CN1282209A - 基于吡啶酰胺和吗啉或哌啶衍生物的杀真菌混合物 - Google Patents
基于吡啶酰胺和吗啉或哌啶衍生物的杀真菌混合物 Download PDFInfo
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- CN1282209A CN1282209A CN98812309A CN98812309A CN1282209A CN 1282209 A CN1282209 A CN 1282209A CN 98812309 A CN98812309 A CN 98812309A CN 98812309 A CN98812309 A CN 98812309A CN 1282209 A CN1282209 A CN 1282209A
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- Prior art keywords
- methyl
- alkyl
- group
- phenyl
- halogen
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 34
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Abstract
本发明提供了一种杀真菌混合物,其中包含增效有效量的以下物质作为活性组分:a)式(Ⅰ)A-CO-NR1R2的酰胺化合物,其中A是芳基或具有1至3个选自O、N和S的杂原子的芳族或非芳族、5或6元杂环基;这里芳基或杂环基具有或不具有1、2或3个相互独立地选自烷基、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的取代基;R1是氢原子;R2是苯基或环烷基,它们具有或不具有1、2或3个相互独立地选自烷基、链烯基、炔基、烷氧基、链烯氧基、炔氧基、环烷基、环烯基、环烷氧基、环烯基氧基、苯基和卤素的取代基,其中脂族和环脂族基因可以部分或完全被卤代和/或环脂族基团可以被1至3个烷基取代,在此苯基可具有1至5个卤原子和/或1至3个相互独立地选自烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基和卤代烷硫基的取代基,和其中酰胺的苯基可以与可以被一个或多个烷基取代和/或可具有一个选自O和S的杂原子的饱和五元环稠合,和b)选自化合物(Ⅱa)、(Ⅱb)、(Ⅱc)、(Ⅱd)和(Ⅱe)的吗啉或哌啶衍生物(Ⅲ)。
Description
本发明涉及防治有害真菌的杀真菌混合物以及使用该混合物防治有害真菌的方法。
WO 97/08952描述了式(Ⅰ)酰胺化合物和作为杀螨剂的活性成分喹螨醚的混合物,所描述的混合物可特别有效地防治葡萄孢(Botrytis),A-CO-NR1R2 (Ⅰ)其中A是芳基或具有1至3个选自O、N和S的杂原子的芳族或非芳族、5或6元杂环基;这里芳基或杂环基具有或不具有1、2或3个相互独立地选自烷基、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的取代基;R1是氢原子;R2是苯基或环烷基,它们具有或不具有1、2或3个相互独立地选自烷基、链烯基、炔基、烷氧基、链烯氧基、炔氧基、环烷基、环烯基、环烷氧基、环烯基氧基、苯基和卤素的取代基,其中脂族和环脂族基团可以部分或完全被卤代和/或环脂族基团可以被1至3个烷基取代,和其中苯基可具有1至5个卤原子和/或1至3个相互独立地选自烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基和卤代烷硫基的取代基,和其中酰胺的苯基可以与可以被一个或多个烷基取代和/或可具有一个选自O和S的杂原子的饱和五元环稠合。
由EP-A 797386、WO 97/06681、EP-B 425857、EP-B 524496、EP-A 690792、WO 94/22308和EP-B 645087已知其它含式Ⅱa至Ⅱc的活性成分的杀真菌混合物。
本发明的目的是提供防治有害真菌和特别地对某些病症特别有效的其它混合物。
令人惊奇地发现,本发明的目的可由包含本文开头定义的式Ⅰ的酰胺化合物作为活性成分和选自式Ⅱa至Ⅱc的吗啉和哌啶杀真菌活性成分作为其它杀真菌活性组分的混合物得以实现。[n=10,11,12(60·70%)或13]
本发明的混合物具有增效作用,因此特别适合于防治有害真菌,特别是粉霉病(powdery mildew)菌。
