CN1278804A - 异噻唑羧酸衍生物 - Google Patents
异噻唑羧酸衍生物 Download PDFInfo
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- CN1278804A CN1278804A CN98811083.0A CN98811083A CN1278804A CN 1278804 A CN1278804 A CN 1278804A CN 98811083 A CN98811083 A CN 98811083A CN 1278804 A CN1278804 A CN 1278804A
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Abstract
本发明涉及新颖的式(Ⅰ)的异噻唑羧酸衍生物,其中R具有说明书中给出的含义,本发明还涉及制备此新颖物质的方法及其保护植物不受有害微生物和动物害虫侵害的方法。
Description
本发明涉及新颖的异噻唑羧酸衍生物,其制备和其用于保护植物不受有害微生物和动物害虫侵害的应用。
业已知道有许多异噻唑羧酸衍生物具有杀真菌性能(参见,例如,US-A 5240951和JP-A 06-009313)。因此,例如,使用3,4-二氯-异噻唑-5-羧酸异丙酯可以用于防治真菌。此化合物的活性是良好的,但在一些情况下,在低剂量下仍有一些缺憾。
R1代表具有1至12个碳原子的烷基,其中这些基团之每一可以由选自下列的相同或不同取代基单-至三取代:卤素、氰基、硝基、羟基、羧基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分上各具有1至6个碳原子的二烷基氨基、在烷氧基部分具有1至4个碳原子的苯基烷氧基和在杂环基部分具有1至3个杂原子如氮、氧和/或硫和在烷氧基部分具有1至4个碳原子的杂环基烷氧基,或
R1代表具有6至10个碳原子的芳基,它可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R1代表在芳基部分具有6至10个碳原子和在烷基部分具有1至6个碳原子的芳烷基,其中芳基部分可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R1代表在芳基部分具有6至10个碳原子和在氧烷基部分具有1至6个碳原子的芳氧基烷基,其中芳基部分可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基,硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R1代表在杂环基部分具有1至3个杂原子如氮、氧和/或硫和在烷基部分具有1至6个碳原子的任选苯并稠合的杂环基烷基,其中杂环基部分可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R1代表下式的基团:其中
m和n相互独立地各代表从1至3的整数,
R3代表具有1至4个碳原子的烷基或苯基,且
R4代表氢或具有1至4个碳原子的烷基,和
R2代表具有1至12个碳原子的烷基,其中这些基团之每一可以由选自下列的相同或不同取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分上各具有1至6个碳原子的二烷基氨基、在烷氧基部分具有1至4个碳原子的苯基烷氧基和在杂环基部分具有1至3个杂原子如氮、氧和/或硫和在烷氧基部分具有1至4个碳原子的杂环基烷氧基,或
R2代表具有6至10个碳原子的芳基,它可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R2代表在芳基部分具有6至10个碳原子和在烷基部分具有1至6个碳原子的芳烷基,其中芳基部分可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R2代表在芳基部分具有6至10个碳原子和在氧烷基部分具有1至6个碳原子的芳氧基烷基,其中芳基部分可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R2代表在杂环基部分具有1至3个杂原子如氮、氧和/或硫和在烷基部分具有1至6个碳原子的任选苯并稠合的杂环基烷基,其中杂环基部分可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
其中
p和q相互独立地各代表从1至3的整数,
R5代表具有1至4个碳原子的烷基或苯基,且
R6代表氢或具有1至4个碳原子的烷基。
再者,业已发现,式(Ⅰ)的异噻唑羧酸衍生物可以如下制备:
如果适宜在酸结合剂存在下和如果适宜在稀释剂存在下,使式(Ⅱ)的3,4-二氯一异噻唑-5-甲酰氯与式(Ⅲ)化合物反应其中
R如上所定义。
最后,业已发现,式(Ⅰ)异噻唑羧衍生物非常适合于保护植物不受有害微生物的侵害。本发明化合物适合于激发植物对有害微生物侵染进行防御和作为杀微生物剂直接防治微生物。此外,本发明化合物也可以防治损害植物的动物害虫。
出人意外的是,本发明化合物比结构上相似的具有相同作用方式的现有技术化合物3,4-二氨-异噻唑-5-羧酸异丙酯更好的杀微生物活性。
式(Ⅰ)提供本发明异噻唑羧酸衍生物的一般定义。优选的是这样的式(Ⅰ)化合物,其中R 代表基团-OR1或-SR2,其中
R1代表具有1至8碳原子的烷基,其中这些基团之每一可以由选自下列的相同或不同取代基单-至三取代:氟、氯、溴、氰基、硝基、羟基、羧基、具有1至4个碳原子的烷氧基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、具有1至4个碳原子的烷基氨基、在每一烷基部分上各具有1至4个碳原子的二烷基氨基、在烷氧基部分具有1或2个碳原子的苯基烷氧基和在杂环基部分具有1至3个杂原子如氮、氧和/或硫和在烷氧基部分具有1或2个碳原子的五-或六元杂环基烷氧基,或
R1代表苯基,它可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、具有1至4个碳原子的烷基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、在烷氧基部分具有1至4个碳原子的烷氧基羰基、具有1至4个碳原子的烷氧基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、具有1至4个碳原子的烷基氨基、在每一烷基部分各具有1至4个碳原子的二烷基氨基、苯基和苯氧基,或
R1代表在烷基部分具有1至4个碳原子的苯烷基,其中苯基部分可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、具有1至4个碳原子的烷基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、在烷氧基部分具有1至4个碳原子的烷氧基羰基、具有1至4个碳原子的烷氧基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、具有1至4个碳原子的烷基氨基、在每一烷基部分各具有1至4个碳原子的二烷基氨基、苯基和苯氧基,或
R1代表在氧烷基部分具有1至4个碳原子的苯氧基烷基,其中苯基部分可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、具有1至4个碳原子的烷基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、在烷氧基部分具有1至4个碳原子的烷氧基羰基、具有1至4个碳原子的烷氧基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、具有1至4个碳原子的烷基氨基、在每-烷基部分各具有1至4个碳原子的二烷基氨基、苯基和苯氧基,或
R1代表在杂环基部分具有1至3个杂原子如氮、氧和/或硫和在烷基部分具有1至4个碳原子的任选苯并稠合的五-或六元杂环基烷基,其中杂环基部分可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、具有1至4个碳原子的烷基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、在烷氧基部分具有1至4个碳原子的烷氧基羰基、具有1至4个碳原子的烷氧基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、具有1至4个碳原子的烷基氨基、在每一烷基部分各具有1至4个碳原子的二烷基氨基、苯基和苯氧基,或
m和n相互独立地各代表1或2,
R3代表具有1至3个碳原子的烷基或苯基,且
R4代表氢或具有1至3个碳原子的烷基,和
R2代表具有1至8个碳原子的烷基,其中这些基团之每一可以由选自下列的相同或不同取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、具有1至4个碳原子的烷氧基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、具有1至4个碳原子的烷基氨基、在每-烷基部分上各具有1至4个碳原子的二烷基氨基、在烷氧基部分具有1或2个碳原子的苯基烷氧基和在杂环基部分具有1至3个杂原子如氮、氧和/或硫和在烷氧基部分具有1或2个碳原子的五-或六元杂环基烷氧基,或
