CN1293058C - 邻环丙基－n－甲酰苯胺及其作为杀菌剂的用途 - Google Patents

邻环丙基－n－甲酰苯胺及其作为杀菌剂的用途 Download PDF

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CN1293058C
CN1293058C CNB038051729A CN03805172A CN1293058C CN 1293058 C CN1293058 C CN 1293058C CN B038051729 A CNB038051729 A CN B038051729A CN 03805172 A CN03805172 A CN 03805172A CN 1293058 C CN1293058 C CN 1293058C
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J·埃伦福里安德
H·托伯勒
H·沃尔特
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Abstract

式(I)的化合物，其中Het是含有1—3个杂原子的5—6元杂环，每个杂原子独立的选自氧、氮和硫，该杂环被基团R4、R5和R6取代；R1是氢或卤原子；R2是氢或卤原子；R3是任选取代的C2-12烷基、任选取代的C2-12链烯基、任选取代的C2-12炔基、任选取代的C3-12环烷基、任选取代的苯基或任选取代的杂环基；和R4、R5和R6独立的选自氢、卤原子、氰基、硝基、C1-4卤代烷基、C1-4烷氧基(C(1-4)烷氧基(C1-4)烷基和C1-4卤代烷氧基(C1-4)烷基，条件是R4、R5和R6中的至少一个不是氢。式(I)化合物具有植物保护性能，适用于保护植物免受植物病原微生物的侵染。

Description

邻环丙基-N-甲酰苯胺及其作为杀菌剂的用途
本发明涉及具有杀微生物活性、特别是杀真菌活性的新的邻位取代的环丙基唑甲酰胺。本发明还涉及上述化合物的制备，在制备上述化合物中使用的新的中间体，包括至少一种所述新化合物作为活性成分的农药组合物，所述组合物的制备，和活性成分或组合物在农业或园艺上防治或预防植物病原微生物，尤其是真菌侵害植物的用途。
EP0545099A2、JP06220035和JP02129171公开了某些邻位-未取代的环丙基唑甲酰胺。
本发明提供了式(I)的化合物：
Het是含有1-3个杂原子的5-6元杂环，每个杂原子独立的选自氧、氮和硫，该杂环被基团R4、R5和R6取代；R1是氢或卤原子；R2是氢或卤原子；R3是任选取代的C2-12烷基、任选取代的C2-12链烯基、任选取代的C2-12炔基、任选取代的C3-12环烷基、任选取代的苯基或任选取代的杂环基；R4、R5和R6独立的选自氢、卤原子、氰基、硝基、C1-4烷基、C1-4卤代烷基、C1-4烷氧基(C1-4)烷基和C1-4卤代烷氧基(C1-4)烷基，条件是R4、R5和R6中的至少一个不是氢。
卤原子是氟、氯或溴。
每个烷基部分是直链的或支链的，例如，甲基、乙基、正丙基、正丁基、正戊基、正己基、异丙基、正丁基、仲丁基、异丁基、叔丁基或新戊基。
如果存在的话，烷基部分上每一个任选取代基独立的选自卤原子、羟基、氰基、C1-4烷氧基C(＝O)、甲酰基、硝基、C1-4烷氧基、C1-4卤代烷氧基、C1-4烷硫基、C1-4卤代烷硫基、HC(OR’)＝N和R’R”NN＝C(H)；其中R’和R”独立的是氢或C1-4烷基。
链烯基和炔基部分可以是直链或支链的形式。链烯基部分适合时可以是(E)-或(Z)-构型。其实例是乙烯基、烯丙基和炔丙基。
如果存在的话，链烯基或炔基上每一个任选取代基独立的选自上文烷基部分所给出的那些任选取代基。
环烷基包括环丙基、环丁基、环戊基和环己基。
如果存在的话，环烷基上每一个任选取代基独立的选自C1-3烷基和上文烷基部分所给出的那些任选取代基。
术语杂环基指的是含有至多10个原子的包括一个或多个(优选1或2个)独立的选自O、S和N的杂原子的非芳族环或芳族环。该环的实例包括1，3-二氧戊环基、四氢呋喃基、吗啉基、噻吩基和呋喃基。
如果存在的话，苯基或杂环基上每一个任选取代基独立的选自C1-6烷基和上文烷基部分所给出的那些任选取代基。当存在时，苯环上具有至多4个任选取代基，每个独立的进行选择。
如果存在的话，烷基部分上每个任选取代基独立的选自优选的卤原子、羟基、甲氧基、三氟甲氧基、二氟甲氧基、氰基和硝基。
如果存在的话，链烯基或炔基上每一个任选取代基独立的选自优选的卤原子和氰基。
如果存在的话，环烷基上每一个任选取代基独立的选自优选的甲基、乙基、三氟甲基、甲氧基、三氟甲氧基和氰基。
如果存在的话，苯基或杂环基上每一个任选取代基独立的选自优选的卤原子、羟基、甲氧基、三氟甲氧基、二氟甲氧基和氰基。
优选地，Het是吡咯基、吡唑基、噻唑基、吡啶基、嘧啶基、噻吩基、呋喃基、异噻唑基或异噁唑基(更优选吡咯基、吡唑基或噻唑基)，每一个被基团R4、R5和R6取代。
优选地，R1和R2独立的是氢或氟。
优选地，R3是C2-6烷基，任选取代的C3-8环烷基、苯基、噻吩基或呋喃基。
优选地，R4、R5和R6独立的选自氢、卤素、C1-4烷基、C1-4卤代烷基和C1-4烷氧基(C1-4)烷基；条件是R4、R5和R6中的至少一个不是氢。更优选地，R4、R5和R6独立的选自氢、卤素、甲基、C1-2卤代烷基和甲氧基甲基；条件是R4、R5和R6中的至少一个不是氢。
式(II)的化合物
其中R3如上文式(I)化合物中所定义，也是新的，可用作制备式(I)化合物的中间体。
因此，本发明另一方面提供了式(II)的化合物，其中R3如上文式(I)化合物中所定义。
式(I)和式(II)的化合物可以不同的几何异构体或旋光异构体或不同的互变异构体形式存在。本发明包括了所有的上述异构体和互变异构体及其以所有比例的混合物，以及同位素形式如氘代化合物。
下文的表1-6中化合物举例说明了本发明的化合物。
表1提供了式(II)的22种化合物，其中R3如表1所定义。
                表1
  化合物号   R3
  1.1   CH2CH3
  1.2   CH2CH2CH3
  1.3   CH(CH3)2
  1.4   CH2CH2CH2CH3
  1.5   CH2CH(CH3)2
  1.6   C(CH3)3
  1.7   CH2CH2CH2CH2CH3
  1.8   CH2CH2CH(CH3)2
  1.9   CH2CH2CH(CH3)2
  1.10   环丙基
  1.11   环丁基
  1.12   环戊基
  1.13   环己基
  1.14   环庚基
  1.15   环辛基
  1.16   苯基
  1.17   p-Cl-苯基
  1.18   p-F-苯基
  1.19   p-Br-苯基
  1.20   噻吩基
  1.21   呋喃基
  1.22   α-甲基环丙基
表X代表表2(当X是2时)和代表表3(当X是3时)。
                               表X
  化合物号   R1   R2   R3   R4   R5   R6
  X.1   H   H   CH2CH3   CF3   CH3   H
  X.2   H   H   CH2CH3   CF3   CH2OCH3   H
  X.3   H   H   CH2CH2CH3   CF3   CH3   H
  X.4   H   H   CH2CH2CH3   CF2H   CH3   H
  X.5   H   H   CH(CH3)2   CF3   CH3   H
  X.6   H   H   CH(CH3)2   CF2H   CH3   H
  X.7   H   H   CH(CH3)2   CFH2   CH3   H
  X.8   H   H   CH(CH3)2   CH3   CH3   Cl
