CN1650707B - 基于酰胺化合物和吡啶衍生物的杀真菌混合物 - Google Patents
基于酰胺化合物和吡啶衍生物的杀真菌混合物 Download PDFInfo
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- CN1650707B CN1650707B CN2005100043169A CN200510004316A CN1650707B CN 1650707 B CN1650707 B CN 1650707B CN 2005100043169 A CN2005100043169 A CN 2005100043169A CN 200510004316 A CN200510004316 A CN 200510004316A CN 1650707 B CN1650707 B CN 1650707B
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- 125000002098 pyridazinyl group Chemical group 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
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Classifications
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明涉及杀真菌混合物，它包含增效有效量的a)式I酰胺化合物，其中A、R1和R2如说明书中所定义，和b)式II化合物、其N-氧代物或其盐，其中取代基R12至R18如说明书中所定义，和/或c)式II化合物，其中取代基X1至X5和R19至R22如说明书中所定义。A-CO-NR1R2(I)
Description
本申请是申请号为98812315.0、申请日为1998年12月15日的中国发明专利申请的分案申请。
本发明涉及防治有害真菌的杀真菌混合物，所述混合物包含增效量的式I酰胺化合物
A-CO-NR1R2 (I)
其中
A 是芳基或具有1至3个选自O、N和S的杂原子的芳香或非芳香的5-或6-元杂环；
其中所述芳基或杂环可以具有或不具有1、2或3个相互独立地选自下列的取代基：烷基、卤素、CHF2、CF3、烷氧基、卤代烷氧基、烷硫基、烷基亚磺酰基和烷基磺酰基；
R1是氢原子；
R2是苯基或环烷基，它可以具有或不具有1、2或3个选自下列的取代基：烷基、烯基、炔基、烷氧基、烯氧基、炔氧基、环烷基、环烯基、环烷基氧基、环烯基氧基、苯基和卤素，其中所述的脂族和环脂族基团可以部分或全部被卤代和/或环脂族基团可以被1至3个烷基取代，而其中苯基可以具有1至5个卤原子和/或1至3个相互独立地选自下列的取代基：烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基和卤代烷硫基，且其中酰胺苯基可以与或不与饱和5-元环稠合，而所述的5-元环可以被或未被一个或多个烷基取代和/或可以具有选自O和S的杂原子，
和
式II化合物、其N-氧化物或其盐
其中取代基如下定义：
R12、R13、R14、R15相互独立地是氢、羟基、硝基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-卤代烷硫基；
R16、R17、R18相互独立地是氢、羟基、氰基、硝基、卤素、C1-C7-烷基、C1-C7-卤代烷基、C1-C7-烷氧基、C1-C7-卤代烷氧基、C1-C7-烷硫基、C1-C7-卤代烷硫基、C1-C7-羟烷基、C2-C4-酰基、芳基、芳氧基，其中含有芳基的基团上的芳基部分可以带有一至三个下列基团：氰基、硝基、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基或C1-C4-卤代烷硫基；
和/或式III化合物
其中取代基X1至X5和R19至R22如下定义：
X1至X5相互独立地是氢、卤素、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、C1-C4-硫代烷氧基、C1-C4-磺酰基烷基、硝基、氨基、N-C1-C4-羧基氨基、N-C1-C4-烷基氨基；
R19是C1-C4-烷基、C2-C4-烯基、C2-C4-炔基、C1-C4-烷基-C3-C7-环烷基，其中这些基团可以带有选自卤素、氰基和C1-C4-烷氧基的取代基；
R20是苯基或具有至少一个选自N、O和S的杂原子的5-元或6-元饱和或不饱和杂环基团，其中所述环状基团可以具有一至三个选自下列的取代基：卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、C1-C4-烷氧基-C2-C4-烯基、C1-C4-烷氧基-C2-C4-炔基；
R21和R22相互独立地是氢、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、N-C1-C4-烷基氨基、C1-C4-卤代烷基或C1-C4-卤代烷氧基。
式I的酰胺化合物本身是已知的，并描述于文献中(EP-A 545099)。WO 97/08952描述了杀真菌混合物，除了式I化合物外，它还包含另一种组分喹螨醚。据述，它对葡萄孢菌(灰霉病)非常有效。
式II化合物本身是已知的，描述于例如US-A5240940中。除了式II化合物外还包含其它具有杀真菌活性化合物的杀真菌混合物也是已知的，并描述于O.Z.45483中。
式III化合物及其制备方法描述于WO-A 96/19442中。
本发明的目的是提供对有害真菌具有改进活性且降低活性成分施用总量的混合物(增效混合物)，目的在于使这些已知化合物施用量降低和改进其活性谱。
我们发现，此目的通过开头定义的混合物可得以实现。而且，我们发现，通过同时(即一起或分别)施用化合物I和化合物II和/或III，或当使用单独的化合物I或II至III时，依次施用化合物I和化合物II至III，可以更好地防治有害真菌。
本发明混合物具有增效作用，因此特别适合于防治有害真菌，特别是蔬菜、葡萄和禾谷类的白粉病真菌。
在本发明内容中，卤素是氟、氯、溴和碘，特别是氟、氯和溴。
术语“烷基”包括直链或支链烷基。优选的是直链或支链C1-C12-烷基，特别是C1-C6-烷基。烷基的实例是例如下列的烷基：甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1，1-二甲基乙基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1，2-二甲基丙基、1，1-二甲基丙基、2，2-二甲基丙基、1-乙基丙基、正已基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1，2-二甲基丁基、1，3-二甲基丁基、2，3-二甲基丁基、1，1-二甲基丁基、2，2-二甲基丁基、3，3-二甲基丁基、1，1，2-三甲基丙基、1，2，2-三甲基丙基、1-乙基丁基、2-乙基丁基、1-乙基-2-甲基丙基、正庚基、1-甲基己基、1-乙基戊基、2-乙基戊基、1-丙基丁基、辛基、癸基、十二烷基；
卤代烷基是如上定义的烷基，该烷基部分或全部被一个或多个卤原子，特别是氟或氯取代。优选的是，存在1至3个卤原子，且特别优选二氟甲基或三氟甲基。
上述关于烷基和卤代烷基的说明也同样分别适合于烷氧基、卤代烷氧基、烷硫基、卤代烷硫基、烷基亚磺酰基和烷基磺酰基中的烷基和卤代烷基。