R2代表具有苯基,它可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、具有1至4个碳原子的烷基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、在烷氧基部分具有1至4个碳原子的烷氧基羰基、具有1至4个碳原子的烷氧基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、具有1至4个碳原子的烷基氨基、在每一烷基部分各具有1至4个碳原子的二烷基氨基、苯基和苯氧基,或
R2代表在烷基部分具有1至4个碳原子的苯烷基,其中芳基部分可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、具有1至4个碳原子的烷基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、在烷氧基部分具有1至4个碳原子的烷氧基羰基、具有1至4个碳原子的烷氧基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、具有1至4个碳原子的烷基氨基、在每一烷基部分各具有1至4个碳原子的二烷基氨基、苯基和苯氧基,或
R2代表在氧烷基部分具有1至4个碳原子的苯氧基烷基,其中芳基部分可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、具有1至4个碳原子的烷基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、在烷氧基部分具有1至4个碳原子的烷氧基羰基、具有1至4个碳原子的烷氧基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、具有1至4个碳原子的烷基氨基、在每一烷基部分各具有1至4个碳原子的二烷基氨基、苯基和苯氧基,或
R2代表在杂环基部分具有1至3个杂原子如氮、氧和/或硫和在烷基部分具有1至4个碳原子的任选苯并稠合的五-或六元杂环基烷基,其中杂环基部分可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、具有1至4个碳原子的烷基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、在烷氧基部分具有1至4个碳原子的烷氧基羰基、具有1至4个碳原子的烷氧基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、具有1至4个碳原子的烷硫基、具有1至4个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、具有1至4个碳原子的烷基氨基、在每一烷基部分各具有1至4个碳原子的二烷基氨基、苯基和苯氧基,或
R1代表下式的基团:其中
p和q相互独立地各代表1或2,
R5代表具有1至3个碳原子的烷基或苯基,且
R6代表氢或具有1至3个碳原子的烷基。
特别优选的是这样的式(Ⅰ)化合物,其中
R代表基团-OR1或-SR2,其中
R1代表具有1至6碳原子的烷基,其中这些基团之每一可以由选自下列的相同或不同取代基单-至三取代:氟、氯、溴、氰基、硝基、羟基、羧基、甲氧基、乙氧基、异丙氧基、叔丁基氧基、具有1至3个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、甲硫基、乙硫基、具有1至3个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、甲基氨基、乙基氨基、二甲基氨基、二乙基氨基、苄氧基或下式的基团
-O-(CH2)r-R7,其中
r代表1或2,和
R7代表吡咯烷基、哌啶基或吗啉基,或
R1代表苯基,它可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、甲氧基羰基、乙氧基羰基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、甲硫基、乙硫基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、甲基氨基、乙基氨基、二甲基氨基、二乙基氨基、苯基和苯氧基,或
R1代表在烷基部分具有1或2个碳原子的苯烷基,其中苯基部分可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、甲氧基羰基、乙氧基羰基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、甲硫基、乙硫基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、甲基氨基、乙基氨基、二甲基氨基、二乙基氨基、苯基和苯氧基,或
R1代表在氧烷基部分具有1或2个碳原子的苯氧基烷基,其中苯基部分可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、甲氧基羰基、乙氧基羰基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、甲硫基、乙硫基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、甲基氨基、乙基氨基、二甲基氨基、二乙基氨基、苯基和苯氧基,或
R1代表下式的基团
-A-R8,其中
A 代表-CH2-、-CH2-CH2-或
和
R8代表吡唑基、咪唑基、1,2,4-三唑基、吡咯基、呋喃基、噻吩基、噻唑基、恶唑基、吡啶基、嘧啶基、三嗪基、1,2,3-三唑基、苯并三唑基、喹啉基、异喹啉基、喹唑啉基、吲哚基、苯并噻吩基、苯并呋喃基、苯并噻唑基或苯并咪唑基,其中这些基团可以由选自下列的相同或不同取代基单-或二取代:氟、氯、溴、氰基、硝基、羧基、甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、甲氧基羰基、乙氧基羰基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、甲硫基、乙硫基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、甲基氨基、乙基氨基、二甲基氨基、二乙基氨基、苯基和苯氧基,或
m和n相互独立地各代表1或2,
R3代表甲基、乙基或苯基,且
R4代表氢、甲基或乙基,和
R2代表具有1至6碳原子的烷基,其中这些基团之每一可以由选自下列的相同或不同取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、甲氧基、乙氧基、异丙氧基、叔丁基氧基、具有1至3个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、甲硫基、乙硫基、具有1至3个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、甲基氨基、乙基氨基、二甲基氨基、二乙基氨基、苄氧基或下式的基团-O-(CH2)s-R9,
其中
s代表1或2,和
R9代表吡咯烷基、哌啶基或吗啉基,或
R代表苯基,它可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、甲氧基羰基、乙氧基羰基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、甲硫基、乙硫基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、甲基氨基、乙基氨基、二甲基氨基、二乙基氨基、苯基和苯氧基,或
R2代表在烷基部分具有1或2个碳原子的苯烷基,其中苯基部分可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、甲氧基羰基、乙氧基羰基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、甲硫基、乙硫基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、甲基氨基、乙基氨基、二甲基氨基、二乙基氨基、苯基和苯氧基,或
R2代表在氧烷基部分具有1或2个碳原子的苯氧基烷基,其中苯基部分可以由选自下列的相同或不同的取代基单-至三取代:氟、氯、溴、氰基、硝基、羧基、甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、甲氧基羰基、乙氧基羰基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、甲硫基、乙硫基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、甲基氨基、乙基氨基、二甲基氨基、二乙基氨基、苯基和苯氧基,或
R2代表下式的基团
-A1-R10,其中
A1 代表-CH2-、-CH2-CH2-或
和