  X.9   H   H   CH(CH3)2   CH3   CH2CH3   Cl
  化合物号   R1   R2   R3   R4   R5   R6
  X.10   H   H   CH(CH3)2   CH3   CH3   F
  X.11   H   H   CH(CH3)2   CH3   CH2CH3   F
  X.12   H   H   CH(CH3)2   CF2Cl   CH3   F
  X.13   H   H   CH2CH2CH2CH3   CF3   CH3   H
  X.14   H   H   CH2CH2CH2CH3   CF2H   CH3   H
  X.15   H   H   CH2CH2CH2CH3   CH3   CH3   F
  X.16   H   H   CH2CH2CH2CH3   CH3   CH3   Cl
  X.17   H   H   CH2CH(CH3)2   CF3   CH3   H
  X.18   H   H   CH2CH(CH3)2   CF2H   CH3   H
  X.19   H   H   CH2CH(CH3)2   CFH2   CH3   H
  X.20   H   H   CH2CH(CH3)2   CF3   CH2OCH3   H
  X.21   H   H   CH2CH(CH3)2   CH3   CH3   F
  X.22   H   H   CH2CH(CH3)2   CH3   CH3   Cl
  X.23   H   H   C(CH3)3   CF3   CH3   H
  X.24   H   H   C(CH3)3   CF2H   CH3   H
  X.25   H   H   C(CH3)3   CF2H   CH3   H
  X.26   H   H   C(CH3)3   CH3   CH3   F
  X.27   H   H   C(CH3)3   CH3   CH3   Cl
  X.28   H   H   C(CH3)3   CF2Cl   CH3   H
  X.29   H   H   CH2CH2CH2CH2CH3   CF3   CH3   H
  X.30   H   H   CH2CH2CH(CH3)2   CF3   CH3   H
  X.31   H   H   CH2CH2CH(CH3)2   CF2H   CH3   H
  X.32   H   H   CH2CH2CH2CH2CH2CH3   CF3   CH3   H
  X.33   H   H   环丙基   CF3   CH3   H
  X.34   H   H   环丙基   CF2H   CH3   H
  X.35   H   H   环丙基   CH3   CH3   F
  X.36   H   H   环丙基   CH3   CH3   Cl
  X.37   H   H   环丁基   CF3   CH3   H
  X.38   H   H   环丁基   CF2H   CH3   H
  化合物号   R1   R2   R3   R4   R5   R6
  X.39   H   H   环戊基   CF3   CH3   H
  X.40   H   H   环戊基   CF2H   CH3   H
  X.41   H   H   环戊基   CFH2   CH3   H
  X.42   H   H   环戊基   CF2Cl   CH3   H
  X.43   H   H   环戊基   CH3   CH3   F
  X.44   H   H   环戊基   CH3   CH3   Cl
  X.45   H   H   环己基   CF3   CH3   H
  X.46   H   H   环己基   CF2H   CH3   H
  X.47   H   H   环己基   CFH2   CH3   H
  X.48   H   H   环己基   CF2Cl   CH3   H
  X.49   F   F   环己基   CF3   CH3   H
  X.50   H   H   环己基   CH3   CH3   F
  X.51   H   H   环己基   CH3   CH3   Cl
  X.52   H   H   环庚基   CF3   CH3   H
  X.53   H   H   环庚基   CF3   CH2CH3   H
  X.54   H   H   环庚基   CF2H   CH3   H
  X.55   H   H   环庚基   CFH2   CH3   H
  X.56   H   H   环庚基   CF2Cl   CH3   F
  X.57   H   H   环庚基   CH3   CH3   F
  X.58   H   H   环庚基   CH3   CH3   Cl
  X.59   H   H   环辛基   CF3   CH3   H
  X.60   H   H   环辛基   CF2H   CH3   H
  X.61   H   H   苯基   CF3   CH3   H
  X.62   H   H   苯基   CF2H   CH3   H
  X.63   H   H   苯基   CFH2   CH3   H
  X.64   H   H   苯基   CH3   CH3   F
  X.65   H   H   苯基   CH3   CH3   Cl
  X.66   H   H   4-氟苯基   CF3   CH3   H
  X.67   H   H   4-氟苯基   CF2H   CH3   H
  化合物号   R1   R2   R3   R4   R5   R6
  X.68   H   H   4-氯苯基   CF3   CH3   H
  X.69   H   H   4-氯苯基   CF2H   CH3   H
  X.70   H   H   4-溴苯基   CF3   CH3   H
  X.71   H   H   4-溴苯基   CF2H   CH3   H
  X.72   H   H   2-噻吩基   CF3   CH3   H
  X.73   H   H   3-噻吩基   CF3   CH3   H
  X.74   H   H   2-呋喃基   CF3   CH3   H
  X.75   H   H   2-呋喃基   CF3   CH3   H
  X.76   H   H   α-甲基环丙基   CF3   CH3   H
  X.77   H   H   α-甲基环丙基   CF2H   CH3   H
  X.78   H   H   α-甲基环丙基   CH3   CH3   F
  X.79   H   H   α-甲基环丙基   CH3   CH3   Cl
  X.80   H   H   α-甲基环丙基   CF3   CH3   Cl
表2提供了式(1a)的80种化合物：
Figure C0380517200101
其中R1、R2、R3、R4、R5和R6如表2中所定义。
表3提供了式(1b)的80种化合物：
Figure C0380517200102
其中R1、R2、R3、R4、R5和R6如表3中所定义。
表4提供了式(1c)的50种化合物：
Figure C0380517200103
其中R1、R2、R3、R4和R5如表4中所定义。
                                 表4
  化合物号   R1   R2     R3   R4     R5
   4.1   H   H     CH2CH3   CF3     CH3
