CN1065658A - 杀真菌剂 - Google Patents

杀真菌剂 Download PDF

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Publication number
CN1065658A
CN1065658A CN92101184A CN92101184A CN1065658A CN 1065658 A CN1065658 A CN 1065658A CN 92101184 A CN92101184 A CN 92101184A CN 92101184 A CN92101184 A CN 92101184A CN 1065658 A CN1065658 A CN 1065658A
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China
Prior art keywords
alkyl
alkoxyl group
arbitrarily
group
replaces arbitrarily
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CN92101184A
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Inventor
J·M·克拉夫
C·R·A·戈弗雷
P·J·迪弗雷恩
I·R·马修斯
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=26298356&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CN1065658(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from GB919102038A external-priority patent/GB9102038D0/en
Priority claimed from GB919117530A external-priority patent/GB9117530D0/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of CN1065658A publication Critical patent/CN1065658A/zh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D213/63—One oxygen atom
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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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Abstract

本发明涉及具有式(I)结构及其立体异构体的 杀真菌化合物，其中A是氢、卤素、羟基、C1-4烷基、 C1-4烷氧基、C1-4卤代烷基、C1-4卤代烷氧基、 C1-4烷氧羰基、C1-4烷氧基羰基、苯氧基、硝基或氰 基；R1和R2如说明书中所定义；R3和R4相同或不 同，是氢、任意取代的烷基、任意取代的芳烷基、任意 取代的链烯基、任意取代的炔基、任意取代的芳基或 任意取代的杂芳基、或R3和R4连接在一起形成任 意取代的杂环；R5和R6分别是氢或C1-4烷基。

Description

具有式（Ⅰ）：
Figure 921011849_IMG4
及其立体异构体的杀真菌化合物，式中A是具体的小基团或单个原子，R1和R2选自范围广泛的具体的取代基，R5和R6各自是氢或C1-4烷基。
本发明涉及用作杀真菌剂、杀虫剂和杀螨剂的O-甲基氧代亚氨基乙酰胺衍生物，它们的制备方法，含这些衍生物的组合物以及将它们用来抗真菌，特别是植物真菌感染，和消灭或防治昆虫及螨的方法。
本发明提供具有式（Ⅰ）的化合物及其立体异构体，式中A是氢、卤素、羟基、C1-4烷基、C1-4烷氧基、C1-4卤代烷基、C1-4卤代烷氧基、C1-4烷基羰基、C1-4烷氧基羰基、苯氧基、硝基或氰基;R1和R2可以相同或不同，是氢、任意取代的烷基、任意取代环烷基、任意取代的杂环烷基（特别是任意取代的杂芳基烷基）、任意取代的环烷基烷基、任意取代的芳烷基、任意取代的芳氧基烷基、任意取代的杂环氧基烷基（特别是任意取代的杂芳基氧基烷基）、任意取代的链烯基、任意取代的炔基、任意取代的烷氧基、任意取代的芳基、任意取代的杂环基（特别是任意取代的杂芳基）、任意取代的芳氧基、任意取代的杂环氧基（特别是任意取代杂芳基氧基）、硝基、卤素、氰基、-NR3R4、-CO2R3、-CONR3R4、-COR3、-S（D）nR3（其中n是0、1或2）、（CH2）mPO（OR3）2（其中m是0或1），或R1和R2连接在一起形成碳环或杂环体系;R3和R4相同或不相同，是氢、任意取代的烷基、任意取代的芳烷基、任意取代的链烯基、任意取代的炔基、任意取代的芳基或任意取代的杂芳基，或R3和R4连接在一起形成任意取代的杂环;和R5和R6单独是氢或C1-4烷基。
本发明的化合物至少含两个碳-氮双键，有时以几何异构体的形式得到。然而，这些混合物可分离成单独的异构体。本发明包括上述异构体及其各种比率的混合物。
由取代的肟基不对称双键得到的个别异构体通常用符号“E”和“Z”标记。这些符号是根据在文献（参见，例如J  March的“Advanced  Organic  Chemistry”.3rd  edition，Willey-Interscience，Page109  et  seg）中作了充分说明的Cahn-Ingold-Prelog系统定义的。
通常，具有氧代亚氨基乙酰胺基的碳-氮双键的一种异构体，比其他异构体具有更高的杀真菌活性，活性高的异构体通常是（E）异构体。这些（E）异构体，构成本发明优选的实施方案。
卤素包括氟、氯、溴和碘。
烷基及烷氧基、芳烷基和芳氧基烷基的烷基部分可以是直链或支链，除非另有说明，适合含1-6个碳原子。例子是甲基、乙基异丙基和叔丁基。任意的取代基包括卤素（特别是氯和氟）、氰基、羟基、C1-4烷氧基和C1-4烷氧基（C1-4）-烷氧基。取代的烷基和取代的烷氧基的例子是三氟甲基和三氟甲氧基。
适合的环烷基是C3-6环烷基，例如环丙基和环己基，适合的环烷基烷基是C3-6环烷基（C1-4）烷基，例如1-或2-环丙基乙基。任意的取代基包括卤素、烃基和C1-4烷氧基。
适合的直链或支链链烯基和炔基含2-6个碳原子，通常2-4碳原子。例子是乙烯基、烯丙基和炔丙基。取代的链烯基和炔基包括任意取代的芳基和杂芳基链烯基（特别是任意取代的芳基、杂芳基（C2-4）链烯基，尤其是任意取代的苯乙烯基）和芳基炔基。
芳基及芳烷基、芳基链烯基、芳基炔基、芳氧基和芳氧基烷基的芳基部分包括苯基和萘基。
适合的碳环或R1和R2一起可形成的杂环系是C4-10（通常C5-10）脂族、芳香族或混合的脂族/芳香族碳环体系，例如环戊基、环己基、环己二烯基和带有一个或两个任意取代的稠合苯环和/或取代基，例如甲基的上述基团;或其可以是4-10员（通常5-10员）杂环体系，例如四氢吡喃基。
术语“杂环”包括叫做杂芳基团的芳香族杂环基团。杂环或其他基团的杂环部分例如杂环烷基通常是含一个或多个O、N或S杂原子的可稠合到一个或多个其他芳香族或杂芳香族或其他杂环例如苯环上的5员或6员芳族或非芳族环。例子是噻吩基、呋喃基、吡咯基、异噁唑基、噁唑基、吡唑基、咪唑基、三唑基、噻唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、苯并呋喃基、苯并噻吩基、二苯并呋喃基、苯并噻唑基、苯并噁唑基、吲哚基、喹啉基和喹喔啉基，及其合适的N-氧化物。
适合的由R3和R4连接在一起而形成的任意取代的杂环是含1-3个分别选自O、S或N的杂原子和含1-3个取代基（例如是卤素、氰基、硝基、C1-6烷基、C1-6烷氧基、C1-6烷硫基的5-7员杂环，或者是上文所述的杂环。这些杂环的例子是吡咯烷、哌啶、吗啉、硫代吗啉、哌嗪、六亚甲基亚胺、四氢喹啉、四氢异喹啉和2，3-二氢-1;4-苯并噁嗪。
