CN1218469A - 用作除草剂的取代的噻吩基磺酰基(硫代)脲 - Google Patents
用作除草剂的取代的噻吩基磺酰基(硫代)脲 Download PDFInfo
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- CN1218469A CN1218469A CN97194465A CN97194465A CN1218469A CN 1218469 A CN1218469 A CN 1218469A CN 97194465 A CN97194465 A CN 97194465A CN 97194465 A CN97194465 A CN 97194465A CN 1218469 A CN1218469 A CN 1218469A
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- methyl
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- halogen
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- -1 thienyl sulphonyl (thio) ureas Chemical class 0.000 title claims abstract description 98
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
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Abstract
本发明涉及新的取代的噻吩基磺酰基(硫代)脲类,其中A代表氮原子或CH基团,Q代表氧原子或硫原子,R1代表氢原子,卤原子或者各自任选被取代的烷基,烷氧基,烷硫基,烷基氨基,二烷基氨基,环烷基,环烷基氧基,芳基氧基或杂环基氧基,R2代表氢原子,卤原子或者各自任选被取代的烷基,烷氧基,烷硫基,烷基氨基,二烷基氨基,环烷基,环烷基氧基,芳基氧基或杂环基氧基,R3代表氢原子或者任选被取代的烷基,R4代表各自任选被取代的烷基,和R5代表氢原子,或者各自任选被取代的烷基,链烯基,炔烃基,环烷基,环烷基烷基,或杂环基,以及式(Ⅰ)化合物的盐,但从这些物质中排除一些现有技术化合物。本发明还涉及制备这些新的化合物的方法,以及涉及其作为除草剂的用途。
Description
本发明涉及新的取代的噻吩基磺酰基(硫代)脲，涉及其制备方法，以及涉及其作为除草剂的用途。
已知一些取代的噻吩基磺酰基脲，例如化合物N-(4-环丙基-6-甲氧基-1,3,5-三嗪-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，具有除草性能(参见EP207609，也参见EP30142)。但是这些已知的化合物的除草活性不是在所有方面都令人满意。
因此，本发明提供新的通式(Ⅰ)的取代的噻吩基磺酰基(硫代)脲
(Ⅰ)
其中
A代表氮原子或CH基团，
Q代表氧或硫，
R1代表氢，卤素或各自任选被取代的烷基，烷氧基，烷硫基，烷基氨基，二烷基氨基，环烷基，环烷基氧基，芳基氧基或杂环基氧基，
R2代表氢，卤素或各自任选被取代的烷基，烷氧基，烷硫基，烷基氨基，二烷基氨基，环烷基，环烷基氧基，芳基氧基或杂环基氧基，
R3代表氢或任选被取代的烷基，
R4代表任选被取代的烷基，和
R5代表氢，或各自任选被取代的烷基，链烯基，炔烃基，环烷基，环烷基烷基或杂环基，
以及式(Ⅰ)化合物的盐，
除了先有技术化合物N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-[2-(2-氯-乙氧基羰基)-4-甲基-噻吩-3-基-磺酰基]-脲，N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(4-乙基-2-异丙氧基羰基-噻吩-3-基-磺酰基)-脲，N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(2-烯丙基氧基羰基-4-正丁基-噻吩-3-基-磺酰基)-脲，N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-异丙基-噻吩-3-基-磺酰基)-脲，和N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-三氟甲基-噻吩-3-基-磺酰基)-脲(参见EP30142)，同样还有先有技术化合物N-(4-环丙基-6-甲氧基-嘧啶-2-基)-N’-(4-甲基-2-正丙氧基羰基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲氧基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲氧基-1,3,5-三嗪-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲基-1,3,5-三嗪-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，和N-(4-环丙基-6-甲氧基-1,3,5-三嗪-2-基)-N’-(2-异丙氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲(参见EP207609)，这些化合物被排除在权利要求之外。
当进行下面的反应时得到新的通式(Ⅰ)的取代的噻吩基磺酰基(硫代)脲：
(a)如果适当在反应助剂存在下和如果适当在稀释剂存在下，通式(Ⅱ)的氨基吖嗪与通式(Ⅲ)的异(硫代)氰酸噻吩基磺酰酯反应，(Ⅱ)其中A,R1和R2各自如上定义，
(Ⅲ)
其中
Q,R4和R5各自如上定义，
或者
