CN1042900A - 杀真菌剂 - Google Patents

杀真菌剂 Download PDF

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Publication number
CN1042900A
CN1042900A CN89108648A CN89108648A CN1042900A CN 1042900 A CN1042900 A CN 1042900A CN 89108648 A CN89108648 A CN 89108648A CN 89108648 A CN89108648 A CN 89108648A CN 1042900 A CN1042900 A CN 1042900A
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China
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unsubstituted
compound
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formula
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CN89108648A
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CN1024005C (zh
Inventor
保罗·约翰·迪弗雷恩
安妮·马丁
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Sinzeta 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=26294646&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CN1042900(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from GB888827149A external-priority patent/GB8827149D0/en
Priority claimed from GB898905383A external-priority patent/GB8905383D0/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Publication of CN1042900A publication Critical patent/CN1042900A/zh
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
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    • A—HUMAN NECESSITIES
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    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
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    • A01N43/08—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 five-membered rings with oxygen as the ring hetero atom
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Abstract

具有通式(I)的化合物及其立体异构体，式中A为一个特定的小基团，R1和R2选自很大范围内的特定取代基。这些化合物可用作杀真菌剂、杀虫剂和杀螨剂。

Description

本发明涉及可用作杀真菌剂、杀虫剂和杀螨剂的丙烯酸衍生物，它们的制备方法和含这些化合物的组合物，还涉及用这些化合物防治真菌（特别是真菌对植物的侵染）和杀死或控制昆虫和螨虫的方法。
本发明提供具有式（Ⅰ）的化合物及其立体异构体：
Figure 89108648X_IMG8
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烷氧羰基、苯氧基、硝基或氰基;R1和R2可以相同或不同，为氢、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的杂环基烷基、取代或未取代的环烷基烷基、取代或未取代的芳烷基、取代或未取代的杂芳基烷基、取代或未取代的芳氧基烷基、取代或未取代的杂芳氧基烷基、取代或未取代的链烯基、取代或未取代的炔基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的杂芳基、取代或未取代的芳氧基、取代或未取代的杂芳氧基、硝基、卤素、氰基、-NR3R4、-CO2R3、-CONR3R4、-COR3、-S（O）nR3（其中n是0、1或2）、（CH2）mPO（OR3）2（其中m为0或1），或R1和R2连在一起形成一个碳环或杂环体系;R3和R4可以相 同或不同，为氢、取代或未取代的烷基、取代或未取代的芳烷基、取代或未取代的链烯基、取代或未取代的炔基、取代或未取代的芳基、或取代或未取代的杂芳基。
本发明化合物含有至少一个碳-氮双键和至少一个碳-碳双键，因而有时以几何异构体混合物的形式制得。但是这些混合物可以分离为个别异构体，本发明包括这些异构体及其任何比例的混合物。
由于丙烯酸酯基和肟中的不对称取代的双键而形成的个别异构体用常用术语“E”和“Z”来表示。这些术语是按照Cahn-Ingold-Prelog体系定义的，这在文献中有充分的描述（例如参见J.March，“Advanced        Organic        Chemistry”，第3版，Wiley-Interscience出版，109页及其后部分）。
对于丙烯酸酯基的碳-碳双键来说，通常一种异构体比另一种异构体具有更强的杀真菌活性，活性较强的异构体通常是其中的-CO2CH3和-OCH3基团位于丙烯酸酯基烯键两侧的异构体（即（E）-异构体）。这些（E）-异构体构成本发明的优选实施方案。
卤素包括氟、氯、溴和碘。
烷基以及烷氧基、芳烷基和芳氧基烷基的烷基部分可以是直链或支链形式，并且除非另外指明，含有1～6个碳原子是合适的，例如甲基、乙基、异丙基和叔丁基。可有可无的取代基包括卤素（特别是氯和氟）、羟基和C1-4烷氧基。取代烷基和取代烷氧基的实例是三氟甲基和三氟甲氧基。
