CN1117074C - 苄胺肟衍生物、制备它们的中间产物和方法以及它们作为杀真菌剂的用途 - Google Patents

苄胺肟衍生物、制备它们的中间产物和方法以及它们作为杀真菌剂的用途 Download PDF

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CN1117074C
CN1117074C CN98809266A CN98809266A CN1117074C CN 1117074 C CN1117074 C CN 1117074C CN 98809266 A CN98809266 A CN 98809266A CN 98809266 A CN98809266 A CN 98809266A CN 1117074 C CN1117074 C CN 1117074C
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benzamidoxime
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K·艾肯
J·莱恩海默
F·威特里希
E·阿莫曼
G·洛兰兹
S·斯特拉斯曼
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Abstract

本发明涉及式I的苄胺肟衍生物，其中R1是二氟甲基或三氟甲基；R2是氢或氟；R3是可以被氰基取代的C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基-C1-C4-烷基、C3-C6-链烯基、C3-C6-卤代烯基、C3-C6-炔基、C3-C8-环烷基-C1-C4-烷基；R4是苯基-C1-C6-烷基，其苯环上可以携带一个或多个选自卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基的取代基，或者是噻吩基-C1-C4-烷基，其噻吩环上可以携带一个或多个选自卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基的取代基，或者是吡唑基-C1-C4-烷基，其吡唑环上可以携带一个或多个选自卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基的取代基。本发明还涉及制备它们的中间产物以及它们作为杀真菌剂的应用。

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苄胺肟衍生物、制备它们的中间产物和方法以及 它们作为杀真菌剂的用途
本发明涉及新苄胺肟衍生物、制备它们的中间产物和方法以及它们作为杀真菌剂的用途。
JP-A 02/006453描述了杀真菌活性的苄胺肟衍生物，然而其不是完全令人满意的，特别是在低的施用量下。
本发明的目的是提供一种新型的苄胺肟，其具有增强的活性，特别是甚至在低的施用量下。
我们惊奇地发现通过式I的苄胺肟衍生物可以实现本发明的目的，
Figure C9880926600041
其中R1是二氟甲基或三氟甲基；R2是氢或氟；R3是可以被氰基取代的C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基-C1-C4-烷基、C3-C6-链烯基、C3-C6-卤代烯基、C3-C6-炔基、C3-C8-环烷基-C1-C4-烷基；R4是苯基-C1-C6-烷基，其苯环上可以携带一个或多个选自卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基的取代基，或者
是噻吩基-C1-C4-烷基，其噻吩环上可以携带一个或多个选自卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基的取代基，或者
是吡唑基-C1-C4-烷基，其吡唑环上可以携带一个或多个选自卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基的取代基。
在取代基R1至R4的定义中，所使用的术语是用于一组化合物的集合术语。
卤素在每种情况下是氟、氯、溴或碘，特别是氟或氯。
其它含义例如是：
-C1-C4-烷基：甲基、乙基、正丙基、1-甲基乙基、正丁基、1-甲基丙基、2-甲基丙基或1，1-二甲基乙基，特别是乙基；
-C1-C4-卤代烷基：部分或全部被氟、氯、溴和/或碘取代的上述C1-C4-烷基，例如三氯甲基、三氟甲基、2-氟乙基、2-氯乙基、2-溴乙基、2，2-二氟乙基、2，2，2-三氟乙基、2，2，2-三氯乙基、2-氟丙基、3-氟丙基、2-氯丙基或3-氯丙基，特别是2-氟乙基或2-氯乙基；