R10代表吡唑基、咪唑基、1,2,4-三唑基、吡咯基、呋喃基、噻吩基、噻唑基、恶唑基、吡啶基、嘧啶基、三嗪基、1,2,3-三唑基、苯并三唑基、喹啉基、异喹啉基、喹唑啉基、吲哚基、苯并噻吩基、苯并呋喃基、苯并噻唑基或苯并咪唑基,其中这些基团可以由选自下列的相同或不同取代基单-或二取代:氟、氯、溴、氰基、硝基、羧基、甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷基、甲氧基羰基、乙氧基羰基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷氧基、甲硫基、乙硫基、具有1或2个碳原子和1至3个氟、氯和/或溴原子的卤代烷硫基、甲基氨基、乙基氨基、二甲基氨基、二乙基氨基、苯基和苯氧基,或
p和q相互独立地各代表1或2,
R5代表甲基、乙基或苯基,且
R6代表氢、甲基或乙基。
上面给出的基团定义可以按需要相互组合。此外,个别的定义也可以不用。
可以提到的本发明化合物的实例是列于下文表格中的式(Ⅰ)异噻唑羧酸衍生物。
表1
表1(续)
表1(续)
进行本发明方法时需作为原料用的式(Ⅱ)的3,4-二氯-异噻唑-5-甲酰氯是已知的(参见,US-A 5240951)。
式(Ⅲ)提供进行本发明方法时所需的另外的反应组分醇和硫醇的一般定义。在此式中,R优选或特别是具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的此基团的优选或特别优选的含义。
适合于本发明方法的酸结合剂是所有的常规的无机或有机碱。这些物质优选包括碱金属或碱土金属的氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或碳酸氢盐,如氢化钠、氨化钠、甲醇钠、乙醇钠、叔丁醇钾、氢氧化钠、氢氧化钾、乙酸钠、乙酸钾、乙酸钙、碳酸钠、碳酸钾、碳酸氢钾以及氢氧化铵、乙酸铵或碳酸铵;或叔胺,如三乙胺、三乙胺、三丁胺、N,N-二甲基苯胺、N,N-二甲基-苄基胺、吡啶、N-甲基-哌啶、N-甲基吗啉、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一烯(DBU)。
适合于进行本发明方法的稀释剂是所有惰性有机溶剂。这些物质优选包括脂肪族、脂环族或芳族的烃,如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或十氢化萘;卤代烃,如氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚类,如乙醚、二异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或苯甲醚;腈类,如乙腈、丙腈、正-或异丁腈或苄腈;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酸三酰胺;酯类,如乙酸甲酯或乙酸乙酯;亚砜类,如二甲基亚砜;砜,如环丁砜。
进行本发明方法时,反应温度可以在较宽的范围内变化。通常,反应是在-10℃至150℃,优选在0℃至100℃间的温度下进行。
本发明方法通常是在常压下进行的。然而,本发明方法可以在加压进行,或如果在反应中无挥发性组分参加则也可以减压下进行。
进行本发明方法时,通常每摩尔的式(Ⅱ)的3,4-二氯-异噻唑-5-甲酰氯采用1至5摩尔、优选1至2摩尔的式(Ⅲ)化合物和等量或过量的酸结合剂。后处理是用常规方法进行的。通常,反应混合物在反应结束后浓缩,余下的残留物与水和仅只稍微与水混溶的有机溶剂混合,并分离掉有机相,洗涤、干燥并浓缩。余下的残留物可以通过常规方法去除可能存在的任何杂质。
本发明化合物具有强的植物增强作用。因此,它们适合于激发植物对有害微生物侵染进行防御。在本文中,植物增加化合物是那些能够刺激植物防御体系的物质,在用它们处理植物后,当随后用有害微生物接种时,植物对这些微生物产生相当大的抗性。
在这种情况下,有害微生物是植物病原真菌、细菌和病毒。本发明化合物还可以在用之处理后的一段时期内保护植物不受上面提到的有害生物侵害。有效的保护时期可延长到植物用活性化合物处理后1至10天,优选1至7天。
除了植物增加作用外,本发明活性化合物还具有强的杀微生物作用和在实际上直接用于防治有害微生物。本发明活性化合物适合用作作物保护剂,特别是杀真菌剂。
在作物保护中,有害微生物包括属于下列纲的真菌:根肿菌纲(Plasmodiophoromycetes)、卵菌纲(Oomycetes)、壶菌纲(Chytridiomycetes)、接合菌纲(Zygomycetes)、子囊菌纲(Ascomycetes)、担子菌纲(Basidiomycetes)和半知菌类(Deuteromycetes)。
上面列出的某些真菌病害的病原生物以属名给出可以提到例如下列,但不限于此:
腐霉属,如终极腐霉(Pythium ultimum);
疫霉属,如蔓延疫霉(Phytophthora infestans);
假霜霉属,如葎草假霜霉(Pseudoperonospora humuli)或古巴假霜霉(P.cubensis);
单轴霉属,如葡萄生单轴霉(P1asmopara viticola);
霜霉属,如豌豆霜霉(Peronospora pisi)或芸苔霜霉(P.brassicae);
白粉菌属,如禾白粉菌(Erysiphe graminis);
单丝壳属,如苍耳单丝壳菌(Sphaerotheca fuliginea);
柄球菌属,如苹果白粉病柄球菌(Podosphaera leucotricha);
黑星菌属,如苹果黑星菌(Venturia inaequalis);
核腔菌属,如圆核腔菌(Pyrenophora teres)或麦类核腔菌(P.graminea)(分生孢子形式:Drechslera,异名:长蠕孢属(Helminthosporium));
旋孢腔菌属,如禾旋孢腔菌(Cochliobolus sativus)(分生孢子形式:Drechslera,异名:长蠕孢属(Helminthosporium));
单孢锈属,如菜豆单孢锈菌(Uromyces appendiculatus);
柄锈属,如隐匿柄锈菌(Puccinia recondita);
腥黑粉菌属,如小麦网腥黑粉菌(Tilletia caries);
黑粉菌属,如裸黑粉菌(Ustilago nuda)或燕麦散黑粉菌(U.avenae);
薄膜革菌属,如佐佐木氏薄膜革菌(Pellicularia sasakii);
梨孢菌属,如稻梨孢菌(Pyricularia oryzae);
镰孢属,如大刀镰孢(Fusarium culmorum);
葡萄孢属,如灰色葡萄孢(Botrytis cinerea);
壳针孢属,如颖枯壳针孢(Septoria nodorum);
小球腔菌属,如颖枯病小球腔菌(Leptosphaeria nodorum);
尾孢属,如变灰尾孢菌(Cercospora canescens);
链格孢属,如甘蓝黑斑病链格孢菌(Alternaria brassicae),和
假小尾孢菌属,如柔毛假小尾孢菌(Pseudocercosporallaherpotrichoides)。
在防治植物病害所需浓度下,本发明活性化合物被植物很好地耐受,使其可以处理植物的地上部分、无性繁殖原种和种子以及土壤。
可以根据本发明使用的活性化合物在此可以特别成功地防治禾谷类病害如防治白粉菌(Eyrsiphe),葡萄、果树和蔬菜生长的病害如防治单轴霉菌(P1asmopara)或黑星菌(Venturia),或稻病害如防治梨孢菌(Pyricularia)。本发明活性化合物还可以成功地防治其它植物病害,如壳针孢(Septoria)、旋孢腔菌(Cochliobolus)、核腔菌(Pyrenophora)和假小尾孢菌(Pseudocercosporella),特别是Drechslera。
本发明活性化合物还适合于增加收获产量。此外,它们具有降低的毒性和良好的作物安全性。
本发明活性化合物适合防治动物害虫,特别是出现在农业、森林、贮藏产品和材料保护以及卫生方面上的昆虫、蜱螨和线虫,且具有良好的作物安全性和对温血动物低毒。它们对正常的敏感和抗性种类和对所有或某些生长发育阶段有活性。上述害虫包括:
等足目,例如,潮虫(Oniscus asellus)、鼠妇(Armadillidiumvulgare)和斑鼠妇(Porcellio scaber)。
倍足目,例如,具斑马陆(Blaniulus guttulatus)。
唇足目,例如,食果地蜈蚣(Geophilus carpophagus)和蚰蜒(Scutigera spec)。
综合目,例如,洁幺蚰(Scutigerella immaculata)。
缨尾目,例如,西洋衣鱼(Lepisma saccharina)。
弹尾目,例如,棘跳虫(Onychiurus armatus)。
直翅目,例如,东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、马德拉蜚蠊(Leucophaea maderae)、德国小蠊(Blattella germanica)、家蟋蟀(Achetadomesticus)、蝼蛄属(Gryllotalpa spp.)、热带飞蝗(Locustamigratoria migratorioids)、殊种蚱蜢(Melanoplusdifferentialis)和沙漠蝗(Schistocerca gregaria)。
革翅目,例如,欧洲球螋(Forficula auricularia)。
等翅目,例如,犀白蚁属(Reticulitermes spp.)。
虱目,例如,体虱(Pediculus humanus corporis)、血虱属(Haematopinus spp.)和颚虱属(Linognathus spp.)。