(b)如果适当在反应助剂存在下和如果适当在稀释剂存在下，通式(Ⅳ)的取代的氨基吖嗪与通式(Ⅴ)的噻吩磺酰胺反应，(Ⅳ)其中A,Q,R1和R2各自如上定义，Z代表卤素，烷氧基或芳基氧基，和R具有上文对于R3的定义，或者代表基团-C(Q)-Z,(Ⅴ)
其中
R4和R5各自如上定义，
或者
(c)如果适当在反应助剂存在下和如果适当在稀释剂存在下，通式(Ⅱ)的氨基吖嗪与通式(Ⅵ)的取代的噻吩磺酰胺反应，
(Ⅱ)其中A,R1和R2各自如上定义，
(Ⅵ)
其中
Q,R4和R5各自如上定义，
Z代表卤素，烷氧基或芳基氧基，
并且通过方法(a),(b)和(c)得到的式(Ⅰ)化合物可以任选通过常规方法转化为盐。
新的通式(Ⅰ)的取代的噻吩基磺酰基(硫代)脲具有强的除草活性。
本发明优选提供下列式(Ⅰ)化合物，
其中
A代表氮原子或CH基团，
Q代表氧或硫，
R1代表氢，卤素或各自任选被氰基-，卤素-或C1-C4-烷氧基-取代的、各种情况下在烷基中具有1-4个碳原子的烷基，烷氧基，烷硫基，烷基氨基或二烷基氨基，代表各自任选被氰基-，卤素-，C1-C4-烷基-或C1-C4-烷氧基-取代的、各种情况下具有3-6个碳原子的环烷基或环烷基氧基，或者代表各自任选被氰基-，卤素-,C1-C4-烷基-或C1-C4-烷氧基-取代的苯氧基，噁丁环基氧基，呋喃基氧基，或四氢呋喃基氧基，
R2代表氢或卤素，代表各自任选被氰基-，卤素-或C1-C4-烷氧基-取代的、各种情况下在烷基中具有1-4个碳原子的烷基，烷氧基，烷硫基，烷基氨基或二烷基氨基，代表各自任选被氰基-，卤素-,C1-C4-烷基-或C1-C4-烷氧基-取代的、各种情况下具有3-6个碳原子的环烷基或环烷基氧基，或者代表各自任选被氰基-，卤素-,C1-C4-烷基-或C1-C4-烷氧基-取代的苯氧基，噁丁环基氧基，呋喃基氧基或四氢呋喃基氧基，
R3代表氢或任选被C1-C4-烷氧基-,C1-C4-烷基-羰基-或C1-C4-烷氧基-羰基-取代的具有1-4个碳原子的烷基，
R4代表任选被氰基-，卤素-或C1-C4-烷氧基-取代的具有1-6个碳原子的烷基，和
R5代表氢，代表各自任选被氰基-，卤素-或C1-C4-烷氧基-取代的具有1-6个碳原子的烷基，代表各自任选被卤素取代的在各种情况下具有2-6个碳原子的链烯基或炔烃基，代表各自任选被氰基-，卤素-或C1-C4-烷基-取代的各种情况下在环烷基部分具有3-6个碳原子并且任选地在烷基部分具有1-4个碳原子的的环烷基或环烷基烷基，或代表各自任选被氰基-，卤素-,C1-C4-烷基-或C1-C4-烷氧基-取代的噁丁环基，呋喃基或四氢呋喃基，
除了先有技术化合物N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-[2-(2-氯-乙氧基羰基)-4-甲基-噻吩-3-基-磺酰基]-脲，N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(4-乙基-2-异丙氧基羰基-噻吩-3-基-磺酰基)-脲，N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(2-烯丙基氧基羰基-4-正丁基-噻吩-3-基-磺酰基)-脲，N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-异丙基-噻吩-3-基-磺酰基)-脲和N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-三氟甲基-噻吩-3-基-磺酰基)-脲(参见EP30142)，同样还有先有技术化合物N-(4-环丙基-6-甲氧基-嘧啶-2-基)-N’-(4-甲基-2-正丙氧基羰基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲氧基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲氧基-1,3,5-三嗪-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲基-1,3,5-三嗪-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲和N-(4-环丙基-6-甲氧基-1,3,5-三嗪-2-基)-N’-(2-异丙氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲(参见EP207609)，这些化合物被排除在权利要求范围外。
本发明还优选提供其中A,Q,R1,R2,R3,R4和R5各自优选如上文定义的式(Ⅰ)化合物的钠盐，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。
本发明特别提供下列式(Ⅰ)化合物，
其中
A代表氮原子或CH基团，
Q代表氧或硫，
R1代表氢，氟，氯，溴，或者各自任选被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基或异丙基，甲氧基，乙氧基，正丙氧基，异丙氧基，甲基硫基，乙基硫基，正-或异-丙基硫基，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代表氟，氯，溴，或者各自任选被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基，异丙基，甲氧基，乙氧基，正丙氧基，异丙氧基，甲基硫基，乙基硫基，正-或异-丙基硫基，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，
R3代表氢或任选被甲氧基-，乙氧基-，正-或异-丙氧基-，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-取代的甲基或乙基，