   4.2   H   H     CH2CH3   CH3     CH3
   4.3   H   H     CH2CH2CH3   CF3     CH3
   4.4   H   H     CH2CH2CH3   CH3     CH3
   4.5   H   H     CH(CH3)2   CF3     CH3
   4.6   H   H     CH(CH3)2   CH3     CH3
   4.7   H   H     CH(CH3)2   CH2CH3     CH3
   4.8   H   H     CH2CH2CH2CH3   CF3     CH3
   4.9   H   H     CH2CH2CH2CH3   CH3     CH3
   4.10   H   H     CH2CH(CH3)2   CF3     CH3
   4.11   H   H     CH2CH(CH3)2   CH3     CH3
   4.12   H   H     C(CH3)3   CF3     CH3
   4.13   H   H     CH2CH2CH2CH2CH3   CF3     CH3
   4.14   H   H     CH2CH2CH2CH2CH3   CH3     CH3
   4.15   H   H     CH2CH2CH(CH3)2   CF3     CH3
   4.16   H   H     CH2CH2CH(CH3)2   CH3     CH3
   4.17   H   H     CH2CH2CH(CH3)2   CH3     CH2CH3
   4.18   H   H     CH2CH2CH2CH2CH2CH3   CF3     CH3
   4.19   H   H     CH2CH2CH2CH2CH2CH3   CH3     CH3
   4.20   H   H     环丙基   CF3     CH3
   4.21   H   H     环丙基   CH3     CH3
   4.22   H   H     环丁基   CF3     CH3
   4.23   H   H     环丁基   CH3     CH3
   4.24   H   H     环戊基   CF3     CH3
   4.25   H   H     环戊基   CH3     CH3
   4.26   H   H     环己基   CF3     CH3
   4.27   H   H     环己基   CH3     CH3
  化合物号   R1   R2   R3   R4   R5
  4.28   H   H   环己基   CF3   CH2CH3
  4.29   H   H   环庚基   CF3   CH3
  4.30   H   H   环庚基   CH3   CH3
  4.31   H   H   环辛基   CF3   CH3
  4.32   H   H   环辛基   CH3   CH3
  4.33   H   H   苯基   CF3   CH3
  4.34   H   H   苯基   CH3   CH3
  4.35   H   H   4-氟苯基   CF3   CH3
  4.36   H   H   4-氟苯基   CH3   CH3
  4.37   H   H   4-氯苯基   CF3   CH3
  4.38   H   H   4-氯苯基   CH3   CH3
  4.39   H   H   4-溴苯基   CF3   CH3
  4.40   H   H   4-溴苯基   CH3   CH3
  4.41   H   H   2-噻吩基   CF3   CH3
  4.42   H   H   2-噻吩基   CH3   CH3
  4.43   H   H   3-噻吩基   CF3   CH3
  4.44   H   H   3-噻吩基   CH3   CH3
  4.45   H   H   2-呋喃基   CF3   CH3
  4.46   H   H   2-呋喃基   CH3   CH3
  4.47   H   H   3-呋喃基   CF3   CH3
  4.48   H   H   3-呋喃基   CH3   CH3
  4.49   H   H   α-甲基环丙基   CF3   CH3
  4.50   H   H   α-甲基环丙基   CH3   CH3
表5提供了式(1d)的54种化合物：
其中R1、R2、R3和R4如表5中所定义。
                    表5
  化合物号   R1   R2   R3   R4
  5.1   H   H   CH2CH3   Cl
  5.2   H   H   CH2CH2CH3   Cl
  5.3   H   H   CH2CH2CH3   Br
  5.4   H   H   CH2CH2CH3   CF3
  5.5   H   H   CH(CH3)2   Cl
  5.6   H   H   CH(CH3)2   Br
  5.7   H   H   CH(CH3)2   CF3
  5.8   H   H   CH2CH2CH2CH3   Cl
  5.9   H   H   CH2CH2CH2CH3   Br
  化合物号   R1   R2   R3   R4
  5.10   H   H   CH2CH2CH2CH3   CF3
  5.11   H   H   C(CH3)3   Cl
  5.12   H   H   CH2CH(CH3)2   Cl
  5.13   H   H   CH2CH(CH3)2   Br
  5.14   H   H   CH2CH(CH3)2   CF3
  5.15   H   H   CH2CH2CH2CH2CH3   Cl
  5.16   H   H   CH2CH2CH2CH2CH3   Br
  5.17   H   H   CH2CH2CH(CH3)2   Cl
  5.18   H   H   CH2CH2CH(CH3)2   Br
  5.19   H   H   CH2CH2CH2CH2CH2CH3   Cl
  5.20   H   H   CH2CH2CH2CH2CH2CH3   Br
  5.21   H   H   环丙基   Cl
  5.22   H   H   环丙基   Br
  5.23   H   H   环丁基   Cl
  5.24   H   H   环丁基   Br
  5.25   H   H   环戊基   Cl
  5.26   H   H   环戊基   Br
  5.27   F   F   环戊基   CF3
  5.28   H   H   环己基   Cl
  5.29   H   H   环己基   Br
  5.30   H   H   环己基   CF3
  5.31   H   H   环庚基   Cl
  5.32   H   H   环庚基   Br
  5.33   H   H   环庚基   CF3
  5.34   H   H   环辛基   Cl
  5.35   H   H   苯基   Cl
  5.36   H   H   苯基   Br
  5.37   H   H   4-氟苯基   Cl
  5.38   H   H   4-氟苯基   Br
  化合物号   R1   R2   R3   R4
  5.39   H   H   4-氟苯基   CF3
  5.40   H   H   4-氯苯基   Cl
  5.41   H   H   4-氯苯基   Br
  5.42   H   H   4-氯苯基   CF3
  5.43   H   H   4-溴苯基   Cl