烯基包括直链或支链烯基。优选的是直链或支链C3-C12-烯基，特别是C3-C6-烯基。烯基的实例是2-丙烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1，1-二甲基-2-丙烯基、1，2-二甲基-2-丙烯基、1-乙基-2-丙烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1，1-二甲基-2-丁烯基、1，1-二甲基-3-丁烯基、1，1-二甲基-2-丁烯基、1，2-二甲基-3-丁烯基、1，3-二甲基-2-丁烯基、1，3-二甲基-3-丁烯基、2，2-二甲基-3-丁烯基、2，3-二甲基-2-丁烯基、2，3-二甲基-3-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1，1，2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基和1-乙基-2-甲基-2-丙烯基，特别是2-丙烯基、2-丁烯基、3-甲基-2-丁烯基和3-甲基-2-戊烯基。
所述烯基可以部分或全部被一个或多个卤原子，特别是氟或氯卤代。所述烯基优选具有1至3个卤原子。
炔基包括直链或支链炔基。优选的是直链或支链C3-C12-炔基，特别是C3-C6-炔基。炔基的实例是2-丙炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1-甲基-2-丁炔基、1，1-二甲基-2-丙炔基、1-乙基-2-丙炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-4-戊炔基、4-甲基-2-戊炔基、1，2-二甲基-2-丁炔基、1，1-二甲基-3-丁炔基、1，2-二甲基-3-丁炔基、2，2-二甲基-3-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基和1-乙基-1-甲基-2-丙炔基。
上面关于烯基及其卤素取代基和炔基的说明也同样适合于烯氧基和炔氧基。
环烷基优选是C3-C6-环烷基，如环丙基、环丁基、环戊基或环己基。如果所述环烷基是取代的，则它优选具有1至3个C1-C4-烷基取代基。
环烯基优选是C4-C6-环烯基，如环丁烯基、环戊烯基或环己烯基。如果所述环烯基是取代的，它优选具有1至3个C1-C4-烷基取代基。
环烷基氧基优选是C5-C6-环烷基氧基，如环戊基氧基或环己基氧基。如果所述环烷基氧基是取代的，它优选具有1至3个C1-C4-烷基取代基。
环烯基氧基优选是C5-C6-环烯基氧基，如环戊烯基氧基或环己烯基氧基。如果所述环烯基氧基是取代的，它优选具有1至3个C1-C4-烷基取代基。
芳基优选是苯基。
如果A是苯基，它可以具有一、二或三个任何位置上的上述取代基。这些取代基优选相互独立地选自烷基、二氟甲基、三氟甲基和卤素，特别是氯、溴和碘。特别优选在2位上具有取代基的苯基。
如果A是5-元杂环，则它特别是呋喃基、噻唑基、吡唑基、咪唑基、噁唑基、噻吩基、三唑基或噻二唑基或其相应的二氢或四氢衍生物。优选噻唑基或吡唑基。
如果A是6-元杂环，则它特别是吡啶基或下式的基团：
其中X和Y基中的一个是O、S或NR23，其中R23是H或烷基，且X和Y基中的另一个是CH2、S、SO、SO2或NR23。虚线是指双键可以存在或不存在。
6-元芳香杂环特别优选吡啶基，特别是3-吡啶基，或下式的基团
其中X是CH2、S、SO或SO2。
上面提到的杂环基可以具有或不具有1、2或3个上面提到的取代基，而这些取代基优选相互独立地选自烷基、卤素、二氟甲基或三氟甲基。
A特别优选是下式的基团：
其中R3、R4、R6、R7、R8和R9相互独立地是氢、烷基，特别是甲基、卤素，尤其是氯、CHF2或CF3。
式I中的R1基优选是氢原子。
式I中的R2基优选是苯基。R2优选具有至少一个取代基，该取代基特别优选在2-位。所述取代基(或多个取代基)优选选自烷基、环烷基、环烯基、卤素或苯基。
R2基的取代基本身可以再被取代。所述的脂族或环脂族取代基可以部分或全部被卤代，特别是氟代或氯代。它们优选具有1、2或3个氟或氯原子。如果R2基的取代基是苯基，则此苯基可以优选被1至3个卤原子，特别是氯原子，和/或被优选选自烷基和烷氧基的基团取代。特别优选的是，所述苯基在对位上被卤原子取代，即，R2基的特别优选的取代基是对位卤素取代的苯基。所述的R2基还可以与饱和的5-元环稠合，而此环上的部分可以具有1至3个烷基取代基。
在此情况下，R2是例如2，3-二氢化茚基(indanyl)、苯并二氢噻吩基或苯并二氢呋喃基(oxaindanyl)。优选的是2，3-二氢化茚基和2-氧杂-2，3-二氢化茚基(2-oxaindanyl)，它们经4-位与氮原子连接。
根据优选的实施方案，本发明的组合物包含其中A是如下定义的式I化合物的酰胺化合物：
苯基、吡啶基、二氢吡喃基、二氢氧硫杂环己二烯基(dihydrooxathiynyl)、氧化二氢氧硫杂环己二烯基、二氧化二氢氧硫杂环己二烯基、呋喃基、噻唑基、吡唑基或噁唑基，其中这些基团可以具有1、2或3个相互独立地选自烷基、卤素、二氟甲基和三氟甲基的取代基。
根据另一优选的实施方案，A是下列基团之一：
吡啶-3-基，它可以在2-位上被或未被卤素、甲基、二氟甲基、三氟甲基、甲氧基、甲硫基、甲基亚磺酰基或甲基磺酰基取代；
苯基，它可以在2-位上被或未被甲基、三氟甲基、氯、溴或碘取代；
2-甲基-5，6-二氢吡喃-3-基；
2-甲基-5，6-二氢-1，4-氧硫杂环己二烯-3-基或其4-氧化物或4，4-二氧化物；
2-甲基呋喃-3-基，它可以在4-位和/或5-位上被或未被甲基取代；
噻唑-5-基，它可以在2-位和/或4-位上被或未被甲基、氯、二氟甲基或三氟甲基取代；
噻唑-4-基，它可以在2-位和/或5-位上被或未被甲基、氯、二氟甲基或三氟甲基取代；
1-甲基吡唑-4-基，它可以在3-位和/或5-位上被或未被甲基、氯、二氟甲基或三氟甲基取代；
噁唑-5-基，它可以在2-位和/或4-位上被或未被甲基或氯取代；
根据另一优选实施方案，本发明组合物包含这样的式I化合物的酰胺化合物，其中R2是可以被或未被1、2或3个上面提到的取代基取代的苯基。
根据再一优选实施方案，本发明组合物包含这样的式I化合物的酰胺化合物，其中R2是在2-位上具有一个下列取代基的苯基：
C3-C6-烷基、C5-C6-环烯基、C5-C6-环烷基氧基、环烯基氧基，而这些基团可以被1、2或3个C1-C4-烷基取代，
苯基，它被1至5个卤原子和/或1至3个相互独立地选自下列的基团取代：C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基和C1-C4-卤代烷硫基，
2，3-二氢化茚基或苯并二氢呋喃基，它可以被或未被1、2或3个C1-C4-烷基取代。
根据再一实施方案，本发明组合物包含作为酰胺化合物的式Ia化合物，
其中
A是
X 是亚甲基、硫、亚磺酰基或磺酰基(SO2)，
R3是甲基、二氟甲基、三氟甲基、氯、溴或碘，
R4是三氟甲基或氯，
R5是氢或甲基，
R6是甲基、二氟甲基、三氟甲基或氯，
R7是氢、甲基或氯，
R8是甲基、二氟甲基或三氟甲基，
R9是氢、甲基、二氟甲基、三氟甲基或氯，
R10是C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基或卤素。
根据本发明的特别优选的实施方案，本发明组合物包含作为酰胺化合物的式Ib化合物
其中
R4是卤素，且
R11是被卤素取代的苯基。
有用的式I酰胺化合物在EP-A-545099和589031中提到，上述二篇专利文献全文并入作为参考。
式I酰胺化合物的制备是已知的，例如描述在EP-A-545099或589031中的方法，或可以通过类似的方法制备。
特别优选的组分b)是下文表1中的式IIa化合物。
表1
| 序号 | R<sup>12</sup> | R<sup>13</sup> | R<sup>14</sup> | R<sup>15</sup> | R<sup>16</sup> |
| II.1 | H | H | Cl | H | 2-F |
| II.2 | H | H | Cl | H | 2-C(CH<sub>3</sub>)<sub>3</sub> |
| II.3 | H | H | Cl | H | 2-CH<sub>3</sub> |
