CN1267419C - 用作杀菌剂的三氟甲基吡咯羧酰胺和三氟甲基吡咯乙硫异酰胺 - Google Patents

用作杀菌剂的三氟甲基吡咯羧酰胺和三氟甲基吡咯乙硫异酰胺 Download PDF

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CN1267419C
CN1267419C CNB008192340A CN00819234A CN1267419C CN 1267419 C CN1267419 C CN 1267419C CN B008192340 A CNB008192340 A CN B008192340A CN 00819234 A CN00819234 A CN 00819234A CN 1267419 C CN1267419 C CN 1267419C
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H·沃特尔
S·特拉
H·施奈德尔
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Abstract

通式(I)新型的吡咯衍生物，其中X为氧或硫；R1为氢、取代或未取代的C1-C4烷基或卤素；R2为取代或未取代的C1-C4烷基；且A为邻位取代的芳基；邻位取代的杂芳基；取代或未取代的双环芳基；或取代或未取代的双环杂芳基。该新型化合物具有植物保护性能，适合于保护植物免受植物致病微生物的感染。

Description

用作杀菌剂的三氟甲基吡咯羧酰 胺和三氟甲基吡咯乙硫异酰胺
本发明涉及具有杀微生物活性，特别是杀菌活性的新型三氟甲基吡咯羧酰胺或三氟甲基吡咯乙硫异酰胺。本发明也涉及这些物质的制备，含有至少一种该新型化合物作为活性成分的农用化学品组合物，上述组合物的制备以及所述活性成分或组合物在农业和园艺中用于控制或防止植物免受植物致病微生物，优选真菌感染的用途。
本发明的三氟甲基吡咯羧酰胺具有通式I：
Figure C0081923400061
其中
X为氧或硫；
R1为氢、取代或未取代的C1-C4烷基、取代或未取代的C1-C4烷氧基或卤素；
R2为取代或未取代的C1-C4烷基；
A为邻位取代的芳基；邻位取代的杂芳基；取代或未取代的双环芳基；或取代或未取代的双环杂芳基；
令人惊奇的是，现已发现通式I的化合物显示出改进的生物学特性，这使得它们更适合用于农业和园艺。
当通式1的化合物中存在不对称碳原子时，这些化合物具有光学活性形式。本发明涉及纯的异构体，如对映体和非对映体，以及所有可能的异构体混合物，如非对映体混合物、消旋体或消旋体的混合物。
在本说明书中，烷基表示甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基和叔丁基。优选非支链烷基。烷基作为其他基团的一部分，如烷氧基、卤代烷基、烷基环烷基、烷基环烷氧基等的一部分时具有类似的含义。卤素通常理解为意指氟、氯、溴或碘。其优选的含义为氟、氯或溴。卤素作为其他基团的一部分，如卤代烷基、卤代烷氧基、卤代烯基、卤代烯氧基、卤代芳基或卤代杂芳基等的一部分时具有类似的含义。卤代芳基或卤代杂芳基表示一到五个卤代的芳基，其中卤素独立地进行选择。当存在两个以上卤素时，卤素优选是相同的，如三氟苯基、三氯苯基、四氯苯基或全氯苯基。
芳基为苯基或萘基。
杂芳基将被理解为可能包含高达3个杂原子，如氮、氧或硫的5到10元环。以下列举的例子并非穷举：呋喃基、噻吩基、咪唑基、吡唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、噁二唑基、噻二唑基、三唑基、四唑基、吡咯基、二硫醇基(dithiolyl)、噁硫醇基(oxathiolyl)、二噁唑基、噁噻唑基、噁硫醇基(oxathiolyl)、吡啶基、哒嗪基、嘧啶基、吡嗪基、三嗪基、吲哚基、苯并呋喃基、苯并咪唑基、吲唑基、苯并三唑基、苯并噻唑基、苯并噁唑基、喹啉基、异喹啉基、酞嗪基、喹喔啉基、喹唑啉基、噌啉基、1，5-二氮杂萘基、异苯并呋喃基、异氮茚基、苯并噻二唑基、苯并噻吩基、苯并异噁唑基、嘌呤基、5，6-二氢-1，4，2-二噁嗪基等。
双环芳基或双环杂芳基将被理解为6元芳基或6元杂芳基，其中它可能包含高达3个杂原子，如氮、氧或硫，并且稠合到一个另外的环上。稠环可以是芳香的，部分氢化的或完全饱和的，可以是5到7元环，其中环中多至3个原子可以是选自氮、氧和硫的杂原子。以下列举的例子并非穷举：二氢异苯并呋喃基、二氢异吲哚基等。
通式I化合物的优选实施方案为这样的化合物：
其中
X为氧或硫；或
X为氧；或
X为硫；或
R1为氢、取代或未取代的C1-C4烷基、取代或未取代的C1-C4烷氧基或卤素；或
R1为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4卤代烷氧基-C1-C4烷基或卤素；或
R1为氢、C1-C4烷基或C1-C4卤代烷基；或
R1为氢或C1-C3烷基；或
R2为取代或未取代的C1-C4烷基；或
R2为C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基或C1-C4卤代烷氧基-C1-C4烷基；或
R2为C1-C4烷基、C1-C3卤代烷基或C1-C3烷氧基-C1-C3烷基；或
R2为C1-C3烷基或C1-C3烷氧基-C1-C3烷基；或
A为邻位取代的芳基；邻位取代的杂芳基；取代或未取代的双环芳基；或取代或未取代的双环杂芳基；或A为基团
Figure C0081923400081
或
A为A1、A2、A 3、A5、A8、A10、A13、A14、A17、A18、A20、A21、A22、A24、A25、A26、A27、A29、A31或A32；或
A为A1、A2、A3、A17、A20、A21、A24、A25、A26、A27或A31；或
R3为未取代的或被卤素、羟基、C1-C4烷氧基、C1-C4卤代烷基、C2-C4烯基、C2-C4炔基、C1-C4卤代烷氧基或C1-C4烷基进行一到三取代的C3-C7环烷基；未取代的或被卤素、羟基、C1-C4烷氧基、C1-C4卤代烷基、C2-C4烯基、C2-C4炔基、C1-C4卤代烷氧基或C1-C4烷基进行一到三取代的C4-C7环烯基；未取代的或被卤素、羟基、C1-C4烷氧基、C1-C4卤代烷基、C2-C4烯基、C2-C4炔基、C1-C4卤代烷氧基或C1-C4烷基进行一到三取代的C6-C7环二烯基；噻吩基、呋喃基、吡咯基、吡唑基、噁唑基、噻唑基、异噁唑基、异噻唑基、噻二唑基、咪唑基、四唑基、三嗪基、苯并噻吩基、5，6-二氢-1，4，2-二噁嗪基、吡啶基、吡嗪基、哒嗪基或嘧啶基，其为未取代的或被卤素、C1-C6卤代烷基、C1-C6烷基、羟基、氰基、硝基、CHO、C1-C4烷氧基-C1-C4烷基、COOC1-C4烷基、C1-C6卤代烷氧基-C1-C4烷基、C1-C6烷氧基或C1-C6卤代烷氧基取代；或
R3为未取代的或被卤素、羟基、C2-C4烯基、C2-C4炔基、C1-C3烷氧基或C1-C4烷基进行一到三取代的C5-C7环烷基；未取代的或被卤素、羟基、C1-C3烷氧基、C2-C4烯基、C2-C4炔基或C1-C4烷基进行一到三取代的C5-C7环烯基；未取代的或被卤素、羟基、C1-C3烷氧基、C2-C4烯基、C2-C4炔基或C1-C4烷基进行一到三取代的C6-C7环二烯基；噻吩基、呋喃基、噁唑基、异噁唑基、噻二唑基、三嗪基、吡啶基、吡嗪基，哒嗪基或嘧啶基，其为未取代的或被卤素、C1-C4卤代烷基、C1-C4烷基、羟基、C1-C4烷氧基或C1-C4卤代烷氧基进行一到三取代；或
R3为环己基、环己烯基或环己二烯基，其为未取代的或被氯、溴、C1-C2烷基、C1-C2卤代烷基或C1-C2卤代烷氧基进行一到二取代；噻吩基、呋喃基、三嗪基、吡啶基、吡嗪基、哒嗪基或嘧啶基，其为未取代的或被卤素、C1-C4烷基、C1-C4卤代烷基或C1-C4卤代烷氧基进行一到三取代；或
R31为未取代的或被卤素、C1-C6烷氧基、C1-C6烷氧基-C1-C6烷基、C1-C6卤代烷氧基-C1-C4烷基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C2-C4烯基或C2-C5炔基取代的C3-C7环烷基、C3-C7环烯基或C5-C7环烷二烯基；未取代的或被卤素、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C4烷基、C1-C4卤代烷基、C2-C4烯基、C2-C5炔基、CHO、COOC1-C4烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷基-C1-C4烷氧基、C1-C4卤代烷氧基-C1-C4烷基、C1-C4卤代烷基-C1-C4烷氧基、氰基或硝基取代的苯基；噻吩基、呋喃基、吡咯基、吡唑基、噁唑基、噻唑基、异噁唑基、异噻唑基、噻二唑基、咪唑基、三嗪基、吡啶基、哒嗪基、吡嗪基或嘧啶基，其为未取代的或被卤素、C1-C6卤代烷基、C1-C6烷基、羟基、氰基、硝基、CHO、COOC1-C4烷基、C1-C6卤代烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基、C1-C6烷氧基或C1-C6卤代烷氧基取代；或
R31为C5-C7环烷基、C5-C7环烯基或C5-C7环烷二烯基，其为未取代的或被卤素、C1-C4烷基、C1-C4烷氧基、C2-C4烯基、C2-C4炔基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；未取代的或被卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基取代的苯基；噻吩基、呋喃基、异噁唑基、噁唑基、噻二唑基、三嗪基、吡啶基、嘧啶基、吡嗪基或哒嗪基，其为未取代的或被卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；或
R31为环己基、环己烯基或环己二烯基，其为未取代的或被卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；噻吩基、呋喃基、三嗪基、吡啶基、吡嗪基、哒嗪基或嘧啶基，其为未取代的或被卤素、C1-C4烷基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；或
R4为氢、氰基、硝基、卤素、C1-C4烷氧基、C1-C4卤代烷基、C1-C4烷基、C1-C4烷氧基-C1-C4烷基、未取代的或被C1-C3烷基或C1-C3卤代烷基取代的C5-C7环烷基、C1-C4卤代烷氧基-C1-C4烷基或C1-C4卤代烷氧基；或
R4为氢、卤素、C1-C4烷氧基、C1-C4烷基、未取代的或被C1-C3烷基或C1-C3卤代烷基取代的C5-C7环烷基、C1-C4卤代烷基、或C1-C4卤代烷氧基；或
R4为氢、卤素、C1-C3烷氧基、C1-C3卤代烷基、C1-C3烷基、未取代的或被C1-C3烷基或C1-C3卤代烷基取代的C5-C7环烷基或C1-C3卤代烷氧基；或
R5、R6、R7、R8和R9相同或不同，并各自独立地为氢、卤素、C1-C4卤代烷基、C1-C4烷基、C1-C6卤代烷氧基-C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基-C1-C4烷基或C3-C7环烷基；或
R5、R6、R7和R8相同或不同，并各自独立地为氢、C1-C4卤代烷基、C1-C4烷基、C1-C4烷氧基或C1-C4卤代烷氧基；或
R5、R6、R7和R8相同或不同，并各自独立地为氢或C1-C3烷基。
在通式I的化合物中，优选的化合物是，其中：R1为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4卤代烷氧基-C1-C4烷基或卤素；
R2为C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基或C1-C4卤代烷氧基-C1-C4烷基；
A为如下的基团
和
R3为未取代的或由卤素、羟基、C1-C4烷氧基、C1-C4卤代烷基、C2-C4烯基、C2-C4炔基、C1-C4卤代烷氧基或C1-C4烷基进行一到三取代的C3-C7环烷基；未取代的或被卤素、羟基、C1-C4烷氧基、C1-C4卤代烷基、C2-C4烯基、C2-C4炔基、C1-C4卤代烷氧基或C1-C4烷基进行一到三取代的C4-C7环烯基；未取代的或被卤素、羟基、C1-C4烷氧基、C1-C4卤代烷基、C2-C4烯基、C2-C4炔基、C1-C4卤代烷氧基或C1-C4烷基进行一到三取代的C6-C7环二烯基；噻吩基、呋喃基、吡咯基、吡唑基、噁唑基、噻唑基、异噁唑基、异噻唑基、噻二唑基、咪唑基、四唑基、三嗪基、苯并噻吩基、5，6-二氢-1，4，2-二噁嗪基、吡啶基、吡嗪基、哒嗪基或嘧啶基，其为未取代的或被卤素、C1-C6卤代烷基、C1-C6烷基、羟基、氰基、硝基、CHO、C1-C4烷氧基-C1-C4烷基、COOC1-C4烷基、C1-C6卤代烷氧基-C1-C4烷基、C1-C6烷氧基或C1-C6卤代烷氧基取代；