在本发明中卤素是氟、氯、溴和碘,特别是氟、氯和溴。
术语“烷基”包含直链或支链烷基。优选是直链或支链C1-C12-烷基,特别是C1-C6-烷基。烷基的实例是甲基、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多个卤原子,特别是氟和氯,部分或全部卤化的上述烷基基团。优选存在1至3个卤原子,其中二氟甲基和三氟甲基是特别优选的。
上述对烷基基团和卤代烷基基团的说明相应地也适合于烷氧基、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。
链烯基包含直链或支链链烯基。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-3-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-丙烯基或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多个卤原子,特别是氟或氯,部分或全部卤化。链烯基优选具有1至3个卤原子。
炔基包含直链或支链炔基。优选直链或支链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。
上述对链烯基和其卤素取代基以及炔基的说明相应地也适用于链烯氧基和炔氧基。
环烷基优选是C3-C6-环烷基,例如环丙基、环丁基、环戊基和环己基。如果环烷基是被取代的,那么优选具有1至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。如果环烯基是被取代的,那么优选包含1至3个C1-C4-烷基作为取代基。
环烷氧基优选是C5-C6-环烷氧基,例如环戊氧基或环己氧基。如果环烷氧基是被取代的,那么优选包含1至3个C1-C4-烷作为取代基。
环烯氧基优选是C5-C6-环烯氧基,例如环戊氧基或环己氧基。如果环烯氧基是被取代的,那么优选包含1至3个C1-C4-烷基作为取代基。
芳基优选是苯基。
如果A是苯基,那么它可以在任何位置具有1、2或3个上述取代基。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。优选苯基在2-位上具有取代基。
如果A是5元杂环基,那么优选是呋喃基、噻唑基、吡唑基、咪唑基、噁唑基、噻吩基、***基或噻二唑基或者其相应的二氢或四氢衍生物。优选是噻唑基或吡唑基。
6元芳族杂环基特别优选是吡啶基,特别是3-吡啶基,或下式基团:其中X是CH2、S、SO或SO2。
上述杂环基具有或不具有1、2或3个上述取代基,优选这些取代基相互独立地选自烷基、卤素、二氟甲基和三氟甲基。
A特别优选是下式基团: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,特别是氯,CHF2或CF3。
式Ⅰ中的基团R1优选是氢原子。
式Ⅰ中的基团R2优选是苯基。R2优选具有至少一个取代基,取代基特别优选是在2位上。取代基优选选自烷基、环烷基、环烯基、卤素和苯基。
基团R2的取代基本身可以再次被取代。脂族或环脂族取代基可以部分或完全被卤化,特别是氟化或氯化。它们优选具有1、2或3个氟或氯原子。如果基团R2的取代基是苯基,该苯基基团可优选被1至3个卤原子,特别是氯原子取代,和/或被优选选自烷基和烷氧基的基团取代。特别优选地,苯基在对位上被卤原子取代,即基团R2的特别优选的取代基是对卤素取代的苯基。基团R2也可以与饱和的5元环稠合,这里该环本身可具有1至3个烷基取代基。
在这种情况下,R2例如是2,3-二氢化茚基、苯并二氢噻吩基和氧杂2,3-二氢化茚基(Oxaindanyl)。优选特别是经4位与氮原子连接的2,3-二氢化茚基和2-氧杂2,3-二氢化茚基。
根据优选的实施方案,本发明组合物包含其中A的含义如下定义的式Ⅰ化合物作为酰胺化合物:
苯基、吡啶基、二氢吡喃基、二氢氧硫杂环己二烯基、氧化二氢氧硫杂环己二烯基(Dihydrooxathiinyloxid)、二氧化二氢氧硫杂环己二烯基(Dihydrooxathiinyldioxid)、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
吡啶-3-基,其可以在2位上被卤素、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或未取代;
