CN1070486C - 氟代噻二唑基氧基乙酰胺 - Google Patents
氟代噻二唑基氧基乙酰胺 Download PDFInfo
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- CN1070486C CN1070486C CN96193719A CN96193719A CN1070486C CN 1070486 C CN1070486 C CN 1070486C CN 96193719 A CN96193719 A CN 96193719A CN 96193719 A CN96193719 A CN 96193719A CN 1070486 C CN1070486 C CN 1070486C
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- chlorine
- fluorine
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- 238000000034 method Methods 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 42
- -1 methylidene, ethyl Chemical group 0.000 claims description 32
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 25
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 241000196324 Embryophyta Species 0.000 claims description 22
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 22
- 239000011737 fluorine Substances 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 244000025254 Cannabis sativa Species 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 claims description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 125000005981 pentynyl group Chemical group 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000005920 sec-butoxy group Chemical group 0.000 claims description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical group C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 1
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- 230000002508 compound effect Effects 0.000 claims 1
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- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
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- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 4
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- 125000003118 aryl group Chemical group 0.000 abstract description 3
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- 125000003302 alkenyloxy group Chemical group 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000005605 benzo group Chemical group 0.000 abstract description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 125000005842 heteroatom Chemical group 0.000 abstract description 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
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- 239000000126 substance Substances 0.000 description 12
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- 239000000975 dye Substances 0.000 description 6
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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- 241000209219 Hordeum Species 0.000 description 4
- 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
- 241000207763 Solanum Species 0.000 description 4
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- 239000000463 material Substances 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
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- 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
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- 239000008096 xylene Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及新颖的式(Ⅰ)氟代噻二唑基氧基乙酰胺：
其中
R1代表氢或代表各任选取代的烷基、链烯基、炔基或芳烷基，
R2代表各任选取代的烷基、烷氧基、链烯基、链烯氧基、炔基、环烷基、环烯基、芳基、芳烷基或芳烷氧基，或
R1和R2同与之相连的氮原子一起形成一任选取代的饱和或不饱和氮杂环，该氮杂环可以含有其它的杂原子且它可以苯并稠合，且
R3代表氟代噻二唑基，
涉及其制备方法和新颖的中间体及其作为除草剂的应用。
Description
本发明涉及新颖的氟代噻二唑基氧基乙酰胺、其制备方法和新颖的中间体及其作为除草剂的应用。
已知某些氯代噻二唑基氧基乙酰胺如化合物N-甲基-N-苯基-2-(3-氯-1,2,4-噻二唑-5-基-氧基)-乙酰胺具有除草性能(参见例如EP-A300344)。然而，这些现有技术化合物的活性并非在所有的应用领域均完全令人满意，特别是在低施用剂量和浓度下。
因此，本发明提供新颖的通式(Ⅰ)氟代噻二唑基氧基乙酰胺
其中
R1代表氢或代表各任选取代的烷基、链烯基、炔基或芳烷基，
R2代表各任选取代的烷基、烷氧基、链烯基、链烯氧基、炔基、
环烷基、环烯基、芳基、芳烷基或芳烷氧基，或
R1和R2同与之相连的氮原子一起形成一任选取代的饱和或不饱和
氮杂环，该氮杂环可以含有其它的杂原子且它可以苯并稠
合，且
R3代表氟代噻二唑基。
此外，业已发现，新颖的通式(Ⅰ)氟代噻二唑基氧基乙酰胺可以如下获得：使通式(Ⅱ)的烷基磺酰基化合物与通式(Ⅲ)的羟基乙酰胺反应，
其中
R3如上所定义，且
R代表烷基，
其中
R1和R2各如上所定义，
如果适宜在稀释剂存在下，如果适宜在酸结合剂存在下，且如果适宜在催化剂存在下进行反应。
最后，已发现，新颖的通式(Ⅰ)氟代噻二唑基氧基乙酰胺具有令人感兴趣的除草性能。
出人意外的是，与由现有技术已知的N-甲基-N-苯基-2-(3-氯-1,2,4-噻二唑-5-基-氧基)-乙酰胺化合物相比，本发明的通式(Ⅰ)氟代噻二唑基氧基乙酰胺在一定程度上兼有良好的作物相容性和明显更强的除草活性。
本发明优选提供式(Ⅰ)化合物，其中
R1代表氢、C1-C8-烷基(它任选由氟、氯、氰基或C1-C4-烷氧基
取代)，或C2-C8-链烯基(它任选由氟和/或氯取代)，或C2-C8-
炔基或苄基(它任选由氟、氯、C1-C4-烷基和/或C1-C4-烷氧基
取代)，
R2代表C1-C8-烷基(它任选由氟、氯、氰基或C1-C4-烷氧基取
代)，C2-C8-链烯基(它任选由氟和/或氯取代)，或C2-C8-炔
基，或C3-C6-环烷基(它任选由氯和/或C1-C3-烷基取代)，或
C5-或C6-环烯基，或苄基(它任选由氟、氯、C1-C4-烷基和/
