CN1257502A - 杀真菌剂三氟甲基烷氨基三唑并嘧啶 - Google Patents
杀真菌剂三氟甲基烷氨基三唑并嘧啶 Download PDFInfo
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Abstract
一种新颖的通式Ⅰ表示的化合物,式中,R1、R2、Hal和L1~L5的含义如说明书所述,该化合物显现出具有选择性的杀真菌活性。该新颖化合物可与载体及辅料配制成杀真菌组合物。
Description
发明背景
本发明涉及三唑并嘧啶化合物,其制备过程,包含这些化合物的组合物,将这些化合物用于带有真菌的地方杀灭真菌的方法及其作为杀真菌剂的用途。
EP-A-0 071 792要求保护的是以下通式表示的化合物,其中,R1表示可被卤原子或烷氧基取代的烷基、卤原子、烷氧基、氰基、环烷基、芳基、芳氧基、芳硫基、芳烷基、芳硫基、芳烷基、芳烷氧基或芳基烷硫基;(R1)n表示苯、1,2-二氢化茚或与苯环稠合的1,2,3,4-四氢化萘环,以及可被烷基、烷氧基、卤原子或氰基取代的上述基团中的芳香族基团;n表示1或2;R2和R3表示氢原子、烷基或芳基;A表示氮原子或CR4;R4与R2相同,还可表示卤原子、氰基或烷氧羰基,或与R3一起组成包含2个双键的烯烃链。据报道,这些化合物对各种植物病原真菌具有很强的杀灭作用,特别是藻形菌纲的真菌。但是,这些化合物只对一种卵菌纲真菌,即葡萄霜霉菌(Plasmopara viticola)显现出明显的杀灭活性。
发明概述
上述新颖的化合物在各种农田中都显现出极好的选择杀真菌活性。
本发明的目的之一是提供新颖的有选择性的杀真菌化合物。
本发明的另一目的是提供用有效量的上述新颖化合物防治所述植物中的有害真菌的方法。
本发明还有一个目的是提供以上述新颖化合物为活性组分的具有选择性的杀真菌组合物。
本发明的上述及其他目的和特征将在以下具体描述和所附的权利要求中更显而易见。
最佳实施状态的具体说明
一般,除有另外说明,这里所用的卤原子表示溴原子、碘原子、氯原子和氟原子,特别是溴原子、氯原子或氟原子。
卤原子中较好的是氟原子、氯原子、溴原子或碘原子,最好是氯原子。
可被取代部分可以不被取代或带有一个至最大限度的多个取代基。其中,典型的是有0~3个取代基。
一般,除有另外说明,这里所用的烷基、链烯基、炔基、链二烯基是指直链或支链基团。通常,这些基团最多包含10个碳原子,最好为6个碳原子。烷基一般具有1~6个碳原子,更好是具有1~3个碳原子,较好的烷基为乙基,最好的是甲基。链烯基一般具有2~6个碳原子,较好的链烯基是烯丙基,最好的是2-甲基烯丙基。
本发明特别涉及通式I表示的化合物,其中,R1和/或R2的任何烷基部分可以是直链也可以是支链,可最多包含10个碳原子,较好是9个碳原子,更好是6个碳原子。取代基R1和/或R2的链烯基或炔基部分最多可包含10个碳原子,较好是9个碳原子,更好是6个碳原子,其中,每个可被取代的基团都独立地被一个或更多的卤原子或硝基,氰基,环烷基、最好是C3-6环烷基,环链烯基、最好是C3-6环链烯基,卤代烷基、最好是C1-6卤代烷基,卤代环烷基、最好是C3-6卤代环烷基,烷氧基、最好是C1~6烷氧基,卤代烷氧基、最好是C1-6卤代烷氧基,三烷基甲硅烷基、最好是三C1-4烷基甲硅烷基,苯基,卤代或二卤代苯基或吡啶基。任何烷基、链烯基或炔基都可以是直链或支链结构。较好的卤原子包括氟原子、氯原子或溴原子。
本发明特别涉及通式I表示的化合物,式中R1表示氢原子、C1-10烷基或苯基,最好是氢原子或甲基。
本发明中包括通式I表示的化合物的(R)和(S)异构体及内旋异构体(atropisomers),其中具有手性中心或者取代基L1或L1和L2与L5或L5和L4不同,还包括其外消旋物、其盐、其N氧化物和酸加成物。
通式I表示的化合物的(S)异构体具有最令人关注的活性,其中的手性中心在-CH(CF3)R1基团处。
本发明的另一较好实施状态是通式I表示的R2为氢原子或C1-10烷基或C3-10链烯基的化合物。理想的情况是,这些通式I表示的化合物中至少R1和R2之一为氢原子。
通式I表示的化合物为油状物、胶状物,或主要为结晶固状物。它们通过自身良好的杀真菌特性,特别是利用它们显著的内吸性和真菌毒性能够防治稻类病害和白粉病菌。例如,它们可被用于农业或其他相关领域来防治植物病原真菌,如马铃暑早疫病、灰霉病、甜菜褐斑病、稻黑霉病、紫苜蓿白绢病、白粉病、小麦黄斑病、小麦颖枯病、雪腐病、褐腐病、菊花腐病、豌豆黑斑病、稻瘟病、丝核菌病、苹果黑星病、葡萄白粉病和菌核病,而对防治葡萄白粉病、稻瘟病、和丝核菌病特别有效。本发明的通式I表示的化合物在广泛的浓度范围内具备很高的杀真菌活性,它们可以毫无困难地用于农业。
而且,与常规杀真菌剂相比,本发明的化合物对真菌显现出明显的残效活性,特别是对葡萄上的粉状霉菌。
