CN1043891C - 氟苯并噻唑氧基乙酰胺及制法和作为除莠剂的用途 - Google Patents
氟苯并噻唑氧基乙酰胺及制法和作为除莠剂的用途 Download PDFInfo
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- CN1043891C CN1043891C CN93117278A CN93117278A CN1043891C CN 1043891 C CN1043891 C CN 1043891C CN 93117278 A CN93117278 A CN 93117278A CN 93117278 A CN93117278 A CN 93117278A CN 1043891 C CN1043891 C CN 1043891C
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- alkyl
- fluorine
- methyl
- arbitrarily
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- 238000002360 preparation method Methods 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000004009 herbicide Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 55
- 241000196324 Embryophyta Species 0.000 claims description 30
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 21
- -1 nitro, methyl Chemical group 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 14
- QVWCHVAUHZEAAT-UHFFFAOYSA-N 2-fluoro-1,3-benzothiazole Chemical compound C1=CC=C2SC(F)=NC2=C1 QVWCHVAUHZEAAT-UHFFFAOYSA-N 0.000 claims description 9
- KDTMGTGGRUOHKX-UHFFFAOYSA-N [O].FC=1SC2=C(N1)C=CC=C2 Chemical compound [O].FC=1SC2=C(N1)C=CC=C2 KDTMGTGGRUOHKX-UHFFFAOYSA-N 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005936 piperidyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- RZEDIWACEVCJKL-UHFFFAOYSA-N [O].FC1=CC=CC=2N=CSC21 Chemical compound [O].FC1=CC=CC=2N=CSC21 RZEDIWACEVCJKL-UHFFFAOYSA-N 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 abstract description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
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- 244000025254 Cannabis sativa Species 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- 239000003995 emulsifying agent Substances 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
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- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
- GQPCQNLKLWGDIX-UHFFFAOYSA-N 2-chloro-7-fluoro-1,3-benzothiazole Chemical compound FC1=CC=CC2=C1SC(Cl)=N2 GQPCQNLKLWGDIX-UHFFFAOYSA-N 0.000 description 3
- APDYWQKMHIRPBV-UHFFFAOYSA-N 4-fluoro-2-methylsulfonyl-1,3-benzothiazole Chemical compound C1=CC=C2SC(S(=O)(=O)C)=NC2=C1F APDYWQKMHIRPBV-UHFFFAOYSA-N 0.000 description 3
- RCIYHBWAAXQWTQ-UHFFFAOYSA-N 4-fluoro-3h-1,3-benzothiazole-2-thione Chemical compound FC1=CC=CC2=C1N=C(S)S2 RCIYHBWAAXQWTQ-UHFFFAOYSA-N 0.000 description 3
- QLXVZOOASLJRJM-UHFFFAOYSA-N 7-fluoro-3h-1,3-benzothiazole-2-thione Chemical compound FC1=CC=CC2=C1SC(S)=N2 QLXVZOOASLJRJM-UHFFFAOYSA-N 0.000 description 3
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- 239000013543 active substance Substances 0.000 description 3
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- ISIIQFDYFMPPOA-UHFFFAOYSA-N 2-chloro-6-fluoro-1,3-benzothiazole Chemical compound FC1=CC=C2N=C(Cl)SC2=C1 ISIIQFDYFMPPOA-UHFFFAOYSA-N 0.000 description 2
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 2
- PNEABRNAYDDYJK-UHFFFAOYSA-N 2-hydroxy-n-methyl-n-phenylacetamide Chemical compound OCC(=O)N(C)C1=CC=CC=C1 PNEABRNAYDDYJK-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
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- XTVIFVALDYTCLL-UHFFFAOYSA-N 2,3,5-trichloro-1h-pyridin-4-one Chemical compound ClC1=CNC(Cl)=C(Cl)C1=O XTVIFVALDYTCLL-UHFFFAOYSA-N 0.000 description 1