或C1-C4-烷氧基取代)，或苯基(它任选由氟、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)，或C1-C8-烷氧基(它任选由C1-C4-烷氧基取
代)，或C3-C4-链烯氧基或苄氧基，或
R1和R2同与之相连的氮原子一起形成饱和或不饱和五至七元氮杂
环，该氮杂环任选由C1-C3-烷基单至三取代且它可以任选苯
并稠合，且
R3代表3-氟-1,2,4-噻二唑-5-基或2-氟-1,3,4-噻二唑-5-基。
本发明特别提供式(Ⅰ)化合物，其中
R1代表甲基、乙基、正或异丙基、正、异或仲丁基、正、异或仲
戊基(它们各任选由氟、氯、氰基、甲氧基或乙氧基取代)，或
丙烯基、丁烯基、丙炔基或丁炔基，
R2代表甲基、乙基、正或异丙基、正、异或仲丁基、正、异或仲
戊基、正、异或仲己基(它们各任选由氟、氯、氰基、甲氧基
或乙氧基取代)，或丙烯基、丁烯基、戊烯基、丙炔基、丁炔
基或戊炔基，或环戊基或环己基(它们各任选由甲基和/或乙基
取代)，或环己烯基、或苄基(它任选由氟、氯和/或甲基取代)
或苯基(它任选由氟、氯、溴、氰基、硝基、甲基、乙基、
三氟甲基、甲氧基或乙氧基取代)，或甲氧基、乙氧基、正或
异丙氧基、正、异或仲丁氧基、正、异或仲戊氧基(它们各任
选由甲氧基或乙氧基取代)，或
R1和R2同与之相连的氮原子一起代表任选由甲基和/或乙基单至
三取代的哌啶基，或任选由甲基和/或乙基单或二取代的吡咯
烷基，或全氢氮杂基或1,2,3,4-四氢(异)喹啉基，且
R3代表3-氟-1,2,4-噻二唑-5-基。
上面所列的基团定义，不论是在一般情况下或是在优选范围中，不仅适合于式(Ⅰ)的终产物，而且也相应地适合于所有制备中所需的起始物质和/或中间体。这些基团的定义也可以按需要相互组合，因此，包括所指的优选范围间的组合。
在式(Ⅰ)中的下列基团之可能含意的实例列于下列表1中
表1：下列基团的含意
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
表1(续)
使用(例如)2-氟-5-甲磺酰基-1,3,4-噻二唑和N-乙基-羟基乙酰苯胺作为起始物质，本发明方法的反应途径可以用下列反应式说明：
式(Ⅱ)给出的是，将在本发明制备通式(Ⅰ)化合物的方法中用作起始物质的烷基磺酰基化合物的一般定义。在式(Ⅱ)中，R3优选或特别是具有这样的含意，即在关于式(Ⅰ)化合物的描述中在上面已经指明的R3的优选或特别优选含意。
式(Ⅱ)起始物质尚未公开于文献中；作为新物质，它们也构成本发明申请主题的一部分。
新颖的通式(Ⅱ)烷基磺酰基化合物可以如下获得，使相应的通式(Ⅳ)烷硫基化合物
其中
R和R3各如上所定义，
与氧化剂如过氧化氢反应，如果适宜在催化剂如钨酸钠存在下，如果适宜在稀释剂如乙酸和/或水存在下，在0℃至100℃间的温度下进行反应(参见制备实施例)。
作为中间体需要的式(Ⅳ)烷硫基化合物尚未公开于文献中；作为新物质，它们也构成本发明申请主题的一部分。
新的式(Ⅳ)化合物可以如下获得：在吡啶存在下，在-30℃至+50℃间的温度下，使相应的氨基-烷硫基-噻二唑与亚硝酸钠和氟化氢反应，或在催化剂如18-冠-6存在下，在稀释剂如环丁砜存在下，在100℃至180℃间的温度下，使相应的氯代-烷硫基-噻二唑与氟化钾反应(参见制备实施例)。
式(Ⅲ)给出的是，将在本发明制备通式(Ⅰ)化合物的方法中用作起始物质的羟基乙酰胺的一般定义。在式(Ⅲ)中，R1和R2优选或特别是具有这样的含意，即在关于式(Ⅰ)化合物的描述中在上面已经指明的R1和R2的优选或特别优选含意。
式(Ⅲ)羟基乙酰胺是已知的和/或可以通过已知的方法制备(参见US 4509971、US 4645525、US 4334073、DE 3038598、DE3038636、EP 37526、EP 348737、DE 3819477)。
进行本发明方法的适合的稀释剂是所有常规的惰性有机溶剂。这些溶剂特别包括任选卤代的脂族、脂环族或芳族烃，诸如戊烷、己烷、庚烷、石油醚、轻石油、汽油、苯、甲苯、二甲苯、氯苯、二氯苯、环己烷、甲基环己烷、二氯甲烷、氯仿和四氯化碳；醚类，如，***、二异丙醚、叔丁基甲基醚、叔戊基甲基醚、二噁烷、四氢呋喃、乙二醇二甲醚或乙二醇二***、二乙二醇二甲醚或二乙二醇二***；酮类，如，丙酮、丁酮或甲基异丁基酮；腈类，如，乙腈、丙腈、丁腈或苯甲腈；酰胺类，如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮或六甲基磷酰三胺；酯类，如，乙酸甲酯、乙酸乙酯、乙酸正或异丙酯、乙酸正、异或仲丁酯；亚砜类，如二甲亚砜；醇类，如，甲醇、乙醇、正或并丙醇、正、并、仲或叔丁醇、乙二醇单甲醚或乙二醇单***、二乙二醇单甲醚、二乙二醇单***；其与水的混合物或单独的水。