R31为未取代的或被卤素、C1-C6烷氧基、C1-C6烷氧基-C1-C6烷基、C1-C6卤代烷氧基-C1-C4烷基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C2-C4烯基或C2-C5炔基取代的C3-C7环烷基、C3-C7环烯基或C5-C7环烷二烯基；未取代的或被卤素、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C4烷基、C1-C4卤代烷氧基、C2-C4烯基、C2-C5炔基、CHO、COOC1-C4烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷基-C1-C4烷氧基、C1-C4卤代烷氧基-C1-C4烷基、C1-C4卤代烷基-C1-C4烷氧基、氰基或硝基取代的苯基；噻吩基、呋喃基、吡咯基、吡唑基、噁唑基、噻唑基、异噁唑基、异噻唑基、噻二唑基、咪唑基、三嗪基、吡啶基、哒嗪基、吡嗪基或嘧啶基，其为未取代的或被卤素、C1-C6卤代烷基、C1-C6烷基、羟基、氰基、硝基、CHO、COOC1-C4烷基、C1-C6卤代烷氧基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基、C1-C6烷氧基或C1-C6卤代烷氧基取代；
R4为氢；氰基；硝基；卤素；C1-C4烷氧基；C1-C4卤代烷基；C1-C4烷基；C1-C4烷氧基-C1-C4烷基；未取代的或被C1-C3烷基或C1-C3卤代烷基取代的C5-C7环烷基；C1-C4卤代烷氧基-C1-C4烷基；或C1-C4卤代烷氧基；和
R5、R6、R7、R8和R9相同或不同，并各自独立地为氢、卤素、C1-C4卤代烷基、C1-C4烷基、C1-C6卤代烷氧基-C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基-C1-C4烷基或C3-C7环烷基(AA小组)
取决于环的大小，环烷基为环丙基、环丁基、环戊基、环己基或环庚基。
取决于环的大小，环烯基为环戊烯基、环己烯基或环庚烯基。
取决于环的大小，环烷二烯基为环戊二烯基、环己二烯基或环庚二烯基。
烯基将被理解为直链或支链烯基，如烯丙基、甲代烯丙基、丙烯基或丁-2-烯-1-基。优选的烯基在其链中含有3-4个碳原子。
根据碳原子数目，炔基同样可以为直链或支链的基团，一般地为炔丙基、丁-1-炔-1-基或丁-1-炔-3-基。
在通式I化合物的AA基团中，优选其中X为氧(AB小组)的化合物。
AA组内通式I的另一组化合物是那些其中X为硫的化合物(AC小组)。
在AB小组内的优选的化合物是：其中R1为氢、C1-C4烷基或C1-C4卤代烷基；
R2为C1-C4烷基、C1-C3卤代烷基或C1-C3烷氧基-C1-C3烷基；
A为A1、A2、A3、A5、A8、A10、A13、A14、A17、A18、A20、A21、A22、A24、A25、A26、A27、A29、A31或A32；
R3为未取代的或被卤素、羟基、C2-C4烯基、C2-C4炔基或C1-C3烷基或C1-C3烷氧基进行一到三取代的C5-C7环烷基；未取代的或被卤素、羟基、C2-C4烯基、C2-C4炔基或C1-C3烷基或C1-C3烷氧基进行一到三取代的C5-C7环烯基；未取代的或被卤素、羟基、C2-C4烯基、C2-C4炔基或C1-C3烷基或C1-C3烷氧基进行一到二取代的C6-C7环二烯基；噻吩基、呋喃基、异噁唑基、噁唑基、噻二唑基、三嗪基、吡啶基、嘧啶基、吡嗪基或哒嗪基，其为未取代的或被卤素、羟基、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；
R31为C5-C7环烷基、C5-C7环烯基或C5-C7环烷二烯基，其为未取代的或被卤素、C1-C4烷基、C1-C4烷氧基、C2-C4烯基、C2-C4炔基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；未取代的或被卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基取代的苯基；噻吩基、呋喃基、异噁唑基、噁唑基、噻二唑基、三嗪基、吡啶基、嘧啶基、吡嗪基或哒嗪基，其为未取代的或被卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；
R4为氢；卤素；C1-C4烷基；C1-C4烷氧基；未取代或被C1-C3烷基或C1-C3卤代烷基取代的C5-C7环烷基；C1-C4卤代烷基；或C1-C4卤代烷氧基；且
R5、R6、R7和R8相同或不同，并各自独立地为氢、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基(小组AB1)。
在AB1小组内更优选的化合物为：其中A为A1、A2、A3、A17、A20、A21、A24、A25、A26、A27或A31；
R为氢或C1-C3烷基；
R2为C1-C3烷基或C1-C3烷氧基-C1-C3烷基；
R3为环己基、环己烯基或环己二烯基，其为未取代的或被氯、溴、C1-C2烷基、C1-C2卤代烷基或C1-C2卤代烷氧基进行一到二取代；噻吩基、呋喃基、三嗪基、吡啶基、吡嗪基、哒嗪基或嘧啶基，其为未取代的或被卤素、C1-C4烷基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；
R31为环己基、环己烯基或环己二烯基，其为未取代的或被卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；噻吩基、呋喃基、三嗪基、吡啶基、吡嗪基、哒嗪基或嘧啶基，其为未取代的或被卤素、C1-C4烷基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；
R4为氢；卤素；C1-C3烷基；C1-C3卤代烷基；C1-C3烷氧基；未取代或被C1-C3烷基或C1-C3卤代烷基取代的C5-C7环烷基；或C1-C3卤代烷氧基；且
R5、R6、R7和R8相同或不同，并各自独立地为氢或C1-C3烷基(小组AB2)。
在AC小组内的优选的化合物是：其中
R1为氢、C1-C4烷基或C1-C4卤代烷基；
R2为C1-C4烷基、C1-C3卤代烷基或C1-C3烷氧基-C1-C3烷基；
A为A1、A2、A3、A5、A8、A10、A13、A14、A17、A18、A20、A21、A22、A24、A25、A26、A27、A29、A31或A32；
R3为未取代的或被卤素、羟基、C2-C4烯基、C2-C4炔基或C1-C3烷基或C1-C3烷氧基进行一到三取代的C5-C7环烷基；未取代的或被卤素、羟基、C2-C4烯基、C2-C4炔基或C1-C3烷基或C1-C3烷氧基进行一到三取代的C5-C7环烯基；未取代的或被卤素、羟基、C2-C4烯基、C2-C4炔基或C1-C3烷基或C1-C3烷氧基进行一到二取代的C6-C7环二烯基；噻吩基、呋喃基、异噁唑基、噁唑基、噻二唑基、三嗪基、吡啶基、嘧啶基、吡嗪基或哒嗪基，其为未取代的或被卤素、羟基、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；
R31为C5-C7环烷基、C5-C7环烯基或C5-C7环烷二烯基，其为未取代的或被卤素、C1-C4烷基、C1-C4烷氧基、C2-C4烯基、C2-C4炔基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；未取代的或被卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基取代的苯基；噻吩基、呋喃基、异噁唑基、噁唑基、噻二唑基、三嗪基、吡啶基、嘧啶基、吡嗪基或哒嗪基，其为未取代的或被卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；
R4为氢；卤素；C1-C4烷基；C1-C4烷氧基；C1-C4卤代烷基；未取代或被C1-C3烷基或C1-C3卤代烷基取代的C5-C7环烷基；或C1-C4卤代烷氧基；且
R5、R6、R7和R8相同或不同，并各自独立地为氢、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基(小组AC1)。
在AC1小组内更优选的化合物为，其中
A为A1、A2、A3、A17、A2O、A21、A24、A25、A26、A27或A31；R1为氢或C1-C3烷基；
R2为C1-C3烷基或C1-C3烷氧基-C1-C3烷基；
R3为环己基、环己烯基或环己二烯基，其为未取代的或被氯、溴、C1-C2烷基、C1-C2卤代烷基或C1-C2卤代烷氧基进行一到二取代；噻吩基、呋喃基、三嗪基、吡啶基、吡嗪基、哒嗪基或嘧啶基，其为未取代的或被卤素、C1-C4烷基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；
R31为环己基、环己烯基或环己二烯基，其为未取代的或被卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；噻吩基、呋喃基、三嗪基、吡啶基、吡嗪基、哒嗪基或嘧啶基，其为未取代的或被卤素、C1-C4烷基、C1-C4卤代烷基或C1-C4卤代烷氧基取代；
R4为氢；卤素；C1-C3烷基；C1-C3卤代烷基；C1-C3烷氧基；未取代或被C1-C3烷基或C1-C3卤代烷基取代的C5-C7环烷基；或C1-C3卤代烷氧基；且
R5、R6、R7和R8相同或不同，并各自独立地为氢或C1-C3烷基(小组AC2)。
在小组AB内优选的化合物为，其中
A为A1且
R3为未取代的或被C1-C4烷基或C1-C4卤代烷基单取代的C5-C7环烷基(小组AB3)。
个别的优选化合物为：
N-[2-(3-甲基环己基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺；
N-[2-(3-乙基环己基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺；
N-[2-(3-三氟甲基环己基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺；
N-[2-(3-甲基环戊基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺；
N-[2-(3-乙基环戊基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺；
N-[2-(3-三氟甲基环戊基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺。
符合通式I的化合物可根据以下反应方案制备。
A)吡咯羧酸的合成：
路线1(Tosmic-路线)
方案1
路线2(三氟乙酰乙酸路线，类似于日本专利JP-07157466)
方案2
碱1＝NaHCO3，NaCO3，KHCO3，CaCO3和其他碱
碱2＝NaOH，KOH，NaH，KH，n-BuLi等
B)酰胺/硫代酰胺的合成
方案3
Figure C0081923400182
碱＝NEt3，Hūnig-碱，Na2CO3，K2CO3等
B1)酰胺的合成，其中A为苯基、吡啶或嘧啶基
方案4
Figure C0081923400183
G＝苯基、吡啶基、嘧啶基
“原位”制备的吡唑羧酸氯化物在溶剂，如甲苯、苯、二甲苯、己烷、环己烷、THF、氯仿或二氯甲烷和碱，如碳酸钠、碳酸氢钠、碳酸钾、Hünig碱、三乙胺或吡啶的存在下，在0℃-回流温度下与邻卤取代的苯胺反应。得到的吡唑羧酰胺在Pd催化剂和碱的存在下，在一种溶剂中与通式为R3-B(OH)2的硼酸反应，所述Pd催化剂为，如Pd(P(ph)3)4，Pd(P(ph)3)2Cl2，PdCl2dppb，Pd2(dba)3，Pd(OAc)2，PdOAc2/(邻甲苯基)3P，Pd(OAc)2/dppf，Pd(PhCN)2Cl2/Ph3As，Pd(CH3CN)2Cl2，Pd2(dba)3/P(叔丁基)3，Pd(OAc)2/P(叔丁基)2联苯，Pd(OAc)2/TPPTS，Pd(OAc)2/PCy3，Pd(OAc)2/P(氧异丙基)3，Pd(OAc)2/2-二甲基氨基-2′-二环己基膦联苯，Pd(OAc)2/2-二甲基氨基-2′-二叔丁基膦联苯，Pd(OAc)2/(邻联苯基)P(环己基)2，所述溶剂为，如1，2-二甲氧基乙烷/水，DMF，DMA，THF/水，二氧六环/水，苯，甲苯，二甲苯等，所述碱为如碳酸钠，碳酸氢钠，碳酸钾，碳酸铯，磷酸钾，三乙胺，氢氧化钠，乙基钠，叔丁醇钠，氧化银，碳酸钡，氟化钾或氟化铯，反应温度为0℃-回流温度。
C)邻取代胺A-NH2的合成：
该类化合物或者是文献中公知的，或者可以用公知的方法制备。
例如，以下用于胺合成中的胺或重要中间体可以根据以下文献制备：
A1-NH2：Tetrahedron  1993，49，49-64，或EP-83975，或J.Org.Chem.，1995， 60，292；
A2-NH2：EP-737682；
A3-NH2：J.Chem.Res.(S)， 1978，11，428，或Chem.Scr.， 1972，2,245；
A17-NH2：Org.Prep.Procedures Int.， 1989，21，141；
A21-NH2：J.Chem.Soc.Perkin I， 1981，5，1591；
A25-NH2：Tetrohedron， 1993，49，49-64，或Heterocycles， 1999，51，721；