-氰基-C1-C4-烷基：例如氰基甲基、1-氰基乙-1-基、2-氰基乙-1-基、1-氰基丙-1-基、2-氰基丙-1-基、3-氰基丙-1-基、1-氰基丙-2-基或2-氰基丙-2-基，特别是氰基甲基或2-氰基乙基。
-C1-C4-烷氧基：甲氧基、乙氧基、正丙氧基、1-甲基乙氧基、正丁氧基、1-甲基丙氧基、2-甲基丙氧基或1，1-二甲基乙氧基，特别是甲氧基或乙氧基；
-C1-C4-烷氧基-C1-C4-烷基：被如上所述的C1-C4-烷氧基取代的C1-C4-烷基，例如甲氧基甲基、乙氧基甲基、正丙氧基甲基、(1-甲基乙氧基)甲基、正丁氧基甲基、(1-甲基丙氧基)甲基、(2-甲基丙氧基)甲基、(1，1-二甲基乙氧基)甲基、2-(甲氧基)乙基或2-(乙氧基)乙基，特别是甲氧基甲基或2-甲氧基乙基；
-C3-C6-链烯基：例如丙-2-烯-1-基、正-丁烯-4-基、1-甲基丙-2-烯-1-基、2-甲基丙-2-烯-1-基或2-丁烯-1-基，特别是丙-2-烯-1-基；
-C3-C6-卤代烯基：部分或全部被氟、氯、溴和/或碘取代的上述C3-C6-烯基，例如2-氯烯丙基、3-氯烯丙基、2，3-二氯烯丙基或3，3-二氯烯丙基，特别是2-氯烯丙基；
-C3-C6-炔基：例如丙-1-炔-1-基、丙-2-炔-1-基、正丁-1-炔-1-基、正丁-1-炔-3-基、正丁-1-炔-4-基或正丁-2-炔-1-基，特别是丙-2-炔-1-基；
-C3-C8-环烷基-C1-C4-烷基：例如环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、(环丙基)乙基、1-(环丁基)乙基、1-(环戊基)乙基、1-(环己基)乙基、1-(环庚基)乙基，1-(环辛基)乙基、2-(环丙基)乙基或2-(环丁基)乙基，特别是环戊基甲基；
-苯基-C1-C6-烷基：例如苄基、1-苯基乙基、2-苯基乙基、1-苯基丙-1-基、2-苯基丙-1-基、3-苯基丙-1-基，特别是苄基或2-苯基乙基；
-噻吩基-C1-C4-烷基：例如2-噻吩基甲基、3-噻吩基甲基或2-噻吩基乙基；
-吡唑基-C1-C4-烷基：例如1-吡唑基甲基、2-吡唑基甲基、3-吡唑基甲基或2-吡唑基乙基。
已经证明其中取代基R1是二氟甲基，取代基R3是环丙基甲基和取代基R4是在苯环上可携带一至三个上述取代基，特别是一至三个选自氟、氯、甲基、甲氧基和三氟甲基的苄基的化合物是特别有效的。
其中R1至R4具有下表1所示的含义的式I化合物是特别优选的。表1
    Nr.     R1     R2     R3     R4 熔点℃
    I.1     CHF2     H     C2H5     C6H5-CH2 油状物
    I.2     CHF2     H     C2H5     4-CH3O-C6H4-CH2 油状物
    I.3     CHF2     H     CH2-CH＝CH2     C6H5-CH2 油状物
    I.4     CHF2     H     CH2-C≡CH     C6H5-CH2 油状物
表1
  Nr.     R1     R2   R3     R4   熔点℃
  I.1     CHF2     H   C2H5     C6H5-CH2   油状物
  I.2     CHF2     H   C2H5     4-CH3O-C6H4-CH2   油状物
  I.3     CHF2     H   CH2-CH＝CH2     C6H5-CH2   油状物
  I.4     CHF2     H   CH2-C≡CH     C6H5-CH2   油状物
  I.5     CHF2     H   CH2-C≡CH     4-CH3O-C6H4-CH2   油状物
  I.6     CHF2     H   cPr     C6H5-CH2
  I.7     CF3     H   cPr     C6H5-CH2
  I.8     CHF2     H   cPr     4-F-C6H4-CH2   75-77
  I.9     CHF2     H   cPr     4-Cl-C6H4-CH2   81-83
  I.10     CHF2     H   cPr     4-CH3O-C6H4-CH2   57-59
  I.11     CHF2     H   cPr     4-CF3-C6H4-CH2
  I.12     CHF2     H   cPr     2-噻吩基甲基   油状物
  I.13     CHF2     H   cPr     3-噻吩基甲基   油状物
  I.14     CHF2     H   cPr     吡唑基-1-甲基