本发明方法优选在适合的酸受体存在进行的。适合的酸受体是所有的常规无机或有机碱。这些碱包括例如：碱金属或碱土金属氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐，如氢化锂、氢化钠、氢化钾或氢化钙、氨化锂、氨化钠或氨化钾、甲醇钠或甲醇钾、乙醇钠或乙醇钾、丙醇钠或丙醇钾、异丙醇铝、叔丁醇钠或叔丁醇钾、氢氧化钠或氢氧化钾、氢氧化铵、乙酸钠、乙酸钾或乙酸钙、乙酸铵、碳酸钠、碳酸钾或碳酸钙、碳酸铵、碳酸氢钠或碳酸氢钾，以及碱性有机氮化合物，如三甲胺、三乙胺、三丙胺、三丁胺、乙基二异丙胺、N,N-二甲基环己胺、二环己胺、乙基二环己胺、N,N-二甲基苯胺、N,N-二甲基苄胺、吡啶、2-甲基-、3-甲基-和4-甲基吡啶、2,4-二甲基-、2,6-二甲基-、3,4-二甲基-和3,5-二甲基吡啶、5-乙基-2-甲基-吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂双环壬烯(DBN)和二氮杂双环十一碳烯(DBU)。
实施本发明方法时，反应温度可以在相对宽的范围内变化。一般而言，反应是在-50℃和+100℃之间，优选在-20℃至+60℃间的温度下进行的。
本发明方法通常是在常压下进行的。然而，也可以在增高或降低的压力下，通常是在0.1巴至10巴之间进行。
实施本发明方法时，在每一种情形下所需的起始物质通常是以大致等摩尔量使用的。然而，在每一情形下，也可能相对大地过量使用二种组分之一。通常是在适合的稀释剂中，在酸受体存在下进行反应，且反应混合物在所需的特定温度下搅拌几小时。每种情形下的反应产物的收集和分离是通过惯用的方法来完成的(参见制备实施例)。
本发明活性化合物可以用作脱叶剂、干燥剂、杀茎杆剂(haulmkiller)，特别是用作除草剂。所谓的杂草，就其最广的含意而言，应理解为生长在不该生长的地方的所有植物。本发明的物质是作为灭生性除草剂或是作为选择性除草剂基本上取决于所用的量。
本发明化合物可以与下列植物相关使用：
下列属的双子叶杂草：欧白芥属、独行草属、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、马齿苋赂、苍耳属、旋花属、甘薯属、蓼属、田菁属、豚草属、蓟属、飞廉属、苦苣菜属、茄属、蔊菜属、节节草属、母草属、野芝麻属、婆婆纳属、苘麻属、刺酸模属、曼陀罗属、堇菜属、鼬瓣花属、罂粟属、矢车菊属、三叶草属、毛莨属和蒲公英属。
下列属的双子叶作物：棉属、大豆属、甜菜属、胡萝卜属、菜豆属、豌豆属、茄属、亚麻属、甘薯属、野豌豆属、烟草属、蕃茄属、花生属、芸苔属、莴苣属、黄瓜属和南瓜属。
下列属的单子叶杂草：稗属、狗尾草属、黍属、马唐属、梯牧草属、早熟禾属、羊茅属、蟋蟀草属、臂形草属、黑麦草属、雀麦属、燕麦属、莎草属、高粱属、冰草属、狗牙根属、雨久花属、飘拂草属、慈菇属、荸荠属、藨草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪茅属、剪股颖属、看麦娘属和风草属。
下列属的单子叶作物：稻属、玉米属、小麦属、大麦属、燕麦属、黑麦属、高粱属、黍属、甘蔗属、凤梨属、天门冬属和葱属。
然而，本发明化合物的应用决不仅限于这些属，它们也可以以相同的方式延伸至其它植物。
取决于化合物的浓度，本发明化合物适合于例如工业场地和铁道线上以及有或无种植树林的道路和广场上的灭生性除草。同样，这类化合物也可以用于防治多年生作物中的杂草，例如人造林、装饰树林、果园、葡萄园、柑桔林、坚果园、香蕉种植园、咖啡种植园、茶园、橡胶种植园、油棕榈种植园、可可种植园、浆果林和啤酒花田、草场、草皮和牧场中的杂草，以及选择性地防治一年生作物中的杂草。
本发明式(Ⅰ)化合物特别适合于选择性地防治单子叶和双子叶作物中的单子叶和双子叶杂草，特别是以苗前的方式。
活性化合物可以转化成常规剂型，如液剂、乳剂、可湿性粉剂、悬浮剂、粉剂、喷粉剂、膏剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然和合成物质和在用聚合物制成的微胶囊。
这些型剂可以用已知的方式生产，例如，将活性化合物与填充剂，即液体溶剂和/或固体载体混合，并任选使用表面活性剂，即乳化剂和/或分散剂和/或起泡剂。
在用水作填充剂的情况下，也可以用有机溶剂作助溶剂。作为液体溶剂，适合的主要有：芳族化合物，如二甲苯，甲苯或烷基萘，氯代芳烃或氯代脂肪烃，如氯代苯类、氯乙烯类或二氯甲烷，脂族烃，如环己烷或石蜡，例如石油馏份、矿物和植物油，醇类，如丁醇或乙二醇以及其醚和酯，酮类，如丙酮、甲乙酮、甲基异丁基酮或环己酮，强极性溶剂，如二甲基甲酰胺或二甲基亚砜，以及水。
适合的固体载体是：
例如铵盐和磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土，和磨碎的合成矿物质，如高分散二氧化硅、氧化铝和硅酸盐；用于颗粒剂的适合的固体载体有：例如压碎并分级的天然矿物质如方解石、大理石、浮石、海泡石和白云石，以及有机和无机粉的合成颗粒，和如下有机物的颗粒：锯木屑、椰壳、玉米芯和烟茎；适合的乳化剂和/或起泡剂是：例如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，烷基磺酸盐，烷基硫酸盐，芳基磺酸盐以及白蛋白水解产物；适合的分散剂是：例如，木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如粉状、颗粒或乳胶形式的羧甲基纤维素和天然和合成聚合物，如***胶、聚乙烯醇和聚乙酸乙烯酯，以及天然磷脂，如脑磷脂和卵磷脂，和合成磷脂。其它的粘合剂可以是矿物油和植物油。