食毛目,例如,啮毛虱属(Trichodectes spp.)和畜属虱(Damalinea spp.)。
缨翅目,例如,温室条蓟马(Hercinothrips femoralis)和棉蓟马(Thrips tabaci)。
半翅目,例如,扁盾蝽属(Eurygaster spp.)、中棉红蝽(Dysdercus intermedius)、甜菜拟网蝽(Piesma quadrata)、温带臭蝽(Cimex lectularius)、长红猎蝽(Rhodnius prolixus)和锥蝽属(Triatoma spp.)。
同翅目,例如,甘蓝粉虱(Aleurodes brassicae)、甘薯粉虱(Bemisia tabaci)、温室粉虱(Trialeurodes vaporariorum)、棉蚜(Aphis gossypii)、甘蓝蚜(Brevicoryne brassicae)、茶藨隐瘤蚜(Cryptomyzus ribis)、甜菜蚜(Aphis fabae)、苹果蚜(Aphispomi)、苹果绵蚜(Eriosoma lanigerum)、桃大尾蚜(Hyalopterusarundinis)、美核桃根瘤蚜(Phylloxera vaststrix)、瘿绵蚜属(Pemphigus spp.)、麦长管蚜(Macrosiphum avenae)、瘤额蚜属(Myzus spp.)、忽布疣蚜(Phorodon humili)、禾谷缢管蚜(Rhopalosiphum padi)、微叶蝉属(Empoasca spp.)、钝鼻叶蝉(Euscelis bilobatus)、黑尾叶蝉(Nephotettix cincticeps)、水土坚蚧(Lecanium corni)、油榄黑盔蚧(Saissetia oleae)、灰稻虱(Laodelphax striatellus)、稻褐飞虱(Nilaparvatalugens)、红肾园盾蚧(Aonidiella aurantii)、夹竹桃园蚧(Aspidiotus hederae)、粉蚧属(Pseudococcus spp.)和木虱属(Psylla spp.)。
鳞翅目,例如,棉红蛉虫(Pectinophora gossypiella)、松天蛾(Bupalus piniarius)、冬尺蛾(Cheimatobia brumata)、苹细蛾(Lithocolletis blancardella)、苹果巢蛾(Hyponomeutapadella)、小菜蛾(Plutella maculipennis)、天幕毛虫(Malacosoma neustris)、黄毒蛾(Euproctis chrysorrhoea)、毒蛾属(Lymantria spp.)、棉潜蛾(Bucculatrix thurberiella)、桔潜叶蛾(Phyllocnistis citrella)、地老虎属(Agrotis spp.)、切根虫属(Euxoa spp.)、夜蛾属(Feltia spp.)、棉斑实蛾(Eariasinsulana)、棉铃虫属(Heliothis spp.)、甜菜夜蛾(Spodopteraexigua)、甘蓝夜蛾(Mamestra brassicae)、小眼夜蛾(Panolisflammea)、斜纹夜蛾(Prodenia litura)、灰翅夜蛾属(Spodopteraspp.)、粉纹夜蛾(Trichoplusia ni)、苹蠹蛾(Carpocapsapomonella)、粉蝶属(Pieris spp.)、禾草螟属(Chilo spp.)、玉米螟(Pyrausta nubilalis)、地中海粉斑螟(Ephestiakuehniella)、大蜡螟(Galleria mellonella)、幕衣蛾(Tineolabisselliella)、袋衣蛾(Tinea pellionella)、褐织蛾(Hofmannophila pseudospretella)、亚麻黄卷蛾(Cacoeciapodana)、Capua reticulana、枞色卷蛾(Choristoneurafumiferana)、葡萄果蠹蛾(Clysia ambiguella)、茶长卷蛾(Homonamagnanima)和栎绿卷蛾(Tortrix viridana)。
鞘翅目,例如,具斑窃蠹(Anobium punctatum)、谷蠹(Rhizopertha dominica)、豆象(Bruchidius obtectus)、大豆象(Acanthoscelides obtectus)、家天牛(Hylotrupes bajulus)、赤杨紫跳甲(Agelasrtica alni)、马铃薯甲虫(Leptinotarsadecemlineata)、辣根猿叶甲(Phaedon coehleariae)、条叶甲属(Diabrotica spp.)、油菜蓝跳甲(Psylliodes chrysocephala)、墨西哥豆甲(Epilachna varivestis)、隐翅甲属(Atomariaspp.)、锯谷盗(Oryzaephilus surinamensis)、花象甲属(Anthonomus spp.)、米象属(Sitophilus spp.)、葡萄黑耳喙象(Otiorrhynchus sulcatus)、香蕉根象甲(Cosmopo1itessordidus)、甘蓝荚象甲(Ceuthorrhynchus assimilis)、苜蓿叶象虫(Hypera postica)、皮蠹属(Dermestes spp.)、斑皮蠹属(Trogoderma spp.)、圆皮蠹属(Anthrenus spp.)、毛蠹属(Attagenus spp.)、粉蠹属(Lyctus spp.)、油菜花露尾甲(Meligethes aeneus)、蛛甲属(Ptinus spp.)、金黄蛛甲(Niptusho1o1eucus)、裸蛛甲(Gibbium psylloides)、拟谷盗属(Tribo1iumspp.)、黄粉虫(Tenebrio mo1itor)、叩头虫属(Agriotes spp.)、宽胸叩头虫属(Conoderus spp.)、西方五月鳃角金龟(Melolonthamelolontha)、马铃薯鳃角金龟(Amphimallon sostitialis)和褐新西兰肋翅鳃角金龟(Costelytra zealandica)。
膜翅目,例如,锯角叶蜂属(Diprion spp.)、叶蜂属(Hoplocampaspp.)、田蚁属(Lasius spp.)、小家蚁(Monomorium pharaonis)和胡蜂(Vespa spp.)。
双翅目,例如,伊蚊属(Aedes spp.)、按蚊属(Anophelesspp.)、库蚊属(Culex spp.)、黄猩猩果蝇(Drosophilamelanogaster)、蝇属(Musca spp.)、厕蝇属(Fannia spp.)、红头丽蝇(Callophora erythrocephala)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、疽蝇属(Cuterebra spp.)、胃蝇属(Gastrophilus spp.)、虱蝇属(Hyppobosca spp.)、螫蝇属(Stomoxys spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypodermaspp.)、虻属(Tabanus spp.)、螗蜩属(Tannia spp.)、花园毛蚊(Bibio hortulanus)、瑞典麦杆蝇(Oscinella frit)、草种蝇属(Phorbia spp.)、菠菜潜叶花蝇(Pegomyia hyoscyami)、地中海实蝇(Ceratitis capitata)、油榄实蝇(Dacus oleae)和沼泽大蚊(Tipula paludosa)。
蚤目,例如,印鼠客蚤(Xenopsylla cheopis)和毛列蚤属(Ceratophyllus spp.)。
蛛形目,例如,蝎(Scorpio maurus)和毒寇蛛(Latrodectusmactans)。
蜱螨目,例如,粗脚粉螨(Acarus siro)、隐喙蜱属(Argasspp.)、钝喙蜱属(Ornithodoros spp.)、鸡皮刺螨(Dermanyssusgallinae)、茶 瘿螨(Eriophyes ribis)、柑桔锈螨(Phyllocoptruta o1eivora)、牛蜱属(Boophilus spp.)、扇头蜱属(Rhipicephalus spp.)、花蜱属(Amblyomma spp.)、玻眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、瘙螨属(Psoroptesspp.)、皮螨属(Chorioptes spp.)、疥螨属(Sarcoptes spp.)、跗线螨属(Tarsonemus spp.)、苜蓿苔螨(Bryobia praetiosa)、全爪螨属(Panonychus spp.)和叶螨属(Tetranychus spp.)。
植物寄生线虫包括例如短体属(Pratylenchus spp.)、相似穿孔线虫(Radopholus similis)、起绒线茎线虫(Ditylenchusdipsaci)、半穿刺线虫(Tylenchulus semipenetrana)、异皮线虫属(Heterodera spp.)、球异皮线虫属(G1obodera spp.)、根结属(Meloidogyne spp.)、滑刃属(Aphelechoides spp.)、长针属(Longidorus spp.)、剑线虫属(Xiphinema spp.)和毛刺属(Tri chodorus spp.)。
