CN1070855C - 4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑化合物及其作除草剂的用途 - Google Patents
4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑化合物及其作除草剂的用途 Download PDFInfo
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- CN1070855C CN1070855C CN96196728A CN96196728A CN1070855C CN 1070855 C CN1070855 C CN 1070855C CN 96196728 A CN96196728 A CN 96196728A CN 96196728 A CN96196728 A CN 96196728A CN 1070855 C CN1070855 C CN 1070855C
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- SZXAJDQTPWYNBN-NWBUNABESA-M sodium;4-methoxycarbonyl-5,5-dimethyl-3-oxo-2-[(e)-n-prop-2-enoxy-c-propylcarbonimidoyl]cyclohexen-1-olate Chemical compound [Na+].C=CCO\N=C(/CCC)C1=C([O-])CC(C)(C)C(C(=O)OC)C1=O SZXAJDQTPWYNBN-NWBUNABESA-M 0.000 description 1
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- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 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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- 239000000341 volatile oil Substances 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
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- 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
- C07D231/14—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 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 to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
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- 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
- C07D231/14—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 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 to ring carbon atoms
- C07D231/38—Nitrogen atoms
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- C07—ORGANIC CHEMISTRY
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- 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
- C07D231/14—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 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 to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
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Abstract
本发明涉及通式(Ⅰ)的4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑化合物，其中R1、R2、R3、R4和R5定义如说明书，其制备方法和作为除草剂的用途。
Description
本发明涉及新的4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑，其制备方法和用作除草剂的用途。
已知取代的吡唑基吡唑是潜在的除草剂(参见EP542388,WO9408999)。但是，这些化合物还未取得任何具体的重要价值。
因此，本发明提供通式(Ⅰ)的新4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑化合物其中
R1代表取代或未取代的烷基；
R2代表取代或未取代的选自烷基、烷氧基和烷硫基的基团，或与R1一起代表-(CH2)m-X-基团；
R3代表氢原子或卤素；
R4代表氢原子或取代或未取代的烷基；
R5代表氢原子、氰基、硝基、硫代氨基甲酰基或卤素，取代或未取代的烷基，取代或未取代的芳基，-O-R6基、-S(O)n-R7基、-NR8R9基或-NR10-CY-R11基；
R6代表氢原子或取代或未取代的烷基、链烯基或炔基；
R7代表取代或未取代的选自烷基，链烯基和炔基的基团；