A26-NH2：Synthesis，1996，10，1015或Synthesis，1994，9，931；
A27-NH2：Liebigs Ann.Chemie，1977，537-544，或J.Med.Chem.，1975，18，623；
A31-NH2：EP-315502；
A32-NH2：J.Pesticide Science， 1993，18，245；
A30-NH2：J.Heterocyclic Chem.， 1982，19，1285。
令人惊奇的是现在已经发现，实际上具有通式I的新型化合物具有非常有益的广谱活性，用于保护植物免受真菌以及细菌和病毒引起的病害。
通式I的化合物可被用于农业部门和相关的领域，用作控制植物害虫的活性成分。该新型化合物的特点是在低施用率下优异的活性，良好的植物耐受性和环境安全性。它们具有非常有效的治病、预防和系统性能并可用于保护众多的栽培植物。通式I的化合物可用于抑制或破坏有益植物中不同作物的植物或植物局部(果实、花、叶子、茎、块茎、根)出现的害虫，与此同时还保护那些随后生长的植物部分免受植物致病微生物的侵害。
还可以使用通式I的化合物作为处理植物繁殖物质的修饰剂，尤其是种籽(果实、块茎、谷类)和植物插枝(如稻)，用于防止真菌传染以及防止土壤中存在的植物致病真菌。
化合物I对于以下种类的植物致病真菌有效：半知菌类(如葡萄孢属，Pyricularia，长蠕孢属，镰刀菌属，壳针孢属，尾孢属和链格孢属)和担子菌类(如丝核菌属，驼孢锈属，柄锈菌属)。另外，它们还对子囊菌类(如黑星菌属和白粉菌属，柄球菌属，Monifinia，钩丝壳属)和卵菌类(如疫霉属，腐霉属，单轴霉属)有效。已经注意到它们对于白粉菌(白粉菌属)具有突出的活性。而且，通式I的新型化合物对于植物致病细菌和病毒也是有效的(如黄单孢菌属，假单胞菌属，解淀粉欧文氏杆菌以及烟草花叶病毒)。
在本发明范围内，要保护的目标农作物一般包括以下植物物种：谷类(小麦、大麦、黑麦，燕麦、稻、玉米、高粱和相关的物种)；甜菜(糖用甜菜和饲用甜菜)；梨果、核果和软果(苹果、梨、李子、桃子、杏仁、樱桃、草莓、木莓和黑莓)；豆类植物(菜豆、小扁豆、豌豆、大豆)；油料植物(油菜、芥末、罂粟、橄榄、葵花、椰子、蓖麻、可可豆、落花生)；瓜类植物(南瓜、黄瓜、甜瓜)；纤维植物(棉花、亚麻、大麻、黄麻)；柑桔类水果(橙子、柠檬、葡萄柚、桔)；蔬菜(菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、番茄、马铃薯、红辣椒)；樟科(鳄梨、中国内桂、樟树)或如烟草、坚果、咖啡、茄子、甘蔗、茶、胡椒、葡萄、蛇麻子、香蕉的植物和天然橡胶植物以及观赏植物。
通式I化合物以来改性的形式使用，优选，与通常用于制剂领域的助剂一起使用。为此，它们可以以公知的方式方便地配制成浓缩乳剂、可涂覆的糊状物、可直接喷雾的或可稀释的溶液、稀释的乳液、可湿性粉剂、可溶性粉剂、粉剂、颗粒以及如用聚合物封装的胶囊。对于这种类型的组合物，根据预定的目标和当地的情况选择使用如下的施用方法，如喷雾、雾化、粉化、分散、涂布或倾注。组合物也可以包含另外的助剂，如稳定剂、消泡剂、粘度调节剂、粘合剂或增粘剂以及化肥、微量营养素供体或其它用于得到特殊效果的制剂。
适合的载体和助剂可以是固体或液体，并且是对配制技术有用的物质，如天然或再生的矿物质、溶剂、分散剂、润湿剂、增粘剂、增稠剂、粘合剂或化肥。这种载体的例子描述于WO 97/33890中。
通式I的化合物通常以组合物的形式使用，可以与另外的化合物同时或连续应用于要处理的作物区域或植物上。这些另外的化合物可以是，如化肥或微量营养素供体或其它的影响植物生长的制剂。它们还可能是选择性除草剂以及杀虫剂、杀真菌剂、杀菌剂、杀线虫剂、杀螺剂或所述几种制剂的混合物，如果需要，可以与通常用于制剂领域的另外的载体、表面活性剂或施用促进助剂一起使用。
通式I的化合物可以与其它的杀真菌剂混合，使得在某些情况下产生了料想不到的协同活性。
特别优选的混合组分是吡咯，如戊环唑、双苯三唑醇，丙环唑、噁醚唑、烯唑醇、环唑醇、氧唑菌、喹唑菌酮、氟硅唑、粉唑醇、己唑醇、烯菌灵、酰胺唑、环戊唑醇、戊唑醇、氟醚唑、腈苯唑、环戊唑菌、腈菌唑、perfurazoate、戊菌唑、糠菌唑、啶斑肟、丙氯灵、三唑酮、唑菌醇、氟菌唑或戊叉唑菌；嘧啶基甲醇类，如嘧啶醇、异嘧菌或氯苯嘧啶醇；2-氨基嘧啶，如磺嘧菌灵、甲菌定或乙菌定；吗啉，如吗菌灵、苯锈啶、丁苯吗啉、螺噁茂胺或克啉菌；苯胺基嘧啶，如环丙嘧啶、二甲嘧菌胺或嘧菌胺；吡咯，如拌种咯或氟噁菌；苯基酰胺，如苯霜灵、呋氨丙灵、甲霜灵、R-甲霜灵、甲呋酰胺或噁霜灵；苯并咪唑，如苯菌灵、多菌灵、双乙氧咪唑威、麦穗宁或涕必灵；二甲酰亚胺，如乙菌利、菌核利、异菌脲、甲菌利、杀菌利或烯菌酮；羧酰胺，如萎锈灵、呋菌胺、氟酰胺、甲氧灭绣胺、氧化萎锈灵或溴氟唑菌；胍，如双辛胍醋酸盐、多果定或双胍辛醋酸盐；亚胺菌，如腈嘧菌酯、亚菌胺、叉氨苯酰、SSF-129、甲基2-[(2-三氟甲基)-嘧啶-6-基氧甲基]-3-甲氧基丙烯酸酯或2-[α-{[(α-甲基-3-三氟甲基-苯甲基)亚氨基]-氧)-邻甲苯基]-乙醛酸-甲酯-0-甲基肟(氟吗啉肟菌酯)；二硫代氨基甲酸盐，如福美铁、代森锰锌、代森锰、代森联、甲基代森锌、福美双、代森锌或福美锌；N-卤代甲基硫-二甲酰亚胺，如敌菌丹、克菌丹、抑菌灵、氟菌胺、灭菌丹或对甲抑菌灵；铜化合物，如波尔多液、氢氧化铜、王铜、硫酸铜、一氧化二铜、锰铜混剂或喹啉铜；硝基酚衍生物，如敌螨普或异丙消；有机磷衍生物，如克瘟散、异稻瘟净、稻瘟灵、双氯苯磷、定菌磷或甲基立枯磷；及其他不同结构的化合物，如噻二唑素、敌菌灵、灭瘟素、灭螨猛、地茂散、百菌清、清菌脲、二氯萘醌、哒菌清、氯硝胺、乙霉威、烯酰吗啉、二噻农、氯唑灵、噁唑酮菌、咪唑菌酮、三苯锡基、嘧菌腙、氟啶胺、磺菌胺、环酰菌胺、藻菌磷、土菌消、春雷霉素、磺菌威、戊菌隆、四氯苯酞、多氧霉素、噻菌灵、百维灵、咯喹酮、喹氧灵、五氯硝基苯、硫、唑菌嗪、三环唑、嗪氨灵、有效霉素、(S)-5-甲基-2-甲硫基-5-苯基-3-苯基氨基-3，5-二氢咪唑-4-酮(RPA 407213)、3，5-二氯-N-(3-氯-1-乙基-1-甲基-2-氧丙基)-4-甲基苯酰胺(RH-7281)、N-烯丙基-4，5-二甲基-2-三甲基甲硅烷基噻吩-3-羧酰胺(MON 65500)、4-氯-4-氰基-N，N-二甲基-5-对-甲苯基咪唑-1-磺酰胺(IKF 916)、N-(1-氰基-1，2-二甲丙基)-2-(2，4-二氯苯氧基)丙酰胺(AC 382042)、或iprovalicarb(SZX 722)。
通式I化合物或含有至少一种所述化合物的农用化学品组合物的优选施用方法是叶敷。施用频率和施用速率取决于被相应的病原体感染危险程度。但是，通式I的化合物也可以通过用液剂浸润植物所在位置经由土壤通过根而渗入植物中(整体作用)，或通过将固态的化合物如以颗粒形施用到土壤中(土壤施药)。在水稻农作物中，这类颗粒可以被施用到漫灌稻田中。通式I的化合物也可以通过用杀真菌剂的液剂浸透种子或决茎或者用固体制剂进行涂层而施用于种子。
可以公知的的方式制备制剂，即含有通式I化合物和，如果需要的话，固体或液体助剂的组合物，通常通过将该化合物与补充剂，如溶剂、固体载体和任选地，表面活性的化合物(表面活性剂)一起紧密混合和/或磨碎来制备。
农用化学品制剂通常含有0.1-99wt％，优选0.1-95wt％的通式I的化合物，99.9-1wt％，优选99.8-5wt％的固体或液体助剂，和0-25wt％，优选0.1-25wt％的表面活性剂。有利的施用速率通常是5克-2公斤活性成分(a.i.)每公顷(ha)，优选10克-1公斤a.i./ha，最优选20克-600克a.i./ha。当用作浸润种子的试剂时，适当的剂量是10毫克-1克活性物质每公斤种子。
尽管优选将市售产品配制成浓缩物，但最终用户通常使用稀释的制剂。
以下非限制性实施例更详细地说明上面描述的本发明。
给出的温度是摄氏温度。使用以下的缩写：
m.p.＝熔点；b.p.＝沸点；“NMR”意指核磁共振光谱；MS代表质谱；“％”是重量百分数，除非以其它单位指出相应的浓度。
实施例1：1-甲基-4-三氟甲基-1H-吡咯-3-羧酸[4-(4′-氯苯基)-吡啶-3-基]酰胺
a)1-甲基-4-三氟甲基吡咯-3-羧酸
Figure C0081923400231
在+5℃下，将氢化钠(8.0克分散于油中形成的75％的分散液)悬浮于二甲亚砜(300毫升)和二乙醚(100毫升)的混合物中。通过滴液漏斗加入4，4，4-三氯巴豆酸乙基酯(20克)和TOSMIC(23克)的二甲亚砜(100毫升)溶液，滴加速率使得温度不超过10℃。在室温下将反应混合物再搅拌1小时后，冷却下加入甲基碘(15.6毫升)。室温下2小时后，将反应混合物倾到碎冰上。用醚进行反复萃取，用盐水洗涤合并的有机相，在减压下蒸发溶剂，得到亮琥珀油状产品混合物。将粗产物混合物在乙醇(100毫升)和氢氧化钠(50毫升的30％水溶液)的混合物中在60℃下加热。用醚洗涤溶液，用浓盐酸酸化水相，过滤得到结晶固体状的1-甲基-4-三氟甲基吡咯-3-羧酸。
1H-NMR(CDCl3)：7.24(d，1H)；6.88(d，1H)；3.63(s，3H)。
以类似的方法可以制备1-乙基-4-三氟甲基吡咯-3-羧酸(m.p.146-148C)和1-甲氧基甲基-4-三氟甲基吡咯-3-羧酸。
b)4-(4′-氯苯基)-3-硝基吡啶
Figure C0081923400241
在一个磺化瓶中，将6.9克(44mmol)的4-氯-3-硝基吡啶，6.5克(42mmol)的4-氯苯基硼酸，6.0克(44mmol)碳酸钾(饱和水溶液)和1.0克(0.9mmol)四(三苯基膦)钯溶于100毫升二甲氧基乙烷(DME)中。在恒定的氮气流下，将混合物加热回流5小时。然后，在水喷真空下除去溶剂，剩余物溶于乙酸乙酯中。有机相用水洗涤两次，用硫酸钠干燥有机相后，在水喷真空下除去溶剂。所得粗产物通过硅胶柱色谱纯化(洗脱液：己烷/乙酸乙酯＝1∶1)。产量：8.9克4-(4′-氯苯基)-3-硝基吡啶，微褐色晶体；m.p.74-76℃。
c)3-氨基-4-(4′-氯苯基)吡啶
Figure C0081923400242
在一个磺化烧瓶中，将8.4克(36mmol)的4-(4′-氯苯基)-3-硝基吡啶溶于100毫升水、35毫升乙酸和10毫升正丙醇的混合物中。加入7.0克(125mmol)铁粉后，将混合物在回流条件下加热3小时。冷却到室温后，用乙酸乙酯稀释混合物，并通过hyflo过滤。加入重碳酸钠溶液中和滤液，分离有机相。水相用乙酸乙酯萃取两次，合并有机相，用硫酸钠干燥。在水喷真空下蒸馏去除溶剂后，得到的原料用硅胶柱色谱纯化(洗脱液：乙酸乙酯)。产量：3.9克3-氨基-4-(4′-氯苯基)吡啶，微褐色粉末；m.p.：144-146℃。
d)N-[4-(4-氯苯基)-吡啶-3-基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺
在催化量DMF存在的情况下，将0.54克(2.8mmol)的1-甲基-4-三氟甲基吡咯-3-羧酸和0.39克(3.1mmol)草酰氯的20毫升二氯甲烷溶液在室温下搅拌2小时。然后，将酰基氯溶液缓慢加入到0.57克(2.8mmol)的3-氨基-4-(4′-氯苯基)吡啶、0.34克(3.4mmol)三乙胺和15毫升二氯甲烷溶液中。然后将所得混合物在室温下搅拌16小时。加入乙酸乙酯后，有机相用水洗涤两次。经硫酸钠干燥有机相后，在水喷真空下除去溶剂。得到的粗产物通过硅胶柱色谱纯化(洗脱液：己烷/四氢呋喃＝1∶3)。产量：0.4克的N-[4-(4-氯苯基)-吡啶-3-基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺，淡黄晶体；m.p.：178-180℃。
实施例2：N-(2-溴-苯基)-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺
在催化量DMF存在的情况下，将7.8克(40.4mmol)的1-甲基-4-三氟甲基吡咯-3-羧酸和3.8毫升(45mmol)草酰氯的100毫升二氯甲烷溶液在室温下搅拌1小时。然后，将所得酰基氯溶液缓慢加入到6.95克(40.4mmol)的2-溴苯胺、6.9毫升(49mmol)三乙胺和140毫升二氯甲烷的溶液中。然后将所得混合物在室温下搅拌16小时。有机相用水洗涤两次，用硫酸钠干燥。在减压下除去溶剂。粗产品通过硅胶柱色谱纯化(洗脱液：乙酸乙酯/己烷＝2∶3)。产量：11.4克N-(2-溴-苯基)-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺，无色晶体；m.p.117-119℃。实施例3：N-[2-(5-氯噻吩基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺
Figure C0081923400261
在1.0克(2.9mmol)的1-甲基-4-三氟甲基-1H-吡咯-3-羧酸(2-溴苯酰胺)、0.56克(3.5mmol)的5-氯噻吩-2-硼酸和0.12克(0.2mmol)双(三苯基膦)氯化钯(II)的20毫升乙二醇二甲醚溶液中，加入0.87克(10.4mmol)碳酸氢钠的20毫升水溶液。然后反应混合物在70℃下搅拌24小时，加入二氯甲烷后，有机相用水和氯化钠溶液洗涤两次。硫酸钠干燥后，在减压下除去溶剂。产物通过硅胶柱色谱纯化(洗脱液：二氯甲烷/己烷＝4/1)。得到N-(2-溴-苯基)-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺，无色晶体；m.p.139-141℃。