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- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 description 1
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- 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
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- FJSMZHRHSKLZBN-UHFFFAOYSA-N piperazine;toluene Chemical compound C1CNCCN1.CC1=CC=CC=C1 FJSMZHRHSKLZBN-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229930189914 platycodon Natural products 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
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- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
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- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
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- 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 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 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
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- LSJNBGSOIVSBBR-UHFFFAOYSA-N thionyl fluoride Chemical compound FS(F)=O LSJNBGSOIVSBBR-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- OUZALXBFAPAMJR-UHFFFAOYSA-N tributyl(4-hydroxybutyl)azanium Chemical compound CCCC[N+](CCCC)(CCCC)CCCCO OUZALXBFAPAMJR-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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Abstract
本发明涉及式(Ⅰ)的新的氟苯并噻唑氧基乙酰胺。其中R1和R2的定义同说明书。本发明还涉及制备式(Ⅰ)化合物的方法及新的中间产物,以及这类化合物作为除莠剂的应用。
Description
本发明涉及新的氟苯并噻唑氧基乙酰胺、其制备方法和制备该化合物时的新的中间体、以及该化合物作为除莠剂的用途。
某些苯并噻唑氧基乙酰胺,如N-甲基苯并噻唑氧基乙酰苯胺具有杀草特性业已公开(参见EP-A-5,501;US-A-4,509,971;US-A-4,784,682和US-A-4,833,243)。但是这些已知化合物的杀草活性并非总是完全令人满意的。
R1代表氢或一个任意取代的烷基、链烯基、炔基和芳烷基,
R2代表一个任意取代的烷基、链烯基、炔基、环烷基、环烯基、芳烷基、芳基、烷氧基、烯氧基或炔氧基,或
R1和R2与它们所连接的氮原子一起,形成一个任意取代的饱和或不饱和的氮杂环,该杂环还可含有其它的杂原子,并可与苯基稠合。
还发现,必要时在稀释剂、酸结合剂和催化剂存在下,通过通式(Ⅱ)的氟苯并噻唑(其中的X代表卤原子或烷基磺酰基),与通式(Ⅲ)的羟基乙酰胺(其中的R1和R2的定义同上)反应,可获得通式(Ⅰ)所示的新的氟苯并噻唑氧基乙酰胺。
最后,还发现通式(Ⅰ)所示的新的氟苯并噻唑氧基乙酰胺具有显著的除莠特性。
出人意外的是,本发明的式(Ⅰ)化合物对一些很难防治的杂草如稗草(Echinochloa crus galli),比起化学上相似的已知化合物(N-甲基苯并噻唑氧基乙酰苯胺)表现出强得多的除莠活性,在某些情况下对农作物(如稻子)具有非常好的耐受性。
本发明所涉及的式(Ⅰ)的优选化合物为:
R1代表氢、C1-C8烷基(该烷基可任意被氟、氯、氰基或C1-C4烷氧基取代)、C2-C8链烯基(该链烯基可任意被氟和/或氯取代)、C2-C8炔基或苄基,
R2代表C1-C8烷基(该烷基可任意被氟、氯、氰基或C1-C4烷氧基取代)、C2-C8链烯基(该链烯基可任意被氟和/或氯取代)、C2-C8炔基,C3-C6环烷基(该基团可任意被氯和/或C1-C3烷基取代)、C5-或C6-环烯基、苄基(该基团可任意被氟、氯和/或C1-C4烷基取代)、苯基(该基团可任意被氟、氯、溴、碘、氰基、硝基、C1-C4烷基、三氟甲基、C1-C4烷氧基和/或C1-C4烷硫基取代)、C1-C8烷氧基(该基团可任意被C1-C4烷氧基取代)或C3-C4链烯氧基,或者
R1和R2与它们所连接的氮原子一起,共同形成一个任意饱和或不饱和的五元到七元的氮杂环,该杂环可被C1-C3烷基一至三取代,并可任意与苯环稠合。
本发明中特制优选的式(Ⅰ)化合物为:
R1代表C1-C4烷基、烯丙基或炔丙基,
R2代表C1-C6烷基、C1-C2-烷氧基C1-C2-烷基、烯丙基、炔丙基、环戊基、环己基、环己烯基、苄基、苯基(该基团可任意被氟、氯、溴、氰基、硝基、甲基、乙基、三氟甲基、甲氧基或乙氧基取代)、C1-C6烷氧基或C1-C2-烷氧基C1-C2-烷氧基,或者
R1和R2与它们所连接的氮原子一起,代表哌啶基(该基团可被甲基和/或乙基任意地一至三取代)、吡咯烷基(该基团可被甲基和/或乙基任意地一至三取代)、全氢化氮杂基或1,2,3,4-四氢(异)喹啉基。
上述对各基团的一般和优选范围的定义和解释相应地也适用于最终产物和起始原料及中间体。这些基团的定义可以以希望的任何方式互相结合,即也可将不同的优选范围内的定义结合在一起。
按本发明,用于制备式(Ⅰ)化合物的起始反应物的氟苯并噻唑,其一般定义如式(Ⅱ)所示。
式(Ⅱ)中,x优选代表氟、氯或溴以及C1-C4烷磺酰基,特别是氯或甲基磺酰基。
除2,6-二氟-苯并噻唑和2-氯-6-氟-苯并噻唑(见Org.Magn.Reson.7(1975),84-85;Chem.Abstracts 83:113186X)外,文献中还未见有其它的式(Ⅱ)的起始反应物。因此,除了上面提到的两种已知化合物外,式(Ⅱ)的作为新的起始反应物,也是本发明的一个主题。
可提及的式(Ⅱ)的新化合物实例有:
2-氯-4-氟-苯并噻唑,2-氯-5-氟-苯并噻唑,2-氯-7-氟-苯并噻唑,2-甲基磺酰基-4-氟-苯并噻唑,2-甲基磺酰基-5-氟-苯并噻唑,2-甲基磺酰基-6-氟-苯并噻唑和2-甲基磺酰基-7-氟-苯并噻唑。
通式(Ⅱ)的氟苯并噻唑可通过下面的反应获得:
