化合物17);
(±)-3-[4-氯-2-氟-5-(1-甲基-2-丙炔氧基)苯基]-5-乙基-1,3,4-噻二唑-2(3H)-酮(化合物18);
(±)-3-[2,4-二氯-5-(1-甲基-2-丙炔氧基)苯基]-5-(1-甲基环丙基)-1,3,4-噻二唑-2(3H)-酮(化合物19);
(±)-3-[4-氯-2-氟-5-(1-甲基-2-丙炔氧基)苯基]-5-(1-甲基环丙基)-1,3,4-噻二唑-2(3H)-酮(化合物20)。
具有通式(I)的芳基噻二唑酮可通过各种方法常规制备。
一种制备式(I)芳基噻二唑酮的方法包含式(II)的硫代酰肼与碳酰氯、氯甲酸三氯甲基酯或碳酸双(三氯甲基)酯的反应,反应在惰性有机溶剂存在或不存在,优选存在,温度范围为+20℃至混合物自身的沸点,任选存在有机或无机碱的条件下进行。
可用于本发明的惰性有机溶剂,例如为氯代烃类如二氯甲烷、氯仿、1,2-二氯乙烷等;芳香烃类如苯、甲苯、二甲苯、氯苯等;醚类如乙醚、四氢呋喃、二甲氧基乙烷、二氧杂环己烷等;酯类如乙酸乙酯等。
可用于本发明的有机碱,例如为三乙胺、吡啶、4-二甲胺基吡啶等。
可用于本发明的无机碱,例如为碳酸氢钠等。
式(II)的硫代酰肼可通过五硫化二磷或Lawesson试剂处理相应的酰肼而制备,参见下列文献:“氟化学杂志(Journal of FluorineChemistry)”(1978)第2卷,第1-21页,或“化学快报(ChemistryExpress)”(1991)第6卷,第411-414页。
除草剂(b)均是现有技术已知的并且可从商业途径购得的产品。上文所列的除草剂(b)均指出了其通用名或代码,在下列文献中有具体描述,如:“农用化学品手册(The Agrochemicals Handbook)(1994)”,第3版,皇家化学学会(Royal Society of Chemistry);或“AG ChemNew Compound Review”,第13卷(1995),第14卷(1996),第15卷(1997),W.L.Hopkins,AG Chem Information Service;或“布赖顿作物保护会议-会刊(Brighton Crop ProtectionConference-Proceedings)”,(1991)、(1993)和(1995)。
就上文所列的已知除草剂(b)的使用而言,本发明除草剂组合物的使用已证明是有利的。这些通常具有植物毒性的除草剂(b)由于至少一种式(I)芳基噻二唑酮的存在,降低了它们使用的剂量,或/和扩大了活性谱。
在防治各种杂草时,包括单子叶杂草和双子叶杂草,本发明的除草剂组合物进行芽前处理和芽后处理均具有独特的效果。同时,这些除草剂组合物对重要的农业作物显示出了减小药害或根本没有药害的效果,因而可将它们用于农田中选择性防治杂草。
本发明除草剂组合物可有效防治的杂草实例有:苘麻、欧泽泻、大穗看麦娘、苋属、豚草、大阿米(Amnimaius)、风剪股颖、野燕麦、雀麦属、荠、钝叶决明、藜、旋花(Convolvulus sepium)、莎草属、曼陀罗、马唐、稗属、蟋蟀草、猪殃殃、裂叶老鹳草、Heleocharisavicularis、Heteranthera spp.、番著属、黑麦草属、母菊属、鸭舌草、黍属、虞美人、菜豆(Phaseolus aureus)、早熟禾属、蓼属、马齿苋、节节菜、矮慈姑、莞草属、高田菁、狗尾草、刺黄花捻、高粱属、龙葵、繁缕、婆婆纳属、蚕豆、田堇菜、苍耳属等。
本发明除草剂组合物在农业上使用的剂量下对于一种或多种重要的农业作物没有毒性,这些作物如:玉米(Zeamais)、小麦(Triticumspp.)、大豆(Glicine max)、水稻(Oryza sativa)等。
式(I)的芳基噻二唑酮与上述的除草剂(b)可根据各种因素以任何比例配制成除草剂组合物,这些因素如:混合物成分的数目和类型、欲保护的作物、欲防除的杂草、草害程度、施用方法、土壤类型等。