R8代表氢原子或取代或未取代的选自烷基、链烯基、炔基、环烷基、环烷基烷基、芳基和芳烷基的基团；
R9代表氢原子或取代或未取代的选自烷基、烷氧基、链烯基、炔基、环烷基、环烷基烷基、芳基和芳烷基的基团或代表-S(O)n-R7基，或与R8一起代表链烷二基；
R10代表氢原子或取代或未取代的选自烷基、链烯基和炔基的基团；
R11代表氢原子，取代或未取代的烷基或取代或未取代的芳基；
m代表数字2或3；
n代表数字0,1或2；
X代表CH2、O、S、S(O)n、NH或NCH3；和
Y代表O或S。
通式(Ⅰ)的新的4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑化合物可以通过使通式(Ⅱ)的4-氰基-1-(3-吡唑基)-吡唑
其中
R1、R2、R3、R4和R5各自定义如上，如果适宜，在反应助剂和稀释剂存在下与硫化氢，硫代乙酸或硫代乙酰胺反应而得到。
通式(Ⅰ)的新的4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑化合物具有很强的除草活性。
在上述定义中，饱和或不饱和的烃链如烷基，链烷二基，链烯基或炔基每个甚至可以是连有杂原子的，直链或支链的烃基如烷氧基或烷硫基。
卤素一般代表氟、氯、溴或碘原子，优选氟、氯或溴原子，特别优选氟或氯原子。
本发明优选提供下述的式(Ⅰ)化合物，其中
R1代表未取代的或被氰基-、卤素-或C1-C4-烷氧基-取代的含有1至6个碳原子的烷基；
R2代表未取代的或分别被氰基-、卤素-或C1-C4-烷氧基取代的选自各含有1至6个碳原子的烷基，烷氧基和烷硫基的基团，或与R1一起代表-(CH2)m-X-基团；
R3代表氢原子或卤素；
R4代表氢原子或代表未取代或被氰基-，卤素-或C1-C4-烷氧基取代的含有1至6个碳原子的烷基；
R5代表氢原子、氰基、硝基、硫代氨基甲酰基或卤素，未取代或被氰基-、卤素-或C1-C4-烷氧基-取代的含有1至6个碳原子的烷基；未取代或被氰基-，硝基-，卤素-，C1-C4-烷基-，C1-C4-卤代烷基-，C1-C4烷氧基-或C1-C4卤代烷氧基-取代的苯基；或代表-O-R6基、-S(O)n-R7基，-NR8R9基或-NR10-CY-R11基；
R6代表氢原子，未取代或被氰基-、卤素-、C1-C4-烷氧基-，C1-C4烷基-羰基或C1-C4-烷氧基-羰基-取代的含有1至6个碳原子的烷基；或代表未取代或被氰基-，卤素-或C1-C4烷氧基羰基取代的各含有2至6个碳原子的链烯基或炔基；
R7代表未取代或被氰基-，卤素-，C1-C4-烷氧基-，C1-C4-烷基-羰基或C1-C4-烷氧基羰基-取代的含有1至6个碳原子的烷基；或代表未取代的或分别被氰基-，卤素-或C1-C4-烷基羰基-取代的各含有2至6个碳原子的链烯基或炔基；
R8代表氢原子，未取代或被氰基-，卤素-，C1-C4-烷氧基-，C1-C4-烷基-羰基-或C1-C4烷氧基-羰基取代的含有1至6个碳原子的烷基；或代表未取代的或分别被氰基-，卤素-或C1-C4-烷氧基羰基取代的各含有2至6个碳原子的链烯基或炔基；或未取代或分别被氰基-、卤素-或C1-C4-烷基取代的环烷基或环烷基烷基，其中的环烷基部分含有3至6个碳原子，而烷基部分含有1至4个碳原子；或未取代或分别被氰基-，硫代氨基甲酰基-，硝基-，卤素-，C1-C4-烷基-，C1-C4-卤代烷基-，C1-C4-烷氧基或C1-C4-卤代烷氧基取代的苯基或苯基-C1-C4-烷基；
R9代表氢原子，未取代或被氰基-、卤素-，C1-C4-烷氧基-，C1-C4-烷基-羰基或C1-C4-烷氧基-羰基-取代的含有1至6个碳原子的烷基；或未取代或分别被氰基-，卤素-或C1-C4-烷氧基羰基-取代的各含有2至6个碳原子的链烯基或炔基；或未取代或被氰基-，卤素-或C1-C4-烷氧基取代的含有1至6个碳原子的烷氧基；-S(O)n-R7基；未取代或分别被氰基-，卤素-或C1-C4-烷基取代的环烷基或环烷基烷基，其中各自的环烷基部分含有3至6个碳原子，而烷基部分可以含有1至4个碳原子；未取代或分别被氰基-，硫代氨基甲酰基-，硝基-，卤素-，C1-C4-烷基-，C1-C4-卤代烷基-，C1-C4-烷氧基或C1-C4-卤代烷氧基取代的苯基或苯基-C1-C4-烷基；或与R8一起代表含有2至6个碳原子的链烷二基；
R10代表氢原子，未取代或被氰基-，卤素-，C1-C4烷氧基-，C1-C4-烷基-羰基或C1-C4-烷氧基-羰基取代的含有1至6个碳原子的烷基；或未取代或分别被氰基-，卤素-，或C1-C4-烷氧基羰基取代的，且各含有2至6个碳原子的链烯基或炔基；
R11代表氢原子，未取代或被氰基-，卤素-或C1-C4烷氧基-取代的含有1至6个碳原子的烷基；C1-C4-卤代烷基，C1-C4-烷氧基或C1-C4-卤代烷氧基或未取代或被氰基-，硝基-，卤素-C1-C4-烷基-，C1-C4-卤代烷基-，C1-C4-烷氧基或C1-C4-卤代烷氧基取代的苯基；
m代表数字2或3；
n代表数字0,1或2；
X代表CH2、O、S、S(O)n、NH或NCH3；和
Y代表O或S。
本发明特别提供下述的式(Ⅰ)化合物，其中：
R1代表未取代或分别被氰基-、氟-、氯-、甲氧基或乙氧基取代的甲基、乙基，正-或异丙基，正-，异-，仲-或叔-丁基；
R2代表未取代或分别被氰基-、氟-、氯-、甲氧基或乙氧基取代的甲基、乙基，正-或异-丙基，正-，异-，仲-或叔-丁基，甲氧基，乙氧基，正-异-丙氧基，正-，异-、仲-或叔丁氧基，甲硫基，乙硫基，正-或异丙硫基，正-，异-，仲或叔丁硫基，或与R1一起代表-(CH2)m-X-基团；
R3代表氢原子，氟，氯或溴；
R4代表氢原子或未取代或分别被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正-或异丙基，正-、异-、仲-或叔丁基；
R5代表氢原子，氰基，硝基，硫代氨基甲酰基，氟、氯或溴原子；或未取代或分别被氰基-、氟-、氯-、甲氧基或乙氧基取代的甲基，乙基，正-或异丙基，正-、异-、仲或叔丁基；或未取代或被氰基-、硝基-、氟-、氯-、溴-、甲基-，乙基-，正-或异丙基，正-、异-、仲或叔丁基-，三氟甲基-，甲氧基-，乙氧基-，正-或异丙氧基，二氟甲氧基或三氟甲氧基取代的苯基；或者-O-R6,-S(O)n-R7,-NR8R9或-NR10-CY-R11基团；