(a)当x为卤素时,将通式(Ⅳ)的2-氨基-氟苯并噻唑
J. Chemn. Soc. C 1969, 268-272; J.
Heterocycl. Chem. 18 (1981), 759-761; Synthet.
Commun.17(1987),229-240;EP-A 282971;在温度为-10℃至+60℃的条件下与重氮化剂和卤化剂(如亚硝酸钠,盐酸和铜粉)反应(见制备实施例)。
式(Ⅱ)的氟苯并噻唑也可通过下面的反应获得:
(b)当x为卤素时,将通式(Ⅴ)的2-巯基-氟苯并噻唑必要时在反应辅助剂(如二甲基甲酰胺)存在下,在0℃-100℃与卤化剂(如亚硫酰氯)反应(见制备实施例);或者
(c)当x为烷磺酰基时,必要时在合适的酸结合剂(如氢氧化钠)和稀释剂(如水)存在下,在-10℃至100℃,将式(Ⅴ)的2-巯基-氟苯并噻唑与烷化剂(如甲基碘)反应,如此获得的烷基化产物必要时在合适的反应辅助剂(如甲酸,硫酸和钼酸铵)存在下,在0℃至50℃与氧化剂(如过氧化氢)反应(见制备实施例)。
式(Ⅴ)的2-巯基-氟苯并噻唑是已知的,和/或可通过已知的方法直接制备[见DE-OS德国公布的专利说明书)3,008,225;美国专利4,873,346;制备实施例]。
按本发明,用于制备式(Ⅰ)化合物的另一种起始反应物羟基乙酰胺,其一般定义如式(Ⅲ)所示。
式(Ⅲ)中,R1和R2所优选或特别优选代表的基团是本发明对式(Ⅰ)化合物的描述中R1和R2所优选代表的或特别优选代表的那些基团。
式(Ⅲ)的羟基乙酰胺是已知的,和/或可按已知的方法直接制备(见美国专利4,509,971和美国专利4,645,525;美国专利4,334,073;DE-OS(德国公布的专利说明书)3,038,598;DE-OS 3,038,636;EP-A-37,526;EP-A-348,737和DE-OS(德国公布的专利说明书)3,819,477]。
按本发明,制备式(Ⅰ)的新的氟苯并噻唑氧基乙酰胺,最好使用稀释剂。优选的稀释剂包括:烃类,如甲苯,二甲苯或环己烷;卤代烃类,如二氯甲烷、氯乙烯、氯仿或氯苯;醚类,如乙醚、二丙醚、二异丙醚、二丁醚、二异丁醚、乙二醇二甲醚、四氢呋喃和二恶烷;醇类,如甲醇、乙醇、丙醇、异丙醇、丁醇、异丁醇、仲丁醇或叔丁醇;酮类,如丙酮、甲基乙基酮、甲基异丙基酮和甲基异丁基酮;酯类,如乙酸甲酯和乙酸乙酯;酰胺类,如二甲基甲酰胺、二甲基乙酰胺,和N-甲基吡咯烷酮;腈类,如乙腈和丙腈;亚砜,如二甲基亚砜;以及水或盐水溶液。
这里所用的盐优选碱金属或碱土金属的盐酸盐或硫酸盐,如氯化钠,氯化钾或氯化钙,特别优选氯化钠。
在本发明的制备方法中,使用酸结合剂是有好处的。优选使用的酸结合剂为强碱性的碱金属和碱土金属化合物,例如氧化物(如氧化钠,氧化钾,氧化镁和氧化钙)、氢氧化物(如氢氧化钠,氢氧化钾,氢氧化镁和氢氧化钙)、醇盐(如叔丁醇钠和叔丁醇钾)和/或碳酸盐(如碳酸钠,碳酸钾碳酸镁和碳酸钙)。
加入0.01%-10%(相对于式(Ⅲ)的羟基乙酰胺的重量)的相转移催化剂在某些情况下可能是有好处的。可提及的这类催化剂包括:
氯化四丁铵、溴化四丁铵、溴化三丁基甲基鏻、氯化三甲基-C13/C15-烷基铵、甲基硫酸二苄二甲铵、氯化二甲基-C12/C14-烷基苄铵、羟基四丁铵、18-冠醚-6、氯化三乙基苄铵、氯化三甲基苄铵、溴化四乙铵。
本发明制备方法中的反应温度的范围相当宽。一般说来,反应可在-50℃至+110℃进行,优选温度为-20℃至+80℃。
本发明制备方法一般在常压下进行,但也可在加压或减压下(如0.1-10巴)进行。
为进行本发明的反应,一般每摩尔式(Ⅱ)的氟苯并噻唑用0.5-5摩尔(优选0.8-1.5摩尔)式(Ⅲ)的羟基乙酰胺。各反应组分可按任意顺序混合到一起。在各种情况下反应混合物均被搅拌直到反应完毕,并按常规方法处理(见制备实施例)。
本发明的活性化合物可被用作脱叶剂、干燥剂、杀阔叶植物剂,特别是可用作杀杂草剂。所谓杂草,从最广泛的意义上来说,所有的植物,只要生长在人们所不希望它生长的地方,都可以称之为杂草。使用本发明的化合物杀灭所有的杂草,还是有选择性地杀灭某些种类的杂草,主要取决于所用的量。
本发明的活性化合物可用于杀灭下列植物:
以下各属的双子叶杂草:
欧白芥属,独行菜属,猪殃殃属,繁缕属,母菊属,春黄菊属,牛膝菊属,藜属,荨麻属,千里光属,苋属,马齿苋属,苍耳属,旋花属,番诸属,蓼属,田菁属,脉草属,蓟属,飞廉属,苦苣菜属,茄属,蔊菜属,水松叶属,母草属,野芝麻属,婆婆纳属,苘庥属,剌酸模属,曼陀罗属,堇菜属,鼬瓣花属,罂粟属,矢车菊属,车轴草属,毛莨属和蒲公英属。
以下各属的双子叶栽培作物:
棉属,大豆属,胡罗卜属,菜豆属,豌豆属,茄属,亚麻属,番诸属,巢菜属,菸草属,番茄属,落花生属,芸苔属,莴苣属,甜瓜属和南瓜属。
以下各属的单子叶杂草:
稗属,狗尾草属,黍属,马唐属,梯牧草属,早熟禾属,羊茅属,碜属,臂形草属,黑麦草属,雀麦属,燕麦属,莎草属,蜀黍属,冰草属,狗牙根属,雨久花属,飘拂草属,慈姑属,荸荠属,莞草属,雀稗属,鸭嘴草属,密穗桔梗属,龙爪茅属,翦股颖属,看麦娘属和豚鼠草属。
以下各属的单子叶栽培作物:
稻属,玉蜀黍属,小麦属,大麦属,燕麦属,黑麦属,蜀黍属,黍属,甘蔗属,凤梨属,天门冬属和葱属。
但本发明的活性化合物决不局限于用于上述各属的植物,它们也可以同样方式用于其它植物。
本发明的化合物,按照使用的浓度不同,适合于清除工业场地、铁路轨道、有树或无树的小路和场院的所有杂草。同样,这些化合物也可用于清除多年生栽培作物(如人工林、装饰林带、果园、葡萄园、柑桔园、坚果林、香蕉林、咖啡园、茶园、橡胶林、油棕榈林、可可林、浆果园和蛇麻草田)中的杂草,以及林间空地、草皮地和牧场中的杂草,和选择性地清除一年生栽培作物中的杂草。
本发明中的式(Ⅰ)化合物特别适合于选择性地清除单子叶杂草,如移栽水稻中的稗草(稗子,掺子)。但是它们一般也可用于清除双子叶栽培作物中的单子叶杂草。
本发明的活性化合物可制成各种常用的制剂,如溶液、乳化液、悬浮液、粉剂、泡沫剂、膏剂、颗粒剂、气雾剂、用活性化合物浸泡的天然的和合成的材料,以及用聚合物制成的微细胶囊。
这些制剂可用已知方法制备,例如将活性化合物与增量剂(液态溶剂,加压液化的气体和/或固态载体)混合,并任意地加入表面活剂(乳化剂和/或分散剂和/或发泡剂)。
若用水作为增量剂时,也可用有机溶剂作为辅助溶剂。适用的液态溶剂主要有:芳烃,如二甲苯、甲苯或烷基萘;氯代芳烃或氯代脂族烃,如氯苯、氯乙烯或二氯甲烷;脂族烃,如环己烷或链烷烃(例如石油裂解物);矿物油和植物油;醇类,如丁醇或乙二醇,以及它们的醚类和酯类;酮类,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水。
适用的固态载体有:例如,铵盐和研磨的天然矿粉,如高岭土、陶土、滑石、白垩、石英、白粘土、蒙脱土或硅藻土;研磨的合成矿粉,如高分散性的二氧化硅、氧化铝和硅酸盐;作为颗粒剂的固体载体,适用的有:粉碎和裂解的天然矿物,如方解石、大理石、浮石、海泡石和白云石,以及合成的无机和有机粉的颗粒,有机物颗粒如锯末、椰壳、玉米芯和菸草杆;适用的乳化剂和/或发泡剂有:非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚(例如烷芳基聚乙二醇醚)、烷基磺酸酯、烷基硫酸酯、芳基磺酸酯以及卵清蛋白的水解产物;适用的分散剂有木素亚硫酸盐废液和甲基纤维素。
粘合剂如羧甲基纤维素和天然的及合成的粉状、颗粒状或胶乳状聚合物(例如阿拉伯树胶,聚乙烯醇和聚乙酸乙烯酯)以及天然的磷脂(如脑磷酯和卵磷脂)、合成的磷脂等均可用于本发明各种制剂中。另外还可用矿物油和植物油作为添加剂。
可以使用着色剂,如无机色素(例如氧化铁、氧化钛和普鲁士兰)和有机染料(例如茜素染料、偶氯染料和金属酞菁染料)、以及微量的营养物(如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐)。
各种制剂一般含有0.1%-95%(W/W)活性化合物,优选的含量为0.5%-90%(W/W)。
为了清除杂草,本发明的活性化合物(或以原料,或以制剂的形式)可与已知的除莠剂混合使用,以形成更好的制剂或罐混合物。