  5.44   H   H   2-噻吩基   Cl
  5.45   H   H   2-噻吩基   Br
  5.46   H   H   3-噻吩基   Cl
  5.47   H   H   3-噻吩基   Cl
  5.48   H   H   2-呋喃基   Cl
  5.49   H   H   2-呋喃基   Br
  5.50   H   H   3-呋喃基   Cl
  5.51   H   H   3-呋喃基   Br
  5.52   H   H   2-吡啶基   Cl
  5.53   H   H   α-甲基环丙基   Cl
  5.54   H   H   α-甲基环丙基   Br
表6提供了式(1e)的45种化合物：
Figure C0380517200161
其中R1、R2、R3和R4如表6中所定义。
                        表6
  化合物号   R1   R2   R3   R4
  6.1   H   H   CH2CH3   CH3
  6.2   H   H   CH2CH2CH3   CF3
  6.3   H   H   CH2CH2CH3   CH3
  6.4   H   H   CH(CH3)2   CF3
  6.5   H   H   CH(CH3)2   CH3
  6.6   H   H   CH2CH2CH2CH3   CF3
  6.7   H   H   CH2CH2CH2CH3   CH3
  6.8   H   H   CH2CH(CH3)2   CF3
  6.9   H   H   CH2CH(CH3)2   CH3
  6.10   H   H   C(CH3)3   CF3
  6.11   H   H   C(CH3)3   CH3
  6.12   H   H   CH2CH2CH2CH2CH3   CF3
  6.13   H   H   CH2CH2CH2CH2CH3   CH3
  6.14   H   H   CH2CH2CH(CH3)2   CF3
  6.15   H   H   CH2CH2CH(CH3)2   CH3
  6.16   H   H   CH2CH2CH2CH2CH2CH3   CF3
  6.17   H   H   CH2CH2CH2CH2CH2CH3   CH3
  6.18   H   H   环丙基   CF3
  6.19   H   H   环丙基   CH3
  化合物号   R1   R2   R3   R4
  6.20   H   H   环丁基   CF3
  6.21   H   H   环丁基   CH3
  6.22   H   H   环己基   CF3
  6.23   H   H   环己基   CH3
  6.24   H   H   环庚基   CF3
  6.25   F   F   环庚基   CH3
  6.26   H   H   环辛基   CF3
  6.27   H   H   环辛基   CH3
  6.28   F   F   环辛基   CF3
  6.29   H   H   苯基   CF3
  6.30   H   H   苯基   CH3
  6.31   H   H   4-氟苯基   CF3
  6.32   H   H   4-氟苯基   CH3
  6.33   H   H   4-氯苯基   CF3
  6.34   H   H   4-氯苯基   CH3
  6.35   H   H   4-溴苯基   CF3
  6.36   H   H   2-噻吩基   CF3
  6.37   H   H   2-噻吩基   CH3
  6.38   H   H   3-噻吩基   CF3
  6.39   H   H   3-噻吩基   CH3
  6.40   H   H   2-呋喃基   CF3
  6.41   H   H   3-呋喃基   CF3
  6.42   H   H   2-吡啶基   CF3
  6.43   H   H   4-吡啶基   CF3
  6.44   H   H   α-甲基环丙基   CF3
  6.45   H   H   α-甲基环丙基   CH3
在本说明书中，温度给出的是摄氏度；“NMR”指的是核磁共振光谱；MS代表质谱；和“％”是重量百分数，除非用其它的单位表示相应的浓度。
在本说明书中使用下面的缩写：
m.p.＝熔点               b.p.＝沸点
S＝单峰                  br＝宽峰
d＝双峰                  dd＝双二重峰
t＝三重峰                q＝四重峰
m＝多重峰                ppm＝百万分之
表7列出了表1-6中化合物(不打算列出所有情况下的所有表征数据)的有选择的熔点和有选择的NMR数据，所有的都是用CDCl3作溶剂(除非有其它的说明；如果存在溶剂的混合物时，将会指明，例如(CDCl3/d6-DMSO))。除非有其它的说明，该数据涉及的是每一种化合物的顺式/反式混合物；末尾有字母‘c’的化合物号仅涉及其顺式异构体，末尾有字母‘t’的化合物号仅涉及其反式异构体。
                                             表7
  化合物号 1H-NMR数据：(ppm/多重性/H的数目)     m.p./(℃)
    1.3 0.6-0.90/m/8H(顺式和反式)；1.02/d/6H(顺式)；1.11/6H(反式)；1.48/m/1H(反式)；1.78/m/1H(顺式)；3.83/s/4H(NH2顺式和反式)；6.68/m/4H(顺式和反式)；7.0/m/4H(顺式和反式)    油状物
    1.5 0.6-1.1/m/6H(顺式和反式)；0.95-101/2d/12H(顺式和反式)；1.25/m/2H(顺式或反式)；1.40/m/2H(顺式或反式)；1.78/m/2H(顺式或反式)：3.85/s/4H(NH2顺式和反式)；6.70/m/4H(顺式和反式)；7.0/m/4H(顺式和反式)    油状物
    1.6t 0.52/m/1H；0.80/m/1H；0.97/s/9H；1.08/m/1H；1.57/m/1H；3.85/s/2H；6.68/m/2H；7.0/m/2H.    油状物
    1.10c 0.01/m/2H，0.11/m/1H；0.22/m/1H；0.58/m/1H；0.69/m/1H；0.85/m/1H；1.67/m/1H；3.75/s/2H(NH2)；649-6.60/m/2H；6.82-7.00/m/2H.    油状物
    1.10t 0.01/m/2H；0.30/m/2H；0.55/M/2H；0.72/m/2H；1.28/m/1H；3.70/s/2H(NH2)；6.45-6.55/m/2H；6.77-6.85/m/2H.    油状物
    1.12 0.75/m/4H(顺式和反式)；0.97/m/2H(顺式和反式)；1.3-1.95/m/20H(顺式和反式)；3.88/s/4H(顺式和反式)；6.68/m/4H(顺式和反式)；7.01/m/4H(顺式和反式)；    油状物
    1.13 0.62-1.98/m/30H(顺式和反式)；3.80/s/4H(顺式和反式)；6.65/m/4H(顺式和反式)；6.97/m/4H(顺式和反式)    油状物
    1.17c    110-112
    1.17t    69-70
    1.18c 1.29/m/1H；1.52/m/1H；2.20/m/1H；2.42/m/1H；3.55/s/2H；6.50/d/1H；6.65-6.85/m/5H；6.99/t/1H；7.09/d/1H.    油状物
  1.18t   95-97