合适的环烷基是C3-6环烷基，例如环丙基和环己基，合适的环烷基烷基是C3-6环烷基（C1-4）烷基，例如环丙基乙基。
合适的链烯基和炔基含有2～6个碳原子，通常含2～4个碳原 子，为直链或支链形式，例如乙烯基、烯丙基和炔丙基。取代链烯基和炔基包括取代或未取代的芳基链烯基（特别是取代或未取代的苯基乙烯基）和芳炔基。
芳基以及芳烷基、芳基链烯基、芳炔基、芳氧基和芳氧基烷基中的芳基部分包括苯基和萘基。
R1和R2共同形成的合适的碳环或杂环体系是C5-10脂肪族、芳香族或脂肪/芳香族混合碳环体系，例如环戊基、环己基、环己二烯酮基和带有一个稠合苯环和/或取代基（如甲基）的这类基团;它也可是一个5～10员杂环体系，如四氢吡喃基。
术语杂芳基用来描述芳香族杂环基。杂芳基和杂环基以及其它基团（如杂芳氧基烷基和杂环基烷基）的杂芳基和杂环基部分，通常是含有一个或多个O、N或S杂原子的5或6员环，这些环可以与一个或多个其它芳香环、芳杂环或杂环例如苯环稠合，例如噻吩基、呋喃基、吡咯基、三唑基、噻唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、喹啉基和喹喔啉基，以及它们的N-氧化物。
可以存在于取代芳基和杂芳基部分的取代基包括一个或多个下述基团：卤素、羟基、巯基、C1-4烷基（尤其是甲基和乙基）、C2-4链烯基（尤其是烯丙基）、C2-4炔基（尤其是炔丙基）、C1-4烷氧基（尤其是甲氧基）、C2-4烯氧基（尤其是烯丙氧基）、C2-4炔氧基（尤其是炔丙氧基）、卤代（C1-4）烷基（尤其是三氟甲基）、卤代（C1-4）烷氧基（尤其是三氟甲氧基）、C1-4烷硫基（尤其是甲硫基）、羟基（C1-4）烷基、C1-4烷氧（C1-4）烷基、C3-6环烷基、C3-6环烷基（C1-4）烷基、取代或未取代的芳基（尤其是取代或未取代的苯基）、取代或未取代的杂芳基（尤 其是取代或未取代的吡啶基或嘧啶基）、取代或未取代的芳氧基（尤其是取代或未取代的苯氧基）、取代或未取代的杂芳氧基（尤其是取代或未取代的吡啶氧基或嘧啶氧基）、取代或未取代的芳基（C1-4）烷基（尤其是取代或未取代的苄基、取代或未取代的苯乙基和取代或未取代的苯基正丙基）（其中的烷基部分可由羟基取代）、取代或未取代的杂芳基（C1-4）烷基（尤其是取代或未取代的吡啶-或嘧啶（C1-4）烷基）、取代或未取代的芳基（C2-4）链烯基（尤其是取代或未取代的苯基乙烯基）、取代或未取代的杂芳基（C2-4）链烯基（尤其是取代或未取代的吡啶乙烯基或嘧啶乙烯基）、取代或未取代的芳基（C1-4）烷氧基（尤其是取代或未取代的苄氧基）、取代或未取代的杂芳基（C1-4）烷氧基（尤其是取代或未取代的吡啶-或嘧啶（C1-4）烷氧基）、取代或未取代的芳氧基（C1-4）烷基（尤其是苯氧甲基）、取代或未取代的杂芳氧基（C1-4）烷基（尤其是取代或未取代的吡啶氧基（C1-4）烷基或嘧啶氧基（C1-4）烷基）、酰氧基（包括C1-4链烷酰氧基（尤其是乙酰氧基）和苯甲酰氧基）、氰基、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″彼此独立地为氢、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，该苯基和苄基可由卤素、C1-4烷基或C1-4烷氧基取代。
任意上述取代基中的芳环或杂芳环上的取代基包括一个或多个下述取代基：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、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″具有上述意义。
本发明的一个方面包括式（Ⅰ）化合物，式中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烷氧羰基、氰基、苯基（C1-4）烷基、苯基、含有一个或多个O、N或S原子并且可与一个苯环稠合的五或六员芳香杂环，上述任一基团的芳香环部分或芳香杂环部分都可被一个或多个下列基团取代：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烷氧羰基、氰基或苯基;或者R1和R2连在一起形成一个C5-10碳环体系。
本发明的另一方面包括式（Ⅰ）化合物，式中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，上述任一基团的芳环部分或芳杂环部分都可被一个或多个下列基团取代：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;R2是氢、C1-4烷基、C1-4烷基羰基、C1-4烷氧羰基、氰基或苯基;或者R1和R2连在一起形成环戊基或环己基环，该环可以与一个苯环稠合。
本发明用下面表Ⅰ中列出的化合物来说明。整个表Ⅰ中的3-甲氧基丙烯酸甲酯基都是（E）构型。
Figure 89108648X_IMG9
Figure 89108648X_IMG10
Figure 89108648X_IMG12
Figure 89108648X_IMG13
Figure 89108648X_IMG14
Figure 89108648X_IMG16
Figure 89108648X_IMG17
Figure 89108648X_IMG18
Figure 89108648X_IMG20
Figure 89108648X_IMG22
Figure 89108648X_IMG23
Figure 89108648X_IMG24
Figure 89108648X_IMG25
表Ⅱ：所选择的质子NMR数据
表Ⅱ给出了表Ⅰ中所述的某些化合物的选定质子NMR数据。化学位移值是以四甲基硅烷为基准测出的，以ppm表示，全部以氘代氯仿为溶剂。“频率”一栏指的是核磁共振仪的操作频率。所用的缩写如下：
br＝宽峰
s＝单峰
d＝双峰
t＝三重峰
q＝四重峰
m＝多重峰
Figure 89108648X_IMG27
Figure 89108648X_IMG29
Figure 89108648X_IMG30
Figure 89108648X_IMG31
Figure 89108648X_IMG32
Figure 89108648X_IMG33
Figure 89108648X_IMG37
本发明的式（Ⅰ）化合物可以通过反应式1所示的步骤来制备。术语A、R1和R2定义如上，X是离去基团如卤素（氯、溴或碘）。
Figure 89108648X_IMG38