以类似的方式，使用类似的方法制备以下的化合物。
表1：通式I的化合物，其中A＝A1＝
化合物        R1       R2        X        R3              R4        物理数据
序号                                                                     [熔点°C]
1.1           H         CH3       O        
Figure C0081923400272
        H
1.2           H         CH3       O                 H
1.3           H         CH3       O                 H
1.4           H         CH3       O        
Figure C0081923400275
        H
1.5           H         CH3       O        
Figure C0081923400276
        H
1.6           H         CH3       O        
Figure C0081923400277
        H
1.7           H         CH3       O        
Figure C0081923400278
         H
1.8           H         CH3       O               H
1.9           H         CH3       O        
Figure C00819234002710
      H
1.10          H         CH3       O        
Figure C00819234002711
      H
1.11          H         CH3       O              H        127-129
1.12          H         CH2CH3   O         
Figure C00819234002713
    H
1.13          H         CH3       S        
Figure C00819234002714
   H
1.14        H            CH3        O      
Figure C0081923400281
  H
1.15        H            CH3        O      
Figure C0081923400282
 H    131-132
1.16        H            CH3        S         H    resin
1.17        CH3         CH3        O      
Figure C0081923400284
      H
1.18        H            CH2OCH3   O      
Figure C0081923400285
  H
1.19        H            CH3        O      
Figure C0081923400286
        H    116-118
1.20        H            CH3        O            H    139-141
1.21        H            CH3        O              H    132-136
1.22        H            CH3        O              H
1.23        H            CH3        O               H    106-109
1.24        H            CH3        O      
Figure C00819234002811
        H    182-185
1.25        H            CH2OCH3   O      
Figure C00819234002812
        H    171-173
1.26        H            CH3        O      
Figure C00819234002813
        H    132-134
1.27        H            CH2OCH3   O              H
1.28        H            CH3        O      
Figure C00819234002815
       H
1.29        H            CH3        O               H
1.30        H        CH3        O            H
1.31        H        CH3        O           H
1.32        H        CH3        O     
Figure C0081923400293
     H
1.33        H        CH3        O     
Figure C0081923400294
     H
1.34        H        CH2CH3    O     
Figure C0081923400295
    H
1.35        H        CH2OCH3   O          H
1.36        H        CH3        O     
Figure C0081923400297
     H
1.37        H        CH3        O     
Figure C0081923400298
    H
1.38        H        CH3        O     
Figure C0081923400299
H
1.39        H        CH3        O     
Figure C00819234002910
     H
1.40        H        CH3        O     
Figure C00819234002911
     H        169-171
1.41        H        CH2OCH3   O           H
1.42        H        CH3        O           H        143-145
1.43        H        CH3        S     
Figure C00819234002914
     H
1.44        H        CH3        O     
Figure C00819234002915
     H
1.45        H        CH3        O      
Figure C0081923400301
     H
1.46        H        CH2OCH3   O            H
1.47        H        CH3        O      
Figure C0081923400303
     H
1.48        H        CH3        O            H
1.49        H        CH3        O      
Figure C0081923400305
     H        ＞230
1.50        H        CH2OCH3   O            H        ＞230
1.51        H        CH3        O      
Figure C0081923400307
     H
1.52        H        CH3        O      
Figure C0081923400308
     H
1.53        H        CH3        O      
Figure C0081923400309
     H
1.54        H        CH3        O      
Figure C00819234003010
     H
1.55        H        CH3        O      
Figure C00819234003011
     H
1.56        H        CH3        O      
Figure C00819234003012
  H
1.57        H        CH3        O      
Figure C00819234003013
     H
1.58        H        CH3        O            H
1.59        H        CH2CH3    O      
Figure C00819234003015
    H
1.60        H        CH3        O               H
1.61        H        CH3        O    
Figure C0081923400312
        H
1.62        H        CH3        O    
Figure C0081923400313
        H
1.63        H        CH3        O    
Figure C0081923400314
       H
1.64        H        CH3        O          H
1.65        CH3     CH3        O    
Figure C0081923400316
     H
1.66        H        CH3        O    
Figure C0081923400317
      H        126-128
1.67        H        CH3        O    
Figure C0081923400318
        H        164-165
1.68        H        CH3        O    
Figure C0081923400319
       H        118-119
1.69        H        CH2OCH3   O    
Figure C00819234003110
     H        油状物；
                                                               1H-NMRMS
1.70        H        CH3        O    
Figure C00819234003111
    H
1.71        H        CH2OCH3   O            H
1.72        H        CH3        O           H
1.73        H        CH2OCH3   O           H
1.74        H        CH3        O          H         93-95
1.75        H        CH2OCH3   O          H         油状物；
                                                                1H-NMR，MS
1.76        H        CH3        O            H
1.77H        CH2OCH3   O        
Figure C0081923400321
         H
1.78H        CH3        O                 H
1.79H        CH2OCH3   O                 H
1.80H        CH3        O         
Figure C0081923400324
       H