本发明化合物可以采用来特别成功地防治植食性螨,如防治二点叶螨(Tetranychus urticae)或用于防治植食性昆虫,如防治小菜蛾(Plutella maculipennis)幼虫、辣根猿叶甲(Phaedon cochleariae)幼虫和黑尾叶蝉(Nephotettix cincticeps)。
本发明化合物还具有除草活性。
取决于其特定的物理和/或化学性能,活性化合物可以转化成常规的剂型,如溶液、乳剂、悬浮剂、粉剂、泡沫剂、膏剂、颗粒剂、气雾剂和包在聚合物中的微胶囊剂和用于种子的包衣组合物,以及ULV冷和热气雾剂。
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、加压下的液化气和/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/或泡沫形成剂。在用水作扩充剂的情况下,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,氯代芳族化合物或氯代脂肪烃,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,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。液化气扩充剂或载体应理解为是指在常温和常压下是气体的液体,例如气雾剂抛射剂如卤代烃,或是丁烷、丙烷、氮气和二氧化碳。适合的固体载体是:例如磨碎的天然岩石如高岭土、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。用于颗粒剂的固体载体适合的有: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、玉米穗轴和烟茎。适合的乳化剂和/或泡沫形成剂是: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,和微量营养素如铁、锰、硼、铜、钴、钼和锌盐。
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%。
可以根据本发明使用的活性化合物可以以其原样或也可以是其与其它活性化合物混合的制剂,例如与已知的杀真菌剂、杀细菌剂、杀螨剂、杀线虫剂或杀虫剂混合,由此而拓宽作用谱或防治抗性产生。在许多情况下,可以获得增效作用,即,混合物的活性超过单独组分的活性。
混合物中共组分的实例是如下化合物:
杀真菌剂:
aldimorph、氨丙磷酸、氨丙磷酸钾、andoprim、敌菌灵、戊环唑、嘧菌酯、
苯霜灵、碘萎灵、苯菌灵、benzamacil、benzamacil-isobutyl、双丙氨酰磷、乐杀螨、联苯、双苯三唑醇、灭瘟素、糠菌唑、磺酸丁嘧啶、丁赛特、
石硫合剂、capsimycin、敌菌丹、克菌丹、多菌灵、萎锈灵、carvon、灭螨猛、灭瘟唑、地茂散、chlorofenazo1e、氯苯甲醚、氯化苦、百菌清、乙菌利、clozylacon、硫杂灵、霜脲氰、环唑醇、嘧菌环胺、酯菌胺、
咪菌威、防霉酚、苄氯三唑醇、抑菌灵、哒菌清、氯硝胺、乙霉威、噁醚唑、甲嘧醇、烯酰吗啉、烯唑醇、烯唑醇-M、清螨普、二苯胺、吡菌硫、灭菌磷、二噻农、十二吗啉、多果定、腙菌酮、
克菌散、氟环唑、乙环唑、乙嘧酚、氯唑灵、
famoxadon、咪菌腈、氯苯嘧啶醇、苯氰唑、呋菌胺、种衣酯、拌种咯、苯锈啶、丁苯吗啉、乙酸三苯基锡、三苯羟基锡、福美铁、嘧菌腙、氟啶胺、flumetover、氟氯菌核利、氟喹唑、氟哇唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、乙磷钠、四氯苯酞、麦穗宁、呋霜灵、furametpyr、二甲呋酰苯胺、呋菌唑、呋醚唑、拌种胺、
双胍锌乙酸盐、
六氯苯、己唑醇、甲羟异噁唑、抑霉唑、酰胺唑、双胍辛胺、双胍辛烷苯基磺酸盐、双胍辛胺乙酸盐、iodocarb、种菌唑、异稻瘟净(IBP)、异菌脲、irumamycin、稻瘟灵、isovaledione、
春日霉素、醚菌酯、铜制剂,如氢氧化铜、环烷酸铜、碱式氯化铜、硫酸铜、氧化铜、喹啉酮和波尔多混合物、
双代混剂、代森锰锌、代森锰、meferimzone、嘧菌胺、灭锈胺、甲霜灵、叶菌唑、磺菌威、呋菌胺、代森联、氯苯咯菌胺、噻菌胺、米多霉素、腈菌唑、甲菌利、
福美镍、异丙消、氟苯嘧啶醇、
甲呋酰胺、噁酰胺、oxamocarb、喹菌酮、氧化萎锈灵、oxyfenthiin、
多效唑、稻瘟酯、戊菌唑、戊菌隆、稻病磷、稻瘟酞、匹马菌素、哌啶宁、多氧霉素、po1yoxorim、烯丙异噻唑、咪鲜安、二甲菌核利、霜霉威、propanosine-sodium、丙环唑、甲基代森锌、定菌磷、啶斑肟、嘧霉胺、咯喹酮、氯吡呋醚、
quinconazole、五氯硝基苯、
硫磺和硫制剂、
戊唑醇、酞枯酸、四氯硝基苯、调环烯、氟醚唑、噻菌灵、噻菌腈、噻呋酰胺、甲基托布津、福美双、甲基立枯灵、对甲抑菌灵、三唑酮、三唑醇、triabutil、唑菌嗪、杨菌胺、三环唑、环吗啉、氟菌唑、嗪氨灵、灭菌唑、
烯效唑、
稻纹散、乙烯菌核利、烯霜苄唑、
氰菌胺、代森锌、福美锌,以及
Dagger G、OK-8705、OK-8801、
α-(1,1-二甲基乙基)-β-(2-苯氧基乙基)-1H-1,2,4-三唑-1-乙醇、
α-(2,4-二氯苯基)-β-氟-b-丙基-1H-1,2,4-三唑-1-乙醇、
α-(2,4-二氯苯基)-β-甲氧基-a-甲基-1H-1,2,4-三唑-1-乙醇、
α-(5-甲基-1,3-二噁烷-5-基)-β-[[4-(三氟甲基)-苯基]-亚甲基]-1,2,4-三唑-1-乙醇、
(5RS,6RS)-6-羟基-2,2,7,7-四甲基-5-(1H-1,2,4-三唑-1-基)-3-辛酮、
(E)-α-(甲氧基亚氨基)-N-甲基-2-苯氧基-苯基乙酰胺、
{2-甲基-1-[[[1-(4-甲基苯基)乙基]氨基]羰基]丙基}-氨基甲酸异丙酯、
1-(2,4-二氯苯基)-2-(1H-1,2,4-三唑-1-基)乙酮-O-(苯基甲基)-肟、
1-(2-甲基-1-萘基)-1H-吡咯-2,5-二酮,
1-(3,5-二氯苯基)-3-(2-丙烯基)-2,5-吡咯烷二酮、
1-[(二碘甲基)-磺酰基]-4-甲基-苯、
1-[[2-(2,4-二氯苯基)-1,3-二氧戊烷-2-基]-甲基]-1H-咪唑、
1-[[2-(4-氯苯基)-3-苯基环氧乙烷基]-甲基]-1H-1,2,4-三唑、
1-[1-[2-[(2,4-二氯苯基)甲氧基]苯基]乙烯基]-1H-咪唑、
1-甲基-5-壬基-2-(苯基甲基)-3-吡咯烷脑、
2,6’-二溴-2-甲基-4’-三氟甲氧基-4’-三氟甲基-1,3-噻唑-5-甲酰苯胺、
2,2-二氯-N-[1-(4-氯苯基)乙基]-1-乙基-3-甲基-环丙烷羧酰胺、
2,6-二氯-5-(甲硫基)-4-嘧啶基硫氰酸酯、
2,6-二氯-N-(4-三氟甲基苄基)-苯甲酰胺、
2,6-二氯-N-[[4-(三氟甲基)苯基]甲基]-苯甲酰胺、
2-(2,3,3-三碘-2-丙烯基)-2H-四唑、
2-[(1-甲基乙基)磺酰基]-5-(三氯甲基)-1,3,4-噻二唑、
2-[[6-脱氧-4-O-(4-O-甲基-β-D-葡糖吡喃基)-a-D-葡糖吡喃基]-氨基]-4-甲氧基-1H-吡咯并[2,3-d]嘧啶-5-腈、
2-氨基丁烷、
2-溴-2-(溴甲基)-戊二腈、
2-氯-N-(2,3-二氢-1,1,3-三甲基-1H-茚-4-基)-3-嘧啶甲酰胺、
2-氯-N-(2,6-二甲基苯基)-N-(异氰硫基甲基)-乙酰胺、
2-苯基苯酚(OPP)、
3,4-二氯-1-[4-(二氟甲氧基)-苯基]-1H-吡咯-2,5-二酮、
3,5-二氯-N-[氰基-[(1-甲基-2-丙炔基)氧基]甲基]-苯甲酰胺、
3-(1,1-二甲基丙基-1-氧代-1H-茚-2-腈、
3-[2-(4-氯苯基)-5-乙氧基-3-异噁唑烷基]-吡啶、
4-氯-2-氰基-N,N-二甲基-5-(4-甲基苯基)-1H-咪唑-1-磺酰胺、
4-甲基-四唑并[1,5-a]-喹啉-5(4H)-酮、
8-(1,1-二甲基乙基)-N-乙基-N-丙基-1,4-二氧杂螺[4.5]癸-2-甲胺、
8-羟基喹啉硫酸盐、
9H-呫吨-2-[(苯基氨基)-羰基]-9-羧酸肼、
双-(1-甲基乙基)-3-甲基-4-[(3-甲基苯甲酰基)氧基]-2,5-噻吩二羧酸酯、
顺-1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)-环庚醇、
顺-4-[3-[4-(1,1-二甲基丙基)-苯基]-2-甲基丙基]-2,6-二甲基-吗啉盐酸盐、
[(4-氯苯基)-氮杂]-氨基乙酸乙酯、
碳酸氢钾、
甲基四硫醇-钠盐、
1-(2,3-二氢-2,2-二甲基-1H-茚-1-基)-1H-咪唑-5-羧酸甲酯、
N-(2,6-二甲基苯基)-N-(5-异恶唑羰基)-DL-丙氨酸酯、
N-(氯乙酰基)-N-(2,6-二甲基苯基)-DL-丙氨酸甲酯、
N-(2,3-二氯-4-羟基苯基)-1-甲基-环己烷羧酰胺、
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-呋喃基)-乙酰胺、
N-(2,6-二甲基苯基)-2-甲氧基-N-(四氢-2-氧代-3-噻吩基)-乙酰胺、