| II.4 | H | H | Cl | H | 2-OCH<sub>3</sub> |
| II.5 | H | H | Cl | H | 3-F |
| II.6 | H | H | Cl | H | 3-Cl |
| II.7 | H | H | Cl | H | 3-CF<sub>3</sub> |
| II.8 | H | H | Cl | H | 3-CN |
| II.9 | H | H | Cl | H | 3-OCH<sub>3</sub> |
| II.10 | H | H | Cl | H | 3-苯基 |
| II.11 | H | H | Cl | H | 4-Cl |
| 序号 | R<sup>12</sup> | R<sup>13</sup> | R<sup>14</sup> | R<sup>15</sup> | R<sup>16</sup> |
| II.12 | H | H | Cl | H | 4-Br |
| II.13 | H | H | Cl | H | 4-CF<sub>3</sub> |
| II.14 | H | H | Cl | H | 4-CH<sub>3</sub> |
| II.15 | H | H | Cl | H | 4-CH(CH<sub>3</sub>)<sub>2</sub> |
| II.16 | H | H | Cl | H | 4-CN |
| II.17 | H | H | Cl | H | 2-Cl-4-F |
| II.18 | H | H | Cl | H | 2，4-二-Br |
| II.19 | H | H | Cl | H | 2，4-二-NO<sub>2</sub> |
| II.20 | H | H | Cl | H | 2-CH<sub>3</sub>-4-F |
| II.21 | H | H | Cl | H | 2，6-二-F |
| II.22 | H | H | Cl | H | 2，4，6-三-CH<sub>3</sub> |
| II.23 | F | H | H | H | 4-F |
| II.24 | Cl | H | H | H | 4-F |
| II.25 | NO<sub>2</sub> | H | H | H | 4-F |
| II.26 | H | F | H | H | 4-F |
| II.27 | H | Cl | H | H | 4-F |
| II.28 | H | CH<sub>3</sub> | H | H | 4-F |
| II.29 | H | NO<sub>2</sub> | H | H | 4-F |
| 序号 | R<sup>12</sup> | R<sup>13</sup> | R<sup>14</sup> | R<sup>15</sup> | R<sup>16</sup> |
| II.30 | H | OC<sub>2</sub>H<sub>5</sub> | H | H | 4-F |
| 序号 | R<sup>12</sup> | R<sup>13</sup> | R<sup>14</sup> | R<sup>15</sup> | R<sup>16</sup> |
| II.31 | H | H | F | H | 4-F |
| II.32 | H | H | Cl | H | 4-F |
| II.33 | H | H | Br | H | 4-F |
| II.34 | H | H | NO<sub>2</sub> | H | 4-F |
| II.35 | H | H | OCF<sub>3</sub> | H | 4-F |
| II.36 | H | H | C<sub>2</sub>H<sub>5</sub> | H | 4-F |
| II.37 | H | H | SCF<sub>3</sub> | H | 4-F |
| II.38 | H | H | O-C<sub>2</sub>H<sub>5</sub> | H | 4-F |
| II.39 | H | H | H | F | 4-F |
| II.40 | H | H | H | Cl | 4-F |
| II.41 | H | H | H | CF3 | 4-F |
| II.42 | F | H | F | H | 4-F |
| II.43 | O-CH<sub>3</sub> | H | O-CH<sub>3</sub> | H | 4-F |
| II.44 | Cl | F | H | H | 4-F |
| II.45 | Cl | Cl | H | H | 4-F |
| II.46 | Cl | CH<sub>3</sub> | H | H | 4-F |
| II.47 | H | Br | H | Cl | 4-F |
| II.48 | H | Cl | H | OH | 4-F |
| II.49 | H | O-CH<sub>3</sub> | H | NO<sub>2</sub> | 4-F |
| II.50 | H | F | Cl | H | 4-F |
| 序号 | R<sup>12</sup> | R<sup>13</sup> | R<sup>14</sup> | R<sup>15</sup> | R<sup>16</sup> |
| II.51 | H | CH<sub>3</sub> | Cl | H | 4-F |
| II.52 | H | H | Cl | Cl | 4-F |
| II.53 | Cl | H | H | Cl | 4-F |
| II.54 | Cl | F | Cl | H | 4-F |
| II.55 | H | H | Cl | CN | 4-F |
| II.56 | Cl | CH<sub>3</sub> | Cl | H | 4-F |
| II.57 | Cl | Cl | Cl | H | 4-F |
| II.58 | Cl | Cl | Cl | Cl | 4-F |
| II.59 | H | H | H | Cl | 2-F-4-Br |
| II.60 | H | H | H | Cl | 2，3-二-CH<sub>3</sub> |
| II.61 | H | H | H | Cl | 2-F-4-Cl |
| II.62 | H | H | H | Cl | 2，4-二-Cl-6-F |
| II.63 | H | H | H | Cl | 2，4-二-F |
| II.64 | H | H | H | Cl | 2，4-二-CH<sub>3</sub> |
| II.65 | H | H | H | Cl | 2-C<sub>2</sub>H<sub>5</sub> |
| II.66 | H | H | H | Cl | 2-CH<sub>3</sub>-4-F |
| II.67 | H | H | H | Cl | 3-CH<sub>3</sub>-4-Cl |
| II.68 | H | H | Cl | H | H |
| 序号 | R<sup>12</sup> | R<sup>13</sup> | R<sup>14</sup> | R<sup>15</sup> | R<sup>16</sup> |
| II.69 | Cl | H | Cl | H | H |
| 序号 | R<sup>12</sup> | R<sup>13</sup> | R<sup>14</sup> | R<sup>15</sup> | R<sup>16</sup> |
| II.70 | H | H | Cl | H | 4-C(CH<sub>3</sub>)<sub>3</sub> |
更特别优选的是表2的式IIa化合物以及其中提到的化合物2.78的盐酸盐和其N-氧化物。
表2