可以在任意取代的芳基和杂环基（包括杂芳基）部分，存在的取代基包括一个或多个下列取代基：卤素、羟基、巯基、C1-4烷基（特别是甲基和乙基）、C2-4链烯基（特别是烯丙基）、C2-4炔基（特别是炔丙基）、C1-4烷氧基（特别是甲氧基）、C2-4链烯氧基（特别是烯丙基氧基）、C2-4炔氧基（特别是炔丙氧基）、卤代（C1-4）烷基（特别是三氟甲基）、卤代（C1-4）烷氧基（特别是三氟甲氧基）、C1-4烷硫基（特别是甲硫基）、羟基（C1-4）烷基、C1-4烷氧基（C1-4）烷基、C1-4烷氧基（C1-4）烷氧基、C3-6环烷基、C3-6环烷基（C1-4）烷基、任意取代的芳基（特别是任意取代的苯基）、任意取代的杂芳基（特别是任意取代的吡啶基或嘧啶基）、任意取代的芳氧基（特别是任意取代的苯氧基）、任意取代的杂芳基氧基（特别是任意取代的吡啶基氧基或嘧啶氧基）、任意取代的芳基（C1-4）烷基（特别是任意取代的苄基、任意取代的苯乙基和任意取代的苯基正丙基），其中烷基部分可用羟基任意取代，任意取代的杂芳基（C1-4）烷基（特别是任意取代的吡啶基或嘧啶（C1-4）烷基）、任意取代的杂基（C2-4）链烯基（特别是任意取代的苯基乙烯基）、任意取代的杂芳基（C2-4）链烯基（特别是任意取代的吡啶基乙烯基或嘧啶基乙烯基）、任意取代的芳基（C1-4）烷氧基（特别是任意取代的苄氧基）、任意取代的杂芳基（C1-4）烷氧基（特别是任意取代的吡啶基或嘧啶基（C1-4）烷氧基）、任意取代的芳氧基（C1-4）烷基（特别是苯氧基甲基）、任意取代的杂芳基氧基（C1-4）烷基（特别是任意取代的吡啶氧基或嘧啶氧基（C1-4）烷基）、酰氧基，包括C1-4链烷酰氧基（特别是乙酰氧基）和苯甲酰氧基、氰硫基、异氰基、氰基、异氰硫基、硝基、-NR′R″、-NHCOR′、-NHCONR′R″、-CONR′R″、-COOR′R″、-COOR′、-OSO2R′、-SO2R′、-COR′、-CR′＝NR″或-N＝CR′R″，其中R′和R″分别是氢、C1-4烷基、C1-4烷氧基、C1-4烷硫基、C3-6环烷基、C3-6环烷基（C1-4）烷基、苯基或苄基，该苯基和苄基用卤素、C1-4烷基或C1-4烷氧基任意取代。
可以在任何一个上述取代基的芳基或杂芳基环中存在的取代基包括一个或多个下列取代基：卤素、羟基、巯基、C1-4烷基、C2-4链烯基、C2-4炔基、C1-4烷氧基、C2-4链烯氧基、C2-4炔氧基、卤代（C1-4）烷基、卤代（C1-4）烷氧基、C1-4烷硫基、羟基（C1-4）烷基、C1-4烷氧基（C1-4）烷基、C3-6环烷基、C3-6环烷基（C1-4）烷基、链烷酰氧基、苯甲酰氧基、氰基、异氰基、硫代氰基、异硫代氰基、硝基、-NR′R″、-NHCOR′、-NHCONR′R″、-CONR′R″、-COOR′、-SO2R′、-OSO2R′、-COR′、-CR′＝NR″或-N＝CR′R″，其中R′和R″具有上述给定的定义。
一方面，本发明包括的式（Ⅰ）化合物，其中A是氢、卤素、羟基、甲基、甲氧基、三氟甲基、三氟甲氧基、C1-2烷基羰基、C1-2烷氧基羰基、苯氧基、硝基或氰基;R1是C1-4烷基、卤代（C1-4）烷基、C1-4烷氧基、卤代（C1-4）烷氧基、C1-4烷基羰基、C1-4烷氧基羰基、氰基、苯基（C1-4）烷基、苯基、含一个或多个O、N或S原子并可任意稠合到苯环上的5员或6员芳族杂环，上述任何一个芳族和杂芳族部分是用一个或多个卤素、羟基、C1-4烷基、卤代（C1-4）烷基、C1-4烷氧基、卤代（C1-4）烷氧基、C1-4烷基羰基、C1-4烷氧基羰基、硝基、氰基、苯基、苯氧基、苄基或苄氧基任意取代的;R2是氢、卤素、C1-4烷基、卤代（C1-4）烷基、C1-4烷基羰基、C1-4烷氧基羰基、氰基或苯基;或R1和R2连接在一起形成C5-10碳环体系。
另一方面，本发明包括的式（Ⅰ）化合物，其中A是氢，或卤素;R1是C1-4烷基、苄基、C1-4烷基羰基、C1-4烷氧基羰基、氰基、苯基、噻吩基、三唑基、噻唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、喹啉基或喹喔啉基，上述任何芳族或杂芳族部分用一个或多个卤素、C1-4烷基、三氟甲基、C1-4烷氧基、三氟甲氧基、硝基、氰基、苯基或苄氧基任意取代;R2是氢、C1-4烷基、C1-4烷基羰基、C1-4烷氧基羰基、氰基或苯基;或R1和R2连接在一起形成任意稠合到苯环上的环戊基或环己基环;R5和6分别是氢或C1-4烷基。
再一方面，本发明包括的式（Ⅰ）化合物，其中A是氢;R1是苯基、噻吩基、呋喃基、吡咯基、咪唑基、三唑基、噻唑基、噁唑基、异噁唑基、吡唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、喹啉基、喹喔啉基、苯并噻唑基、苯并噁唑基、苯并噻吩基或苯并呋喃基，上述任何芳族或杂芳族部分用一个或多个卤素、C1-b烷基、卤代（C1-4）烷基（特别是三氟甲基和三氟乙基）、C1-b烷氧基、氰基（C1-4）烷氧基、卤代（C1-4）烷氧基（特别是三氟甲氧基）、C1-4烷氧基（C1-4）烷基、C1-4烷氧基（C1-4）烷氧基、C1-4烷氧基（C1-4）烷氧基（C1-4）烷氧基、C1-b烷硫基、C2-6链烯基、C2 -6链烯氧基、C2-6炔基、C2-6炔基氧基、硝基、氰基、苯基、苯氧基、苄氧基、CO2R′、CONR′R″、CSNR′R″、NR′R″、S（O）nR′、NHCONR′R″，（其中R′和R″分别是氢或C1-4烷基，和n是0、1或2）任意取代;R2是甲基;R5是氢和R6是甲基;或其适合的N-氧化物。
本发明通过下表Ⅰ、Ⅱ和Ⅲ中列举的化合物进行说明。在这些表中，O-甲基氧代乙酰胺基具有（E）构型。
表1包括式（Ⅰ.1）的350种化合物，式中的R1、R2和A的定义列示在表中。
表1
化合物号 R1R2A
1 2-CH3O-C6H4H H
2 3-CH3O-C6H4H H
3 4-CH3O-C6H4H H
表Ⅰ（续）
化合物号
R1R2A
4 2-CH3-C6H4H H
5 3-CH3-C6H4H H
6 4-CH3-C6H4H H
7 2-F-C6H4H H
8 3-F-C6H4H H
9 4-F-C6H4H H
10 2-Cl-C6H4H H
11 3-Cl-C6H4H H
12 4-Cl-C6H4H H
13 2-Br-C6H4H H
14 3-Br-C6H4H H
15 4-Br-C6H4H H
16 2-NO2-C6H4H H
17 3-NO2-C6H4H H
18 4-NO2-C6H4H H
19 2-CF3-C6H4H H
20 3-CF3-C6H4H H
21 4-CF3-C6H4H H
22 C6H5H H
23 C6H5CH3H
24 C6H5C6H5H
25 2-C6H5-C6H4H H
26 3-C6H5-C6H4H H
27 4-C6H5-C6H4H H
28 2-（C6H5CH2O）-C6H4H H
29 3-（C6H5CH2O）-C6H4H H
30 4-（C6H5CH2O）-C6H4H H
31 2-cyano-C6H4H H
32 3-cyano-C6H4H H
33 4-cyano-C6H4H H
34 2-CF3O-C6H4H H
35 3-CF3O-C6H4H H
表Ⅰ（续）
化合物号
R1R2A
36 4-CF3O-C6H4H H
37  吡啶-2-基  H  H
38  吡啶-3-基  H  H
39  吡啶-4-基  H  H
40 吡啶-2-基 CH3H
41  吡啶-2-基  氰基  H
42 吡啶-2-基 CO2C2H5H
43 吡啶-2-基 CO2CH3H
44  嘧啶-2-基  H  H
45  嘧啶-4-基  H  H
46  噻吩-2-基  H  H
47 噻吩-2-基 CH3H
48  5-Cl-噻吩-2-基  H  H
49 CO2C2H5CO2C2H5H
50 CO2CH3CO2CH3H
51 COCH3COCH3H
52  氰基  氰基  H
53  θ  θ  H
54  θ  θ  H
55  θ  θ  H
56 叔C4H3H H
57 C6H5CH2H H
58 2，4-二-Cl-C6H3H H
59 2，4-二-F-C6H3H H
60 3，5-二-CH3-C6H3H H
61 3，5-二-CH3O-C6H3H H
62 吡嗪-2-基 CH3H
63 6-CH3-吡啶-3-基 CH3H
64 吡啶-2-基 C2H5H
65 吡啶-3-基 CH3H
66 嘧啶5-基 异-C3H7H
67 异C3H7嘧啶-5-基 H
表Ⅰ（续）
化合物号
R1R2A
68 吡啶-4-基 CH3H
69 6-Cl-吡啶-2-基 CH3H
70 5-Cl-吡啶-2-基 CH3H
71 4-Cl-吡啶-2-基 CH3H
72 3-Cl-吡啶-2-基 CH3H
73 6-氰基-吡啶-2-基 CH3H
74 5-氰基-吡啶-2-基 CH3H
75 4-氰基-吡啶-2-基 CH3H
76 3-氰基-吡啶-2-基 CH3H
77 6-Br-吡啶-2-基 CH3H
78 5-Br-吡啶-2-基 CH3H
79 4-Br-吡啶-2-基 CH3H
80 3-Br-吡啶-2-基 CH3H
81 6-CH1-吡啶-2-基 CH3H
82 5-CH3-吡啶-2-基 CH3H
83 4-CH3-吡啶-2-基 CH3H
84 3-CH3-吡啶-2-基 CH3H
85 6-F-吡啶-2-基 CH3H