适于与本发明的化合物混合使用的除莠剂均为已知的除莠剂,例如:N-酰苯胺类(如diflufenican)和敌稗,芳香羧酸类(如二氯吡啶甲酸,甲氧二氯苯酸和毒草定),芳氧基链烯酸类(如2,4-滴,2,4-滴丁酸,2,4-滴丙酸,fluroxypyr,2甲4氯,2甲4氯丙酸和乙氯草定),芳氧基苯氧基链烯酯类(如diclofop-methyl,fenoxaprop-ethyl,fulazifop-furyl,haloxyfop-methyl和quizalofop-ethyl),连氮酮类(如Chloridazow和氟哒酮),氨基甲酸酯类(如氯苯胺灵,甜草灵,甲二威灵和苯胺灵),乙酰氯苯胺类(如杂草锁,乙基乙草安,丁草锁,metazachlor,甲氧毒草安,pretilachlor,和毒草安),二硝基苯胺类(如磺胺乐灵,pendimethalin,和氯乐灵),二苯醚类(如acifluorfen,甲酯除草醚,fluoroglycofen,fomesafen,lactofen和乙氧氟甲草醚),脲类(如绿麦隆,敌草隆,伏草隆,异丙隆,利谷隆和噻唑隆),羟胺类(如alloxydim,clethodim,cycloxydim,sethoxydim和tralkoxydim),咪唑啉酮类(如imazethapyr,imazamethabenz,imazapyr和imazaquin),腈类(如溴草腈,敌草腈和碘草腈),氧乙酰胺类(如mefenacet),磺酰脲类(如amidosulfuron,benswifuron-methyl,chlorimuron-ethyl,chlorsulfuron,cinosulfuron,metsulfuron-methyl,nicosulfuron,primisulfuron,pyrazosulfuron-ethyl,thifensulfuron-methyl,triasulfuron和tribenuron-methyl),硫代氨基甲酸酯类(如异丁草丹,环己丹,二氯烯丹,丙草丹,esprocarb,环草丹,prosulfozarb,thiobenzarb和triallate),三嗪类(如阿特拉津,丙腈津,西玛津,西玛净,特丁草净和特丁津),三嗪农类(如六嗪农,甲苯嗪和赛克嗪)以及其它类(如氨三唑,bewfuresate,苯达松,cinmethylin,clomazone,clopyralid,草吡啶,dithiopyr,甜菜呋,fluorochloridone,glufosinate,glyphosate,isoxabew,pyridate,quinchlorac,quinmerac,sulphosate和tridiph ane)。
也可以和其它已知的活性化合物(如杀真菌剂,杀虫剂,杀螨剂,杀线虫剂,驱鸟剂,植物营养剂和改良土壤结构的药剂)混配。
活性化合物可以直接使用,也可以以制剂的形式使用或进一步稀释成即用形式使用,如即用型溶液、混悬液、乳化液、粉剂、膏剂和颗粒剂。这些制剂按惯用的方法使用,如掺水灌溉、喷雾、喷烟雾或撒播等。
本发明的活性化合物可在植物出土前或出土后使用,也可在播种前施到土壤中。
所用的活性化合物的用量可在很大范围内变动,基本上取决于所要求的作用性质。一般的用量为每公顷10g-10kg活性化合物,优选的用量为每公顷50g-5kg。
下述实施例说明本发明的活性化合物的制备和应用。
制备实施例
实施例1
在20℃下,向2.5g(15mmol)N-甲基-羟基乙酰苯胺、3.5g(15mmol)2-甲基磺酰基-4-氟苯并噻唑和50ml丙酮的混合液中,边搅拌边滴加溶于2.7ml水中的0.6g(15mmol)氢氧化钠溶液。将反应混合物在20℃下搅拌12小时,然后倒入大约两倍体积的水中。用抽滤法收集结晶状的产物。
得到3.8g(理论产量的79%)N-甲基-α-(4-氟-苯并噻唑-2-基-氧基)-乙酰苯胺,熔点94℃。
实施例2将2.74g(16.6mmol)N-甲基-羟基乙酰苯胺、0.93g(16.6mmol)氢氧化钾和50ml异丙醇的混合液冷却到-10℃,边搅拌边滴加溶于20ml乙腈中的3.75g(16.6mmol)2-氯-7-氟苯并噻唑溶液。在0℃-5℃下将反应混合物搅拌6小时,然后倒入大约两倍体积的水中,并用二氯甲烷提取三次。将有机相合并,用水洗涤,用硫酸钠干燥,过滤。将滤液浓缩,用柱色谱法将残余物提纯两次(1.硅胶/二氯甲烷,2.硅胶/叔丁基醚)。
得到1.4g(理论值的79%)N-甲基-α-(7-氟-苯并噻唑-2-基-氧基)-乙酰苯胺,熔点116℃。