本发明的除草剂组合物中,式(I)芳基噻二唑酮的重量通常在1g/ha至5kg/ha,优选10g/ha至500g/ha的范围之间。
本发明的除草剂组合物中,式(I)芳基噻二唑酮与上文所列的除草剂(b)的重量比通常在99.9∶0.1至0.1∶99.9之间,优选99∶1至1∶99之间。
在玉米、谷类或大豆的栽培过程中进行芽前处理时,本发明组合物除了含有式(I)的芳基噻二唑酮之外,还含有一种或多种选自上文所列的下述除草剂(b),根据作物以及欲防除的杂草,选自:乙草胺、三氟羧草醚、苯草醚、甲草胺、莠灭净、莠去津、甲羧除草醚、仲丁灵、草灭畏、异噁草酮、氯秀隆、绿麦隆、绿黄隆、氰草津、环丙嘧磺隆、乙酰甲草胺、吡氟酰草胺、二甲吩草胺、双苯酰草胺、甘草津、氯乙氟灵、丙炔氟草胺、乙羧氟草醚、胺草唑、氟咯草酮、呋草酮、氯吡嘧磺隆、灭草喹、咪草烟、异丙隆、异噁草胺、噁氟酮(isoxaflutone(RPA 201772))、利谷隆、吡唑胺、甲基苯噻隆、秀谷隆、异丙甲草胺、甲氧隆、嗪草酮、甲磺隆、绿谷隆、哒草伏、坪草丹、噁草酮、乙氧氟草醚、二甲戊乐灵、甘扑津、毒草胺、苄草丹、乙嗪草酮、甲磺草胺、特丁净、氟硫胺(fluthiamide(BAY FOE 5043))、野燕畏、醚苯磺隆、氟乐灵。
在水稻栽培过程中进行处理时,本发明组合物除了含有式(I)的芳基噻二唑酮之外,还含有一种或多种选自上文所列的除草剂(b),根据施用方法以及欲防除的杂草,选自:三氟羧草醚、莎稗磷、四唑嘧磺隆(DPX-A8947)、苄嘧磺隆、地散磷、吡草酮、甲羧除草醚、双草醚(KHI-2023)、溴丁酰草胺、丁草胺、丁烯草胺、仲丁灵、苯酮唑(CH-900)、甲氧除草醚、草枯醚、氯苯胺灵、环庚草醚、醚磺隆、稗草胺、除草隆(cumyluron)、环丙嘧磺隆(AC-322,140)、杀草隆、敌草腈、乙酰甲草胺、哌草丹、二甲丙乙净、戊草丹、乙氧嘧磺隆(HOE095404)、氯乙氟灵、氯吡嘧磺隆(NC-319)、苯噻酰草胺、甲基杀草隆、禾草敌、萘丙胺、oxadiargyl、恶草酮、oxaziciclomefone(MY-100)、戊噁草酮(pentoxazone)、哌草磷、丙草胺、敌稗、吡唑特、吡嘧磺隆、苄草唑、pyribenzoxim(LGC-40863)、稗草丹、嘧草醚(Pyriminobac-methyl(KIH-6127))、二氯喹啉酸、西草净、噻吩草胺(NSK-850)、禾草丹、仲草丹。
农业上实际应用时,本发明的除草剂组合物制成合适的剂型进行使用通常更为有利。有两种制剂方法:一种是式(I)的芳基噻二唑酮与一种或多种选自上文所列的除草剂(b)混合制成所需的组合物,一种是式(I)的芳基噻二唑酮与一种或多种选自上文所列的除草剂(b)单独制剂,使用时适量混合形成组合物。
组合物可以采用各种剂型:干粉剂、可湿性粉剂、浓乳剂、乳剂、微乳剂、多相悬浮剂、凝胶、糊剂、薄片剂、溶液、悬浮剂、丸剂、片剂、薄膜等。组合物根据特定的用途选择不同的剂型。
组合物根据已知的方法制备而成,如:用溶剂介质和/或固体稀释剂稀释或溶解活性物质,任选在表面活性剂存在的条件下进行。
当然,除水之外,适用的液体稀释剂还有各种溶剂如N,N-二甲基甲酰胺;二甲亚砜;N-烷基吡咯烷酮类(N-甲基吡咯烷酮等);脂族烃类(己烷、环己烷等);芳烃类(二甲苯类,烷基苯混合物、烷基萘等);氯代芳烃类(氯苯);醇类(甲醇、丙醇、丁醇、辛醇、环己醇、癸醇、四氢糠醇等);二醇类(乙二醇、丙二醇等);酮类(丙酮、环己酮、2-庚酮、苯乙酮、异佛尔酮、4-羟基-4-甲基-2-戊酮等);酯类(乙酸异丁酯等);植物油或矿物油;或它们的混合物。
适用的固体惰性稀释剂或载体有:高岭土、矾土、硅镁土、膨润土、蒙脱石、方解石、白云石、白垩、浮石、石英、砂石、二氧化硅、滑石、海泡石、硅藻土、淀粉、纤维素、蔗糖、尿素、碳酸钙、碳酸钠、碳酸氢钠、硫酸钠等。