  1.22c   60-62
  1.22t   0.01-0.1/m/4H；0.42/m/2H；0.99/s/3H；1.01/m/1H；1.21/m/1H；3.55/s/2H；6.45/m/2H；6.78/m/2H.   油状物
  2.5   99-102
  2.17   75-78
  2.18   74-79
  2.23   134-136
  2.24   110-112
  2.33   88-92
  2.34c   111-113
  2.34t   116-118
  2.35c   93-95
  2.35t   134-136
  2.45   0.6-1.90/m/30H(顺式和反式)；4.0/s/6H(顺式和反式)；7.0-7.28/m/6H(顺式和反式)；8.0/s/1H(反式)；8.05/s/1H(顺式)8.12/d/2H(反式)；8.20/d/2H(顺式)   树脂状物
  2.46t   116-118
  2.52   116-118
  2.54 129-131
  2.57 107-109
  2.66c   树脂状物
  2.66t 145-147
  2.67c 104-106
  2.67t 160-161
  2.68c   树脂状物
  2.68t   148-150
  2.69c   145-147
  2.69t   149-150
2.76c 119-121
  2.76t   107-108
  2.77c   82-84
  2.77t   109-111
  2.78c   119-122
  2.78t   96-97
  3.5   74-78
  3.17   61-65
  3.23   92-96
  3.33   -0.1-0.90/m/16H(顺式和反式)；1.45/m/1H(反式)；1.79/m/1H(顺式)3.58/s/6H(顺式和反式)；)；6.82-7.13/m/10H(顺式和反式)；7.92/s/1(NH-反式)；8.03/dd/1H(反式)；8.10/s/1H(NH-顺式)8.19/dd/1H(顺式)；   树脂状物
  3.39   0.63-1.83/m/26H(顺式和反式)；3.72/s/6H(顺式和反式)；；6.95-7.38/m/10H(顺式和反式)；8.05/s/1H(NH-反式)；8.18/dd/1H(反式)；8.30/dd/1H(顺式)；   树脂状物
  3.45   0.6-1.90/m/30H(顺式和反式)；3.70/s/6H(顺式和反式)；6.98-7.35/m/8H(顺式和反式)；8.08/s(宽峰))/2H(顺式和反式)；8.17/d/2H(反式)；8.25/d/2H(顺式)；   树脂状物
  3.66c   1.40/m/1H；1.50-1.65/m/1H；2.37/m/1H，2.50/m/1H；3.73/s/3H；6.60-6.70/m/5/H；6.97/m/2H；7.18/m/3H；7.82/s/1H(NH)；8.02/d/1H.   树脂状物
  3.66t   146-148
  3.68c   1.40/m/1H；1.57/m/1H；2.40/m/2H；3.72/s/3H；6.68/d/2H；6.90-7.08/m/4H；7.18/m/3H；7.80/s/1H；8.02/d/1H.   树脂状物
  3.68t   150-152
  3.76   树脂状物
  3.80c   123-126
  3.80t   94-96
  4.10   69-74
  4.12   树脂状物
  4.24   113-115
  4.26   138-142
  5.5   树脂状物
  5.12   83-86
  5.21c   75-77
  5.21t   80-82
  5.25   131-133
  5.28   115-119
  5.37c   164-166
  5.37t   133-135
  5.40c   160-162
  5.40t   136-138
  5.53c   -0.25/m/1H；-0.01-0.03/m/3H；0.60/s/3H；0.65/m/1H；0.79/m/1H；1.25/m/1H；1.80/m/1H；6.95/t/1H；7.08/m/2H；7.28/m/1H；8.15/d/2H；8.38/m/1H；8.62/s/1H(NH).   树脂状物
  5.53t   0.01/m/4H；0.58/m/2H；0.94/s/3H；1.11/m/1H；1.44/m/1H；6.98/m/2H；7.09/m/1H；7.23/m/1H；8.01/dd/1H；8.10/d/1H；8.35/dd/1H；8.40/s/1H.   树脂状物
  6.10   树脂状物
式(I)的化合物可根据下面的反应方案来制备。
方案1A
式(II)化合物[其中R3如上文式(I)化合物中所定义]可通过由苯甲醛与式CH3C(O)R3[其中R3如上文式(I)化合物中所定义]的酮在NaOH或KOH存在下于溶剂(如水或乙醇)中，并且通常在回流条件下的交叉羟醛缩合起始的反应步骤来制备，或者可供选择性地，通过苯甲醛在标准条件下与维悌希试剂(Witting reagent)反应来制备。所得式(III)[其中R3如上文的式(I)化合物中所定义]的α，β-不饱和酮：
然后可通过首先在乙醇中回流条件下与水合肼反应，再在KOH的存在下加热(150-250℃)(蒸馏出溶剂)而转化为式(IV)化合物[其中R3如上文的式(I)化合物中所定义]。
在冷却的容器(-30℃至0℃)中，用HNO3/H2O或HNO3/乙酸酐硝化后，所得的式(V)[其中R3如上文的式(I)化合物中所定义]的邻/对-硝基苯混合物：
然后可分离并在溶剂(如甲醇、乙醇或THF)中于室温下催化还原(Pt/C/H2或Ra-Ni/H2)，得到式(II)化合物的邻/对-混合物粗品，其可通过标准方法进一步纯化。
可供选择性地是，式(II)的化合物[其中R3如上文的式(I)化合物中所定义]可通过下面的反应顺序所举例说明的方法来制备，该方法涉及Pd(II)催化的亚胺化步骤。
方案1B
式(VIII)化合物[其中R3如上文的式(I)化合物中所定义]在5-10℃的温度下加入到溴和甲醇中，然后加入三苯基膦在溶剂[如四氢呋喃]中的溶液，得到式(IX)化合物[其中R3如上文的式(I)化合物中所定义]，再加入到氢化钠在溶剂[如DMSO]的溶液中，然后与2-溴苯甲醛或2-碘苯甲醛反应得到式(X)化合物[其中R3如上文的式(I)化合物中所定义，Hal是溴或碘]。所得的式(X)化合物然后与溶剂[如乙醇]中的水合肼混合，加热至回流，然后加入氢氧化钾，所得的反应混合物维持在200-220℃几个小时。用标准的萃取和纯化方法得到式(XI)化合物[其中R3如上文的式(I)化合物中所定义，Hal是溴或碘]，然后可通过与二苯甲酮亚胺、叔丁醇钠、三(二亚苄基丙酮)二钯(Pd2dba3)、外消旋2，2’-二(二苯基膦)-1，1’-联萘(BINAP)和溶剂(如苯或甲苯)混合，在回流温度下加热，优选几个小时，再将所得的[通常是分离的粗产物]亚胺加入到盐酸羟胺、乙酸钠和溶剂(如甲醇)的混合物中，转化为式(II)化合物。所得的混合物室温下搅拌，优选约1个小时，然后可萃取式(II)化合物的顺式/反式混合物，随后可利用快速色谱进行顺反异构体的分离。
在上述的Pd催化的亚胺化步骤中，用二乙酸钯/1，1’-二(二苯基膦)二茂铁(dppf)体系代替催化剂-配体-体系Pd2dba3/BINAP也可作为一个选择。
反应方案1B具有新颖性和创造性，特别是Pd(II)-催化的亚胺化步骤的使用。因此，本发明再一个方面还提供了制备式(II)化合物的方法，其中R3如上文所定义，包括至少一个反应方案1B的步骤；特别是利用Pd(II)催化剂-配体-体系[其中，配体选自适合空间位阻要求的膦(例如BINAP或dppf)]，使式(XI)化合物[其中Hal是溴或碘；和R3如上文所定义]任选在碱[如叔丁醇钠、叔丁醇钾、碳酸钠、碳酸钾或碳酸铯]存在下与二苯甲酮亚胺反应制备式(XII)化合物[其中R3如上文所定义]的步骤。