R6代表氢原子、未取代或分别被氰基-，氟-，氯-，甲氧基-，乙氧基-，乙酰基-，丙酰基-，甲氧基羰基-或乙氧基羰基取代的甲基，乙基，正-或异丙基，正-、异-、仲-或叔丁基；或未取代或分别被氰基-、氟-、氯-、溴-、甲氧基羰基-或乙氧基羰基取代的丙烯基、丁烯基，丙炔基或丁炔基；
R7代表未取代或分别被氰基-、氟-、氯-、甲氧基-，乙氧基-，乙酰基-，丙酰基，甲氧羰基-或乙氧羰基取代的甲基，乙基，正-或异丙基，正-，异-，仲-或叔丁基，或未取代或分别被氰基-，氟-，氯-，溴-，甲氧羰基-或乙氧羰基取代的丙烯基，丁烯基，丙炔基或丁炔基；
R8代表氢原子，未取代或分别被氰基-、氟-、氯-、甲氧基-，乙氧基-，乙酰基-，丙酰基-，甲氧羰基-或乙氧羰基取代的甲基，乙基，正-或异丙基，正-，异-，仲-或叔丁基，或未取代或分别被氰基-，氟-，氯-，溴-，甲氧羰基或乙氧羰基取代的丙烯基，丁烯基，丙炔基或丁炔基；或未取代或分别被氰基-、氟-、氯-、甲基-或乙基取代的环丙基，环丁基，环戊基，环己基，环丙基甲基，环丁基甲基，环戊基甲基或环己基甲基；或未取代或分别被氰基-，硫代氨基甲酰基-，硝基-，氟-，氯-，溴-，甲基-，乙基-，正-或异丙基，正-、异-、仲-或叔丁基，三氟甲基-，甲氧基-，乙氧基-，正-或异-丙氧基-，二氟甲氧基或三氟甲氧基取代的苯基或苄基；
R9代表氢原子，未取代或分别被氰基-、氟-、氯-、甲氧基-，乙氧基-，乙酰基-，丙酰基-，甲氧羰基-或乙氧羰基取代的甲基，乙基-，正-或异丙基，正-，异-，仲-或叔丁基；或未取代或分别被氰基-，氟-，氯-，溴-，甲氧羰基-或乙氧羰基取代的丙烯基，丁烯基，丙炔基或丁炔基；未取代或被氰基-，氟-，氯-，甲氧基-或乙氧基取代的甲氧基，乙氧基，正-或异丙氧基，正-，异-，仲或叔丁氧基；-S(O)n-R7；未取代或分别被氰基-，氟-，氯-，溴-，甲基-或乙基取代的环丙基，环丁基，环戊基，环己基，环丙基甲基，环丁基甲基，环戊基甲基或环己基甲基；或未取代或分别被氰基-，硫代氨基甲酰基-，硝基-，氟-，氯-，溴-，甲基-，乙基-，正-或异丙基，正-，异-，仲或叔丁基，三氟甲基-，甲氧基-，乙氧基-，正-或异丙氧基，二氟甲氧基或三氟甲氧基取代的苯基或苄基，或与R8一起代表丙烷-1,3-二基(三亚甲基)或丁烷-1,4-二基(四亚甲基)；
R10代表氢原子，未取代或分别被氰基-、氟-、氯-、甲氧基-，乙氧基-，乙酰基-，丙酰基-，甲氧羰基-或乙氧羰基取代的甲基，乙基，正-或异丙基，正-，异-，仲-或叔丁基；或未取代或分别被氰基-，氟，氯-，溴-，甲氧羰基-或乙氧羰基取代的丙烯基，丁烯基，丙炔基或丁炔基；
R11代表氢原子，未取代或分别被氰基-、氟-、氯-、甲氧基-或乙氧基取代的甲基，乙基，正-或异丙基，正-，异-，仲-或叔丁基，或未取代或被氰基-，硝基-，氟-，氯-，溴-，甲基-，乙基-，正-或异丙基-，正-，异-，仲-或叔丁基-，三氟甲基-，甲氧基-，乙氧基-，正-或异丙氧基-，二氟甲氧基-或三氟甲氧基取代的苯基；
m代表数字2或3；
n代表数字0,1或2；
X代表CH2、O、S、S(O)n、NH或NCH3；和
Y代表O或S。
上列的基团定义，无论是一般的还是在优选范围中的，不仅可用于最终产物式(Ⅰ)中，而且还可相应地适用于每种制备方法中出现的起始原料和/或中间体中。如果需要，这些基团定义可以相互结合，包括优选范围的结合。
本发明的式(Ⅰ)化合物的实例列于下述各组：第1组：R5具有例如下列定义：CH3,C2H5,CF3,C2F5,CH(CH3)2,CH2CH2CH3,C(CH3)3,CH2OCH3,CH2CH2OCH3,Cl,Br,F,CN,CSNH2,Ph,NO2,NH2,NHCH3,NHC2H5,NHCH(CH3)2,NHCH2CH2CH3,NHCH2CH=CH2,NHCH2C≡CH,NHCH(CH3)C≡CH,NHCH2CH2OCH3,NHSO2CH3,NHSO2C2H5,NHSO2CH(CH3)2,NHSO2CH2CH2CH3,NHCH2Ph,NHCH2CH2N(CH3)2,N(CH3)2,N(CH3)C2H5,N(CH3)CH(CH3)2,N(CH3)CH(CH3)CH2OCH3,N(CH3)CH2CH2N(CH3)2,N(CH3)SO2CH3,N(CH3)SO2C2H5,N(CH3)CH2CH=CH2,N(CH3)CH2C≡CH,NHCOCH3,NHCOCF3,NHCO-cyclopropyl,NHCO(CH2)2Cl,NHCOPh,N(COCH3)2,N(CH3)COCF3,N(CH2CH=CH2)COCF3,N(CH2C≡CH)COCF3,N(CH3)COCH2Cl,N(CH3)CO-cyclopropyl,OCH3,OC2H5,OCH2CH2CH3,OCH(CH3)2,OCH2CH2OCH3,OCH2CH=CH2,OCH2C≡CH,OCH2COOC2H5,OCH(CH3)COOC2H5,OCH(CH3)C≡CH,SCH3,SOCH3,SO2CH3,SC2H5,SCH(CH3)2,SCH2COOC2H5,SCH(CH3)COOC2H5,SCH2CH=CH2,SCH2C≡CH.第2组：
R5例如具有列于第1组中的定义；第3组：
R5例如具有列于第1组中的定义；第4组：
R5例如具有列于第1组中的定义；第5组：R5例如具有列于第1组中的定义；第5组：R5例如具有列于第1组中的定义；第7组：
R5例如具有列于第1组中的定义；第8组：
R5例如具有列于第1组中的定义；第9组：R5例如具有列于第1组中的定义；第10组：R5例如具有列于第1组中的定义；第11组：
R5例如具有列于第1组中的定义；第12组：
R5例如具有列于第1组中的定义；第13组：
R5例如具有列于第1组中的定义；第14组：R5例如具有列于第1组中的定义；第15组：
R5例如具有列于第1组中的定义；第16组：R5例如具有列于第1组中的定义；第17组：
R5例如具有列于第1组中的定义；第18组：
R5例如具有列于第1组中的定义；第19组：
R5例如具有列于第1组中的定义；第20组：