N-(2-氯-4-硝基苯基)-4-甲基-3-硝基-2-苯磺酰胺、
N-(4-环己基苯基)-1,4,5,6-四氢-2-吡啶胺、
N-(4-己基苯基)-1,4,5,6-四氯-2-嘧啶胺、
N-(5-氯-2-甲基苯基)-2-甲氧基-N-(2-氧代-3-恶唑烷基)-乙酰胺、
N-(6-甲氧基)-3-吡啶基)-环丙烷羧酰胺、
N-[2,2,2-三氯-1-[(氯乙酰基)-氨基]-乙基]-苯甲酰胺、
N-[3-氯-4,5-双(2-丙炔氧基)-苯基]-N’-甲氧基-甲基亚氨酰胺、
N-甲酰基-N-羟基-DL-丙氨酸钠盐、
O,O-二乙基[2-(二丙基氨基)-2-氧代乙基]-乙基硫代磷酰胺、
O-甲基S-苯基苯基丙基硫代磷酰胺、
S-甲基1,2,3-苯并噻二唑-7-硫代羧酸酯、
螺[2H]-1-苯并吡喃-2,1’(3’H)-异苯并呋喃]-3’-酮、
杀细菌剂:
拌棉酚、防霉酚、氯定、福美镍、春日霉素、异噻菌酮、呋喃羧酸、土霉素、烯丙异噻唑、链霉素、酞枯酸、硫酸铜和其它铜制剂。
杀虫剂/杀螨剂/杀线虫剂:
齐墩螨素、乙酰甲胺磷、氟酯菊酯、棉铃威、涕灭威、甲体氯氰菊酯、双甲脒、阿凡曼菌素、AZ 60541、苦楝素、乙基谷硫磷、谷硫磷、三唑锡、
苏芸金杆菌、4-溴-2-(4-氯苯基)-1-(乙氧基甲基)-5-(三氟甲基)-H-吡咯-3-腈、苯噁威、丙硫克百威、杀虫磺、乙体氟氯氰菊酯、联苯菊酯、丁苯威、溴醚菊酯(brofenprox)、溴硫磷、混戊威、噻嗪酮、丁酮威、丁基哒螨酮、
硫线磷、西维因、克百威、三硫磷、丁硫克百威、巴丹、除线威、氯氧磷、毒虫畏、定虫隆、氯甲硫磷、N-[(6-氯-3-吡啶基)-甲基]-N’-氰基-N-甲基-乙亚氨酰胺、毒死蜱、甲基毒死蜱、顺式苄呋菊酯、三氟氯氰菊酯、四螨嗪、杀螟腈、乙氰菊酯、氟氯氰菊酯、氯氟氰菊酯、三环锡、氯氰菊酯、灭蝇胺、
溴氰菊酯、甲基内吸磷、内吸磷、异吸磷Ⅱ、杀螨隆、地亚农、氯线磷、敌敌畏、dicliphos、百治磷、乙硫磷、伏虫脲、乐果、甲基毒虫畏、二噁硫磷、乙拌磷、
克瘟散、emamectin、高氰戊菊酯、除蚜威、乙硫磷、醚菊酯、丙线磷、乙嘧硫磷、
克线磷、喹螨醚、螨完锡、杀螟硫磷、仲丁威、苯硫威、双氧威、甲氰菊酯、fenpyrad、唑螨酯、倍硫磷、氰戊菊酯、氟虫腈、氟啶胺、啶虫蜱、氟螨脲、氟氰戊菊酯、氟虫脲、氟醚菊酯(flufenprox)、氟胺氰菊酯、地虫硫磷、安果、噻唑硫磷、溴醚菊酯(fubfenprox)、呋线威、
六六六、庚虫磷、氟铃脲、噻螨酮、
吡虫啉、异稻瘟净、氯唑磷、异丙胺磷、异丙威、噁唑磷、伊维菌素、λ-三氟氯氰菊酯、虱螨脲、
马拉硫磷、灭蚜硫磷、速灭磷、倍硫磷亚砜、蜗牛敌、虫螨畏、甲胺磷、甲噻硫磷、甲硫威、灭多威、速灭威、米尔倍菌素、久效磷、moxidectin、
二溴磷、NC 184、烯啶虫胺、
氧乐果、草肟威、砜吸硫磷、异砜磷、
对硫磷、甲基对硫磷、氯菊酯、稻丰散、甲拌磷、伏杀硫磷、亚胺硫磷、磷胺、辛硫磷、抗蚜威、甲基嘧啶硫磷、嘧啶硫磷、丙溴磷、甲丙威、丙虫威、残杀威、低毒硫磷、发果、pymetrozin、吡唑硫磷、苯哒嗪硫磷、反灭菊酯、除虫菊酯、哒螨酮、嘧螨醚、蚊蝇醚、
喹硫磷、
水杨硫磷、硫线磷、氟硅菊酯、治螟磷、甲丙硫磷、
虫酰肼、吡螨胺、特丁嘧啶硫磷、伏虫隆、七氟菊酯、双硫磷、叔丁威、特丁甲拌磷、杀虫畏、thiafanox、硫双灭多威、己酮肟威、甲基乙拌磷、喹线磷、苏芸金菌素、四溴菊酯、苯赛螨、三唑磷、triazuron、敌百虫、杀虫隆、混杀威、
完灭硫磷、二甲威、二甲苯威、zetamethrin。
也可以与其它已知活性化合物,如除草剂或化肥和生长调节剂混合。
本发明活性化合物可以以其原样、其制剂形式或由此制剂制备的使用形式使用,如直接可用溶液、悬浮剂、可湿性粉剂、膏剂、可溶性粉剂、粉剂和颗粒剂。它们可以以常规的方式使用,例如通过浇泼、喷雾、弥雾、撒施、喷粉、起泡沫、涮涂等。还可以通过超低容量方法施用活性化合物,或将活性化合物制剂或活性化合物本身注入土壤。也可以处理植物的种子。
当本发明活性化合物用作防治微生物时,取决于施用的类型,施用剂量可以在较宽的范围内变化。在处理植物部分时,活性化合物的施用剂量通常在0.1至10,000g/ha,优选10至1000g/ha之间。在处理种子时,活性化合物的施用剂量通常在0.001至50g/kg种子,优选0.01至10g/kg种子之间。在处理土壤时,活性化合物的施用剂量通常在0.1至10,000g/ha,优选1至5000g/ha之间。
同样,当用来防治动物害虫时,本发明化合物可以以市售制剂形式存在,也可以以由这些制剂制备的使用形式作为与增效剂一起的混合物存在。增效剂增加活性化合物的活性,但它本身无需有活性。
由市售制剂制备的使用形式中的本发明化合物含量可以在相当宽的范围内变化。使用形式的活性化合物浓度可以是按重量计0.0000001至95%的活性化合物,优选按重量计0.0001至1%。
施用可以用适合于使用形式的方式进行。
本发明活性化合物的制备和使用通过下列实施例来说明。
制备实施例
在5至10℃下,用10分钟在搅拌下将77.37克(0.3摩尔)3,4-二氯异噻唑-5-甲酰氯滴加入到31克(0.345摩尔)N,N-二甲基-乙醇胺和350亳升吡啶中。加毕,将反应混合物与260亳升四氢呋喃混合,并温热至室温,之后在室温下搅拌2小时。随后将反应混合物减压浓缩。余下的残留物用500亳升水和500亳升乙酸乙酯搅拌。将不同的相分离,水相用300亳升乙酸乙酯再洗涤一次。合并的有机相先用450亳升碳酸氢钠水溶液,然后用300亳升氯化钠水溶液洗涤,之后减压浓缩。余下的产物与乙酸乙酯混合。所得的沉淀物抽吸滤出,并干燥。由此给出1.17克晶体产物,熔点:127至129℃。
由最初获得的水相,分离出晶体沉淀物,将之抽吸滤出并干燥。由此给出22.35克晶体产物,熔点129至130℃。
在室温下静置48小时后,由水相母液再分离出一次固体,并将此固体抽吸滤出并干燥。由此给出10.25克晶体产物,熔点128至130℃。
获得总量为32.6克(理论值的39.15%)3,4-二氯-异噻唑-5-羧酸(2-二甲基氨基)乙基酯。
在室温下,用5分钟将146克(1.23摩尔)亚磺酰氯滴加入到8.92克(0.045摩尔)3,4-二氯-异噻唑-5-羧酸中。之后加入4滴二甲基甲酰胺,并将反应混合物加热回流1小时。随后将反应混合物冷却到室温,并减压浓缩。由此给出12.19克 3,4-二氯-异噻唑-5-甲酰氯,为橙色油形式。
通过上面给出的方法也可以制备出列于下文表格中的式(Ⅰ)化合物。
表2
表2(续)
·) 表1中的1ogP是通过HPLC(梯度法,乙腈/0.1%磷酸水溶液),用EEC Directive 79/831 Annex V.A8测定的。
··)λ值指在UV中的最大值。
实施例A
稻瘟病(Pyricularia)试验(稻)/诱导抗性
溶剂: 2.5份重量的丙酮
乳化剂: 0.06份重量的烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1份重量的活性化合物与所述量的溶剂混合,并将浓缩物用水和所述量的乳化剂稀释成所需要浓度。
试验抗性诱导活性时,将稻秧用活性化合物制剂以所述的施用剂量喷雾.处理5天后,将稻株用稻梨孢(Pyricularia oryzae)的孢子水悬浮液接种。随后将稻株放置于100%相对湿度和25℃温度下的温室中。
接种4天后进行评价。0%指效力相当于对照,100%的效力指未观察到感染。
活性化合物、施用剂量和试验结果示于下文表格中。
表A
稻瘟病试验(稻)/诱导抗性
表A(续)
表A(续)
稻瘟病试验/诱导抗性
实施例B
小菜蛾(Plutella)试验
溶剂: 7份重量的二甲基甲酰胺
乳化剂: 1份重量的烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1份重量的活性化合物与所述量的溶剂与乳化剂混合,并将乳油用水稀释成所需要浓度。
将甘蓝(Brassica oleracea)叶浸入所需浓度的活性化合物制剂中处理,在叶片仍湿润时,移入小菜蛾(P1utella xylostella)幼虫。
7天后,测定杀死率。效力100%指所有的幼虫均被杀死,0%指没有幼虫被杀死。
活性化合物、活性化合物浓度和试验结果示于下文表格中。
表B
实施例C
大麦白粉病(Erysiphe)保护性防治试验
溶剂: 10份重量的N-甲基吡咯烷酮
乳化剂: 0.6份重量的烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1份重量的活性化合物与所述量的溶剂与乳化剂混合,并将乳油用水稀释成所需要浓度。
为试验保护性活性,将幼苗用活性化合物制剂以所述的施用剂量喷雾。
在喷雾液层变干后,将植株用大麦白粉菌(Erysiphe graminisf.sp.hordei)的孢子喷粉。
将植株放置于大约20℃和大约80%相对湿度的温室中,以促进的白粉病斑产生。
接种7天后进行评价。0%指效力相当于对照,100%的效力指来观察到感染。
活性化合物、施用剂量和试验结果示于下文表格中。
表C
大麦白粉病保护性试验
实施例D
小麦颖枯粉病(Leptosphaeria nodorum)保护性防治试验
溶剂: 10份重量的N-甲基-吡咯烷酮
乳化剂: 0.6份重量的烷芳基聚乙二醇醚
为制备适合的活性化合物制剂,将1份重量的活性化合物与所述量的溶剂与乳化剂混合,并此乳油用水稀释成所需要浓度。