R4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，正丙基，异丙基，正-，异-，仲-或叔-丁基，和
R5代表氢，代表各自任选被氰基-，氟-，氯-，甲氧基-，乙氧基-，正-或异-丙氧基取代的甲基，乙基，正丙基，异丙基，正-，异-，仲-或叔-丁基，代表各自任选被氟-，氯-或溴-取代的丙烯基，丁烯基，丙炔基或丁炔基，或者代表各自任选被氰基-，氟-，氯-，溴-，甲基-，乙基-，正丙基-或异丙基-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，
除了先有技术化合物N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-[2-(2-氯-乙氧基羰基)-4-甲基-噻吩-3-基-磺酰基]-脲，N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(4-乙基-2-异丙氧基羰基-噻吩-3-基-磺酰基)-脲，N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(2-烯丙基氧基羰基-4-正丁基-噻吩-3-基-磺酰基)-脲，N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-异丙基-噻吩-3-基-磺酰基)-脲和N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-三氟甲基-噻吩-3-基-磺酰基)-脲(参见EP30142)，还有同样是先有技术化合物N-(4-环丙基-6-甲氧基-嘧啶-2-基)-N’-(4-甲基-2-正丙氧基羰基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲氧基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲氧基-1,3,5-三嗪-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲基-1,3,5-三嗪-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲和N-(4-环丙基-6-甲氧基1,3,5-三嗪-2-基)-N’-(2-异丙氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲(参见EP207609)，这些化合物被排除在权利要求之外。
上述一般或优选基团定义适用于式(Ⅰ)终产物，并相应地适用于每种情况下用于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，也就是说所声明范围内的优选化合物之间的组合也是可能的。
本发明的式(Ⅰ)化合物的实施例在下面的组中列出。第1组
(1A-1)A,Q,R1,R2和R3具有例如下面的意义：
第2组
(1A-2)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第3组(1A-3)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第4组
(1A-4)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第5组(1A-5)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第6组(1A-8)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第7组
(1A-7)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第8组(1A-8)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第9组
(1A-9)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第10组
(1A-10)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第11组
(1A-11)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第12组(1A-12)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第13组
(1A-13)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第14组
(1A-14)A,Q,R1,R2和R3具有例如上面第1组中给出的意义。第15组
(1A-15)
A,Q,R1,R2和R3具有例如上面第1组中给出的意义。
使用例如2-氨基-4-甲氧基-6-甲基-嘧啶和异氰酸2-乙氧羰基-4-三氟甲基-噻吩-3-基-磺酰基酯为起始物，则本发明方法(a)的反应过程可通过下面的反应式说明：使用例如2-甲氧基羰基氨基-4-甲氧基-6-三氟甲基-1,3,5-三嗪和4-乙基-2-异丙氧基羰基-噻吩-3-磺酰胺为起始物，则本发明方法(b)的反应过程可通过下面的反应式说明：
使用例如2-氨基-4-氯-6-甲氧基-嘧啶和N-(2-乙氧基羰基-4-甲基-噻吩-3-基-磺酰基)-O-苯基-氨基甲酸乙酯为起始物，则本发明方法(c)的反应过程可通过下面的反应式说明：
式(Ⅱ)提供了在制备通式(Ⅰ)化合物的本发明方法(a)和(c)中用作起始物的氨基吖嗪的一般定义。在式(Ⅱ)中，A,R1和R2各自优选或特别具有上文已经指明的与描述式(Ⅰ)化合物相关的作为A,R1和R2优选的或特别优选的定义的那些定义。
式(Ⅱ)的氨基吖嗪是已知的用于合成的化学品，其中一些是商售的。