也可能使用染料，如无机颜料，例如氧化铁、氧化钛和普鲁士蓝，和有机染料，如茜素染料、偶氮染料和金属酞菁染料，以及微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95％的活性化合物，优选0.5至90％。
防治杂草时，本发明活性化合物本身或以其制剂形式也可以与已知除草剂、直接可用的制剂或可能的桶混物一起以混合物的形式使用。
用于混合物的可能组分是已知的除草剂，例如N-酰苯胺类如吡氟草胺和敌稗；芳基羧酸类如二氯吡啶甲酸、麦草畏和毒草定；芳氧基链烷酸类如2,4-滴、2,4-滴丁酸、2,4-滴丙酸、氟草烟、2甲4氯、2甲4氯丙酸和定草酯；芳氧基苯氧基链烷酸类如禾草灵、噁唑禾草灵、吡氟禾草灵、吡氟氯禾灵和喹禾灵；连氮酮类如杀草敏和达草灭；氨基甲酸酯类如氯苯胺灵、甜菜安、甜菜宁和苯胺灵；氯乙酰苯胺类如甲草胺、乙草胺、丁草胺、吡草胺、异丙甲草胺、丙草胺和毒草胺；二硝基苯胺类如安磺灵、二甲戊乐灵和氟乐灵；二苯醚类如三氟羧草醚、甲羧除草醚、乙羧氟草醚、氟黄胺草醚、halosafen、乳氟禾草灵和乙氧氟草醚；脲类如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和噻唑隆；羟胺类如禾草灭、烯草酮、噻草酮、稀禾定和肟草酮；咪唑啉酮类如咪草烟、咪草酯、灭草烟和灭草喹；腈类如溴苯腈、敌草腈和碘苯腈；氧乙酰胺类如苯噻草胺；磺酰脲类如amidosufuron、苄嘧黄隆、氯嘧黄隆、绿黄隆、醚黄隆、甲黄隆、烟嘧黄隆、氟嘧黄隆、吡嘧黄隆、噻黄隆、醚苯黄隆和苯黄隆；硫代氨基甲酸酯类如丁草特、灭草特、燕麦敌、茵达灭、禾草畏、草达灭、苄草丹、杀草丹和野麦畏；三嗪类如莠去津、氰草津、西玛津、西草净、去草净和特丁净；三嗪酮类如环嗪酮、苯嗪草酮和嗪草酮；其它除草剂如杀草强、呋草黄、灭草松、环庚草醚、异噁草酮、二氯吡啶酸、双苯唑快、氟硫草定、乙呋草黄、氟咯草酮、草铵膦、草甘膦、isoxaben、达草止、二氯喹啉酸、喹草酸、草硫膦和灭草环。
也可以是与其它已知活性化合物的混合物，如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养素和土壤结构改良剂。
活性化合物可以以其本身、以其制剂或由之经进一步稀释而制备的使用形式使用，所述的使用形式有例如可直接使用溶液、悬浮液、乳液、粉、膏和颗粒。它们以常规方法使用，例如浇泼、喷雾、弥雾或撒施等等。
本发明活性化合物可以在植物出苗前或后施用。它们也可以在播种前掺入土壤中。
所用的活性化合物的量可以在相当宽的范围内变化。用量基本上取决于所需的效果。通常，使用量在每公顷土表面积用1克至10千克之间，优选每公顷5克至5千克。
本发明活性成分的制备和使用可以参见下列实施例。
制备实施例：
实施例1
先将3.6g(19mmol)3-氟-5-甲磺酰基-1,2,4-噻二唑和3.1g(19mnol)N-甲基-N-苯基-羟基乙酰胺导入30ml丙酮中，并且将此混合物冷却至-20℃。之后滴加入0.76g氢氧化钠在3ml水中的溶液。反应混合物在-15℃下搅拌12小时，之后用水稀释至二倍体积，通过抽吸过滤，分离出晶体产物。
得2.6g(理论值的52％)N-甲基-N-苯基-2-(3-氟-1,2,4-噻二唑-5-基-氧基)乙酰胺，熔点：82℃。
用实施例1的方法和根据本发明制备方法的一般描述，也可以制备(例如)列于下表2中的式(Ⅰ)化合物，在每一情况下，R3代表3-氟-1,2,4-噻二唑-5-基。
表2：式(1)化合物的实例实施例号 R1 R2 物理数据2 -(CH2)6- nD 20=1.51023 CH2-CH=CH2 CH2-CH=CH2 nD 20=1.50584 CH(CH3)2 OCH2CH2OC2H5 nD 20=1.47485 CH(CH3)2
Mp.:50℃6
nD 20=1.52017 CH3
nD 20=1.49498 n-C3H7 n-C3H7 nD 20=1.49459 -(CH2)5-10 CH2-CH=CH2 CH2-CH=CH211 CH(CH3)2 OCH(CH3)2 nD 20=1.480812 CH3
nD 20=1.5423
表2(续)实施例号 R1 R2 物理数据13 C2H5 C2H5 nD 20=1.498314 C2H5
15
nD 20=1.529216
nD 20=1.517317 CH3 n-C4H9 nD 20=1.496018 CH3