86 5-F-吡啶-2-基 CH3H
87 4-F-吡啶-2-基 CH3H
88 3-F-吡啶-2-基 CH3H
89 3-CH3-吡嗪-2-基 CH3H
90 3-C2H3-吡嗪-2-基 CH3H
91 3-Cl-吡嗪-2-基 CH3H
92 3-OCH3-吡嗪-2-基 CH3H
93 5-CO2CH2-吡嗪-2-基 CH3H
94 5-CO2C2H5吡嗪-2-基 CH3H
95 3-氰基-吡嗪-2-基 CH3H
96 嘧啶-4-基 CH3H
97 2Cl-嘧啶-4-基 CH3H
98 2-OCH3-嘧啶-4-基 CH3H
99 2-CH3-嘧啶-4-基 CH3H
表Ⅰ（续）
化合物号
R1R2A
100 2-氰基-嘧啶-4-基 CH3H
101 噻唑-2-基 CH3H
102 噻吩-3-基 CH3H
103 5-Cl-噻吩-2-基 CH3H
104 5-CH3-噻吩-2-基 CH3H
105 5-Br-噻吩-2-基 CH3H
106 5-氰基-噻吩-2-基 CH3H
107 3-CH3-噻吩-2-基 CH3H
108 2-OCH3-C6H4CH3H
109 3-OCH3-C6H4CH3H
110 4-OCH3-C6H4CH3H
111 2-CH3-C6H4CH3H
112 3-CH3-C6H4CH3H
113 4-CH3-C6H4CH3H
114 2-F-C6H4CH3H
115 3-F-C6H4CH3H
116 4-F-C6H4CH3H
117 2-Cl-C6H4CH3H
118 3-Cl-C6H4CH3H
119 4-Cl-C6H4CH3H
120 2-Br-C6H4CH3H
121 3-Br-C6H4CH3H
122 4-Br-C6H4CH3H
123 2-NO2-C6H4CH3H
124 3-NO2-C6H4CH3H
125 4-NO2-C6H4CH3H
126 2-CF3-C6H4CH3H
＊127 3-CF3-C6H4CH3H
128 4-CF3-C6H4CH3H
129 2-氰基-C6H4CH3H
130 3-氰基-C6H4CH3H
131 4-氰基-C6H4CH3H
表Ⅰ（续）
化合物号
R1R2A
132 3，4，5-（OCH3）3-C6H2CH3H
133 3，5-二-F-吡啶-2-基 CH3H
134 3，4，5，6-四F-吡啶-2-基 CH3H
135 2，6-二-Cl-吡啶-3-基 CH3H
136 哒嗪-3-基 CH3H
137 哒嗪-4-基 CH3H
138 6-CH3-哒嗪-3-基 CH3H
139 4-氰基-喹啉-2-基 CH3H
140 喹喔啉-2-基 CH3H
141 C6H5CH36-F
142 C6H5CH36-Cl
143 6-CH2-嘧啶-4-基 CH3H
144 4-CH3-嘧啶-5-基 CH3H
145 4-CH3-嘧啶-2-基 CH3H
146 4，6-二-CH3-嘧啶-2-基 CH3H
147 2，6-二-CH3-嘧啶-4-基 CH3H
148 2，4-二-CH3-嘧啶-5-基 CH3H
149 6-Cl-嘧啶-4-基 CH3H
150 6-OCH5-嘧啶-4-基 CH3H
151 4，6-二-OCH3-嘧啶-2-基 CH3H
152  φ  φ  H
153  φ  φ  H
154 N-氧化物-吡啶-2-基 CH3H
155 5-C2H3-吡啶-2-基 CH3H
156 CH3CO CH3H
157 C6H5CO CH3H
158 N-CH1-吡咯-2-基 CH3H
159 4-Cl-喹啉-2-基 CH3H
160 2，4-二-Cl-C6H51，2，4-三唑-1- H
基-CH2-
161 2，4-二-Cl-C6H2吡啶-3-基-CH2H
162 2，4-二-CH3-噻唑-5-基 CH3H
表Ⅰ（续）
化合物号
R1R2A
163 呋喃-2-基 CH3H
164 2，4-di-CH3-呋喃-3-基 CH3H
165  吡啶-2-基  吡啶-2-基  H
166 6-C6H5-嘧啶-4-基 CH3H
167 4-氰基-吡啶-3-基 CH3H
168 1，2，4-三嗪-5-基 CH3H
169 3-CH3-1，2，4-三嗪-5-基 CH3H
170 3-C6H5-1，2，4-三嗪-5-基 CH3H
171 3-SCH3-1，2，4-三嗪-5-基 CH3H
172 3-OCH3-1，2，4-三嗪-5-基 CH3H
173 5-CONH2-吡嗪-2-基 CH3H
174 5-氰基-吡嗪-2-基 CH3H
175 5，6-二-CH3-吡嗪-2-基 CH3H
176 3，5-二-CH3-吡嗪-2-基 CH3H
177 3，6-二-CH3-吡嗪-2-基 CH3H
178 5-CH3-吡嗪-2-基 CH3H
179 6-CH3-吡嗪-2-基 CH3H
180 5-Cl-1吡嗪-2-基 CH3H
181 6-Cl-1吡嗪-2-基 CH3H
182 5，6-二氰基-吡嗪-2-基 CH3H
183 4-SO2CH3-C6H4CH3H
184 4-NH2-C6H4CH3H
185 2，4-二-Cl-C6H3CH3H
186 2，4-二-CH3-C6H3CH3H
187 4-NHCONH2-C6H4CH3H
188 C6H5环丙基 H
189 C6H5Cl H
190 4-C2H5O-C6H4CF3H
191 C6H5SCH3H
192 C6H5F H
193 C6H5OC2H5H
194 C（CH3）3CH3H
表Ⅰ（续）
化合物号
R1R2A
195 环己基-CH2CH3H
196 C6H5-CH2CH3H
197 吡嗪-2-yl-CH2CH3H
198 （E）-C6H5-CH＝CH CH3H
199 C6H5-OCH2CH3H
200 C6H5CH2Cl H
201 苯并噻唑-2-基 CH3H
202 苯并噁唑-2-基 CH3H
203 吡嗪-2-yl C2H5H
204 5-OCH3-吡嗪-2-基 CH3H
205 6-OCH3-吡嗪-2-基 CH3H
206 6-氰基-吡嗪-2-基 CH3H
207 5-cyano-氰基-吡啶-2-基 CH3H
208 6-cyano-氰基-吡啶-3-基 CH3H
209 3-cyano-氰基-吡啶-4-基 CH3H
210 2-cyano-氰基-吡啶-4-基 CH3H
211 嘧啶-5-基 CH3H
212 2-CH3-嘧啶-5-基 CH3H
213 3-OCH3-异噁唑-5-基 CH3H
214 3-Br-异噁唑-5-基 CH3H
215 5-NO2-噻唑-2-基 CH3H
216 5-CH3-噻唑-2-基 CH3H
217 4-CH3-噻唑-2-基 CH3H
218 2-Cl，4-CH3-噻唑-5-基 CH3H
219 3，5-二-OCH3-1，2，4- CH3H
三嗪-6-基
220 3，6-di-CH3-哒嗪-4-基 CH3H
221 2-（C6H5O）-C6H4CH3H
222 3-（C6H5O）-C6H4CH3H
223 4-（C6H5O）-C6H4CH3H
224 1，2，4-三唑-1-基-CH2CH3H
225 C6H5OCH3H
表Ⅰ（续）
化合物号
R1R2A
226 OCH3C6H5H
227 C6H5CH3S（O） H
228 C6H5CH3S（O）2H
229 C6H5N（CH3）2H
230 C6H5O CH3H
231 C6H5Br H
232 C6H5I H
233 C6H5（CH3）2CHS H
234 嘧啶-2-基 CH3O H
235  吡嗪-2-基  Cl  H
236 3-OC2H5-吡嗪-2-基 CH3H
237 吡啶-2-基 SCH3H
238 吡啶-2-基 SO2CH3H
239 吡啶-2-基 SOCH3H
240 3，5-二-CH3-噁唑-4-基 CH3H
241 吡啶-2-基 OCH3H
242 吡啶-2-基 SC2H5H
243 吡啶-2-基 OC6H5H
244 吡啶-2-基 OCH2-C6H5H
245 6-OC2H5-嘧啶-4-基 CH3H
246 吡啶-2-基 NH2H
247 SCH3吡啶-2-基 H
248 2，4-di-F-C6H3CH3H
249 2，4-di-OCH3-C6CH3H
250 5-CH3-嘧啶-2-基 CH3H
251 SO2CH3吡啶-2-基 H
252 吡啶-3-基 SCH3H
253 吡啶-3-基 OCH3H
254 6-CF3-吡啶-2-基 CH3H
255 3-CF3-4-F-C6H3CH3H
256 6-CF3-嘧啶-4-基 CH3H
257 3，5-二-F-C6H3CH3H
表Ⅰ（续）
化合物号
R1R2A
258 2-CH3CH2S-嘧啶-4-基 CH3H
259 2-CF3-嘧啶-4-基 CH3H
260 4-CF3-吡啶-2-基 CH3H
261 2-苯基-噻唑-4-基 CH3H
262 3-NH2C（O）-C6H4CH3H
