CN1225638A - 取代的三唑并吖嗪磺酰胺 - Google Patents
取代的三唑并吖嗪磺酰胺 Download PDFInfo
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- CN1225638A CN1225638A CN97196536A CN97196536A CN1225638A CN 1225638 A CN1225638 A CN 1225638A CN 97196536 A CN97196536 A CN 97196536A CN 97196536 A CN97196536 A CN 97196536A CN 1225638 A CN1225638 A CN 1225638A
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- 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
本发明涉及式(Ⅰ)新的取代的三唑并吖嗪磺酰胺化合物其中:Q1代表氮或CH基团;Q2代表氮或CH基团;R1代表氢或卤素,或者代表C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基氨基或二-(C1-C4-烷基)氨基,在各种情况下其各自任选被羟基,卤素或C1-C4-烷氧基取代;R2代表氢或卤素,或者代表C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基氨基或二-(C1-C4-烷基)氨基,在各种情况下其各自任选被卤素取代;以及Ar代表4-氰基-2,5-二氧苯基,2,6-二甲氧基—苯基,2-溴-3-三氟甲基—苯基,2-溴-5-三氟甲基—苯基,6-氯—吡啶-3-基—甲基或说明书中的所述5-元或6-元(杂)环基团之一。本发明还涉及这些化合物的盐,这些新的化合物的制备方法,以及其作为植物处理剂的用途。
Description
本发明涉及新的取代的三唑并吖嗪磺酰胺,其制备方法,以及涉及其作为植物处理剂的用途。
(专利)文献中已知很多种三唑并吖嗪磺酰胺(参见EP142152,EP244847,EP375076,US4605433,US5163995,WO89/10368,Pestic.Sci.29(1990),341-355)。
其中
Q1代表氮或CH基团,
Q2代表氮或CH基团,
R1代表氢,卤素或者代表C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基氨基或二-(C1-C4-烷基)氨基,它们各自任选被羟基,卤素或C1-C4-烷氧基取代,
R2代表氢,卤素或者代表C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基氨基或二-(C1-C4-烷基)氨基,它们各自任选被卤素取代,以及
Ar代表4-氰基-2,5-二氟苯基,2,6-二甲氧基-苯基,2-溴-3-三氟甲基-苯基,2-溴-5-三氟甲基-苯基,4-溴-2,6-二甲基-苯基,6-氯-吡啶-3-基-甲基或下面的5-元或6-元(杂)环基团中的一个: 其中m在各种情况下代表数1或2,n在各种情况下代表数0,1或2,A1代表任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基或者代表任选被氰基,卤素或C1-C4-烷基取代的C3-C6-环烷基,
A2代表各自任选被卤素取代的C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基,
A3代表任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基,
A4代表任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基,
A5代表任选被氰基,卤素或C1-C4-烷氧基取代的C2-C4-烷基,代表任选被卤素取代的C2-C4-链烯基或者代表任选被氰基,卤素或C1-C4-烷基取代的C3-C6-环烷基-C1-C4-烷基,
A6代表卤素或者代表各自任选被卤素取代的C1-C4-烷基,C1-C4-烷氧基,C2-C4-链烯基或C2-C4-链烯基氧基,
A7代表任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基,
A8代表氰基,硝基或者任选被卤素取代的C1-C4-烷基,
A9代表氰基,卤素或者任选被卤素取代的C1-C4-烷基,
A10代表任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基或者代表任选被氰基,卤素或C1-C4-烷基取代的C3-C6-环烷基,
A11代表氢或者代表各自任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基,C1-C4-烷基-羰基,C1-C4-烷氧羰基或C1-C4-烷基磺酰基,
A12代表氢,氰基,卤素或任选被卤素取代的C1-C4-烷基,
A13代表氰基,氨基甲酰基,5,6-二氢-1,4,2-二噁嗪-3-基,卤素,C1-C4-烷基,C1-C4-烷基-羰基或C1-C4-烷氧羰基,
A14代表氢,代表氰基,氨基甲酰基,卤素,C1-C4-烷基,C1-C4-烷基-羰基或C1-C4-烷氧羰基,
A15代表氢,代表氰基,氨基甲酰基,卤素,C1-C4-烷基,C1-C4-烷基-羰基或C1-C4-烷氧羰基,或者与A14一起代表稠合的苯并基团,
A16代表氢,氰基,卤素或者代表各自任选被卤素取代的C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基,
A17代表氢,氰基,卤素或任选被卤素取代的C1-C4-烷基,
A18代表氢,氰基,卤素或任选被卤素取代的C1-C4-烷基,
A19代表氢或C1-C4-烷基,
A20代表C1-C4-烷基或C2-C4-链烯基,
A21代表氰基,卤素,C1-C4-烷基或C1-C4-卤代烷基,
A22代表C1-C4-烷基或C1-C4-卤代烷基,
A23代表C1-C4-烷基,
A24其自身代表C1-C4-烷基或者与A23一起代表C2-C4-链烷二基,
A25代表氰基,卤素,C1-C4-烷基或C1-C4-卤代烷基,
A26代表C1-C4-烷基,
A27代表氰基,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,
A28代表氢,二氟甲基,C1-C4-烷基-羰基,C1-C4-烷氧羰基或C1-C4-烷基磺酰基,
A29代表氰基,卤素,C1-C4-烷基或C1-C4-卤代烷基,
A30代表氢,C1-C4-烷基或C1-C4-烷氧基,
A31代表氢或C1-C4-烷基,
A32代表氰基,卤素,C1-C4-烷基或C1-C4-卤代烷基,
A33代表氢,C1-C4-烷基或C1-C4-烷氧基,
A34代表氢或C1-C4-烷基,
A35代表氰基,卤素,C1-C4-烷基或C1-C4-卤代烷基,
A36代表氢,C1-C4-烷基,C3-C6-环烷基或苯基,
A37代表氢,C1-C4-烷基,C3-C6-环烷基或苯基,
A38代表氢,卤素,代表各自任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基,C1-C4-烷氧基或C1-C4-烷硫基,或者代表各自任选被氰基,卤素或C1-C4-烷基取代的C3-C6-环烷基,C3-C6-环烷基氧基或C3-C6-环烷基-C1-C4-烷基,和
A39代表氢,代表各自任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基或C1-C4-烷氧基,或者代表各自任选被氰基,卤素或C1-C4-烷基取代的C3-C6-环烷基,C3-C6-环烷基氧基或C3-C6-环烷基-C1-C4-烷基。
其中
Q1,Q2,R1和R2各自如上定义,
H2N-Ar (Ⅲ)
其中
Ar如上定义,
并且,如果适当,对得到的式(Ⅰ)化合物通过常规方法在上述取代基定义范围内进行进一步转化反应。
通式(Ⅰ)新的取代的三唑并吖嗪磺酰胺具有令人感兴趣的生物性能,使它们可用作植物处理剂。它们具有强的除草,杀菌和杀虫活性,并且特别具有极好的且选择性的除草作用。
本发明优选提供式(Ⅰ)化合物,其中
Q1代表氮或CH基团,
Q2代表氮或CH基团,
R1代表氢,氟,氯,溴或者代表各自任选被氟,氯,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基或二乙基氨基,
R2代表氢,氟,氯,溴或者代表各自任选被氟,氯,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基氨基,乙基氨基,正-或并-丙基氨基,二甲基氨基或二乙基氨基,
其中
m在各种情况下代表数1或2,
n在各种情况下代表数0,1或2,
A1代表各自任选被氰基,氟,氯,溴,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,或者代表各自任选被氰基,氟,氯,溴,甲基或乙基取代的环丙基,环丁基,环戊基或环己基,
A2代表各自任选被氟,氯或溴取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,正-或并-丙基亚磺酰基,甲基磺酰基,乙基磺酰基,正-或异-丙基磺酰基,