苯基,其可以在2位上被甲基、三氟甲基、氯、溴或碘取代或未取代;
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,其可以在4-位和/或5-位上被甲基取代或未取代;
噻唑-5-基,其可以在2-位和/或4-位上被甲基、氯、二氟甲基或三氟甲基取代或未取代;
噻唑-4-基,其可以在2-位和/或5-位上被甲基、氯、二氟甲基或三氟甲基取代或未取代;
1-甲基吡唑-4-基,其可以在3-位和/或5-位上被甲基、氯、二氟甲基或三氟甲基取代或未取代;或
噁唑-5-基,其可以在2-位和/或4-位上被甲基或氯取代或未取代。
根据另一优选实施方案,本发明的组合物包含其中R2是被1,2或3个上述取代基取代或未取代的苯基的式Ⅰ化合物作为酰胺化合物。
根据又一优选的实施方案,本发明的组合物包含其中R2是在2-位上具有下列取代基之一的苯基的式Ⅰ化合物作为酰胺化合物:
C3-C6-烷基、C5-C6-环烯基、C5-C6-环烷氧基、环烯基氧基,其中这些基团可以被1、2或3个C1-C4-烷基取代,
苯基,其可以被1至5个卤原子和/或1至3个相互独立地选自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,
2,3-二氢化茚基或氧杂2,3-二氢化茚基,其可以被1、2或3个C1-C4-烷基取代。
根据另一优选实施方案,本发明组合物包含下式Ⅰa化合物作为酰胺化合物,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。
可使用的式Ⅰ酰胺化合物是在EP-A-545 099和589 301中提及的,它们再此全文引入以供参考。
式Ⅰ酰胺化合物的制备方法是已知的,例如由EP-A-545 099或589301中公开,或者可以类似方法制备。
吗啉和哌啶衍生物Ⅱ、其制备方法和其抗有害真菌的作用同样是已知的(Ⅱa:通用名:丁苯吗啉,US-A4,202,894;Ⅱb:通用名:苯锈啶,US-A 4,202,894;Ⅱc:通用名:十三吗啉,DE-A 1164152)。
少量的式Ⅰ酰胺化合物便足以达到增效作用。优选酰胺化合物和吗啉或哌啶衍生物以20∶1-1∶20,优选10∶1-1∶10的重量比使用。
由于化合物Ⅱ的氮原子的碱性特征而能够与无机或有机酸或与金属离子形成盐或加合物。
无机酸的例子为氢卤酸,例如氢氟酸、氢氯酸、氢溴酸和氢碘酸、以及硫酸、磷酸和硝酸。
合适的有机酸为,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(含有1-20个碳原子的直链或支链烷基磺酸),芳基磺酸或芳基二磺酸(其上连接有一个或两个磺基的芳基,如苯基和萘基)、烷基膦酸(具有1-20个碳原子的直链或支链烷基膦酸)、芳基膦酸或芳基二膦酸(其上连接有一个或两个磷酸基团的芳基,如苯基和萘基),其中烷基或芳基还可携带其它取代基,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。
适当的金属离子尤为下列各族元素的离子:第一到第八副族元素(特别是铬、锰、铁、钴、镍、铜、锌),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)。这些金属可以是所能具有的各种价态。
在制备混合物时,优选采用纯活性成分Ⅰ和Ⅱ,其中可以根据需要混入对有害真菌或其它害虫(如昆虫,蛛形纲动物或线虫)具有活性的其它成份,或具有除草活性或植物生长调节活性的成份或肥料。
化合物Ⅰ与Ⅱ的混合物,或同时一起或分别使用化合物Ⅰ和Ⅱ,表现出对广谱的植物病原真菌,特别是属于子囊菌纲、担子菌纲、半知菌纲和藻状菌纲的真菌的优异活性。这些化合物中某些内吸地起作用,因而可用作叶面和土壤杀真菌剂。
它们对于防治各种作物,如棉花、蔬菜类(如黄瓜,菜豆,番茄,马铃薯和葫芦科)、大麦、牧草、燕麦、香蕉、咖啡、玉米、水果类、稻、黑麦、大豆、葡萄、小麦、观赏植物,甘蔗以及各种种子上的许多真菌特别重要。