263 4-CF3-嘧啶-2-基 CH3H
264 3，5-二-CF3-C6H3CH3H
265 2-（2-CN-C6H4-O-）-嘧啶-4-基 CH3H
266 3-n-C3H7O-C6H4CH3H
267 2-CH（CH3）2-O-嘧啶-4-基 CH3H
268 6-CF3-吡嗪-2-基 CH3H
269 4-C2H5O-嘧啶-2-基 CH3H
270 6-C2F5-嘧啶-4-基 CH3H
271 3-CF3O-C6H4CH3H
272 4-CH3O-吡啶-2-基 CH3H
273 2-炔丙氧基-嘧啶-4-基 CH3H
274 2-C2H5O-嘧啶-4-基 CH3H
275 2-烯丙氧基-嘧啶-4-基 CH3H
276 3-CH3O-哒嗪-6-基 CH3H
277 3-C2H5O-哒嗪-6-基 CH3H
278 3-烯丙氧基C6H4CH3H
279 4-CH3S-嘧啶-2-基 CH3H
280 4-CH3O-嘧啶-2-基 CH3H
281 3-CF3-C6H4SCH3H
282 3-CF3-C6H4CF3H
283 3-CF3-C6H4C2H5H
284 3-CF3-C6H4NH2H
285 3-CF3-C6H4咪唑基 H
286 3-CF3-C6H4N（CH3）2H
287 3-CF3-C6H4NHCH3H
288 PO（OC2H5）2CH3H
表Ⅰ（续）
化合物号
R1R2A
289 PO（OC2H5）2C6H5H
290 4-CH3-O-6-（CO2CH3）-嘧啶-2-基 CH3H
291 吡咯-2-基 CH3H
292 CH3吡咯-2-基 H
293 5-CF3-吡啶-3-基 CH3H
294 3-（嘧啶氧基）-C6H4CH3H
295 3-炔丙基氧基-C6H4CH3H
296 CH3H H
297 5-（2，4-二氟苯基）-呋喃-2-基 CH3H
298 CH35-（2，4-二氟苯基）-呋喃 H
-2-基
299 C2H5O CH3H
300 4-叔-丁基-C6H4CH3H
301 4-炔丙基-嘧啶-2-基 CH3H
302 2-C2H5O-C6H4CH3H
303 4-C2H5-C6H4CH3H
304 3-C2H5O-C6H4CH3H
305 CH3S CH3H
306 CH3SO2CH3H
307  φ  φ  H
308 4-正-C3H7O-嘧啶-2-基 CH3H
309 3-正-己氧基-C3H6CH3H
310 4-正-丁氧基-嘧啶-2-基 CH3H
311 苯并噻吩-3-基 CH3H
312 3-[（CH3）2C＝CHCH2O]-C6H4CH3H
313 2，4-di-CH3O-嘧啶-6-基 CH3H
314 3-CF3-C6H41，2，4-三唑-1-基 H
315 3-CH3S-吡嗪-2-基 CH3H
316 3-N（CH3）2-C6H4CH3H
317 3-CF3-C6H4Cl H
318  φ  φ  H
319 苯并呋喃-2-基 CH3H
表Ⅰ（续）
化合物号
R1R2A
320 2-CH3S（O）-嘧啶-4-基 CH3H
321 3-NH2C（S）-C6H4CH3H
322 4-NH2C（S）-吡啶-2-基 CH3H
323 3-（CH3OCH2CH2OCH2O）-C6H4CH3H
324 3-（氰基甲氧基）-C6H4CH3H
325  φ  φ  H
326 3-（F2HCO）-C6H4CH3H
327 6-C2H5O-吡嗪-2-基 CH3H
328 4-CH3-6-OCH3-嘧啶-2-基 CH3H
329 4-CH3-噻吩-2-基 CH3H
330 2，4-di-CH3-噻唑-5-基 CH3H
331 4-CF3-6-CH3-嘧啶-2-基 CH3H
332 5-Br-吡啶-3-基 CH3H
333 5-CONHCH3-吡嗪-2-基 CH3H
334 4，6-di-OC2H5-嘧啶-2-基 CH3H
+335 5-CH3-呋喃-2-基 CH3H
+335A 5-CH3-呋喃-2-基 CH3H
336 2-SCH3-嘧啶-4-基 CH3H
337 4-异-C3H7O-嘧啶-2-基 CH3H
338 N-CH3-3-CH3-5-OC6H5-吡唑-4-基 H H
339 3-CH3-苯并噻吩-2-基 CH3H
340 4-OCH2CF3-嘧啶-2-基 CH3H
341 2-N（CH3）2-嘧啶-4-基 CH3H
342 5-NO2-吡啶-2-基 CH3H
343 2-叔t-C4H9-嘧啶-5-基 CH3H
344 5-NO2-1苯并呋喃-2-基 CH3H
345 4-O（CH2）2OCH3-吡啶-2-基 CH3H
346 3，4-二-Cl-C6H3CH3H
347 6-OC2H5-吡啶-2-基 CH3H
348 4-CF3-6-OCH2CF3-吡啶-2-基 CH3H
349 4-CF3-6-OC2H5-吡啶-2-基 CH3H
350 5-CF3-吡啶-2-基 CH3H
符号解释：
＊该化合物的制备方法见实施例1。
+化合物335是一种异构体，化合物335A是两种异构体的2∶1混合物。
φ如下面的“化学结构式”所示，基团R1和R2连接一起构成环。
表Ⅱ包括式（Ⅰ.2）的350种化合物。每一种化合物的R1、R2和A的定义与表1中相同序号化合物给出的定义相同。表Ⅰ和表Ⅱ化合物之间的差别仅仅是表1化合物的乙酰胺基上有一个N-甲基取代基，而表Ⅱ化合物的乙酰胺基上有二个N-甲基取代基。
表Ⅲ包括式（L3）的350种化合物。每一个化合物的R1、R2和A的定义与表Ⅰ中相同序号化合物给出的定义相同。表Ⅰ和表Ⅲ化合物的差别仅仅是表1化合物的乙酰胺上有一个N-甲基取代基，而表Ⅲ的化合物的乙酰胺基上无N-取代基。
表Ⅳ
表Ⅳ列出了表1中所述的某些化合物和表Ⅲ中第346号化合物在270MHz下测得的熔点和选择的质子核磁共振数据。除非另作说明，用四甲基硅烷和氘氯仿作溶剂。在20℃下测定化学位移（ppm）。
采用下列缩写：
s＝单峰  m＝多重峰  d＝双重峰
dd＝双重双重峰  t＝三重峰  br＝宽峰
ppm＝百万分之一
化合物号  熔点（℃）  质子核磁共振数据（δ）
（表1，只是如同
所示那样）
40  胶  2.30（3H，s），2.88（3H，d），3.94（3H，s），
5.14（2H，s），6.72（1H，br），7.16-7.25
（2H，m），7.32-7.43（2H，m），7.48-7.51
（1H，m），7.60-7.68（1H，m），7.81
-7.85（1H，d），8.58-8.60（1H，d）ppm
化合物号  熔点（℃）  质子核磁共振数据（δ）
（表1，只是如同
所示那样）
47  77-79
63  92-94
75  胶质化  2.28（3H，s），2.9（3H，d），3.95（3H，
s），5.18（2H，s），6.8（1H，br），
7.18-7.21（1H，m），7.31-7.51（4H，
m），8.12（1H，s），8.70（1H，d）ppm.
103  70-71
109  53-55
113  62-64
115  胶质化  2.18（3H，s），2.88（3H，d），3，95（3H，s），
5.12（2H，s），6.73（1H，br），6.99-7.
07（1H，m），7.17-7.22（1H，m），7.28
-7.52（6H，m）ppm.
127  胶质化  2.22（3H，s），2.88（3H，d），3.94（3H，S），
5.14（2H，s），6.74（1H，brm），7.1-7.9
（8H，m）ppm
158  76-78
176  胶质化  2.2（3H，s），2.5（6H，s），2.95（3H，d）
3.95（3H，s），5.1（2H，s），6.75（1H），
7.1-7.5（4H，m），8.25（1H，s）ppm
188  105-107
194  71-73
198  88-90
236  99-100
260  120.8-122
264  138-140
269  121-122.5
295  103-105
326  41-43
328  89-91
329  73-75
330  122-124
331  161-163
332  112-113
333  140-142
334  93-95
335  108-109
335A  胶质化  2∶1异构体的混合物，主要组分
2.18（3H，s），2.32（3H，s），2.8（3H，d），
3.92（3H，s），5.06（2H，s），6.07（1H，d）
6.64（1H，br），7.03（1H，m），7.17-7.23（1H，
m），7.33-7.45（2H，m），7，47-7.53（1H，m）
ppm
次要组分
2.08（s），2.34（s），2.9（d），3.94（s），5.11
（s），6.02（d），6.49（d），6.72（br），7.17-7.
