CN1196657A - 用抑制细胞色素复合体ⅲ的呼吸作用的活性物质与酰胺的组合物控制有害真菌 - Google Patents
用抑制细胞色素复合体ⅲ的呼吸作用的活性物质与酰胺的组合物控制有害真菌 Download PDFInfo
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- CN1196657A CN1196657A CN96197104A CN96197104A CN1196657A CN 1196657 A CN1196657 A CN 1196657A CN 96197104 A CN96197104 A CN 96197104A CN 96197104 A CN96197104 A CN 96197104A CN 1196657 A CN1196657 A CN 1196657A
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- Prior art keywords
- alkyl
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- phenyl
- unsubstituted
- halogen atom
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- 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
- A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A—HUMAN NECESSITIES
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- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- 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
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Abstract
本发明涉及控制有害真菌的组合物,该组合物含有作为活性成分的至少一种抑制细胞色素复合体Ⅲ上呼吸作用的化合物和至少一种式Ⅱ酰胺化合物A-CO-NR1-R2其中A,R1和R2具有说明书中给出的定义。本发明组合物可以特别地用来控制葡萄孢属真菌。
Description
本发明涉及控制有害真菌的由抑制细胞色素复合体III的呼吸作用的活性物质与酰胺形成的组合物,并涉及应用这些组合物控制有害真菌的方法。
从文献中知道,抑制细胞色素bc1复合体(细胞色素复合体III)的活性成分可以用作杀真菌剂[参见U.Brandt,U.Haase,H.Schagger,G.von Jagow:“strobilurins的特异性和作用机理”专题论文129卷,27-38,VCH出版公司,魏海姆,1993;J.M.Clough:天然产物报道,1993,565-574;F.Rohl,H.Sauter:生物化学协会会报22,635(1993)]。
但是,当使用这些活性成分时,它们表现出的作用只是暂时的,即只是在短时间之后就会发现新的真菌生长。
EP-A-545099公开了下式酰苯胺化合物其中A是在2位被甲基,三氟甲基,氯,溴或碘取代的苯基,或者是未取代的或被甲基,氯,三氟甲基取代的芳香族或非芳香族杂环残基,R是未取代的或被卤原子取代的脂族或环脂族残基,或者是未取代的或被C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基或卤原子取代的苯基。这些化合物可以用来控制葡萄孢属真菌。
EP-A-589301公开了相同结构式的酰苯胺化合物,其中A是下式环状残基:其中R1是氢或C1-C4-烷基;R2是卤原子或C1-C4-烷基;R3是C1-C4-烷基或C1-C4-卤代烷基;n是1或2;R基本上具有上面给定的定义。这些化合物也可以用来控制葡萄孢属真菌。WO93/11117公开了下式化合物其中Q是C1-C3-烷基,C2-C3-链烯基,C2-C3-炔基,-(CH2)mCH=或-(CH2)m-X-(CH2)m;n是0或1;各m各自独立地是0,1,2,或3;各X各自独立地是O或S;R1是氢,氟化的甲基,甲基,乙基,C2-C6-链烯基,C3-C6-氯代烷基,苯基,烷基
硫代烷基,烷氧基烷基,卤代烷基硫代烷基,卤代烷氧基烷基,或羟基烷基;R3是卤代甲基,卤代甲氧基,甲基,乙基,卤原子,氰基,甲硫基,硝基,氨基羰基,或氨基羰基甲基;R4是氢,卤原子或甲基;R5,R6,和R7在各种情况下各自独立地选自氢,卤原子,氰基,C1-C6-烷基,C2-C6-链烯基,C2-C6-炔基,C1-C4-烷氧基,C1-C4-烷硫基,C3-C4-环烷基和卤代甲氧基。这些化合物是有杀真菌活性的。
但是,上面的酰苯胺化合物表现出没有足够的广谱性和令人满意的作用范围。
本发明的一个目的是,提供一种控制有害真菌、特别是葡萄孢属的改进的可能性。
出人意料的是发现,通过含有与上述类型酰胺化合物混合的、抑制细胞色素复合体III上的呼吸作用的活性成分的组合物,可以实现本发明目的。
因此本发明涉及控制有害真菌的组合物,其在固体或液体载体中含有a)至少一种活性成分I,其抑制细胞色素复合体III上的呼吸作用,b)至少一种式II酰胺化合物
A-CO-NR1-R2 (II)其中A是芳基或含有1-3个选自O,N和S杂原子的芳香族或非芳香族5-元或6-元杂环;对于芳基或杂环来说,其可以是未取代的或者具有1,2或3个取代基,所述取代基各自独立地选自烷基,卤原子,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,烷基或烷氧基;R2是苯基或环烷基,其是未取代的或具有1-3个取代基,所述取代基各自独立地选自苯基,链烯基,炔基,链烯氧基,炔氧基,环烷基,环烯基,环烷基氧基和环烯氧基,这些取代基另外可以被一个或几个卤原子取代,对于脂肪族和环脂族残基来说,其可以是部分或全部卤化的和/或对于环脂族残基来说,其可以被1-3个烷基取代,对于苯基来说,其可以具有1-5个卤原子和/或1-3个取代基,所述取代基各自独立地选自烷基,卤代烷基,烷氧基,卤代烷氧基,烷硫基和卤代烷硫基,对于酰胺化苯基来说,其可以与饱和的5-元环稠合,所述5-元环是来取代的或被一个或几个烷基取代的和/或可以具有一个选自O和S的杂原子,但不包括式II化合物,其中A是2-氯代吡啶-3-基,R1是H和R2是
本发明组合物具有增效作用,因此特别适合控制有害真菌,特别是葡萄孢属。设定其以这样的事实为基础,即当细胞色素复合体III上的呼吸作用被抑制时,真菌利用了另一种呼吸作用的第二条途径,从而没有完全消灭真菌。这意味着式II酰胺化合物抑制另一种呼吸作用。因此必须肯定地推论,两种活性成分的结合抑制了通过细胞色素复合体III的呼吸作用,而且也抑制另一种呼吸作用,从而完全消灭了真菌。
本发明范围内的卤原子是氟,氯,溴和碘,特别是氟,氯和溴。
术语“烷基”包括直链或支链烷基。优选直链或支链C1-C12-烷基,特别是C1-C6-烷基。烷基的例子是例如甲基,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,正己基,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。
卤代烷基是被一个或几个卤原子、特别是氟和氯部分或全部卤化的如上所定义的烷基。优选存在1-3个卤原子,特别优选二氟甲基或三氟甲基。
上面对于烷基和卤代烷基的说明同样适用于烷氧基,氯代烷氧基,烷基硫代,卤代烷基硫代,烷基亚磺酰基和烷基磺酰基中的烷基和卤代烷基。
链烯基包括直链和支链链烯基。优选直链或支链C3-C12-链烯基,特别是C3-C6-链烯基。链烯基的例子是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-已烯基,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-4-丁烯基,1,2-二甲基-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。
链烯基可以被一个或几个卤原子、特别是氟和氯部分或全部卤化,优选具有1-3个卤原子。
炔基包括直链和支链炔基。优选直链和支链C3-C12-炔基,特别是C3-C6-炔基。链炔基的例子是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。
上述关于链烯基和其卤原子取代基、以及关于炔基的说明同样适用于链烯基氧基和炔基氧基。
环烷基优选是C3-C6-环烷基,例如环丙基,环丁基,环戊基,或环己基。如果环烷基是取代的,则优选具有1-3个C1-C4-烷基作为取代基。
环烯基优选是C4-C6-环烯基,例如环丁烯基,环戊烯基,或环己烯基。如果环烯基是取代的,则优选具有1-3个C1-C4-烷基作为取代基。
环烷氧基优选是C5-C6-环烷氧基,例如环戊基氧基,或环己基氧基。如果环烷氧基是取代的,则优选具有1-3个C1-C4-烷基作为取代基。
环烯基氧基优选是C5-C6-环烯基氧基,例如环戊烯基氧基,或环己烯基氧基。如果环烯基氧基是取代的,则优选具有1-3个C1-C4-烷基作为取代基。
芳基优选是苯基。
杂芳基优选是具有1,2或3个分别选自N,O和S杂原子的5-或6-元芳香族杂环,具体是吡啶基,嘧啶基,噻唑基,吡唑基,噁唑基,异噁唑基,异噻唑基,咪唑基,吡咯基,呋喃基,噻吩基或三唑基。
杂环基优选是具有1,2或3个各自独立地选自N,O和S杂原子的5-或6-元饱和的或不饱和的杂环,尤其是“杂芳基”所提及的残基的二氢-,四氢-或六氢衍生物。吡咯烷基,四氢呋喃基,咪唑烷基,吡唑烷基,噁唑烷基,异噁唑烷基,噻唑烷基,异噻唑烷基,哌啶基或吗啉基是优选的。
如果式II中的A是苯基,其可以在任何位置具有一个,两个或三个上述取代基。优选的是,这些取代基各自独立地选自烷基,二氟甲基,三氟甲基,和卤原子,特别是氯,溴和碘。特别优选的是该苯基在2-位上具有一个取代基。
如果A是一个5-元杂环,其特别是呋喃基,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。
其中X和Y之一是O,S或NR9,R9是H或烷基,残基X和Y的另一个是CH2,S,SO,SO2或NR9。虚线表示可以存在或不存在双键。
6-元芳香族杂环特别优选是吡啶基,特别是3-吡啶基或下式残基:其中X是CH2,S,SO或SO2。
上述杂环残基可以是未取代的或具有1,2或3个上述取代基,这些取代基优选各自独立地选自烷基,卤原子,二氟甲基或三氟甲基。
式II中的残基R1优选是氢原子。
式II中的残基R2优选是苯基。R2优选至少带有一个取代基,特别优选在2-位上。这一个或几个取代基优选选自烷基,环烷基,环烯基,卤原子或苯基。