式（Ⅰ）化合物可以这样来制备：在适当的溶剂（如N，N-二甲基甲酰胺或四氢呋喃）中，用适当的碱（如氢化钠或甲醇钠）处理通式（Ⅲ）所示的肟，形成阴离子，然后加入式（Ⅱ）化合物。
通式（Ⅲ）的肟在化学文献中是熟知的化合物。欧洲专利申请0203606叙述了其中X是溴、丙烯酸酯基为（E）构型的通式（Ⅱ）化合物。
本发明式（Ⅰ）化合物也可按反应式2所示的步骤制备。术语A、R1、R2和X定义如上，R5是氢或金属（如钠或钾），L是离去基团，如卤离子（氯离子、溴离子或碘离子）、CH3SO4阴离子、或磺酸根阴离子。每一步转化反应都在适当的温度下并且通常（但不总是）在适当的溶剂中进行。
本发明的式（Ⅰ）化合物可由式（Ⅵ）的苯基乙酸酯或式（Ⅹ）的酮酯按反应式2所示的步骤制得。
这样，式（Ⅰ）化合物可通过用碱（如氢化钠或甲醇钠）和甲酸甲酯处理式（Ⅵ）的苯基乙酸酯来制备。如果向反应混合物中再加入式CH3L所示的化合物（其中L定义如上），便可得到式（Ⅰ）化合物。如果向反应混合物中加入一种质子酸，便得到式（Ⅸ）化合物（其中R5是氢）。式（Ⅸ）的化合物（其中R5是金属，如钠）本身也可从反应混合物中分离出来。
用化合物CH3L（L定义如上）处理式（Ⅸ）化合物（其中R5是金属），可将其转变成式（Ⅰ）化合物。依次用碱（如碳酸钾）和通式为CH3L的化合物处理式（Ⅸ）化合物（R5是氢），可将其转变为式（Ⅰ）化合物。
Figure 89108648X_IMG39
式（Ⅰ）化合物也可由式（Ⅳ）的缩醛通过在酸性或碱性条件下消除甲醇而制得。在这一转化中可以使用的试剂或试剂混合物的例子有二异丙基氨基锂;硫酸氢钾（例如参见T.Yamada，H.Hagiwara和H.Uda，J.Chem，Soc.Chemical        Communications        1980，838页和其中的参考文献）;以及三乙胺，通常是在路易斯酸如四氯化钛存在下（例如参见K.Nsunda和L.Heresi，J.Chem.Soc.Chemical        Communications，1985，1000页）。
式（Ⅳ）的缩醛类可通过使式（Ⅴ）（其中R是烷基）的乙烯酮缩甲醇甲硅烷醇在路易斯酸如四氯化钛存在下与原甲酸三甲酯反应制得（例如参见K.Saigo，M.Osaki和T.Mukaiyama，Chemistry        Letters，1976，769）。
式（Ⅴ）的乙烯酮缩甲醇甲硅烷醇类可由式（Ⅵ）的苯基乙酸酯与碱和式R3SiCl或R3SiBr所示的卤代三甲基硅烷（如氯代三烷基硅烷）或与碱（如三乙胺）和式R3Si-OSO2CF3的三氟甲磺酸三烷基硅酯反应制得（例如参见C.Ainsworth，F.Chen和Y.Kuo，J.Organometallic Chemistry，1972，46，59）。
并不总是需要分离中间体（Ⅳ）和（Ⅴ）;在适当的条件下，式（Ⅰ）化合物可以由式（Ⅵ）的苯基乙酸酯通过连续加入上述适当试剂进行“一釜反应”来制备。
式（Ⅵ）的苯基乙酸酯可以由式（Ⅶ）的苯基乙酸酯来制备。因此，如果使通式（Ⅲ）的肟与适当的碱（如氢化钠或甲醇钠）反应，并加入式（Ⅶ）的苯基乙酸酯，便可制得式（Ⅵ）的苯基乙酸酯。
式（Ⅶ）的苯基乙酸酯可通过在甲醇中使式（Ⅷ）的异苯并二氢吡喃酮与HX（其中X是卤素，如溴）反应制得。这一转变过程也可以分两步完成，即，使式（Ⅷ）的异苯并二氢吡喃酮在非醇性溶剂中与HX反应，然后将生成的苯基乙酸用标准方法酯化（例如参见I.Matsumoto和J.Yoshizawa，日本公开特许（Tokkyo        Koho）79138536，27.10.1979，Chem.Abs.，1980，92，180829h;G.M.F.Lim，Y.G.Perron和R.D.Droghini，Res.Discl.，1979，188，672，Chem.Abs.，1980，92，128526t）。式（Ⅷ）的异苯并二氢吡喃酮在化学文献中是熟知的化合物。
式（Ⅰ）化合物也可以通过使式（Ⅺ）的酮酯与甲氧亚甲基化试剂如甲氧基亚甲基三苯基正膦反应来制备（例如参见W.Steglich，G.Schramm，T.Anke和F.Oberwinkler，EP        0044        448，4.7.1980）。
式（Ⅺ）的酮酯可以通过使式（Ⅹ）的酮酯与上述通式（Ⅲ）的肟的阴离子反应制得。EP        0331        061叙述了式（Ⅹ）的酮酯类化合物。
本发明化合物是有效的杀真菌剂，可以用来控制一种或多种下述病原体：
稻谷上的Pyricularia        oryzae、
小麦上的隐藏双孢锈菌（Puccinia        recondita）、Puccinia        striiformis和其它锈病，大麦上的大麦霜孢锈菌、Puccinia        striiformis和其它锈病，以及其它宿主如咖啡、梨、苹果、花生、蔬菜和观赏植物上的锈病。
大麦和小麦上的麦类白粉菌（白粉病）以及各种宿主上的其它白粉粉病如啤酒花上的斑球壳霉（Sphaerotheca        macularis）、葫芦科植物（如黄瓜）上的黄瓜白粉病球壳霉、苹果上的苹果白粉病霉和葡萄树上的葡萄白粉病鉤丝壳霉。
谷物上的长蠕孢、嘴孢霉、壳针孢霉、核球壳菌、Pseudocercosporella        herpotrichoides和Gaeumannomyces        graminis。
花生上的花生褐斑病菌和Cercosporidium        personata以及其它宿主（例如甜菜、香蕉、大豆和稻）上的其它尾孢霉。
蕃茄、草莓、蔬菜、葡萄和其它宿主上的灰绿葡萄孢。
蔬菜（如黄瓜）、油菜、苹果、蕃茄和其它宿主上的交链孢。
苹果上的苹果黑星病菌。
葡萄上的葡萄霜霉菌。
其它霜霉病如莴苣上的莴苣霜霉病盘根霉，大豆、烟草、洋葱和其它宿主上的霜霉菌，啤酒花上的Pseudoperonospora        humuli和葫芦科植物上的瓜类假霜霉菌。
马铃薯和蕃茄上的马铃薯疫霉以及蔬菜、草莓、油梨、胡椒、观赏植物、烟草、可可树和其它宿主上的其它疫霉。
稻谷上的Thanatephorus        cucumeris以及其它宿主如小麦和大麦、蔬菜、棉花和草地上的其它丝核菌。
某些化合物在体外对真菌表现出广谱活性。它们对水果的各种采后病害（如桔子上的绿青霉和白边青霉以及绿色木霉，香蕉上的香蕉炭疽盘圆孢和葡萄上的灰绿葡萄孢）也具有活性。
此外，某些化合物作为拌种剂对下列真菌可能有活性：谷物上的 镰刀霉、壳针孢霉、腥黑粉菌（腥黑粉病，小麦的一种由种子传播的病害）、黑粉菌和长蠕孢;棉花上的马铃薯丝核菌以及稻谷上的Pyricularia        oryzae。
这些化合物在植物中可以具有内吸迁移作用。而且，这些化合物可能具有足够的挥发度，使其对于植物上的真菌在气相中也有活性。