式(Ⅲ)提供了本发明方法(a)中也用作起始物的异(硫代)氰酸噻吩基磺酰基酯的一般定义。在式(Ⅲ)中，Q,R4和R5各自优选或特别具有上文已经指明的与描述式(Ⅰ)化合物相关的作为Q,R4和R5优选的或特别优选的定义的那些定义。
式(Ⅲ)的起始物是已知的和/或能通过本身已知的方法制备(参见EP30142)。
在80℃-150℃之间的温度下，如果适当在异氰酸烷基酯例如异氰酸丁酯存在下，如果适当在反应助剂，例如二氮杂双环[2.2.2]辛烷存在下，和在稀释剂例如甲苯，二甲苯或氯苯存在下，上述通式(Ⅴ)噻吩磺酰胺与光气或硫光气反应，反应完全后减压蒸掉挥发成分，得到了式(Ⅲ)的异(硫代)氰酸噻吩基磺酰基酯。
式(Ⅳ)提供了在制备通式(Ⅰ)化合物的本发明方法(b)中用作起始物的取代的氨基吖嗪的一般定义。在式(Ⅳ)中，A,Q,R1,R2和R各自优选或特别具有上文已经指明的，与描述式(Ⅰ)化合物相关的，作为A,Q,R1,R2或R3优选的或特别优选的定义的那些定义，其中R也可以代表-C(Q)-Z；Z优选代表氟，氯，溴，C1-C4-烷氧基或苯氧基，特别是氯，甲氧基，乙氧基或苯氧基。
式(Ⅳ)起始物是已知的和/或能通过本身已知的方法制备(参见US4690707,DE19501174，制备实施例)。
式(Ⅴ)提供了本发明方法(b)中也用作起始物的噻吩氨磺酰的一般定义。在式(Ⅴ)中，R4和R5各自优选或特别具有上文已经指明的，与描述式(Ⅰ)化合物相关的，作为R4和R5优选的或特别优选的定义的那些定义。
式(Ⅴ)起始物是已知的和/或能通过本身已知的方法制备(参见EP30142)。
式(Ⅵ)提供了在制备通式(Ⅰ)化合物的本发明方法(c)中用作起始物的取代的噻吩氨磺酰的一般定义。在式(Ⅵ)中，Q,R4和R5各自优选或特别具有上文已经指明的，与描述式(Ⅰ)化合物相关的，作为Q,R4和R5优选的或特别优选的定义的那些定义；Z优选代表氟，氯，溴，C1-C4-烷氧基或苯氧基，特别是氯，甲氧基，乙氧基或苯氧基。
式(Ⅵ)起始物是已知的和/或能通过本身已知的方法制备。
进行本发明方法(a),(b)和(c)的合适的稀释剂是惰性有机溶剂。特别包括脂肪族，脂环族或芳香族的，任选卤化的烃，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，丙腈或苄腈；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酰三胺；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。
本发明方法(a),(b)和(c)优选在合适的反应助剂存在下进行，合适的反应助剂是所有的常规无机碱或有机碱。包括例如碱土金属或碱金属氢化物，氢氧化物，氨化物，烷氧化物，乙酸盐，碳酸盐或碳酸氢盐，例如氢化钠，氨化钠，甲醇钠，乙醇钠，叔丁醇钾，氢氧化钠，氢氧化钾，氢氧化铵，乙酸钠，乙酸钾，乙酸钙，乙酸铵，碳酸钠，碳酸钾，碳酸氢钾，碳酸氢钠或碳酸铵，以及叔胺类，例如三甲胺，三乙胺，三丁基胺，N,N,-二甲基苯胺，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)或二氮杂双环十一烯(DBU)。
进行本发明方法(a),(b)和(c)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-20℃和+150℃之间的温度下进行，优选在0℃和+120℃的温度下进行。
本发明方法(a),(b)和(c)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。
在实施本发明方法(a),(b)和(c)时，一般以大约等摩尔量使用起始物。但是，也可以以较大的过量使用其中之一起始物组分。反应一般在合适的反应助剂的存在下在合适的溶剂中进行，并且反应混合物一般在需要的温度下搅拌数小时。通过常规方法进行后处理(参见制备实施例)。
如果需要，可制备本发明通式(Ⅰ)化合物的盐。通过形成盐的常规方法以简单的方式获得这样的盐，例如通过将式(Ⅰ)化合物溶解于或分散于合适的溶剂例如二氯甲烷，丙酮，叔丁基甲基醚或甲苯中，并加入合适的碱。然后-如果需要，经延长时间的搅拌后-通过浓缩或吸滤分离盐。
本发明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。本发明物质是作为完全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)，凤梨属(Ananas)，天门冬属(Asparagus)和葱属(Allium)。
但是本发明活性化合物的用途绝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，以及用来在年生种植植物场所选择性控制杂草。
本发明式(Ⅰ)化合物特别适用于在芽前和芽后控制单子叶和双子叶杂草，当对土壤和植物地上部分施用时，它们具有强的除草活性和广谱活性。
活性化合物可以配制成常规制剂，例如溶液、乳剂、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、和浸有活性化合物的天然和合成材料以及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，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：芳族化合物，如二甲苯，甲苯或烷基萘，氯代芳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，例如石油馏份，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，如二甲基甲酰胺或二甲亚砜，以及还有水。