| 序号 | R<sup>12</sup> | R<sup>13</sup> | R<sup>14</sup> | R<sup>15</sup> | R<sup>16</sup> |
| II.71 | H | H | Cl | H | 2-Cl |
| II.72 | H | H | Cl | H | 2-Br |
| II.73 | H | H | Cl | H | 2-CN |
| II.74 | H | H | Cl | H | 2-CF<sub>3</sub> |
| II.75 | H | H | Cl | H | 2-NO<sub>2</sub> |
| II.76 | H | H | Cl | H | 4-F |
| II.77 | H | H | Cl | H | 2，4-二-F |
| II.78 | Cl | H | Cl | H | 4-F |
| II.79 | H | H | H | Cl | 2-Cl-4-F |
| II.80 | CH<sub>3</sub> | H | CH<sub>3</sub> | H | 4-F |
在表1和2中或与其相关联提到的式IIa化合物由US-A 5240940和/或ACS Sympos.Ser.443，第538至第552页(1991)可知。
在式III化合物中，优选的是这样的化合物，其中X1是C1-C4-卤代烷基，特别是三氟甲基，和X2与X3为氢原子或卤素，特别是氢原子。X4和X5优选是氢、卤素(特别是Cl和F)、C1-C4-烷氧基(特别是甲氧基或乙氧基)、C1-C4-烷硫基(特别是甲硫基或乙硫基)、C1-C4-卤代烷基(特别是三氟甲基)或C1-C4-卤代烷氧基(特别是三氟甲氧基)。
优选的取代基R19是C1-C4-烷基(甲基、乙基、正丙基和异丙基以及叔丁基)、C1-C4-亚烷基-C3-C7-环烷基、C1-C4-烯基(特别是乙烯基、丙烯基和丁烯基，它可以被取代、特别是被卤素(优选氯)取代)、丙炔基、氰基甲基和甲氧基甲基。在C1-C4-亚烷基-C3-C7-环烷基取代基中，特别优选亚甲基-取代的化合物，特别是亚甲基环丙基、亚甲基环戊基、亚甲基环己基和亚甲基环己烯基。这些取代基上的环可以被取代、优选被卤素取代。
取代基R20除可以提到苯基外，还特别优选是(取代或未取代的)噻吩基、吡唑基、吡咯基、咪唑基、噻唑基、呋喃基、哒嗪基和嘧啶基。在这些环系上的优选的取代基是卤素(特别是氟和氯)、C1-C4-烷氧基(特别是甲氧基)和C1-C4-烷基(特别是甲基、乙基)。环取代基的数量可以是1至3，特别是1至2。特别优选的是苯基或取代的苯基。
优选的取代基R21和R22是氢、氟、氯、甲基、乙基、甲氧基、硫基甲基和N-甲基氨基。R3和R4一起还可以形成基团＝O。
优选的式III化合物示于业已提到的WO 96/019442的表格中。这些化合物中，特别优选的是列于下文表3中的化合物(R21和R22各是氢)。
表3
| 序号 | X<sup>1</sup> | X<sup>2</sup> | X<sup>3</sup> | X<sup>4</sup> | X<sup>5</sup> | R<sup>19</sup> | R<sup>20</sup> |
| III.1 | CF<sub>3</sub> | H | H | H | H | 乙基 | Ph-4-OMe |
| III.2 | CF<sub>3</sub> | H | H | H | H | 甲基 | Ph-4-OMe |
| III.3 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-cPr | 2-噻吩基 |
| III.4 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-cPr | 3-噻吩基 |
| III.5 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-cPr | Ph-2，4-F2 |
| III.6 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-cPr | Ph-2-F |
| III.7 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-cPr | Ph-2-F-4-OMe |
| III.8 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-cPr | Ph-3-Me |
| III.9 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-cPr | Ph-3-Me-4-OMe |
| III.10 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-cPr | Ph-4-F |
| III.1l | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-cPr | Ph-4-Me |
| III.12 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-cPr | Ph-4-OMe |
| III.13 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-cPr | Ph |
| III.14 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-CH＝CH<sub>2</sub> | Ph |
| 序号 | X<sup>1</sup> | X<sup>2</sup> | X<sup>3</sup> | X<sup>4</sup> | X<sup>5</sup> | R<sup>19</sup> | R<sup>20</sup> |
| 序号 | X<sup>1</sup> | X<sup>2</sup> | X<sup>3</sup> | X<sup>4</sup> | X<sup>5</sup> | R<sup>19</sup> | R<sup>20</sup> |
| III.15 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-CH＝CH<sub>2</sub> | Ph-4-oMe |
| III.16 | CF<sub>3</sub> | H | H | H | H | -CH<sub>2</sub>-CH＝CCl<sub>2</sub> | Ph-4-OMe |
| III.17 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-CH<sub>3</sub> | Ph-4-OMe |
| III.18 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>CH<sub>3</sub> | Ph |
| III.19 | CF<sub>3</sub> | H | H | H | F | -CH<sub>3</sub> | Ph-4-OMe |
| III.20 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-cPr | Ph |
| III.21 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-cPr | Ph-2-F |
| III.22 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-cPr | Ph-2，4-F<sub>2</sub> |
| III.23 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-cPr | Ph-2-F-3-Me |