  I.15     CHF2     H   cPr     4-CH3-C6H4-CH2
  I.16     CHF2     5-F   CH2-CH＝CH2     C6H5-CH2
  I.17     CHF2     5-F   CH2-CH＝CH2     4-CH3-C6H4-CH2
  I.18     CHF2     5-F   CH2-C≡CH     C6H5-CH2
  I.19     CHF2     5-F   CH2-C≡CH     4-CH3O-C6H4-CH2
  I.20     CHF2     5-F   cPr     C6H5-CH2   62-65
  I.21     CHF2     5-F   cPr     4-F-C6H4-CH2   64-67
  I.22     CHF2     5-F   cPr     4-Cl-C6H4-CH2   72-75
  I.23     CHF2     5-F   cPr     4-CH3-C6H4-CH2   74-76
  I.24     CHF2     5-F   cPr     4-CH3O-C6H4-CH2   79-81
  I.25     CHF2     5-F   cPr     4-CF3-C6H4-CH2
  I.26     CF3     5-F   cPr     C6H5-CH2
  I.27     CHF2     4-F   cPr     C6H5-CH2
  I.28     CHF2     4-F   cPr     4-CH3O-C6H4-CH2
  I.29     CHF2     H   cPr     4-CH3-C6H4-CH2   69-71
  I.30     CHF2     H   CH2-C≡CH     4-F-C6H4-CH2   74-76
  I.31     CHF2     H   C2H5     4-F-C6H4-CH2   油状物
  I.32     CHF2     H   CH2-CH＝CH2     4-F-C6H4-CH2   油状物
  I.33     CHF2     H   CH2-CH＝CH2     4-CH3O-C6H4-CH2   油状物
  I.34     CHF2     H   CH2-CH(CH3)2     C6H5-CH2   65-67
  I.35     CHF2     H   CH2-C(CH3)＝CH2     C6H5-CH2   油状物
在上表中，cPr是环丙基甲基。
在上表中，cPr是环丙基甲基。
本发明式I的苄胺肟衍生物是通过本发明的方法获得的，在该方法中，式II的氟代苄腈进行醚裂开，在碱性介质中(优选在碱金属氢氧化物的存在下)，获得的苄腈III与卤代烷烃CHmFnHal(m是0或1，n是2或3)，例如CHF2Cl或CF3I，反应，获得苄腈IV，随后IV与羟胺或其盐在碱的存在或不存在下，在含水溶液，优选在水或水/醇混合物中反应，获得式V的苄胺肟，然后以本身已知的方式使其烷基化，获得前体VI。
然后以本身已知的方式，使用适合的酰基卤，优选适合的酰基氯，通过在惰性溶剂中加热(优选从20至100℃)来使苄胺肟VI酰化。
特别适合的惰性溶剂是烃或醚，特别优选是芳族烃，例如可提及的二个实例是甲苯或二甲苯。上述反应式中R1是基团CHmFn，其中m是0或1，n是2或3。
上述反应式中给出的中间产物，即其中R2是氟的式III中间产物以及式IV、V和VI的中间产物均是新的，同样也构成本发明主题的一部分。
可从2，3-二氟-6-甲氧基苯甲醛(其例如可以通过WO 97/03071的实施例27的方法制备)出发来制备这些具有二氟取代基的新中间产物，其中采用实施例2中描述的方案进行到化合物IV的步骤。进一步制备相应化合物V和VI的步骤是本领域专业人员本身已知的。
式IV、V和VI的优选化合物是那些其中R2和R3(化合物VI)具有上述式I化合物中给出的含义的化合物。
优选的式IV化合物是下表2中给出的化合物(m和n具有上述含义)。
Nr.  R2  m  n  Fp.[℃]，NMR(CDCl3)ppm
II.1  H  1  2  6,7t(1H)；7,05-7,2m(2H)；7,55-7,7m(1H)
II.2  5-F  1  2  6,65t(1H)；7,05-7,2m(1H)；7,4-7,5m(1H)
II.3  4-F  1  2
II.4  H  0  3
II.5  5-F  0  3
优选的式V化合物列于表3中。
 Nr.  R2  m  n  Fp.[℃]，NMR(CDCl3)ppm
 III.1  H  1  2 5,9s(2H)；7,0-7,2m(2H)；7,15t(1H)；7,4-7,55m(1H)