19 C3H5 C6H520 n-C4H9 n-C4H9 nD 20=1.494121 CH3
Mp.:48℃22 CH3
nD 20=1.4867
表2(续)实施例号R1 R2 物理数据23
OCH324 CH3
25 CH3
26 CH2CH2OC2H5 CH2CH2OC2H527
28 CH3 CH2C6H529 CH3
nD 20=1.527830 CH3
31 CH(CH3)2
表2(续)实施例号 R1 R2 物理数据32 CH3
33
nD 20=1.519134 C2H5
Mp.:40℃35
nD 20=1.587036
nD 20=1.510537
nD 20=1.513638 CH(CH3)2
Mp.:40℃39 CH(CH3)2
nD 20=1.521240 CH(CH3)2
Mp.:85℃
式(Ⅱ)起始物质：
实施例(Ⅱ-1)
将22.3g(0.15mol)3-氟-5-甲硫基-1,2,4-噻二唑、0.3g钨酸钠和120ml乙酸加热至70℃，并在此温度下滴加入48ml(0.44molH2O2)的过氧化氢水溶液。之后，混合物用400ml水稀释，用氯仿萃取。分离出有机相，用浓度为5％的亚硫酸氢钠水溶液洗涤，经硫酸钠干燥，过滤。之后在水泵真空下仔细蒸馏去除滤液中的溶剂。
获得20g(理论值的77％)3-氟-5-甲磺酰基-1,2,4-噻二唑，为淡黄色油状物，折光率n20 D=1.5430。
实施例(Ⅱ-2)
将15g(0.10mol)2-氟-5-甲硫基-1,3,4-噻二唑溶于50ml乙酸中，并在10℃至15℃的内部温度下，滴加入26.5g(0.17mol)过锰酸钾在400ml水中的溶液。反应混合物随后在约10℃下搅拌约60分钟，之后滴加入亚硫酸氢钠饱和水溶液直至褪色。抽吸过滤，分离出晶体产物。
获得15.9g(理论值的59％)2-氟-5-甲磺酰基-1,3,4-噻二唑，熔点：65℃。
式(Ⅳ)起始物质：
实施例(Ⅳ-1)
先将1240ml(61.2mol)氟化氢在0℃至10℃充入，冷却下与660ml(8.14mol)吡啶混合。在10℃下，加入100g(0.68mol)3-氨基-5-甲硫基-1,2,4-噻二唑，随后冷却至-15℃。在-15℃至-5℃下，用约3小时，一点点地加入49.2g(0.72mol)亚硝酸钠。之后将混合物的温度由约-10℃缓慢升至约+40℃，于其中释放出氮气。在氮气停止形成时，将混合物倒入2.5升水中，之后用环己烷各250ml萃取四次。合并的萃取液用碳酸氢钠水溶液洗涤，用硫酸钠干燥，并过滤。滤液在水泵真空下浓缩，残留物经维格罗分馏柱(10cm)在高真空下分级蒸馏。
获得34g(理论值的33％)3-氟-5-甲硫基-1,2,4-噻二唑，沸点：62℃/0.3毫巴。
1H NMR(CDCl3,δ):2.73ppm。
实施例(Ⅳ-2)
将63g的2-氯-5-甲硫基-1,3,4-噻二唑(纯度94％,0.356mol)与45 g氟化钾和1g的18-冠-6一起溶于136g环丁砜中，并将混合物加热至145℃4小时，快速真空蒸馏反应混合物，产生40g粗产物(纯度约85％)，通过分级真空蒸馏分离，由上述粗产物中得到30g(理论值的55％)2-氟-5-甲硫基-1,3,4-噻二唑，沸点：73-75℃/1毫巴。
应用实施例：
在应用实施例中，用下列化合物作为对照物质
N-甲基-N-苯基-2-(3-氯-1,2,4-噻二唑-5-基-氧基)-乙酰胺(由EP-A300344已知)。
实施例A
苗前试验
溶剂： 5份重量丙酮
乳化剂： 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时，将1份重量的活性化合物与所述量的溶剂混合，将所述量的乳化剂加入，并用水将此乳油稀释至所需浓度。
将试验植物的种子播入通常的土壤中。24小时后，土壤用活性化合物制剂浇灌。最好使每单位面积的水量保持恒定。制剂中活性化合物的浓度是不重要的，只有每单位施用的活性化合物的量是关键的。三周后，将植物的损害程度与未处理对照样的发育相比较，定出损害％。
数值的含意如下：
0％=无作用(与未处理相同)
100％=完全损害
在此试验中，例如，制备实施例1、2、3和4的化合物对杂草的活性比已知化合物A的要显著高出许多，而且它们中的一些能够被例如大麦和大豆很好地耐受。
表A：苗前试验/温室活性化合物 施用量 大麦 大豆 冰草属 燕麦 雀麦 苋属 母菊属 茄属(g/ha) 属 属
(A) (已知) 500 40 40 60 60 40 70 70 20
(I) 500 20 20 95 95 95 100 100 95
表A(续) 施用量 雀麦活性化合物 (g/ha) 大麦 大豆 冰草属 燕麦属 属 苋属 母菊属 茄属
(2) 500 50 0 95 90 70 100 95 95(3) 500 - 0 100 100 95 100 90 80
500 - 60 100 100 100 100 90 70
Claims (6)
1．通式(Ⅰ)的氟代噻二唑基氧基乙酰胺，
其中R1代表氢，