| III.24 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-cPr | Ph-2-F-4-OMe |
| III.25 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-cPr | Ph-3，5-Me<sub>2</sub> |
| III.26 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-cPr | 3-甲基吡唑-1-基 |
| III.27 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-cPr | 3-甲基-2-噻吩基 |
| III.28 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-cPr | 2-噻吩基 |
| III.29 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-cPr | 3-噻吩基 |
| III.30 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-CHF<sub>2</sub> | Ph-4-OMe |
| III.31 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-OCH<sub>3</sub> | Ph-4-OMe |
| III.32 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-OCH<sub>3</sub> | Ph |
| 序号 | X<sup>1</sup> | X<sup>2</sup> | X<sup>3</sup> | X<sup>4</sup> | X<sup>5</sup> | R<sup>19</sup> | R<sup>20</sup> |
| III.33 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>CN | Ph-4-Ome |
| III.34 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>CN | Ph |
| III.35 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-C≡CH | Ph |
| III.36 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-C≡CH | Ph-4-OMe |
| III.37 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-C≡CH | Ph-2-F |
| III.38 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-C≡CH | Ph-4-Me |
| III.39 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-C≡CH | 2-噻吩基 |
| III.40 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-C≡CH | Ph-2-F-4-OMe |
| III.41 | CF<sub>3</sub> | H | H | H | F | 异丙基 | Ph |
| III.42 | CF<sub>3</sub> | H | H | H | F | 正丁基 | Ph |
| III.43 | CF<sub>3</sub> | H | H | H | F | 正丙基 | Ph |
| III.44 | CF<sub>3</sub> | H | H | H | F | 叔丁基 | Ph |
| III.45 | CF<sub>3</sub> | H | H | H | Cl | -CH<sub>3</sub> | |
| III.46 | CF<sub>3</sub> | H | H | H | Cl | -CH<sub>2</sub>CN | Ph-4-OMe |
| III.47 | CF<sub>3</sub> | H | H | H | Cl | -CH<sub>2</sub>-OMe | Ph-4-OMe |
| III.48 | CF<sub>3</sub> | H | H | H | Cl | -CH<sub>2</sub>-cPr | Ph |
| III.49 | CF<sub>3</sub> | H | H | H | Cl | -CH<sub>2</sub>-cPr | 3-甲基吡唑-1-基 |
| III.50 | CF<sub>3</sub> | H | H | H | Cl | -CH<sub>2</sub>-cPr | 2-噻吩基 |
| 序号 | X<sup>1</sup> | X<sup>2</sup> | X<sup>3</sup> | X<sup>4</sup> | X<sup>5</sup> | R<sup>19</sup> | R<sup>20</sup> |
| III.51 | CF<sub>3</sub> | H | H | H | Cl | -CH<sub>2</sub>-cPr | Ph-2，4-F<sub>2</sub> |
| 序号 | X<sup>1</sup> | X<sup>2</sup> | X<sup>3</sup> | X<sup>4</sup> | X<sup>5</sup> | R<sup>19</sup> | R<sup>20</sup> |
| III.52 | CF<sub>3</sub> | H | H | H | Cl | -CH<sub>2</sub>-C≡CH | Ph-4-OMe |
| III.53 | CF<sub>3</sub> | H | H | H | CF<sub>3</sub> | -CH<sub>3</sub> | Ph-4-OMe |
| III.54 | CF<sub>3</sub> | H | H | H | CF<sub>3</sub> | -CH<sub>2</sub>CH<sub>2</sub>Cl | Ph-4-OMe |
| III.55 | CF<sub>3</sub> | H | H | H | CF<sub>3</sub> | -CH<sub>2</sub>-cPr | 2-噻吩基 |
| III.56 | CF<sub>3</sub> | H | H | H | CF<sub>3</sub> | -CH<sub>2</sub>-cPr | Ph-2-F-5-Me |
| III.57 | CF<sub>3</sub> | H | H | H | CF<sub>3</sub> | -CH<sub>2</sub>-cPr | Ph-4-OMe |
| III.58 | CF<sub>3</sub> | H | H | H | CF<sub>3</sub> | -CH<sub>2</sub>-cPr | Ph |
| III.59 | CF<sub>3</sub> | H | H | H | OCH<sub>3</sub> | -CH<sub>2</sub>CH<sub>3</sub> | Ph-4-OMe |
| III.60 | CF<sub>3</sub> | H | H | H | OCH<sub>3</sub> | -CH<sub>2</sub>-cPr | Ph-4-OMe |