基团R2的取代基也可以是被取代的。脂肪族或环脂族取代基可以是部分或全部卤化的,特别是被氟化或氯化。其优选带有1,2或3个氟原子或氯原子。如果基团R2的取代基是苯基,其优选被1-3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,苯基是在对位被一个卤原子取代,即特别优选的基团R2的取代基是在对位被卤原子取代的苯基残基。基团R2也可以与一个饱和的5-元环稠合,该5-元环还可以带有1-3个烷基取代基。在这种情况下,R2是例如2,3-二氢化茚基,硫杂2,3-二氢化茚基,氧杂2,3-二氢化茚基。优选是2,3-二氢化茚基和2-氧杂2,3-二氢化茚基,它们特别是通过4-位与氮原子键合。
活性成分I优选是式IA或IB化合物:其中…是双键或单键;
R′是-C[CO2CH3]=CHOCH3,-C[CO2CH3]=NOCH3,-C[CONHCH3]=NOCH3,
-C[CO2CH3]=CHCH3,-C[CO2CH3]=CHCH2CH3,-C[COCH3]=NOCH3,
-C[COCH2CH3]=NOCH3,-N(OCH3)-CO2CH3,-N(CH3)-CO2CH3或
-N(CH2CH3)-CO2CH3,R”是直接键合的或通过氧,巯基,氨基,或烷基氨基键合的有机基团,或与基团X和它们所键合的环Q或T一起形成未取代的或取代的双环,其是部分或完全不饱和的体系,其成环原子除碳外,还可以含有1,2或3个独立地选自氧,硫和氮的杂原子;Rx 是-OC[CO2CH3]=CHOCH3,-OC[CO2CH3]=CHCH3,-OC[CO2CH3]=CHCH2CH3,-SC[CO2CH3]=CHOCH3,-SC[CO2CH3]=CHCH3,-SC[CO2CH3]=CHCH2CH3,-N(CH3)C[CO2CH3]=CHOCH3,-N(CH3)C[CO2CH3]=NOCH3,-CH2C[CO2CH3]=CHOCH3,-CH2C[CO2CH3]=NOCH3或-CH2C[CONHCH3]=NOCH3;Ry是氧,硫,=CH-或=N-;n是0,1,2或3,如果n>1,则基团X可以是相同的或不同的;X是氰基,硝基,卤原子,烷基,卤代烷基,烷氧基,卤代烷氧基,烷硫基,或如果n>1,为C3-C5-亚烷基,C3-C5-亚链烯基,氧代-C2-C4-亚烷基,氧代-C1-C3-亚烷基氧基,氧代-C2-C4-亚链烯基,氧代-C2-C4-亚链烯基氧基,或与苯环的两个相邻碳原子键合的丁二烯二基,这些链本身还可以与1-3个残基相连,所述残基各自独立地选自卤原子,烷基,卤代烷基,烷氧基,卤代烷氧基和烷硫基;Y是=C-或-N-;Q是苯基,吡咯基,噻吩基,呋喃基,吡唑基,咪唑基,噁唑基,异噁唑基,噻唑基,噻二唑基,三唑基,吡啶基,2-吡啶基,嘧啶基或三嗪基;和T是苯基,噁唑基,噻唑基,噻二唑基,噁二唑基,吡啶基,嘧啶基或三嗪基。
取代基R”特别是烷基,链烯基,炔基,芳基,杂芳基,芳基烷基,杂芳基烷基,芳基链烯基,杂芳基链烯基,芳基炔基,或杂芳基炔基,其中可以没有或被一个或几个选自O,S,SO,SO2,NR(R=H或烷基),CO,COO,OCO,CONH,NHCO,NHCONH基团间隔,或者是下面定义的式CH2ON=CRαCRβ或CH2ON=CRγCRδ=NORε残基。这些基团是未取代的或带有一个或几个(优选1,2或3个)取代基,所述取代基各自独立地选自烷基,烷氧基,卤原子,氰基,卤代烷基(特别是CF3和CHF2),杂芳基和芳基。杂芳基和芳基还可以带有1,2或3个各自独立地选自卤原子,卤代烷基(特别是CF3和CHF2),苯基,CN,苯氧基,烷基,烷氧基和卤代烷氧基的取代基。
这些化合物及其制剂公开在下面表I.1至I.8中给出的文献中。其中没有描述的化合物可以通过类似方法制备。
在一个优选的实施方案中,本发明组合物含有一种式IA或IB化合物,其中R”是芳氧基,杂芳氧基,芳氧基亚甲基,杂芳氧基亚甲基,芳基亚乙烯基或杂芳基亚乙烯基,这些基团可以是未取代的或带有1,2或3个取代基,所述取代基各自独立地选自烷基,卤原子,CF3,CHF2,CN,烷氧基和苯基,这些取代基本身还可以带有1,2或3个各自独立地选自卤原子,CF3,CHF2,苯基,CN,苯氧基,烷基,烷氧基和卤代烷氧基的取代基;
或者R”是CH2ON=CRαRβ或CH2ON=CRγCRδ=NORε,其中Rα是烷基;Rβ是未取代的或带有1,2或3个各自独立地选自烷基,烷氧基,卤原子,卤代烷氧基,CF3和CHF2取代基的苯基,吡啶基或嘧啶基;Rγ是烷基,烷氧基,卤原子,卤代烷基,或氢;Rδ是氢,氰基,卤原子,烷基,烷氧基,烷硫基,烷基氨基,二烷基氨基,链烯基,链烯基氧基,链烯硫基,链烯基氨基,N-链烯基-N-烷基氨基,炔基,炔基氧基,炔硫基,炔基氨基,N-炔基-N-烷基氨基,这些基团中的烃基可以是部分或全部卤化的和/或其上连接有1,2或3个基团,所述基团各自独立地选自氰基,硝基,羟基,烷氧基,卤代烷氧基,烷氧基羰基,烷硫基,烷基氨基,二烷基氨基,链烯基氧基,环烷基,环烷基氧基,杂环基,杂环基氧基,芳基,芳基氧基,芳基烷氧基,杂芳基,杂芳基氧基,和杂芳基烷氧基,所述环残基本身还可以是部分或全部卤化的和/或其上连接有1,2或3个基团,所述基团各自独立地选自氰基,硝基,羟基,烷基,卤代烷基,环烷基,烷氧基,卤代烷氧基,烷氧基羰基,烷硫基,烷基氨基,二烷基氨基,链烯基和链烯基氧基;或者是环烷基,环烷基氧基,环烷基硫基,环烷基氨基,N-环烷基-N-烷基氨基,杂环基,杂环基氧基,杂环基硫基,杂环基氨基,N-杂环基-N-烷基氨基,芳基,芳基氧基,芳基硫基,芳基氨基,N-芳基-N-烷基氨基,杂芳基,杂芳基氧基,杂芳基硫基,杂芳基氨基或N-杂芳基-N-烷基氨基,所述环残基可以是部分或全部卤化的和/或其上连接有1,2或3个基团,所述基团各自独立地选自氰基,硝基,羟基,烷基,卤代烷基,环烷基,烷氧基,卤代烷氧基,烷氧基羰基,烷硫基,烷基氨基,二烷基氨基,链烯基,链烯基氧基,苄基,苄基氧基,芳基,芳基氧基,杂芳基和杂芳基氧基,所述芳香族残基本身还可以是部分或全部卤化的和/或与其连接有1,2或3个氰基,烷基,卤代烷基,烷氧基,硝基基团;Rε是烷基,链烯基,或炔基,这些基团可以是部分或全部卤化的和/或其上连接有1,2或3个氰基,烷氧基,环烷基基团。
特别优选的是式IA或IB化合物,其中R”具有下面定义之一:a)苯氧基亚甲基,吡啶基氧基亚甲基,嘧啶基氧基亚甲基或吡唑基氧基亚甲基,所述芳香基团可以是未取代的或带有1,2或3个取代基,所述取代基各自独立地选自烷基,卤原子,CF3,CHF2,-C(CH3)=NOCH3,和未取代的或被1,2或3个卤原子和/或烷基取代的苯基;b)苯氧基,或嘧啶基氧基,其是未取代的或被1,2或3个卤原子取代,或者是未取代的或带有一个卤原子或氰基取代基的苯氧基;c)苯基亚乙烯基或吡唑基亚乙烯基,其中苯基或吡唑残基可以是未取代的或带有1,2或3个各自独立地选自卤原子,CF3,CHF2,和苯基的取代基;d)CH2ON=CRαRβ,其中Rα是烷基;和Rβ是未取代的或带有1,2或3个各自独立地选自烷基,卤原子,CF3,CHF2
取代基的苯基,或者是未取代的或被1或2个烷氧基取代的嘧啶基;e)CH2ON=CRγCRδ=NORε
其中Rγ是烷基,烷氧基,或卤原子;Rδ是烷基,氰基,卤原子,烷氧基,链烯基,或未取代的或被1,2或3个卤原子取代的苯基;和Rε是烷基。
特别优选的是其中Q是苯基及n是0的式IA化合物。
特别合适的活性成分I是下面表中列出的化合物。表I.1A
式IA化合物,其中Q是苯基,R’是-C(CO2CH3)=CHOCH3,n是0,R”是未取代的或取代的(杂)芳基氧基亚甲基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.1B
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.1A-1 | 2-CH3-C6H4 | EP-A 226 917 |
I.1A-2 | 2,5-(CH3)2-C6H3 | EP-A 226 917 |
I.1A-3 | 2-CH3,4-C[CH3]=NOCH3-C6H3 | EP-A 386 561 |
I.1A-4 | 2-CH2CH2CH3,6-CF3-嘧啶-4-基 | EP-A 407 873 |
I.1A-5 | 2,4-(CH3)2-C6H3 | EP-A 226 917 |
式IA化合物,其中R’是-C(CO2CH3)=CHOCH3,Q是苯基,n是0,R”是未取代的或取代的(杂)芳基氧基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.1C
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.1B-1 | C6H5 | EP-A 178 826 |
I.1B-2 | 6-[2-CN-C6H4-O]-嘧啶-4-基 | EP-A 382 375 |
式IA化合物,其中R’是-C(CO2CH3)=CHOCH3,Q是苯基,n是0,R”是未取代的或取代的(杂)芳基氧基亚乙烯基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.1D
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.1C-1 | 1-(2,4-Cl2-C6H3),5-CF3-pyrazol-4-yl | EP-A 528 245 |
I.1C-2 | 1-(4-Cl-C6H4)-密啶-4-基 | EP-A 378 755 |
I.1C-3 | 3-CF3-C6H4 | EP-A 203 606 |
I.1C-4 | 3-Cl-C6H4 | EP-A 203 606 |
I.1C-5 | 4-C6H5-C6H4 | EP-A 203 606 |
式IA化合物,其中Q是苯基,R’是-C(CO2CH3)=CHOCH3,n是0,R”是CH2ON=CRαRβ,Rα和Rβ具有下面的定义
表I.1E
序号 | Rα | Rβ | 文献 |
I.1D-1 | CH3 | 4-Cl-C6H4 | EP-A 370 629 |
I.1D-2 | CH3 | 3-CF3-C6H4 | EP-A 370 629 |
I.1D-3 | CH3 | 4-OCH2CH3-嘧啶-2-基 | WO-A 92/18,487 |
式IA化合物,其中Q是苯基,R’是-C(CO2CH3)=CHOCH3,n是0,R”是CH2ON=CRγCRδ=NORε,Rγ,Rδ和Rε具有下面的定义
表I.2A
序号 | Rγ | Rδ | Rε | 文献 |
I.1E-1 | CH3 | CH3 | CH3 | WO-A 95/21153 |
I.1E-2 | CH3 | CH3 | CH2CH3 | WO-A 95/21153 |
I.1E-3 | CH3 | C6H5 | CH3 | WO-A 95/21153 |
I.1E-4 | CH3 | C6H5 | CH2CH3 | WO-A 95/21153 |
I.1E-5 | CH3 | 4-Cl-C6H4 | CH3 | WO-A 95/21153 |
I.1E-6 | CH3 | 4-Cl-C6H4 | CH2CH3 | WO-A 95/21153 |