因此，本发明提供了一种防治真菌的方法，它包括对植物、植物种子或者植物或种子所在地区施用杀真菌有效量的前面限定的化合物或者含有这类化合物的组合物。
某些化合物表现出杀虫活性，因而在适当的施用率下，可用来防治一定范围的昆虫和螨虫。
因此，本发明的另一方面提供一种杀伤或控制昆虫或螨虫的方法，该方法包括对昆虫或螨虫或者它们所在的地区施用杀虫或杀螨有效量的上面限定的化合物或含有这类化合物的组合物。
这些化合物可直接用于农业目的，但用载体或稀释剂配制成组合物则更方便。因此本发明提供含有上面限定的化合物和可接受的载体或稀释剂的杀真菌、杀虫和杀螨组合物。
这些化合物可采用多种方式施用。例如，可以配成制剂或不配成制剂而将它们直接施用于植物叶簇、种子或生长着植物或将要种植植物的介质，也可将它们以喷雾、喷粉方式或作为乳剂或糊剂施用，或者以蒸气或缓释颗粒剂形式施用。
可以施用于植物的任何部分、包括叶簇、茎、枝叉或根部，或施用于根部周围的土壤中，或在播种前施用于种子上，或普遍地施用于土壤中、稻田水中或水栽体系中。本发明化合物也可以注入植物内或用电动喷雾技术或其它低容量方法喷施到植物上。
此处所用术语“植物”包括籽苗、灌木和树木。此外，本发明的杀真菌方法包括预防、保护和铲除处理。
这些化合物最好以组合物形式用于农业和园艺目的。在任何情况下所用组合物的剂型都应根据所设定的具体目的来定。
这些组合物可以是可喷撒的粉剂或粒剂，其中包括活性成分（本发明化合物）和固体稀释剂或载体：例如填料如高岭土、膨润土、硅藻土、白云石、碳酸钙、滑石、粉状氧化镁、富勒氏土、石膏、硅藻土和瓷土。这样的粒剂可以制成不需进一步处理便适于在土壤中使用的颗粒。这些颗粒的制法是：或用活性成分浸渍填料颗粒，或将活性成分和粉末状填料的混合物制成小球状。拌种用的组合物可以包括一种粘附剂（例如矿物油），以有助于将组合物粘附在种子上;也可以用一种有机溶剂（如N-甲基吡咯烷酮、丙二醇或二甲基甲酰胺）将活性成分制成拌种用的制剂。这些组合物也可以是可湿性粉剂或水分散性粒剂，其中包括润湿剂或分散剂，使活性成分易于在液体中分散。该粉剂和粒剂中也可以含有填料和悬浮剂。
乳油或乳液的制法可以是：将活性成分溶于含或不含润湿剂或乳化剂的有机溶剂中，然后将此混合物加入水中，该水中也可以含有润湿剂或乳化剂。合适的有机溶剂是芳香溶剂如烷基苯和烷基萘;酮类如异佛尔酮、环己酮和甲基环己酮;氯代烃类如氯苯和三氯乙烷;以及醇类如苯甲醇、糠醇、丁醇和乙二醇醚类。
明显不溶性固体的悬浮浓缩物可以这样制备：将固体与分散剂和用来阻止固体沉降的悬浮剂一起球磨或珠磨。
用于喷雾的组合物可以是气雾剂形式，其中的制剂保持在内含加压推进剂（如氟代三氯甲烷或二氯二氟甲烷）的容器中。
本发明化合物可以以干态形式与焰火混合物混合成为适于在密闭空间产生含该化合物的烟雾的组合物。
这些化合物也可以微囊包封形式使用。也可以将它们制成可生物降解的聚合物剂型，这样可以使活性物质缓慢地受控制地释放出来。
通过加入适当的添加剂，例如改进分布状况、改进粘附能力和提高处理表面抗雨能力的添加剂，可使各种不同的组合物更好地适应各种用途。
本发明化合物可与肥料（如含氮、含钾或含磷的肥料）混合后使用。仅包括掺合（例如涂覆）该化合物的肥料颗粒的组合物比较好。这种颗粒含有至多25%（重量）该化合物较合适。因此本发明也提供一种肥料组合物，其中包含一种肥料和通式（Ⅰ）化合物或其盐或金属络合物。
可湿性粉剂、乳油和悬浮浓缩物通常含有表面活性剂，例如润湿剂、分散剂、乳化剂或悬浮剂。这些添加剂可以是阳离子型、阴离子型或非离子型。
合适的阳离子表面活性剂是季铵化合物，例如溴化十六烷基三甲基铵。合适的阴离子表面活性剂是皂类、硫酸的脂肪单酯盐类（如月桂基硫酸钠）以及磺化芳香化合物的盐类（例如十二烷基苯磺酸钠，木素磺酸钠、钙或铵盐，丁基萘磺酸盐，以及二异丙基-和三异丙基萘磺酸钠的混合物）。
合适的非离子型表面活性剂是环氧乙烷与脂肪醇（如油醇或十六醇）或烷基酚（如辛基酚、壬基酚和辛基甲酚）的缩合产物。其它非离子型表面活性剂是由长链脂肪酸和脱水己糖醇衍生的部分酯、所述部分酯与环氧乙烷的缩合产物和卵磷脂。合适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）和溶胀粘土如膨润土或硅镁土。
用作水分散液或乳液的组合物通常以含高比例活性成分的浓缩物形式供应，该浓缩物在使用前用水稀释。这些浓缩物最好能经受长期贮存，并且这样贮存以后，仍能用水稀释，以便形成能在足够长的时间内保持均相的含水制剂，以使它们能用常规的喷雾设备施用。该浓缩物可以方便地含有至多95%（重量）的活性成分，含10-85%较合适，例如含25-60%。稀释成为含水制剂以后，根据预期的目的，这种含水制剂可以含有不同量的活性成分，但可以使用含有0.0005%或0.01%至10%（重量）活性成分的含水制剂。
本发明组合物可以含有具有生物活性的其它化合物，例如具有类似或互补杀真菌活性或者具有植物生长调节、除草或杀虫活性的化合物。
可以存在于本发明组合物中的杀真菌化合物可以能够防治谷类（如小麦）穗病（如壳针孢霉、赤霉和长蠕孢）、种子和土壤传播的病害、以及葡萄上的霜霉和白粉菌和苹果上的白粉菌和斑点病等。通过在组合物中加入另一种杀真菌剂，使其能比单独的通式（Ⅰ）化合物具有更广谱的活性。此外，其它杀真菌剂可对通式（Ⅰ）化合物的杀真菌活性具有增效作用。可以包含在本发明组合物中的杀真菌化合物的实例有：（±）-2-（2，4-二氯苯基）-3-（1H-1，2，4-三唑-1-基）丙基1，1，2，2-四氟乙基醚、（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、（RS）-4-氯-N-（氰基（乙氧基）甲基）苯甲酰胺、（Z） -N-丁-2-烯氧甲基-2-氯-2′，6′-二乙基乙酰苯胺、1-（2-氰基-2-甲氧基亚氨基乙酰基）-3-乙基脲、1-〔2RS，4RS;2RS，4RS）-4-溴-2-（2，4-二氯苯基）四氢糠基〕-1H-1，2，4-三唑、3-（2，4-二氯苯基）-2-（1H-1，2，4-三唑-1-基）喹唑啉-4（3H）-酮、3-氯-4-〔4-甲基-2-（1H-1，2，4-三唑-1-甲基）-1，3-二氧戊环-2-基〕苯基-4-氯苯基醚、4-溴-2-氰基-N，N-二甲基-6-三氟甲基苯并咪唑-1-磺酰胺、N-（2，4-二氯苯基）-2-（1H-1，2，4-三唑-1-基硫代乙酰胺4-氯苄基酯、5-乙基-5，8-二氢-8-氧代（1，3）-二氧戊环并〔4，5-g〕喹啉-7-羧酸、α-〔N-（3-氯-2，6-二甲苯基）-2-甲氧基乙酰胺基〕-γ-丁内酯、敌菌灵、BAS        