A3代表各自任选被氰基,氟,氯,溴,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,
A4代表各自任选被氰基,氟,氯,溴,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,
A5代表各自任选被氰基,氟,氯,溴,甲氧基或乙氧基取代的乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,代表各自任选被卤素取代的丙烯基或丁烯基,或者各自任选被氰基,氟,氯,溴,甲基或乙基取代的环丙基甲基,环丁基甲基,环戊基甲基或环己基甲基,
A6代表氟,氯,溴或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,丙烯基,丁烯基,丙烯基氧基或丁烯基氧基,
A7代表各自任选被氰基,氟,氯,溴,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,
A8代表氰基,硝基或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,
A9代表氰基,氟,氯或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,
A10代表氢,代表各自任选被氰基,氟,氯,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,或者代表各自任选被氰基,氟,氯,甲基或乙基取代的环丙基,环丁基,环戊基或环己基,
A11代表氢或者代表各自任选被氰基,氟,氯,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,乙酰基,丙酰基,正-或异-丁酰基,甲氧羰基,乙氧羰基,正-或异-丙氧羰基,甲基磺酰基,乙基磺酰基,正-或异-丙基磺酰基,
A12代表氢,氰基,氟,氯,溴或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,
A13代表氰基,氨基甲酰基,5,6-二氢-1,4,2-二噁嗪-3-基,氟,氯,溴,甲基,乙基,正-或异-丙基,乙酰基,丙酰基,正-或异-丁酰基,甲氧羰基,乙氧羰基,正-或异-丙氧羰基,
A14代表氢,代表氰基,氨基甲酰基,氟,氯,溴,甲基,乙基,正-或异-丙基,乙酰基,丙酰基,正-或异-丁酰基,甲氧羰基,乙氧羰基,正-或异-丙氧羰基,
A15代表氢,代表氰基,氨基甲酰基,氟,氯,溴,甲基,乙基,正-或异-丙基,乙酰基,丙酰基,正-或异-丁酰基,甲氧羰基,乙氧羰基,正-或异-丙氧羰基,或者与A14一起代表稠合的苯并基团,
A16代表氢,氰基,氟,氯,溴或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,正-或异-丙基亚磺酰基,甲基磺酰基,乙基磺酰基,正-或异-丙基磺酰基,
A17代表氢,氰基,氟,氯,溴或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,
A18代表氢,氰基,氟,氯,溴或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,
A19代表氢,甲基,乙基,正-或异-丙基,
A20代表甲基,乙基,正-或异-丙基或者代表丙烯基或丁烯基,
A21代表氰基,氟,氯,溴,甲基,乙基,正-或异-丙基,或者代表三氟甲基,
A22代表甲基,乙基,正-或异-丙基,
A23代表甲基,乙基,正-或异-丙基,
A24其本身代表甲基,乙基,正-或异-丙基或者与A23一起代表乙烷-1,2-二基(二亚甲基)或丙烷-1,3-二基(三亚甲基),
A25代表氰基,氟,氯,溴,甲基,乙基,正-或异-丙基,或者代表三氟甲基,
A26代表甲基,乙基,正-或异-丙基,
A27代表氰基,氟,氯,溴,甲基,乙基,正-或异-丙基,或者代表三氟甲基,
A28代表氢,乙酰基,丙酰基,正-或异-丁酰基,甲氧羰基,乙氧羰基,正-或异-丙氧羰基,甲基磺酰基,乙基磺酰基,正-或异-丙基磺酰基,
A29代表氰基,氟,氯,溴,甲基,乙基,正-或异-丙基,或者代表三氟甲基,
A30代表氢,甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,
A31代表氢或者甲基,乙基,正-或异-丙基,
A32代表氰基,氟,氯,溴,甲基,乙基,正-或异-丙基,或者代表三氟甲基,
A33代表氢,甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,
A34代表氢,甲基,乙基,正-或异-丙基,
A35代表氰基,氟,氯,溴,甲基,乙基,正-或异-丙基,或者代表三氟甲基,
A36代表氢,甲基,乙基,正-或异-丙基,环丙基,环丁基,环戊基,环己基或苯基,
A37代表氢,甲基,乙基,正-或异-丙基,环丙基,环丁基,环戊基,环己基或苯基,
A38代表氢,氟,氯,溴,代表各自任选被氰基,氟,氯,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,或者代表各自任选被氰基,氟,氯,甲基或乙基取代的环丙基,环丁基,环戊基,环己基,环丙基氧基,环丁基氧基,环戊基氧基,环己基氧基,环丙基甲基,环丁基甲基,环戊基甲基或环己基甲基,
A39代表氢,代表各自任选被氰基,氟,氯,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,或者代表各自任选被氰基,氟,氯,甲基或乙基取代的环丙基,环丁基,环戊基,环己基,环丙基氧基,环丁基氧基,环戊基氧基,环己基氧基,环丙基甲基,环丁基甲基,环戊基甲基或环己基甲基,
本发明还优选提供式(Ⅰ)化合物的锂盐,钠盐,钾盐,镁盐,钙盐,铵盐,C1-C4-烷基-铵盐,二-(C1-C4-烷基)-铵盐,三-(C1-C4-烷基)-铵盐,四-(C1-C4-烷基)-铵盐,三-(C1-C4-烷基)-锍,C5-或C6-环烷基铵盐和二-(C1-C2-烷基)-苄基-铵盐。
上述一般或优选的基团定义适用于式(Ⅰ)终产物,并且还相应地适用于每种情况下制备所需要的起始物或中间体。这些基团定义可以根据需要相互组合,即包括给定各范围之间的组合。
式(Ⅱ)提供了在制备式(Ⅰ)化合物的本发明方法中用作起始物的三唑并吖嗪磺酰氯的一般定义。在式(Ⅱ)中,Q1,Q2,R1和R2各自优选具有上文已经指明的,与描述本发明式(Ⅰ)化合物相关的,作为优选的Q1,Q2,R1和R2的那些定义。
式(Ⅱ)起始物是已知的和/或可以通过本身已知的方法制备(参见EP142152,EP244847,EP375076,US4605433,US5163995,WO89/10368)。
式(Ⅲ)提供了在本发明方法中也用作起始物的氨基(杂)芳烃的一般定义。在式(Ⅲ)中,Ar优选具有上文已经指明的,与描述本发明式(Ⅰ)化合物相关的,作为优选的Ar的定义。
式(Ⅲ)起始物是已知的和/或可以通过本身已知的方法制备(参见EP142152,EP244847,EP375076,US4605433,US5163995,WO89/10368)。
用于本发明方法的合适的反应助剂一般是常规无机碱或有机碱或酸受体。优选包括碱金属或碱土金属乙酸盐,氨化物,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,氨化锂,氨化钠,氨化钾或氨化钙,碳酸钠,碳酸钾或碳酸钙,碳酸氢钾,碳酸氢钠或碳酸氢钙,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;还有碱性有机氮化合物,例如三甲胺,三乙胺,三丙胺,三丁基胺,乙基二异丙基胺,N,N-二甲基-环己基胺,二环己基胺,乙基-二环己基胺,N,N-二甲基苯胺,N,N-二甲基-苄基胺,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,4-二甲基氨基-吡啶,N-甲基哌啶,1,4-二氮杂双环[2.2.2]-辛烷(DABCO),1,5-二氮杂双环[4.3.0]-壬-5-烯(DBN)或1,8-二氮杂双环[5.4.0]-十一-7-烯(DBU)。
进行本发明方法合适的稀释剂特别是惰性有机溶剂。优选包括脂肪族,脂环族或芳香族的、任意卤化的烃,例如,汽油,苯,甲苯,二甲苯,氯苯,二氯苯,石油醚,己烷,环己烷,二氯甲烷,氯仿,四氯化碳;醚类,例如二乙醚,二异丙基醚,二噁烷,四氢呋喃或乙二醇二甲基醚或乙二醇二乙基醚;酮类,例如丙酮,丁酮,或甲基异丁基酮;腈类,例如乙腈,丙腈或丁腈;酰胺类,例如N,N-二甲基甲酰胺,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酸三酰胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜类,例如二甲亚砜;醇类,例如甲醇,乙醇,正-或异-丙醇,乙二醇单甲基醚,乙二醇单乙基醚,二甘醇单甲基醚,二甘醇单乙基醚以及它们与水的混合物或纯水。
进行本发明方法时,反应温度可以在相当宽的范围内变化。一般情况下,反应在0℃和100℃之间的温度下进行,优选在10℃和60℃之间的温度下进行。
本发明方法一般在大气压下进行。但是也可以在高压或低压下进行本发明方法-一般在0.1至10巴之间。
在进行本发明方法时,一般以大约等摩尔量使用起始物。但是,也可以以相对大的过量使用其中之一成分。反应一般在反应助剂的存在下在合适的稀释剂中进行,并且一般在需要的温度下将反应混合物搅拌数小时。通过常规方法进行后处理(参见制备实施例)。