式IA化合物,其中Q是苯基,R’是-C(CO2CH3)=NOCH3,n是0,R”是未取代的或取代的(杂)芳基氧基亚甲基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.2B
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.2A-1 | 2-CH3-C6H4 | EP-A 253 213 |
I.2A-2 | 2,5-(CH3)2-C6H3 | EP-A 400 417 |
I.2A-3 | 2,4-(CH3)2-C6H3 | EP-A 400 417 |
I.2A-4 | 2,3,5-(CH3)3-C6H2 | EP-A 400 417 |
I.2A-5 | 2-Cl,5-CH3-C6H3 | EP-A 400 417 |
I.1A-6 | 2-CH3,4-C[CH3]=NOCH3-C6H3 | EP-A 386 561 |
式IA化合物,其中Q是苯基,R’是-C(CO2CH3)=NOCH3,n是0,R”是未取代的或取代的(杂)芳基氧基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.2C
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.2B-1 | C6H5 | EP-A 253 213 |
I.2B-2 | 6-[2-CN-C6H4-O]-嘧啶-4-基 | EP-A 468 684 |
式IA化合物,其中Q是苯基,R’是-C(CO2CH3)=NOCH3,n是0,R”是CH2ON=CRαRβ,Rα和Rβ具有下面的定义
表I.2D
序号 | Rα | Rβ | 文献 |
I.2C-1 | CH3 | 4-Cl-C6H4 | EP-A 463 488 |
I.2C-2 | CH3 | 3-Cl-C6H4 | EP-A 463 488 |
I.2C-3 | CH3 | 4-CF3-C6H4 | EP-A 463 488 |
I.2C-4 | CH3 | 3-CF3-C6H4 | EP-A 463 488 |
I.2C-5 | CH3 | 4-CH3-C6H4 | EP-A 463 488 |
I.2C-6 | CH3 | 4-OCH2CH3-嘧啶-2-基 | EP-A 472 300 |
I.2C-7 | CH3 | 3,5-Cl2-C6H3 | EP-A 463 488 |
式IA化合物,其中Q是苯基,R’是-C(CO2CH3)=NOCH3,n是0,R”是CH2ON=CRγCRδ=NORε,Rγ,Rδ和Rε具有下面的定义
表I.3A式IA化合物,其中Q是苯基,R’是-C(CONHCH3)=NOCH3,n是0,R”是未取代的或取代的(杂)芳基氧基亚甲基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.3B
序号 | Rγ | Rδ | Rε | 文献 |
I.2D-1 | CH3 | CH3 | CH3 | WO-A 95/21153 |
I.2D-2 | CH3 | CH3 | CH2CH3 | WO-A 95/21153 |
I.2D-3 | CH3 | C6H5 | CH3 | WO-A 95/21153 |
I.2D-4 | CH3 | C6H5 | CH2CH3 | WO-A 95/21153 |
I.2D-5 | CH3 | 4-Cl-C6H4 | CH3 | WO-A 95/21153 |
I.2D-6 | CH3 | 4-Cl-C6H4 | CH2CH3 | WO-A 95/21153 |
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.3A-1 | 2-CH3-C6H4 | EP-A 477 631 |
I.3A-2 | 2,5-(CH3)2-C6H3 | EP-A 477 631 |
I.3A-3 | 2,4-(CH3)2-C6H3 | EP-A 477 631 |
I.3A-4 | 2,3,5-(CH3)3-C6H2 | EP-A 477 631 |
I.3A-5 | 2-CH3,4-C[CH3]=NOCH3-C6H3 | EP-A 579 124 |
I.3A-6 | 1-[4-Cl-C6H4]-吡唑-3-基 | WO-A 94/19331 |
I.3A-7 | 1-[2,4-Cl2-C6H3]-吡唑-3-基 | WO-A 94/19331 |
式IA化合物,其中Q是苯基,R’是-C(CONHCH3)=NOCH3,n是0,R”是未取代的或取代的(杂)芳基氧基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.3C
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.3B-1 | C6H5 | EP-A 398 692 |
I.3B-2 | 6-[2-CN-C6H4-O]-嘧啶-4-基 | GB-A 2 253 624 |
式IA化合物,其中Q是苯基,R’是-C(CONHCH3)=NOCH3,n是0,R”是未取代的或取代的(杂)芳基亚乙烯基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.3D
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.3C-1 | 1-[2,4-Cl2-C6H3],5-CF3-吡唑-4-基 | DE-A 44 23 615.8 |
式IA化合物,其中Q是苯基,R’是-C(CONHCH3)=NOCH3,n是0,R”是CH2ON=CRαRβ,Rα和Rβ具有下面的定义
表I.3E
序号 | Rα | Rβ | 文献 |
I.3D-1 | CH3 | 4-Cl-C6H4 | EP-A 463 488 |
I.3D-2 | CH3 | 3-Cl3-C6H4 | EP-A 463 488 |
I.3D-3 | CH3 | 4-CF3-C6H4 | EP-A 585 751 |
I.3D-4 | CH3 | 3-CF3-C6H4 | EP-A 585 751 |
I.3D-5 | CH3 | 4-CH3-C6H4 | EP-A 463 488 |
I.3D-6 | CH3 | 3,5-Cl2-C6H3 | EP-A 463 488 |
I.3D-7 | CH3 | 2-OCH2CH3-嘧啶-2-基 | WO-A 92/13,830 |
式IA化合物,其中Q是苯基,R’是-C(CONHCH3)=NOCH3,n是0,R”是CH2ON=CRγCRδ=NORε,Rγ,Rδ和Rε具有下面的定义
表I.4A
序号 | Rγ | Rδ | Rε | 文献 |
I.3E-1 | CH3 | CH3 | CH3 | WO-A 95/21154 |
I.3E-2 | CH3 | CH3 | CH2CH3 | WO-A 95/21154 |
I.3E-3 | CH3 | C6H5 | CH3 | WO-A 95/21154 |
I.3E-4 | CH3 | C6H5 | CH2CH3 | WO-A 95/21154 |
I.3E-5 | CH3 | 4-Cl-C6H4 | CH3 | WO-A 95/21154 |
I.3E-6 | CH3 | 4-Cl-C6H4 | CH2CH3 | WO-A 95/21154 |
I.3E-7 | CH3 | 4-F-C6H4 | CH3 | WO-A 95/21154 |
IA化合物,其中Q是苯基,R’是-C(CO2CH3)=CHCH3,n是0,R”是未取代的或取代的(杂)芳基氧基亚甲基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.4B
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.4A-1 | 2-CH3-C6H4 | EP-A 280 185 |
I.4A-2 | 2,5-(CH3)2-C6H3 | EP-A 513 580 |
I.4A-3 | 2,4-(CH3)2-C6H3 | EP-A 513 580 |
I.4A-4 | 2,3,5-(CH3)3-C6H2 | EP-A 513 580 |
I.4A-5 | 2-Cl,5-CH3-C6H3 | EP-A 513 580 |
I.4A-6 | 2-CH3,4-C[CH3]=NOCH3-C6H3 | EP-A 513 580 |
I.4A-7 | 1-[4-Cl-C6H4]-吡唑-3-基 | DE-A 44 15483.6 |
式IA化合物,其中Q是苯基,R’是-C(CO2CH3)=CHCH3,n是0,R”是未取代的或取代的(杂)芳基氧基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.4C
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.4B-1 | C6H5 | EP-A 513 580 |
式IA化合物,其中Q是苯基,R’是-C(CO2CH3)=CHCH3,n是0,R”是CH2ON=CRγCRδ=NORε,Rγ,Rδ和Rε具有下面的定义
表I.5A
序号 | Rγ | Rδ | Rε | 文献 |
I.4C-1 | CH3 | CH3 | CH3 | WO-A 95/21153 |
I.4C-2 | CH3 | CH3 | CH2CH3 | WO-A 95/21153 |
I.4C-3 | CH3 | C6H5 | CH3 | WO-A 95/21153 |
I.4C-4 | CH3 | C6H5 | CH2CH3 | WO-A 95/21153 |
I.4C-5 | CH3 | 4-Cl-C6H4 | CH3 | WO-A 95/21153 |
I.4C-6 | CH3 | 4-Cl-C6H4 | CH2CH3 | WO-A 95/21153 |
式IA化合物,其中Q是苯基,R’是-C(CO2CH3)=CHCH2CH3,n是0,R”是未取代的或取代的(杂)芳基氧基亚甲基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.5B
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.5A-1 | 2-CH3-C6H4 | EP-A 513 580 |
I.5A-2 | 2,5-(CH3)2-C6H3 | EP-A 513 580 |
I.5A-3 | 2,4-(CH3)2-C6H3 | EP-A 513 580 |
I.5A-4 | 2,3,5-(CH3)3-C6H2 | EP-A 513 580 |
I.5A-5 | 2-Cl,5-CH3-C6H3 | EP-A 513 580 |
I.5A-6 | 2-CH3,4-C[CH3]=NOCH3-C6H3 | EP-A 513 580 |
式IA化合物,其中Q是苯基,R’是-C(CO2CH3)=CHCH2CH3,n是0,R”是未取代的或取代的(杂)芳基氧基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.5C