合适的固体载体是：例如铵盐，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，如研细的二氧化硅、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：锯木屑、椰壳、玉米穗轴和烟茎；适合的乳化剂和/或起泡剂有：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；适合的分散剂有：例如，木素亚硫酸废液和甲基纤维素。
制剂中，可以使用增粘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。可能的其它的添加剂是矿物油和植物油。
也可能使用着色剂，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％。
对于防治杂草，本发明活性化合物本身或其制剂形式也可以作为与已知除草剂的混合物使用，可以是最终制剂或容器混合物。
用于所述混合物的可能组分是已知的除草剂，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。
也可能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，以制剂形式使用，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。它们也可以在播种前直接被掺合到土壤中。
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，使用的量在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。
从下面的实施例可以明了本发明活性化合物的制备和应用。
制备实施例
实施例1
(方法(a))
首先将1.24g(10mmol)2-氨基-4,6-二甲基-1,3,5-三嗪加入到40ml乙腈中，在室温下(大约20℃)加入2.61g(10mmol)异氰酸2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰酯。混合物在回流下加热12小时，然后吸滤分离得到的结晶产物。
得到2.6g(理论量的68％)N-(4,6-二甲基-1,3,5-三嗪-2-基)-N’-(2-甲氧羰基-4-甲基-噻吩-3-基磺酰基)-脲，熔点210℃。
实施例2
(方法(b))
首先将1.30g(3.9mmol)N,N-双-苯氧羰基-2-氨基-4-甲氧基-6-甲基-1,3,5-三嗪加入到50ml乙腈中。然后在室温下(大约20℃)加入1.13g(4.3mmol)4-甲基-2-异丙氧羰基-噻吩-3-氨磺酰和0.65g(4.3mmol)二氮杂双环十一烯(DBU)，混合物在该温度下搅拌大约12小时。然后混合物用水泵抽真空浓缩，残余物用2N盐酸酸化，并用二氯甲烷萃取。有机相用水洗涤，硫酸镁干燥并过滤。用水泵抽真空浓缩滤液，残余物溶解于乙醚，并吸滤分离得到的结晶产物。
得到0.87g(理论量的52％)N-(4-甲氧基-6-甲基-1,3,5-三嗪-2-基)-N’-(4-甲基-2-异丙氧羰基-噻吩-3-基磺酰基)-脲，熔点185℃。
实施例3
(方法(b))
首先将1.24g(5.1mmol)N-苯氧羰基-2-氨基-4,6-二甲基-嘧啶加入到50ml乙腈中。然后在室温下(大约20℃)加入1.47g(5.6mmol)4-甲基-2-异丙氧羰基-噻吩-3-氨磺酰和0.85g(5.6mmol)二氮杂双环十一烯(DBU)，混合物在该温度下搅拌大约12小时。然后混合物用水泵抽真空浓缩，残余物用2N盐酸酸化，并用二氯甲烷萃取。有机相用水洗涤，硫酸镁干燥并过滤。用水泵抽真空浓缩滤液，残余物溶解于乙醚，并吸滤分离得到的结晶产物。
得到1.29g(理论量的56％)N-(4,6-二甲基-嘧啶-2-基)-N’-(4-甲基-2-异丙氧羰基-噻吩-3-基-磺酰基)-脲，熔点223℃。
类似于制备实施例1-3，并根据本发明制备方法的一般性说明，也能制备例如下面表1中列出的式(Ⅰ)化合物。
(Ⅰ)表1：式(Ⅰ)化合物的实施例 
应用实施例在应用实施例中使用下面的化合物作为对比物质：(A)
N-(4-环丙基-6-甲氧基-1,3,5-三嗪-2-基)-N’-(2-甲氧羰基-4-甲基-噻吩-3-基-磺酰基)-脲(EP207609中公开)。
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，用活性化合物制剂对土壤浇灌。有益的是，每单位面积用的水的量保持不变。制剂中活性化合物的浓度并不重要，只有每单位面积施用的活性化合物的比例是重要的。
三星期后，以与未处理对照物生长相比较的杀伤百分率测定对植物的杀伤程度。
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1,2,3,4,5,11,14,16,18,20,25,26,27,28,33,37,38,39和41的化合物在以每公顷30g-125g活性成分之间的比例施用时，显示出比已知化合物(A)强得多的除草活性。参见表A-1至A-6。