454、benalaxyl、苯菌灵、biloxazol、乐杀螨、bitertanol、灭瘟素、磺酸丁嘧啶、buthiobate、敌菌丹、克菌丹、多菌灵、莠锈灵、chlorbenzthiazone、地茂散、百菌清、chlorozolinate、含铜化合物（如王铜、硫酸铜和波尔多液）、放线菌酮、cymoxanil、cyproconazole、cyprofuram、二-2-吡啶基二硫化物1，1′-二氧化物、抑菌灵、二氯苯醌、dichlobutrazol、bichlomezine、氯硝胺、dimethamorph、甲菌定、diniconazole、敌螨普、灭菌磷、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羰基）氨基〕硫代）-β-氨基丙酸乙酯、etridazole、fenapanil、双氯 苯嘧醇、一甲呋萎灵、fenpiclonil、fenpropidin、fenpropimorph、乙酸三苯基锡、三苯羟基锡、flutolanil、flutriafol、fluzilazole、灭菌丹、fosetyl-aluminium、麦穗宁、furalaxyl、furconazole-cis、双胍盐、hexaconazole、土菌消、imazalil、iprobenfos、iprodione、富士一号、春雷霉素、代森锰锌、代森锰、mepronil、metalaxyl、methfuroxam、metsulfovax、myclobutanil、甲胂铁铵、二甲基二硫代氨基甲酸镍、nitrothal-isopropyl、nuarimol、ofurace、有机汞化合物、oxadixyl、氧化萎锈灵、penconazole、pencycuron、N-糠基-N-咪唑-1-基羰基-DL-高丙氨酸戊-4-烯基酯、5-氧吩嗪、四氯苯酞、多氧霉素、代森联、噻菌灵、prochloraz、procymidone、propamocarb、propiconazole、甲基代森锌、胺丙威、定菌磷、pyrifenox、pyroquilon、pyroxyfur、pyrrolnitrin、甲基克杀螨、五氯硝基苯、链霉素、硫黄、techlofthalam、四氯硝基苯、tebuconazole、涕必灵、甲基托布津、福美双、tolclofos-methyl、1，1′-亚氨基二（八亚甲基）二胍三乙酸盐、三唑二甲酮、triadimenol、triazbutyl、三唑苯噻、环吗啉、嗪氨灵、有效霉素、vinclozolin、代森锌。通式（Ⅰ）的化合物可以与土壤、泥炭或其它生根介质混合以保护植物抵抗由种子和土壤传播的或叶片真菌性病害。
可以掺入本发明组合物中的合适杀虫剂包括buprofezin、西维因、虫螨威、carbosulfan、毒死蜱、cycloprothrin、 甲基一○五九、二嗪农、乐果、ethofenprox、杀螟松、fenobucarb、倍硫磷、安果、异丙威、异噁唑磷、久效磷、稻丰散、抗蚜威、丙虫磷、二甲威。
植物生长调节化合物是抑制杂草或籽芽的形成，或选择性地抑制不良植物（如草类）生长的化合物。
与本发明化合物共用的合适的植物生长调节化合物的实例有：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、长杀草、丁酰肼、离子草吡唑、dikegulac、乙烯利、fenpentezol、氟磺安、草甘膦、催熟膦、羟基苯基腈类（如溴草腈）、inabenfide、isopyrimol、长链脂肪醇和酸、抑芽丹、mefluidide、整形素（如氯芴素）、paclobutrazol、苯氧乙酸（如2，4-滴或2甲4氯）、取代的苯甲酸（如三碘苯甲酸）、取代的季铵和鏻化合物（如chloromequat、氯化鏻或mepiquatchloride）、四氯硝基苯、植物生长激素类（如吲哚乙酸、吲哚丁酸、萘乙酸或萘氧乙酸）、细胞激动素（如苯并咪唑、苄基腺嘌呤、苄基-6-氨基嘌呤、二苯脲或激动素）、赤霉酸类（如GA3、GA4或GA7）、triapenthenol。
下面的实例说明本发明。所有实例中的术语“醚”都指乙醚，用硫酸镁来干燥溶液，在减压条件下浓缩溶液。凡是涉及对空气或水敏感的中间体的反应都是在氮气氛中进行并且使用预先干燥过的溶剂。除非另外指明，层析操作都是在以硅胶为固定相的柱上进行。所给出的红外和NMR数据是经过选择的，不打算列出所有情况下的每个吸 收值。除非另外指明，1H NMR谱是用CDCl3溶液记录的。通篇所用的缩写如下：
THF＝四氢呋喃        s＝单峰
DMF＝N，N-二甲基甲酰胺        d＝双峰
NMR＝核磁共振        t＝三重峰
IR＝红外光谱        m＝多重峰
m.p.＝熔点        br＝宽峰
HPLC＝高效液相层析。
实例1
本实例说明（E），（E）-3-甲氧基-2-〔2-（3-甲基苯甲醛肟基甲基）苯基〕丙烯酸甲酯（表Ⅰ中化合物5）的制备方法。
在室温下将（E）-3-甲基苯甲醛肟（0.23g）的DMF（5ml）溶液滴加到氢化钠（0.051g）在DMF（5ml）中的搅拌悬浮液中。半小时后，将（E）-2-〔2-（溴甲基）苯基〕-3-甲氧基丙烯酸甲酯（0.5g，按EP-A-0203606所述方法制备）的DMF（5ml）溶液加到反应混合物中，然后室温下搅拌4小时。将混合物倒入水中并用乙醚提取2次。合并的提取物用水洗涤，然后干燥、浓缩并用乙醚为洗脱液层析，得到标题化合物（0.132g，23%产率），为浅黄色油状物。
IR最大吸收（膜）：1709，1631cm-1。
1H NMR（270 MHz）δ：2.35（3H，s）;3.69（3H，s）;3.80（3H，s）;5.12（2H，s）;7.1-7.55（8H，m）;7.59（1H，s）;8.05（1H，s）ppm.
实例2
本实例说明2-〔2-（3，5-二甲基吡嗪-2-基-乙醛肟基甲基）苯基〕-3-甲氧基丙烯酸甲酯的（E），（E）和（Z），（E）混合物（表Ⅰ中化合物176）的制备方法。
向0℃下搅拌着的2，6-二甲基吡嗪（3.24g）、硫酸（15ml3.4M溶液）和乙醛（10ml）的混合物中同时加入硫酸亚铁溶液（50.1g，在150ml水中）和叔丁基过氧氢（16.2ml，70%水溶液），加料过程中的温度保持在3℃以下。加完后将混合物在0℃搅拌1小时。加入焦硫酸氢钠，直到对混合物的淀粉-碘试验呈阴性。用二氯甲烷提取反应混合物，合并提取液，用水洗涤，然后干燥，浓缩，并用乙醚和60-80℃石油醚的混合物（4∶1）作洗脱液进行层析，得浅黄色油状的2-乙酰基-3，5-二甲基吡嗪（2.65g，59%产率）。
IR最大吸收（膜）：1694，1551，1262，1175cm-1.
1H NMR（270 MHz）δ：2.62（3H，s），2.70（3H，s），2.80（3H，s），8.36（1H，s）ppm.