可使用的表面活性剂有:非离子型乳化和润湿剂,例如:聚乙氧基化脂肪醇和聚乙氧基化环脂肪醇、聚乙氧基化烷基酚、聚乙氧基化脱水山梨糖醇脂肪酸酯、聚氧乙烯与聚丙二醇,或与乙二胺聚丙二醇,或与烷基聚丙二醇的水溶性聚加合物等;阴离子型乳化和润温剂,例如:C10-C22脂肪酸的金属盐或铵盐、或烷基-芳基磺酸盐、或烷基磺酸盐、或烷基硫酸盐、或苯并咪唑磺酸盐等;阳离子型乳化和润湿剂,例如:C8-C22烷基铵的季铵盐等。
上述组合物也可含有分散剂(如木质素及其盐、纤维素衍生物、海藻酸盐等)、稳定剂(如抗氧化剂、紫外线吸收剂等)、泡沫抑制剂(如硅油等)、增稠剂。
如果需要,可加入其他与本发明除草剂组合物相容的活性成分,例如:其他除草剂、杀真菌剂、植物生长调节剂、抗生素、杀虫剂、肥料。
本发明的除草剂组合物通常含有0.1%-99%(重量),优选1%-95%(重量)的式(I)芳基噻二唑酮与一种或多种选自上文所列的除草剂(b)的混合物,1%-99.9%(重量)的液体或固体稀释剂,0%-25%(重量)、优选0.1%-20%(重量)的表面活性剂。
下面的实施例仅起解释作用,不限制本发明的范围。实施例13-[2,4-二氯-5-(2-丙炔氧基)苯基]-5-(1,1-二甲基乙基)-1,3,4-噻二唑-2(3H)-酮(化合物1)
在氮气氛下,将0.5克(2.5毫摩尔)氯甲酸三氯甲基酯加入到1.65克(5毫摩尔)N’-[2,4-二氯-5-(2-丙炔氧基)苯基]-N-硫代新戊酰肼于25毫升二噁烷的溶液中。
所得混合物在室温下搅拌3小时。然后,将该混合物倾入250毫升水中,用乙醚萃取(3×10ml)。用氯化钠饱和溶液洗涤所得有机相直至其变为中性,用硫酸钠干燥,之后用旋转蒸发器浓缩。
所得粗产品用洗脱液为正己烷/乙酸乙酯(9∶1)的硅胶色谱纯化。获得1.4克固体产物,熔点为92℃,即为化合物1。实施例2
按实施例1中描述的步骤制备下面的化合物:
3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-5-(1,1-二甲基乙基)-1,3,4-噻二唑-2(3H)-酮(化合物2;熔点73-74℃);
5-环丙基-3-[2,4-二氯-5-(2-丙炔氧基)苯基]-1,3,4-噻二唑-2(3H)-酮(化合物3;熔点99-101℃);
5-环丙基-3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-1,3,4-噻二唑-2(3H)-酮(化合物4;粘稠油状物);
3-[2,4-二氯-5-(2-丙炔氧基)苯基]5-(1-甲基乙基)-1,3,4-噻二唑-2(3H)-酮(化合物5;熔点55-57℃);
3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-5-(1-甲基乙基)-1,3,4-噻二唑-2(3H)-酮(化合物6;粘稠油状物);
3-[2,4-二氯-5-(2-丙炔氧基)苯基]-5-乙基-1,3,4-噻二唑-2(3H)-酮(化合物7;熔点100-101℃);
3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-5-乙基-1,3,4-噻二唑-2(3H)-酮(化合物8;熔点93-94℃);
3-[2,4-二氯-5-(2-丙炔氧基)苯基]-5-(1-甲基环丙基)-1,3,4-噻二唑-2(3H)-酮(化合物9;熔点117-119℃);
3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-5-(1-甲基环丙基)-1,3,4-噻二唑-2(3H)-酮(化合物10;熔点95-97℃)。实施例3芽前处理除草活性的测定
芽前处理时,本发明组合物的除草活性和植物毒性根据下面的步骤进行测定:
准备含有砂土的盆(直径10cm,高度10cm),每盆内种植杂草或作物。
将试验的盆分成4组,每组中各种杂草和作物有5盆。
播种24小时后,每个盆用小的淋水器浇湿。浇水1小时后,第-组盆用含有试验组合物、丙酮(10%体积)和吐温20(0.5%)的水丙酮分散液处理。