将300g(2.67mol)3-氟-苯胺、27lg(2.67mol)浓盐酸和259g(2.67mol)硫氰酸钾的混合物加热回流6小时。冷却后通过抽滤将晶状产物分离出来。
得到190g(理论值的41.5%)N-(3-氟-苯基)-硫脲,熔点109℃。
步骤2:
将190g(1.1mol)N-(3-氟苯基)硫脲溶于1100ml氯仿中,冷却到0℃,向此溶液中边搅拌边滴加溶于190ml氯仿中的176g(1.1mol)溴溶液,将此反应混合物加热回流4小时。反应物浓缩后将残余物溶于3立升水中,用浓硫酸将混合物调至pH=1。然后过滤,并用浓氨水使滤液碱化。用抽滤法将晶状产物分离出来。
得到147g(理论值的70%)2-氨基-5-氟-苯并噻唑,熔点167℃。
将147g(0.87mol)2-氨基-5-氟-苯并噻唑、1700ml浓盐酸和20g铜粉的混合物冷却到-10℃,边搅拌边向其中滴加242g(3.5mol)亚硝酸钠的440ml水溶液,将此反应混合物在0℃搅拌60分钟,在50℃再搅拌60分钟。然后用氯仿提取,并用水泵减压蒸馏,将有机相的溶剂小心地除去。
得到80g(理论值的49%)2-氯-5-氟-苯并噻唑,为晶状残余物,熔点69℃。
实施例(Ⅱ-2)步骤1:将12.9g(0.1mol)2,3-二氟苯胺和30ml二甲基甲酰胺的混合物加热回流,同时在1个小时的时间内向其中滴加48g(0.3mol)乙基黄原酸钾的80ml二甲基甲酰胺溶液。不断除去馏出液使瓶中温度保持在145℃。将反应混合物回流搅拌15小时,冷却后倒入1升水中。用20ml浓盐酸的30ml水溶液在10℃使其酸化,通过抽滤将晶状产物分离出来。
得到18.0g(理论值的87%)2-巯基-7-氟-苯并噻唑,熔点193℃。
步骤2:将9.3g(44.5mmol)2-巯基-7-氟-苯并噻唑加到50ml亚硫酰氟中,再加入1ml二甲基甲酰胺后,将混合物慢慢加热回流。回流下搅拌1小时后,将混合物冷却,并用水泵减压,浓缩。将残余物溶于二氯甲烷中,用水洗涤,用硫酸钠干燥并过滤。将滤液浓缩并用柱色谱法(硅胶/二氯甲烷)纯化。
得到4.3g(理论值的45%)黄色油状的2-氯-7-氟-苯并噻唑。
实施例(Ⅱ-3)步骤1:将97g(0.75mol)2,6-二氟苯胺、120g(0.75mol)乙基黄原酸钾和750ml二甲基亚砜的混合物于120℃搅拌3小时。冷却后用300ml水稀释并用浓盐酸调pH=1。将如此获得的晶状产物抽滤分离出来。
得到120g(理论值的80%)2-巯基-4-氟-苯并噻唑熔点180℃。
步骤2:将120g(0.65mol)2-巯基-4-氟-苯并噻唑、26g(0.65mol)氟氧化钠和750ml水的混合物冷却到0℃,边搅拌边向其滴加111g(0.77mol)甲基碘。将反应混合物搅拌3小时,所得之晶状产物通过抽滤分离出来。
得到51g(理论值的39%)2-甲硫基-4-氟-苯并噻唑,熔点30℃。
步骤3:将51g(0.25mol)2-甲硫基-4-氟-苯并噻唑、500ml氟仿、25ml甲酸、2.5ml浓硫酸和2g钼酸铵组成的混合物保持在30℃,边搅拌边向其中滴加145ml的35%浓过氧化氢水溶液(17mol)。将反应混合物在30℃下搅拌2小时,用抽滤法将所获之晶状产物分离出来。
得到31g(理论值的54%)2-甲磺酰基-4-氟-苯并噻唑,熔点160℃。
N-甲基苯并噻唑-2-基-氧基乙酰苯胺(mefenacet)(在EP-A-5,501的实施例1中公开)
实施例A:移栽水稻田的杂草出现前做水面处理
为了制备一种可应用的制剂,将1份活性化合物溶于5份丙酮中,再加1份苄氧基聚乙二醇醚作为乳化剂。然后加水配成所需浓度。将2-3片叶期的稻秧移栽到盛土的盆内,播进待测杂草的种子(1cm深)。两天后向盆内灌入3cm深的水,然后在水面撒上活性化合物制剂。4周后观察结果,以表处理组为对照,用“%”标准评价处理组的除莠作用及对稻秧的损害程度。0%表示无作用,100%表示可完全清除杂草。
在这个试验中可看到,稻秧对本发明的活性化合物,特别是制备实施例(3)、(4)、(5)、(6)和(7)中的化合物,有非常好的耐受性,同时,比起已知的化合物(A),本发明的化合物具有更强的除莠作用,特别是杀稗草。制备实施例(39)中的化合物的作用方式相同。