将2-乙酰基-3，5-二甲基吡嗪（2.65g）、盐酸羟胺（2.5g）和三水乙酸钠（3.5g）在甲醇（50ml）中回流1小时。将反应混合物浓缩，用水（75ml）稀释并用乙酸乙酯提取。将合并的提取液干燥并浓缩，得油状物，将其用乙醚和60-80℃石油醚研制，得3，5-二甲基-2-（1-肟基乙基）吡嗪（2.54g，87%产率）白色固体（m.p.85-89℃），为（E/Z）异构体（1∶1）的混合物。
IR最大吸收（膜）：2925，1465，1376，1086，930cm-1.1H NMR（270 MHz）δ：2.23（3H，s），2.33（3H，s），2.53（3H，s），2.56（3H，s），2.58（3H，s），2.68（3H，s），8.32（1H，s），8.35（1H，s），9.45（1H，br.s），9.85（1H，br.s）ppm.
在约5℃下，将（E/Z）-3，5-二甲基-2-（1-肟基乙基）吡嗪（0.87g）（1∶1）混合物分批加到氢化钠（0.25g）在DMF（20ml）中的搅拌悬浮液中。1小时后，将（E）-2-〔2-（溴甲基）苯基〕-3-甲氧基丙烯酸甲酯（1.5g）的DMF（5ml）溶液加到反应混合物中。1.5小时后，将该混合物倒入水中，用乙醚提取2次。合并提取液，用盐水洗涤，然后干燥，浓缩，并用乙醚∶己烷（1∶1）为洗脱剂进行层析，得标题化合物，为肟异构体混合物（主要成分∶次要成分为7∶3），浅粉色固体（0.57g，30%产率），m.p.56-60℃。IR最大吸收（膜）：1707，1624，1132cm-1。
1H NMR（270MHz）主要异构体 -δ：2.39（3H，s），2.54（3H，s），2.57（3H，s），3.67（3H，s），3.82（3H，s），5.15（2H，s），7.1-7.9（4H，m），7.59（1H，s），8.27（1H，s）ppm.次要异构体 -δ：2.22（3H，s），2.51（3H，s），2.57（3H，s），3.67（3H，s），3.82（3，Hs），5.27（2H，s），7.1-7.9（4H，m），7.76（1H，s），8.33（1H，s）ppm.
实例3
本实例说明（E），（E）-3-甲氧基-2-〔2-（苯基乙醛肟基甲基）苯基〕丙烯酸甲酯（表Ⅰ中化合物23）的制备方法。
将苯乙酮肟（1.23g）的DMF（5ml）溶液，滴加到氢化钠（0.367g）在DMF（25ml）中的搅拌悬浮液中。1小时后，向反应混合物中加入（E）-2-〔2-（溴甲基）苯基〕-3-甲氧基丙烯酸甲酯（2.0g）的DMF（15ml）溶液，然后在室温下搅拌16小时。将混合物倒入水中并用乙醚提取2次。 合并提取液，用水洗涤，然后干燥，浓缩，并用乙醚∶40-60℃石油醚（3∶2）进行层析，得到油状粗品。用乙醚∶40-60℃石油醚（1∶1）进行高效液相层析，得标题化合物（0.55g，23%产率），为浅黄色油状物。
IR最大吸收（膜）：1708，1631cm-1。
1H NMR数据见表Ⅱ。
实例4
本实例说明3-甲氧基-2-｛2-〔（嘧啶-5-基异丙基酮肟基）-O-甲基〕苯基｝丙烯酸甲酯的（E），（E）和（Z），（E）异构体（表Ⅰ中化合物66和67）的制备和分离方法。
将异丙基嘧啶-5-基酮肟（0.29g（E）∶（Z）异构体的3∶2混合物）的DMF（5ml）溶液加到氢化钠（0.09g）在DMF（10ml）中的搅拌悬浮液中。2小时后，将混合物冷至0℃，向其中加入（E）-2-〔2-（溴甲基）苯基〕-3-甲氧基丙烯酸甲酯（0.5g）的DMF（5ml）溶液，然后搅拌3小时。将混合物倒入水中，用乙醚提取。合并提取液，用水洗涤，然后干燥并浓缩，得油状粗产品，为（E），（E）和（Z），（E）异构体混合物。用乙醚作洗脱液进行高效液相层析，将这两个异构体分离为两种个别组分。
1.较快洗脱出的组分为（Z）-肟醚，（E）-丙烯酸酯（0.115g，18%产率）。清亮油状物（表Ⅰ中化合物67）。
2.较慢洗脱出的组分为（E）-肟醚，（E）-丙烯酸酯（0.098g，15%产率）。清亮油状物（表Ⅰ中化合物66）。
1H NMR数据示于表Ⅱ。
实例5
本实例说明2-〔2-（苯基〔甲硫基〕酮肟基甲基）苯基〕-3-甲氧基丙烯酸甲酯的一种立体异构体（表Ⅰ中化合物191）的制备方法。
在室温下将氯（1.5g）的四氯化碳（42ml）溶液分批加到苯甲醛肟〔2.5g;1H NMR：δ 8.18（1H，s），9.40（1H，brs）ppm〕在四氯化碳（20ml）中的搅拌的部分溶液中。加完以后，将反应混合物在室温下搅拌3小时，然后倒入水中。分出有机层，干燥并浓缩，得到几乎是纯的α-氯苯甲醛肟（3.2g）黄色液体。将甲硫醇钠（0.68g）的甲醇（15ml）溶液滴加到部分上述α-氯苯甲醛肟（1.5g）在甲醇（15ml）中的冰冷并搅拌的溶液中。加完以后，将反应混合物在持续用冰-水冷却情况下搅拌2小时。减压除去甲醇，残余物用二氯甲烷作洗脱剂层析，得到α-甲硫基苯甲醛肟单个立体异构体（0.670g，42%产率），为白色结晶固体，m.p.76-78℃，1H NMR：δ2.08（3H，s），9.12（1H，s）ppm。
在室温下，将α-甲硫基苯甲醛肟（0.575g）的DMF（10ml）溶液滴加到氢化钠（85mg）在DMF（15ml）中的搅拌悬浮液中。1小时后，向其中滴加（E）-2-〔2-（溴甲基）苯基〕-3-甲氧基丙烯酸甲酯（0.990g）的DMF溶液，再过3小时后，将混合物倒入水中并用乙酸乙酯提取。有机提取液用水洗涤，干燥，浓缩，并用在己烷中不断增加乙酸乙酯比例的混合液为洗脱剂进行层析，得到标题化合物（1.05g，83%）， 为无色油状物。
IR：1706cm-1。
1H NMR数据示于表Ⅱ。
实例6
本实例说明2-〔2-（苯基〔甲基亚磺酰基〕酮肟基甲基）苯基〕-3-甲氧基丙烯酸甲酯和2-〔2-（苯基〔甲基磺酰基〕酮肟基甲基）苯基〕-3-甲氧基丙烯酸甲酯单个立体异构体（表Ⅰ中化合物227和228）的制备方法。
用30分钟将间氯过苯甲酸（0.250g，含45%间氯过苯甲酸）分批加到用冰水冷却的2-〔2-（苯基〔甲硫基〕酮肟基甲基）苯基〕-3-甲氧基丙烯酸甲酯（0.300g，按实例5所述方法制备）在二氯甲烷（20ml）中的搅拌溶液中。再过15分钟后，将反应混合物依次用碳酸氢钠水溶液和水洗涤，然后干燥，浓缩，并用乙酸乙酯和己烷1∶1混合物为洗脱剂进行层析，得到标题化合物：（ⅰ）砜，首先洗脱出来，为胶状物（0.090g，28%产率）;（ⅱ）亚砜，也是胶状物（0.150g，48%产率）。
1H NMR数据示于表Ⅱ。
实例7
本实例说明2-〔2-（苯基〔甲氧基〕酮肟基甲基）苯基〕-3-甲氧基丙烯酸甲酯的两种立体异构体（表Ⅰ中化合物225和226）的制备方法。
由苯甲酸甲酯，通过依次用Lawesson氏试剂和羟胺处理，分两步制得α-甲氧基苯甲醛肟的立体异构体混合物（例如参见EP        0        299        382）。用二氯甲烷作洗脱剂层析分离这些立体异构体： （ⅰ）异构体A，首先洗脱出来，为浅黄色固体，m.p.55-57℃，1H NMR：δ 3.83（3H，s），7.72（1H，s）ppm;