第二组盆用含有与组合物中量相同的芳基噻二唑酮、丙酮(10%体积)和吐温20(0.5%)的水丙酮分散液处理。
第三组盆用含有与组合物中量相同的已知除草剂、丙酮(10%体积)和吐温20(0.5%)的水丙酮分散液处理。
第四组盆用含有丙酮(10%体积)和吐温20(0.5%)的水丙酮分散液处理,作为对照。
处理后,所有的盆均一致地每两天浇1次水,控制使其处于下列环境条件下:
温度:24℃;
相对温度:60%;
光周期:16小时;
光照强度:10000勒。
处理28天后,测定组合物的除草活性和植物毒性,并与单一组分处理及对照处理进行比较。
在下面的表1中,分作物描述了式(I)芳基噻二唑酮(组分1)与已知除草剂(组分2)的组合物,与单一组分的加合效果相比,具有较好的除草活性和/或降低了植物毒性。
表1
*实施例1描述的化合物。
作物 | 化合物编号(组分1) | 已知除草剂(组分2) |
玉米 | 1* | 乙草胺、苯草醚、甲草胺、莠灭净、莠去津、BAY FOE 5043、呋草黄、甲羧除草醚、丁草特(buthylate)、异噁草酮、氰草津、乙酰甲草胺、二甲吩草胺、茵草敌、乙丁烯氟灵(ethalfluralon)、唑嘧磺草胺、氯吡嘧磺隆、印丹丰、噁氟酮、利谷隆、甲基苯噻隆、秀谷隆、异丙甲草胺、磺草唑胺、绿谷隆、坪草丹、乙氧氟草醚、二甲戊乐灵、毒草胺、特丁津、野燕畏、灭草敌。 |
小麦/大麦 | 1* | 苯草醚、BAY FOE 5043、甲羧除草醚、环丙嘧隆、氯磺隆、缘麦隆、吡氟酰草胺、乙氧嘧磺隆、乙羧氟草醚、胺草唑、呋草酮、印丹丰、异丙唑、异丙隆、异噁草胺、KPP300、KPP 421、利谷隆、甲基苯噻隆、甲氧隆、MON 37500、绿谷隆、草不隆、坪草丹、乙氧氟草醚、二甲戊乐灵、苄草丹、环草隆、野燕畏、氟乐灵、UCC 4243。 |
水稻 | 1* | 莎稗磷、fentrazamide(BAY YRC 2388)、BAY FOE 5043、呋草黄、甲羧除草醚、苯酮唑、甲氧除草醚、草枯醚、氯苯胺灵、环庚草醚、环丙嘧磺隆、杀草隆、哌草丹、二甲丙乙净、戊草丹、ethabenzanid、乙氧嘧磺隆、乙羧氟草醚、印丹丰、苯噻酰草胺、禾草敌、oxadiargyl、噁草酮、oxaziciclomefone、戊噁草酮、哌草磷、丙草胺、吡唑特、苄草唑、稗草丹、吡嘧磺隆、二氯喹啉酸、西草净、禾草丹、仲草丹。 |
大豆 | 1* | BAY FOE 5043、甲羧除草醚、氯秀隆、氯嘧磺隆、氯苯胺灵、敌草索、异噁草酮、二甲吩草胺、乙丁烯氟灵、唑嘧磺草胺、丙炔氟草胺、乙羧氟草醚、氟磺胺草醚、灭草喹、咪草烟、印丹丰、利谷隆、异丙甲草胺、萘草胺、哒草伏、坪草丹、氨黄乐灵、乙氧氟草醚、毒草胺、甲磺草胺、噻唑烟酸、氟乐灵、灭草敌。 |
棉花 | 1* | 氯苯胺灵、敌草索、恶唑隆、DPXT 5975、乙丁烯氟灵、氟草隆、印丹丰、利谷隆、异丙甲草胺、哒草伏、坪草丹、氨磺乐灵、乙氧氟草醚、扑草净、毒草胺、噻唑烟酸。 |
向日葵 | 1* | 苯草醚、氯秀隆、氯苯胺灵、乙丁烯氟灵、氟咯草酮、呋草酮、利谷隆、异丙甲草胺、野燕畏。 |
甘蔗 | 1* | 乙草胺、除草定、氰草津、二甲丙乙净、乙氧嘧磺隆、氟草隆、噁氟酮、利谷隆、异丙甲草胺、oxadiargyl、毒草胺、甲磺草胺、丁噻隆、therbacil、噻唑烟酸。 |
Claims (11)
R代表直链或支链C1-C6烷基或卤代烷基;或C3-C6环烷基或卤代环烷基;所述的烷基或卤代烷基、环烷基或卤代环烷基可任选被直链或支链C1-C3烷基取代;
X代表卤素原子如氯或氟;
Y代表卤素原子如氯、氟、溴或碘;直链或支链C1-C4烷基或卤代烷基;直链或支链C1-C4烷氧基或卤代烷氧基;
R1代表卤素原子或甲基;