利用通式I表示的化合物能够很好地防治植物病原真菌,该化合物中,至少L1和L5之一为氢原子,和/或R1为氢原子或甲基。
利用以下通式I表示的化合物能够更好地防治植物病原真菌:
5-氯-6-(2-氯-6-氟苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-7-(2,2,2-三氟乙氨基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-(2,2,2-三氟-乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-甲基苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N-(2,2,2-三氟乙基)-N-烯丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-烯丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-烯丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-烯丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-[N-(2,2,2-三氟乙基)-N-烯丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-甲基苯基)-7-[N-(2,2,2-三氟乙基)-N-烯丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-乙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-乙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N-(2,2,2-三氟乙基)-N-乙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-乙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-[N-(2,2,2-三氟乙基)-N-乙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-甲基苯基)-7-[N-(2,2,2-三氟乙基)-N-乙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(2-甲基丙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(2-甲基丙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(2-甲基丙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(2-甲基丙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-甲基苯基)-7-[N-(2,2,2-三氟乙基)-N-(2-甲基丙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-甲氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-甲氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N-(2,2,2-三氟乙基)-N-甲氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-甲基苯基)-7-[N-(2,2,2-三氟乙基)-N-甲氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-异丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-异丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N-(2,2,2-三氟乙基)-N-异丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-异丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(1-苯基乙基)氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[N,N-二-(2,2,2-三氟乙