实施例B
(杂草)出现前处理试验
溶剂:5份(重量比)丙酮
乳化剂:1份(重量比)烷芳基聚乙二醇醚
为了制备适用的活性化合物制剂,将1份(重量比)活性化合物与规定量的溶剂混合,加入规定量的乳化剂,然后用水稀释成所需浓度。
将待试植物种子播种于正常土壤中,24小时后用配好的活性化合物制剂浇灌。最好使每单位面积土壤的浇水量保持恒定。制剂中活性化合物的浓度并不重要,决定性的是每单位面积土壤中所施用的活性化合物的量。三周后,通过与未经处理的对照样植物生长情况的比较来评估活性化合物对所试植物的损害程度(以百分数表示)。0%表示没有作用(像未经处理的对照一样),100%表示完全消灭。
在这个试验中,制备实施例(2)、(4)、(5)、(6)和(7)的化合物表现出很强的除莠作用,而农作物如大豆则对其有很好的耐受性。另外,制备实施例(39)中的化合物的作用方式相同。
Claims (6)
2.权利要求1的式(Ⅰ)化合物,其特征为:在这些化合物中
R1代表C1-C4烷基或烯丙基;
R2代表C1-C6烷基,C1-C2烷氧基-C1-C2烷基,烯丙基,可被氟、氯、溴、氰基、硝基、甲基、乙基、三氟甲基、甲氧基或乙氧基任意取代的苯基,C1-C6烷氧基,或C1-C2烷氧基-C1-C2烷氧基;或者
R1和R2与它们所连接的氮原子一起代表可任意被甲基和/或乙基一至三取代的哌啶基,可任意被甲基和/或乙基一至二取代的吡咯烷基,或全氢化氮杂基。
3.按权利要求1或2的化合物,它们是下式(ⅠC)、(ⅠD)、(ⅠA)和(ⅠB)所示的4-氟、5-氟、6-氟和7-氟苯并噻唑氧基乙酰胺:
5.除莠剂,其特征在于:它们含有至少一种权利要求1的式(Ⅰ)化合物。
6.控制杂草的方法,其特征在于:将权利要求1通式(Ⅰ)的化合物施用于杂草或杂草滋生的环境。
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DE4230903A DE4230903A1 (de) | 1992-09-16 | 1992-09-16 | Fluorbenzthiazolyloxyacetamide |
DEP4230903.4 | 1992-09-16 |
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US8916550B2 (en) * | 2005-05-09 | 2014-12-23 | Hydra Biosciences, Inc. | Compounds for modulating TRPV3 function |
WO2008033564A1 (en) | 2006-09-15 | 2008-03-20 | Hydra Biosciences Inc. | Compounds for modulating trpv3 function |
CN103694197B (zh) * | 2014-01-09 | 2015-07-15 | 华中师范大学 | 苯氧乙酰胺类化合物及其制备方法与应用 |
CN115335050B (zh) | 2020-01-29 | 2024-05-17 | 卡玛瑞制药有限公司 | 用于治疗皮肤病症的化合物和组合物 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0005501A2 (de) * | 1978-05-20 | 1979-11-28 | Bayer Ag | Heteroaryl-oxyessigsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
EP0161602A2 (de) * | 1984-05-16 | 1985-11-21 | Bayer Ag | 6-Chlorbenzazolyloxyacetamide |
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CA1169866A (en) * | 1981-08-03 | 1984-06-26 | Lothar Willms | Process for the manufacture of heterocyclically substituted 4-oxyphenoxy-alkanecarboxylic acid derivatives |