(b)一种或多种选自下列的除草剂:草灭畏、敌草索、麦草畏、萘草胺、草芽平、二氯吡啶酸、二氟草灭(diflufenzopyr(SAN 835 H))、氟硫草定、氨氯吡啶酸、噻唑烟酸(MON 13200)、二氯喹啉酸、氯甲喹啉酸、印丹丰(indanofan(MK-243))、草除灵、氯甲丹、茅草枯、茵多酸、氟燕灵、麦草氟甲酯、四氟丙酸、芴丁酯、三氯醋酸钠、溴丁酰草胺、氯硫酰草胺、吡氟酰草胺、双苯酰草胺、ethabenzanid(HW52)、异噁草胺、苯噻酰草胺、庚酰草胺、甲氯酰草胺、敌稗、炔苯酰草胺、牧草胺、氟硫胺(fluthiamide(BAY FOE 5043))、炔草酯、稗草胺、氰氟草酯、2,4-滴、2,4-滴丁酸、2,4-滴丙酸、精2,4-滴丙酸、禾草灵、恶唑禾草灵、精恶唑禾草灵、吡氟禾草灵、精吡氟禾草灵、氯氟吡氧乙酸、吡氟氯禾灵、氟吡甲禾灵、异恶草醚、二甲四氯、二甲四氯乙硫酯(MCPA-thioethyl)、二甲四氯丁酸、二甲四氯丙酸、精二甲四氯丙酸、萘丙胺、敌草胺、恶草酸、喹禾灵、精喹禾灵、三氯吡氧乙酸、喹禾糖酯、溴酚肟、溴苯腈、敌草腈、碘苯腈、敌草快、百草枯、磺草灵、丁草敌、双酰草胺、氯炔灵、氯苯胺灵、环草敌、甜菜安、哌草丹、茵草敌、戊草丹、稗草丹、禾草敌、坪草丹、克草敌、甜菜宁、苯胺灵、苄草丹、稗草丹、禾草丹、仲草丹、野燕畏、灭草敌、禾草灭、butroxydim、烯草酮、噻草酮、稀禾啶、磺草酮、三甲苯草酮、乙草胺、甲草胺、丁草胺、丁烯草胺、乙酰甲草胺、二甲草胺、二甲吩草胺、吡唑胺、异丙甲草胺、丙草胺、毒草胺、异丙草胺、杀草胺(tenylchlor(NSK-850))、三氟羧草醚、苯草醚、甲羧除草醚、甲氧除草醚、草枯醚、athoxyfen-ethyl(HC-252)、乙羧氟草醚、氟除草醚、氟磺胺草醚、呋氧草醚、乳氟禾草灵、氟草醚、乙氧氟草醚、乙丁氟灵、仲丁灵、dintramide、乙丁烯氟灵、氯乙氟灵、异丙乐灵、氨磺乐灵、二甲戊乐灵、氨基丙氟灵、氟乐灵、地乐酚、地乐酯、特乐酚、杀草强、呋草黄、灭草松、吡草酮、苯酮唑、carfentrazone-ethyl(F-8426)、氯草敏、环庚草醚、异噁草酮、野燕枯、乙氧呋草黄、pyraflufen-ethyl(ET-751)、氟烯草酸、丙炔氟草胺、flumipropin、胺草唑、氟啶草酮、氟咯草酮、呋草酮、嗪草酸、噁氟酮(isoxaflutone(RPA 201772))、灭草唑、氟氯草胺、哒草伏、oxadiargyl、恶草酮、oxaziclomefone(MY-100)、戊噁草酮(pentoxazone(KPP-314))、吡唑特、苄草唑、哒草特、甲磺草胺、thidiazimin、莎稗磷、地散磷、双丙氨酰膦、抑草磷、膦铵素、草铵膦、草甘膦、磺草膦、哌草磷、咪草酸、甲咪唑烟酸、imazamox(AC-299,263)、咪唑烟酸、灭草喹、咪草烟、双草醚、pyribenzoxim(LGC-40863)、嘧草醚、嘧草硫醚、嘧草胺、cloransulam-methyl(XDE-565)、diclosulam(XDE-564)、唑嘧磺草胺、磺草唑胺、酰嘧磺隆、四唑嘧磺隆、苄嘧磺隆、氯嘧磺隆、氯磺隆、醚磺隆、环丙嘧磺隆、胺苯磺隆、乙氧嘧磺隆、啶嘧磺隆、flupyrsufuron(DPX-KE459)、氯吡嘧磺隆、唑吡嘧磺隆、甲黄隆、唑嘧磺隆、烟嘧磺隆、噁磺隆(oxasulfuron(CGA-277476))、氟嘧磺隆、氟磺隆、吡嘧磺隆、砜嘧磺隆、甲嘧磺隆、草磺隆(sulfosulfuron(MON-37500))、噻吩磺隆、醚苯磺隆、苯磺隆、氟胺磺隆、莠灭净、莠去津、叠氮净、氰草津、敌草净、二甲丙乙净、异丙净、甘草津、甲氧丙净、甘扑津、扑灭通、扑草净、扑灭津、西玛津、西草净、特丁通、特丁津、特丁净、triaziflam(IDH-1105)、草达津、乙嗪草酮、环嗪酮、苯嗪草酮、嗪草酮、除草定、环草啶、特草定、苯噻隆、氯秀隆、枯草隆、绿麦隆、除草隆(cumyluron(JC-940))、杀草隆、枯莠隆、恶唑隆、敌草隆、磺噻隆、非草隆、氟草隆、异丙隆、异恶隆、利谷隆、甲基苯噻隆、甲基杀草隆、吡喃隆、秀谷隆、甲氧隆、绿谷隆、草不隆、环草隆、丁噻隆、噻氟隆、异丙唑(isopropazol(JV 485))、KPP 300、KPP 421、BAY YRL 2388、DPXT 5975、azafenidin。