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)(echter Mehltau)、葫芦科上的二孢白粉菌(Erysiphe cichoracearum)和苍耳单丝壳菌(Sphaerothecafulginea)、苹果上的苹果白粉病菌(Podosphaera leucotricha)、葡萄上的葡萄钩丝壳(Uncinula necator),禾谷类上的柄锈菌(Puccinia)、棉花、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(Schorf)(Venturiainaequalis)、禾谷类上的长蠕孢菌(Helminthosporium)、小麦上的颖枯病菌(Septoria nodorum)、草莓、蔬菜、观赏植物和葡萄上的灰葡萄孢(Botrytis cinera)(Grauschimmel)、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(Pyriculariaoryzae)、马铃薯和蕃茄上的致病疫霉(Phytophthora infestans)、葡萄上的葡萄生单轴霉(Plasmopara viticola)、啤酒花和黄瓜上的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)。
而且,它们可用于保护材料(如,保护木材)免遭例如宛氏拟青霉(Paecilomyces variotii)的侵害。
本发明的混合物特别优选地可用于防治葡萄和禾谷类作物上的粉霉病(powdery mildew)菌。
化合物Ⅰ与Ⅱ可以同时,即,一起或分别施用,或先后施用,在分别施用的情形下,其施用次序一般对防治结果没有任何影响。
本发明混合物的施用量,特别是在大田农作物的情况下,一般为0.01-8kg/ha,优选0.1-5kg/ha,尤为0.2-3.0kg/ha,这取决于所希望的效果。
化合物Ⅰ的施用量为0.01-2.5kg/ha,优选0.05-2.5kg/ha,特别是0.1-1.0kg/ha。
相应地,就化合物Ⅱ来说,施用量一般为0.01-10kg/ha,优选0.05-5kg/ha,特别是0.05-2.0kg/ha。
对于种子的处理,该混合物的施用量一般为0.001-250克/kg种子,优选0.01-100克/kg,特别是0.01-50克/kg。
如果要防治植物病原有害真菌,化合物Ⅰ与Ⅱ的一起或分别施用或化合物Ⅰ与Ⅱ的混合物的施用可在植物播种之前或之后,或者在植物发芽之前或之后,通过对种子、植物或土壤喷雾或撒粉来进行。
本发明的杀真菌增效混合物,或化合物Ⅰ和Ⅱ可以配制成,例如即可喷雾的溶液、粉剂和悬浮液形式,或高浓度的水性、油性或其它悬浮液、分散液、乳液,油分散体、糊剂、喷粉剂、撒播剂或颗粒剂的形式,并通过喷雾、弥雾、撒粉、撒播或浇泼使用。施用形式主要取决于预定用途;在任何情况下,应确保本发明混合物尽可能细微和均匀地分散。
这些制剂以本身已知的方式,例如通过活性化合物与溶剂和/或载体混合,如果需要,通过使用乳化剂和分散剂来制备。如果所使用的稀释剂是水,也可以用其它的有机溶剂作助溶剂。对此适合的辅助剂主要是溶剂,如芳族化合物(例如二甲苯)、氯代芳族化合物(例如氯苯)、石蜡(例如石油馏份)、醇类(例如甲醇、丁醇)、酮类(例如环己酮)、胺类(例如乙醇胺、二甲基甲酰胺)和水;载体如研碎的天然矿物质(例如高岭土、矾土、滑石、白垩)和研碎的合成矿物质(例如细分散的硅酸、硅酸盐);乳化剂如非离子和阴离子乳化剂(例如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)和分散剂如木质素亚硫酸盐废液或甲基纤维素。
合适的表面活性物质为下列酸的碱金属盐、碱土金属盐和铵盐:芳族磺酸,如木质素磺酸、苯酚磺酸、萘磺酸和二丁基萘磺酸,和脂肪酸、烷基-和烷芳基磺酸,烷基-、月桂基醚-和脂肪醇硫酸;以及硫酸化十六烷基醇、十七烷基醇和十八烷基醇或脂肪醇乙二醇醚的盐,磺化萘及其衍生物与甲醛的缩合产物,萘或萘磺酸与苯酚和甲醛的缩合产物,聚氧乙烯辛基苯酚醚,乙氧基化异辛基苯酚、辛基苯酚或壬基苯酚,烷基苯酚聚乙二醇醚或三丁基苯基聚乙二醇醚,烷芳基聚醚醇,异十三烷基醇、脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚或聚氧丙烯(原文如此),十二烷基醇聚乙二醇醚乙酸盐,山梨醇酯,木素亚硫酸盐废液或甲基纤维素。
粉剂、撒播剂和喷粉剂可通过混合或一同研磨化合物Ⅰ或Ⅱ或化合物Ⅰ和Ⅱ的混合物与固体载体来制备。
颗粒剂(例如,包衣颗粒,浸渍颗粒和均质颗粒)通常通过将活性成分粘合到固体载体上来制备。
填料或固体载体是,例如矿质土类,如硅胶、硅酸、硅石、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、研碎的合成物质、和肥料,如硫酸铵、磷酸铵、硝酸铵、尿素,以及植物源产物,如谷类作物粉末、树皮粉末、木材粉末和坚果壳粉,纤维素粉末或其它固体载体。