JPH024784A (ja) * | 1988-06-23 | 1990-01-09 | Nippon Tokushu Noyaku Seizo Kk | 5−アミノ−6−フルオロ−2−ベンゾチアゾロンの製法 |
DE4006555A1 (de) * | 1990-02-27 | 1991-08-29 | Schering Ag | Verfahren und zwischenprodukte zur herstellung von substituierten 1-benzthiazolyl-3,4-dimethyl-3-pyrrolin-2,5(1h)-dionen |
DE4113421A1 (de) * | 1991-04-25 | 1992-10-29 | Bayer Ag | 7-chlor-benzthiazolyloxyacetamide |
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1992
- 1992-09-16 DE DE4230903A patent/DE4230903A1/de not_active Withdrawn
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- 1993-09-03 EP EP93114134A patent/EP0588183A1/de not_active Withdrawn
- 1993-09-09 US US08/119,462 patent/US5356864A/en not_active Expired - Fee Related
- 1993-09-10 JP JP24846893A patent/JP3237802B2/ja not_active Expired - Fee Related
- 1993-09-14 KR KR1019930018468A patent/KR100291742B1/ko not_active IP Right Cessation
- 1993-09-16 CN CN93117278A patent/CN1043891C/zh not_active Expired - Fee Related
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Publication number | Priority date | Publication date | Assignee | Title |
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EP0005501A2 (de) * | 1978-05-20 | 1979-11-28 | Bayer Ag | Heteroaryl-oxyessigsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
EP0161602A2 (de) * | 1984-05-16 | 1985-11-21 | Bayer Ag | 6-Chlorbenzazolyloxyacetamide |
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KR100291742B1 (ko) | 2001-09-17 |
CN1087903A (zh) | 1994-06-15 |
US5442074A (en) | 1995-08-15 |
US5356864A (en) | 1994-10-18 |
DE4230903A1 (de) | 1994-03-17 |
EP0588183A1 (de) | 1994-03-23 |
KR940007011A (ko) | 1994-04-26 |
JPH06199822A (ja) | 1994-07-19 |
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