1.81H        CH3        O                H         250-252
1.82H        CH3        O         
Figure C0081923400326
      H         202-204
表2：通式I的化合物，其中A＝A2＝
化合物        R1       R2        X        R3              R4       物理数据
序号                                                                    [熔点℃]
2.1           H         CH3       O        
Figure C0081923400328
        H
2.2           H         CH3       O                 H
2.3           H         CH3       O                 H
2.4           H         CH3       O        
Figure C00819234003211
        H
2.5           H         CH3       O        
Figure C00819234003212
        H
2.6           H         CH2OCH3  O                 H
2.7         H       CH3        O      
Figure C0081923400331
      H
2.8         H       CH3        O              H
2.9         H       CH3        O      
Figure C0081923400333
    H
2.10        H       CH3        O      
Figure C0081923400334
    H
2.11        H       CH3        O      
Figure C0081923400335
    H
2.12        H       CH3        O      
Figure C0081923400336
  H        树脂
2.13        H       CH3        S         H
2.14        H       CH3        O      
Figure C0081923400338
  H
2.15        H       CH3        S      
Figure C0081923400339
  H
2.16        H       CH3        O          H
2.17        CH3    CH3        O              H
2.18        H       CH2OCH3   O      
Figure C00819234003312
  H
2.19        H       CH3        O      
Figure C00819234003313
         H
2.20        H       CH3        O      
Figure C00819234003314
      H
2.21        H       CH3        O      
Figure C00819234003315
         H
2.21        H        CH3        O      
Figure C0081923400341
      H
2.22        H        CH3        O      
Figure C0081923400342
       H
2.23        H        CH3        O               H       树脂
2.24        H        CH2OCH3   O              H
2.25        H        CH3        O              H
2.26        H        CH2OCH3   O      
Figure C0081923400346
       H
2.27        H        CH3        O      
Figure C0081923400347
       H
2.28        H        CH3        O              H
2.29        H        CH3        O      
Figure C0081923400349
       H
2.30        H        CH3        O      
Figure C00819234003410
      H
2.31        H        CH3        O             H
2.32        CH3     CH3        O      
Figure C00819234003412
      H
2.33        H        CH3        O      
Figure C00819234003413
      H
2.34        H        CH2CH3    O            H
2.35        H        CH2OCH3   O            H
2.36        H        CH3        O      
Figure C00819234003416
      H
2.37        H        CH3        O             H
2.38        H        CH3        O           H
2.39        H        CH3        O              H
2.40        H        CH3        O      
Figure C0081923400354
       H        树脂
2.41        H        CH2OCH3   O              H
2.42        H        CH3        O      
Figure C0081923400356
       H
2.43        H        CH3        S      
Figure C0081923400357
       H
2.44        H        CH3        O      
Figure C0081923400358
       H
2.45        H        CH3        O              H
2.46        H        CH2OCH3   O      
Figure C00819234003510
       H
2.47        H        CH3        O      
Figure C00819234003511
       H
2.48        H        CH3        O      
Figure C00819234003512
       H
2.49        H        CH3        O             H        ＞235
2.50        H        CH2OCH3   O              H
2.51        H        CH3        O              H
2.52        H        CH3        O        
Figure C0081923400361
      H
2.53        H        CH2CH3    O        
Figure C0081923400362
      H
2.54        H        CH3        O        
Figure C0081923400363
         H
2.55        H        CH3        O                  H
2.56        H        CH3        O        
Figure C0081923400365
         H
2.57        CH3     CH3        O                  H
2.58        H        CH3        O        
Figure C0081923400367
         H
2.59        H        CH3        O        
Figure C0081923400368
         H
2.60        H        CH3        O                  H
2.61        H        CH2CH3    O                 H
2.62        H        CH3        O                    H
2.63        H        CH3        O        
Figure C00819234003612
         H
2.64        H        CH3        O        
Figure C00819234003613
         H
2.65        H        CH3        O        
Figure C00819234003614
        H
2.66        H        CH3        O               H
2.67        CH3     CH3        O        
Figure C00819234003616
      H
表3：通式I的化合物，其中A＝A17＝
化合物        R1       R2        X        Rat                   R4       物理数据
序号                                                                          [熔点℃]
3.1           H         CH3       O        
Figure C0081923400372
              H
3.2           H         CH3       O                       H
3.3           H         CH3       O        
Figure C0081923400374
         H
3.4           H         CH3       O                  H
3.5           H         CH2OCH3  O        
Figure C0081923400376
         H
3.6           H         CH3       O        
Figure C0081923400377
         H
3.7           H         CH3       O                      H
3.8           H         CH3       O        
Figure C0081923400379
               H
3.9           H         CH3       O        
Figure C00819234003710
              H
3.10          H         CH3       O        
Figure C00819234003711
           H
3.11          H         CH2CH3   O                    H
3.12        H        CH3        O      
Figure C0081923400381
  H
3.13        H        CH3        O           H
3.14        H        CH3        O      
Figure C0081923400383
     H