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-甲基苯基)-7-[N,N-二-(2,2,2-三氟乙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-[N,N-二-(2,2,2-三氟乙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[N,N-二-(2,2,2-三氟乙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N,N-二-(2,2,2-三氟乙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N,N-二-(2,2,2-三氟乙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(1,2-二甲基丙基)氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(三甲基甲硅烷基)氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-溴-5-氯苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(4-氯苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(4-溴苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(4-甲氧苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(4-硝基苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-(1-苯基-2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[2-(1,1,1-三氟)丁氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-(1-苯基-2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[2-(1,1,1-三氟)丁氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-(1-苯基-2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-(1-苯基-2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[2-(1,1,1-三氟)丁氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[2-(1,1,1-三氟)丁氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-[2-(1,1,1-三氟)丁氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-(1-苯基-2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4-二氟苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[2-(1,1,1-三氟)-3-甲基丁氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟-4-甲氧基苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶。
通式II中的L1~L5和Hal的含义如以下任一权利要求所述。通式III中的R1和R2如前所述,M表示氢原子或游离或配位金属原子,该金属原子最好选自Li、Na、K、Zn和Cu。
在溶剂中或无溶剂情况下,使所得的5,7-二羟基-6-苯基三唑并嘧啶再与卤化剂反应,最好是与溴化剂或氯化剂反应,如三溴氧磷或三氯氧磷。上述反应可在0℃~150℃的温度范围内进行,最好的反应温度是80℃~125℃。
通式II的5,7-二卤代-6-苯基三唑并嘧啶和通式III的胺或酰胺在溶剂存在下易于反应。适用的溶剂包括醚类,如二噁烷和乙醚,最好是四氢呋喃,而卤代烃类,如二氯甲烷,芳烃类,如甲苯。上述反应较好是在0℃~70℃的温度范围内进行,最好的反应温度范围是10℃~35℃。上述反应也最好在碱存在的情况下进行。适用的碱包括叔胺类,如三乙胺,无机碱类,如碳酸钾或碳酸钠。也可将过量的通式III的化合物作为碱使用。