R5例如具有列于第1组中的定义；第21组：R5例如具有列于第1组中的定义；第22组：R5例如具有列于第1组中的定义；第23组：R5例如具有列于第1组中的定义；第24组：R5例如具有列于第1组中的定义；第25组：
R5例如具有列于第1组中的定义；第26组：R5例如具有列于第1组中的定义；第27组：
R5例如具有列于第1组中的定义。
根据本发明方法，例如用5-氨基-4-氰基-3-氯-1-(1-甲基-5-三氟甲基-3-吡唑基)-吡唑和硫化氢为起始原料，反应过程用下述反应式来说明：
根据本发明方法用作制备式(Ⅰ)化合物的起始原料的4-氰基-1-(3-吡唑基)-吡唑化合物的一般定义如式(Ⅱ)所示。在式(Ⅱ)中，R1、R2、R3、R4和R5各自优选地或具体地具有前面已经指出的定义，并且结合本发明制备的式(Ⅰ)化合物中的优选或特别优选的R1、R2、R3、R4和R5的定义。
式(Ⅱ)的起始原料是已知的和/或可用本领域的已知方法制备(参见EP542388,WO9408999)。
本发明的制备式(Ⅰ)化合物的方法，如果适宜，可在稀释剂的存在下进行。适宜的稀释剂一般是常规的有机溶剂。优选包括脂肪族的，脂环族的和芳香族的，未卤代的或卤代的烃类，例如，戊烷、己烷、庚烷、石油醚、挥发油，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(亚甲基氯化物)，三氯甲烷(氯仿)或四氯化碳；二烷基醚，例如，乙醚、二异丙醚、甲基叔丁醚(MTBE)、乙基叔丁醚、甲基叔戊醚(TAME)、乙基叔戊醚、四氢呋喃(THF)、1,4-二噁烷、1,2-亚乙基二醇二甲醚或1,2-亚乙基二醇二乙醚、二亚乙基二醇二甲醚或二亚乙基二醇二乙醚；二烷基酮，例如丙酮、丁酮(甲乙酮)、甲基异丙酮或甲基异丁酮；腈，例如，乙腈、丙腈、丁腈或苄腈；酰胺，例如，N,N-二甲基-甲酰胺(DMP)、N,N-二甲基-乙酰胺、N-甲基-N-甲酰苯胺、N-甲基-吡咯烷酮或六甲基磷酰胺；酯类，例如，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，例如，二甲亚砜；链烷醇类，例如，甲醇、乙醇、正-或异丙醇、正-、异-、仲-或叔丁醇、1,2-亚乙基二醇单甲醚或1,2-亚乙基二醇单乙醚、二亚乙基二醇单甲醚或二亚乙基二醇单乙醚；它们与水的混合物或纯水。
本发明的制备式(Ⅰ)化合物的方法优选在适宜的反应助剂的存在下进行。适宜的反应助剂一般是常规的无机或有机碱或酸接受体。优选包括碱金属或碱土金属的乙酸盐、胺类，碳酸盐、碳酸氢盐、氢化物、氢氧化物或烷氧化物，例如，乙酸钠，乙酸钾或乙酸钙，氨基锂，氨基钠，氨基钾或氨基钙，碳酸钠，碳酸钾或碳酸钙，碳酸氢钠，碳酸氢钾或碳酸氢钙，氢化锂，氢化钠，氢化钾或氢化钙，氢氧化锂，氢氧化钠，氢氧化钾或氢氧化钙，甲醇钠或甲醇钾，乙醇钠或乙醇钾，正-或异丙醇钠或正-或异丙醇钾，正-、异-、仲-或叔丁醇钠或正-、异-、仲-或叔丁醇钾；而且也包括碱性有机含氮化合物，例如三甲胺，三乙胺，三丙胺，三叔胺，三丁基胺，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-、4-甲基-、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， 4-二甲氨基-吡啶，N-甲基-哌啶，1,4-二氮杂二环[2,2,2]-辛烷(DABCO),1,5-二氮杂二环[4,3,0]-壬-5-烯(DBN)，和1,8-二氮杂二环[5,4,0]-十一-7-烯(DBU)。
在实施本发明的方法中的反应温度可以在相对宽的范围内变化。反应一般在0℃和120℃之间进行，优选在10℃和100℃之间。
本发明的方法一般在大气压下进行。但是，也可在高压或减压-一般在0.1巴至10巴之间进行。
在实施本发明的方法中，式(Ⅱ)的起始原料一般要在反应助剂的存在下预先加入到适宜的稀释剂中，并将硫化氢或硫代乙酸或硫代乙酰胺缓缓计量加入。将反应混合物在各自需要的温度下搅拌直至反应结束。本发明方法的后处理根据具体情况用常规方法进行(参见制备实施例)。
本发明的活性化合物可用作脱叶剂，干燥剂，杀草剂，并且，特别是作除杂草剂。广义地讲，杂草可以理解为是生长在不需要它们的地方的所有植物。本发明的物质是用作全部清除的除草剂还是作选择性除草剂主要根据使用量来决定。
本发明的活性化合物可用于例如下列植物：双子叶杂草属：芥子、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、旋光属、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、水松叶属、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、矢车菊属、三叶草属、毛茛属、蒲公英属。双子叶作物属：棉属、大豆属、甜菜属、胡罗卜属、菜豆属、豌豆属、茄属、亚麻属、甘薯属、野豌豆属、烟草属、番茄属，花生属、芸苔属、莴苣属、黄瓜属、南瓜属。单子叶杂草属：稗属、狗尾草属、黍属、马唐属、梯牧草属、早熟禾属、羊矛属、蟀蟋草属、臂形草属、毒麦属、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、
菇属、荸荠属、莞草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪牙属、翦股颖属、看麦娘属和Apera。单子叶栽培作物属：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、葱属。
但是，本发明的活性化合物并不以任何方式限定用于在这些种属植物中，而且可以相同方式延伸至用于其它植物。
该化合物根据其浓度，可用于控制全部杂草，例如适用于工业用地和铁路，以及有或没有种植树木的道路和广场。同样，这些化合物可用于常年生栽培作物中的杂草控制，例如森林，观赏树木的种植园、果园、葡萄园、柑橘林、坚果园、香蕉栽培园、咖啡种植园、茶叶种植园、橡胶种植园，油棕榈种植园、可可种植园、浆果园和蛇麻草地，草坪、草地和牧草地，并用于一年生作物的杂草的选择性控制。
本发明的式(Ⅰ)化合物特别是适用于在单子叶植物和双子叶植物栽培中的苗前或苗后的单子叶和双子叶杂草的选择性控制。