23（m），7.33-7.45（m），7.47-7.52（m）ppm
336  122-124
337  97-98.5
338  108-110
339  136-137
340  125-126
341  113-116
342  120-124
343  87-89
344  62-64
345  胶质  2.29（3H，s），2.89（3H，d），3.46（3H，S），
3.77（2H，t），3.96（3H，s），4.19（2H，t），5.
16（2H，s）6.76（1H，m），6.81（1H，dd），7.2-
7.5（5H，m），8.39（1H，d）ppm
346＊  114-116
347  87.4-88.4
348  143.5-143.9
349  111.6-112.8
350  118.4-118.8
本发明的化合物可用EP-A-0370629和EP-A-0398692所述的方法制备。前一篇参考文献说明怎样制备含有连接在式Ⅰ中苯环上的β-甲氧基丙烯酸甲酯基而不是O-甲基氧代亚氨基乙酰胺基的相似化合物。后一篇参考文献说明怎样构成氧代亚氨基乙酰胺基。
本发明还包括用式（Ⅱ）化合物与胺NHR5R6（其中A，R1、R2、R5和R6具有上文给定的定义，R是H或C1-4烷基）反应制备权利要求Ⅰ化合物的方法。
2-（溴甲基）苯酰甲酸甲酯O-甲基肟（后面在“化学结构式”）下面的图解Ⅰ中的化合物A）提供合适的原料。如同EP-0363818所述该原料可通过将2-甲基苯酰甲酸甲酯O-甲基肟溴化制备。用于制备式（Ⅰ）化合物的优选（E）-异构体的后一个化合物的（E）-异构体例如可以在实施例2所述的酸化条件下通过将（Z）-异构体或（Z）-和（E）-异构体混合物异构化制得。另一方面，该异构化步骤可作为制备式（Ⅰ）化合物的最后一步来进行。
该化合是有效的杀菌真剂，可用来防治下列一种或多种病原菌：稻瘟病（Pyricularia  oryzae）;小麦叶锈病（Puccinia  recondita）、条锈病（Puccinia  striiformis）和其他锈病;大麦杆锈病（Puccinia  hordei）、条锈病（puccinia  striiformis）和其他锈病，和其他寄主，例如咖啡、梨、苹果、花生、蔬菜和装饰植物的锈病;大麦和小麦的白粉病（Erysiphe  graminis），及各种寄主的其他白粉病，如啤酒花白粉病（sphaerotheca  macularis）黄瓜白粉病（sphaerothecafuliginea）、苹果白粉病（Podosphaera  leucotricha）和葡萄白粉病（Uncinula  necator）;谷类的黑麦草网斑病（helminthosporiumspp.）、刺子莞属病（Rhynchosporium  spp.）、壳针孢属病（septoriaspp.）、核球壳菌属病（pyrenophora  spp.）、pseudocercosporella  herpotrichoides和Gaeumannomyces  graminis;花生的Cercospora  arachidicola和Cercosporidium  personata，和其他寄主，如甜菜、香蕉、大豆和稻谷的其他尾孢菌属病（Cercospora）：蕃茄、草莓、蔬菜、葡萄和其他寄主的灰霉病（Botrytic  cinerea）;蔬菜（如黄瓜）、油菜籽、平果、蕃茄和其他寄主的铰链孢属病（Alternaria  spp）;苹果黑星病（Venturia  inaequalis）;葡萄霜霉病（Plasmopara  vi-ticola）;其他霜霉病，例如莴苣的Bremia  lactucae，大豆、烟草、洋葱和其他寄主的霜霉病（peronospora  spp.），啤酒花的Pseudo-peronospora  humuli和黄瓜霜霉病（Pseudoperonosporacubensis）;马玲薯和蕃茄晚瘟病（Phytophthora  infestans）和蔬菜、草莓、颚梨、胡椒、装饰植物、烟草、可可和其他寄主的其他疫霉病（Phytophthora  spp.）;稻谷的Thanatephorus、cucumeris病和各种寄主，例如小麦、大麦、蔬菜、棉花和草皮的其他Rhizoc-tonia病。
一些化合物对体外真菌显示宽范围的活性。它们对收获后的水果病害〔例如柑桔录霉病和青霉病（Penicillium  digitatum  and  italicum，和Trichoderma  viride），香蕉的Gloeosporium  musarum和葡萄灰霉病（Botrytis  cinerea）〕也具有活性。
另外，一些化合物在拌种时对下列病原菌可具有活性：谷类的立枯病（Fusarium  spp.）、壳针孢属病（Septoria  spp.）、黑穗病（Tilletia  spp.）、（腥黑穗病，小麦种子上的病害）、黑穗病（Ustilago  spp.）和黑麦草网斑病（Helminthosporium  spp.），棉花的Rhizoctonia  solani和稻疫病（Pyricularia  oryzae）。
这些化合物可以在植物组织内向前和局部地活动。而且这些化合物可以在气相中充分挥发，对植物上的真菌具有较强的活性。
因此，本发明提供的抗真菌的方法包括将杀真菌有效量的上述化合物或含该化合物的组合物用于植物、植物种子或植物或种子存在的场所。
这些化合物可直接用于农业目的，但为更方便起见可用载体或稀释剂将其配制成组合物。因此，本发明提供的杀真菌组合物包括上文定义的化合物和可接受的载体或稀释剂。
这些化合物可用若干种方法使用。例如可将它们配制或不配制成制剂，直接用于植物叶子、种子或植物生长或种植的其他介质，或可将它们喷雾、喷粉或可以膏剂或糊剂使用，或可以蒸汽或缓慢释放的颗粒剂使用。
可将这些化合物用于包括叶子、茎枝或根的植物任何部分，或根周围的土壤中、或在种植前的种子上。通常用于土壤、稻田水或水载系统中。本发明化合物也可采用电动喷射技术或其他少量喷雾方法将其喷射在植物上或喷雾在蔬菜上。
这里所用的术语“植物”包括籽苗、灌木和乔木。此外本发明的杀真菌方法包括预防、保护和根除处理。
该化合物最好以组合物的形式用于农业或园艺目的，在任何情况下，所采用的组合物类型取决于面对的具体目的。
该组合物可以是含下列组分的可喷粉的粉剂或颗粒剂活性组分（本发明化合物）和固体稀释剂或载体，例如添加剂，如高岭土、膨润土、硅藻土、白云石、碳酸钙、滑石粉、粉状氧化镁、漂白土、石膏、硅藻土和陶土。上述细粒剂可预制成适于向土壤使用的颗粒而不需进一步处理。这些颗粒剂或者可通过用活性组分浸渍添加剂颗粒或将活性组分与粉状添加剂一起压制成颗粒制备。适于拌种的组合物含有助于将组合物粘附到种子上的试剂（例如矿物油）;此外，可用有机溶剂（例如N-甲基吡咯烷酮、丙二醇或N，N-二甲基甲酰胺）配制活性组分，以适用于拌种。也可将该组合物配制成含湿润剂或易于在液体中分散的分散剂的可湿性粉剂或可分散于水中的颗粒剂。粉剂或颗粒剂也可含添加剂和悬浮剂。
乳油或乳剂的制备可通过将活性组分溶于含任选的湿润剂或乳化剂的有机溶剂中，然后将混合物加到可含湿润剂或乳化剂的水中。适合的有机溶剂是芳族溶剂，如烷基苯、烷基萘、酮，如环己酮和甲基环己酮，氯化烃如氯苯、三氯乙烷，和醇，如苄醇、糠醇、丁醇和乙二醇醚。
配制含大量不溶性固体的悬浮液浓缩物是通过将分散剂与可阻止固体沉降的悬浮剂一起研磨成球或珠状物来制备。
用于喷撒的组合物可配制成气雾剂，将该制剂装入处于挥发剂（例如氟三氯甲烷或二氯二氟甲烷）压力下的容器内。
本发明化合物可在干的状态下与烟火混合物混合，配制成适于在密闭空间产生含该化合物烟雾的组合物。
此外可将该化合物配制成微胶囊包封剂形式使用。也可配制成可控制活性物质缓慢释放的生物降解聚合物制剂。
通过含合适添加剂，例如可改善分布、粘附粉末和处理表面防雨的添加剂的不同组合物可更好地适合于各种用途。
本发明化合物可与肥料（例如含氮、钾或磷的肥料）混合使用。优选仅含有用本发明化合物涂覆的颗粒肥料。上述颗粒适合含25%（重量）该化合物。因此，本发明提供含肥料和通式（Ⅰ）化合物或其盐或金属络合物的肥料组合物。
可湿粉剂、乳油和悬浮液浓缩物通常含表面活性剂，例如湿润剂、分散剂、乳化剂或悬浮剂。这些试剂可以是阳离子、阴离子或非离子试剂。
适合的阳离子试剂是季铵化合物，例如溴化十六烷基三甲基铵。合适的阴离子试剂是皂、硫酸的脂族单脂盐（例如十二烷基硫酸钠）和磺化的芳族化合物的盐类（例如十二烷基苯磺酸钠、木素磺化钠、钙或铵、丁基萘磺酸盐及二异丙基和三异丙基萘磺酸钠的混合物）。