| III.61 | CF<sub>3</sub> | H | H | H | OCH<sub>3</sub> | -CH<sub>2</sub>-cPr | Ph |
| III.62 | CF<sub>3</sub> | H | H | H | SCH<sub>3</sub> | -CH<sub>2</sub>-cPr | Ph |
| III.63 | CF<sub>3</sub> | H | H | H | SCH<sub>3</sub> | -CH<sub>2</sub>-cPr | Ph-4-Ome |
| III.64 | CF<sub>3</sub> | H | H | Cl | F | -CH<sub>2</sub>-CH<sub>2</sub>Cl | Ph |
| III.65 | CF<sub>3</sub> | H | H | Cl | F | -CH<sub>2</sub>-CH＝CH<sub>2</sub> | Ph-4-OMe |
| III.66 | CF<sub>3</sub> | H | H | Cl | F | -CH<sub>2</sub>-cPr | 2-噻吩基 |
| III.67 | CF<sub>3</sub> | H | H | Cl | F | -CH<sub>2</sub>-cPr | Ph-2-F |
| III.68 | CF<sub>3</sub> | H | H | Cl | F | -CH<sub>2</sub>-cPr | Ph |
| III.69 | CF<sub>3</sub> | H | H | Cl | F | -CH<sub>2</sub>-cPr | Ph-2-F-5-Me |
| 序号 | X<sup>1</sup> | X<sup>2</sup> | X<sup>3</sup> | X<sup>4</sup> | X<sup>5</sup> | R<sup>19</sup> | R<sup>20</sup> |
| III.70 | CF<sub>3</sub> | H | H | Cl | Cl | -CH<sub>2</sub>-CH＝CH<sub>2</sub> | Ph-4-OMe |
| III.71 | CF<sub>3</sub> | H | H | Cl | Cl | -CH<sub>2</sub>CH<sub>2</sub>Cl | Ph |
| III.72 | CF<sub>3</sub> | H | H | Cl | Cl | -CH<sub>2</sub>CH<sub>3</sub> | Ph-2-F-5-Me |
| III.73 | CF<sub>3</sub> | H | H | Cl | Cl | -CH<sub>2</sub>-cPr | Ph-3，5-Me2 |
| III.74 | CF<sub>3</sub> | H | H | SCH<sub>3</sub> | F | -CH<sub>2</sub>-cPr | Ph-4-OMe |
| III.75 | CF<sub>3</sub> | H | H | OCH<sub>3</sub> | F | -CH<sub>2</sub>-cPr | Ph-4-OMe |
| III.76 | CF<sub>3</sub> | H | F | H | H | -CH<sub>2</sub>-cPr | Ph |
| III.77 | CF<sub>3</sub> | H | F | H | H | -CH<sub>2</sub>-CH<sub>3</sub> | Ph-4-OMe |
| III.78 | CF<sub>3</sub> | H | H | F | F | -CH<sub>2</sub>CH<sub>3</sub> | Ph |
| III.79 | CF<sub>3</sub> | H | H | F | F | -CH<sub>2</sub>-CH<sub>2</sub>Cl | Ph-2-F-5-Me |
| III.80 | CF<sub>3</sub> | H | H | F | F | -CH<sub>2</sub>-OCH<sub>3</sub> | Ph-4-OMe |
| III.81 | CF<sub>3</sub> | H | H | F | F | -CH<sub>2</sub>-cPr | Ph |
| III.82 | CF<sub>3</sub> | H | H | F | F | -CH<sub>2</sub>-cPr | 3-甲基吡唑-1-基 |
| III.83 | CF<sub>3</sub> | H | H | F | F | -CH<sub>2</sub>-cPr | 3-甲基-2-噻吩基 |
| III.84 | CF<sub>3</sub> | H | H | F | F | -CH<sub>2</sub>-cPr | Ph-2-F-3-Me |
| III.85 | CF<sub>3</sub> | H | H | F | F | -CH<sub>2</sub>-cPr | Ph-2-F-4-OMe |
| III.86 | CF<sub>3</sub> | H | H | F | F | -CH<sub>2</sub>-cPr | Ph-2-F-5-Me |
| III.87 | CF<sub>3</sub> | H | H | F | F | -CH<sub>2</sub>-cPr | Ph-4-OMe |
| III.88 | CF<sub>3</sub> | H | H | F | F | -CH<sub>2</sub>-cPr | Ph-4F |
| 序号 | X<sup>1</sup> | X<sup>2</sup> | X<sup>3</sup> | X<sup>4</sup> | X<sup>5</sup> | R<sup>19</sup> | R<sup>20</sup> |
| III.89 | CF<sub>3</sub> | H | H | F | F | 异丙基 | Ph-4-OMe |
| 序号 | X<sup>1</sup> | X<sup>2</sup> | X<sup>3</sup> | X<sup>4</sup> | X<sup>5</sup> | R<sup>19</sup> | R<sup>20</sup> |
| III.90 | CF<sub>3</sub> | H | H | F | F | 正丁基 | Ph-4-OMe |
| III.91 | CF<sub>3</sub> | H | H | F | F | -CH<sub>2</sub>-C≡CH | Ph-4-OMe |
| III.92 | CF<sub>3</sub> | H | H | CF<sub>3</sub> | F | -CH<sub>3</sub> | Ph-4-OMe |
| III.93 | CF<sub>3</sub> | H | H | CF<sub>3</sub> | F | -CH<sub>2</sub>-CH＝CH<sub>2</sub> | Ph |
| III.94 | CF<sub>3</sub> | H | H | CF<sub>3</sub> | F | -CH<sub>2</sub>-cPr | Ph |
| III.95 | CF<sub>3</sub> | H | H | Cl | Cl | -CH<sub>2</sub>-CHxe-3 | Ph |
| III.96 | CF<sub>3</sub> | H | H | F | H | -CH<sub>2</sub>-cPr | Ph-4-F |
| III.97 | CF<sub>3</sub> | H | H | Cl | Cl | -CH<sub>2</sub>-cHex | Ph |
| III.98 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-SCH<sub>3</sub> | Ph |