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.5B-1 | C6H5 | EP-A 513 580 |
式IA化合物,其中Q是苯基,R’是-C(CO2CH3)=CHCH2CH3,n是0,R”是CH2ON=CRγCRδ=NORε,Rγ,Rδ和Rε具有下面的定义
表I.6A
序号 | Rγ | Rδ | Rε | 文献 |
I.5C-1 | CH3 | CH3 | CH3 | WO-A 95/21153 |
I.5C-2 | CH3 | CH3 | CH2CH3 | WO-A 95/21153 |
I.5C-3 | CH3 | C6H5 | CH3 | WO-A 95/21153 |
I.5C-4 | CH3 | C6H5 | CH2CH3 | WO-A 95/21153 |
I.5C-5 | CH3 | 4-Cl-C6H4 | CH3 | WO-A 95/21153 |
I.5C-6 | CH3 | 4-Cl-C6H4 | CH2CH3 | WO-A 95/21153 |
式IA化合物,其中Q是苯基,R’是-C(COCH3)=NOCH3,n是0,R”是未取代的或取代的(杂)芳基氧基亚甲基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.6B
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.6A-1 | 2-CH3-C6H4 | EP-A 498 188 |
I.6A-2 | 2,5-(CH3)2-C6H3 | EP-A 498 188 |
I.6A-3 | 2,4-(CH3)2-C6H3 | EP-A 498 188 |
I.6A-4 | 2,3,5-(CH3)3-C6H2 | EP-A 498 188 |
I.6A-5 | 2-CH3,4-C[CH3]=NOCH3-C6H3 | EP-A 498 188 |
式IA化合物,其中Q是苯基,R’是-C(COCH3)=NOCH3,n是0,R”是未取代的或取代的(杂)芳基氧基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.7A
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.6B-1 | C6H5 | EP-A 498 188 |
I.6B-2 | 6-[2-CN-C6H4-O]-嘧啶-4-基 | EP-A 498 188 |
式IA化合物,其中Q是苯基,R’是-C(COCH2CH3)=NOCH3,n是0,R”是未取代的或取代的(杂)芳基氧基亚甲基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.7B
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.7A-1 | 2-CH3-C6H4 | EP-A 498 188 |
I.7A-2 | 2,5-(CH3)2-C6H3 | EP-A 498 188 |
I.7A-3 | 2,4-(CH3)2-C6H3 | EP-A 498 188 |
I.7A-4 | 2,3,5-(CH3)3-C6H2 | EP-A 498 188 |
I.7A-5 | 2-CH3,4-C[CH3]=NOCH3-C6H3 | EP-A 498 188 |
式IA化合物,其中Q是苯基,R’是-C(COCH2CH3)=NOCH3,n是0,R”是未取代的或取代的(杂)芳基氧基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.8A
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.7B-1 | C6H5 | EP-A 498 188 |
I.7B-2 | 6-[2-CN-C6H4-O]-嘧啶-4-基 | EP-A 498 188 |
式IA化合物,其中Q是苯基,R’是N-(OCH3)-CO2CH3,n是0,R”是未取代的或取代的(杂)芳基氧基亚甲基,其中未取代的或取代的(杂)芳基基团具有下面的定义
表I.8B
序号 | 未取代的或取代的(杂)芳基 | 文献 |
I.8A-1 | 2-CH3-C6H4 | WO-A 93/15,046 |
I.8A-2 | 2,5-(CH3)2-C6H3 | WO-A 93/15,046 |
I.8A-3 | 2,4-(CH3)2-C6H3 | WO-A 93/15,046 |
I.8A-4 | 2,3,5-(CH3)3-C6H2 | WO-A 93/15,046 |
I.8A-5 | 2-Cl,5-CH3-C6H3 | WO-A 93/15,046 |
I.8A-6 | 2-CH3,4-C[CH3]=NOCH3-C6H3 | WO-A 93/15,046 |
I.8A-7 | 2-CH3,4-C[CH3]=NOCH2CH3-C6H3 | WO-A 93/15,046 |
I.8A-8 | 2-CH3,4-C[CH2CH3]=NOCH3-C6H3 | WO-A 93/15,046 |
I.8A-9 | 2-CH3,4-C[CH2CH3]=NOCH2CH3-C6H3 | WO-A 93/15,046 |
I.8A-10 | 1-[4-Cl-C6H4]-吡唑-3-基 | DE-A 44 23 612.3 |
式IA化合物,其中Q是苯基,R’是-N(OCH3)=CO2CH3,n是0,R”是CH2ON=CRαRβ,Rα和Rβ具有下面的定义
序号 | Rα | Rβ | 文献 |
I.8B-1 | CH3 | 3,5-Cl2-C6H3 | WO-A 93/15,046 |
在又一个优选实施方案中,本发明组合物含有作为酰胺化合物的式II化合物,其中A具有下面的含义:
苯基,吡啶基,二氢吡喃基,二氢氧硫杂环己二烯基,二氢氧硫杂环己二烯基氧化物,二氢氧硫杂环己二烯基二氧化物,呋喃基,噻唑基,吡唑基,或噁唑基,这些取代基可以带有1,2或3个各自独立地选自烷基,卤原子,二氟甲基,和三氟甲基的取代基。
在又一个优选实施方案中,A代表:吡啶-3-基,其是未取代的或在2-位被卤原子,甲基,二氟甲基,三氟甲基,甲氧基,甲基硫代,甲基亚磺酰基或甲基磺酰基取代;苯基,其是未取代的或在2-位被甲基,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,其是未取代的或在4-和/或5-位被甲基取代;噻唑-5-基,其是未取代的或在2-和/或4-位被甲基,氯,二氟甲基或三氟甲基取代;噻唑-4-基,其是未取代的或在2-和/或5-位被甲基,氯,二氟甲基或三氟甲基取代;1-甲基吡唑-4-基,其是未取代的或在3-和/或5-位被甲基,氯,二氟甲基或三氟甲基取代;或噁唑-5-基,其是未取代的或在2-和/或4-位被甲基或氯取代;
在又一个优选实施方案中,本发明组合物含有作为酰胺化合物的式II化合物,其中R2是未取代的或被1,2或3个上述取代基取代的苯基。
在又一个优选实施方案中,本发明组合物含有作为酰胺化合物的式II化合物,其中R2是在2-位具有下述取代基之一的苯基;C3-C6-烷基,C5-C6-环烯基,C5-C6-环烷基氧基,C5-C6-环烯基氧基,这些基团可以被1,2或3个C1-C4-烷基取代,苯基,其被1-5个卤原子和/或1-3个各自独立地选自C1-C4-烷基,C1-C4-卤代烷基,C1-C4-烷氧基,C1-C4-卤代烷氧基,C1-C4-烷基硫代,和C1-C4-卤代烷硫基的基团取代,2,3-二氢化茚基或氧杂2,3-二氢化茚基,其是未取代的或被1,2或3个C1-C4-烷基取代。
在又一个优选实施方案中,本发明组合物含有作为酰胺化合物的式IIa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,和R10是C1-C4-烷基,C1-C4-烷氧基,C1-C4-烷硫基或卤原子。
合适的酰胺化合物是EP-A-545099和589301中提到的化合物,这两篇文献全文在此提及并并入作为参考。
式I酰胺化合物的制剂公开于例如EP-A-545099和589301中,或者可以通过相似方法制备。
为了获得增效作用,以20∶1至1∶20,特别是10∶1至1∶10范围的重量比例使用活性成分。
本发明也涉及控制有害真菌的方法,包括用上面定义的组合物处理真菌,其环境,或要保护使不受真菌侵害的材料,植物,种子,土壤,表面或空间,可以同时即结合,或分开,或依次施用活性成分。
可以以下述形式施用本发明组合物,例如,以可直接可喷雾溶液,粉剂,混悬剂的形式,也可以以高浓含水,油或其它混悬剂或分散剂,乳剂,油分散剂,糊剂,细粉剂的形式,通过喷雾,弥雾,喷粉,散播或散布用于散播的材料或颗粒剂。使用形式取决于要达到的目的;在任何情况下,应该保证本发明活性成分的最可能均匀的分布。
通常,用本发明活性成分对植物喷雾或喷粉,或者用活性成分处理植物的种子。
用已知方法制备制剂,例如通过用溶剂和/或载体,如果需要的话,用乳化剂和分散剂增充活性成分,如果用水作为稀释剂的话,也可以使用其它有机溶剂作为辅助溶剂。合适的助剂主要有:溶剂例如芳烃(例如二甲苯),氯代芳烃(氯苯),链烷烃(例如矿物油级分),醇(例如甲醇,丁醇),酮(例如环己酮),胺(例如乙醇胺,二甲基甲酰胺)和水。载体例如磨细的天然矿物(例如高岭土,粘土,滑石,白垩)和磨细的合成矿物(例如高度分散的硅石,硅酸盐);乳化剂例如非离子和阴离子乳化剂(例如聚氧乙烯脂肪醇醚,烷基磺酸盐和芳基磺酸盐)和分散剂,例如木素-亚磺酸盐废液和甲基纤维素。
合适的表面活性剂是芳香族磺酸的例如木素-,苯酚-,萘-,和二丁基萘磺酸的碱金属盐,-碱土金属盐,和-铵盐,和脂肪酸的、烷基-和烷基芳基磺酸的、烷基硫酸的、月桂基醚硫酸的和脂肪醇硫酸的碱金属盐,-碱土金属盐,和-铵盐;以及硫酸化十六-十七-和十八醇的盐,以及还有脂肪醇乙二醇醚,磺化萘及其衍生物与甲醛的缩聚物,萘或萘磺酸与苯酚和甲醛的缩聚物,聚氧乙烯辛基苯基醚,乙氧化异辛基-,辛基-,或壬基苯酚,烷基苯基聚乙二醇醚,三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷基醇,脂肪醇/环氧乙烷缩聚物,乙氧化蓖麻油,聚氧乙烯烷基醚或聚氧丙烯烷基醚,月桂基醇聚乙二醇醚乙酸山梨糖醇酯,木素-亚磺酸盐废液或甲基纤维素。
粉剂,散播材料和细粉剂可以通过将活性物质与一种固体载体混合或一起研磨而制备。
颗粒剂,例如包衣的颗粒剂,浸制的颗粒剂或均匀颗粒剂可以通过使活性成分与固体载体粘合而制备。固体载体是矿物质,例如硅胶,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,粘土,石灰岩,硅藻土,硫酸钙,硫酸镁,氧化镁,磨细的合成材料,化肥,例如硫酸铵,磷酸铵,硝酸铵,尿素,和植物来源产品例如谷粉,树皮粉,木屑和坚果外壳粉,纤维素粉末或其它固体载体。
以1∶1重量比含有活性成分的这样的制剂的例子是:
I.90重量份活性成分和10重量份适用于微滴形式的N-甲基吡咯烷酮的溶液;