实施例A的表：芽前试验/温室表A-1：活性化合 施用比例 看麦娘 野燕麦 莎草 狗尾草 苘麻 苋属 猪殃殃物的制备 (g活性实施例编 成分/公号顷)(A) 125 80 30 90 80 80 80 80(13) 60 95 90 95 90 95 95 95(1) 60 95 90 95 95 95 95 95(4) 60 95 90 95 95 95 95 100(14) 60 95 90 95 95 95 95 90(33) 60 100 95 100 100 100 - 100(3) 60 100 90 100 100 - 100 95(39) 60 100 95 100 100 100 100 100(37) 60 100 - 90 90 100 100 100(18) 60 90 70 100 - 100 95 100(20) 60 100 100 100 80 95 100 100(25) 30 100 - 100 95 100 100 100表A-2：活性化合 施用比例 看麦娘 野燕麦 莎草 狗尾草 苘麻 苋属物的制备 (g活性成实施例编 分/公顷)号(A) 125 80 30 90 80 80 80(16) 60 90 70 95 80 90 95(11) 60 95 50 - 95 100 95(2) 60 100 95 95 90 100 95(19) 30 100 90 100 100 100 100表A-3：活性化合 施用比例 看麦娘 野燕麦 莎草 苋属 猪殃殃物的制备 (g活性成实施例编 分/公顷)号(A) 125 80 30 90 80 80(27) 30 100 90 100 95 90表A-4：活性化合 施用比例 看麦娘 莎草 苘麻 苋属 猪殃殃物的制备 (g活性成实施例编 分/公顷)号(A) 125 80 90 80 80 80(5) 125 100 95 95 95 95(28) 60 100 100 100 100 95(26) 30 100 100 100 100 100表A-5：活性化合 施用比例 看麦娘 莎草 猪殃殃物的制备 (g活性成实施例编 分/公顷)号(A) 125 80 90 80(41) 60 100 100 100表A-6：活性化合 施用比例 看麦娘 苘麻 苋属 猪殃殃物的制备 (g活性成实施例编 分/公顷)号(A) 125 80 80 80 80(38) 60 100 95 90 100
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，以对每单位面积施用一定量的期望的活性化合物。选择喷雾液的浓度，使在每种情况下以1000L水/公顷施用期望的活性化合物的量。
三星期后，以与未处理对照物生长相比较的杀伤百分率测定对植物的杀伤程度。
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11,13,14,19,20,25,27和39的化合物在以每公顷8g-60g之间的比例施用时，显示出比已知化合物(A)强得多的除草活性；参见表B-1和B-2。
实施例B的表：芽后试验/温室表B-1：活性化合 施用比例 雀麦 莎草 马唐 稗 黑麦草 蜀黍 藜属 婆婆纳物的制备 (g活性成实施例编 分/公顷)号(A) 60 10 0 0 60 30 20 - 30(11) 60 60 70 80 90 90 95 - 100(20) 60 60 70 - - 70 90 90 80表B-2：活性化合 施用比例 雀麦 莎草 马唐 稗 黑麦草 蜀黍 藜属 猪殃殃 蓼属 婆婆纳物的制备 (g活性成实施例编 分/公顷)号(A) 30 0 0 0 20 20 10 40 70 80 10(13) 30 90 60 80 95 95 80 90 - 90 70(14) 15 80 70 60 70 60 70 80 80 - 90(27) 30 60 90 60 95 - 90 90 100 95 50
Claims (8)
1．通式(Ⅰ)取代的噻吩基磺酰基(硫代)脲
(Ⅰ)
其中
A代表氮原子或CH基团，
Q代表氧或硫，
R1代表氢，卤素或各自任选被取代的烷基，烷氧基，烷硫基，烷基氨基，二烷基氨基，环烷基，环烷基氧基，芳基氧基或杂环基氧基，
R2代表氢，卤素或各自任选被取代的烷基，烷氧基，烷硫基，烷基氨基，二烷基氨基，环烷基，环烷基氧基，芳基氧基或杂环基氧基，
R3代表氢或任选被取代的烷基，
R4代表任选被取代的烷基，和
R5代表氢，或各自任选被取代的烷基，链烯基，炔烃基，环烷基，环烷基烷基或杂环基，
以及式(Ⅰ)化合物的盐，
除了化合物N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-[2-(2-氯-乙氧基羰基)-4-甲基-噻吩-3-基-磺酰基]-脲，N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(4-乙基-2-异丙氧基羰基-噻吩-3-基-磺酰基)-脲，N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(2-烯丙基氧基羰基-4-正丁基-噻吩-3-基-磺酰基)-脲，N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-异丙基-噻吩-3-基-磺酰基)-脲，和N-(4-甲氧基-6-甲基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-三氟甲基-噻吩-3-基-磺酰基)-脲，还有化合物N-(4-环丙基-6-甲氧基-嘧啶-2-基)-N’-(4-甲基-2-正丙氧基羰基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲氧基-嘧啶-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲氧基-1,3,5-三嗪-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，N-(4-环丙基-6-甲基-1,3,5-三嗪-2-基)-N’-(2-甲氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲，和N-(4-环丙基-6-甲氧基-1,3,5-三嗪-2-基)-N’-(2-异丙氧基羰基-4-甲基-噻吩-3-基-磺酰基)-脲。
2．权利要求1的式(Ⅰ)化合物，特征在于
A代表氮原子或CH基团，
Q代表氧或硫，