制剂通常包含0.1-95%重量,优选0.5-90%重量的化合物Ⅰ或Ⅱ之一或化合物Ⅰ与Ⅱ的混合物。所用活性成分的纯度为90%-100%,优选95%-100%(根据NMR谱或HPLC测定)。
化合物Ⅰ或Ⅱ或其混合物或相应制剂通过用杀真菌有效量的混合物,或(在分别施用情形下)化合物Ⅰ和Ⅱ处理有害真菌、其聚集地、或欲免受它们侵染的植物、种子、土壤、表面,材料或空间的方式施用。
施用可在有害真菌侵染前或侵染后进行。
含有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,该溶液适合以微小雾滴的形式使用。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-单乙醇酰胺的加成物、5重量份的十二烷基苯磺酸钙盐和5重量份的40摩尔环氧乙烷与1摩尔蓖麻油的加成物的混合物;将该溶液细分散在水中获得分散液。Ⅲ.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摩尔蓖麻油的加成物组成的水分散液。Ⅳ.20重量份的活性成分、25重量份的环己醇、65重量份沸点是210至280℃的石油馏份和10重量份40摩尔环氧乙烷与1摩尔蓖麻油的加成物组成的水分散液。Ⅴ.将80重量份的活性成分与3重量份的二异丁基萘-1-磺酸钠盐、10重量份的来源于亚硫酸盐废液的木素磺酸钠盐和7重量份的粉状硅胶混合,且在锤磨中磨碎混合物,通过将该混合物细分散在水中获得喷雾混合物;Ⅵ.将3重量份的活性成分与97重量份的细粉碎的高岭土均匀混合,由此获得喷粉剂,它包含3重量%的活性成分。Ⅶ.30重量份的活性成分、92重量份的粉状的硅胶和8重量份预先喷涂到硅胶表面上的石蜡油组成的均匀混合物;得到具有良好粘性的活性成分的制剂。Ⅷ.40重量份的活性成分、10重量份的苯酚磺酸/脲/甲醛缩合物的钠盐、2重量份硅胶和48重量份水组成的稳定的水分散液,该分散液可以进一步稀释;Ⅸ、20重量份的活性成分、2重量份的十二烷基苯磺酸钙、8重量份的脂肪醇聚乙二醇醚、20重量份的苯酚磺酸/脲/甲醛缩合物的钠盐和88重量份的石蜡矿物油组成的稳定油性分散液。
应用实施例
本发明混合物的增效作用可以通过下面的试验来证明:
将活性成分(单独或一起)配制成在63%重量环己酮与27%重量乳化剂组成的混合物中的10%乳液,然后用水稀释至所需浓度。
通过测定感染叶面面积的百分数进行评价。将这些百分数换算成作用效力。作用效力(W)采用下述Abbot公式计算:
W=(1-α)·100/βα对应于处理植物的真菌感染,以%计,和β对应于未处理(对照组)植物的真菌感染,以%计
效力0表示处理植物的感染程度与未处理对照植物感染程度相当;效力100表示处理植物未被感染。
采用Colby公式[R.S.Colby,杂草(Weeds),15,20-22(1967)]计算活性成分混合物的预期作用效力并与观测到的作用效力加以比较。
Colby公式:E=x+y-x·y/100E表示使用浓度分别为a和b的活性成分A和B的混合物的情况下的预期作用效力,以未处理对照组的%表示X表示使用浓度为a的活性成分A的情况下的作用效力,以未处理对照组的%表示Y表示使用浓度为b的活性成分B的情况下的作用效力,以未处理对照组的%表示。
应用实施例1-抗小麦上的隐匿柄锈菌活性
用隐匿柄锈菌(Puccinia recondita)孢子喷洒盆栽小麦秧苗(栽培品种“Kanzler”)的叶片。然后将该盆在高湿度(90至95%)和20-22℃的培养室中放置24小时。在这期间,该孢子萌发,并且萌发管侵入叶片组织。第二天,使用由包含10%活性成分、63%环己酮和27%乳化剂的储备溶液制备的含水悬浮液喷雾感染的植物至滴流。在喷雾液层干燥之后,将试验植物在20至22℃和65至70%相对大气湿度下的温室中温育7天。之后测定叶片上柄锈菌的感染程度。
所使用的式Ⅰ化合物是下列组分: 结果列于下表1和2中。表1
表2
*)采用Colby公式计算
实施例 | 活性成分(含量以ppm计) | 活性成分在喷雾液中的浓度(ppm) | 以未处理对照组的%表示的作用效力 |
1V | 对照组(未处理) | (100%感染) | 0 |
2V | 化合物1.1 | 6316 | 00 |
3V | 化合物1.2 | 16 | 0 |
4V | 化合物11a | 16 | 20 |
5V | 化合物11b | 16 | 20 |