使7-氨基-5-卤代-6-苯基三唑并嘧啶和三氟链烷酸或其反应衍生物,特别是三氟乙酸酐反应也可制得本发明的化合物,在碱存在下,三氟链烷酸会转变为三氟链烷酰胺。
M为氢原子的通式III表示的胺在文献中有所记载,还可从市场上买到,或者按照已知方法制备。一般,M为金属原子的通式III表示的酰胺可通过相应的胺(M=氢原子)和烷基锂化合物的反应而制得,也可在该反应之后再进行金属转移反应。
由于通式I表示的化合物所具备的极好活性,所以,可被用于因受植物病原真菌侵害的所有庄稼,如谷类、solanaceous稻、蔬菜、豆类、苹果、葡萄(葡萄)等。
人们发现通式I表示的化合物具备杀真菌活性。因此,本发明进一步提供了包含活性组分和一种或多种载体的杀真菌组合物,所述活性组分至少为上述通式I化合物中的一种。还提供了使上述通式I表示的化合物与上述载体相结合形成组合物的方法。这种组合物中可以包含一种本发明的活性组分,也可包含数种活性组分的混合物。可以想象,不同的异构体或异构体的混合物具备不同水平的活性或活性谱,因此,组合物可包含不同的异构体和异构体的混合物。
本发明的组合物最好包含0.5~95%(w/w)的活性组分。
本发明组合物中的载体只要与其配制在一起后有利于施用到受防治的场所(例如,植物、种子、土壤或施用于长有植物的水中),或者有利于储存、运输或处理即可。这种载体可以是固状的也可是液状的,还包括正常状态下为气体但已被压缩为液状的载体。
通过己建立的生产流程,上述组合物可制成浓缩乳剂、溶液剂、水包油乳剂、可湿性粉剂、可溶性粉剂、浓缩悬浮剂、粉剂、颗粒剂、水分散性颗粒剂、微囊剂、凝胶剂、片剂和其他制剂形式。这些生产过程包括充分混合和/或研磨活性组分和填充剂、溶剂、固状载体、表面活性化合物(表面活性剂)等其他组分,及可任意加入的固状和/或液状助剂和/或佐剂。使用该组合物,可根据所希望的目的和客观环境选择适合于这些组合物的喷雾、雾化、分散或倾注等方式。
所用溶剂可以是芳烃,如Solvesso_220;取代的萘类;苯二甲酸酯类,如苯二甲酸二丁酯或苯二甲酸二辛酯;脂族烃,如环己烷或石蜡;醇类和二元醇类及它们的醚和酯,如乙醇、乙二醇一甲醚和二甲醚;酮类,如环己酮;强极性溶剂,如N-甲基-2-吡咯烷酮或γ-丁内酯;高级烷基吡咯烷酮,如正辛基吡咯烷酮或环己基吡咯烷酮;环氧化植物油脂,如甲基化椰子或豆油酯和水。不同液体的混合物一般都适用。
可用于粉剂、可湿性粉剂、水分散性颗粒剂或颗粒剂的固状载体可以是矿物填料,如方解石、滑石粉、高岭土、蒙脱石或硅镁土。用于颗粒剂的载体可以是多孔性材料,如浮石、高岭土、海泡石、皂土,无吸附作用的载体可用方解石或砂子。另外,还可使用大量预先制成颗粒状的无机或有机材料,如白云石或碾碎的植物残渣。
通常以浓缩形式配制或运输农药组合物,随后由用户在使用前稀释。小剂量载体(表面活性剂)的存在方便了稀释过程。因此,本发明组合物中的至少一种载体以表面活性剂为宜。例如,组合物中可包含2种或更多的载体,而其中至少一种为表面活性剂。
根据欲配制的通式I表示的化合物的性质,表面活性剂可以是具有良好分散性、乳化性和润湿性的非离子型、阴离子型、阳离子型或两性离子型物质。上述表面活性剂也可以是各表面活性剂的均匀混合物。
本发明的组合物可配制成可湿性粉剂、水分散性颗粒剂、粉尘剂、颗粒剂、片剂、溶液剂、可乳化的浓缩物、乳剂、浓缩悬浮剂和气雾剂。可湿性粉剂中通常包含5~90%w/w的活性组分,一般除了固态惰性载体之外,还包含3~10%w/w的分散剂和湿润剂。根据需要还可包含0~10%w/w稳定剂和/或其他添加剂,如渗透剂或粘着剂。粉剂通常制成粉末浓缩物形式,其组分与上述可湿性粉剂相似,但不含分散剂,在田间使用时用另外的固态载体稀释就可获得一般含有0.5~10%w/w活性组分的组合物。水分散性颗粒剂和颗粒剂的大小通常为0.15mm~2.0mm,可通过各种技术制得。一般来说,这些类型的颗粒剂中含有0.5~90%w/w活性组分和0~20%w/w添加剂,如稳定剂、表面活性剂、缓释调节剂和粘合剂。所谓的“干燥流体”中包含活性组分浓度相对较高的大小相对较小的颗粒。可乳化的浓缩物中除了溶剂或溶剂混合物之外,通常还包含1~80%w/v活性组分、2~20%w/v乳化剂和0~20%w/v其他添加剂,如稳定剂、渗透剂和缓蚀剂。悬浮浓缩剂一般经过研磨后可获得稳定的、不沉降的、可流动的产物,一般含有5~75%w/v活性组分、0.5~15%w/v分散剂、0.1~10%w/v的保护胶体和触变剂等悬浮剂、0~10%w/v的消泡剂、缓蚀剂、稳定剂、渗透剂、粘着剂等其他添加剂及水或不会溶解活性组分的有机溶液。制剂中可溶解某些有机固状物或无机盐以利于沉降和结晶,或作为防冻剂使用。
按本发明配制的产物用水稀释能获得水性分散体组合物和乳剂组合物,这也在本发明的范围内。
最令人感兴趣的是延长本发明化合物的防护活性的持续时间所用的载体,它能够使农药化合物缓慢地释放到需保护植物的环境中。