 III.2  5-F  1  2 4,9s(2H)；6,5t(1H)；6,95-7,05m(1H)；7,15-7,3m(1H)；8,0s(1H)
 III.3  4-F  1  2
 III.4  H  0  3
 III.5  5-F  0  3
一些优选的式VI化合物列于下表4中。
Nr.  R2  R3  m  n  Fp.[℃]，NMR(CDCl3)ppm
IV.1  H  C2H5  1  2
IV.2  H  CH2-CH＝CH2  1  2
IV.3  H  CH2-C≡CH  1  2
IV.4  H  c-Pr  1  2 0,3m(2H)；0,55m(2H)；1,2m(1H)；3,9d(2H)；4,85s，br(2H)；6；6t(1H)；6,85-7,1m(2H)；7,35-7,45m(1H)
IV.5  H  CH2-C≡CH  0  3
IV.6  H  c-Pr  0  3
IV.7  5-F  C2H5  1  2
IV.8  5-F  CH2-CH＝CH2  1  2
IV.9  5-F  CH2-C≡CH  1  2
IV.10  5-F  c-Pr  1  2 0,3m(2H)；0,55m(2H)；1,2m(1H)；3,85d(2H)；4,9s br(2H)；6,55t(1H)；7,0-7,1m(1H)；7,15-7,2m(1H)
化合物I对广谱的植物病原真菌均有优异活性，特别是对属于子囊菌纲、担子菌纲、半知菌纲和藻状菌纲的真菌。这些化合物中某些内吸地起作用，且因此可以作为叶面和土壤杀真菌剂使用。
通常，通过喷雾或撒粉给植物施用活性化合物，或者用活性化合物处理植物的种子。
这些制剂通过本身已知的方式，例如通过活性化合物与溶剂和/或载体混合，如果需要，通过使用乳化剂和分散剂来制备。如果所使用的稀释剂是水，也可以用其它的有机溶剂作助溶剂。适合的辅助剂主要是溶剂，如芳族化合物(例如二甲苯)、氯代芳族化合物(例如氯苯)、石蜡(例如石油馏份)、醇类(例如甲醇、丁醇)、酮类(例如环己酮)、胺类(例如乙醇胺、二甲基甲酰胺)和水；载体如研碎的天然矿物质(例如高岭土、矾土、滑石、白垩)和研碎的合成矿物质(例如细分散的二氧化硅、硅酸盐)；乳化剂如非离子和阴离子乳化剂(例如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)和分散剂如木质素亚硫酸盐废液或甲基纤维素。
适合的表面活性物质是芳族磺酸，例如木素磺酸、苯酚磺酸、萘磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐；脂肪酸的碱金属盐、碱土金属盐和铵盐；烷基磺酸盐和烷基芳基磺酸盐；烷基硫酸盐、月桂基醚硫酸盐和脂肪醇硫酸盐；和硫酸化的十六烷醇、十七烷醇和十八烷醇的盐，或者脂肪醇乙二醇醚的盐；磺化萘和其衍生物与甲醛的缩合产物，萘或萘磺酸与苯酚和甲醛的缩合产物，聚氧乙烯辛基苯酚醚、乙氧基化的异辛基苯酚、辛基苯酚或壬基苯酚，烷基苯酚聚乙二醇醚，三丁基苯基聚乙二醇醚，烷基芳基聚醚醇，异十三烷醇、脂肪醇/环氧乙烷缩合物，乙氧基化蓖麻油，聚氧乙烯烷基醚或聚氧丙烯烷基醚，月桂醇聚乙二醇醚乙酸酯、山梨醇酯，木素亚硫酸盐废液或甲基纤维素。
粉剂、撒施材料和喷粉剂可以通过将活性物质与固体载体混合或一起研磨而生产。
颗粒剂例如包衣、浸渍和匀质颗粒可以通过将活性物质粘合在固态载体上来制备。固态载体是矿质土类如硅胶、二氧化硅、硅胶、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、陶土、白云石、硅藻土、硫酸钙和硫酸镁、氧化镁、磨细的合成材料和肥料，如硫酸铵、磷酸铵、硝酸铵、尿素和植物产品如谷类作物粉末、树皮、木材和坚果壳粉，纤维素粉末或其他固态载体。
这些制剂的实例是：I.90重量份的本发明化合物I与10重量份的N-甲基-2-吡咯烷酮的溶液，该溶液适合以微小雾滴的形式使用。II.10重量份的本发明化合物I、70重量份的二甲苯、10重量份的8至10摩尔环氧乙烷与1摩尔油酸N-单乙醇酰胺的加成物、5重量份的十二烷基苯磺酸钙盐和5重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加成物的混合物；将该溶液细分散在水中获得分散液。III.10重量份的本发明化合物I、40重量份的环己酮、30重量份的异丁醇、20重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加成物组成的水分散液。IV.10重量份的本发明化合物I、25重量份的环己醇、55重量份沸点是210至280℃的石油馏份和10重量份40摩尔环氧乙烷与1摩尔蓖麻油的加成物组成的水分散液。V.