2、根据权利要求1的除草剂组合物,其中所述的式(I)芳基噻二唑酮为:
-3-[2,4-二氯-5-(2-丙炔氧基)苯基]-5-(1,1-二甲基乙基)-1,3,4-噻二唑-2(3H)-酮;
-3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-5-(1,1-二甲基乙基)-1,3,4-噻二唑-2(3H)-酮;
-5-环丙基-3-[2,4-二氯-5-(2-丙炔氧基)苯基]-1,3,4-噻二唑-2(3H)-酮;
-5-环丙基-3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-1,3,4-噻二唑-2(3H)-酮;
-3-[2,4-二氯-5-(2-丙炔氧基)苯基]-5-(1-甲基乙基)-1,3,4-噻二唑-2(3H)-酮;
-3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-5-(1-甲基乙基)-1,3,4-噻二唑-2(3H)-酮;
-3-[2,4-二氯-5-(2-丙炔氧基)苯基]-5-乙基-1,3,4-噻二唑-2(3H)-酮;
-3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-5-乙基-1,3,4-噻二唑-2(3H)-酮;
-3-[2,4-二氯-5-(2-丙炔氧基)苯基]-5-(1-甲基环丙基)-1,3,4-噻二唑-2(3H)-酮;
-3-[4-氯-2-氟-5-(2-丙炔氧基)苯基]-5-(1-甲基环丙基)-1,3,4-噻二唑-2(3H)-酮;
-(±)-3-[2,4-二氯苯基-5-(1-甲基-2-丙炔氧基)苯基]-5-(1,1-二甲基乙基)-1,3,4-噻二唑-2(3H)-酮;
-(±)-3-[4-氯-2-氟-5-(1-甲基-2-丙炔氧基)苯基]-5-(1,1-二甲基乙基)-1,3,4-噻二唑-2(3H)-酮;
-(±)-5-环丙基-3-[2,4-二氯-5-(1-甲基-2-丙炔氧基)苯基]-1,3,4-噻二唑-2(3H)-酮;
-(±)-5-环丙基-3-[4-氯-2-氟-5-(1-甲基-2-丙炔氧基)苯基]-1,3,4-噻二唑-2(3H)-酮;
-(±)-3-[2,4-二氯-5-(1-甲基-2-丙炔氧基)苯基]-5-(1-甲基乙基)-1,3,4-噻二唑-2(3H)-酮;
-(±)-3-[4-氯-2-氟-5-(1-甲基-2-丙炔氧基)苯基]-5-(1-甲基乙基)-1,3,4-噻二唑-2(3H)-酮;
-(±)-3-[2,4-二氯-5-(1-甲基-2-丙炔氧基)苯基]-5-乙基-1,3,4-噻二唑-2(3H)-酮;
-(±)-3-[4-氯-2-氟-5-(1-甲基-2-丙炔氧基)苯基]-5-乙基-1,3,4-噻二唑-2(3H)-酮;
-(±)-3-[2,4-二氯-5-(1-甲基-2-丙炔氧基)苯基]-5-(1-甲基环丙基)-1,3,4-噻二唑-2(3H)-酮;
-(±)-3-[4-氯-2-氟-5-(1-甲基-2-丙炔氧基)苯基]-5-(1-甲基环丙基)-1,3,4-噻二唑-2(3H)-酮。
3、根据权利要求1或2的除草剂组合物,其中式(I)芳基噻二唑酮的重量在1g/ha至5kg/ha之间。
4、根据权利要求3的除草剂组合物,其中式(I)芳基噻二唑酮的重量在10g/ha至500g/ha之间。
5、根据上述权利要求任一项的除草剂组合物,其中式(I)芳基噻二唑酮与除草剂(b)的重量比在99.9∶0.1至0.1∶99.9之间
6、根据权利要求5的除草剂组合物,其中式(I)芳基噻二唑酮与除草剂(b)的重量比在99∶1至1∶99之间。