式(Ⅰ)化合物在某种程度上还具有杀昆虫活性。
可将活性化合物制成常规制剂，如溶液，乳液，可湿性粉末，悬浮液，粉末，粉尘剂，膏剂，可溶性粉末，颗粒剂，悬乳浓缩物(suspo-emulsion concertrates)，浸渍活性化合物的天然和合成制剂，和聚合物精细的胶囊。
这些制剂可用已知方法制备，如将活性化合物与增量剂，即液体溶剂和/或固体载体混合，可选择地使用表面活性剂，即乳化剂和/或分散剂和/或发泡剂来制备制剂。
当用水作补充剂时。例如有机溶剂可用作辅助溶剂。作为液体溶剂，主要适用的有：芳香烃，如二甲苯、甲苯或烷基萘，氯代的芳香烃和氯代脂肪烃，例如氯苯，氯乙烯或二氯甲烷；脂肪烃如环己烷；或链烷烃例如汽油馏份；矿物油或植物油；醇类例如丁醇或乙二醇及其醚和酯；酮类例如丙酮，甲乙酮，甲基异丁基酮或环己酮；强极性溶剂，例如二甲基甲酰胺和二甲亚砜和水。
适宜的固体载体是：例如铵盐和磨碎的天然矿物质，如高岭土、陶土、滑石粉、白垩、石英、硅镁土、蒙脱石或硅藻土和磨碎的合成矿物质，如粉碎的硅土，氧化铝和硅酸盐，可用于颗粒的适宜固体载体是：例如粉碎和分级的天然岩石如方解石，大理石，浮石；海泡石和白云石，以及无机和有机岩粉的合成颗粒，和有机材料的颗粒如锯木屑，可可壳，玉米芯和烟草杆；适宜的乳化和/或发泡剂是：例如非离子和阴离子乳化剂，如脂肪酸聚氧乙烯酯，脂肪醇聚氧乙烯醚，例如聚乙二醇烷基芳基醚，烷基磺酸盐，烷基硫酸盐，芳基磺酸盐和蛋白水解液；适宜的分散剂是：例如木素-亚硫酸盐废液和甲基纤维素。
粘合剂如羧甲基纤维素和粉末、颗粒或胶乳形式的天然和合成聚合物，如阿拉伯胶，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，和合成磷脂等可用于制剂中。而且粘合剂可以是矿物油和植物油。
可以使用着色剂如无机颜料，如氧化铁，氧化钛和普鲁士兰，和有机染料，如茜素染料，偶氮染料和金属酞菁染料，还可使用痕量营养素如铁、镁、硼、铜、钴、钼和锌的盐类。
制剂中通常含有0.1至95重量百分比的活性化合物，优选0.5至90％。
为了控制杂草，本发明的活性化合物本身或其制剂可与已知的除草剂成品制剂或罐装混合物混合使用。
混合物中的可能成分是已知除草剂，例如N-酰苯胺，如吡氟草胺和敌稗；芳基羧酸，如吡啶甲酸，麦草畏和毒莠定；芳氧基链烷酸，如2,4-D、2,4-DB、2,4-DP、氟草烟、MCPA、MCPP和绿草定；芳氧基-苯氧基-链烷酸酯，如禾草灵、高噁草禾草灵，吡氟禾草灵，吡氟氯禾灵和喹禾灵；连氮类(azinones)，如chloridazon和哒草伏；氨基甲酸酯类，如氯苯胺灵，甜菜安，甜菜宁和苯胺灵；氯代N-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，pendimethalin和氟乐灵；二苯基醚类如三氟羧草醚，甲羧除草醚，乙羧氟草醚，氟黄胺草醚，halosa-fen，乳氟乐草灵和乙氧氟草醚；脲类，如绿麦隆，敌草隆，伏草隆，异丙隆，利谷隆和甲基苯噻隆；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，如酰胺黄隆，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，环草特，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，如阿特拉津，氰草津，西玛津，西草净，特丁净和特丁津；三嗪酮类，如hexazinone，苯嗪草酮和嗪草酮；和其它类，如杀草强，呋草黄，灭草松，环庚草醚，异恶草酮，clopyralid，双苯唑炔，氟硫草定，呋草黄，氟咯草酮，草胺膦，草甘膦，isoxaben、pyridate，二氯喹啉酸，喹草酸，sulphosate和tridiphane。
也可以与其它已知活性化合物混合，这些活性化合物是例如抗真菌剂，杀虫剂，杀螨剂，杀线虫剂，驱鸟剂，植物营养剂和土壤改良剂。
活性化合物本身，或能以其制剂或需要进一步稀释的形式使用，如备用溶液，悬浮液，乳液，粉末，膏剂和颗粒剂。可以常规方式使用，例如洒水，喷雾，粉化或分散。
本发明的活性化合物可用于植物的芽前或芽后，也可以在播种前掺入土壤中。
活性化合物的用量可以在一个大致范围内变化。主要取决于所需达到的效果。通常，活性化合物的用量是每公顷土壤表面1g至10kg，优选每公顷5g至5kg。
本发明活性化合物的制备和使用见下述实施例。制备实施例
实施例1
将2.9g(10mmol)的5-氨基-4-氰基-1-(4-氯-5-二氟甲氧基-1-甲基-3-吡唑基)-吡唑加入到20ml吡啶和10ml三乙胺中并加热至70℃，同时将硫化氢通入混合物中。在70℃使硫化氢继续通过2小时，然后用氮气吹洗混合物，冷却并用水泵真空浓缩。将残余物用水搅动并用浓盐酸酸化，过滤分离结晶产物。
得到2.7g(理论值的84％)，熔点为156℃的5-氨基-1-(4-氯-5-二氟甲氧基-1-甲基-3-吡唑基)-4-硫代氨基甲酰基-吡唑。
实施例2
将2.5g(7mmol)5-溴-4-氰基-1-(4-氯-5-二氟甲氧基-1-甲基-3-吡唑基)-吡唑和2.2g(29mmol)硫代乙酸于回流温度搅拌45分钟，将混合物用旋转蒸发仪水泵真空浓缩。将混合物用乙醚搅动并过滤分离结晶产物。
得到2.1g(理论值的78％)熔点为175℃的5-溴-1-(4-氯-5-二氟甲氧基-1-甲基-3-吡唑基)-4-硫代氨基甲酰基-吡唑。
用实施例1和2的方法，进一步制备式(Ⅰ)化合物-参见表1：表1：式(Ⅰ)化合物实施例实施例号 R1 R2 R3 R4 R5 熔点(℃)3 CH3 OCHF2 Cl H CH3 1334 CH3 OCHF2 Cl H H 1405 CH3 OCHF2 Cl CH3 NH2 170应用实施例：
实施例A芽前试验溶剂：5重量份丙酮乳化剂：1重量份烷基芳基乙二醇醚
为制备适宜的活性化合物制剂，将1重量份活性化合物与所示量的溶剂混合，加入所示量的乳化剂并将浓缩物用水稀释以达到所需浓度。
将受试植物的种子种入普通土壤中。约24小时后，用活性化合物制剂浇灌土壤。尤其使每单位面积的喷洒量保持恒定。制剂中活性化合物的浓度并不重要，只有每单位面积上活性化合物的使用率才是决定性的。