将80重量份的本发明化合物I(优选固体形式)与3重量份的二异丁基萘-2-磺酸钠盐、10重量份的来源于亚硫酸盐废液的木素磺酸钠盐和7重量份的粉状硅胶彻底混合，且在锤磨中磨碎混合物，通过将该混合物细分散在水中获得喷雾混合物；VI.将3重量份的本发明化合物I与97重量份的细粉碎的高岭土均匀混合，由此获得喷粉剂，它包含3重量％的活性成分。VII.30重量份的本发明化合物I、62重量份的粉状的硅胶和8重量份预先喷涂到硅胶表面上的石蜡油的均匀混合物；得到具有良好粘性的活性成分的制剂。VIII.40重量份的本发明化合物I、10重量份的苯酚磺酸/脲/甲醛缩合物的钠盐、2重量份硅胶和48重量份水组成的稳定的水分散液，该分散液可以进一步稀释；IX、20重量份的本发明化合物I、2重量份的十二烷基苯磺酸钙、8重量份的脂肪醇聚乙二醇醚、20重量份的苯酚磺酸/脲/甲醛缩合物的钠盐和50重量份的石蜡矿物油组成的稳定油性分散液。
这些新化合物对广谱的植物病原真菌均有优异活性，特别是对属于子囊菌纲、担子菌纲、半知菌纲和藻状菌纲的真菌。这些化合物中某些内吸地起作用，且可以作为叶面和土壤杀真菌剂使用。
它们在防治各种作物如小麦、黑麦、大麦、燕麦、稻、玉米、草坪、棉花、大豆、咖啡、甘蔗、葡萄、水果、观赏植物和蔬菜(例如，黄瓜、菜豆和胡芦科)以及这些作物的种子上的许多真菌方面特别重要。
这些化合物可以通过用杀真菌有效量的活性成分处理真菌或意欲保护使之免受真菌感染的种子、植物、材料或土壤而使用。
施用是在材料、植物或种子受真菌感染前或后进行。
这些新化合物特别适合于防治下列植物病害：
禾谷类上的禾白粉菌(Erysiphe graminis)、葫芦科上的二孢白粉菌(Erysiphe cichoracearum)和苍耳单丝壳菌(Sphaerothecafuliginea)、苹果上的苹果白粉病菌(Podosphaera leucotricha)、葡萄上的葡萄钩丝壳(Uncinula necator)，禾谷类上的柄锈菌(Puccinia)、棉花和草坪上的丝核菌(Rhizoctonia)、禾谷类和甘蔗上的黑粉菌(Ustilago)、苹果上的苹果黑星菌(Venturia inaequalis)、禾谷类上的长蠕孢菌(Helminthosporium)、小麦上的颖枯病菌(Septoria nodorum)、草莓、蔬菜、观赏植物和葡萄上的灰霉菌(Botryti scinerea)、花生上的花生尾孢菌(Cercosporaarachidicola)、小麦和大麦上的眼斑病菌(Pseudocercosporellaherpotrichoides)、稻上的稻梨孢(Pyricularia oryzae)、马铃薯和蕃茄上的致病疫霉(Phytophthora infestans)、各种植物上的镰刀菌(Fusarium)和轮枝孢菌(Verticillium)、葡萄上的葡萄生单轴霉(Plasmopara viticola)、蔬菜和水果上的链格孢菌(Alternaria).
该新化合物也可以在材料(例如木材)保护中使用，例如防治多变拟青霉(Paecilomyces variotii)。
通常，杀真菌组合物包括0.1至95，优选0.5至90重量％的活性化合物。
根据所需的效果类型，施用量是0.025至2，优选0.1至1千克活性化合物/公顷。
在处理种子时，活性化合物的一般需要量是0.001至50克，优选0.01克至10克/千克种子。
在作为杀真菌剂使用时，本发明组合物也可以与其它活性成分一同存在，例如与除草剂、杀虫剂、生长调节剂、杀真菌剂或化肥一同存在。
在大多数情况下，与杀真菌剂的混合物产生更宽的杀真菌作用谱。
下列杀真菌剂可与本发明化合物一起施用，列出它们旨在说明可能的组合，而非旨在限定之：
硫磺，二硫代氨基甲酸盐类及其衍生物，如二甲基二硫代氨基甲酸铁(III)，二甲基二硫代氨基甲酸锌，亚乙基双二硫代氨基甲酸锌，亚乙基双二硫代氨基甲酸锰，乙二胺双二硫代氨基甲酸锰锌，二硫化四甲基秋兰姆，N，N-亚乙基双二硫代氨基甲酸锌的氨配合物，N，N′-亚丙基双二硫代氨基甲酸锌的氨配合物，N，N′-亚丙基双二硫代氨基甲酸锌，N，N′-聚亚丙基双(硫代氨基甲酰基)二硫化物；
硝基衍生物，如二硝基-(1-甲基庚基)苯基巴豆酸酯，2-仲丁基-4，6-二硝基苯基-3，3-二甲基丙烯酸酯，碳酸2-仲丁基-4，6-二硝基苯基-异丙酯，5-硝基间苯二甲酸二异丙酯；
杂环类物质，如2-十七烷基-2-咪唑啉乙酸酯，2，4-二氯-6-(邻-氯苯胺基)-均三嗪，O，O-二乙基邻苯二甲酰亚氨基硫代膦酸酯，5-氨基-1-[双(二甲基氨基)氧膦基]-3-苯基-1，2，4-三唑，2，3-二氰基-1，4-二硫代蒽醌，2-硫代-1，3-二硫杂环戊二烯并[4，5-b]喹喔啉，1-(丁基氨基甲酰基)-2-苯并咪唑氨基甲酸甲酯，2-甲氧基羰基氨基苯并咪唑，2-(2-呋喃基)-苯并咪唑，2-(噻唑基-(4))-苯并咪唑，N-(1，1，2，2-四氯乙硫基)四氢邻苯二甲酰亚胺，N-三氯甲硫基四氢邻苯二甲酰亚胺，N-三氯甲硫基邻苯二甲酰亚胺；