与二苯甲酮亚胺进行亚胺化反应的实例在文献(Journal ofOrganometallic Chemistry，1999，576，125-146和Tetrahedron Letters1997，38，6367-6370)中有记载。
方案2
式(IIA)胺的合成
Figure C0380517200251
[其中R3A是氢或甲基]可通过由邻硝基苯甲醛与叶立德[在强碱，如NaH的存在下，在溶剂如DMSO中，由溴化环丙基甲基三苯基鏻于0-85℃下制备]的维悌希反应起始的反应顺序来完成。所得的式(VI)化合物的E/Z混合物
Figure C0380517200261
[其中R3A是氢或甲基]可通过对式(VI)化合物烯属基团进行Simmons Smith反应(Zn/Cu，CH2I2，乙醚作溶剂)而转化为式(VII)化合物。
Figure C0380517200262
利用方案1中所述的条件可对式(VII)相应化合物的硝基进行还原得到式(IIA)化合物。
方案3
式(I)化合物可通过将式Het-C(＝O)-R*化合物[其中R*是卤素、羟基或C1-6烷氧基，但优选氯]与上文制备的式(II)化合物在碱(如三乙胺、Hunig碱、碳酸氢钠、碳酸钠、碳酸钾、吡啶或喹啉，但优选三乙胺)的存在下于溶剂(如乙醚、TBME、THF、二氯甲烷、氯仿、DMF或NMP)中反应10分钟至48小时(优选12-24小时)，反应温度为0℃至回流温度(优选20-25℃)。当R*是羟基时，可使用偶联剂[如苯并三唑-1-基氧基三(二甲基氨基)六氟磷酸盐、二(2-氧代-3-噁唑烷基)膦酰氯、N，N’-二环己基碳二亚胺或1，1’-羰基二咪唑]。
方案4
式(IA)化合物
Figure C0380517200271
[其中R3A是氢或甲基]可通过以下方法来制备，利用标准条件(例如，催化还原或伯钱(Bēchamp-reduction)还原)将式(VI)化合物[其中R3A是氢或甲基]的硝基还原，然后用酰氯进行酰胺化得到式(VII)化合物[其中R3A是氢或甲基]
随后进行Simmons-Smith反应(Zn/Cu，CH2I2，乙醚作溶剂)得到式(IA)化合物。
令人惊奇地，在实用性方面，现已发现式(I)的新化合物在保护植物抵抗由真菌以及细菌和病毒引起的病害中具有非常有利的活性谱。
式(I)化合物作为活性成分可被用于农业和相关应用领域用于防治植物害虫。该新化合物在低施用剂量下就有优异的活性，能被植物较好地耐受，并且对环境安全。它们具有非常优异的治疗性、保护性和内吸性，被用来保护多种作物。式I化合物可用来抑制或杀死那些发生在各种有益农作物的植物体或植物体的部分(果实、花、叶、茎、块茎、根)上的害虫，同时也保护了后来长出的各种植物部分例如免受植物病原微生物的侵染。
式(I)化合物也可以作为拌种剂来处理植物繁殖材料，特别是种子(果实、块茎、谷粒)和植物插条(例如稻)，以防止真菌的侵染和植物病原真菌在土壤中的发生。
另外，本发明化合物可用于相关领域中防治真菌，例如工业材料包括木材和木材相关的工业产品的保护、食品储藏、卫生管理等等。
式(I)化合物例如对下面各纲的植物病原真菌是有效的：半知菌类(如葡萄孢属、梨孢属、长孺孢属、镰孢菌属、壳针孢属、尾孢属和链格孢属)和担子菌纲(如丝核菌属、驼孢菌属、柄锈菌属)，另外，它们对子囊菌纲(如黑星菌属和白粉菌属、叉丝单囊壳属、链核盘菌属、钩丝壳属)和卵菌纲(如疫霉属、腐霉属、单轴霉属)也是有效的。对白粉病(白粉菌属)具有突出的活性。另外，式I的新化合物对植物病原细菌和病毒(如黄单孢杆菌属、假单孢杆菌属、梨火疫病菌以及烟草花叶病毒)也是有效的。
在本发明范围内，可以被保护的目标作物典型地包括下列的作物品种：谷类(小麦、大麦、黑麦、燕麦、稻、玉米、高粱和相关的品种)；甜菜(糖用甜菜和饲料甜菜)；仁果、核果和浆果(苹果、梨、李、桃、杏、樱桃、草莓、悬钩子和黑莓)；豆科作物(菜豆、扁豆、豌豆、大豆)；油料作物(油菜、芥菜、罂粟、油橄榄、向日葵、椰子、蓖麻、可可豆、花生)；瓜类作物(南瓜、黄瓜、甜瓜)；纤维作物(棉花、亚麻、大麻、黄麻)；柑橘类的水果(橙子、柠檬、柚子、柑橘)；蔬菜(菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、番茄、马铃薯、辣椒)；樟科(鳄梨、樟属、樟脑)或其它作物如烟草、坚果、咖啡、茄子、甘蔗、茶叶、胡椒、藤、蛇麻草、香蕉和天然橡胶以及观赏植物。
式(I)化合物可以直接施用，或优选地与制剂领域中常用的助剂混和使用。为此，它们通常用公知的方法加工成乳油、包衣糊剂、直接喷施或可稀释的液剂、稀释的乳剂、可湿性粉剂、可溶性粉剂、粉剂、颗粒剂以及例如包在聚合物中的胶囊剂。如同组合物的类型一样，施用方法如喷雾、弥雾、喷粉、撒施、包衣或浇注，可以根据欲达到的目的和当时的环境进行选择。该组合物也可包含其它的助剂如稳定剂、消泡剂、粘度调节剂、粘合剂或增粘剂以及肥料、微量元素供体或其它制剂来获得特殊的效果。
合适的载体和助剂可以是固体的或液体的，是用于剂型加工中的物质，例如天然的或再生的矿物质、溶剂、分散剂、润湿剂、增粘剂、增稠剂、粘合剂或肥料。所述载体例如在WO97/33890中有记载。
式(I)化合物通常以组合物的形式使用，可施用到作物田或要防治的植物上，可同时或之后施用另外的化合物，上述另外的化合物可以是例如肥料或微量元素供体或其它影响植物生长的制剂。它们也可以是选择性的除草剂以及杀虫剂、杀真菌剂、杀细菌剂、杀线虫剂、杀软体动物剂或几种上述制剂的混合物，如果需要，还可进一步有该制剂领域常用的载体、表面活性剂或施用促进剂。
式(I)化合物可与其它杀菌剂混和使用，一些情况下可得到预想不到的增效效果。混和成分特别优选的是唑类，如戊环唑、BAY14120、双苯三唑醇、糠菌唑、环唑醇、醚唑、烯唑醇、氧唑菌、腈苯唑、喹唑菌酮、氟硅唑、粉唑醇、己唑醇、烯菌灵、酰胺唑、环戊唑醇、环戊唑菌、腈菌唑、稻瘟酯、戊菌唑、啶斑肟、丙氯灵、丙环唑、硅氟唑(simeconazole)、戊唑醇、氟醚唑、三唑酮、唑菌醇、氟菌唑、戊叉唑菌；嘧啶甲醇类，如嘧啶醇、异嘧菌醇、氟苯嘧啶醇；2-氨基嘧啶类，如磺嘧菌灵、甲菌定、乙菌定；吗啉类，如吗菌灵、苯锈啶、丁苯吗啉、螺茂胺、克啉菌；苯胺嘧啶类，如环丙嘧啶、嘧菌胺、二甲嘧菌胺；吡咯类，如拌种咯、氟菌；苯酰胺类，如苯霜灵、呋氨丙灵、甲霜灵、R-甲霜灵、甲呋酰胺、霜灵；苯并咪唑类，如苯菌灵、多菌灵、双乙氧咪唑威、麦穗宁、涕必灵；二甲酰亚胺类，如乙菌利、菌核利、异丙定、甲菌利、杀菌利、烯菌酮；酰胺类，如萎锈灵、呋菌胺、氟酰胺、丙氧灭锈胺、氧化萎锈灵、溴氟唑菌；胍类，如双胍盐、多果定、双胍辛醋酸盐；甲氧基丙烯酸酯类，如腈嘧菌酯、亚胺菌、叉氨苯酰胺、SSF-129、肟菌酯(trifloxystrobin)、啶氧菌酯(picoxystrobin)、BAS 500F(建议名：唑菌胺酯(pyraclostrobin))、BAS520；二硫代氨基甲酸酯类，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、福美锌；N-卤甲基硫代四氢邻苯二甲酰亚胺类，如敌菌丹、克菌丹、抑菌灵、氟菌安、灭菌丹、对甲抑菌灵；铜化合物，如波尔多液、氢氧化铜、王铜、硫酸铜、氧化亚铜、锰铜混剂、喹啉铜；硝基苯酚衍生物类，如敌螨普、异丙消；有机磷衍生物类，如克瘟散、异稻瘟净、稻瘟灵、双氯苯磷、定菌磷、甲基立枯磷；各种其它杀菌剂，如噻二唑素-S-甲基、敌菌灵、杀草有效丹(benthiavalicarb)、灭瘟素、灭螨猛、地茂散、百菌清、cyflufenamid、清菌脲、二氯萘醌、哒菌清、氯硝胺、乙霉威、烯酰吗啉、SYP-LI90(建议名：氟吗啉(flumorph))、二噻农、噻唑菌胺(ethaboxam)、氯唑灵、唑酮菌、咪唑菌酮(fenamidone)、氰菌胺(fenoxanil)、三苯锡基、嘧菌腙、氟啶胺、磺菌胺、环酰菌胺(fenhexamid)、藻菌磷、土菌消、异丙菌胺(iprovalicarb)、IKF-916(氰霜唑(cyazofamid))、春雷霉素、磺菌威、metrafenone、nicobifen、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、苯酰菌胺(zoxamide)(RH7281)。