3.15        H        CH3        O            H
3.16        H        CH3        O      
Figure C0081923400385
     H
3.17        H        CH3        O             H
3.18        H        CH3        O      
Figure C0081923400387
   H
3.19        H        CH3        O      
Figure C0081923400388
      H
3.20        H        CH3        O              H
3.21        H        CH3        O              H
3.22        H        CH3        O             H
3.23        CH3     CH3        O             H
3.24        H        CH3        O              H
3.25        H        CH3        S              H
表4：通式I的化合物，其中A＝A21＝
化合物        R1       R2        X        R31               物理数据
序号                                                           [熔点℃]
4.1           H         CH3       O        
4.2           H         CH3       O        
4.3           H         CH3       O        
Figure C0081923400394
4.4           H         CH3       O        
Figure C0081923400395
4.5           H         CH2OCH3  O        
4.6           H         CH3       O        
4.7           H         CH3       O        
Figure C0081923400398
4.8           H         CH3       O        
Figure C0081923400399
4.9           H         CH3       O        
4.10          H         CH3       O        
Figure C00819234003911
          树脂
4.11          H         CH2CH3   O        
Figure C00819234003912
4.12          H         CH3       O        
Figure C00819234003913
4.13        H        CH3        O       
Figure C0081923400401
4.14        H        CH3        O       
4.15        H        CH3        O       
4.16        H        CH3        O       
4.17        H        CH3        O       
4.18        H        CH3        O       
Figure C0081923400406
4.19        H        CH3        O       
Figure C0081923400407
4.20        H        CH3        O       
Figure C0081923400408
4.21        H        CH3        O       
4.22        H        CH3        O       
Figure C00819234004010
4.23        CH3     CH3        O       
Figure C00819234004011
4.24        H        CH3        O       
Figure C00819234004012
4.25        H        CH3        S       
Figure C00819234004013
表5：通式I的化合物，其中A＝A24＝
Figure C0081923400411
化合物        R1       R2        X        R31                 R4      物理数据
序号                                                                       [熔点℃]
5.1           H         CH3       O                     H
5.2           H         CH3       O        
Figure C0081923400413
            H
5.3           H         CH3       O        
Figure C0081923400414
       H
5.4           H         CH3       O                H
5.5           H         CH2OCH3  O        
Figure C0081923400416
       H
5.6           H         CH3       O                 H
5.7           H         CH3       O                    H
5.8           H         CH3       O                      H
5.9           H         CH3       O        
Figure C00819234004110
            H
5.10          H         CH3       O        
Figure C00819234004111
         H
5.11          H         CH2CH3   O        
Figure C00819234004112
         H
5.12          H         CH3       O                   H        树脂
5.13        H        CH3        O             H
5.14        H        CH3        O      
Figure C0081923400422
      H
5.15        H        CH3        O             H
5.16        H        CH3        O             H
5.17        H        CH3        O              H
5.18        H        CH3        O            H
5.19        H        CH3        O               H
5.20        H        CH3        O      
Figure C0081923400428
        H
5.21        H        CH3        O      
Figure C0081923400429
        H
5.22        H        CH3        O              H
5.23        CH3     CH3        O              H
5.24        H        CH3        O               H
5.25        H        CH3        S      
Figure C00819234004213
        H
表6：通式I的化合物，其中A＝A25＝
Figure C0081923400431
化合物        R1       R2        X        R31                 R4        物理数据
序号                                                                         [熔点℃]
6.1           H         CH3       O        
Figure C0081923400432
             H
6.2           H         CH3       O        
Figure C0081923400433
             H
6.3           H         CH3       O        
Figure C0081923400434
        H
6.4           H         CH3       O        
Figure C0081923400435
        H
6.5           H         CH2OCH3  O                 H
6.6           H         CH3       O        
Figure C0081923400437
         H
6.7           H         CH3       O        
Figure C0081923400438
            H
6.8           H         CH3       O                       H
6.9           H         CH3       O        
Figure C00819234004310
             H
6.10          H         CH3       O        
Figure C00819234004311
          H           178-180
6.11          H         CH2CH3   O                   H
8.12          H         CH2OCH3  O        
Figure C00819234004313
          H
6.13        H        CH3        O     
Figure C0081923400441
   H
6.14        H        CH3        O     
Figure C0081923400442
    H
6.15        H        CH3        O           H        165-167
6.16        H        CH3        S           H
6.17        H        CH3        O           H
6.18        H        CH3        O             H
6.19        H        CH3        O     
Figure C0081923400447
        H
6.20        H        CH3        O              H
6.21        H        CH3        O     
Figure C0081923400449
        H
6.22        H        CH3        O          H
6.23        H        CH3        O     
Figure C00819234004411
     H
6.24        H        CH3        O     
Figure C00819234004412
     H
6.25        H        CH3        O               H