本发明式(Ⅰ)活性化合物可以用作脱叶剂,干燥剂,杀稻草剂,特别是作为杀杂草剂。从广义上说,所谓杂草被理解是在其所不期望的地点生长的所有植物。本发明物质是作为天生性除草剂还是选择性除草剂主要取决于使用的量。
例如,与下面的植物相关,可以使用本发明活性化合物:
双子叶杂草种类:芥属(Sinapis),独行菜属(Lepidium),猪殃殃属(Galium),繁缕属(Stellaria),母菊属(Matricaria),春黄菊属(Anthemis),辣子草(Galinsoga),藜属(Chenopodium),荨麻属(Urtica),千里光属(Senecio),苋属(Amaranthus),马齿苋属(Portulaca),苍耳属(Xanthium),旋花属(Convolvulus),甘薯属(Ipomoea),蓼属(Polygonum),田菁(Sesbania),豚草属(Ambrosia),蓟属(Cirsium),飞廉属(Carduus),苦苣菜属(Sonchus),茄属(Solanum),焊菜属(Rorippa),水松叶属(Rotala),母草属(Lindernia),野芒麻属(Lamium),婆婆纳属(Veronica),苘麻属(Abutilon),刺果(Emex),曼陀罗属(Datura),堇菜属(Viola),鼬瓣花属(Galeopsis),罂粟属(Papaver),矢车菊属(Centaurea),车轴草属(Trifolium),毛茛属(Ranunculus)和蒲公英属(Taraxacum)。
双子叶作物种类:棉属(Gossypium),大豆属(Glycine),Beta,胡萝卜属(Daucus),菜豆属(Phaseolus),Pisum,茄属(Solanum),亚麻属(Linum),甘薯属(Ipomoea),巢菜属(Vicia),烟草属(Nicotiana),番茄属(Lycopersicon),花生(Arachis),芥属(Brassica),莴苣属(Lactuca),香瓜属(Cucumis)和臭瓜(Cucurbita)。
单子叶杂草种类:稗属(Echinochloa),狗尾草属(Setaria),黍属(Panicum),马唐属(Digitaria),梯牧属(Phleum),早熟禾属(Poa),羊茅属(Festuca),蟋蟀菜属(Eleusine),臂形草属(Brachiaria),黑麦草属(Lolium),雀麦属(Bromus),燕麦属(Avena),莎草属(Cyperus),蜀黍属(Sorghum),冰草属(Agropyron),Cycnodon,雨久花属(Monchoria),飘拂草属(Fimbristylis),慈姑(Sagittaria),荸荠属(Eleocharis),镳草(Scirpus),雀稗草(Paspalum),Ischaemum,尖瓣花属(Sphenoclea),龙爪茅属(Dactyloctenium),剪股颍属(Agrostis),看麦娘属(Alopecurus),和Apera。
单子叶作物种类:稻属(Oryza),玉米属(Zea),小麦属(Triticum),大麦属(Hordeum),燕麦属(Avena),黑麦属(Secale),蜀黍属(Sorghum),黍属(Panicum),甘蔗(Saccharum),菠萝(Ananas),天门冬属(Asparagus)和葱属(Allium)。
但是本发明活性化合物的用途不受这些种类的限制,而是以相同的方式扩展到其它植物。
根据浓度,本发明化合物适于例如在工业场所和铁道,有或没有树木的路或广场上全部控制杂草。这些化合物也同样被用来在多年生种植植物场所,草坪,运动场和牧场控制杂草,所述多年生种植植物场所是例如树林,装饰性种植的树,果园,葡萄园,柠檬园,坚果园,香蕉种植园,咖啡种植园,茶种植园,橡胶种植园,油棕种植园,可可种植园,软果种植植物和蛇麻草田,以及用来在年生农作物场所选择性控制杂草。
本发明式(Ⅰ)化合物特别适合于在芽前和芽后,在单子叶和双子叶农作物中选择性控制单子叶杂草和双子叶杂草。
本发明式(Ⅰ)活性化合物在某种程度上也具有强的杀微生物作用,并且实际上能用来防治不期望的微生物,本发明活性化合物因而也适合用作杀真菌剂和杀细菌剂。
植物保护中的杀真菌剂被用来防治根肿菌(Plasmodiophoromycetes),卵孢真菌(Oomycetes),壶菌(Chytridiomycetes),接合菌亚纲(Zygomycetes),子囊菌(Ascomycetes),担子菌纲(Basidiomycetes)和半知菌纲(Deutermycetes)。
植物保护中的杀细菌剂被用来防治假单孢菌科(Pseudomonadaceae),根瘤菌科(Rhizobiaceae),肠杆菌科(Enterobacteriaceae),棒状杆菌科(Corynebacteriaceae)和链霉菌科(Streptomycetaceae)。
作为例子可以提到上述属名下的真菌病和细菌病的病原微生物,但是不受此限制:
黄单孢菌属种类(Xanthomonas),例如田野稻黄单孢菌变种(Xanthomonas campestris pv.oryzae);
假单孢菌属种类(Pseudomonas),例如丁香黄瓜角斑病假单孢菌变种(Pseudomonas syringae pv.lachrymans);
欧文氏杆菌属种类(Erwinia),例如解淀粉欧文氏杆菌(Erwiniaamylovora);
腐霉属种类(Pythium),例如终极腐霉(Pythium ultimum);
疫霉属种类(Phytophthora),例如蔓延疫霉(Phytophthorainfestans);
假霜霉属种类(Pseudoperonospora),例如律草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(Pseudoperonosporacubensis);
单轴霉属种类(Plasmopara),例如葡萄生单轴霉(Plasmoparaviticola);
盘梗霉属种类(Bremia),例如莴苣盘梗霉(Bremia lactucae);
霜霉属种类(Peronospora),例如豌豆霜霉(Peronospora pisi)或芸苔霜霉(Peronospora brassicae);
白粉菌属种类(Erysiphe),例如禾白粉菌(Erysiphe graminis);
单丝壳菌属种类(Sphaerotheca),例如苍耳单丝壳菌(Sphaerotheca fuliginea);
柄球菌属种类(Podosphaera),例如苹果白粉病柄球菌(Podosphaera leucotricha);
黑星菌属种类(Venturia),例如苹果黑星菌(Venturiainaequalis);
核腔菌属种类(Pyrenophora),例如圆核腔菌(Pyrenophora teres)或麦类核腔菌(Pyrenophora graminea)
(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));
旋孢菌属种类(Cochliobolus),例如禾旋孢菌(Cochliobolussativus)
(分生孢子形式:长蠕孢(Drechslera),同义词:长蠕孢(Helminthosporium));
单胞锈菌属种类(Uromyces),例如疣顶单胞锈菌(Uromycesappendiculatus);
柄锈菌属种类(Puccinia),例如隐匿柄锈菌(Pucciniarecondita);
核盘菌属种类(Sclerotinia),例如油菜核盘菌(SclerotiniaSclerotiorum);
腥黑粉菌属种类(Tilletia),例如小麦网腥黑粉菌(Tilletiacaries);
黑粉菌属种类(Ustilago),例如裸黑粉菌(Ustilago nuda)或燕麦黑粉菌(Ustilago avenae);
薄膜革菌属种类(Pellicularia),例如佐佐木氏薄膜革菌(Pellicularia sasakii);
Pyricularia种类,例如Pyricularia oryzae;
镰孢属种类(Fusarium),例如大刀镰孢(Fusarium culmorum);
葡萄孢属种类(Botrytis),例如灰色葡萄孢(Botrytis cinerea);
壳针孢属种类(Septoria),例如颖枯壳针孢(Septoria nodorum);
小球腔菌属种类(Leptosphaeria),例如颖枯小球腔菌(Leptosphaeria nodorum);
尾孢属种类(Cercospora),例如Cercospora canescens;
链格孢属种类(Alternaria),例如甘蓝黑斑病链格孢(Alternariabrassicae);
假尾孢属种类(Pseudocercosporella),例如Pseudocercosporella herpotrichoides。
植物对在防治植物病害所需要的浓度时的一些活性化合物的好的耐受性允许处理植物的地上部分,植物繁殖根株和种子,和处理土壤。
本发明活性化合物非常成功地用于防治水果和蔬菜生长中的病害,例如抗柄球菌属(Podosphaera)和单丝壳菌属(Sphaerotheca)种类,也防治稻病害,例如Pyricularia oryzae。
本发明式(Ⅰ)活性化合物在某种程度上也适合防治动物害虫,优选节肢动物和线虫,特别是农业,森林,贮存产品和材料保护,以及卫生领域所遇到的昆虫和蛛形纲。其一般对敏感和抗性物种是有活性的,并且抗发育的所有或某些阶段。上述害虫包括:
等足目(Isopoda),例如Oniscus aselluse,鼠妇(Armadillidiumvulgare)和Porcellio scaber;
多足纲目(Diplopoda),例如Blaniulus gutttulatus;
唇足亚纲目(Chilopoda),例如Geophilus carpophagus和蛐蜒目种(Scutigera spec.);
综合纲目(Symphyla),例如Scutigerella immaculata;
缨尾目(Thysanura),例如西洋衣鱼(Lepisma saccharina);
弹尾目(Collembola),例如Onychiurus armatus;
直翅目(Orthoptera),例如东方非蠊(Blatta orientalis),美洲大蠊(Periplaneta americana),马德拉非蠊(Leucophaea maderae),德国小蠊(Blattella germanica),灶马(Acheta domesticus),蝼蛄属(Gryllotalpa spp.),热带飞蝗(Locusta migratoriamigratorioides),长额负蝗(Melanoplus differentialis)和Schistocerca gregaria;
革翅目(Dermaptera),例如欧洲球螋(Forficula auricularia);
等翅目(Isoptera),例如白蚁属(Reticulitermes spp.);
虱目(Anoplura),例如头虱(Pediculus humanus corporis),盲虱属(Haematopinus spp.)和长额虱(Linognathus spp.);
食毛目(Mallophaga),例如羽虱属(Trichodectes spp.)和Damalinea spp.;
缨翅目(Thysanoptera),例如温室条蓟马(Hercinothripsfemoralis)和棉蓟马(Thrips tabaci);
异翅亚目(Heteroptera),例如褐盾蝽属(Eurygasterspp.),Dysdercus intermedius,甜菜拟网蝽(Piesma quadrata),臭虫(Cimex lectularius),Rhodnius prolixus和吸血猎蝽属(Triatomaspp.);
同翅亚目(Homoptera),例如Aleurodes brassicae,棉粉虱(Bemisia tabaci),温室白粉虱(Trialeurodes vaporariorum),棉蚜(Aphis gossypii),甘蓝蚜(Brevicoryne brassicae),茶鹿隐瘤额蚜(Cryptomyzus ribis),蚕豆蚜(Aphis fabae),Aphis pomi,苹果绵蚜(Eriosoma lanigerum),桃大尾蚜(Hyalopterus arundinis),Macrosiphum avenae,瘤额蚜(Myzus spp.),Pemphigus spp.,忽布瘤额蚜(Phorodon humuli),Phylloxera vastatrix,粟缢管蚜(Rhopasiphumpadi),叶蝉属(Empoasca spp.),Euscelis bilobatus,黑尾叶蝉(Nephotettix cincticeps),李蜡蚧(Lecanium corni),油橄榄盔(Saissetia oleae),稻灰飞虱(Laodelphax striatellus),褐稻虱(Nilaparvata lugens),红圆蚧(Aonidiella aurantii),Aspidiotushederae,粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.);
鳞翅目(Lepidoptera),例如,红铃虫(Pectinophora gossypiella),松尺蠖(Bupalus piniarius),Cheimatobia brumata,Lithocolletisblancardella,樱桃巢蛾(Hyponomeuta padella),小菜蛾(Plutellamaculipennis),天幕毛虫(Malacosoma neustria),Euproctischrysorrhoea,毒蛾属(Lymantria spp.),棉叶穿孔潜蛾(Bucculatrixthurberiella),Phyllocni sti citrella,地老虎(Agrotis spp.),切根虫(Euxoa spp.),褐夜蛾(Feltia spp.),埃及金刚钻(Eariasinsulana),夜蛾属(Heliothis spp.),甜菜夜蛾(Spodoptera exigua),甘蓝夜蛾(Mamestra brassicae),Panolis flammea,斜纹夜蛾(Prodenia litura),夜蛾属(Spodoptera spp.),粉纹夜蛾(Trichoplusia ni),苹果蠹蛾(Carpocapsa pomonella),粉蝶属(Pieris spp.),螟(Chilo spp.),Pyrausta nubilalis,Ephestiakuehniella,大黄螟(Galleria mellonella),袋衣蛾(Tineolabisselliella),网衣蛾(Tinea pellionella),褐织叶蛾(Hofmannophila pseudospretella),Cacoecia podana,Capuareticulana,云杉卷叶蛾(Choristoneura fumiferana),葡萄果蠹蛾(Clysia ambiguella),茶黄卷叶蛾(Homona magnanima)和栎绿卷叶蛾(Tortrix viridana);
鞘翅目(Coleoptera),例如,家具窃蠹(Anobium punctatum),Rhizopertha dominica,大豆象(Acanthoscelidesobtectus),Bruchidius obtectus,家天牛(Hylotrupes bajulus),Agelastica alni,甲铃薯甲虫(Leptinotarsa decemlineata),Phaedon cochleariae,叶甲属(Diabrotica spp.),油菜兰跳甲(Psylliodes chrysocephala),墨西哥豆瓢虫(Epilachna varivestis),Atomaria spp.,锯胸谷盗(Oryzaephilus surinamens),象甲属(Anthonomus spp.),米象属(Sitophilus spp.),Otiorrhynchussulcatus,香蕉蛛基象甲(Cosmopolites sordidus),Ceuthorrhynchus assimilis,苜宿叶象甲(Hypera posttica),皮蠹属(Dermestes spp.),皮蠹属(Trogoderma spp.),皮蠹属(Anthrenusspp.),黑皮蠹(Attagenue spp.),粉蠹(Lyctus spp.),Meligethesaeneus,蛛甲属(Ptinus spp.),金黄蛛甲(Niptus hdoleucus),麦蛛甲(Gibbium psylliodes),拟谷稻属(Tribolium spp.),黄粉甲(Tenebriomolitor),扣甲属(Agriotes spp.),金针虫属(Conederus spp.),Melolontha meiolontha,六月金龟子(Amphimallon solstitialis)和Costelytra zealandica;
膜翅属(Hymenoptera),例如锯角叶蜂属(Diprion spp.),叶蜂属(Hoplocampa app.),蚁(Lasius spp.),厨蚁(Monomorium pharaonis),和胡蜂(Vespa spp.);
双翅属(Diptera),例如,咿蚊(Aedes spp.),斑按蚊属(Anophelesspp.),库蚊(Culex spp.),黄猩猩果蝇(Drosophila melanogaster),家蝇(Musca spp.),厩蝇(Fannia spp.),红头丽蝇(Calliphoraerythrocephala),丝光绿蝇(Lucilia spp.),Chrysomyia spp.,疽蝇属(Cuterebra spp.),Gastrophilus spp.,Hyppobosca spp.,螫蝇属(Stomoxys spp.),鼻蝇属(Oestrus spp.),皮蝇属(Hydoderma spp.),牛虻属(Tabanus spp.),Tannia spp.,Bibio hortulanus,瑞典麦杆蝇(Oscinella frit),麦蝇(Phorbia spp.),甜菜潜叶花蝇(Pegomyiahyoscyami),地中海实蝇(Ceratitis capitata),油橄榄实蝇(Dacusoleae)和欧洲大蚊(Tipula paludosa);
蚤目(Siphonaptera),例如,东方鼠蚤(Xenopsylla cheopis)和角叶蚤属(Ceratophyllus spp.);
蛛形纲(Arachnida),例如Sciopio maurus和黑寡妇球腹蛛(Latrodectus mactans);