II.20重量份活性成分,80重量份二甲苯,10重量份的8-10mol环氧乙烷与1mol油酸N-单乙醇酰胺的加成物,5重量份的十二烷基苯磺酸钙,5重量份的40mol环氧乙烷与1mol蓖麻油的加成物的混合物;通过将该溶液细密分布于水中而得到分散液;
III.20重量份活性成分,40重量份环己酮,30重量份异丁醇,20重量份的40mol环氧乙烷与1mol蓖麻油的加成物的水分散液;
IV.20重量份活性成分,25重量份环己醇,65重量份沸点是210-280℃的矿物油级分和10重量份的,40mol环氧乙烷与1mol蓖麻油的加成物的水分散液;
V.80重量份活性成分,3重量份二异丁基萘-1-磺酸钠,10重量份来自亚磺酸盐废液的木素磺酸钠盐和7重量份粉末状硅胶在锤磨机中磨细的混合物;将该混合物细密地分布于水中,得到喷雾混合物;
VI.3重量份活性成分和97重量份磨细的高岭土的细密的混合物;该细粉剂含有3%重量比的活性成分;
VII.30重量份活性成分,92重量份粉末状硅胶和8重量份石蜡油,其中石蜡油被喷雾到所述硅胶表面;该制剂赋予活性成分好的粘附性能;
VIII.40重量份活性成分,10重量份苯酚磺酸/尿素/甲醛缩聚物的钠盐,2重量份硅胶和48重量份水的稳定的水分散液;该分散液可以进一步稀释;
IX.20重量份活性成分,2重量份十二烷基苯磺酸钙,8重量份脂肪醇聚乙二醇醚,20重量份苯酚磺酸/尿素/甲醛缩聚物的钠盐和88重量份石蜡油的稳定的油分散液。
本发明组合物的特征在于其抗广谱病原真菌、特别是抗葡萄孢属的突出的活性。其中一些是系统作用(即其可以被被处理植物吸收而不损失其活性,如果需要,在植物中易位)并可以用作叶作用和土壤作用杀真菌剂。
它们对于控制不同农作物和这些植物的种子中大量真菌特别重要,所述农作物例如小麦,黑麦,大麦,燕麦,稻,玉米,草皮,棉花,大豆,咖啡,甘蔗,葡萄藤,水果,观赏植物和蔬菜例如黄瓜,豆角和葫芦。
本发明组合物通过使用杀真菌活性量的活性成分来处理真菌、或待保护使其不受真菌侵害的种子,植物,材料或土壤而施用。
在真菌侵害材料,植物或种子之前或之后施用是有效的。
具体来说,本发明组合物适合控制下面的植物病害:谷类禾白粉菌(Erysiphe graminis,白粉菌),葫芦二孢白粉菌(Erysiphe cichoracearum)和苍耳单丝壳菌(Sphaerothecafuliginea),苹果的苹果白粉病柄球菌(Podosphaera leucotricha),葡萄藤葡萄白粉病钩丝壳霉(Uncinula necator),苹果的苹果黑星菌(Venturia inaequalis)(scab),谷类长蠕孢属(Helminthosporium),小麦颍枯壳针孢(Septoria nodorum),草莓和葡萄藤灰色葡萄孢(Botrytis cinerea,灰霉),花生的花生尾孢(Cercospora arachidicola),小麦和大麦的Pseudocercosporella herpotrichoides,稻的Pyricularia oryzae,各种植物,蔬菜和水果的变种的镰孢属和轮枝孢属(Fusarium,Verticillium),水果的链核盘菌属(Monilinia species),油菜籽油菜和蔬菜的核盘菌属(Sclerotinia)。
优选抗葡萄孢属的用途。
本发明组合物也可以用来保护材料(保护木材),例如抗宛氏拟青霉(Paecilomyces variotii)。
一般情况下,本发明杀真菌组合物含有0.1-95,优选0.5-90重量百分比的活性化合物。
根据所预期作用的性质,施用比例为每公顷0.02-3kg活性成分。处理种子时每公斤种子一般需要0.001-50g,优选0.01-10g活性成分。
在杀真菌剂形式的使用形式中,本发明组合物也可以含有其它活性成分,例如,除草剂,杀虫剂,生长调节剂,杀真菌剂或还有化肥。
在很多情况下,含有杀真菌剂的混合物产生加宽杀真菌谱的作用。
可以与本发明化合物混合使用的下面列出的杀真菌剂是为了详细说明可能的组合,而不意味着任何限制:硫,二硫代碳酸盐及其衍生物,例如二甲基二硫代氨基甲酸铁(III),二甲基二硫代氨基甲酸锌,亚乙基双二硫代氨基甲酸锌,亚乙基双二硫代氨基甲酸锰,亚乙基二氨基双二硫代氨基甲酸锰锌,二硫化四甲基秋兰姆,(N,N’-亚乙基双二硫代氨基甲酸)锌的氨配合物,(N,N’-亚丙基双二硫代氨基甲酸)锌的氨配合物,(N,N’-亚丙基双二硫代氨基甲酸)锌,N,N’-聚丙烯双(硫代氨基甲酰基)二硫化物,硝基衍生物,例如丁烯酸二硝基(1-甲基庚基)苯酯,3,3-二甲基丙烯酸2-仲丁基-4,6-二硝基苯酯,碳酸2-仲丁基-4,6-二硝基苯基异丙酯,5-硝基异邻苯二甲酸二异丙酯,杂环物质,例如乙酸2-十七烷基-2-咪唑啉酯,2,4-二氯代-6-(邻-氯代酰苯胺)-s-三嗪,邻苯二甲酰亚氨硫代膦酸O,O-二乙酯,5-氨基-1-[双(二甲基氨基)氧膦基]-3-苯基-1,2,4-三唑,2,3-二氰基-1,4-二硫代蒽醌,2-硫代-1,3-二硫杂环戊二烯[4,5-b]喹噁啉,1-(丁基氨基甲酰基)-2-苯并咪唑氨基甲酸酯,2-甲氧基羰基氨基苯并咪唑,2-(呋喃基-(2))苯并咪唑,2-(噻唑基-(4))苯并咪唑,N-(1,1,2,2-四氯代乙基硫代)四氢邻苯二甲酰亚胺,N-三氯代甲基硫代四氢邻苯二甲酰亚胺,N-三氯代甲基硫代邻苯二甲酰亚胺,N-二氯代氟代甲硫基-N’,N’-二甲基-N-苯基硫化酰胺,5-乙氧基-3-三氯代甲基-1,2,3-噻二唑,2-硫氰酸根合甲基硫代苯并噻唑,1,4-二氯代-2,5-二甲氧基苯,4-(2-氯代苯基亚肼基)-3-甲基-5-异噁唑酮,吡啶-2-硫醇1-氧化物,8-羟基喹啉及其铜盐,2,3-二氢-5-甲酰苯胺-6-甲基-1,4-氧硫杂环己二烯,2,3-二氢-5-甲酰苯胺-6-甲基-1,4-氧硫杂环己二烯4,4-二氧化物,2-甲基-5,6-二氢-4H-吡喃-3-甲酰苯胺,2-甲基呋喃-3-甲酰苯胺,2,5-二甲基呋喃-3-甲酰苯胺,2,4,5-三甲基呋喃-3-甲酰苯胺,N-环己基-2,5-二甲基呋喃-3-甲酰胺,N-环己基-N-甲氧基-2,5-二甲基呋喃-3-甲酰胺,2-甲基苯甲酰苯胺,2-碘代苯甲酰苯胺,乙酸N-甲酰-N-吗啉-2,2,2-三氯代乙酯,哌嗪-1,4-二基双(1-(2,2,2-三氯代乙基))甲酰胺,1-(3,4-二氯代酰苯胺)-1-甲酰基氨基-2,2,2-三氯代乙烷,2,6-二甲基-N-十三烷基吗啉及其盐,2,6-二甲基-N-环十二烷基吗啉及其盐,N-[3-(对-叔丁基苯基)-2-甲基丙基]-顺-2,6-二甲基吗啉,N-[3-(对-叔丁基苯基)-2-甲基丙基]哌啶,1-[2-(2,4-二氯代苯基)4-乙基-1,3-二氧戊环-2-基-乙基]-1H-1,2,4-三唑,1-[2-(2,4-二氯代苯基)-4-正丙基-1,3-二氧戊环-2-基-乙基]-1H-1,2,4-三唑,N-(正丙基)-N-(2,4,6-三氯代苯氧基乙基)-N’-咪唑基脲,1-(4-氯代苯氧基)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁酮,1-(4-氯代苯基)-3,3-二甲基-1-(1H-1,2,4-三唑-1-基)-2-丁醇,α-(2-氯代苯基)-α-(4-氯代苯基)-5-嘧啶甲醇,5-丁基-2-二甲基氨基-4-羟基-6-甲基嘧啶,双(对-氯代苯基)-3-吡啶甲醇,1,2-双(3-乙氧基羰基-2-硫脲基)苯,1,2-双(3-甲氧基羰基-2-硫脲基)苯,和各种杀真菌剂,例如,十二烷基胍啶乙酸盐,3-[3-(3,5-二甲基)-2-氧环己基-2-羟基乙基]-戊二酰亚胺,六氯代苯,DL-甲基-N-(2,6-二甲基苯基)-N-(2-呋喃甲酰)丙氨酸酯,DL-N-(2,6-二甲基苯基)-N-(2’-甲氧基乙酰基)丙氨酸甲酯,N-(2,6-二甲基苯基)-N-氯代乙酰基-D,L-2-氨基丁内酯,DL-N-(2,6-二甲基苯基)-N-(苯基乙酰基)丙氨酸甲酯,5-甲基-5-乙烯基-3-(3,5-二氯代苯基)-2,4-二氧代-1,3-噁唑烷,3-[3,5-二氯代苯基-(5-甲基-5-甲氧基甲基)]-1,3-噁唑烷-2,4-二酮,3-(3,5-二氯代苯基)-1-异丙基氨基甲酰基乙内酰脲,N-(3,5-二氯代苯基)-1,2-二甲基环丙烷-1,2-二甲酰胺,2-氰基[N-(乙基氨基羰基)-2-甲氧基亚氨基]乙酰胺,1-[2-(2,4-二氯代苯基)戊基]-1H-1,2,4-三唑,2,4-二氟-α-(1H-1,2,4-三唑基-1-甲基)二苯甲基醇,N-(3-氯代-2,6-二硝基-4-三氟甲基苯基)-5-三氟甲基-3-氯代-2-氨基吡啶,1-((双(4-氟代苯基)甲基甲硅烷基)甲基)-1H-1,2,4-三唑。
用含有按干基计80%活性成分和20%乳化剂的水制剂向绿色钟状胡椒果实的花盘喷雾至液滴滴落点。喷雾层干燥2小时后,用含有1.7×106孢子/ml的2%浓度的Biomalz溶液的灰色葡萄孢的孢子悬浮液接种果实花盘。接着,接种的果实花盘在18℃湿润室中温育4天。然后目测评估感染的果实花盘上葡萄孢的生长(病害程度100%)。
将受侵害果实面积百分比的目测值转化成以来处理对照物的百分比%表示的效能。0值效能是未处理对照物上发现的相同病害程度,100值效能是0%病害程度。应用Colby计算式(Colby,S.R.“计算除草组合物的增效作用和拮抗反应”,《杂草》,15,20-22页,1967)确定活性成分组合物所预期的效能,并与实测效能比较。结果列于下面的表1。表1
*用Colby公式计算
活性成份 | 活性成份浓度(ppm) | 相对对照物百分数表示的效能 | ||
I.1-I.3 | II.1 | 实测值 | 计算值* | |
对照(未处理) | -- | -- | 0 | -- |
II.I | 157.5 | 5020 | ||
I.1 | 52.5 | 2515 | ||
I.2 | 52.5 | 2010 | ||
I.3 | 52.5 | 50 | ||
I.1+II.1 | 52.5 | 157.5 | 9997 | 6232 |
I.2+II.1 | 5 | 15 | 96 | 55 |
I.3+II.1 | 52.5 | 157.5 | 8660 | 5220 |
试验结果表明,在所有混合比下,所发现的效能超过事先用Colby计算式计算的加和效能,即存在增效作用。应用实施例2抗灰色葡萄孢活性
正常生长至4-5叶时,用含有按干基计80%活性成分和20%乳化剂的水混悬剂向钟状胡椒籽苗cv.“Neusiedler Ideal Elite”喷雾至液滴滴落点。喷雾层干燥后,用真菌灰色葡萄孢的分生孢子悬浮液对植物喷雾。并将植物放在22-24℃且高空气湿度的室中,5天后,未处理对照植物的病害程度是形成的叶枯萎涉及到了大多数叶(病害程度96%)。
将受侵害叶面积百分比的目测值转化成以来处理对照物的百分比%表示的效能。0值效能是未处理对照物发现的相同病害程度,100值效能是0%病害程度。应用Colby计算式(Colby,S.R.“计算除草组合物的增效作用和拮抗反应”,《杂草》,15,20-22页,1967)确定活性成分组合物所预期的效能,并与实测效能比较。结果列于下面的表2。表2
*用Colby公式计算