适合的非离子试剂是环氧乙烷与脂肪族醇例如油醇或十六烷醇或与烷基酚例如辛基或壬基酚和辛基甲酚的缩合产物。其他非离子试剂是由长链脂肪酸和己糖醇酐衍生的偏酯，所述偏酯与环氧乙烷的缩合产物和卵磷酯。适合的悬浮剂是亲水胶体（例如聚乙烯吡咯烷酮和羧甲基纤维素钠）和润胀粘土，例如膨润土或硅镁土。
用作含水分散剂或乳剂的组合物通常是含大量活性组分的浓缩物。该浓缩物在使用前用水稀释。这些浓缩物最好可长期贮存。经长期贮后浓缩物可用水稀释以便形成含水制剂，其能在足够长的时间保持均匀以便适用于普通喷雾设备。该浓缩物一般可含高达95%（重量），适合的为10-85%（重量），例如25-60%（重量）的活性组分。浓缩物稀释后形成含水的制剂，这样的含水制剂根据要求的目的可含不同量的活性组分，但可以使用含0.0005%或0.01%-10%（重量）活性组分的含水制剂。
本发明组合物可含具有生物活性的其他化合物，例如具有相似或辅助杀真菌活性或具有调节植物生长、除草或杀虫活性的化合物。
本发明组合物中的杀真菌化合物可以是能抗谷类（如小麦）穗病害的化合物。穗病害有例如壳针孢属病septoria  spp.、赤霉病（Giberella  spp.）和黑麦草网斑病（Helminthosporium  spp.），种子和土壤中的病害，葡萄的霜霉病和白粉病和苹果的白粉病和黑星病。该组合物通过含其他杀真菌剂，比只含通式（Ⅰ）化合物的组合物具有广谱活性。此外，其他杀真菌剂可对通式（Ⅰ）化合物的杀真菌活性具有增效作用。可包括在本发明组合物中的杀真菌化合物的例子是（RS）-1-氨基丙基膦酸、（RS）-4-（4-氯苯基）-2-苯基-2-（1H-1，2，4-三唑-1-基甲基）丁腈、（Z）-N-丁-2-烯氧基甲基-2-氯-2′，6′-二乙基N-乙酰苯胺、1-（2-氰基-2-甲氧基亚氨基乙酰基）-3-乙基脲、3-（2，4-二氯苯基）-2-（1H-1，2，4-三唑-1-基）喹唑啉-4（3H）-酮、4-溴-2-氰基-N，N-二甲基-6-三氟甲基苯并咪唑-1-氨磺酰、5-乙基-5，8-二氢-8-氧代（1，3）-二氧杂戊环并（4，5-g）喹啉-7-羧酸、α-[N-（3-氯-2，6-二甲苯基）-2-甲氧基-乙酰氨基]-γ-丁内酯、aldimorph、敌菌灵、benalaxyl、苯菌灵、biloxazol、乐杀螨、bitertanol、灭瘟素S、bromuconazole、磺嘧菌灵、粉病定、敌菌丹、克菌丹、多菌灵、萎锈灵、chlorbenzthiazone、地茂散、百菌清、Chrorozolinate、含铜化合物，例如氧氯化铜、硫酸铜和碱式硫酸铜的混合物、放线菌铜、cymoxanil、cyproconazole、cyprofuram、二-2-吡啶基二硫化物1，1′-二氧化物、抑菌灵、二氯萘醌、diclobutrazol、diclomezine、氯硝胺、difenoconazole、dimethamorph、甲菌定、diniconazole、敌螨普、杀菌磷、二噻农、吗菌灵、多果定、克瘟散、etaconazole、乙菌定、（Z）-N-苄基-N-（[甲基（甲硫基亚乙基  氨基-氧代羰基）氨基]硫代）-β-氨基丙酸乙酯、氯唑灵、菌拿灵、异嘧菌醇、呋菌胺、fenpiclonil、fenpropidin、fenpropimorph、薯瘟锡、毒菌锡、flutolanil、flutriafol、flusilazole、灭菌丹、fosetyl-aluminium、麦穗定、呋氨丙灵、furconazole-cis、双胍盐、Hexaconazole、土菌消、烯菌灵、imibenconazole、iprobenfos、异丙啶、富士一号、春雷霉素、代森锰锌、代森锰、mepanipyrim、mepronil、氨丙灵、甲呋菌胺、metsulfovax、myclobutanil、甲胂铁铵、二甲基二硫代氨基甲酸镍、异丙消、环菌灵、ofurace、有机汞化合物，oxadixyl、氧化萎锈灵、Pefurazoate、penconazole、pencycuron、叶枯净、酞酰亚胺、多氧菌素D、代森联、噻菌灵、丙氯灵、杀菌利、百维灵、Propiconazole、甲基代森锌、胺丙威、定菌磷、pyrifenox、Pyroquilon、Pyroxyfur、硝吡咯菌素、灭螨锰、五氯硝基苯、SSF-109、链霉素、硫、tebuconazole、白叶减、四氯硝基苯、tetraconazole、涕必灵、thicyofen、甲基托布津、福美双、tolclofos-methyl、1，1′亚氨基二（1，8-亚辛基）双奎尼定四乙酸盐、唑菌酮、唑菌醇、丁基三唑、三环唑、克啉菌、嗪氨灵、有效霉素A、烯菌酮、Zarilamid和代森锌。通式（Ⅰ）的化合物可与土壤、泥煤或其他根部介质混合用于保护植物抗种子、土壤或叶子的真菌病害。
可混合在本发明组合物中的合适杀虫剂包括buprofezin、亚维因、虫螨威、carbsulfan、毒死蜱、cycloprothrin、甲基-0五九、二嗪农乐果、ethofenprox、杀螟松、fenobucarb、信硫磷、安果、异丙威、异噁唑磷、久效磷、稻丰散、抗蚜威、丙虫磷和XMC。
调节植物生长的化合物是防治杂草或种子头状叶丛、植物群系或选择性地防治较少要求的植物（例如草）生长的化合物。
用于本发明的调节植物生长的化合物的例子是3，6-二氯吡啶甲酸、1-（4-氯苯基）-4，6-二甲基-2-氧代-1，2-二氢吡啶-3-羧酸、3，6-二氯茴香酸甲酯、脱落酸、黄草灵、新燕灵、草长灭、丁酰肼、苯敌死、敌草克、乙烯利、fenpentezol、氟通安、草甘膦、草甘双膦、4-羟基苄腈（如溴苯腈）、inabenfide、isopyrimol，长链脂肪醇和酸、马来酰肼、氟苯磺、抑草丁（如氯甲丹）、Paclobutrazol、苯氧乙酸（如2，4-D或MCPA）、取代的苯甲酸（如三碘苯甲酸）、取代的季铵和鏻化合物（如矮壮素阳离子、氯化膦或比克）、四氯硝基苯、植物生长激素（如吲哚乙酸、吲哚丁酸、萘乙酸或萘氧基乙酸）、细胞分裂素（如苯并咪唑、苄腺嘌呤、苄氨基嘌呤、二苯基脲和激动素）、赤霉素（如GA3、GA4或GA7）和triapenthenol。
以下列实施例说明本发明。除了另作说明外，在所有实施例中术语“醚”意指乙醚、硫酸镁用于干燥溶液，溶液在减压下浓缩。涉及空气或水敏感中间体的反应是在氮气氛下进行的，并且溶剂在使用前最好干燥。除了另作说明外，用硅胶柱作固定相进行色谱分离。如所述，核磁共振数据是选择的，不需列出所有情况下的吸收值。除了另作说明，1HNMR谱是用CDCl3溶液记录的。所有实施例采用下列缩写：
DMF＝N，N-二甲基甲酰胺  d＝双重峰
NMR＝核磁共振  m＝多重峰
S＝单峰  br＝宽峰
实施例1
本实施例说明表1中第127号化合物的制备方法（参见图解1）。
将在DMF（20毫升）中的3-三氟甲基苯乙酰肟（1.59克）逐滴加到搅拌的氢氧化钠（0.187克）在DMF（10毫升）中的悬浮液中。一小时后，将反应混合物冷却到0℃，在搅拌下逐滴加入（E）2-（溴甲基）苯酰甲酸甲酯0-甲基肟[（A），2.36克，用EP-A-0363818所述防法制备]在DMF（20毫升）中的溶液。再过三小时后，将反应混合物倾注入水中，并用乙酸乙酯（X3）萃取。有机萃取液用盐水洗涤、干燥，浓缩，并用乙酸乙酯∶己烷（1∶4）作洗脱液进行色谱分离得到无色胶状的双肟醚（B）（2.83克，产率88%）。1HNMR（270MHz）：δ2.21（3H.s），3.82（3H.s），4.03（3H.s），5.15（2H，s）7.1-7.9（8H，m）ppm。
将双肟醚（B）（2.3克）在甲醇中的溶液逐滴加到甲胺在甲醇（200毫升）中的冷却和饱和溶液中。放置2天后，反应混合物浓缩、用醚∶己烷（3∶2）作洗脱液，进行色谱分离残余的黄色胶状物，得到标题化合物（1.46克，产率64%）。1HNMR（270MHz）;δ2.22（3H，S），2.88（3H，d），3.94（3H，S），5.14（2H，S），6.74（1H，brm），7.1-7.9（8H，m）ppm。
实施例2
本实施例说明将（Z）2-甲基苯酰甲酸甲酯0-甲基肟异构化成相应的（E）异构体，用来制备实施例1的2-（溴甲基）苯基乙醛酸甲酯O-甲基肟（A）。
将（Z）2-甲基苯酰甲酸甲酯O-甲基肟（102毫克）溶于二噁烷（5毫升）中，加入浓盐酸（0.25毫升）。将反应物加热回流24小时，并冷却之。该反应物 在醚和碳酸氢钠饱和水溶液之间分配。含水层用乙醚萃取二次以上，将合并的有机层干燥（硫酸钠）并浓缩。用快速色谱法（用25%乙醚的己烷溶液洗脱）提存剩余物，得到标题化合物（42毫克，产率41%）：1HNMR（270MHz）：δ2.2（3H，S），3.85（3H，S），4.05（3H，S），7.1（1H，m），7.2-7.4（3H，m）ppm。