N-二氯氟甲硫基-N′，N′-二甲基-N-苯基硫酸二酰胺，5-乙氧基-3-三氯甲基-1，2，3-噻二唑，2-氰硫基甲硫基苯并噻唑，1，4-二氯-2，5-二甲氧基苯，4-(2-氯苯基亚肼基)-3-甲基-5-异噁唑酮，吡啶-2-硫酮-1-氧化物，8-羟基喹啉或其铜盐，2，3-二氢-5-甲酰苯氨基-6-甲基-1，4-氧硫杂环己二烯，2，3-二氢-5-甲酰苯氨基-6-甲基-1，4-氧硫杂环己二烯-4，4-二氧化物，2-甲基-5，6-二氢-4H-吡喃-3-甲酰苯胺，2-甲基呋喃-3-甲酰苯胺，2，5-二甲基呋喃-3-甲酰苯胺，2，4，5-三甲基呋喃-3-甲酰苯胺，N-环己基-2，5-二甲基呋喃-3-甲酰胺，N-环己基-N-甲氧基-2，5-二甲基呋喃-3-甲酰胺，2-甲基苯甲酰苯胺，2-碘苯甲酰苯胺，N-甲酰基-N-吗啉基-2，2，2-三氯乙基乙缩醛，哌嗪-1，4-亚基双(1-(2，2，2-三氯乙基)甲酰胺，1-(3，4-二氯苯胺基)-1-甲酰氨基-2，2，2-三氯乙烷；
2，6-二甲基-N-十三烷基吗啉及其盐，2，6-二甲基-N-环十二烷基吗啉及其盐，N-[3-(对-叔丁基苯基)-2-甲基丙基]-顺-2，6-二甲基-吗啉，N-[3-(对-叔丁基苯基)-2-甲基丙基]哌啶，1-[2-(2，4-二氯苯基)-4-乙基-1，3-二氧戊环-2-基-乙基]-1H-1，2，4-三唑，1-[2-(2，4-二氯苯基)-4-正丙基-1，3-二氧戊环-2-基乙基]-1H-1，2，4-三唑，N-(正丙基)-N-(2，4，6-三氯苯氧基乙基)-N′-咪唑基脲，1-(4-氯苯氧基)-3，3-二甲基-1-(1H-1，2，4-三唑-1-基)-2-丁酮，(2-氯苯基)-(4-氯苯基)-5-嘧啶甲醇，5-丁基-2-二甲氨基-4-羟基-6-甲基嘧啶，双(对-氯苯基)-3-吡啶甲醇，1，2-双-(3-乙氧基羰基-2-硫脲基)苯，1，2-双-(3-甲氧基羰基-2-硫脲基)苯，[2-(4-氯苯基)乙基]-(1，1-二甲基乙基)-1H-1，2，4-三唑-1-乙醇、1-[3-(2-氯苯基)-1-(4-氟苯基)环氧乙烷-2-基-甲基]-1H-1，2，4-三唑
以及各种杀真菌剂，如十二烷基胍乙酸盐，3-[3-(3，5-二甲基-2-氧基环己基)-2-羟基乙基]戊二酰亚胺，六氯苯，DL-N-(2，6-二甲基苯基)-N-(2-糠酰)-丙氨酸甲酯，DL-N-(2，6-二甲基苯基)-N-(2′-甲氧基乙酰基)丙氨酸甲酯，N-(2，6-二甲基苯基)-N-氯乙酰基-D，L-2-氨基丁内酯，DL-N-(2，6-二甲基苯基)-N-(苯基乙酰基)丙氨酸甲酯，5-甲基-5-乙烯基-3-(3，5-二氯苯基)-2，4-二氧代-1，3-噁唑烷，3-[(3，5-二氯苯基)5-甲基-5-甲氧基甲基]-1，3-噁唑烷-2，4-二酮，3-(3，5-二氯苯基)-1-异丙基氨基甲酰基海因，N-(3，5-二氯苯基)-1，2-二甲基环丙烷-1，2-二甲酰亚胺，2-氰基-[N-(乙基氨基羰基)-2-甲氧基亚氨基]乙酰胺，1-[2-(2，4-二氯苯基)戊基]-1H-1，2，4-三唑，2，4-二氟-α-(1H-1，2，4-三唑基-1-甲基)二苯甲醇，N-(3-氯-2，6-二硝基-4-三氟甲基苯基)-5-三氟甲基-3-氯-2-氨基吡啶，1-((双-(4-氟苯基)甲基甲硅烷基)-甲基)-1H-1，2，4-三唑。
Strobilurins如E-甲氧基亚氨基[α-(邻甲苯氧基)-邻-甲苯基]乙酸甲酯，E-2-{2-[6-(2-氰基苯氧基)嘧啶-4-基氧基]苯基}-3-甲氧基丙烯酸甲酯，N-甲基-E-甲氧基亚氨基-[α-(2，5-二甲基氧基)-邻-甲苯基]乙酰胺。
苯胺基嘧啶类如N-(4，6-二甲基嘧啶-2-基)苯胺，N-[4-甲基-6-(1-丙炔基)嘧啶-2-基]苯胺，N-(4-甲基-6-环丙基嘧啶-2-基)苯胺。
苯基吡咯类如4-(2，2-二氟-1，3-苯并间二氧杂环戊烯-4-基)吡咯-3-腈。
肉桂酰胺类如3-(4-氯苯基)-3-(3，4-二甲氧基苯基)丙烯酰吗啉。
实施例1
a)6-氟-2-羟基苄腈
在干燥氮气下，将7.8克2-甲氧基-6-氟苄腈与18.0克盐酸吡啶在195℃下加热5小时。在冷却之后，将该批料分配在50毫升水和50毫升叔丁基甲基醚中，随后用40毫升2N NaOH萃取有机相。将有机萃取物调节至pH5，随后萃取二次，每次使用40毫升叔丁基甲基醚。在蒸除溶剂之后，获得4.7克所需产物，其是油状物(HPLC：93％)。
NMR(DMSO)ppm：6.8-6.95m(2H)；7.5-7.6m(1H)；11.8s，br(1H).