6.26        H        CH3        O     
Figure C00819234004414
      H
6.27        H        CH3        O               H
6.28        H        CH3        O     
Figure C00819234004416
          H
6.29        H        CH3        O             H
6.30        H        CH3        O            H
6.31        CH3     CH3        O            H
6.32        H        CH3        O             H
6.33        H        CH3        S     
Figure C0081923400455
       H
6.34        H        CH3        O     
Figure C0081923400456
       H
6.35        H        CH3        O     
Figure C0081923400457
      H
表7：通式I的化合物，其中A＝A26＝
Figure C0081923400461
化合物        R1       R2        X        R31                 R4       物理数据
序号                                                                        熔点℃
7.1           H         CH3       O                     H
7.2           H         CH3       O        
Figure C0081923400463
         H         树脂
7.3           H         CH2CH3   O        
Figure C0081923400464
        H
7.4           H         CH2OCH3  O                  H
7.5           H         CH3       O                  H
7.6           H         CH2OCH3  O        
Figure C0081923400467
         H
7.7           H         CH3       S        
Figure C0081923400468
         H
7.8           H         CH3       O                  H
7.9           H         CH3       O                  H
7.10          CH3      CH3       O                  H
7.11          H         CH3       O        
Figure C00819234004612
        H
7.12          H         CH3       O        
Figure C00819234004613
       H
7.13        H        CH3        O            H
7.14        H        CH3        O     
Figure C0081923400472
      H
7.15        H        CH3        O     
Figure C0081923400473
       H
表8：通式I的化合物，其中A＝A27＝
化合物        R1       R2        X        R31                 R4      物理数据
序号                                                                       熔点℃
8.1           H         CH3       O        
Figure C0081923400475
            H        63-65
8.2           H         CH3       O        
Figure C0081923400476
         H        156-157
8.3           H         CH2CH3   O                 H
8.4           H         CH2OCH3  O        
Figure C0081923400478
        H
8.5           H         CH3       O        
Figure C0081923400479
         H        119-122
8.6           H         CH2OCH3  O        
Figure C00819234004710
         H
8.7           H         CH3       S        
Figure C00819234004711
         H
8.8           H         CH3       O                H
8.9         H        CH3        O         H
8.10        CH3     CH3        O             H
8.11        H        CH3        O              H
8.12        H        CH3        O      
Figure C0081923400484
      H
8.13        H        CH3        O           H
8.14        H        CH3        O              H        159-161
8.15        H        CH2OCH3   O              H        139-141
8.16        H        CH3        O                H        140-143
8.17        H        CH3        O      
Figure C0081923400489
    H
8.18        H        CH3        O      
Figure C00819234004810
      H
表9：通式I的化合物，其中A＝A31＝
化合物        R1       R2        X        R4      R5       R6        R7        R4        物理数据
序号                                                                                               熔点℃
9.1           H         CH3       O        H         H         CH3       CH3       CH3        165-167
9.2           H         CH2CH3   O        H         H         CH3       CH3       CH3
9.3    H      CH2OCH3     O    H    H    CH3    CH3  CH3    油状物：MS
9.4    CH3   CH3          O    H    H    CH3    CH3  CH3
9.5    H      CH3          S    H    H    CH3    CH3  CH3
9.6    H      CH3          O    H    CH3 CH3    CH3  H
9.7    H      CH2OCH3     O    H    CH3 CH3    CH3  H
表10：通式I的化合物，其中A＝A22＝
Figure C0081923400491
化合物        R1        R2        X        R31              R4        物理数据
序号                                                                       [熔点°C]
10.1          H         CH3       O                   H
10.2          H         CH3       O                   H
10.3          H         CH3       O        
Figure C0081923400494
     H            油状物
10.4          H         CH3       O        
Figure C0081923400495
     H
10.5          H         CH20CH3  O        
Figure C0081923400496
     H
10.6          H         CH3       O        
Figure C0081923400497
      H
10.7          H         CH3       O        
Figure C0081923400498
         H
10.8          H         CH3       O        
Figure C0081923400499
           H
10.9         H        CH3        O     
Figure C0081923400501
       H
10.10        H        CH3        O     
Figure C0081923400502
    H
10.11        H        CH2CH3    O          H
10.12        H        CH2OCH3   O     
Figure C0081923400504
    H
10.13        H        CH3        O     
Figure C0081923400505
   H
10.14        H        CH3        O          H
10.15        H        CH3        O     
Figure C0081923400507
     H        216-219
10.16        H        CH3        S        H
10.17        H        CH3        O           H
10.18        H        CH3        O     
Figure C00819234005010
       H
10.19        H        CH3        O             H
10.20        H        CH3        O              H
10.21        H        CH3        O     
Figure C00819234005013
        H
10.22        H        CH3        O          H
10.23        H        CH3        O           H
10.24        H        CH3        O           H
10.25        H        CH8        O       
Figure C0081923400511
      H
10.26        H        CH8        O       
Figure C0081923400512
   H
10.27        H        CH3        O       