| III.99 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-SOCH<sub>3</sub> | Ph |
| III.100 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-SO<sub>2</sub>CH<sub>3</sub> | Ph |
| III.101 | CF<sub>3</sub> | H | H | H | F | -CH<sub>2</sub>-NHMe | Ph |
| III.102 | CF<sub>3</sub> | H | H | H | F | CH<sub>2</sub>-CONH<sub>2</sub> | Ph |
| III.103 | CF<sub>3</sub> | H | H | H | F | CH<sub>2</sub>CON(CH<sub>3</sub>)<sub>2</sub> | Ph |
在上述表格中，cPr是环丙基、cHxe-n是在n位上未饱和的环己烯基、c-Hex是环己基且Ph表示苯基。
特别优选的是这样的化合物III，其中R19是基团CH2-cPr且R20是有或无取代基的苯基。它们之中，优选的是其中X4和X5为卤素(优选是F)的化合物。
这些化合物的物理数据及其制备方法公开在业已提到的WO96/19442中。
对于呈现增效活性而言，甚至是少量的式I酰胺化合物就足够。酰胺化合物与式II和/或III活性成分的重量比优选为50∶1至1∶50，特别是10∶1至1∶10。在此，还可以是三元混合物，它除酰胺化合物I外，包含化合物II和化合物III。在这种混合物中，化合物II和III相互间的混合比通常是在50∶1至1∶50、优选10∶1至1∶10之间。
由于其氮原子的碱性特点，化合物II可与无机或有机酸或与金属离子形成盐或加合物。
无机酸的实例是氢卤酸如氢氟酸、盐酸、氢溴酸和氢碘酸，硫酸、磷酸和硝酸。
适合的有机酸是例如甲酸、碳酸和链烷酸如乙酸、三氟乙酸、三氯乙酸和丙酸，以及乙醇酸、硫氰酸、乳酸、琥珀酸、柠檬酸、苯甲酸、肉桂酸、草酸、烷基磺酸(具有1至20个碳原子的直链或支链烷基的磺酸)、芳基磺酸或芳基二磺酸(芳基，如苯基和萘基，它们连有一或二个磺基)、烷基膦酸(具有1至20个碳原子的直链或支链烷基的膦酸)、芳基膦酸或芳基二膦酸(芳基，如苯基和萘基，它们连有一或二个膦酸基)，对于所述的烷基或芳基而言，也可连有另外的取代基，例如对甲苯磺酸、水杨酸、对氨基水杨酸、2-苯氧基苯甲酸、2-乙酰氧基苯甲酸等。
适合的金属离子特别是第二主族元素，特别是钙和镁，第三和第四主族元素，特别是铝、锡和铅，和第1至八副族元素的离子，特别是铬、锰、铁、钴、镍、铜、锌及其它。这些金属可以以各种它们可以假定的化合价存在。
当制备混合物时，优选的是采用纯的活性成分，并且如果需要的话，它们可以与其它的防治有害真菌或其它害虫如昆虫、蜱螨或线虫的活性成分，或是与除草的或生长调节的活性成分或化肥混合。
化合物I和II和/或III的混合物，或同时、结合或分别使用的化合物I和II和/或III，对广谱的植物病原真菌，特别是对子囊菌纲、担子菌纲、藻菌纲和半知菌纲有突出的作用。它们中的一些有内吸作用，因此可以采用来作为叶面和土壤作用的杀真菌剂。
它们在防治各种作物如棉花、蔬菜(例如，黄瓜、豆类、蕃茄、马铃薯和胡芦)、大麦、禾草、燕麦、香蕉、咖啡、玉米、水果、稻、黑麦、大豆、葡萄、小麦、观赏植物、甘蔗和各种种子上的许多植物病原真菌方面特别重要。
它们特别适合于防治下列植物病原真菌：禾谷类上的禾白粉菌(Erysiphe graminis)、胡芦上的二孢白粉菌(Erysiphe cichoracearum)和苍耳单丝壳菌(Sphaerotheca fuliginea)、苹果上的苹果白粉病白叉丝单囊壳菌(Podosphaera leucotricha)、葡萄上的葡萄白粉病钩丝壳霉(Uncinula necator)、禾谷类上的柄锈菌(Puccinia)、棉花、稻和草坪上的丝核菌(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(Septorianodorum)、草莓、蔬菜、观赏植物和葡萄上的灰霉菌(Botrytiscinera)、花生上的花生尾孢菌(Cercospora arachidicola)、小麦和大麦上的眼斑病菌(Pseudocercosporella herpotrichoides)、稻上的稻梨孢(Pyricularia oryzae)、马铃薯和蕃茄上的蔓延疫霉(Phytophthora infestans)、葡萄上的葡萄生单轴霉(Plasmoparaviticola)、忽布和黄瓜上的假霜霉(Pseudoperonospora)、蔬菜和水果上的链格孢菌(Alternaria)、香蕉上的球腔菌(Mycosphaerella)以及镰刀菌(Fusarium)和轮枝孢菌(Verticillium)。
本发明混合物特别适合于采用来防治葡萄和蔬菜作物以及观赏植物和禾谷类上的白粉病真菌。
化合物I和II和/或III可以同时，或者一起或分别，或依次施用，在分别施用时，施用顺序通常不影响防治措施的效果。
依据所需效果种类的不同，本发明混合物的施用量以农作物面积计通常为0.01至8千克/公顷，优选0.1至5千克/公顷，特别是0.2至3.0千克/公顷。
化合物I的施用量一般是0.01至2.5千克/公顷，优选是0.05至2.5千克/公顷，特别是0.1至1.0千克/公顷。
相应地，在化合物II和/或III的情况下，其施用量这0.001至5千克/公顷，优选0.005至2千克/公顷，特别是0.01至1.0千克/公顷。
处理种子时，本发明混合物的施用量通常是0.001至250克/千克种子，优选0.01至100克/千克种子，特别是0.01至50克/千克种子。
如果意欲防治的是有害的植物病原真菌，则通过向种子、植物或播种前或后或植物出芽前或后的土壤喷雾或喷粉，分别或一起施用化合物I和化合物II和/或III或化合物I和II和/或III的混合物。
本发明的增效杀真菌混合物或化合物I和II和/或III可以加工成例如可直接喷雾溶液、粉剂和悬浮液形式，或高浓度水悬剂、油悬剂或其它悬浮剂、分散液、乳液、油分散液、膏剂、粉剂、撒施剂或颗粒剂，并可通过喷雾、弥雾、喷粉、撒施或浇泼使用。施用形式取决于使用的目的；在每一种情况下，应确保本发明混合物的分散尽可能地细微和均匀。
制剂可按照已知的方式来生产，例如，通过将活性成分用溶剂和/或载体填充，如果需要使用乳化剂和分散剂，如果水作为稀释剂，也可以使用其它有机溶剂作为助溶剂。适合于此目的的辅助剂主要是：溶剂如芳族化合物(例如，二甲苯)、氯代芳族化合物(例如氯苯类)、石蜡(例如矿物油馏份)、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；载体如粉碎的天然矿物质(例如高岭土、陶土、滑石、白垩)和研碎的合成矿物质(例如细粉状二氧化硅、硅酸盐)；乳化剂如非离子型和阴离子型乳化剂(例如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)和分散剂如木素亚硫酸盐废液和甲基纤维素。
合适的表面活性剂是芳族磺酸例如木素磺酸、苯酚磺酸、萘磺酸和二丁基萘磺酸的碱金属、碱土金属盐，和脂肪酸、烷基磺酸和烷基芳基磺酸、烷基硫酸、月桂基醚硫酸和脂肪醇硫酸的碱金属、碱土金属盐，以及磺化的十六-、十七-和十八醇或脂肪醇醚的盐，磺化的萘和其与甲醛的衍生物的缩合产物，萘或萘磺酸与苯酚和甲醛的缩合产物，聚氧乙烯辛基酚醚、乙氧基烷化的异辛基-、辛基-或壬基酚、烷基苯酚或三丁基苯基聚乙二醇醚，烷基芳基聚醚醇、异十三烷基醇、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醚，月桂醇聚乙二醇醚乙酸酯、山梨糖醇酯，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化合物I或II和/或III或化合物I和II和/或III的混合物与固体载体混合或一起研磨而制备。