为试验保护性活性,将幼苗用活性化合物制剂以所述的施用剂量喷雾。在喷雾液层变干后,将植株用小麦颖枯病菌(Leptosphaerianodorum)的孢子悬浮液喷雾。将植株留在20℃和100%相对湿度的培养箱中48小时。
将植株放置于大约15℃和大约80%相对湿度的温室中,以促进的白粉病斑产生。
接种10天后进行评价。0%指效力相当于对照,100%的效力指未观察到感染。
活性化合物、施用剂量和试验结果示于下文表格中。
表D
小麦颖枯病保护性试验
Claims (10)
R1代表具有1至12个碳原子的烷基,其中这些基团之每一可以由选自下列的相同或不同取代基单-至三取代:卤素、氰基、硝基、羟基、羧基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分上各具有1至6个碳原子的二烷基氨基、在烷氧基部分具有1至4个碳原子的苯基烷氧基和在杂环基部分具有1至3个杂原子如氮、氧和/或硫和在烷氧基部分具有1至4个碳原子的杂环基烷氧基,或
R1代表具有6至10个碳原子的芳基,它可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R1代表在芳基部分具有6至10个碳原子和在烷基部分具有1至6个碳原子的芳烷基,其中芳基部分可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R1代表在芳基部分具有6至10个碳原子和在氧烷基部分具有1至6个碳原子的芳氧基烷基,其中芳基部分可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R1代表在杂环基部分具有1至3个杂原子如氮、氧和/或硫和在烷基部分具有1至6个碳原子的任选苯并稠合的杂环基烷基,其中杂环基部分可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
其中
m和n相互独立地各代表从1至3的整数,
R3代表具有1至4个碳原子的烷基或苯基,且
R4代表氢或具有1至4个碳原子的烷基,和
R2代表具有1至12个碳原子的烷基,其中这些基团之每一可以由选自下列的相同或不同取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分上各具有1至6个碳原子的二烷基氨基、在烷氧基部分具有1至4个碳原子的苯基烷氧基和在杂环基部分具有1至3个杂原子如氮、氧和/或硫和在烷氧基部分具有1至4个碳原子的杂环基烷氧基,或
R2代表具有6至10个碳原子的芳基,它可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R2代表在芳基部分具有6至10个碳原子和在烷基部分具有1至6个碳原子的芳烷基,其中芳基部分可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R2代表在芳基部分具有6至10个碳原子和在氧烷基部分具有1至6个碳原子的芳氧基烷基,其中芳基部分可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
R2代表在杂环基部分具有1至3个杂原子如氮、氧和/或硫和在烷基部分具有1至6个碳原子的任选苯并稠合的杂环基烷基,其中杂环基部分可以由选自下列的相同或不同的取代基单-至三取代:卤素、氰基、硝基、羧基、具有1至6个碳原子的烷基、具有1至6个碳原子和1至5个卤原子的卤代烷基、在烷氧基部分具有1至6个碳原子的烷氧基羰基、具有1至6个碳原子的烷氧基、具有1至6个碳原子和1至5个卤原子的卤代烷氧基、具有1至6个碳原子的烷硫基、具有1至6个碳原子和1至5个卤原子的卤代烷硫基、具有1至6个碳原子的烷基氨基、在每一烷基部分各具有1至6个碳原子的二烷基氨基、苯基和苯氧基,或
其中
p和q相互独立地各代表从1至3的整数,
R5代表具有1至4个碳原子的烷基或苯基,且
R6代表氢或具有1至4个碳原子的烷基。
3.保护植物不受有害微生物和动物害虫侵害的组合物,其特征在于,除了扩充剂和表面活性剂之外,它们还含有至少一种权利要求1的式(Ⅰ)的异噻唑羧酸衍生物。
4.权利要求1的式(Ⅰ)的异噻唑羧酸衍生物用于保护植物不受有害微生物和动物害虫侵害的应用。
5.保护植物不受有害微生物和动物害虫侵害的方法,其特征在于,将权利要求1的式(Ⅰ)的异噻唑羧酸衍生物施用于植物和/或其栖生地。
6.制备保护植物不受有害微生物和动物害虫侵害的组合物的方法,其特征在于,将权利要求1的式(Ⅰ)的异噻吩羧酸衍生物与扩充剂和/或表面活性剂混合。
7.权利要求1的异噻唑羧酸衍生物,其特征在于,它是下式化合物
9.权利要求1的异噻唑羧酸衍生物,其特征在于,它是下式化合物
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19750011A DE19750011A1 (de) | 1997-11-12 | 1997-11-12 | Isothiazolcarbonsäure-Derivate |
DE19750011.0 | 1997-11-12 |
Publications (2)
Publication Number | Publication Date |
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CN1278804A true CN1278804A (zh) | 2001-01-03 |
CN1121399C CN1121399C (zh) | 2003-09-17 |
Family
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CN98811083.0A Expired - Fee Related CN1121399C (zh) | 1997-11-12 | 1998-11-03 | 异噻唑羧酸衍生物 |
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US (1) | US6191155B1 (zh) |
EP (1) | EP1044195A1 (zh) |
JP (1) | JP4511720B2 (zh) |
KR (1) | KR100577614B1 (zh) |
CN (1) | CN1121399C (zh) |
AR (1) | AR016008A1 (zh) |
AU (1) | AU1559199A (zh) |
BR (1) | BR9814134A (zh) |
CO (1) | CO5040010A1 (zh) |
DE (1) | DE19750011A1 (zh) |
PL (1) | PL340461A1 (zh) |
RU (1) | RU2205180C2 (zh) |
TW (1) | TW502028B (zh) |
WO (1) | WO1999024414A1 (zh) |
ZA (1) | ZA9810298B (zh) |
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CN102942565A (zh) * | 2012-11-06 | 2013-02-27 | 江西天人生态股份有限公司 | 一类3,4-二氯异噻唑衍生物及其制备方法和用途 |
CN108031305A (zh) * | 2017-12-23 | 2018-05-15 | 刘顶康 | 一种延长聚烯烃微滤膜抗菌持久性的方法 |
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JP2001122864A (ja) * | 1999-10-20 | 2001-05-08 | Nippon Bayer Agrochem Co Ltd | イソチアゾールカルボン酸誘導体 |
JP2001213869A (ja) * | 2000-01-28 | 2001-08-07 | Nippon Bayer Agrochem Co Ltd | イソチアゾールカルボン酸誘導体および病害防除剤 |
JP2001294581A (ja) * | 2000-04-12 | 2001-10-23 | Nippon Bayer Agrochem Co Ltd | イソチアゾール誘導体 |
JP2003113167A (ja) * | 2001-10-05 | 2003-04-18 | Bayer Ag | イソチアゾール類および病害防除剤 |
JP2003146975A (ja) * | 2001-11-15 | 2003-05-21 | Bayer Ag | イソチアゾール類および病害防除剤 |
EP2070411A1 (en) | 2007-12-11 | 2009-06-17 | Bayer CropScience AG | Active compound combinations |
EP2070414A1 (en) | 2007-12-11 | 2009-06-17 | Bayer CropScience AG | Active compound combinations |
EP2070413A1 (en) | 2007-12-11 | 2009-06-17 | Bayer CropScience AG | Active compound combinations |