三周后，对植物的损坏度与未处理的对照组的生长情况相比得到百分损坏率。数据是指：
0％=没作用(如未处理的对照组)
100％=全部损坏
在该试验中，实施例1制备的化合物在使用率为125g/公顷时，对下列杂草显示有很强的活性：马唐属(80％)，稗属(95％)，荀麻属(100％)，苋属(100％)和黎属(100％)，同时作如大麦属和棉有好的耐受性(0-10％)。
实施例B芽后试验溶剂：5重量份丙酮乳化剂：1重量份烷基芳基聚乙二醇醚
为制备适宜的活性化合物制剂，将1重量份活性化合物与上述量的溶剂混合，加入上述量的乳化剂后，将浓缩物用水稀释以达到所需浓度。
在受试植物长到5-15cm高时，用每单位面积所需活性化合物的具体用量喷洒活性化合物制剂。选择喷洒液的浓度以便使所需活性化合物的具体用量在1000升水/公顷。
三周后，对植物的损坏度与未处理的对照组的生成情况相比得到百分损坏率。数据是指：
0％=没有作用(如未处理的对照组)
100％=全部损坏
在该试验中，实施例1制备的化合物在使用率为250g/公顷时对下列杂草显示很强的活性：稗属(100％)，繁缕属(95％)，苘麻属(100％)，苋属(100％)和黎属(100％)，同时作物如小麦有很好的耐受性(10％)。
Claims (6)
1．通式(Ⅰ)的4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑化合物
其中
R1代表未取代或被氰基-、卤素-或C1-C4-烷氧基-取代的含有1至6个碳原子的烷基；
R2代表未取代或分别被氰基-、卤素-或C1-C4-烷氧基取代的各自含有1至6个碳原子的烷基，烷氧基和烷硫基，或与R1一起代表-(CH2)m-X-基团；
R3代表氢原子或卤素；
R4代表氢原子或代表未取代或被氰基-，卤素-或C1-C4-烷氧基取代的含有1至6个碳原子的烷基；
R5代表氢原子、氰基、硝基、硫代氨基甲酰基或卤素；未取代或被氰基-，卤素-或C1-C4-烷氧基取代的含有1至6个碳原子的烷基；未取代或被氰基-，硝基-，卤素-，C1-C4-烷基-，C1-C4-卤代烷基-，C1-C4-烷氧基-或C1-C4-卤代烷氧基-取代的苯基，或代表-O-R6,-S(O)n-R7,-NR8R9或-NR10-CY-R11基团；
R6代表氢原子，未取代或被氰基-、卤素-、C1-C4-烷氧基-，C1-C4-烷基-羰基-或C1-C4-烷氧基-羰基-取代的含有1至6个碳原子的烷基；或代表未取代的或分别被氰基-，卤素-或C1-C4-烷氧基羰基取代的各含有2至6个碳原子的链烯基或炔基；
R7代表未取代或被氰基-，卤素，C1-C4-烷氧基-，C1-C4-烷基-羰基-或C1-C4-烷氧基-羰基-取代的含有1至6个碳原子的烷基；或代表未取代的或分别被氰基-，卤素-或C1-C4-烷氧基羰基取代的各含有2至6个碳原子的链烯基或炔基；
R8代表氢原子，未取代或被氰基-，卤素-，C1-C4-烷氧基-，C1-C4-烷基-羰基-或C1-C4-烷氧基-羰基-取代的含有1至6个碳原子的烷基；未取代或分别被氰基-，卤素-或C1-C4-烷氧基羰基取代的各含有2至6个碳原子的链烯基或炔基；未取代或分别被氰基-、卤素-或C1-C4-烷基取代的环烷基或环烷基烷基，其中各自的环烷基部分含有3至6个碳原子，而烷基部分可以含有1至4个碳原子；或未取代或分别被氰基-，硫代氨基甲酰基-，硝基-，卤素-，C1-C4-烷基-，C1-C4-卤代烷基-，C1-C4-烷氧基或C1-C4-卤代烷氧基取代的苯基或苯基-C1-C4-烷基；
R9代表氢原子，未取代或被氰基-、卤素-，C1-C4-烷氧基-，C1-C4-烷基-羰基-或C1-C4-烷氧基-羰基-取代的含有1至6个碳原子的烷基；未取代或分别被氰基-，卤素-或C1-C4-烷氧基羰基取代的各含有2至6个碳原子的链烯基或炔基；未取代或被氰基-，卤素-或C1-C4-烷氧基取代的含有1至6个碳原子的烷氧基；-S(O)n-R7基团；未取代或分别被氰基-，卤素-或C1-C4-烷基取代的环烷基或环烷基烷基，其中各自的环烷基部分含有3至6个碳原子，而烷基部分可以含有1至4个碳原子；未取代或分别被氰基-，硫代氨基甲酰基-，硝基-，卤素-，C1-C4-烷基-，C1-C4-卤代烷基-，C1-C4-烷氧基或C1-C4-卤代烷氧基取代的苯基或苯基-C1-C4-烷基；或与R8一起代表含有2至6个碳原子的链烷二基；
R10代表氢原子，未取代或被氰基-，卤素-，C1-C4-烷氧基-，C1-C4-烷基-羰基-或C1-C4-烷氧基-羰基-取代的含有1至6个碳原子的烷基；或未取代或分别被氰基-，卤素-或C1-C4-烷氧基羰基取代的各含有2至6个碳原子的链烯基或炔基；
R11代表氢原子，未取代或被氰基-，卤素-或C1-C4-烷氧基取代的含有1至6个碳原子的烷基；C1-C4-烷氧基或C1-C4-卤代烷氧基或未取代或被氰基-，硝基-，卤素-，C1-C4-烷基-，C1-C4-卤代烷基-，C1-C4-烷氧基-或C1-C4-卤代烷氧基取代的苯基；
m代表数字2或3；
n代表数字0,1或2；
X代表CH2、O、S、S(O)n、NH或NCH3；和
Y代表O或S。
2．制备通式(Ⅰ)的4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑的方法，
其中
R1、R2、R3、R4和R5各自定义如权利要求1，其特征是使通式(Ⅱ)的4-氰基-1-(3-吡唑基)-吡唑
其中
R1、R2、R3、R4和R5各自定义如上，与硫化氢，硫代乙酸或硫代乙酰胺反应，如果适宜，反应在反应助剂和稀释剂存在下进行。
3．根据权利要求1的通式(Ⅰ)的4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑，其特征是：
R1代表未取代或分别被氰基-、氟-、氯-、甲氧基-或乙氧基取代的甲基、乙基，正-或异丙基，正-，异-，仲-或叔-丁基；
R2代表未取代或分别被氰基-、氟-、氯-、甲氧基-或乙氧基取代的甲基、乙基，正-或异丙基，正-，异-，仲-或叔丁基，甲氧基，乙氧基，正-或异-丙氧基，正-，异-，仲-或叔丁氧基，甲硫基，乙硫基，正-或异丙硫基，正-，异-，仲或叔丁硫基，或与R1一起代表-(CH2)m-X-基团；
R3代表氢原子，氟，氯或溴；