Figure C0081923400513
      H
10.28        H        CH3        O               H
10.29        H        CH3        O       
Figure C0081923400515
       H
10.30        H        CH3        O       
Figure C0081923400516
      H
10.31        CH3     CH3        O              H
10.32        H        CH3        O               H
10.33        H        CH3        S       
Figure C0081923400519
       H
10.34        H        CH3        O       
Figure C00819234005110
       H
10.35        H        CH3        O              H
通式I化合物的制剂实施例
用于制备通式I化合物的制剂，如浓缩乳剂、溶液、颗粒剂、粉剂和可湿性粉剂的方法描述于WO 97/33890中。
生物学实施例：杀菌作用
实施例B-1：针对叶锈病/小麦(小麦褐霉病)的作用
用置于喷雾室中配制好的试验化合物(0.02％活性成分)处理1星期大的小麦植株cv.Arina。施用一天后，通过在试验植株上喷孢子悬浮液(1×105夏孢子/ml)对小麦植株进行接种。在20℃，95％的相对湿度下接种2天后，在20℃，60％的相对湿度的温室中保存8天。评定接种10天后的发病率。
在这些试验中，表1-10的化合物显示出优良的活性。化合物1.11、1.15、1.16、1.19-1.21、1.23-1.26、1.40、1.42、1.49、1.66-1.69、1.74、1.75、1.81、2.12、2.23、2.40、2.49、4.10、5.12、6.10、6.15、7.2、8.1、8.2、8.5、8.14-8.16、10.3和10.15显示出强效力(感染率＜20％)。
实施例 B-2：针对白粉病/苹果(苹果白粉病)的作用
用置于喷雾室中配制好的试验化合物(0.002％活性成分)处理5星期大的苹果秧苗cv.Mclntosh。施用一天后，通过在试验植株上方摇动被苹果白粉病感染的植株对苹果植株进行接种。在22℃，60％相对湿度下，在14/10h(光照/黑暗)的光照状态下培育12天后，评定发病率。
在这些试验中，表1-10的化合物显示出优良的活性。化合物1.11、1.15、1.16、1.19-1.21、1.23-1.26、1.40、1.42、1.49、1.66-1.69、1.74、1.75、1.81、2.12、2.23、2.40、2.49、4.10、5.12、6.10、6.15、7.2、8.1、8.2、8.5、8.14-8.16、10.3和10.15显示出强效力(感染率＜20％)。
实施例B-3：针对黑星病/苹果(苹果黑星病)的作用
用置于喷雾室中的配制好的试验化合物(0.02％活性成分)处理4星期大的苹果秧苗cv.Mclntosh。施用-天后，通过在试验植株上喷孢子悬浮液(4×105分生孢子/ml)对苹果植株进行接种。在21℃，95％的相对湿度下培育4天后，植株置于21℃，60％的相对湿度的温室中保存4天。在21℃，95％的相对湿度下另外培育4天后，评定发病率。
在这些试验中，表1-10的化合物显示出优良的活性。化合物1.11、1.15、1.16、1.19-1.21、1.23-1.26、1.40、1.42、1.49、1.66-1.69、1.74、1.75、1.81、2.12、2.23、2.40、2.49、4.10、5.12、6.10、6.15、7.2、8.1、8.2、8.5、8.14-8.16、10.3和10.15显示出了强效力(感染率＜20％)。
实施例B-4：针对麦类白粉病/大麦(大麦白粉病)的作用
用置于喷雾室中配制好的试验化合物(0.02％活性成分)处理1星期大的大麦植株cv.Express。施用一天后，通过在试验植株上方摇动被白粉病感染的植株对大麦植株进行接种。在20℃/18℃(白天/晚上)60％的相对湿度的温室中培育6天后，评定发病率。
在这些试验中，表1-10的化合物显示出优良的活性。化合物1.11、1.15、1.16、1.19-1.21、1.23-1.26、1.40、1.42、1.49、1.66-1.69、1.74、1.75、1.81、2.12、2.23、2.40、2.49、4.10、5.12、6.10、6.15、7.2、8.1、8.2、8.5、8.14-8.16、10.3和10.15显示出了强效力(感染率＜20％)。
实施例B-5：针对灰霉病/苹果(苹果灰霉病)的作用
在一个cv.Golden Delicious苹果果实上钻3个洞，每一个装填30μl已配制好的试验化合物液滴(0.002％的活性成分)。施用两小时后，将50μl灰霉病的孢子悬浮液(4×105分生孢子/ml)吸移到施用部位。在22℃的生长箱中培育7天后，评定发病率。
在这些试验中，表1-10的化合物显示出优良的活性。化合物1.11、1.15、1.16、1.19-1.21、1.23-1.26、1.40、1.42、1.49、1.66-1.69、1.74、1.75、1.81、2.12、2.23、2.40、2.49、4.10、5.12、6.10、6.15、7.2、8.1、8.2、8.5、8.14-8.16、10.3和10.15显示出了强效力(感染率＜20％)。
实施例B-6：针对灰霉病/葡萄(葡萄灰霉病)的作用
用置于喷雾室中配制好的试验化合物(0.002％活性成分)处理5星期大的葡萄秧苗cv.Gutedel。施用两天后，通过在试验植株上喷孢子悬浮液(1×106分生孢子/ml)对葡萄植株进行接种。在21℃，95％的相对湿度的温室中培育4天后，评定发病率。
在这些试验中，表1-10的化合物显示出优良的活性。化合物1.11、1.15、1.16、1.19-1.21、1.23-1.26、1.40、1.42、1.49、1.66-1.69、1.74、1.75、1.81、2.12、2.23、2.40、2.49、4.10、5.12、6.10、6.15、7.2、8.1、8.2、8.5、8.14-8.16、10.3和10.15显示出了强效力(感染率＜20％)。
实施例B-7：针对灰霉病/番茄(番茄灰霉病)的作用
用置于喷雾室中配制好的试验化合物(0.002％活性成分)处理4星期大的番茄植株cv.Roter Gnom。施用两天后，通过在试验植株上喷孢子悬浮液(1×105分生孢子/ml)对番茄植株进行接种。在20℃，95％的相对湿度的生长箱中培育4天后，评定发病率。
在这些试验中，表1-10的化合物显示出优良的活性。化合物1.11、1.15、1.16、1.19-1.21、1.23-1.26、1.40、1.42、1.49、1.66-1.69、1.74、1.75、1.81、2.12、2.23、2.40、2.49、4.10、5.12、6.10、6.15、7.2、8.1、8.2、8.5、8.14-8.16、10.3和10.15显示出了强效力(感染率＜20％)。
实施例B-8：针对网斑病/大麦(大麦网斑病)的作用
用置于喷雾室中的配制好的试验化合物(0.002％活性成分)处理1星期大的大麦植株cv.Express。施用两天后，通过在试验植株上喷孢子悬浮液(3×104分生孢子/ml)对大麦植株进行接种。在20℃，95％的相对湿度下培育2天后，在20℃，60％的相对湿度的温室中保存2天。评定接种4天后的发病率。
在这些试验中，表1-10的化合物显示出优良的活性。化合物1.11、1.15、1.16、1.19-1.21、1.23-1.26、1.40、1.42、1.49、1.66-1.69、1.74、1.75、1.81、2.12、2.23、2.40、2.49、4.10、5.12、6.10、6.15、7.2、8.1、8.2、8.5、8.14-8.16、10.3和10.15显示出了强效力(感染率＜20％)。
实施例B-9：针对颖枯病/小麦(小麦斑枯病)的作用
用置于喷雾室中配制好的试验化合物(0.02％活性成分)处理1星期大的小麦植株cv.Arina。施用一天后，通过在试验植株上喷孢子悬浮液(5×105分生孢子/ml)对小麦植株进行接种。在20℃，95％的相对湿度下培育1天后，在20℃，60％的相对湿度的温室中保存10天。评定接种11天后发病率。
在这些试验中，表1-10的化合物显示出优良的活性。化合物1.11、1.15、1.16、1.19-1.21、1.23-1.26、1.40、1.42、1.49、1.66-1.69、1.74、1.75、1.81、2.12、2.23、2.40、2.49、4.10、5.12、6.10、6.15、7.2、8.1、8.2、8.5、8.14-8.16、10.3和10.15显示出了强效力(感染率＜20％)。

Claims (12)

1.一种通式I的三氟甲基吡咯甲酰胺
其中，
X为氧或硫；
R1为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4卤代烷氧基-C1-C4烷基或卤素；
R2为C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基或C1-C4卤代烷氧基-C1-C4烷基；
A为下面的基团：
Figure C008192340002C2
其中
R3为噻吩基、呋喃基、噁唑基、异噁唑基、苯并噻吩基、四唑基、5，6-二H-1，4，2-二噁嗪基或吡啶基，其为未取代的或独立地被一个或多个选自卤素、C1-C6卤代烷基、C1-C6烷基和羟基的取代基所取代；和
R4为氢；或者所述三氟甲基吡咯甲酰胺选自
N-[2-(3-甲基环己基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺；和
N-[2-(3-甲基环戊基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺。
2.根据权利要求1通式I的化合物，其中X为氧。
3.根据权利要求1通式I的化合物，其中X为硫。
4.根据权利要求2通式I的化合物，其中
R1为氢、C1-C4烷基或C1-C4卤代烷基；
R2为C1-C4烷基、C1-C3卤代烷基或C1-C3烷氧基-C1-C3烷基；
A为A1；
R3为噻吩基、呋喃基、异噁唑基、噁唑基或吡啶基，其为未取代的或独立地被一个或多个选自卤素、羟基、C1-C4烷基和C1-C4卤代烷基的取代基所取代；和
R4为氢。
5.根据权利要求4通式I的化合物，其中
A为A1；
R1为氢或C1-C3烷基；
R2为C1-C3烷基或C1-C3烷氧基-C1-C3烷基；
R3为噻吩基、呋喃基或吡啶基，其为未取代的或独立地被一个或多个选自卤素、C1-C4基和C1-C4卤代烷基的取代基所取代；和
R4为氢。
6.根据权利要求3通式I的化合物，其中
R1为氢、C1-C4烷基或C1-C4卤代烷基；
R2为C1-C4烷基、C1-C3卤代烷基或C1-C3烷氧基-C1-C3烷基；
A为A1；
R3为噻吩基、呋喃基、异噁唑基、噁唑基或吡啶基，其为未取代的或独立地被一个或多个选自卤素、羟基、C1-C4烷基和C1-C4卤代烷基的取代基所取代；和
R4为氢。
7.根据权利要求6通式I的化合物，其中
A为A1；
R1为氢或C1-C3烷基；
R2为C1-C3烷基或C1-C3烷氧基-C1-C3烷基；
R3为噻吩基、呋喃基或吡啶基，其为未取代的或独立地被一个或多个选自卤素、C1-C4烷基和C1-C4卤代烷基的取代基所取代；和
R4为氢。
8.根据权利要求1的化合物，选自：
N-[2-(3-甲基环己基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺；和
N-[2-(3-甲基环戊基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺。
9.一种制备权利要求1的化合物的方法，包括使原料按照下列方案进行反应
Figure C008192340004C1
碱＝NEt3，Hünig-碱，Na2CO3，K2CO3
其中，R1、R2和A如权利要求1通式I中所定义；
或当A为苯基时根据如下方案反应
Figure C008192340004C2
G＝苯基
其中R1、R2和R3如权利要求1通式I所定义，或者
权利要求1的是化合物是
N-[2-(3-甲基环己基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺；或者
N-[2-(3-甲基环戊基)-苯基]-1-甲基-4-三氟甲基-1H-吡咯-3-甲酰胺。
10.一种用于防治微生物和防止植物受到侵蚀和感染的组合物，其中活性成分是权利要求1中所要求的化合物，该组合物还有含有一种适合的载体。
11.根据权利要求1的化合物在保护植物免受植物致病微生物感染方面的用途。
12.一种防治或防止栽培植物被植物致病微生物感染的方法，该方法通过将权利要求1所要求的化合物施用到植物、植物局部或其所在位置上而实现。
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