（ⅱ）异构体B，无色胶状物，1H NMR：δ 3.96（3H，s），8.84（1H，s）ppm。
将这两种立体异构体的肟用实例5所述的方法分别转化成标题化合物，即依次用氢化钠和（E）-2-〔2-（溴甲基）苯基〕-3-甲氧基丙烯酸甲酯反应。由异构体A得到表Ⅰ中的225号标题化合物，为胶状物;由异构体B得到表Ⅰ中的226号标题化合物，也为胶状物。
1H NMR数据示于表Ⅱ中。
下面是一些可由本发明化合物制备的适于农业和园艺目的的组合物的实例。这些组合物构成本发明的另一方面。百分比以重量计。
实例8
将下列各组分混合并搅拌，直至全部溶解，制得一种乳油。
表Ⅰ中化合物45        10%
苯甲醇        30%
十二烷基苯磺酸钙        5%
壬基酚乙氧化物（13摩尔环氧乙烷）        10%
烷基苯        45%
实例9
将活性成分溶于二氯甲烷，将所得液体喷到硅镁土颗粒上。然后使溶剂蒸发，制成颗粒组合物。
表Ⅰ中化合物45        5%
硅镁土颗粒        95%
实例10
将下面三种成分磨细并混合，制得适于拌种用的组合物。
表Ⅰ中化合物45        50%
矿物油        2%
瓷土        48%
实例11
将下述活性成分与滑石磨细并混合，制得可喷施的粉末。
表Ⅰ中化合物45        5%
滑石        95%
实例12
将下述成分球磨，形成磨细的混合物与水的含水悬浮液，制得悬浮浓缩物。
表Ⅰ中化合物45        40%
木素磺酸钠        10%
膨润土        1%
水        49%
可将该制剂稀释至水中用作喷雾液，也可将该制剂直接用于种子。
实例13
将下列成分混合并磨细，直到所有成分充分混合，制得可湿性粉剂。
表Ⅰ中化合物45        25%
月桂基硫酸钠        2%
木素磺酸钠        5%
硅石        25%
瓷土        43%
实例14
用该化合物对植物各种叶面真菌病害进行了试验。所用技术如下。
将植物种植在直径4cm的小花盆中的John        Innes盆栽堆肥（1或2号）中。通过与含水Dispersol        T一起珠磨或通过溶于丙酮或丙酮/乙醇中制成溶液，将试验化合物加工成制剂，临使用前将其稀释至所需浓度。对于叶簇病害，将制剂（100ppm活性成分）喷到叶簇上并施于土壤中植物的根部。喷雾达到最大保留，根部灌药达到终浓度相当于干燥土壤中大约有40ppm活性成分。向谷物喷雾施药时，加入吐温20达到终浓度0.05%。
对于大多数试验，在对植物接种病害前一天或两天，将化合物施于土壤（根部）和叶簇（喷雾）。对麦类白粉菌的试验是一个例外，它是在处理前24小时接种植物。施用叶面病原体的方法是将孢子悬浮液喷到待试植物的叶子上。接种以后，将植物放在适当的环境中，使感染继续，然后进行培养，直到可以对病害进行评估。从接种到评定之间的时间间隔视病害和环境条件不同为4到14天不等。
病害抑制情况按下述等级记录：
4＝无病害
3＝痕量至未处理植株病害的5%
2＝未处理植株病害的6-25%
1＝未处理植株病害的26-59%
0＝未处理植株病害的60-100%
结果示于表Ⅲ。
实例15
式（Ⅰ）化合物的杀虫性能说明如下：
化合物的活性用各种昆虫、螨虫和线虫进行测定。除了对家蝇的击倒活性试验方法将在后面叙述以外，该化合物以含12.5～1000ppm（重量）化合物的液体制剂形式使用。制剂的制备方法是：将化合物溶于丙酮，用含0.1%（重量）以商品名“SYNPERONIC”NX出售的润湿剂的水稀释所得溶液，直到液体制剂中含有的产品达到所需浓度。“SYNPERONIC”为注册商标。
对各种害虫采用的试验方法基本上是相同的，都包括：将一些害虫放在介质上，该介质通常是作为害虫食物的宿主植株或饲料;用制剂处理害虫和介质中的任意一种或两者都进行处理。通常在处理后一至七天的时间内评定害虫死亡率。
表Ⅳ中给出对第一栏列出的各化合物以第二栏给出的施用率（ppm）进行试验的结果。这些结果表示为死亡率等级9、5或0，其中9表示80-100%死亡率（对假根结线虫半体外试验，为与未处理植株相比根结病减少70-100%），5表示50-79%死亡率（对假根结线虫半体外试验，根结病减少50-69%），0表示死亡率小于50%。
表Ⅳ中用字码表示所用的害虫种类。字码的意义、支持介质或食料，以及试验的类型和持续时间列在表Ⅴ中。
对家蝇的击倒性能说明如下。
将化合物样品以0.1%稀释在乙醇/丙醇（50∶50混合物）中，用0.1%的Synperonic        NX水溶液将其制成1000ppm的溶液。然后将此溶液（1ml）直接喷雾于酒杯中的10只雌雄混合家蝇和一个块糖上。
喷雾后，立即将酒杯倒置使之干燥。15分钟后将酒杯立起，进行击倒性能的评定。然后将家蝇置于湿的棉毛垫上。在调节在25℃和65%相对湿度的保存室中保持48小时，然后进行死亡率评定。
Figure 89108648X_IMG40
Figure 89108648X_IMG41
Figure 89108648X_IMG43
Figure 89108648X_IMG44
Figure 89108648X_IMG45
Figure 89108648X_IMG46
Figure 89108648X_IMG47
Figure 89108648X_IMG48
Figure 89108648X_IMG50
表Ⅴ
字码        试验物种        支持介质/食料        试验类型        持续时间
（表Ⅳ）        （天）
TU        AC        棉叶螨        法国菜豆叶        接触        3
（成虫）
TU        EO        棉叶螨        法国菜豆叶        接触        3
（卵）
TU        NG        棉叶螨        法国菜豆叶        接触        6
（若虫）        （生长）
MP        MC        桃蚜        白菜叶        接触        3
NC        NC        黑尾叶蝉        稻植株        接触        2
（若虫）
NC        NG        黑尾叶蝉        稻植株        接触        6
（若虫）        （生长）
表Ⅴ（续）
字码        试验物种        支持介质/食料        试验类型        持续时间
（表Ⅳ）        （天）
MD        AK        家蝇        塑料花盆        接触        15分
（成虫）        （击倒）
MD        AC        家蝇        塑料花盆        接触        3
（成虫）
BG        NK        德国蠊        塑料花盆        接触        15分
（若虫）        （击倒）