R1代表氢，卤素或各自任选被氰基-，卤素-或C1-C4-烷氧基-取代的、各种情况下在烷基中具有1-4个碳原子的烷基，烷氧基，烷硫基，烷基氨基或二烷基氨基，代表各自任选被氰基-，卤素-，C1-C4-烷基-或C1-C4-烷氧基-取代的、各种情况下具有3-6个碳原子的环烷基或环烷基氧基，或者代表各自任选被氰基-，卤素-，C1-C4-烷基-或C1-C4-烷氧基-取代的苯氧基，噁丁环基氧基，呋喃基氧基，或四氢呋喃基氧基，
R2代表氢或卤素，代表各自任选被氰基-，卤素-或C1-C4-烷氧基-取代的、各种情况下在烷基中具有1-4个碳原子的烷基，烷氧基，烷硫基，烷基氨基或二烷基氨基，代表各自任选被氰基-，卤素-，C1-C4-烷基-或C1-C4-烷氧基-取代的、各种情况下具有3-6个碳原子的环烷基或环烷基氧基，或者代表各自任选被氰基-，卤素-，C1-C4-烷基-或C1-C4-烷氧基-取代的苯氧基，噁丁环基氧基，呋喃基氧基或四氢呋喃基氧基，
R3代表氢或任选被C1-C4-烷氧基-,C1-C4-烷基-羰基-或C1-C4-烷氧基-羰基-取代的具有1-4个碳原子的烷基，
R4代表任选被氰基-，卤素-或C1-C4-烷氧基-取代的具有1-6个碳原子的烷基，和
R5代表氢，代表任选被氰基-，卤素-或C1-C4-烷氧基-取代的具有1-6个碳原子的烷基，代表各自任选被卤素取代的在各种情况下具有2-6个碳原子的链烯基或炔烃基，代表各自任选被氰基-，卤素-或C1-C4-烷基-取代的在各种情况下在环烷基部分具有3-6个碳原子并且任选地在烷基部分具有1-4个碳原子的的环烷基或环烷基烷基，或代表各自任选被氰基-，卤素-,C1-C4-烷基-或C1-C4-烷氧基-取代的噁丁环基，呋喃基，或四氢呋喃基，
和式(Ⅰ)化合物的钠盐，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，
和权利要求1一样排除相同的化合物。
3．权利要求1的式(Ⅰ)化合物，特征在于
A代表氮原子或CH基团，
Q代表氧或硫，
R1代表氢，氟，氯，溴，或者各自任选被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基，异丙基，甲氧基，乙氧基，正丙氧基，异丙氧基，甲基硫基，乙基硫基，正-或异-丙基硫基，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代表氟，氯，溴或者各自任选被氰基-，氟-，氯-，甲氧基-或乙氧基-取代的甲基，乙基，正丙基，异丙基，甲氧基，乙氧基，正丙氧基，异丙氧基，甲基硫基，乙基硫基，正-或异-丙基硫基，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，
R3代表氢或任选被甲氧基-，乙氧基-，正-或异-丙氧基-，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-取代的甲基或乙基，
R4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，正丙基，异丙基，正-，异-，仲-或叔-丁基，和
R5代表氢，代表各自任选被氰基-，氟-，氯-，甲氧基-，乙氧基-，正-或异-丙氧基取代的甲基，乙基，正丙基，异丙基，正-，异-，仲-或叔-丁基，代表各自任选被氟-，氯-或溴-取代的丙烯基，丁烯基，丙炔基或丁炔基，或者代表各自任选被氰基-，氟-，氯-，溴-，甲基-，乙基-，正丙基-或异丙基-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，
和权利要求1一样排除相同的化合物。
4．制备权利要求1的式(Ⅰ)化合物的方法，特征在于
(a)如果适当在反应助剂存在下和如果适当在稀释剂存在下，通式(Ⅱ)的氨基吖嗪与通式(Ⅲ)的异(硫代)氰酸噻吩基磺酰酯反应，
(Ⅱ)其中A,R1和R2各自如权利要求1所定义，
(Ⅲ)
其中
Q,R4和R5各自如权利要求1所定义，
或者
(b)如果适当在反应助剂存在下和如果适当在稀释剂存在下，通式(Ⅳ)的取代的氨基吖嗪与通式(Ⅴ)的噻吩氨磺酰反应，
(Ⅳ)其中A,Q,R1和R2各自如权利要求1所定义，Z代表卤素，烷氧基或芳基氧基，和R具有上文对于R3的定义，或者代表基团-C(Q)-Z，
(Ⅴ)
其中
R4和R5各自如上定义，
或者
(c)如果适当在反应助剂存在下和如果适当在稀释剂存在下，通式(Ⅱ)的氨基吖嗪与通式(Ⅵ)的取代的噻吩氨磺酰反应，
(Ⅱ)其中A,R1和R2各自如权利要求1所定义，(Ⅵ)
其中
Q,R4和R5各自如上定义，
Z代表卤素，烷氧基或芳基氧基，
并且任选地将由方法(a),(b)和(c)得到的式(Ⅰ)化合物通过常规方法转化为盐。
5．除草组合物，特征在于其含有至少一种权利要求1的式(Ⅰ)化合物。
6．权利要求1的通式(Ⅰ)化合物控制不期望植物生长的用途。
7．防治杂草的方法，特征在于使权利要求1的通式(Ⅰ)化合物作用于杂草或其生长地域。
8．制备除草组合物的方法，特征在于将权利要求1的通式(Ⅰ)化合物与扩充剂和/或表面活性剂混合。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19608831.3 | 1996-03-07 | ||
| DE19608831A DE19608831A1 (de) | 1996-03-07 | 1996-03-07 | Substituierte Thienylsulfonyl(thio)harnstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1218469A true CN1218469A (zh) | 1999-06-02 |
Family
ID=7787505
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97194465A Pending CN1218469A (zh) | 1996-03-07 | 1997-02-24 | 用作除草剂的取代的噻吩基磺酰基(硫代)脲 |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0885216A1 (zh) |