在喷雾时加入佐剂可提高活性组分的生物活性。这里所指是能够提高活性组分的生物活性,但其本身并无明显生物活性的的佐剂。该佐剂可作为共配剂或载体包含在配方中,也可与含有活性组分的制剂一起加入到喷雾容器中。
作为一种商品,组合物一般以浓缩形式出售,用户一般使用经过稀释的组合物。组合物可稀释成含有0.001%活性组分的农药,其使用剂量一般在0.01~10kga.i./ha(有效成份/公顷)的范围内。
本发明的配方实例如下:
浓缩乳剂(EC)
活性组分 实施例8的化合物 30%(w/v)
乳化剂 Atlox_4856B/Atlox_4858B1)(含有磺化烷基芳 5%(w/v)
基钙、脂肪醇的乙氧基化物和轻质芳香族化合
物的混合物/含有磺化烷基芳基钙、脂肪醇的
乙氧基化物和轻质芳香族化合物的混合物)
溶剂 Shellsol_A2)(C9~C10芳香族烃类的混合物) 加至1000ml
浓缩悬浮剂(SC)
活性组分 实施例8的化合物 50%(w/v)
分散剂 Soprophor_FL3)(聚氧乙烯,聚芳基苯基醚,磷 3%(w/v)
酸胺盐)
消泡剂 Rhodorsil_4223)(聚二甲基硅氧烷的非离子型 0.2%(w/v)
水性乳剂)
结构助剂 Kelzan_S4)(黄原胶) 0.2%(w/v)
防冻剂 丙二醇 5%(w/v)生物杀伤剂Proxel_5)(含20%1,2-苯并异噻唑啉-3-酮的二 0.1%(w/v)
丙二醇水溶液)
水 加至1000ml
可湿性粉剂(WP)
活性组分 实施例8的化合物 60%(w/w)
湿润剂 Atlox_49951)(聚氧乙烯烷基醚) 2%(w/w)
分散剂 Witcosperse_D-606)(萘磺酸和烷基芳基聚氧乙 3%(w/w)
酸酯缩合物钠盐的混合物)
载体/填料 高岭土 35%(w/w)
水分散性颗粒剂(WG)
活性组分 实施例8的化合物 50%(w/w)
分散剂/粘合剂 Witcosperse_D-4506)(萘磺酸和烷基磺酸 8%(w/w)
酯缩合物钠盐的混合物)
湿润剂 Morwet_EFW6)(甲醛的缩合物) 2%(w/w)
消泡剂 Rhodorsil_EP 67036)(包胶的硅酮) 1%(w/w)
崩解剂 Agrimer_ATF7)(N-乙烯基-2-吡咯烷酮的 2%(w/w)
交联均聚物)
载体/填料 高岭土 35%(w/w)
1)ICI Surfactants公司的产品
2)Deutsche Shell AG公司的产品
3)罗纳-普朗克公司的产品
4)Kelco公司的产品
5)Zeneca公司的产品
6)Witco公司的产品
7)International Speciality Products公司的产品
本发明的组合物中还可包含其他具有生物活性的化合物,例如,具有相似或补充杀虫活性的化合物或具有植物生长调节、杀真菌和杀虫活性的化合物。这些农药的混合物所具备的活性谱比单独的通式I表示的化合物更广。而且,其他农药在杀虫活性上与通式I表示的化合物有增效作用。
其他杀真菌化合物也能够防治如白粉病、锈病、白星病、根腐病和叶枯病等引起的谷类(如小麦)虫害;种子和土壤病害;葡萄霜霉病和葡萄白粉病;茄科作物的早疫和晚疫病;苹果树上的白粉病和疮痂病等。这些农药的混合物所具备的活性谱比单独的通式I表示的化合物更广。而且,其他农药在杀虫活性上与通式I表示的化合物有协同作用。
其他杀真菌化合物的例子包括敌菌灵、azoxystrobin、苯霜灵、苯菌灵、乐杀螨、双苯三唑并醇、灭瘟素、波尔多液、戊唑醇、乙嘧酚磺酸酯、敌菌丹、克菌丹、多菌灵、萎锈灵、百菌清、乙菌利、王铜和硫酸铜等含铜化合物、放线菌酮、霜脲氰、酯菌胺、环唑醇、cyprodinil、苯氟磺胺、二氯萘醌、氯硝胺、苄氯三唑并醇、哒菌清、乙霉威、噁醚唑、diflumetorim、二甲嘧酚、烯酰吗啉、烯唑醇、二硝巴豆酸酯、灭菌磷、二噻农、十二环吗啉、多果定、克瘟散、epoxiconazole、乙环唑、乙嘧酚、土菌灵、famoxadone、咪菌腈、氯苯嘧啶醇、fenbuconazole、甲呋酰苯胺、fenhexamid、拌种咯、苯锈啶、丁苯吗啉、毒菌锡、三苯基醋酸锡、三苯基氢氧化锡、嘧菌腙、氟啶胺、fludioxonil、flumetover、fluquinconazole、氟硅唑、磺菌胺、氟酰胺、粉唑醇、灭菌丹、乙磷铝、麦穗宁、呋霜灵、furametpyr、谷种定、己唑醇、抑霉唑、双胍辛醋酸盐、ipconazole、异菌脲、iprovalicarb、稻瘟灵、春雷霉素、异稻瘟净、kresoxim-methyl、代森锰锌、代森锰、嘧菌胺、灭锈胺、甲霜灵、metconazole、呋菌胺、腈菌唑、neoasozin、N,N-二甲基二硫代氨基甲酸镍、间硝酞异丙酯、氟苯嘧啶醇、甲呋酰胺、有机汞化合物、噁霜灵、氧化萎锈灵、戊菌唑、戊菌隆、叶枯净、多氧霉素D、代森联、烯丙异噻唑、咪鲜安、procymidione、丙酰胺、丙环唑、丙森锌、吡嘧磷、啶斑肟、pyrimethanil、氯吡呋醚、灭螨猛、quinoxyfen、五氯硝基苯、spiroxamine、SSF-126、SSF-129、链霉素、硫黄、戊唑醇、叶枯酞、四氯硝基苯、氟醚唑、噻菌灵、thifluzamide、甲基硫菌灵、福美双、甲基立枯磷、甲苯氟磺胺、三唑并酮、三唑并醇、trizbutil、唑菌嗪、十三吗啉、氟菌唑、嗪氨灵、triticonazole、稻纹散、乙烯菌核剂、XRD-563、zarilamid、代森锌、福美锌。