下列实施例是适用于农业和园艺目的的用本发明化合物配制的组合物实施例。上述组合物构成本发明另一方面。
实施例3
通过将下列组分混合并搅拌直至全部溶解配制乳油。
表1中的第260号化合物  10%
苄醇  30%
十二烷基苯磺酸钙  5%
壬基酚乙氧基化物（13摩尔环氧乙烷）  10%
烷基苯  45%
实施例4
将活性组分溶于二氯甲烷，并将得到的溶液喷撒在粒状硅镁土上。然后让溶剂蒸发，产生粒状组合物。
表1中第264号化合物  5%
硅镁土颗粒  95%
实施例5
用作拌种的组合物是通过将下列三种组分研磨并混合制得的。
表1中第269号化合物  50%
矿物油  2%
陶土  48%
实施例6
可喷粉的粉剂是通过将下列活性组分与滑石一起研磨和混合制得的。
表1中第295号化合物  5%
滑石  95%
实施例7
通过将下列组分与水一起球磨，形成粉末混合物的含水悬浮液配制悬浮液浓缩物。
表1中第330号化合物  40%
木素磺酸钠  10%
膨润土  1%
水  49%
该制剂用水稀释后用于喷雾或直接用于种子上。
实施例8
通过将下列组分混合并碾磨，直至所有组分充分混合配制可湿性粉剂
表1中第331号化合物  25%
十二烷基硫酸钠  20%
木素磺酸钠  5%
二氧化硅  25%
陶土  43%
实施例9
试验该化合物抗各种植物叶真菌病害的情况。所用方法如下。
让植物生长在盛有John  Innes盆载混合肥料（1号或2号）直径为4厘米的小盆中。试验化合物或者通过与含水DispersolT一起球磨配制，或者将其配制成溶于丙酮或丙酮/乙醇的溶液，该溶液在使用前应直接稀释到要求的浓度。将该制剂（100ppm活性组分）喷撒在叶子上或用在土壤中的植物根部，喷撒制剂应达到最大保留值，根部浸透干土壤中的最终浓度约为100ppm。当喷撒谷物时应加入吐温20、最终浓度应达0.05%。
大部分试验是在植物接种病害前1天至2天将化合物撒在土壤（根部）或撒在叶上（通过喷雾）。但在试验Puccinia  Recondita和Erysiphe  gramins时例外，该试验是在处理植物前48小时和24小时分别接种病害。将叶病原菌配制成游动孢子囊悬浮液喷撒在试验植物叶子上。接种后将植物放在适当的环境中让其进行感染，接着培养直至准备好病害以便作出评价。根据病害和环境状况从接种至可作出评价所需的时间为4天至14天。
每种处理植物存在的病害程度（即被活性产  孢病害复盖的叶子面积）可用下列评价标度表示：
0＝0%  病害程度  20＝10.1-20%  病害程度
1＝0.1-1%  病害程度  30＝20.1-30%  病害程度
3＝1.1-3%  病害程度  60＝30.1-60%  病害程度
5＝3.1-5%  病害程度  90＝60.1-100%  病害程度
10＝5.1-10%病害程度
然后每个评价值用存在的病害程度对未处理对照植物病害程度的百分数表示：这个计算值叫做POCO（对照物百分数）值，下面是典型的计算方法的实例。
未处理的对照植物病害程度＝90
处理植物病害程度＝30
POCO＝ (处理植物病害程度)/(未处理对照植物病害程度) ×100%
＝ 30/90 ×100＝33.3
接着将计算的POCO值四舍五入取上述9个评价标度中最接近的值。在上述具体实例中，POCO应四舍五入取30，如果计算的POCO值恰好落在二个标度之间，则该计算值应四舍五入取这二个值中较低值。
下面表Ⅴ所示的结果表示四舍五入后的POCO值。
表Ⅴ
表1中的化合物号  Pr  Egt  Sn  Po  Tc  Vi  Pv  Pil
63  0  0  0  10  -  0  0  80
75 0a0a5a90a- 0a0a90a
103 5a30a1a20a- 0a0a90a
109 1a0a0a0a- 0a0a90a
115  0  0  0  0  -  0  0  0
127 0＊0 0 0 0 0 0 0
176  0  0  0  1  -  0  0  0
236  0  0  0  0  0  0  0  10
260 0＊0 0 0 0 0 0 3
269 0＊0 0 0 5 0 0 5
326  0  0  0  0  -  0  0  0
328  0  0  0  0  0  0  0  90
329 5a30a3a20a- 0a0a
331 5a0a30a90a- 20a10a90a
332 5a0a5a30a- 0a0a90a
333  0  0  0  20  -  0  0  90
334 10a30a20a30a- 60a10a90a
335 5a0a30a90a- 5a5a90a
335A  0  0  0  0  -  0  0  10
336  0  0  0  30  -  0  0  90
337  0  0  0  0  0  0  0  10
a＝叶仅撒药10ppm
★＝叶防护剂试验（例如在植物处理前移植细菌）
-＝无结果
病害的符号解释
Pr叶锈病（Puccinia  recodita）
Egt白粉病（Erysiphe  graminis  tritici）
Sn颖枯病（Septoria  nodorum）
Po稻瘟病（Pyricularia  oryzae）
Tc  Thanetophorus  cucumeris
Vi黑星病（Venturia  inaequalis）
Pv霜霉病（Plasmopara  Viticola）
Pil晚疫病（Phytophthora  infestans  lycopersici）
                     说明书中的化学结构式
Figure 921011849_IMG5
                化合物53：
Figure 921011849_IMG6
          化合物153：
Figure 921011849_IMG7
Figure 921011849_IMG8
                                        表Ⅰ中的化合物127

Claims (10)

1、具有式(I)
Figure 921011849_IMG2
及其立体异构体的化合物，其中A是氢、卤素、羟基、C1-4烷基、C1-4烷氧基、C1-4卤代烷基、C1-4卤代烷氧基、C1-4烷基羰基、C1-4烷氧基羰基、苯氧基、硝基或氰基；R1和R2可以相同或不同，是氢、任意取代的烷基、任意取代的环烷基、任意取代的杂环基烷基、任意取代的烷基烷基、任意取代的芳烷基、任意取代的芳氧基烷基、任意取代的杂环氧基烷基、任意取代的链烯基、任意取代的炔基、任意取代的烷氧基、任意取代的芳基、任意取代的杂环基、任意取代的芳氧基、任意取代的杂环基氧基、硝基、卤素、氰基、-NR3R4、-CO2R3、-CONR3R4、-COR3、-S(O)nR3(其中n是0、1或2)、(CH2)mPO(OR3)z(其中m是0或1)，或R1和R2连接在一起形成碳环或杂环体系；R3和R4相同或不同，是氢、任意取代的烷基、任意取代的芳烷基、任意取代的链烯基、任意取代的炔基、任意取代的芳基或任意取代的杂芳基，或R3和R4连接在一起形成任意取代的杂环；并且R5和R6分别是氢和C1-4烷基。
2、根据权利要求1的化合物，其中烷基和烷氧基部分用卤素、氰基、羟基、C1-4烷氧基或C1-4烷氧基（C1-4）烷氧基任意取代;环烷基部分用卤素、羟基或C1-4烷氧基任意取代;链烯基部分用任意取代的芳基或杂芳基任意取代;炔基部分用任意取代的芳基任意取代;芳基和杂环基部分用一个或多个下列取代基任意取代：卤素、羟基、巯基、C1-4烷基、C2-4链烯基、C2-4炔基、C1-4烷氧基、C2-4链烯氧基、C2-4炔氧基、卤代（C1-4）烷基、卤代（C1-4）烷氧基、C1-4烷硫基、羟基（C1-4）烷基、C1-4烷氧基（C1-4）烷基、C1-4烷氧基（C1-4）烷氧基、C3-6环烷基、C3-6环烷基（C1-4）烷基、任意取代的芳基、任意取代的杂芳基、任意取代的芳氧基、任意取代的杂芳氧基、任意取代的芳基（C1-4）烷基，其中烷基部分用羟基任意取代，任意取代的杂芳基（C1-4）烷基，任意取代的芳基（C2-4）链烯基、任意取代的杂芳基（C2-4）链烯基、任意取代的芳基（C1-4）烷氧基、任意取代的杂芳基（C1-4）烷氧基、任意取代的芳氧基（C1-4）烷基、任意取代的杂芳基氧基（C1-4）烷基、酸基、氰基、异氰基、氰硫基、异氰硫基、硝基，-NR′R″、-NHCOR′、-NHCONR′R″、-CONR′R″、-COOR′、-OSO2R′、SO2R′-COR′、-CR′＝NR″或-N＝CR′R″，其中R′和R″分别是氢、C1-4烷基、C1-4烷氧基、C1-4烷硫基、C3-6环烷基、C3-6环烷基（C1-4）烷基、苯基或苄基，这些苯基和苄基用卤素、C1-4烷基或C1-4烷氧基任意取代;任何上述其他取代基的芳环或杂芳环用下列一个或多个取代基任意取代：卤素、羟基、巯基、C1-4烷基、C2-4链烯基、C2-4炔基、C1-4烷氧基、C2-4链烯氧基、C2-4炔氧基、卤代（C1-4）烷基、卤代（C1-4）烷氧基、C1-4烷硫基、羟基（C1-4）烷基、C1-4烷氧基（C1-4）烷基、C3-6环烷基、C3-6环烷基（C1-4）烷基、烷酰氧基、苯甲酰基氧基、氰基、异氰基、氰硫基、异氰硫基、硝基、-NR′R″、-NHCOR′、-NHCONR′R″、-CONR′R″、-COOR′、-SO2R′、-OSO2R′、-COR′、-CR′＝NR″或-N＝CR′R″，其中R′和R″具有上述给定的定义。