R4代表氢原子或未取代或分别被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正-或异丙基，正-、异-、仲-或叔丁基；
R5代表氢原子，氰基，硝基，硫代氨基甲酰基，氟、氯或溴原子，未取代或分别被氰基-、氟-、氯-、甲氧基或乙氧基取代的甲基，乙基，正-或异丙基，正-、异-、仲或叔丁基，未取代或被氰基-、硝基-、氟-、氯-、溴-、甲基-，乙基-，正-或异-丙基，正-、异-、仲或叔丁基-，三氟甲基-，甲氧基-，乙氧基-，正-或异丙氧基，二氟甲氧基或三氟甲氧基取代的苯基，-O-R6,-S(O)n-R7,-NR8R9或-NR10-CY-R11基团；
R6代表氢原子、未取代或分别被氰基-，氟-，氯-，甲氧基-，乙氧基-，乙酰基-，丙酰基-，甲氧基羰基-或乙氧基羰基取代的甲基，乙基，正-或异丙基，正-、异-、仲-或叔丁基，或未取代或分别被氰基-、氟-、氯-、溴-、甲氧基羰基-或乙氧基羰基取代的丙烯基、丁烯基，丙炔基或丁炔基；
R7代表未取代或分别被氰基-、氟-、氯-、甲氧基-，乙氧基-，乙酰基-，丙酰基，甲氧羰基-或乙氧羰基取代的甲基，乙基，正-或异丙基，正-，异-，仲-或叔丁基，或未取代或分别被氰基-，氟-，氯-，溴-，甲氧羰基-或乙氧羰基取代的丙烯基，丁烯基，丙炔基或丁炔基；
R8代表氢原子，未取代或分别被氰基-、氟-、氯-、甲氧基-，乙氧基-，乙酰基-，丙酰基-，甲氧羰基-或乙氧羰基取代的甲基，乙基，正-或异丙基，正-，异-，仲-或叔丁基，未取代或分别被氰基-，氟-，氯-，溴-，甲氧羰基-或乙氧羰基取代的丙烯基，丁烯基，丙炔基或丁炔基；未取代或分别被氰基-、氟-、氯-、甲基-或乙基取代的环丙基，环丁基，环戊基，环己基，环丙基甲基，环丁基甲基，环戊基甲基或环己基甲基，或未取代或分别被氰基-，硫代氨基甲酰基-，硝基-，氟-，氯-，溴-，甲基-，乙基-，正-或异丙基，正-、异-、仲-或叔丁基，三氟甲基-，甲氧基-，乙氧基-，正-或异丙基-，二氟甲氧基或三氟甲氧基取代的苯基或苄基；
R9代表氢原子，未取代或分别被氰基-、氟-、氯-、甲氧基-，乙氧基-，乙酰基-，丙酰基-，甲氧羰基-或乙氧羰基取代的甲基，乙基-，正-或异丙基，正-，异-，仲-或叔丁基；未取代或分别被氰基-，氟-，氯-，溴-，甲氧羰基-或乙氧羰基取代的丙烯基，丁烯基，丙炔基或丁炔基；未取代或分别被氰基-，氟-，氯-，甲氧基或乙氧基取代的甲氧基，乙氧基，正-或异丙氧基，正-，异-，仲或叔丁氧基；-S(O)n-R7基团；未取代或分别被氰基-，氟-，氯-，溴-，甲基-或乙基取代的环丙基，环丁基，环戊基，环己基，环丙基甲基，环丁基甲基，环戊基甲基或环己基甲基；未取代或分别被氰基-，硫代氨基甲酰基-，硝基-，氟-，氯-，溴-，甲基-，乙基-，正-或异丙基，正-，异-，仲-或叔丁基，三氟甲基-，甲氧基-，乙氧基-，正-异丙氧基，二氟甲氧基或三氟甲氧基取代的苯基或苄基，或与R8一起代表丙烷-1,3-二基(三亚甲基)或丁烷-1,4-二基(四亚甲基)；
R10代表氢原子，未取代或分别被氰基-、氟-、氯-、甲氧基-，乙氧基-，乙酰基-，丙酰基-，甲氧羰基-或乙氧羰基取代的甲基，乙基，正-或异丙基，正-，异-，仲-或叔丁基，或未取代或分别被氰基-，氟-，氯-，溴-，甲氧羰基-或乙氧羰基取代的丙烯基，丁烯基，丙炔基或丁炔基；
R11代表氢原子，未取代或分别被氰基-、氟-、氯-、甲氧基-或乙氧基取代的甲基，乙基，正-或异丙基，正-，异-，仲-或叔丁基，或未取代或被氰基-，硝基-，氟-，氯-，溴-，甲基-，乙基-，正-或异丙基-，正-，异-，仲-或叔丁基-，三氟甲基-，甲氧基-，乙氧基-，正-或异丙氧基-，二氟甲氧基-或三氟甲氧基取代的苯基；
m代表数字2或3；
n代表数字0,1或2；
X代表CH2、O、S、S(O)n、NH或NCH3；和
Y代表O或S。
4．除草组合物，其特征是含有至少一种根据权利要求1至3的通式(Ⅰ)的4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑化合物。
5．控制不需要植物的方法，其特征是将权利要求1至3的通式(Ⅰ)的4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑化合物作用于不需要的植物和/或其生长的土壤。
6．权利要求1至3的通式(Ⅰ)的4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑化合物用于控制不需要植物的用途。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19532347A DE19532347A1 (de) | 1995-09-04 | 1995-09-04 | 4-Thiocarbamoyl-1-(3-pyrazolyl)-pyrazole |
| DE19532347.5 | 1995-09-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1195339A CN1195339A (zh) | 1998-10-07 |
| CN1070855C true CN1070855C (zh) | 2001-09-12 |
Family
ID=7771058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96196728A Expired - Fee Related CN1070855C (zh) | 1995-09-04 | 1996-08-22 | 4-硫代氨基甲酰基-1-(3-吡唑基)-吡唑化合物及其作除草剂的用途 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6025498A (zh) |
| EP (1) | EP0851860A1 (zh) |
| JP (1) | JPH11514346A (zh) |
| KR (1) | KR19990044254A (zh) |
| CN (1) | CN1070855C (zh) |
| AU (1) | AU702537B2 (zh) |