蜱螨目(Acarina),例如,粗脚粉螨(Acarus siro),隐喙蚍(Argasspp.),喙蜱属(Ornithodoros spp.),鸡皮刺螨(Dermanyssusgallinae),Eriophyes ribis,橘锈螨(Phyllocoptruta oleivora),牛蜱属(Boophilus spp.),头蜱属(Rhipicephalus spp.),花蜱属(Amblyomma spp.),Hyalomma spp.,硬蚍(Ixodes spp.),蛘螨属(Psoroptes spp.),恙螨属(Chorioptes spp.),疥螨(Sarcoptes spp.),线螨属(Tarsonemus spp.),苜宿苔螨(Bryobia praetiosa),红蜘蛛(Panonychus spp.),和红叶螨属(Tetranychus spp.)。
植物寄生线虫包括,例如短体线虫属(Pratylenchus spp.),穿孔线虫属(Radopholus spp.),茎线虫属(Ditylenchus spp.),垫刃线虫属(Tylenchulus spp.),异皮线虫属(Heterodera spp.),球异皮线虫属(Globodera spp.),根结线虫属(Meloidogyne spp.),滑刃线虫属(Aphelenchoides spp.),长针线虫属(Longidorus spp.),剑线虫属(Xiphinema spp.),毛刺线虫属(Trichodorus spp.),垫刃线虫属(Tylenchus spp.),螺旋线虫属(Helicotylenchus spp.),盘旋线虫属(Rotylenchus spp.),小垫刃线虫属(Tylenchulus spp.)。
本发明活性化合物被特别成功地应用于例如杀蝴蝶幼虫,例如小菜蛾毛虫(Plutella maculipennis)。
活性化合物可以配制成常规制剂,例如溶液、乳液、可湿性粉末、悬浮剂、粉剂、细粉剂、糊剂、可溶性粉末、颗粒剂、混悬乳油、浸有活性化合物的天然的和合成的材料,和包裹在聚合物中的细微胶囊。
这些型剂可以用已知的方式生产,例如,通过将活性化合物与扩充剂即液体溶剂和/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。
用水作扩充剂的情况下,也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要有:芳香族化合物,如二甲苯,甲苯或烷基萘,氯代芳香族化合物和氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂肪烃,如环己烷或石蜡,例如矿物油馏份,矿物油和植物油,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,如二甲基甲酰胺和二甲亚砜,以及水。
合适的固体载体是: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、矾土和硅酸盐;用于颗粒剂的适合的固体载体有:例如压碎和破碎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:例如锯木屑、椰壳、玉米穗轴和烟茎;作为乳化剂和/或起泡剂合适的有: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,烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐,芳基磺酸盐以及蛋白水解产物;作为分散剂合适的有: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,如羧甲基纤维素和粉状、颗粒或乳胶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。其它的添加剂可以是矿物油和植物油。
也可以使用色料,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,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%。
对于控制杂草,本发明活性化合物可以使用其本身或者以其制剂使用,也可以作为与已知除草剂的混合物使用,在这种情况下可以是即用制剂或容器混合物。
用于所述混合物的合适的共同成分是已知的除草剂,例如N-酰苯胺类,例如吡氟草胺和敌稗;芳基羧酸类,例如二氯吡啶甲酸,麦草畏和毒莠定;芳基氧基链烷酸类,例如2,4-滴,2,4-滴丁酸,2,4-滴丙酸,氟草烟,2甲4氯,2甲4氯丙酸和绿草定;芳基氧基苯氧基链烷酸酯类,例如禾草灵,噁唑禾草灵,吡氟禾草灵,吡氟氯禾灵和喹禾灵;吖嗪酮类,例如杀草敏和哒草伏;氨基甲酸酯类,例如氯苯胺灵,甜菜安,甜菜宁和苯胺灵;氯代N-乙酰苯胺类,例如甲草胺,乙草安,丁草安,吡草安,异丙甲草胺,丙草安和毒草安;二硝基N-酰苯胺类,例如安磺灵,二甲戊乐灵和氟乐灵;二苯基醚类,例如三氟羧草醚,甲羧除草醚,乙羧氟草醚,氟磺胺草醚,halosafen,乳氟禾草灵和乙氧氟草醚;脲类,例如氯麦隆,敌草隆,伏草隆,异丙隆,利谷隆和甲基苯噻隆;羟胺类,例如禾草灭,烯草酮,噻草隆,稀禾定和肟草酮;咪唑啉酮类,例如咪草烟,咪草酯,灭草烟和灭草喹;腈类,例如溴苯腈,敌草腈和碘苯腈;氧乙酰胺类,例如苯噻草胺;磺酰脲类,例如amidosulfuron,苄嘧黄隆,氯嘧黄隆,氯黄隆,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,例如克草猛,灭草特,燕麦畏,茵达灭,禾草畏,草达灭,苄草丹,杀草丹和野燕畏;三嗪类,例如莠去津,氰草津,西玛津,西草净,特丁净和terbutylazine;三嗪酮类,例如环嗪酮,苯嗪草酮和嗪草酮;其它类,例如氨基三唑,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,哒草特,二氯喹啉酸,喹草酸,草硫磷和灭草环。
也可以是与其它已知活性化合物的混合物,所述其它活性化合物例如杀真菌剂,杀昆虫剂,杀螨剂,杀线虫剂,鸟驱避剂,植物营养剂和改善土壤结构的试剂。
这些活性化合物可以使用其本身,其制剂形式或者以通过进一步稀释而从中制备的使用形式使用,例如即用型溶液,混悬剂,乳剂,粉剂,糊剂和颗粒剂。它们可以以常规方式使用,例如通过浇灌,喷雾,弥雾或播撒。
本发明活性化合物可以在植物芽前或芽后施用。其也可以在播种前掺合到土壤中。
使用的活性化合物的量可以在一个基本的范围内变化。这主要取决于期望的效果的性质。一般情况下,施用比例是每公顷土壤面积使用1g-10kg活性化合物,优选每公顷土壤面积使用5g-5kg活性化合物。
室温(大约20℃)下,将2.1g(10mmol)2-甲基硫基-6-正丁酰苯胺,2.5g(10mmol)5,7-二甲基-1,2,4-三唑并[1,5-a]嘧啶-2-磺酰氯和30ml吡啶的混合物搅拌大约15小时。接着水泵抽真空下小心蒸馏出吡啶,并将残余物溶解于100ml二氯甲烷,用2N盐酸和用水各洗涤两次,硫酸镁干燥并过滤。水泵抽真空下浓缩滤液,无定形残余物通过用乙醇处理而结晶,吸滤分离产物。
得到2.8g(理论量的67%)5,7-二甲基-N-(2-甲基硫基-6-正丁酰基-苯基)-1,2,4-三唑并[1,5-a]嘧啶-2-磺酰胺,熔点138℃。
实施例2
首先将3.2g(7.5mmol)5,7-二甲基-N-(2-甲基硫基-6-正丁酰基-苯基)-1,2,4-三唑并[1,5-a]嘧啶-2-磺酰胺加入到60ml氯仿中,该溶液与1.8g3-氯-过苯甲酸(70%强度)混合。然后反应混合物在室温(大约20℃)下搅拌大约60分钟,并接着在水泵抽真空下浓缩。残余物溶解于40ml乙醇,吸滤分离得到的结晶产物。
得到2.3g(理论量的70%)5,7-二甲基-N-(2-甲基亚磺酰基-6-正丁酰基-苯基)-1,2,4-三唑并[1,5-a]嘧啶-2-磺酰胺,熔点255℃(分解)。实施例3
首先将2.1g(5mmol)5,7-二甲基-N-(2-甲基硫基-6-正丁酰基-苯基)-1,2,4-三唑并[1,5-a]嘧啶-2-磺酰胺加入到50ml氯仿中,该溶液与2.8g3-氯-过苯甲酸(70%强度)混合。然后反应混合物在室温(大约20℃)下搅拌大约2小时,并接着在水泵抽真空下浓缩。残余物溶解于30ml乙醇,吸滤分离得到的结晶产物。
得到2.0g(理论量的89%)5,7-二甲基-N-(2-甲基磺酰基-6-正丁酰基-苯基)-1,2,4-三唑并[1,5-a]嘧啶-2-磺酰胺,熔点236℃(分解)。
类似于制备实施例1-3,并且根据本发明制备方法的一般性说明,也可以制备例如下面表1中列出的式(Ⅰ)化合物。表1:式(Ⅰ)化合物的实施例表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
应用实施例
实施例A
芽前试验
溶剂: 5份重量丙酮
乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂混合,加入所述量乳化剂,用水将乳油稀释到需要的浓度。
在正常土壤中播种试验植物的种子。大约24小时后,以每单位面积施用特定量的期望的活性化合物的方式,用活性化合物制剂对土壤喷雾。选择喷雾液的浓度,使得以1000升水/公顷施用特定期望量的活性化合物。
三星期后,以与未处理对照物生长相比较的破坏百分率测定对植物的破坏程度。数据说明:
0%=没有效果(象未处理对照物一样)