3、根据权利要求1或2的化合物，其中杂环基部分选自噻吩基、呋喃基、吡咯基、异噁唑基、噁唑基、吡唑基、咪唑基、三唑基、噻唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、苯并呋喃基、苯并噻吩基、二苯并呋喃基、苯并噻唑基、苯并噁唑基、吲哚基、喹啉基和喹喔啉基，及其合适的N-氧化物。
4、根据上述任何一个权利要求的化合物，其中R3和R4连接在一起形成的杂环选自吡咯烷、哌啶、吗啉、硫代吗啉、哌嗪、六亚甲基亚胺、四氢喹啉、四氢异喹啉和2，3-二氢-1，4-苯并噁嗪，其用卤素、氰基、硝基、C1-6烷基、C1-6烷氧基或C1-6烷硫基任意取代。
5、根据权利要求1的化合物，其中A是氢、卤素、羟基、甲基、甲氧基、三氟甲基、三氟甲氧基、C1-2烷基羰基、C1-2烷氧基羰基、苯氧基、硝基或氰基;R1是C1-4烷基、卤代（C1-4）烷基、C1-4烷氧基、卤代（C1-4）烷氧基、C1-4烷基羰基、C1-4烷氧基羰基、氰基、苯基（C1-4）烷基、苯基、含1或多个O，N或S原子和任意稠合到苯环上的5或6员芳族杂环，上述任何一个芳族或杂芳族部分用下列一个或多个取代基任意取代：卤素、羟基、C1-4烷基、卤代（C1-4）烷基、C1-4烷氧基、卤代（C1-4）烷氧基、C1-4烷基羰基、C1-4烷氧基羰基、硝基、氰基、苯基、苯氧基、苄基或苄氧基;R2是氢、卤素、C1-4烷基、卤代（C1-4）烷基、C1-4烷基羰基、C1-4烷氧基羰基、氰基或苯基;或R1和R4连接在一起形成C5-10碳环体系。
6、根据权利要求1的化合物，其中A是氢或卤素;R1是C1-4烷基、苄基、C1-4烷基羰基、C1-4烷氧基羰基、氰基、苯基、噻吩基、三唑基、噻唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、喹啉基或喹喔啉基，上述任何一个芳族或杂芳族部分用一个或多个卤素、C1-4烷基、三氟甲基、C1-4烷氧基、三氟甲氧基、硝基、氰基、苯基或苄氧基任意取代;R2是氢、C1-4烷基、C1-4烷基羰基、C1-4烷氧基羰基、氰基或苯基;或1和R2连接在一起形成任意稠合到苯环上的环戊基或环己基;R5和R6分别是氢或C1-4烷基。
7、根据权利要求1的化合物，其中A是苯基、噻吩基、呋喃基、吡咯基、咪唑基、三唑基、噻唑基、噁唑基、异噁唑基、吡唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、喹啉基、喹喔啉基、苯并噻唑基、苯并噁唑基、苯并噻吩基或苯并呋喃基，上述任何一个芳族或杂芳族部分用下列一个或多个取代基任意取代：卤素、C1-6烷基、卤代（C1-4）烷基、C1-6烷氧基、氰基（C1-4）烷氧基、卤代（C1-4）烷氧基、C1-4烷氧基（C1-4）烷基、C1-4烷氧基（C1-4）烷氧基、C1-4烷氧基（C1-4）烷氧基（C1-4）烷氧基、C1-6烷硫基、C2-6链烯基、C2-6链烯基氧基、C2-6炔基、C2-6炔氧基、硝基、氰基、苯基、苯氧基、苄氧基、CO2R′、CONR′R″、CSNR′R″、NR′R″、S（O）nR′、NHCONR′R″，其中R′和R″分别是H或C1-4烷基、n是0，1或2;R2是甲基;R5是氢，R6是甲基;或其合适的N-氧化合物。
8、制备权利要求1化合物的方法，包括将式（Ⅱ）的化合物
Figure 921011849_IMG3
其中A、R1和R2具有权利要求1中给定的定义，并R是H或C1-4烷基，与胺NHR5R6反应，其中R5和R6具有权利要求1中给定的定义。
9、杀真菌组合物，包括权利要求1中定义的化合物作为活性组分和杀真菌上可接受的载体或稀释剂。
10、杀真菌的方法，包括将权利要求1的化合物或权利要求3组合物用于植物或种子，或它们的存在的场所。
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CN1305858C (zh) * 2004-02-20 2007-03-21 沈阳化工研究院 取代唑类化合物及其制备与应用
US7795179B2 (en) 2004-02-20 2010-09-14 Shenyang Research Institute Of Chemical Industry Substituted azole compounds and its preparation and use thereof
CN103601716A (zh) * 2013-11-20 2014-02-26 厦门大学 一种苯并噻吩取代肟醚类化合物及其制备方法与应用
CN103980179A (zh) * 2014-05-29 2014-08-13 厦门大学 一种吲哚取代肟醚类化合物及其制备方法与应用
US10544092B2 (en) 2015-12-25 2020-01-28 Shenyang Sinochem Agrochemicals R&D Co., Ltd. Malononitrile oxime ether compound and use thereof
WO2017129121A1 (zh) * 2016-01-26 2017-08-03 南开大学 一类噻二唑肟醚甲氧基丙烯酸酯衍生物及其制备方法和用途
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US10906880B2 (en) 2016-01-26 2021-02-02 Nankai University Kind of isothiazole oxime ether-containing strobilurin derivatives and its preparation methods and application
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CN108191709B (zh) * 2016-12-08 2020-03-24 沈阳中化农药化工研发有限公司 一种制备不饱和肟醚类化合物的方法

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DK0569384T4 (da) 2000-12-04
EP0569384A1 (en) 1993-11-18
MA22400A1 (fr) 1992-10-01
DE69211983T2 (de) 1996-11-21
GB9200635D0 (en) 1992-03-11
WO1992013830A1 (en) 1992-08-20
EP0569384B2 (en) 2000-10-04
IE920144A1 (en) 1992-07-29
DE69211983D1 (de) 1996-08-08
DK0569384T3 (da) 1996-11-18
US5342837A (en) 1994-08-30
DE69211983T3 (de) 2000-12-28
IL100671A0 (en) 1992-09-06
ATE139993T1 (de) 1996-07-15
ES2088572T3 (es) 1996-08-16
EP0569384B1 (en) 1996-07-03
PT100072A (pt) 1993-03-31
AU1161992A (en) 1992-09-07

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