6V | 化合物11c | 63 | 0 |
实施例 | 按照本发明的混合物(含量以ppm计) | 所观察到的作用效力 | 计算出的作用效力*) |
7 | 16 ppmⅠ.1+16 ppm Ⅱa | 50 | 20 |
8 | 16 ppmⅠ.1+16 ppm Ⅱb | 40 | 20 |
9 | 63 ppmⅠ.1+63 ppm Ⅱc | 25 | 0 |
10 | 16 ppmⅠ.2+16 ppm Ⅱ.a | 50 | 20 |
11 | 16 ppmⅠ.216 ppm Ⅱ.b | 45 | 20 |
试验结果表明,对于所有的混合比例,所观察的效力均超过采用Colby公式计算的效力。
应用实施例2-抗小麦白粉菌的活性
使用由包含10%活性成分、63%环己酮和27%乳化剂的储备溶液制备的含水悬浮液喷雾盆栽小麦秧苗(栽培品种“Kanzler”)的叶片至滴流。在喷雾液层干燥之后24小时,用小麦白粉菌(Erysiphegraminis forma specialis tritici)孢子喷洒叶片。随后将试验植物放置在20至24℃和60至90%相对大气湿度下的温室中。7天之后,目测评价总叶面上白粉菌的感染程度(以%计)。
试验结果列于表3和4中。表3
表4
*)采用Colby公式计算
实施例 | 活性成分(含量以ppn计) | 活性成分在喷雾液中的浓度(ppm) | 以未处理对照组的%表示的作用效力 |
12V | 对照组(未处理) | 0(100%感染) | 0 |
13V | 化合物1.1 | 164 | 00 |
14V | 化合物1.2 | 41 | 00 |
15V | 化合物11a | 41 | 200 |
16V | 化合物11b | 41 | 300 |
17V | 化合物11c | 164 | 200 |
实施例 | 按照本发明的混合物(含量以ppm计) | 所观察到的作用效力 | 计算出的作用效力*) |
18 | 4 ppmⅠ.1+4 ppm Ⅱa | 40 | 20 |
19 | 4 ppmⅠ.1+4 ppm Ⅱ.b | 45 | 30 |
20 | 16 ppmⅠ.1+16 ppm Ⅱc | 35 | 20 |
21 | 4 ppmⅠ.2+4 ppm Ⅱa | 70 | 20 |
22 | 1 ppmⅠ.2+1 ppm Ⅱa | 20 | 0 |
23 | 1 ppmⅠ.2+1 ppm Ⅱc | 25 | 0 |
试验结果表明,对于所有的混合比例,所观察的效力均超过采用Colby公式计算的效力。
Claims (10)
1.一种杀真菌混合物,其中包含增效有效量的以下物质作为活性组分:a)式Ⅰ的酰胺化合物A-CO-NR1R2 (Ⅰ)其中A是芳基或具有1至3个选自O、N和S的杂原子的芳族或非芳族、5或6元杂环基;这里芳基或杂环基具有或不具有1、2或3个相互独立地选自烷基、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的取代基;R1 是氢原子;R2 是苯基或环烷基,它们具有或不具有1、2或3个相互独立地选自烷基、链烯基、炔基、烷氧基、链烯氧基、炔氧基、环烷基、环烯基、环烷氧基、环烯基氧基、苯基和卤素的取代基,其中脂族和环脂族基团可以部分或完全被卤代和/或环脂族基团可以被1至3个烷基取代,和其中苯基可具有1至5个卤原子和/或1至3个相互独立地选自烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基和卤代烷硫基的取代基,和其中酰胺的苯基任选地与可以被一个或多个烷基取代和/或可具有一个选自O和S的杂原子的饱和五元环稠合,和b)选自化合物Ⅱa、Ⅱb和Ⅱc的吗啉或哌啶衍生物Ⅱ [n=10,11,12(60·70%)或13]
2.权利要求1的杀真菌混合物,其中式Ⅰ中的基团A是下列基团之一:
苯基、吡啶基、二氢吡喃基、二氢氧硫杂环己二烯基、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。
3.权利要求1所要求的杀真菌混合物,其中式I中的基团A是下列基团之一:
吡啶-3-基,其可以在2位上被卤素、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或未取代;
苯基,其可以在2位上被甲基、三氟甲基、氯、溴或碘取代或未取代;
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,其可以在4-位和/或5-位上被甲基取代或未取代;