100%=完全破坏
在该项试验中,例如制备实施例4,5,6,13,14,17,18,19,22,23,25,34,35,38,39,43,60,63,73,74,75,76,77,82,84,85,104,115,118和121的化合物显示出强的除杂草活性(参见下面实施例A的表),并且农作物例如小麦,大豆和棉花对它们中的一些有好的耐受性。实施例A的表:芽前试验/温室1)化合物制 施用比例 小麦 看麦粮属 雀麦属 稗属 黑麦草属 猪秧秧属 母菊属 茄属备实施例序 (活性成分克数/公顷)号13 250 5 100 - 100 80 100 100 10014 125 - 95 95 100 90 70 100 1002)化合物制 施用比例 小麦 看麦娘属 莎草属 马唐属 稗属 猪秧秧属 母菊属 茄属器实施例序 (活性成分克数/公顷)号43 125 10 100 100 100 100 100 100 1003)化合物制 施用比例 小麦 看麦娘属 莎草属 马唐属 猪秧秧属 辣子草 母菊属 茄属备实施例序 (活性成分克数/公顷)号60 500 20 95 100 80 95 95 95 954)化合物制 施用比例 大豆 雀麦属 稗属 黑麦草属 早熟禾属 猪殃殃属 辣子草 母菊属 茄属备实施例序 (活性成分克数/公顷)号75 1000 10 80 90 95 95 95 100 95 955)化合物制 施用比例 棉花 看麦娘属 马唐属 稗属 早熟禾属 辣子草 母菊属 茄属备实施例序 (活性成分克数/公顷)号104 250 0 80 90 80 80 90 95 906)化合物制 施用比例 小麦 大豆 马唐属 早熟禾属 辣子草 母菊属 茄属备实施例序 (活性成分克数/公顷)号115 100 0 0 95 - 100 95 90121 125 0 0 - 70 95 95 907)化合物制 施用比例 看麦娘属 雀麦属 莎草属 稗属 黑麦草属 猪殃殃属 母菊属 茄属备实施例序 (活性成分克数/公顷)号76 500 100 100 100 100 100 100 100 1008)化合物制 施用比例 看麦娘属 莎草属 马唐属 稗属 猪殃殃属 辣子草 母菊属 茄属备实施例序 (活性成分克数/公顷)号73 250 - 95 95 95 95 95 95 9574 250 80 - 95 90 90 100 95 959)化合物制备 施用比例 看麦娘属 莎草属 稗属 猪殃 辣子草 母菊属 茄属实施例 (活性成份克数/公顷) 殃属5 125 95 90 95 95 95 95 904 125 90 95 90 90 95 95 9085 125 90 90 90 90 95 95 9084 250 80 95 70 90 95 95 9519 250 80 100 95 - 95 95 -6 500 95 90 90 95 95 95 9534 250 99 95 90 100 - 100 10035 250 95 - 95 95 100 95 9522 250 80 - 95 100 100 95 9523 250 - - 95 100 100 95 -25 500 80 80 100 100 - 100 100118 250 80 95 95 90 95 95 9510)化合物 施用比例 看麦娘属 马唐属 稗属 猪殃殃属 母菊属 茄属制备实施例 (活性成分克数/公顷)序号82 500 95 95 100 100 100 10063 125 100 95 100 100 100 10011)化合物 施用比例 看麦娘属 马唐属 稗属 早熟禾属 猪殃殃属 辣子草 母菊属 茄属制备实施例 (活性成分克数/公顷)序号17 250 95 95 95 95 95 95 9518 250 90 90 95 90 95 100 100 9512)化合物 施用比例 看麦娘属 猪殃殃属 母菊属 茄属制备实施例 (活性成分克数/公顷)序号38 500 80 100 100 9539 500 80 100 100 10013)化合物 施用比例 莎草属 稗属 黑麦草属 猪殃殃属 母菊属 茄属制备实施例 (活性成分克数/公顷)序号77 500 95 90 80 95 100 95实施例B芽后试验溶剂: 5份重量丙酮乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂混合,加入所述量乳化剂,用水将乳油稀释到需要的浓度。
用活性化合物制剂对高5-15cm的试验植物喷雾,使对每单位面积施用特定量的期望的活性化合物。选择喷雾液的浓度,使以1000L水/公顷施用特定期望量的活性化合物。三星期后,以与未处理对照物生长相比较的破坏百分率测定对植物的破坏程度。数据说明:
0%=没有效果(象未处理对照物一样)
100%=完全破坏
在该项试验中,例如制备实施例6,17,18,19,22,60,63,73,76,77,82,84,118和121的化合物显示出强的除杂草活性(参见下面实施例B的表),并且无一例外地农作物例如小麦对它们有好的耐受性。实施例B的表:芽后试验/温室1)化合物制备实 施用比例 小麦 茴麻属 曼陀罗属 甘薯属 母菊属 茄属 苍耳属施例序号 (活性成分克数/公顷)84 125 10 - 90 90 80 90 7019 1000 - 95 90 95 95 95 1006 125 10 95 90 80 90 95 7022 500 5 100 95 95 100 90 100118 250 10 95 95 95 90 100 10073 125 20 95 95 90 100 95 10060 125 5 90 90 80 - 90 70121 500 5 - 60 100 70 95 9576 500 20 95 70 90 95 95 10077 500 - 95 - 80 100 95 10017 30 10 95 90 90 95 90 952)化合物制 施用比例 小麦 黑麦草属 蜀黍属 曼陀罗属 甘薯属 母菊属 茄属 苍耳属备实施例序 (活性成分克数/公顷)号82 500 - 95 95 100 100 100 100 10018 125 10 80 80 90 90 100 90 953)化合物制 施用比例 看麦娘 黑麦草属 蜀黍属 曼陀罗属 甘薯属 母菊属 茄属 苍耳属备实施例序 (活性成分克数/公顷)属号63 125 90 80 95 95 95 95 100 95实施例C单丝壳菌(Sphaerotheca)试验(黄瓜)/保护性的溶剂: 4.7份重量的丙酮乳化剂:0.3份重量的烷基芳基聚乙二醇醚
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,用活性化合物制剂喷雾幼嫩植物直到露湿。喷雾层风干后,将苍耳单丝壳菌(Sphaerotheca fuliginea)真菌的分生孢子细撒在植物上。
接着植物放置在23~24℃且相对空气湿度是大约75%的温室中。
接种后10天进行评价。
在该项试验中,例如制备实施例4,5,19和85的化合物显示出强的活性(参见下面的表C)。表C单丝壳菌(Spaerotheca)试验(黄瓜)/保护性的活性化合物 活性化合物浓度为100ppm时相对于未处
为了制备活性化合物的合适的制剂,将1份重量的活性化合物与所述量的溶剂和乳化剂混合,用水将乳油稀释到期望的浓度。
为了试验保护活性,用活性化合物制剂喷雾幼嫩植物直到露湿。喷雾层风干后,通过细尘播撒用苹果霉苹果白粉病柄球菌(Podosphaeraleucotricha)病原微生物的分生孢子接种植物。
然后将植物放置在23℃且相对空气湿度是大约70%的温室中。
接种后10天进行评价。
在该项试验中,例如制备实施例4,5,19和85的化合物显示出强的活性(参见下面的表D)。表D丙球菌(Podosphaera)试验(苹果)/保护性的活性化合物 活性化合物浓度为100ppm时相对于未处
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂和所述量乳化剂混合,用水将乳油稀释到需要的浓度。
通过浸入到期望浓度的活性化合物的制剂中来处理甘蓝叶(Brassica oleracea),并在叶子还湿润的时候用小菜蛾(Plutellamaculipennis)毛虫侵染。
一定时间后,测定杀伤百分率。100%表示所有的毛虫都已经被杀死;0%表示没有杀死一只毛虫。
Claims (7)
其中
Q1代表氮或CH基团,
Q2代表氮或CH基团,
R1代表氢,卤素或者代表C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基氨基或二-(C1-C4-烷基)氨基,它们各自任选被羟基,卤素或C1-C4-烷氧基取代,
R2代表氢,卤素或者代表C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基氨基或二-(C1-C4-烷基)氨基,它们各自任选被卤素取代,以及
Ar代表4-氰基-2,5-二氟苯基,2,6-二甲氧基-苯基,2-溴-3-三氟甲基-苯基,2-溴-5-三氟甲基-苯基,4-溴-2,6-二甲基-苯基,6-氯-吡啶-3-基-甲基或下面的5-元或6-元(杂)环基团中的一个:
其中
m在各种情况下代表数1或2,
n在各种情况下代表数0,1或2,
A1代表任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基或者代表任选被氰基,卤素或C1-C4-烷基取代的C3-C6-环烷基,