活性成份 | 活性成份浓度(ppm) | 相对对照物百分数表示的效能 | ||
I.1-I.3 | II.1 | 实测值 | 计算值* | |
对照(未处理) | 0 | |||
II.2 | -- | 2461.5 | 877928 | -- |
I.1 | 20.5 | -- | 00 | -- |
I.2 | 20.5 | -- | 00 | -- |
I.3 | 20.5 | -- | 00 | -- |
I.4 | 20.5 | -- | 00 | -- |
I.5 | 20.5 | -- | 00 | -- |
I.1+II.2 | 20.5 | 61.5 | 100100 | 8779 |
I.2+II.2 | 20.5 | 61.5 | 10099 | 8779 |
I.3+II.2 | 20.5 | 61.5 | 10099 | 8779 |
I.4+II.2 | 20.5 | 61.5 | 100100 | 8779 |
I.5+II.2 | 20.5 | 61.5 | 9990 | 8779 |
试验结果表明,在所有混合比下所发现的效能超过事先用Colby计算式计算的加和效能,即存在增效作用。
当使用的酰胺化合物是一种在下面表3中提及的式Ia化合物其中A是或另外的、在EP-A-545099和589301中提到的各化合物和/或上面表I.1至I.8中提到的各化合物之一时,得到了类似结果。表3
序号 | A | R3 | R4 | R5 | R6 | R7 | R8 | R9 | R10 | X | 物理数据 (℃) |
3.1 | A1 | CH3 | - | - | - | - | - | - | 2-F | - | |
3.2 | A1 | CH3 | - | - | - | - | - | - | 4-F | - | |
3.3 | A1 | CF3 | - | - | - | - | - | - | 2-F | - | |
3.4 | A1 | CF3 | - | - | - | - | - | - | 4-F | - | |
3.5 | A2 | - | Cl | - | - | - | - | - | 2-F | - | |
3.6 | A2 | - | Cl | - | - | - | - | - | 2-CH3 | - | 71-73 |
3.7 | A2 | - | Cl | - | - | - | - | - | 2-Cl | - | |
3.8 | A2 | - | Cl | - | - | - | - | - | 2-OCH3 | - | |
3.9 | A2 | - | Cl | - | - | - | - | - | 3-F | - | |
3.10 | A2 | - | Cl | - | - | - | - | - | 3-Cl | - | 95-98 |
3.11 | A2 | - | Cl | - | - | - | - | - | 3-CH3 | - | |
3.12 | A2 | - | Cl | - | - | - | - | - | 3-OCH3 | - | |
3.13 | A2 | - | Cl | - | - | - | - | - | 3-OiC3H7 | - | |
3.14 | A2 | - | Cl | - | - | - | - | - | 3-Br | - | |
3.15 | A2 | - | Cl | - | - | - | - | - | 4-F | - | 156-157 |
3.16 | A2 | - | Cl | - | - | - | - | - | 4-Cl | - | 142-144 |
3.17 | A2 | - | Cl | - | - | - | - | - | 4-CH3 | - | 115-117 |
3.18 | A2 | - | Cl | - | - | - | - | - | 4-OCH3 | - | 114-116 |
序号 | A | R3 | R4 | R5 | R6 | R7 | R8 | R9 | R10 | X | 物理数据 (℃) |
3.19 | A2 | - | Cl | - | - | - | - | - | 4-SCH3 | - | |
3.20 | A3 | - | - | - | - | - | - | - | 2-F | CH2 | |
3.21 | A3 | - | - | - | - | - | - | - | 3-F | CH2 | |
3.22 | A3 | - | - | - | - | - | - | - | 4-F | CH2 | |
3.23 | A3 | - | - | - | - | - | - | - | 3-Cl | CH2 | |
3.24 | A3 | - | - | - | - | - | - | - | 3-CH3 | CH2 | |
3.25 | A3 | - | - | - | - | - | - | - | 2-F | S | |
3.26 | A3 | - | - | - | - | - | - | - | 3-F | S | |
3.27 | A3 | - | - | - | - | - | - | - | 4-F | S | |
3.28 | A3 | - | - | - | - | - | - | - | 3-Cl | S | |
3.29 | A3 | - | - | - | - | - | - | - | 3-CH3 | S | |
3.30 | A3 | - | - | - | - | - | - | - | 2-F | SO2 | |
3.31 | A3 | - | - | - | - | - | - | - | 3-F | SO2 | |
3.32 | A3 | - | - | - | - | - | - | - | 4-F | SO2 | |
3.33 | A3 | - | - | - | - | - | - | - | 3-Cl | SO2 | |
3.34 | A3 | - | - | - | - | - | - | - | 3-CH3 | SO2 | |
3.35 | A5 | - | - | - | CF3 | CH3 | - | - | 2-F | - | |
3.36 | A5 | - | - | - | CF3 | CH3 | - | - | 3-F | - | |
3.37 | A5 | - | - | - | CF3 | CH3 | - | - | 4-F | - | |
3.38 | A7 | - | - | - | - | - | CH3 | Cl | 2-F | - | |
3.39 | A7 | - | - | - | - | - | CH3 | Cl | 3-F | - |
序号 | A | R3 | R4 | R5 | R6 | R7 | R8 | R9 | R10 | X | 物理数据(℃) |
3.40 | A7 | - | - | - | - | - | CH3 | Cl | 4-F | - | |
3.41 | A7 | - | - | - | - | - | CF3 | Cl | 2-F | - | |
3.42 | A7 | - | - | - | - | - | CF3 | Cl | 4-F | - |
Claims (17)
1.一种控制有害真菌的组合物,在一种固体或液体载体中含有:a)至少一种活性成分I,其抑制细胞色素复合体III上的呼吸作用,和b)至少一种式II酰胺化合物
A-CO-NR1-R2 (II)其中A是芳基或含有1-3个选自O,N和S杂原子的芳香族或非芳香族5-元或6-元杂环;对于芳基或杂环来说,其可以是未取代的或者具有1,2或3个取代基,所述取代基各自独立地选自烷基,卤原子,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,烷基或烷氧基;R2是苯基或环烷基,其是未取代的或具有1-3个取代基,所述取代基各自独立地选自苯基,链烯基,炔基,链烯氧基,炔氧基,环烷基,环烯基,环烷基氧基和环烯基氧基,这些取代基另外可以被一个或几个卤原子取代,对于脂肪族或环脂族残基来说,其可以是部分或全部卤化的和/或对于环脂族残基来说,其可以被1-3个烷基取代,对于苯基来说,其可以具有1-5个卤原子和/或1-3个取代基,所述取代基各自独立地选自烷基,卤代烷基,烷氧基,卤代烷氧基,烷硫基和卤代烷硫基,对于酰胺化苯基来说,其可以与饱和的5-元环稠合,所述5-元环是未取代的或被一个或几个烷基取代的和/或可以具有一个选自O和S的杂原子,但不包括式II化合物,其中A是2-氯代吡啶-3-基,R1是H和R2是
2.权利要求1的组合物,其含有作为活性成分I的式IA或IB化合物其中…是双键或单键;
R′是-C[CO2CH3]=CHOCH3,-C[CO2CH3]=NOCH3,-C[CONHCH3]=NOCH3,
-C[CO2CH3]=CHCH3,-C[CO2CH3]=CHCH2CH3,-C[COCH3]=NOCH3,
-C[COCH2CH3]=NOCH3,-N(OCH3)-CO2CH3,-N(CH3)-CO2CH3或
-N(CH2CH3)-CO2CH3R”是直接键合的或通过氧键合的有机基团,巯基,氨基,或烷基氨基,或与基团X和它们所键合的环Q或T一起形成未取代的或取代的双环,其是部分或完全不饱和的体系,其成环原子除碳外,还可以含有1,2或3个独立地选自氧,硫和氮的杂原子;Rx 是-OC[CO2CH3]=CHOCH3,-OC[CO2CH3]=CHCH3,
-OC[CO2CH3]=CHCH2CH3,-SC[CO2CH3]=CHOCH3,-SC[CO2CH3]=CHCH3,
-SC[CO2CH3]=CHCH2CH3,-N(CH3)C[CO2CH3]=CHOCH3,
-N(CH3)C[CO2CH3]=NOCH3,-CH2C[CO2CH3]=CHOCH3,
-CH2C[CO2CH3]=NOCH3或-CH2C[CONHCH3]=NOCH3;Ry是氧,硫,=CH-或=N-;n是0,1,2或3,如果n>1,则基团X也可以是相同的或不同的;X是氰基,卤原子,烷基,卤代烷基,烷氧基,卤代烷氧基,烷硫基,或如果n>1,为C3-C5-亚-烷基,C3-C5-亚链烯基,氧代-C2-C4-亚烷基,氧代-C1-C3-亚烷基氧基,氧代-C2-C4-亚链烯基,氧代-C2-C4-亚链烯基氧基,或与苯环的两个相邻的碳原子键合的丁二烯二基,在这些链本身还可以与1-3个残基相连,所述残基各自独立地选自卤原子,烷基,卤代烷基,烷氧基,卤代烷氧基和烷硫基;Y是=C-或-N-;Q是苯基,吡咯基,噻吩基,呋喃基,吡唑基,咪唑基,噁唑基,异噁唑基,噻唑基,噻二唑基,三唑基,吡啶基,2-吡啶基,嘧啶基或三嗪基;和T是苯基,噁唑基,噻唑基,噻二唑基,噁二唑基,吡啶基,嘧啶基或三嗪基。