7、根据上述权利要求任一项的除草剂组合物,用于玉米、谷类或大豆芽前处理时,其中所述的除草剂(b)选自:乙草胺、三氟羧草醚、苯草醚、甲草胺、莠灭净、莠去津、甲羧除草醚、仲丁灵、草灭畏、异噁草酮、氯秀隆、绿麦隆、绿黄隆、氰草津、环丙嘧磺隆、乙酰甲草胺、吡氟酰草胺、二甲吩草胺、双苯酰草胺、甘草津、氯乙氟灵、丙炔氟草胺、乙羧氟草醚、胺草唑、氟咯草酮、呋草酮、氯吡嘧磺隆、灭草喹、咪草烟、异丙隆、异噁草胺、噁氟酮(isoxaflutone(RPA201772))、利谷隆、吡唑胺、甲基苯噻隆、秀谷隆、异丙甲草胺、甲氧隆、嗪草酮、甲磺隆、绿谷隆、哒草伏、坪草丹、噁草酮、乙氧氟草醚、二甲戊乐灵、甘扑津、毒草胺、苄草丹、乙嗪草酮、甲磺草胺、特丁净、氟硫胺(fluthiamide(BAY FOE 5043))、野燕畏、醚苯磺隆、氟乐灵。
8、根据上述权利要求任一项的除草剂组合物,用于水稻栽培芽前处理时,其中除草剂(b)选自:三氟羧草醚、莎稗磷、四唑嘧磺隆(DPX-A8947)、苄嘧磺隆、地散磷、吡草酮、甲羧除草醚、双草醚(KHI-2023)、溴丁酰草胺、丁草胺、丁烯草胺、仲丁灵、苯酮唑(CH-900)、甲氧除草醚、草枯醚、氯苯胺灵、环庚草醚、醚磺隆、稗草胺、除草隆(cumyluron)、环丙嘧磺隆(AC-322,140)、杀草隆、敌草腈、乙酰甲草胺、哌草丹、二甲丙乙净、戊草丹、乙氧嘧磺隆(HOE0954041)、氯乙氟灵、氯吡嘧磺隆(NC-319)、苯噻酰草胺、甲基杀草隆、禾草敌、萘丙胺、oxadiargyl、恶草酮、oxaziciclomefone(MY-100)、戊噁草酮(pentoxazone)、哌草磷、丙草胺、敌稗、吡唑特、吡嘧磺隆、苄草唑、pyribenzoxim(LGC-40863)、稗草丹、嘧草醚(Pyriminobac-methyl(KIH-6127))、二氯喹啉酸、西草净、噻吩草胺(NSK-850)、禾草丹、仲草丹。
9、根据上述权利要求任一项的除草剂组合物,含有液体稀释剂、固体稀释剂、表面活性剂、分散剂、稳定剂、泡沫抑制剂、增稠剂。
10、根据上述权利要求任一项的除草剂组合物,其中还含有其他除草剂、杀真菌剂、植物生长调节剂、抗生素、杀虫剂、肥料。
11、根据上述权利要求任一项的除草剂组合物,其中以重量计含有0.1%-99%的式(I)芳基噻二唑酮与一种或多种选自上文所列的除草剂(b)的混合物,1%-99.9%的液体或固体稀释剂,以及0%-25%的表面活性剂。
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ATE294501T1 (de) * | 1998-07-16 | 2005-05-15 | Bayer Cropscience Gmbh | Herbizide mittel |
JP2000063216A (ja) * | 1998-08-12 | 2000-02-29 | Sumitomo Chem Co Ltd | 除草剤組成物 |
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KR20030089884A (ko) * | 2002-05-20 | 2003-11-28 | 오세헌 | 잔디밭의 잡초 방제방법 |
UA78071C2 (en) * | 2002-08-07 | 2007-02-15 | Kumiai Chemical Industry Co | Herbicidal composition |
AR071339A1 (es) * | 2008-02-05 | 2010-06-16 | Arysta Lifescience North Ameri | Formulacion solida de compuesto activo de baja fusion |
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- 1998-06-02 US US09/424,984 patent/US6632775B1/en not_active Expired - Fee Related