| BR (1) | BR9610193A (zh) |
| CA (1) | CA2230788A1 (zh) |
| DE (1) | DE19532347A1 (zh) |
| HK (1) | HK1016163A1 (zh) |
| WO (1) | WO1997009313A1 (zh) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19623892A1 (de) * | 1996-06-06 | 1997-12-11 | Hoechst Schering Agrevo Gmbh | Substituierte Pyrazolyl-pyrazolderivate |
| DE19630555A1 (de) * | 1996-07-18 | 1998-01-22 | Hoechst Schering Agrevo Gmbh | Substituierte Pyrazolyl-pyrazolderivate |
| DE19631865A1 (de) * | 1996-08-08 | 1998-02-12 | Bayer Ag | Substituierte 1-(3-Pyrazolyl) -pyrazole |
| DE19751943A1 (de) | 1997-11-24 | 1999-05-27 | Hoechst Schering Agrevo Gmbh | 1-Methyl-5-alkylsulfonyl-, 1-Methyl-5-alkylsulfinyl- und 1-Methyl-5-alkylthio-substituierte Pyrazolylpyrazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide |
| TWI429654B (zh) | 2006-10-04 | 2014-03-11 | Genentech Inc | 用於ｖｅｇｆ之ｅｌｉｓａ |
| CN110551122B (zh) * | 2018-06-04 | 2022-02-18 | 海利尔药业集团股份有限公司 | 一种取代的吡唑基吡唑磺酰胺类化合物或其作为农药可接受的盐、组合物及其用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL116507A (en) * | 1991-11-13 | 1997-08-14 | Schering Ag | Pyrazole derivatives |
| DK0663913T3 (da) * | 1992-10-12 | 1999-05-03 | Hoechst Schering Agrevo Gmbh | Nye substituerede pyrazolderivater, fremgangsmåder til deres fremstilling samt deres anvendelse som herbicider |
-
1995
- 1995-09-04 DE DE19532347A patent/DE19532347A1/de not_active Withdrawn
-
1996
- 1996-08-22 CN CN96196728A patent/CN1070855C/zh not_active Expired - Fee Related
- 1996-08-22 JP JP9510812A patent/JPH11514346A/ja active Pending
- 1996-08-22 US US09/029,419 patent/US6025498A/en not_active Expired - Fee Related
- 1996-08-22 KR KR1019980701490A patent/KR19990044254A/ko not_active Application Discontinuation
- 1996-08-22 CA CA002230788A patent/CA2230788A1/en not_active Abandoned
- 1996-08-22 EP EP96929302A patent/EP0851860A1/de not_active Withdrawn
- 1996-08-22 BR BR9610193A patent/BR9610193A/pt unknown
- 1996-08-22 WO PCT/EP1996/003692 patent/WO1997009313A1/de not_active Application Discontinuation
- 1996-08-22 AU AU68761/96A patent/AU702537B2/en not_active Ceased
-
1999
- 1999-03-15 HK HK99101066A patent/HK1016163A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU702537B2 (en) | 1999-02-25 |
| EP0851860A1 (de) | 1998-07-08 |
| AU6876196A (en) | 1997-03-27 |
| JPH11514346A (ja) | 1999-12-07 |
| HK1016163A1 (en) | 1999-10-29 |
| DE19532347A1 (de) | 1997-03-06 |
| US6025498A (en) | 2000-02-15 |
| KR19990044254A (ko) | 1999-06-25 |
| WO1997009313A1 (de) | 1997-03-13 |
| BR9610193A (pt) | 1998-12-15 |
| CA2230788A1 (en) | 1997-03-13 |
| CN1195339A (zh) | 1998-10-07 |
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