3.权利要求2的组合物,其含有作为活性成分I的一种式IA或IB化合物,其中R”是芳基氧基,杂芳基氧基,芳基氧基亚甲基,杂芳基氧基亚甲基,芳基亚乙烯基或杂芳基亚乙烯基,这些基团可以是为取代的或带有1,2或3个取代基,所述取代基各自独立地选自烷基,卤原子,CF3,CHF2,CN,烷氧基和苯基,这些取代基本身还可以带有1,2或3个各自独立地选自卤原子,CF3,CHF2,苯基,CN,苯氧基,烷基,烷氧基和卤代烷氧基的取代基;或者R”是CH2ON=CRαRβ或CH2ON=CRγCRδ=NORε,其中Rα是烷基;Rβ是未取代的或带有1,2或3个各自独立地选自烷基,烷氧基,卤原子,卤代烷氧基,CF3和CHF2取代基的苯基,吡啶基或嘧啶基;Rγ是烷基,烷氧基,卤原子,卤代烷基,或氢;Rδ是氢,氰基,卤原子,烷基,烷氧基,烷硫基,烷基氨基,二烷基氨基,链烯基,链烯基氧基,链烯基硫基,链烯基氨基,N-链烯基-N-烷基氨基,炔基,炔基氧基,炔硫基,炔基氨基,N-炔基-N-烷基氨基,这些基团中的烃基可以是部分或全部卤化的和/或与其连接有1,2或3个基团,所述基团各自独立地选自氰基,硝基,羟基,烷氧基,卤代烷氧基,烷氧基羰基,烷硫基,烷基氨基,二烷基氨基,链烯基氧基,环烷基,环烷基氧基,杂环基,杂环基氧基,芳基,芳基氧基,芳基烷氧基、杂芳基、杂芳氧基和杂芳烷氧基,所述环残基本身还可以是部分或全部卤化的和/或其上连接有1,2或3个基团,所述基团各自独立地选自氰基,硝基,羟基,烷基,卤代烷基,环烷基,烷氧基,卤代烷氧基,烷氧基羰基,烷硫基,烷基氨基,二烷基氨基,链烯基和链烯基氧基;或者是环烷基,环烷基氧基,环烷基硫基,环烷基氨基,N-环烷基-N-烷基氨基,杂环基,杂环基氧基,杂环基硫基,杂环基氨基,N-杂环基-N-烷基氨基,芳基,芳基氧基,芳基硫基,芳基氨基,N-芳基-N-烷基氨基,杂芳基,杂芳基氧基,杂芳基硫基,杂芳基氨基或N-杂芳基-N-烷基氨基,所述环残基可以是部分或全部卤化的和/或其上连接有1,2或3个基团,所述基团各自独立地选自氰基,硝基,羟基,烷基,卤代烷基,环烷基,烷氧基,卤代烷氧基,烷氧基羰基,烷硫基,烷基氨基,二烷基氨基,链烯基,链烯基氧基,苄基,苄基氧基,芳基,芳基氧基,杂芳基和杂芳基氧基,所述芳香族残基本身还可以是部分或全部卤化的和/或与其连接有1,2或3个氰基,烷基,卤代烷基,烷氧基,硝基基团;Rε是烷基,链烯基,或炔基,这些基团可以是部分或全部卤化的和/或其上连接有1,2或3个氰基,烷氧基,环烷基基团。
4.权利要求3的组合物,其含有作为活性成分I的式IA或IB化合物,其中R”是芳基氧基,杂芳基氧基,芳基氧基亚甲基,杂芳基氧基亚甲基,芳基亚乙烯基或杂芳基亚乙烯基,这些基团可以是未取代的或带有1,2或3个取代基,所述取代基各自独立地选自烷基,卤原子,CF3,CHF2,烷氧基和苯基,这些取代基本身还可以带有1,2或3个各自独立地选自卤原子,CF3,CHF2,苯基,CN和苯氧基的取代基;或者R”是CH2ON=CRαRβ或CH2ON=CRγCRδ=NORε,其中Rα是烷基;Rβ是未取代的或带有1,2或3个各自独立地选自烷基,烷氧基,卤原子,CF3和CHF2取代基的苯基或嘧啶基;Rγ是烷基;Rδ是烷基或苯基,其是未取代的或具有1,2,或3个各自独立地选自卤原子,CF3和CHF2的取代基;Rε是烷基。
5.权利要求3的组合物,其含有作为活性成分I的式IA化合物,其中R”具有下面定义之一:a)苯氧基亚甲基,吡啶基氧基亚甲基,嘧啶基氧基亚甲基或吡唑基氧基亚甲基,所述芳香基团可以是未取代的或带有1,2或3个取代基,所述取代基各自独立地选自烷基,卤原子,CF3,CHF2,-C(CH3)=NOCH3,和未取代的或被1,2或3个卤原子和/或烷基取代的苯基;b)苯氧基,或嘧啶基氧基,未取代的或被1,2或3个卤原子取代,或者未取代的或带有一个卤原子或氰基取代基的苯氧基;c)苯基亚乙烯基或吡唑基亚乙烯基,其中苯基或吡唑残基可以是未取代的或带有1,2或3个各自独立地选自卤原子,CF3,CHF2,和苯基的取代基;d)CH2ON=CRαRβ,其中Rα是烷基;和Rβ是未取代的或带有1,2或3个各自独立地选自烷基,卤原子,CF3,CHF2取代基的苯基,或者是未取代的或被1或2个烷氧基取代的嘧啶基;e)CH2ON=CRγCRδ=NORε其中Rγ是烷基,烷氧基,或卤原子;Rδ是烷基,氰基,卤原子,烷氧基,链烯基,或未取代的或被1,2或3个卤原子取代的苯基;和Rε是烷基。
6.权利要求2-5中任一项的组合物,其中R’是C[CO2CH3]=CHCH3或C[CONHCH3]=NOCH3。
7.权利要求2-6中任一项的组合物,其含有作为活性成分I的式IA化合物,其中Q是苯基且n是0。
9.前面权利要求中任一项的组合物,其含有作为酰胺化合物的式II化合物,其中残基A是下面的基团之一:苯基,吡啶基,二氢吡喃基,二氢氧硫杂环己二烯基,二氢氧硫杂环己二烯基氧化物,二氢氧硫杂环己二烯基二氧化物,呋喃基,噻唑基,吡唑基,或噁唑基,这些取代基可以带有1,2或3个各自独立地选自烷基,卤原子,二氟甲基,和三氟甲基的取代基。
10.权利要求1-8中任一项的组合物,其中含有作为酰胺化合物的式II化合物,其中A是下述基团之一:吡啶-3-基,其是未取代的或在2-位被卤原子,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,其是未取代的或在2-位被甲基,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,其是未取代的或在4-和/或5-位被甲基取代;噻唑-5-基,其是未取代的或在2-和/或4-位被甲基,氯,二氟甲基或三氟甲基取代;噻唑-4-基,其是未取代的或在2-和/或5-位被甲基,氯,二氟甲基或三氟甲基取代;1-甲基吡唑-4-基,其是未取代的或在3-和/或5-位被甲基,氯,二氟甲基或三氟甲基取代;或噁唑-5-基,其是未取代的或在2-和/或4-位被甲基或氯取代。
11.前面权利要求中任一项的组合物,其含有作为酰胺化合物的一种式II化合物,其中R2是未取代的或被1,2或3个在权利要求1所述取代基取代的苯基。
12.权利要求11的组合物,其中R2是在2-位具有下述取代基之一的苯基:C5-C6-环烯基,C5-C6-环烷基氧基,C5-C6-环烯基氧基,这些基团可以被1,2或3个C1-C4-烷基取代,苯基,其被1-5个卤原子和/或1-3个各自独立地选自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-卤代烷硫基的基团取代。
16.前面权利要求中任一项的组合物,它含有两部分,一部分是在一种固体或液体中含有活性成分I,而另一部分是在一种固体或液体载体中含有式II酰胺化合物。
17.一种控制有害真菌的方法,包括用权利要求1-16中任一项的组合物处理真菌,其环境,或待保护使之不受真菌侵害的材料,植物,种子,土壤,表面或空间,可以同时即共同地,或分开地,或依次施用活性成分。
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1650707B (zh) * | 1997-12-18 | 2010-06-16 | 巴斯福股份公司 | 基于酰胺化合物和吡啶衍生物的杀真菌混合物 |
CN101232808B (zh) * | 2005-07-28 | 2012-09-05 | 拜尔农作物科学股份公司 | 含一种甲酰胺、一种吡咯、另一种吡咯或一种甲氧基丙烯酸酯的具有协同杀菌活性的物质结合物 |
CN106397422A (zh) * | 2016-08-29 | 2017-02-15 | 南京农业大学 | 含手性噁唑啉的烟酰胺类化合物及作为农用杀菌剂的用途 |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19615977A1 (de) * | 1996-04-22 | 1997-10-23 | Basf Ag | Mittel und Verfahren zur Bekämpfung von Schadpilzen |
DE59706890D1 (de) * | 1996-08-30 | 2002-05-08 | Basf Ag | Fungizide mischungen |
NZ335147A (en) * | 1996-10-17 | 2000-09-29 | Basf Ag | Method for controlling parasitic fungi in cultivated plants |
GB9718366D0 (en) * | 1997-08-29 | 1997-11-05 | Ciba Geigy Ag | Novel combinations |
UA68368C2 (en) * | 1997-12-18 | 2004-08-16 | Basf Ag | Fungicidal mixture based on amide compounds and pyridine derivatives |
CA2313332C (en) * | 1997-12-18 | 2008-04-22 | Basf Aktiengesellschaft | Fungicide mixtures based on pyridine amides and morpholine derivatives or piperidine derivatives |
ATE225602T1 (de) * | 1997-12-18 | 2002-10-15 | Basf Ag | Fungizide mischungen auf der basis von pyridincarboxamiden |
TW450788B (en) * | 1997-12-18 | 2001-08-21 | Basf Ag | Fungicidal mixtures based on amide compounds and benzimidazoles or precursors which release them |
SK285473B6 (sk) * | 1997-12-18 | 2007-02-01 | Basf Aktiengesellschaft | Fungicídne zmesi na báze amidových zlúčenín a spôsob ničenia škodlivých húb |
ATE239372T1 (de) | 1997-12-18 | 2003-05-15 | Basf Ag | Fungizide mischungen auf der basis von pyridinamiden und fenarimol |
TW491686B (en) * | 1997-12-18 | 2002-06-21 | Basf Ag | Fungicidal mixtures based on amide compounds and tetrachloroisophthalonitrile |
UA70327C2 (uk) * | 1998-06-08 | 2004-10-15 | Баєр Акціенгезельшафт | Спосіб боротьби з фітопатогенними хворобами сільськогосподарських рослин та фунгіцидна композиція |
DE10063046A1 (de) | 2000-12-18 | 2002-06-20 | Basf Ag | Fungizide Mischungen |