EP2070415A1 (en) | 2007-12-11 | 2009-06-17 | Bayer CropScience AG | Active compound combinations |
TWI489942B (zh) | 2008-12-19 | 2015-07-01 | Bayer Cropscience Ag | 活性化合物組合物 |
CN102361559B (zh) * | 2009-02-03 | 2013-11-06 | 拜尔农作物科学股份公司 | 含硫杂芳族酸类似物作为杀细菌剂的用途 |
BR112012006841B8 (pt) | 2009-10-15 | 2021-06-08 | Bayer Cropscience Ag | combinação de composto ativo, seus usos e método para curativamente ou preventivamente controlar os fungos fitopatogênicos e/ou microrganismos e/ou pragas de plantas ou safras |
US20150011394A1 (en) * | 2012-01-21 | 2015-01-08 | Bayer Intellectual Property Gmbh | Use of host defense inducers for controlling bacterial harmful organisms in useful plants |
JP5753632B2 (ja) * | 2012-10-05 | 2015-07-22 | イハラケミカル工業株式会社 | イソチアゾール化合物の製造方法 |
AR093996A1 (es) | 2012-12-18 | 2015-07-01 | Bayer Cropscience Ag | Combinaciones bactericidas y fungicidas binarias |
WO2017178407A1 (en) | 2016-04-13 | 2017-10-19 | Bayer Cropscience Aktiengesellschaft | Fungicidal combinations |
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DE1770976A1 (de) * | 1968-07-25 | 1972-01-13 | Bayer Ag | Isothiazolderivate und ein Verfahren zu ihrer Herstellung |
US4132676A (en) * | 1977-12-09 | 1979-01-02 | Givaudan Corporation | Perfume compositions containing ethyl 3,4-dichloro-5-isothiazolecarboxylate |
JP2530071B2 (ja) * | 1990-09-20 | 1996-09-04 | 三井東圧化学株式会社 | イソチアゾ―ルカルボン酸誘導体およびこれらを有効成分とするイネいもち病防除剤 |
US5240951A (en) * | 1990-09-20 | 1993-08-31 | Mitsui Toatsu Chemicals, Incorporated | Isothiazolecarboxylic acid derivatives, rice blast control agents containing the same as active ingredients, and rice blast control method applying the control agents |
JPH069313A (ja) | 1992-06-29 | 1994-01-18 | Mitsui Toatsu Chem Inc | イソチアゾールカルボン酸アニリド誘導体を有効成分とするイネいもち病防除剤 |
DE19545638A1 (de) * | 1995-12-07 | 1997-06-12 | Bayer Ag | Verwendung von 1,2,3-Thiadiazolcarbonsäure(thio)estern zur Bekämpfung von Schädlingen |
DE19642529A1 (de) * | 1996-10-15 | 1998-04-16 | Bayer Ag | Aminophenolderivate |
-
1997
- 1997-11-12 DE DE19750011A patent/DE19750011A1/de not_active Withdrawn
-
1998
- 1998-11-03 KR KR1020007004448A patent/KR100577614B1/ko not_active IP Right Cessation
- 1998-11-03 EP EP98959830A patent/EP1044195A1/de not_active Withdrawn
- 1998-11-03 WO PCT/EP1998/006960 patent/WO1999024414A1/de active IP Right Grant
- 1998-11-03 CN CN98811083.0A patent/CN1121399C/zh not_active Expired - Fee Related
- 1998-11-03 AU AU15591/99A patent/AU1559199A/en not_active Abandoned
- 1998-11-03 US US09/554,170 patent/US6191155B1/en not_active Expired - Fee Related
- 1998-11-03 PL PL98340461A patent/PL340461A1/xx unknown
- 1998-11-03 JP JP2000520428A patent/JP4511720B2/ja not_active Expired - Fee Related
- 1998-11-03 RU RU2000115289/04A patent/RU2205180C2/ru not_active IP Right Cessation
- 1998-11-03 BR BR9814134-1A patent/BR9814134A/pt not_active Application Discontinuation
- 1998-11-11 ZA ZA9810298A patent/ZA9810298B/xx unknown
- 1998-11-11 TW TW087118721A patent/TW502028B/zh not_active IP Right Cessation
- 1998-11-11 CO CO98066542A patent/CO5040010A1/es unknown
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102942565A (zh) * | 2012-11-06 | 2013-02-27 | 江西天人生态股份有限公司 | 一类3,4-二氯异噻唑衍生物及其制备方法和用途 |
CN102942565B (zh) * | 2012-11-06 | 2016-01-27 | 江西天人生态股份有限公司 | 一类3,4-二氯异噻唑衍生物及其制备方法和用途 |
CN108031305A (zh) * | 2017-12-23 | 2018-05-15 | 刘顶康 | 一种延长聚烯烃微滤膜抗菌持久性的方法 |
Also Published As
Publication number | Publication date |
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US6191155B1 (en) | 2001-02-20 |
WO1999024414A1 (de) | 1999-05-20 |
CO5040010A1 (es) | 2001-05-29 |
JP2001522841A (ja) | 2001-11-20 |
DE19750011A1 (de) | 1999-05-20 |
PL340461A1 (en) | 2001-02-12 |
CN1121399C (zh) | 2003-09-17 |
JP4511720B2 (ja) | 2010-07-28 |
KR20010024566A (ko) | 2001-03-26 |
AU1559199A (en) | 1999-05-31 |
EP1044195A1 (de) | 2000-10-18 |
KR100577614B1 (ko) | 2006-05-10 |
RU2205180C2 (ru) | 2003-05-27 |
TW502028B (en) | 2002-09-11 |
AR016008A1 (es) | 2001-05-30 |
ZA9810298B (en) | 1999-05-18 |
BR9814134A (pt) | 2000-10-03 |
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