- 1998-06-02 ID IDW991523A patent/ID22931A/id unknown
- 1998-06-02 DE DE69802928T patent/DE69802928T2/de not_active Expired - Fee Related
- 1998-06-02 ES ES98929436T patent/ES2167905T3/es not_active Expired - Lifetime
- 1998-06-02 JP JP50158299A patent/JP2002502408A/ja active Pending
- 1998-06-02 WO PCT/EP1998/003472 patent/WO1998054967A1/en active IP Right Grant
- 1998-06-02 IL IL13294998A patent/IL132949A/xx not_active IP Right Cessation
- 1998-06-02 KR KR1019997011398A patent/KR100354146B1/ko not_active IP Right Cessation
- 1998-06-02 BR BR9809531-5A patent/BR9809531A/pt active Search and Examination
- 1998-06-02 PT PT98929436T patent/PT986303E/pt unknown
- 1998-06-02 CN CN98805742A patent/CN1259013A/zh active Pending
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Also Published As
Publication number | Publication date |
---|---|
PT986303E (pt) | 2002-04-29 |
KR20010013398A (ko) | 2001-02-26 |
AU7919198A (en) | 1998-12-21 |
KR100354146B1 (ko) | 2002-09-28 |
CA2292781C (en) | 2007-10-30 |
BR9809531A (pt) | 2000-06-20 |
ITMI971325A0 (zh) | 1997-06-05 |
ITMI971325A1 (it) | 1998-12-05 |
JP2002502408A (ja) | 2002-01-22 |
IT1292088B1 (it) | 1999-01-25 |
EP0986303B1 (en) | 2001-12-12 |
AU725736B2 (en) | 2000-10-19 |
CA2292781A1 (en) | 1998-12-10 |
WO1998054967A1 (en) | 1998-12-10 |
DE69802928T2 (de) | 2002-06-27 |
US6632775B1 (en) | 2003-10-14 |
ID22931A (id) | 1999-12-16 |
CU22867A3 (es) | 2007-03-23 |
EP0986303A1 (en) | 2000-03-22 |
IL132949A (en) | 2003-09-17 |
ES2167905T3 (es) | 2002-05-16 |
IL132949A0 (en) | 2001-03-19 |
DE69802928D1 (de) | 2002-01-24 |
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