C1-C8-烷基，任选由氟、氯、氰基或C1-C4-烷氧基
取代，
C2-C8-链烯基，任选由氟和/或氯取代，或
C2-C8-炔基或苄基，任选由氟、氯、C1-C4-烷基和/
或C1-C4-烷氧基取代，R2代表C1-C8-烷基，任选由氟、氯、氰基或C1-C4-烷氧基
取代，
C2-C8-链烯基，任选由氟和/或氯取代，
C2-C8-炔基或C3-C6-环烷基，任选由氯和/或C1-C3-
烷基取代，
C5-或C6-环烯基或苄基，任选由氟、氯、C1-C4-烷基
和/或C1-C4-烷氧基取代，或
苯基，任选由氟、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，或
C1-C8-烷氧基，任选由C1-C4-烷氧基取代，或
C3-C4-链烯氧基或苄氧基，或R1和R2同与之相连的氮原子一起形成饱和或不饱和5至7
元氮杂环，该氮杂环任选由C1-C3-烷基单至三取代且
它可以任选苯并稠合，和R3代表3-氟-1,2,4-噻二唑-5-基或2-氟-1,3,4-噻二唑-5-基。
2．根据权利要求1的式(Ⅰ)化合物，其特征在于，
R1代表甲基、乙基、正或异丙基、正、异或仲丁基、正、
异或仲戊基，它们各任选由氟、氯、氰基、甲氧基或
乙氧基取代，或
丙烯基、丁烯基、丙炔基或丁炔基，
R2代表甲基、乙基、正或异丙基、正、异或仲丁基、正、
异或仲戊基、正、异或仲己基，它们各任选由氟、氯、
氰基、甲氧基或乙氧基取代，
丙烯基、丁烯基、戊烯基、丙炔基、丁炔基或戊炔基，
或环戊基或环己基，它们各任选由甲基和/或乙基取
代，
环己烯基或苄基，任选由氟、氯和/或甲基取代，
苯基，任选由氟、氯、溴、氰基、硝基、甲基、乙基、
三氟甲基、甲氧基或乙氧基取代，或
甲氧基、乙氧基、正或异丙氧基、正、异或仲丁氧基、
正、异或仲戊氧基，它们各任选由甲氧基或乙氧基取
代，或
R1和R2同与之相连的氮原子一起代表任选由甲基和/或乙
基单至三取代的哌啶基，或任选由甲基和/或乙基单
或二取代的吡咯烷基，或全氢氮杂基或1,2,3,4-
四氢喹啉基或1,2,3,4-四氢异喹啉基，和
R3代表3-氟-1,2,4-噻二唑-5-基。
3．制备权利要求的式(Ⅰ)化合物的方法，其特征在于，
使通式(Ⅱ)的烷基磺酰基化合物与通式(Ⅲ)的羟基乙酰胺反应，
其中
R3如权利要求1中所定义，且
R代表烷基，
其中
R1和R2各如权利要求1中所定义，
如果适宜在稀释剂存在下，如果适宜在酸结合剂存在下，且如果适宜在催化剂存在下进行反应。
4．除草组合物，其特征在于，含有至少一种权利要求1的式(Ⅰ)化合物。
5．权利要求1的通式(Ⅰ)化合物防治莠草的应用。
6．防治杂草的方法，其特征在于，使权利要求1的通式(Ⅰ)化合物作用于杂草或其栖生地。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19509044A DE19509044A1 (de) | 1995-03-14 | 1995-03-14 | Fluorthiadiazolyloxyacetamide |
| DE19509044.6 | 1995-03-14 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN00126214A Division CN1288888A (zh) | 1995-03-14 | 2000-08-21 | 用于制备氟代噻二唑基氧基乙酰胺的中间体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1183777A CN1183777A (zh) | 1998-06-03 |
| CN1070486C true CN1070486C (zh) | 2001-09-05 |
Family
ID=7756552
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96193719A Expired - Fee Related CN1070486C (zh) | 1995-03-14 | 1996-03-01 | 氟代噻二唑基氧基乙酰胺 |
| CN00126214A Pending CN1288888A (zh) | 1995-03-14 | 2000-08-21 | 用于制备氟代噻二唑基氧基乙酰胺的中间体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN00126214A Pending CN1288888A (zh) | 1995-03-14 | 2000-08-21 | 用于制备氟代噻二唑基氧基乙酰胺的中间体 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5858922A (zh) |
| EP (1) | EP0815093B1 (zh) |
| JP (1) | JPH11501913A (zh) |