另外,本发明的复合配方中可包含至少一种通式I表示的化合物和任何一种以下列出的生物防治制剂,如病毒、细菌、线虫、真菌和其他适用于防治昆虫、杂草或植物病害或诱导植物中宿主抗性的微生物。这些生物防治剂具体包括苏云金芽胞杆菌、轮枝孢菌、苜蓿夜蛾NPV、巴西安白僵菌、Ampelomyces quisqualis、枯草芽胞杆菌、绿叶假单胞菌(Pseudomonas chlororaphis)、荧光假单胞菌、灰绿链霉菌(Streptomyces griseoviridis)和Trichoderma harzianum。
此外,本发明的复合配方中可包含至少一种通式I表示的化合物和能够诱导植物体内的后天抗性的化学剂,如烟酸或其衍生物或BION。
通式I表示的化合物可与土壤、泥煤或其他根部介质混合来防治生长于植物种子、土壤或叶面的菌类病害。
本发明还提供了上述通式I表示的化合物或上述组合物作为杀真菌剂的用途,以及在需防治真菌的场所使用上述化合物或组合物的方法,这些场所包括主动或被动地受到真菌侵害的植物,和这些植物的种子及生长有或就要生长这些植物的介质。
本发明可广泛用于保护作物和观赏植物抵御真菌的侵害。可受到保护的典型的作物包括葡萄、小麦和大麦等谷类作物、稻子、甜菜、冠果树(top fruit)、花生、马铃薯、蔬菜和西红柿。防治持续时间一般根据所选择的各种化合物而定,也受到气候等外因的影响,这种影响可通过使用适当的组合物而减轻。
以下的实施例进一步对本发明进行了阐述。但是,本发明并不仅限于以下给出的实施例。
实施例1
5-氯-6-(2-氯-6-氟苯基)-7-N-(2,2,2-三氟乙氨基)-1,2,4-三唑并[1,5α]嘧啶
在搅拌状态下,将2,2,2-三氟乙胺(4.2mmol)和二氯甲烷(10ml)的混合物加入5,7-二氯-6-(2-氯-6-氟苯基)-1,2,4-三唑并[1,5α]嘧啶(1.4mmol)和二氯甲烷(30ml)的混合物中。在室温下搅拌上述反应混合物16小时后,分别用1N盐酸和水洗涤上述混合物2次和1次。然后,分离出有机层,用无水硫酸钠干燥,减压蒸出溶剂。用叔丁基甲基醚(50ml)处理反应所得的淡褐色油状物后获得熔点为194~197℃的米色结晶。
实施例2~69
以下所示例子(表1,结构和熔点)合成与实施例1相似。
实施例 | R1 | R2 | L1 | L2 | L3 | L4 | L5 | 熔点(℃) |
2 | H | H | Cl | H | H | H | H | 165 |
3 | H | H | F | H | F | H | F | 195 |
4 | H | H | F | H | H | H | H | 180 |
5 | H | H | F | H | H | H | F | 137 |
6 | CH3 | H | Cl | H | H | H | F | 165-176 |
7 | CH3 | H | F | H | H | H | F | 166-167 |
8 | CH3 | H | F | H | F | H | F | 184-185 |
9 | CH3 | H | CH3 | H | H | H | H | 149-151 |
10 | CH3 | H | F | H | H | H | H | 128-130 |
11 | CH3 | H | Cl | H | H | H | H | 129-130 |
12 | H | 烯丙基 | F | H | F | H | F | 104-105 |
13 | H | 烯丙基 | Cl | H | H | H | F | 145-146 |
14 | H | 烯丙基 | F | H | H | H | H | 128 |
15 | H | 烯丙基 | F | H | H | H | F | 109-111 |
16 | H | 烯丙基 | Cl | H | H | H | H | 129-130 |
17 | H | 烯丙基 | CH3 | H | H | H | H | 123-130 |
18 | H | 乙基 | F | H | H | H | H | 136-139 |
19 | H | 乙基 | F | H | H | H | F | 164-166 |