A2代表各自任选被卤素取代的C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基,
A3代表任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基,
A4代表任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基,
A5代表任选被氰基,卤素或C1-C4-烷氧基取代的C2-C4-烷基,代表任选被卤素取代的C2-C4-链烯基或者代表任选被氰基,卤素或C1-C4-烷基取代的C3-C6-环烷基-C1-C4-烷基,
A6代表卤素或者代表各自任选被卤素取代的C1-C4-烷基,C1-C4-烷氧基,C2-C4-链烯基或C2-C4-链烯基氧基,
A7代表任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基,
A8代表氰基,硝基或者任选被卤素取代的C1-C4-烷基,
A9代表氰基,卤素或者任选被卤素取代的C1-C4-烷基,
A10代表任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基或者代表任选被氰基,卤素或C1-C4-烷基取代的C3-C6-环烷基,
A11代表氢或者代表各自任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基,C1-C4-烷基-羰基,C1-C4-烷氧羰基或C1-C4-烷基磺酰基,
A12代表氢,氰基,卤素或任选被卤素取代的C1-C4-烷基,
A13代表氰基,氨基甲酰基,5,6-二氢-1,4,2-二噁嗪-3-基,卤素,C1-C4-烷基,C1-C4-烷基-羰基或C1-C4-烷氧羰基,
A14代表氢,代表氰基,氨基甲酰基,卤素,C1-C4-烷基,C1-C4-烷基-羰基或C1-C4-烷氧羰基,
A15代表氢,代表氰基,氨基甲酰基,卤素,C1-C4-烷基,C1-C4-烷基-羰基或C1-C4-烷氧羰基,或者与A14一起代表稠合的苯并基团,
A16代表氢,氰基,卤素或者代表各自任选被卤素取代的C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基,
A17代表氢,氰基,卤素或任选被卤素取代的C1-C4-烷基,
A18代表氢,氰基,卤素或任选被卤素取代的C1-C4-烷基,
A19代表氢或C1-C4-烷基,
A20代表C1-C4-烷基或C2-C4-链烯基,
A21代表氰基,卤素,C1-C4-烷基或C1-C4-卤代烷基,
A22代表C1-C4-烷基或C1-C4-卤代烷基,
A23代表C1-C4-烷基,
A24其自身代表C1-C4-烷基或者与A23一起代表C2-C4-链烷二基,
A25代表氰基,卤素,C1-C4-烷基或C1-C4-卤代烷基,
A26代表C1-C4-烷基,
A27代表氰基,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,
A28代表氢,二氟甲基,C1-C4-烷基-羰基,C1-C4-烷氧羰基或C1-C4-烷基磺酰基,
A29代表氰基,卤素,C1-C4-烷基或C1-C4-卤代烷基,
A30代表氢,C1-C4-烷基或C1-C4-烷氧基,
A31代表氢或C1-C4-烷基,
A32代表氰基,卤素,C1-C4-烷基或C1-C4-卤代烷基,
A33代表氢,C1-C4-烷基或C1-C4-烷氧基,
A34代表氢或C1-C4-烷基,
A35代表氰基,卤素,C1-C4-烷基或C1-C4-卤代烷基,
A36代表氢,C1-C4-烷基,C3-C6-环烷基或苯基,
A37代表氢,C1-C4-烷基,C3-C6-环烷基或苯基,
A38代表氢,卤素,代表各自任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基,C1-C4-烷氧基或C1-C4-烷硫基,或者代表各自任选被氰基,卤素或C1-C4-烷基取代的C3-C6-环烷基,C3-C6-环烷基氧基或C3-C6-环烷基-C1-C4-烷基,和
A39代表氢,代表各自任选被氰基,卤素或C1-C4-烷氧基取代的C1-C4-烷基或C1-C4-烷氧基,或者代表各自任选被氰基,卤素或C1-C4-烷基取代的C3-C6-环烷基,C3-C6-环烷基氧基或C3-C6-环烷基-C1-C4-烷基。
2.权利要求1的式(Ⅰ)化合物,特征在于
Q1代表氮或CH基团,
Q2代表氮或CH基团,
R1代表氢,氟,氯,溴或者代表各自任选被氟,氯,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基或二乙基氨基,
R2代表氢,氟,氯,溴或者代表各自任选被氟,氯,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基氨基,乙基氨基,正-或异-丙基氨基,二甲基氨基或二乙基氨基,
Ar代表4-氰基-2,5-二氟-苯基,2,6-二甲氧基-苯基,2-溴-3-三氟甲基-苯基,2-溴-5-三氟甲基-苯基,4-溴-2,6-二甲基-苯基,6-氯-吡啶-3-基-甲基或下面基团中的一个:其中m在各种情况下代表数1或2,n在各种情况下代表数0,1或2,
A1代表各自任选被氰基,氟,氯,溴,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,或者代表各自任选被氰基,氟,氯,溴,甲基或乙基取代的环丙基,环丁基,环戊基或环己基,
A2代表各自任选被氟,氯或溴取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,正-或异-丙基亚磺酰基,甲基磺酰基,乙基磺酰基,正-或异-丙基磺酰基,
A3代表各自任选被氰基,氟,氯,溴,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,
A4代表各自任选被氰基,氟,氯,溴,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,
A5代表各自任选被氰基,氟,氯,溴,甲氧基或乙氧基取代的乙基,正-或异-丙基,正-,异-,仲-或叔-丁基,代表各自任选被卤素取代的丙烯基或丁烯基,或者各自任选被氰基,氟,氯,溴,甲基或乙基取代的环丙基甲基,环丁基甲基,环戊基甲基或环己基甲基,
A6代表氟,氯,溴或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,丙烯基,丁烯基,丙烯基氧基或丁烯基氧基,
A7代表各自任选被氰基,氟,氯,溴,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,
A8代表氰基,硝基或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,
A9代表氰基,氟,氯或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,
A10代表氢,代表各自任选被氰基,氟,氯,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,或者代表各自任选被氰基,氟,氯,甲基或乙基取代的环丙基,环丁基,环戊基或环己基,
A11代表氢或者代表各自任选被氰基,氟,氯,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,乙酰基,丙酰基,正-或异-丁酰基,甲氧羰基,乙氧羰基,正-或异-丙氧羰基,甲基磺酰基,乙基磺酰基,正-或异-丙基磺酰基,
A12代表氢,氰基,氟,氯,溴或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,
A13代表氰基,氨基甲酰基,5,6-二氢-1,4,2-二噁嗪-3-基,氟,氯,溴,甲基,乙基,正-或异-丙基,乙酰基,丙酰基,正-或异-丁酰基,甲氧羰基,乙氧羰基,正-或异-丙氧羰基,
A14代表氢,代表氰基,氨基甲酰基,氟,氯,溴,甲基,乙基,正-或异-丙基,乙酰基,丙酰基,正-或异-丁酰基,甲氧羰基,乙氧羰基,正-或异-丙氧羰基,
A15代表氢,代表氰基,氨基甲酰基,氟,氯,溴,甲基,乙基,正-或异-丙基,乙酰基,丙酰基,正-或异-丁酰基,甲氧羰基,乙氧羰基,正-或异-丙氧羰基,或者与A14一起代表稠合的苯并基团,
A16代表氢,氰基,氟,氯,溴或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,甲基亚磺酰基,乙基亚磺酰基,正-或异-丙基亚磺酰基,甲基磺酰基,乙基磺酰基,正-或异-丙基磺酰基,
A17代表氢,氰基,氟,氯,溴或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,
A18代表氢,氰基,氟,氯,溴或者代表各自任选被氟或氯取代的甲基,乙基,正-或异-丙基,
A19代表氢,甲基,乙基,正-或异-丙基,
A20代表甲基,乙基,正-或异-丙基或者代表丙烯基或丁烯基,
A21代表氰基,氟,氯,溴,甲基,乙基,正-或异-丙基,或者代表三氟甲基,
A22代表甲基,乙基,正-或异-丙基,
A23代表甲基,乙基,正-或异-丙基,
A24其本身代表甲基,乙基,正-或异-丙基或者与A23一起代表乙烷-1,2-二基(二亚甲基)或丙烷-1,3-二基(三亚甲基),
A25代表氰基,氟,氯,溴,甲基,乙基,正-或异-丙基,或者代表三氟甲基,