施用式(I)化合物，或包含至少一种所述化合物的农药组合物的优选方法是叶面施用。施用的频率和量要根据相应病原物的侵染危害风险而定。但是，用式I化合物的液体制剂淋湿植物所在的场所，或向土壤中施用该化合物的固体剂型例如颗粒剂(土壤施用)，这些化合物也可以经土壤通过根部而渗透到植物(内吸作用)。对于水稻作物，这种颗粒剂可施用到漫灌的稻田中。式I化合物也可通过用所述杀菌剂的液体制剂浸泡种子或块茎，或用固体制剂对它们进行包衣而施用于种子(包衣)。
上述制剂[即，含有式I化合物的组合物]，如果需要可包含固体或液体助剂，用公知的方法来制备，一般是将该化合物与添加剂，如溶剂、固体载体和任选的表面活性化合物(表面活性剂)充分混合和/或研磨。
农药制剂通常含有0.1-99％重量，优选0.1-95％重量的式I化合物，含有99.9-1％，优选99.8-5％重量的固体或液体助剂，和0-25％，优选0.1-25％重量的表面活性剂。
施用量通常有利地是每公顷(ha)5g-2kg的活性成分(a.i.)，优选10g-1kg a.i./ha，最优选20g-600g a.i./ha。当被用作浸种剂时，常规剂量为每公斤的种子用10mg-1g活性物质。
尽管商业产品优选被加工成浓缩物的形式，但最终的使用者通常会使用稀释的制剂。
下面的非限制性实施例更详细地举例说明了上述的发明。
                         实施例1
该实施例说明了化合物No.1.5的制备。
向17.4g(0.1mol)(2-异丁基环丙基)苯和80ml乙酸酐的混合物中加入6.0g(0.095mol)硝酸和40ml乙酸酐的溶液，加入的方式使得内部温度恒定保持在-30℃。所得的反应混合物-30℃下搅拌1小时，然后在0℃下搅拌2小时。然后混合物倒入到500ml冰水中，用己烷萃取三次。合并后的己烷相用5％的碳酸氢盐水溶液洗涤两次。有机相经硫酸钠干燥和水泵真空蒸馏出溶剂后，获得粗反应产物。通过硅胶快速色谱(洗脱剂：乙酸乙酯/己烷1∶10)纯化得到10.5g黄色的油状物(对位和邻位硝基异构体的混合物)，其可直接用于下一步骤。将该异构体混合物[由10.5g(0.048mol)的1-(2-异丁基环丙基)-2-硝基苯和1-(2-异丁基环丙基)-4-硝基苯组成]溶解于110ml乙醇中，通过5％Pt/C催化剂氢化45分钟。当到达氢气的理论消耗量后，过滤出催化剂并真空除去溶剂。粗品苯胺异构体混合物通过快速色谱(洗脱剂：乙酸乙酯/己烷1∶2)纯化。
产率：获得6.38g的2-(2-异丁基环丙基)苯胺，黄色的油状物(顺式/反式混合物)。
                         实施例2
该实施例说明了化合物3.17的制备。
将0.35g(0.0018mol)1-甲基-4-三氟甲基吡咯-3-甲酸和0.24g(0.0019mol)草酰氯的15ml二氯甲烷溶液在两滴无水DMF存在下室温搅拌3小时。然后将该酰氯溶液缓慢地加入到0.34g(0.0018mol)2-(2-异丁基环丙基)苯胺、0.27g(0.0027mol)三乙胺和10ml二氯甲烷的溶液中。所得的混合物然后在室温下搅拌16小时。真空除去溶剂后，将粗产物溶解在大约100ml乙酸乙酯中。用水洗涤乙酸乙酯相两次并干燥有机相后后，再次通过水泵真空蒸馏出溶剂。粗产物通过快色色谱(洗脱剂：己烷/乙酸乙酯/二氯甲烷1∶2∶2)纯化。
产率：0.52g的1-甲基-4-三氟甲基-1H-吡咯-3-甲酸[2-(2-异丁基环丙基)苯基]酰胺，为白色粉末(顺式/反式混合物)。
                         实施例3
该实施例说明了化合物No.1.10c和1.10t的制备。
步骤1
在磺化烧瓶中，将NaH(12.8g；0.32mol)加入到无水DMSO(600ml)中。在80℃加热90分钟后，室温下分批加入溴化环丙基羰基甲基三苯基鏻(136.5g；0.32mol)。所得的悬浮液室温下搅拌30分钟，然后滴加2-溴苯甲醛(59.4g；0.32mol)的无水DMSO(100ml)溶液。50℃加热所得混合物4小时后，将混合物倒入到2.5升冰水中。用乙酸乙酯萃取，经硫酸钠干燥和水泵真空蒸馏出溶剂后，得到粗产物。通过真空蒸馏进行纯化。
产率：77.6g的E-3-(2-溴苯基)-1-环丙基丙烯酮，黄色的油状物(b.p.：125-130℃/0.3mbar)。
步骤2：
在磺化烧瓶中，将E-3-(2-溴苯基)-1-环丙基丙烯酮(77.6g；0.309mol)和水合肼(23.2g；0.464mol)在乙醇(25ml)中的混合物于回流温度下加热2小时。然后加入粉末状的氢氧化钾(85％)(24.4g；0.37mol)并从烧瓶中蒸馏出过量的水合肼和溶剂。余下的混合物然后在205-210℃的温度下加热3小时。所得的树脂状物在50℃下溶解于乙酸乙酯中并用水洗涤有机相两次。用硫酸钠干燥乙酸乙酯相，通过水泵真空蒸馏出溶剂得到粗产物，通过硅胶快速色谱(洗脱剂：己烷/二氯甲烷7∶1)纯化。
产率：61.2g的2-(2-溴苯基)二环丙基，浅黄色油状物(顺式/反式混合物)。
步骤3
将2-(2-溴苯基)二环丙基(28.5g；0.12mol)、二苯甲酮亚胺(26.1g；0.144mol)、叔丁醇钠(16.1g；0.168mol)、三(二亚苄基丙酮)二钯(Pd2dba3)(0.43g；0.474mmol)、外消旋2，2’-二(二苯基膦基)1，1’-联萘(BINAP)(0.83g；1.34mmol)和无水甲苯(450ml)的混合物在回流温度于氮气氛围下加热6小时。然后通过水泵真空除去溶剂，残余物溶解在乙酸乙酯(750ml)中。有机层用盐水洗涤三次，然后经硫酸钠干燥。溶剂蒸发后获得粗产物。通过硅胶快速色谱(洗脱剂：己烷/二氯甲烷5∶1)进行纯化。
产率：39.9g二苯亚甲基(2-二环丙基-2-基苯基)胺的顺/反-混合物，棕色的油状物。
步骤4：
在磺化烧瓶中，将盐酸羟胺(0.35g；0.0048mol)、乙酸钠(0.53g；0.0064mol)和无水甲醇(30ml)在室温下搅拌约15分钟。然后滴加二苯亚甲基(2-二环丙基-2-基苯基)胺(0.9g；0.00267mol)的甲醇(15ml)溶液。所得的混合物室温下搅拌1小时。用乙酸乙酯(250ml)稀释后，用水洗涤有机相两次。干燥有机相(硫酸钠)并通过水泵真空蒸馏出溶剂后，获得粗产物。最后利用快速色谱(洗脱剂：己烷/乙酸乙酯5∶1)纯化和分离顺式和反式异构体。
产率：0.21g的反式-和0.15g的顺式-2-二环丙基-2-基苯胺，为棕色的油状物。
                         式(I)化合物的剂型实施例
制备式I化合物的剂型如乳油、液剂、颗粒剂、粉剂和可湿性粉剂的加工方法在WO97/33890中描述。
                         生物实施例：杀真菌活性
实施例B-1：对隐匿柄锈菌(Puccinia recodita)/小麦(小麦叶锈病)的活性
生长一周的小麦植株cv.Arina在喷雾室中用加工好的供试化合物(0.02％的活性成分)进行处理。施用后一天在供试的小麦植株上通过喷施孢子悬浮液(1×105个夏孢子/ml)接种。植株在20℃、95％相对湿度的条件下经过2天的孵育期后，再在20℃和60％相对湿度的温室条件下保持8天。接种后10天评估发病率。