b)2-二氟甲氧基-6-氟苄腈
在75℃搅拌下，在10.0克2-羟基-6-氟苄腈、50毫升1，2-二甲氧基乙烷和25毫升NaOH(33％)的混合物(使用干冰冷却回流冷凝器)中通入6.3克氯二氟甲烷气体，并且在70至75℃下再搅拌1小时。在冷却之后，用300毫升水稀释，并使用叔丁基甲基醚萃取三次，每次用量是150毫升。在蒸除溶剂之后，获得6.5克所需产物，其是油状物。
NMR(CDCl3)ppm：6.7t(1H)；7.05-7.20m(2H)；755-7.70m(1H).
c)2-二氟甲氧基-6-氟苄胺肟
在75℃下，将6.4克2-二氟甲氧基-6-氟苄腈和3.1克盐酸羟胺、2.6克碳酸钠、7毫升水和35毫升乙醇的混合物搅拌20小时。
在蒸除溶剂之后，将残余物分配到40毫升2N盐酸和20毫升乙酸乙酯中。在分离盐酸相之后，中和至pH7，使用叔丁基甲基醚萃取三次，每次用量是40毫升，蒸除溶剂。获得6.0克所需产物。
NMR(DMSO)ppm：5.9s(2H)；7.0-7.2m(2H)；7.15t(1H)，7.4-7.44m(1H)；9.5s(1H).
d)2-二氟甲氧基-6-氟苯甲酰胺O-环丙基甲基肟
在0至5℃下，在3.0克2-二氟甲氧基-6-氟苄胺肟于30毫升二甲基甲酰胺(DMF)中的溶液中加入0.4克80％纯氢化钠，将该混合物在该温度下搅拌3小时。随后在相同温度下加入1.8克溴环丙基甲烷，在5℃下再搅拌2小时，在室温下搅拌过夜。将该批料搅拌入300毫升水中，使用环己烷萃取三次，每次用量70毫升。在蒸除环己烷之后，获得1.9克所需产物。
NMR(CDCl3)ppm：0.3m(2H)；0.55m(2H)；1.2m(1H)；3.9d(2H)；4.85s，br(2H)；6.6t(1H)；6.85-7.1m(2H)；7.35-7.45m(1H).
e)N-苯乙酰-2-二氟甲氧基-6-氟苯甲酰胺O-环丙基甲基肟(表1的化合物I.6).
将1.9克步骤d)中获得的2-二氟甲氧基-6-氟苯甲酰胺O-环丙基甲基肟和1.5克苯乙酰氯与40毫升甲苯一起回流20小时。在冷却之后，加入40毫升水，将pH调节至11。蒸除溶剂，随后在硅胶上柱色谱纯化残余物(洗脱液是99∶1的环己烷和乙酸乙酯的混合物)，从甲苯相中分离出1.6克所需产物，熔点58至60℃。
NMR(CDCl3)ppm：0.2m(2H)；0.50m(2H)；1.0m(1H)；3.9d(2H)；6.4t(1H)；6.85-7.0m(2H)；7.2-7.5m(6H)；8.5s(1H).
以类似方式获得油状N-苯乙酰-2-二氟甲氧基-6-氟苯甲酰胺O-烯丙基甲基肟(表1的化合物I.3.).