A26代表甲基,乙基,正-或异-丙基,
A27代表氰基,氟,氯,溴,甲基,乙基,正-或异-丙基,或者代表三氟甲基,
A28代表氢,乙酰基,丙酰基,正-或异-丁酰基,甲氧羰基,乙氧羰基,正-或异-丙氧羰基,甲基磺酰基,乙基磺酰基,正-或异-丙基磺酰基,
A29代表氰基,氟,氯,溴,甲基,乙基,正-或异-丙基,或者代表三氟甲基,
A30代表氢,甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,
A31代表氢或者甲基,乙基,正-或异-丙基,
A32代表氰基,氟,氯,溴,甲基,乙基,正-或异-丙基,或者代表三氟甲基,
A33代表氢,甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,
A34代表氢,甲基,乙基,正-或异-丙基,
A35代表氰基,氟,氯,溴,甲基,乙基,正-或异-丙基,或者代表三氟甲基,
A36代表氢,甲基,乙基,正-或异-丙基,环丙基,环丁基,环戊基,环己基或苯基,
A37代表氢,甲基,乙基,正-或异-丙基,环丙基,环丁基,环戊基,环己基或苯基,
A38代表氢,氟,氯,溴,代表各自任选被氰基,氟,氯,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,甲硫基,乙硫基,正-或异-丙硫基,或者代表各自任选被氰基,氟,氯,甲基或乙基取代的环丙基,环丁基,环戊基,环己基,环丙基氧基,环丁基氧基,环戊基氧基,环己基氧基,环丙基甲基,环丁基甲基,环戊基甲基或环己基甲基,
A39代表氢,代表各自任选被氰基,氟,氯,甲氧基或乙氧基取代的甲基,乙基,正-或异-丙基,甲氧基,乙氧基,正-或异-丙氧基,或者代表各自任选被氰基,氟,氯,甲基或乙基取代的环丙基,环丁基,环戊基,环己基,环丙基氧基,环丁基氧基,环戊基氧基,环己基氧基,环丙基甲基,环丁基甲基,环戊基甲基或环己基甲基,以及式(Ⅰ)化合物的锂盐,钠盐,钾盐,镁盐,钙盐,铵盐,C1-C4-烷基-铵盐,二-(C1-C4-烷基)-铵盐,三-(C1-C4-烷基)-铵盐,四-(C1-C4-烷基)-铵盐,三-(C1-C4-烷基)-锍,C5-或C6-环烷基铵盐和二-(C1-C2-烷基)-苄基-铵盐。
4.处理植物的组合物,特征在于,它们含有至少一种权利要求1的式(Ⅰ)化合物或其盐。
5.权利要求1的通式(Ⅰ)化合物或其盐控制不期望植物,不期望微生物和/或动物害虫的用途。
6.控制杂草,不期望微生物和/或动物害虫的方法,其特征在于,使权利要求1的通式(Ⅰ)化合物或其盐作用于杂草,不期望微生物和/或动物害虫或其生长地域。
7.制备处理植物的组合物的方法,其特征在于,将权利要求1的通式(Ⅰ)化合物或其盐与扩充剂和/或表面活性剂混合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19629144A DE19629144A1 (de) | 1996-07-19 | 1996-07-19 | Substituierte Triazoloazinsulfonamide |
DE19629144.5 | 1996-07-19 |
Publications (1)
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CN1225638A true CN1225638A (zh) | 1999-08-11 |
Family
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CN97196536A Pending CN1225638A (zh) | 1996-07-19 | 1997-07-04 | 取代的三唑并吖嗪磺酰胺 |
Country Status (9)
Country | Link |
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US (1) | US6297195B1 (zh) |
EP (1) | EP0915878A2 (zh) |
JP (1) | JP2000515518A (zh) |
CN (1) | CN1225638A (zh) |
AU (1) | AU733250B2 (zh) |
BR (1) | BR9710385A (zh) |
CA (1) | CA2261136A1 (zh) |
DE (1) | DE19629144A1 (zh) |
WO (1) | WO1998003508A2 (zh) |
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CN103380115A (zh) * | 2010-12-16 | 2013-10-30 | 阿勒根公司 | 作为趋化因子受体调节剂的硫衍生物 |
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-
1996
- 1996-07-19 DE DE19629144A patent/DE19629144A1/de not_active Withdrawn
-
1997
- 1997-07-04 JP JP10506482A patent/JP2000515518A/ja active Pending
- 1997-07-04 US US09/214,773 patent/US6297195B1/en not_active Expired - Fee Related
- 1997-07-04 CA CA002261136A patent/CA2261136A1/en not_active Abandoned
- 1997-07-04 EP EP97932773A patent/EP0915878A2/de not_active Withdrawn
- 1997-07-04 WO PCT/EP1997/003535 patent/WO1998003508A2/de not_active Application Discontinuation
- 1997-07-04 AU AU36202/97A patent/AU733250B2/en not_active Ceased
- 1997-07-04 BR BR9710385A patent/BR9710385A/pt not_active Application Discontinuation
- 1997-07-04 CN CN97196536A patent/CN1225638A/zh active Pending
Cited By (7)
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CN103380115A (zh) * | 2010-12-16 | 2013-10-30 | 阿勒根公司 | 作为趋化因子受体调节剂的硫衍生物 |
US9328067B2 (en) | 2010-12-16 | 2016-05-03 | Allergan, Inc. | Sulfur derivatives as chemokine receptor modulators |
US9371278B2 (en) | 2010-12-16 | 2016-06-21 | Allergan, Inc. | Sulfur derivatives as chemokine receptor modulators |
CN103380115B (zh) * | 2010-12-16 | 2016-08-24 | 阿勒根公司 | 作为趋化因子受体调节剂的硫衍生物 |
US9663460B2 (en) | 2010-12-16 | 2017-05-30 | Allergan, Inc. | Sulfur derivatives as chemokine receptor modulators |
US10287243B2 (en) | 2010-12-16 | 2019-05-14 | Allergan, Inc. | Sulfur derivatives as chemokine receptor modulators |
US11046644B2 (en) | 2010-12-16 | 2021-06-29 | Allergan, Inc. | Sulfur derivatives as chemokine receptor modulators |
Also Published As
Publication number | Publication date |
---|---|
AU3620297A (en) | 1998-02-10 |
US6297195B1 (en) | 2001-10-02 |
CA2261136A1 (en) | 1998-01-29 |
WO1998003508A2 (de) | 1998-01-29 |
DE19629144A1 (de) | 1998-01-22 |
EP0915878A2 (de) | 1999-05-19 |
JP2000515518A (ja) | 2000-11-21 |
AU733250B2 (en) | 2001-05-10 |
BR9710385A (pt) | 1999-08-17 |
WO1998003508A3 (de) | 1998-05-22 |
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