噻唑-5-基,其可以在2-位和/或4-位上被甲基、氯、二氟甲基或三氟甲基取代或未取代;
噻唑-4-基,其可以在2-位和/或5-位上被甲基、氯、二氟甲基或三氟甲基取代或未取代;
1-甲基吡唑-4-基,其可以在3-位和/或5-位上被甲基、氯、二氟甲基或三氟甲基取代或未取代;或
噁唑-5-基,其可以在2-位和/或4-位上被甲基或氯取代或未取代。
4.上述权利要求之一的杀真菌混合物,其包含其中R2是可以被1、2或3个权利要求1中所述的取代基取代或未取代的苯基的式Ⅰ化合物。
5.权利要求4的杀真菌混合物,其中R2是在2-位上具有下列取代基之一的苯基:
C3-C6-烷基、C5-C6-环烯基、C5-C6-环烷氧基、环烯基氧基,其中这些基团可以被1、2或3个C1-C4-烷基取代,
苯基,其可以被1至5个卤原子和/或1至3个相互独立地选自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,
或其中R2是2,3-二氢化茚基或氧杂2,3-二氢化茚基,其可以被1、2或3个C1-C4-烷基取代。
7.权利要求1至5之任一项的杀真菌混合物,其包含式Ⅰb化合物作为酰胺化合物,其中R4 是卤素和R11 是被卤素取代的苯基。
9.根据上述权利要求之任一项的杀真菌混合物,该混合物被调整成两部分,其中一部分包含在固体或液体载体中的酰胺化合物Ⅰ,而另一部分则包含在固体或液体载体中的一种或多种式Ⅱa至Ⅱc化合物。
10.一种防治有害真菌的方法,该方法包含用权利要求1至9之任一项中的杀真菌混合物处理有害真菌、它们的聚集地、或欲免受它们侵染的材料、植物、种子、土壤、表面或空间,其中活性成分酰胺化合物Ⅰ和一种或多种式Ⅱa至Ⅱc化合物同时,即一起或分别,或先后施用。
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CN103518743A (zh) * | 2013-10-12 | 2014-01-22 | 京博农化科技股份有限公司 | 一种含有啶酰菌胺与烯酰吗啉的杀菌组合物 |
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PE20070409A1 (es) * | 2005-06-29 | 2007-05-07 | Basf Ag | Mezclas fungicidas con base en bifenilamidas de acido pirazolcarboxilico disustituidas en 2,4 |
WO2007003540A1 (de) * | 2005-06-30 | 2007-01-11 | Basf Aktiengesellschaft | Fungizide mischungen auf der basis von 2,5-disubstituierten pyrazolcarbonsäurebiphenylamiden |
US20090042725A1 (en) * | 2005-07-01 | 2009-02-12 | Basf Aktiengesellschaft | Fungicidal Mixtures Based on 3,5-Disubstituted N-Biphenyl-Pyrazolcarboxamides |
JP2009500311A (ja) * | 2005-07-01 | 2009-01-08 | ビーエーエスエフ ソシエタス・ヨーロピア | 3,5−二置換n−ビフェニルピラゾールカルボキサミドをベースとした殺菌剤混合物 |
JP2009500375A (ja) * | 2005-07-06 | 2009-01-08 | ビーエーエスエフ ソシエタス・ヨーロピア | 1−メチルピラゾール−4−イルカルボキシアニリド類から製造される殺菌剤混合物 |
BRPI0613007A2 (pt) * | 2005-07-14 | 2016-11-29 | Basf Ag | misturas fungicidas para combater fungos nocivos fitopatogênicos, agente, processo para combater fungos nocivos fitopatogênicos, semente, e, uso dos compostos |
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