颗粒剂(例如，涂敷、浸渍或均质颗粒剂)通常是通过将一种或多种活性化合物粘合到固体载体上而制备。
可以使用的填料和固体载体的实例是矿石土如硅胶、二氧化硅、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、硫酸镁、氧化镁、研磨的合成材料，和化肥如硫酸铵、磷酸铵、硝酸铵、尿素和植物源产物如面粉、树皮粉、木粉和坚果壳粉、纤维素粉和其它固体载体。
制剂中通常含有0.1至95％(重量)，优选0.5至90％(重量)的化合物I或II和/或III之一、或化合物I和II和/或III的混合物。采用的活性成分纯度为90％至100％，优选95％至100％(根据NMR或HPLC)。
化合物I和II和/或III或混合物或相应的制剂，是通过使用杀真菌有效量的混合物或(在分别施用的情况下)化合物I和II和/或III，处理真菌、其栖生地或处理意欲防除有害真菌的植物、种子、土壤、表面、材料或空间来施用的。
该使用可以在有害真菌侵染前或侵染后进行。
这些包含活性成分的制剂的实例是：
I.90重量份的活性成分与10重量份的N-甲基吡咯烷酮的溶液；此溶液适合以微滴的形式使用；
II.20重量份的活性成分、80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-单乙醇酰胺的加合物、5重量份的十二烷基苯磺酸钙、5重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加合物的混合物；通过将此溶液均匀分散于水中，获得一种分散液；
III.20重量份的活性成分、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摩尔蓖麻油的加合物的水分散液；
IV.20重量份的活性成分、25重量份的环己醇、65重量份的沸点为210至280℃的矿物油馏份和10重量份40摩尔环氧乙烷与1摩尔蓖麻油的加合物的水分散液；
V.80重量份的活性成分、3重量份的二异丁基萘-1-磺酸的钠盐、10重量份的来源于亚硫酸废液的木素磺酸的钠盐和7重量份的粉状硅胶在锤磨中研磨的混合物；将此混合物均匀分散于水中，获得喷雾混合物；
VI.3重量份的活性成分和97重量份的高岭土微粉的紧密混合物；此粉剂包含按重量计3％的活性成分；
VII.30重量份的活性成分、92重量份的粉状硅胶和8重量份的事先喷雾到此硅胶上的石蜡油的紧密混合物；此剂型赋予活性成分良好的粘附性。
VIII.40重量份的活性成分、10重量份的苯酚磺酸/尿素/甲醛缩合物的钠盐、2重量份的硅胶和48重量份的水的稳定的水分散液；此分散液可以进一步稀释；
IX.20重量份的活性成分、2重量份的十二烷基苯磺酸的钙盐、8重量份的脂肪醇聚乙二醇醚、20重量份的苯酚磺酸/尿素/甲醛缩合物的钠盐和88重量份石蜡性矿物油的稳定的油分散液。
应用实施例
本发明混合物的增效活性可以通过下列实验来证实：
在如下混合物中将活性成分分别或一起加工成浓度为10％的乳剂：按重量计63％的环己酮和按重量计27％(重量)的乳化剂的混合物，并用水稀释至所需浓度。
通过确定感病的叶面积百分率进行评价，并将这些百分率值转化成效力。效力(W)使用Abbot公式计算
W＝(1-α)·100/β
α处理植物的真菌感染(％)
β未处理(对照)植物的真菌感染(％)
效力为0，指感染程度与未处理对照相当；效力为100，指处理的植物未感染。
活性成分混合物的预期效力通过Colby公式来计算[R.S.Colby，《杂草》[Weeds]15，20-22(1967)]，并与实测效力作比较。
Colby公式：
E＝x+y-x·y/100
E 以浓度a与b使用活性成分A和B的混合物时的预期药效值，以相对于未处理的百分比表示
x 以浓度a使用活性成分A时的效力，以相对于未处理的百分比表示
y 以浓度b使用活性成分B时的效力，以相对于未处理的百分比表示。
对小麦白粉病的活性
栽培品种为”Fruhgold”的盆栽小麦苗的叶片用由10％活性成分、63％环己酮和27％乳化剂组成的母液制备出的活性成分的含水制剂喷雾直到雾滴向下滴流。喷雾液层干燥后24小时，将叶片用小麦白粉病菌(Erysiphe graminis forma specialis tritici)孢子喷粉。试验植株随后放置在20-24℃和60-90％相对湿度的温室中。7天后目测确定总叶片面积上的真菌感染(％)。
所用的式I化合物为下列组分：
结果示于下面的表4和5中。
表4
| 实施例 | 活性成分 | 喷雾液中的活性成分浓度(ppm) | 相对于未处理对照的效力(％) |
| 1C | 对照(未处理) | 0(感染率98％) | 0 |
| 2C | I.1 | 6316 | 00 |
| 实施例 | 活性成分 | 喷雾液中的活性成分浓度(ppm) | 相对于未处理对照的效力(％) |
| 3C | I.2 | 6316 | 00 |
| 4C | 表2中的化合物II.78 | 10.25 | 00 |
| 5C | 表3中的化合物III.17 | 0.25 | 85 |
表5
| 实施例 | 本发明混合物(浓度以ppm计) | 观察到的效力 | 计算出的效力*) |
| 6 | 63ppm I.1+1ppm II.78 | 29 | 0 |
| 7 | 63ppm I.2+1ppm II.78 | 59 | 0 |
| 8 | 16ppm I.2+0.25ppm II.78 | 19 | 0 |
| 9 | 16ppm I.1+0.25ppm III.17 | 97 | 85 |
| 10 | 16ppm I.2+0.25ppm III.17 | 100 | 85 |
*)用Colby公式计算
试验结果显示，观察效力超过用Colby公式计算得到的效力。
Claims (5)
1.一种杀真菌混合物，包含活性组分
a)式Ib的酰胺化合物
其中
R4是卤素以及
R11是被卤素取代的苯基，
和
c)式III化合物
其中取代基X1至X5和R19至R22如下所定义：
X1是三氟甲基；
X2、X3是氢；
X4、X5是氢、氟或氯；
R19是C1-C4-烷基或基团CH2-cPr，其中cPr是环丙基；
R20是苯基，其中苯基可以具有一个选自卤素、C1-C4-烷基、C1-C4-烷氧基的取代基；
R21和R22是氢，
其中式Ib的酰胺化合物与式III化合物的重量比为1∶50至50∶1。
2.权利要求1的杀真菌混合物，它包含作为酰胺化合物Ib的下式化合物I.1或化合物I.2：
3.根据前述权利要求任一项的杀真菌混合物，它由二个部分组成，一部分包括在固体载体或溶剂中的酰胺化合物Ib，以及另一部分包括在固体载体或溶剂中的化合物III。
4.一种防治有害真菌的方法，该方法包括用根据权利要求1至3任一项的杀真菌混合物处理真菌、其栖生地，其中所述活性成分酰胺化合物Ib和化合物III的施用可以同时即一起或分别进行，或依次进行。
5.一种防治有害真菌的方法，该方法包括用根据权利要求1至3任一项的杀真菌混合物处理意欲防除有害真菌的材料、植物、种子、土壤、表面或空间，其中所述活性成分酰胺化合物Ib和化合物III的施用可以同时即一起或分别进行，或依次进行。
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| DE256503T1 (de) | 1986-08-12 | 1990-02-08 | Mitsubishi Kasei Corp., Tokio/Tokyo | Pyridincarboxamid-derivate und ihre verwendung als fungizides mittel. |
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