在该实验中，表2、3、4和5中的化合物表现出了良好的活性(＜20％受到侵染)。使用化合物2.5、2.17、2.18、2.23、2.24、2.33、2.45、2.46t、2.76c、2.76t、2.77c、2.77t、3.5、3.17、3.23、3.33、3.45、3.76、4.10、4.12、4.26、5.5、5.12、5.21c和5.37c中的每一种实际上完全防止了侵染(0-5％受到侵染)。
实施例B-2：时白叉丝单囊壳菌(Podosphaeral leucotricha)/苹果(苹果白粉病)的活性
生长五周的苹果苗cv.McIntosh在喷雾室中用加工好的供试化合物(0.002％的活性成分)进行处理。施用后一天在上述供试苹果植株上通过抖动被苹果白粉病菌侵染的植物接种。在22℃、60％相对湿度，于14/10小时(白昼/黑暗)的光照条件下，经过12天的孵育期后，评估发病率。
在该实验中，表2、3和4中的化合物表现出了良好的活性。化合物2.5、2.17、2.18、2.23、2.24、2.33、2.45、2.46t、3.5、3.17、3.23、3.33、3.45、4.10和4.12中的每一种表现出强大的效果(＜20％受到侵染)。
实施例B-3：对苹果黑星菌(Venturia inaeqmalis)/苹果(苹果疮痂病)的活性
生长四周的苹果苗cv.McIntosh在喷雾室中用加工好的供试化合物(0.02％的活性成分)进行处理。施用后一天在供试的苹果植株上喷施孢子悬浮液(4×105个分生孢子/ml)进行接种。植株在21℃、95％相对湿度的条件下孵育4天后，再在21℃、60％相对湿度的温室条件下放置4天。再在21℃、95％相对湿度的条件下经过4天的孵育期后评估发病率。
在该实验中，表2和3中的化合物表现出了良好的活性。化合物2.5、2.17、2.18、2.23、2.24、2.33、2.45、2.46t、3.5、3.17、3.23、3.33和3.45中的每一种表现出优异的效果(＜20％受到侵染)。
实施例B-4：对禾谷白粉菌(Erysiphe graminis)/大麦(大麦白粉病)的活性
生长一周的大麦植株cv.Express在喷雾室中用加工好的供试化合物(0.02％的活性成分)进行处理。施用后一天在供试的上述大麦植株上通过抖动被侵染植物上的白粉病菌来接种。在20℃/18℃(白天/黑夜)和相对湿度60％的温室条件下，经过6天的孵育期后评估发病率。
在该实验中，表2、3和4中的化合物表现出了良好的活性。化合物2.5、2.17、2.18、2.23、2.24、2.45、2.46t、2.77c、2.77t、3.5、3.17、3.23、3.45、4.10和4.12中的每一种表现出强大的效果(＜20％受到侵染)。
实施例B-5：时灰葡萄孢菌(Botrytis cinerea)/苹果(苹果灰霉病)的活性
在苹果cv.Golden Delicious的果实上钻3个孔，每孔滴入30μl加工好的供试化合物(0.002％的活性成分)。施用后2小时用吸管吸50μl灰葡萄孢菌的孢子悬浮液(4×105个分生孢子/ml)滴到施用部位。在22℃的生长室中经过7天的孵育期后评估发病率。
在该实验中，表2、3、4、5和6中的化合物表现出了良好的活性。化合物2.5、2.17、2.18、2.23、2.24、2.33、2.45、2.46t、2.76c、2.76t、2.77c、2.77t、3.5、3.17、3.23、3.33、3.76、3.45、3.76、4.10、4.12、4.26、5.5、5.12、5.21c和5.37c中的每一种表现出非常强的效果(＜10％受到侵染)。
实施例B-6：对灰葡萄孢菌(Botrytis cinerea)/葡萄(葡萄灰霉病)的活性
生长五周的葡萄苗cv.Gutedel在喷雾室中用加工好的供试化合物(0.002％的活性成分)进行处理。施用后2天在供试的葡萄植株上喷施孢子悬浮液(1×106个分生孢子/ml)。在21℃、95％相对湿度的温室条件下，经过4天的孵育期后评估发病率。
在该实验中，表2、3、4、5和6中的化合物表现出了良好的活性。化合物2.5、2.17、2.18、2.23、2.24、2.45、2.46t、2.76c、2.76t、2.77c、2.77t、3.5、3.17、3.23、3.33、3.39、3.76、4.10、4.12、4.26、5.5、5.12、5.21c和5.37c中的每一种表现出非常强的效果(＜10％受到侵染)。
实施例B-7：对灰葡萄孢菌(Botrytis cinerea)/番茄(番茄灰霉病)的活性
生长四周的番茄植株cv.Roter Gnom在喷雾室中用加工好的供试化合物(0.002％的活性成分)进行处理。施用后2天在供试番茄植株上喷施孢子悬浮液(1×105个分生孢子/ml)来进行接种。在20℃和95％相对湿度的生长室中，经过4天的孵育期后评估发病率。
在该实验中，表2、3、4、5和6中的化合物表现出了良好的活性。化合物2.5、2.17、2.18、2.23、2.24、2.33、2.45、2.46t、2.76c、2.76t、2.77c、2.77t、3.5、3.17、3.23、3.39、3.45、3.76、4.10、4.12、4.26、5.5、5.12、5.21c和5.37c中的每一种表现出非常强的效果(＜10％受到侵染)。
实施例B-8：对圆核腔菌(Pyrenophora teres)/大麦(大麦网斑病)的活性
生长一周的大麦植株cv.Express在喷雾室中用加工好的供试化合物(0.002％的活性成分)进行处理。施用后2天向供试的大麦植株上喷施孢子悬浮液(3×104个分生孢子/ml)来接种。植株在20℃和95％相对湿度的条件下孵育2天后，将植株保持在20℃和60％相对湿度的温室条件下2天。接种后4天评估发病率。
在该实验中，表2、3、4、5和6中的化合物表现出了良好的活性。化合物2.5、2.17、2.18、2.23、2.24、2.33、2.45、2.46t、2.76c、2.76t、2.77c、2.77t、3.5、3.17、3.23、3.39、3.45、3.76、4.10、4.12、4.26、5.5、5.12、5.21c和5.37c中的每一种表现出非常强的效果(＜20％受到侵染)。
实施例B-9：对颖枯壳针孢菌(Septoria nodorum)/小麦(小麦颖枯病)的活性
生长一周的小麦植株cv.Arina在喷雾室中用加工好的供试化合物(0.02％的活性成分)进行处理。施用后一天在供试的小麦植株上喷施孢子悬浮液(5×105个分生孢子/ml)进行接种。植株在20℃和95％相对湿度的条件下经过1天的孵育期后，将植株保持在20℃和60％的相对湿度的温室中10天。接种后11天评估发病率。
在该实验中，表2、3和4中的化合物表现出了良好的活性。化合物2.5、2.17、2.18、2.23、2.24、2.33、2.45、2.46t、2.76c、2.76t、2.77c、2.77t、3.5、3.17、3.23、3.33、3.39、3.45、3.76、4.10和4.12中的每一种表现出较强的效果(＜20％受到侵染)。

Claims (5)

1.式(I)的化合物：
Figure C038051720002C1
Het是吡咯基、吡唑基或噻唑基，各自被基团R4、R5和R6取代；R1是氢；R2是氢；R3是C2-12烷基、C3-12环烷基、被C1-3烷基取代的C3-12环烷基或被卤素取代的苯基；以及R4、R5和R6独立的选自氢、卤原子、C1-4烷基、C1-4卤代烷基和C1-4烷氧基-C1-4烷基，条件是R4、R5和R6中的至少一个不是氢。
2.权利要求1所述的式(I)化合物，其中R3是C2-6烷基、C3-8环烷基、被C1-3烷基取代的C3-8环烷基或被卤素取代的苯基。
3.式(II)的化合物：
其中R3如权利要求1中所定义。
4.一种防治微生物和预防其危害和侵染植物的组合物，其中的活性成分是权利要求1所述的式(I)化合物以及适合的载体。
5.一种防治或预防植物病原微生物侵染作物的方法，包括将权利要求1所述的式(I)化合物施用于植物、其部分或其所在的场所。
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