实施例2-制备2-羟基-5，6-二氟苄腈
a)制备2-甲氧基-5，6-二氟苯甲醛肟
在20至25℃下，在搅拌下，将29.4克2-甲氧基-5，6-二氟苯甲醛(根据WO97/03071的实施例27)滴加到16.0克盐酸羟胺、18.9克乙酸钠和110毫升90％甲醇水溶液的混合物中。将该混合物搅拌16小时，蒸除甲醇，使用250毫升水将该混合物拌成浆料，然后洗涤和干燥，获得28.3克所需产物，其熔点是199至201℃。
b)制备2-甲氧基-5，6-二氟苄腈
向18.7克步骤a)中获得的产物于100毫升甲苯的悬浮液中加入20滴二甲基甲酰胺和16.6克亚硫酰二氯，注意温度不能超过30℃。在30℃下搅拌4小时之后，在减压下蒸除甲苯和亚硫酰二氯，并分离出16.5克所需产物，其是油状物。
NMR(CDCl3)ppm：3.9s(3H)；6.65-6.75m(1H)；7.3-7.45m(1H).
c)制备2-羟基-5，6-二氟苄腈
在50℃下，在搅拌下，在23.0克步骤b)获得的产物于70毫升甲苯的溶液中分批加入21.7克AlCl3。在加完之后，在回流下加热该混合物2小时。冷却后，将反应混合物倾倒入350毫升水中，使用2N盐酸调节至pH1。使用叔丁基甲基醚萃取(2×100毫升)获得的粗产物，通过溶解在2N氢氧化钠(2×80毫升)中，并使用2N盐酸将碱相酸化至pH5来进行纯化。使用叔丁基甲基醚(2×80毫升)萃取后，干燥，蒸除溶剂，分离出19.9克所需产物，其是油状物。
NMR(CDCl3)ppm：6.45s，brd(1H)；6.7-6.8m(1H)；7.25-7.4m(1H).
实施例3
抗小麦白粉菌(Erysiphe graminis f.sp.tritici)的效力
将生长在罐中的小麦秧苗(品种：Fruehgold)的叶子用活性化合物的含水制剂喷至滴流，其中该含水制剂是由10％活性成分、63％环己酮和27％乳化剂组成的储备溶液制备的。喷雾液层干燥之后24小时，喷粉小麦白粉菌的孢子。接着，将该试验植株置于20-22℃和75-80％相对湿度的温室中。7天之后目测白粉菌的感染程度(％总叶面积)。
使用包括63ppm的表1中活性成分I.3、I.6、I.8、I.9、I.10、I.12、I.13和I.29的含水制剂处理的植株未感染疾病，而未处理的植株的感染水平是80％。
实施例3
抗小麦白粉菌(Erysiphe graminis f.sp.tritici)的效力
将生长在罐中的小麦秧苗(品种：Fruehgold)的叶子用活性化合物的含水制剂喷至滴流，其中该含水制剂是由10％活性成分、63％环己酮和27％乳化剂组成的储备溶液制备的。喷雾液层干燥之后24小时，喷粉小麦白粉菌的孢子。接着，将该试验植株置于20-22℃和75-80％相对湿度的温室中。7天之后目测白粉菌的感染程度(％总叶面积)。
使用表2中的活性成分II.1和II.3处理的植株未感染疾病，而未处理的植株的感染水平是80％。

Claims (8)

1、式I的苄胺肟衍生物，
Figure C9880926600021
其中取代基具有如下含义：R1是二氟甲基；R2是氢或氟；R3是可以被氰基取代的C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基-C1-C4-烷基、C3-C6-链烯基、C3-C6-卤代烯基、C3-C6-炔基、C3-C8-环烷基-C1-C4-烷基；R4是苯基-C1-C6-烷基，其苯环上可以携带一个或多个选自卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基的取代基，或者
是噻吩基-C1-C4-烷基，其噻吩环上可以携带一个或多个选自卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基的取代基，或者
是吡唑基-C1-C4-烷基，其吡唑环上可以携带一个或多个选自卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基的取代基。
2、权利要求1的式I苄胺肟衍生物，其中R4是在苯环上可以携带一至三个选自卤素、C1-C4-烷基和C1-C4-烷氧基的取代基的苄基。
3、权利要求1的式I苄胺肟衍生物，其中R2是氟且在苯环的5位上。
4、式VI的苄胺肟
Figure C9880926600031
其中R1、R2和R3具有权利要求1中的含义。
5、权利要求4的式VI苄胺肟，其中R2是氟且位于苯环的5位上。
6、权利要求1至3之任一项的式I苄胺肟衍生物的用途，其用于防治有害真菌。
7、杀真菌组合物，其包括杀真菌有效量的至少一种权利要求1至3之任一项的式I苄胺肟衍生物。
8、一种防治有害真菌的方法，其包括使用杀真菌有效量的式I的化合物或权利要求7的含式I的苄胺肟衍生物的组合物处理有害真菌、它们的栖息地或处理欲使其免受这些真菌侵染的植物、空间、表面或材料。
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