| KR (1) | KR19980702955A (zh) |
| CN (2) | CN1070486C (zh) |
| AU (1) | AU4943696A (zh) |
| DE (2) | DE19509044A1 (zh) |
| WO (1) | WO1996028434A1 (zh) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0192117A2 (de) * | 1985-02-16 | 1986-08-27 | Bayer Ag | 5-Chlor-1,3,4-thiadiazol-2-yloxy-acetamide |
| EP0300344A1 (de) * | 1987-07-23 | 1989-01-25 | Bayer Ag | Halogenierte Thiadiazolyl-oxyessig-säureamide, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Herbizide |
-
1995
- 1995-03-14 DE DE19509044A patent/DE19509044A1/de not_active Withdrawn
-
1996
- 1996-03-01 CN CN96193719A patent/CN1070486C/zh not_active Expired - Fee Related
- 1996-03-01 DE DE59605759T patent/DE59605759D1/de not_active Expired - Fee Related
- 1996-03-01 EP EP96905830A patent/EP0815093B1/de not_active Expired - Lifetime
- 1996-03-01 JP JP8527215A patent/JPH11501913A/ja not_active Ceased
- 1996-03-01 US US08/913,075 patent/US5858922A/en not_active Expired - Fee Related
- 1996-03-01 AU AU49436/96A patent/AU4943696A/en not_active Abandoned
- 1996-03-01 WO PCT/EP1996/000836 patent/WO1996028434A1/de not_active Application Discontinuation
- 1996-03-01 KR KR1019970706363A patent/KR19980702955A/ko not_active Application Discontinuation
-
2000
- 2000-08-21 CN CN00126214A patent/CN1288888A/zh active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0192117A2 (de) * | 1985-02-16 | 1986-08-27 | Bayer Ag | 5-Chlor-1,3,4-thiadiazol-2-yloxy-acetamide |
| EP0300344A1 (de) * | 1987-07-23 | 1989-01-25 | Bayer Ag | Halogenierte Thiadiazolyl-oxyessig-säureamide, Verfahren und Zwischenprodukte zu ihrer Herstellung und ihre Verwendung als Herbizide |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1183777A (zh) | 1998-06-03 |
| WO1996028434A1 (de) | 1996-09-19 |
| KR19980702955A (ko) | 1998-09-05 |
| AU4943696A (en) | 1996-10-02 |
| EP0815093A1 (de) | 1998-01-07 |
| EP0815093B1 (de) | 2000-08-16 |
| DE19509044A1 (de) | 1996-09-19 |
| CN1288888A (zh) | 2001-03-28 |
| US5858922A (en) | 1999-01-12 |
| JPH11501913A (ja) | 1999-02-16 |
| DE59605759D1 (de) | 2000-09-21 |
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