BG        NC        德国蠊        塑料花盆        接触        2
（若虫）
HV        LR        烟芽夜蛾        棉叶        残留        2
（幼虫）
HV        LG        烟芽夜蛾        棉叶        残留        5
（幼虫）        （生长）
表Ⅴ（续）
字码        试验物种        支持介质/食料        试验类型        持续时间
（表Ⅳ）        （天）
SP        LR        甜菜夜蛾        棉叶        残留        2
（幼虫）
SP        LG        甜菜夜蛾        棉叶        残留        2
（幼虫）        （生长）
DB        LR        带斑黄瓜叶甲        滤纸/玉米种子        残留        2
（幼虫）
MI        JC        假根结线虫        体外        接触        1
（幼虫）
“接触”试验是指害虫和介质都进行过处理，“残留”是指用害虫侵染以前处理介质。

Claims (8)

1、具有结构式(Ⅰ)的化合物及其立体异构体：
Figure 89108648X_IMG2
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烷氧羰基、苯氧基、硝基或氰基；R1和R2可以相同或不同，为氢、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的杂环基烷基、取代或未取代的环烷基烷基、取代或未取代的芳烷基、取代或未取代的杂芳基烷基、取代或未取代的芳氧基烷基、取代或未取代的杂芳氧基烷基、取代或未取代的链烯基、取代或未取代的炔基、取代或未取代的烷氧基、取代或未取代的芳基、取代或未取代的杂芳基、取代或未取代的芳氧基、取代或未取代的杂芳氧基、硝基、卤素、氰基、-NR3R4、-CO2R3、-CONR3R4、-COR3、-S(O)nR3(其中n是0、1或2)、(CH2)mPO(OR3)2(其中m为0或1)，或R1和R2连在一起形成一个碳环或杂环体系；R3和R4可以相同或不同，为氢、取代或未取代的烷基，取代或未取代的芳烷基、取代或未取代的链烯基、取代或未取代的炔基、取代或未取代的芳基或取代或未取代的杂芳基。
2、根据权利要求1的化合物，其特征在于，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原子并且可与一个苯环稠合的五或六员芳香杂环，上述任一基团中的芳香或杂芳环部分都可被一个或多个下述基团取代：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烷氧羰基、氰基或苯基;或R1和R2连在一起形成一个C5-10碳环体系。
3、根据权利要求1的化合物，其特征在于，A是氢或卤素;R1是C1-4烷基、苄基、C1-4烷基羰基、C1-4烷氧羰基、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，上述任一基团中的芳香或杂芳环部分都可被一个或多个下述基团取代：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;R2是氢、C1-4烷基、C1-4烷基羰基、C1-4烷氧羰基、氰基或苯基;或者R1和R2连在一起形成环戊基或环己基环，该环可与一个苯环稠合。
4、权利要求1所述化合物的制备方法，该方法包括在碱性条件下使式（Ⅱ）化合物与式（Ⅲ）所示肟的盐反应：
Figure 89108648X_IMG3
式中A具有权利要求1中所给定的定义，X是离去基团，
Figure 89108648X_IMG4
式中R1和R2具有权利要求1中所给定的定义。
5、权利要求1所述化合物的制备方法，该方法包括
（a）使式（Ⅸ）化合物与式CHL化合物反应，
;或者
（b）在酸性或碱性条件下由式（Ⅳ）化合物中消除甲醇，
（c）使式（Ⅺ）的酮酯与一种甲氧基亚甲基化试剂反应，
Figure 89108648X_IMG7
式中A、R1和R2具有权利要求1中所给定的定义，L是离去基团，R5是金属原子。
6、一种杀真菌剂、杀虫剂或杀螨剂组合物，其中包括作为活性成分的权利要求1所限定的化合物和杀真菌剂、杀虫剂或杀螨剂中可接受的载体或稀释剂。
7、一种防治真菌的方法，包括对植物、植物种子或其所在场所施用杀真菌有效量的权利要求1限定的化合物。
8、一种杀灭或控制昆虫或螨虫的方法，包括对昆虫或螨虫或其所在场所施用杀虫或杀螨有效量的权利要求1限定的化合物。
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101372470B (zh) * 2008-10-16 2013-05-15 国家农药创制工程技术研究中心 具有杀虫、杀菌活性的肟醚甲氧丙烯酸酯类化合物
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
WO2017129122A1 (zh) * 2016-01-26 2017-08-03 南开大学 一类异噻唑肟醚甲氧基丙烯酸酯衍生物及其制备方法和用途
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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CA2003480C (en) 2003-10-21
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NZ231242A (en) 1991-05-28
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US5631253A (en) 1997-05-20
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IE64709B1 (en) 1995-08-23
KR0133666B1 (ko) 1998-04-21
AP8900147A0 (en) 1990-01-31
GB8924122D0 (en) 1989-12-13
RU2024496C1 (ru) 1994-12-15
AP127A (en) 1991-03-20
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US5432197A (en) 1995-07-11
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EP0370629B2 (en) 1998-01-07
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