BR0206442A (pt) * | 2001-01-16 | 2003-12-30 | Basf Ag | Misturas fungicidas, método para combater fungos nocivos, e, agente fungicida |
IL156502A0 (en) * | 2001-01-18 | 2004-01-04 | Basf Ag | Fungicidal mixtures from benzophenones and n-biphenyl nicotinamides |
RS20050357A (en) | 2002-11-15 | 2007-11-15 | Basf Aktiengesellschaft, | Fungicidal mixtures |
BRPI0413640B1 (pt) * | 2003-08-26 | 2015-07-21 | Basf Ag | Método para o tratamento de plantas necessitando de promoção de crescimento |
DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
UA81731C2 (ru) * | 2004-05-13 | 2008-01-25 | Basf Ag | Фунгицидная смесь для борьбы с патогенными грибами и средство, способ борьбы, посевной материал, применение соединений в смеси |
GB0418047D0 (en) | 2004-08-12 | 2004-09-15 | Syngenta Participations Ag | Fungicidal compositions |
GB0422401D0 (en) * | 2004-10-08 | 2004-11-10 | Syngenta Participations Ag | Fungicidal compositions |
GB0422399D0 (en) * | 2004-10-08 | 2004-11-10 | Syngenta Participations Ag | Fungicidal compositions |
GB0422400D0 (en) * | 2004-10-08 | 2004-11-10 | Syngenta Participations Ag | Fungicidal compositions |
PE20070409A1 (es) * | 2005-06-29 | 2007-05-07 | Basf Ag | Mezclas fungicidas con base en bifenilamidas de acido pirazolcarboxilico disustituidas en 2,4 |
US20090239748A1 (en) * | 2005-06-30 | 2009-09-24 | Basf Aktiengesellschaft | Fungicidal Mixtures Based on 2,5-Disubstituted N-Biphenylpyrazolcarboxamides |
US20090042725A1 (en) * | 2005-07-01 | 2009-02-12 | Basf Aktiengesellschaft | Fungicidal Mixtures Based on 3,5-Disubstituted N-Biphenyl-Pyrazolcarboxamides |
BRPI0612804A2 (pt) * | 2005-07-01 | 2016-11-29 | Basf Ag | misturas fungicidas para combater fungos nocivos fitopatogênicos, agente fungicida, processo para combater fungos nocivos fitopatogênicos, semente, e, uso dos compostos |
BRPI0612733A2 (pt) * | 2005-07-06 | 2010-11-30 | Basf Ag | misturas fungicidas para combater fungos nocivos fitopatogênicos, agente, processo para combater fungos nocivos fitopatogênicos, semente, e uso dos compostos |
CN104604873A (zh) * | 2005-08-05 | 2015-05-13 | 巴斯夫欧洲公司 | 包含取代的1-甲基吡唑-4-基甲酰苯胺的杀真菌混合物 |
PL383990A1 (pl) | 2007-12-07 | 2009-06-08 | Stanisław Rogut | Sposób i układ przetwarzania odpadów, zwłaszcza komunalnych, oraz komponenty paliwa energetycznego |
US8770137B2 (en) * | 2012-01-09 | 2014-07-08 | Jing Nan Traffic Engineering Co., Ltd. | Structure of traffic cone |
US9120259B2 (en) * | 2013-04-15 | 2015-09-01 | Jing Nan Traffic Engineering Co., Ltd. | Counterweight structure of a traffic cone |
EP3047731A1 (en) | 2015-01-21 | 2016-07-27 | Basf Se | Method for combating soybean rust comprising treating soybean with (2E)-2-[3-substituted-2 [[(E)-[(2E)-2-alkoxyimino-1-methyl-2-phenyl-ethylidene]amino]oxymethyl]phenyl]-2-methoxy-imino-N-methyl-acetamides |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3623921A1 (de) | 1986-07-16 | 1988-01-21 | Basf Ag | Oximether und diese enthaltende fungizide |
GB8617648D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Fungicides |
GB8903019D0 (en) * | 1989-02-10 | 1989-03-30 | Ici Plc | Fungicides |
EP0394631A3 (en) * | 1989-04-25 | 1991-07-31 | Nissan Chemical Industries Ltd. | Composition of fungicide for agricultural and horticultural use |
CA2081935C (en) | 1991-11-22 | 2004-05-25 | Karl Eicken | Anilide derivatives and their use for combating botrytis |
US5223526A (en) | 1991-12-06 | 1993-06-29 | Monsanto Company | Pyrazole carboxanilide fungicides and use |
DE4231517A1 (de) | 1992-09-21 | 1994-03-24 | Basf Ag | Carbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
FR2711040B1 (fr) * | 1993-10-14 | 1996-09-06 | Rhone Poulenc Agrochimie | Associations fongicides à base d'un phénylbenzamide. |
TW305743B (zh) * | 1993-11-04 | 1997-05-21 | Sumitomo Chemical Co | |
JP3349566B2 (ja) * | 1993-11-25 | 2002-11-25 | 日本バイエルアグロケム株式会社 | 農園芸用殺菌剤組成物 |
ES2172575T3 (es) * | 1993-12-02 | 2002-10-01 | Sumitomo Chemical Co | Composicion bactericida. |
JPH07304607A (ja) * | 1994-05-13 | 1995-11-21 | Sumitomo Chem Co Ltd | 殺菌剤組成物 |
JPH07330516A (ja) * | 1994-06-08 | 1995-12-19 | Sumitomo Chem Co Ltd | 殺菌剤組成物 |
JP3470399B2 (ja) * | 1994-07-14 | 2003-11-25 | 住友化学工業株式会社 | 殺菌剤組成物 |
AU688540B2 (en) * | 1994-07-21 | 1998-03-12 | Basf Aktiengesellschaft | Method of combating harmful fungi |
-
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1650707B (zh) * | 1997-12-18 | 2010-06-16 | 巴斯福股份公司 | 基于酰胺化合物和吡啶衍生物的杀真菌混合物 |
CN101232808B (zh) * | 2005-07-28 | 2012-09-05 | 拜尔农作物科学股份公司 | 含一种甲酰胺、一种吡咯、另一种吡咯或一种甲氧基丙烯酸酯的具有协同杀菌活性的物质结合物 |
CN106397422A (zh) * | 2016-08-29 | 2017-02-15 | 南京农业大学 | 含手性噁唑啉的烟酰胺类化合物及作为农用杀菌剂的用途 |
CN106397422B (zh) * | 2016-08-29 | 2018-06-08 | 南京农业大学 | 含手性噁唑啉的烟酰胺类化合物及作为农用杀菌剂的用途 |
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