| JP (1) | JP2000506146A (zh) |
| KR (1) | KR19990087494A (zh) |
| CN (1) | CN1218469A (zh) |
| AU (1) | AU717425B2 (zh) |
| BR (1) | BR9708009A (zh) |
| CA (1) | CA2248290A1 (zh) |
| DE (1) | DE19608831A1 (zh) |
| WO (1) | WO1997032875A1 (zh) |
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| DE19963383A1 (de) | 1999-12-28 | 2001-07-05 | Aventis Cropscience Gmbh | Formulierung von Herbiziden und Pflanzenwachstumsregulatoren |
| AU763467B2 (en) * | 1999-01-27 | 2003-07-24 | Bayer Cropscience Ag | Formulation of herbicides and plant growth regulators |
| DE19937118A1 (de) | 1999-08-06 | 2001-02-08 | Bayer Ag | Substituierte Thienyl(amino)sulfonylharnstoffe |
| AR122450A1 (es) | 2020-05-08 | 2022-09-14 | Lilly Co Eli | Compuestos de (trifluorometil)pirimidin-2-amina |
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| DK172396B1 (da) * | 1979-11-30 | 1998-05-18 | Du Pont | Thiophencarboxylsyrederivater, middel til bekæmpelse af væksten af uønsket vegetation, fremgangsmåde til bekæmpelse af uønsket vegetation samt mellemprodukter til fremstilling af de nævnte derivater |
| CA1257262A (en) * | 1985-05-20 | 1989-07-11 | George Levitt | Herbicidal thiophenesulfonamides |
| US4877440A (en) * | 1985-05-29 | 1989-10-31 | E. I. Du Pont De Nemours And Company | Thiophenesulfonamide herbicides |
-
1996
- 1996-03-07 DE DE19608831A patent/DE19608831A1/de not_active Withdrawn
-
1997
- 1997-02-24 CA CA002248290A patent/CA2248290A1/en not_active Abandoned
- 1997-02-24 EP EP97906118A patent/EP0885216A1/de not_active Withdrawn
- 1997-02-24 BR BR9708009A patent/BR9708009A/pt unknown
- 1997-02-24 WO PCT/EP1997/000877 patent/WO1997032875A1/de not_active Application Discontinuation
- 1997-02-24 JP JP9531404A patent/JP2000506146A/ja active Pending
- 1997-02-24 CN CN97194465A patent/CN1218469A/zh active Pending
- 1997-02-24 AU AU20927/97A patent/AU717425B2/en not_active Ceased
- 1997-02-24 KR KR1019980706922A patent/KR19990087494A/ko not_active Application Discontinuation
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| Publication number | Publication date |
|---|---|
| JP2000506146A (ja) | 2000-05-23 |
| CA2248290A1 (en) | 1997-09-12 |
| EP0885216A1 (de) | 1998-12-23 |
| BR9708009A (pt) | 1999-07-27 |
| DE19608831A1 (de) | 1997-09-18 |
| KR19990087494A (ko) | 1999-12-27 |
| AU2092797A (en) | 1997-09-22 |
| AU717425B2 (en) | 2000-03-23 |
| WO1997032875A1 (de) | 1997-09-12 |
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