20 | H | 乙基 | F | H | F | H | F | 133-134 |
21 | H | 乙基 | Cl | H | H | H | F | 199-202 |
22 | H | 乙基 | Cl | H | H | H | H | 150-158 |
23 | H | 乙基 | CH3 | H | H | H | H | 174-178 |
24 | H | 2-甲基丙基 | Cl | H | H | H | F | 175 |
25 | H | 2-甲基丙基 | F | H | H | H | F | 154-155 |
26 | H | 2-甲基丙基 | F | H | H | H | H | 144 |
27 | H | 2-甲基丙基 | F | H | F | H | F | 133-134 |
28 | H | 2-甲基丙基 | CH3 | H | H | H | H | 154-155 |
29 | H | 甲基 | F | H | H | H | H | 142-143 |
30 | H | 甲基 | F | H | H | H | F | 175-177 |
31 | H | 甲基 | F | H | F | H | F | 163 |
32 | H | 甲基 | F | H | H | H | Cl | 178-180 |
33 | H | 甲基 | CH3 | H | H | H | H | 147-149 |
34 | H | 异丙基 | F | H | H | H | F | 147-150 |
35 | H | 异丙基 | F | H | H | H | Cl | 178-183 |
36 | H | 异丙基 | F | H | F | H | F | 154-158 |
37 | H | 异丙基 | F | H | H | H | H | 167-170 |
38 | H | 1-苯基乙基 | F | H | H | H | H | 油状物 |
39 | H | 2,2,2-三氟乙基 | Cl | H | H | H | H | 212-213 |
40 | H | 2,2,2-三氟乙基 | CH3 | H | H | H | H | 223-226 |
41 | H | 2,2,2-三氟乙基 | F | H | H | H | H | 185-186 |
42 | H | 2,2,2-三氟乙基 | F | H | H | H | Cl | 234-237 |
43 | H | 2,2,2-三氟乙基 | F | H | H | H | F | 208-210 |
44 | H | 2,2,2-三氟乙基 | F | H | F | H | F | 177-179 |
45 | H | l,2-二甲基丙基 | F | H | H | H | F | 154-158 |
46 | H | 三甲基甲硅烷基甲基 | F | H | F | H | F | 85 |
47 | CH3 | 甲基 | Br | H | H | Cl | H | 160-169 |
48 | H | H | H | H | Cl | H | H | 170 |
49 | H | H | H | H | Br | H | H | 176-177 |
50 | H | H | H | H | OCH3 | H | H | 183-185 |
51 | H | H | H | H | NO2 | H | H | 237 |
52 | C6H5 | H | F | H | H | H | H | 114 |
53 | C2H5 | H | F | H | H | H | Cl | 162 |
54 | C6H5 | H | F | H | H | H | Cl | 108 |
55 | C2H5 | H | F | H | H | H | H | 133 |
56 | C6H5 | H | F | H | H | H | F | 148 |
57 | C6H5 | H | F | H | F | H | F | 86 |
58 | C2H5 | H | F | H | F | H | F | 177 |
59 | C2H5 | H | F | H | F | H | F | 17l |
60 | C2H5 | H | Cl | H | H | H | H | 油状物 |
61 | C6H5 | H | Cl | H | H | H | H | 油状物 |
62 | H | H | F | H | F | H | H | 181 |
63 | i-C3H7 | H | F | H | F | H | F | 104 |
64 | H | H | F | H | OCH3 | H | F | 油状物 |
65 | H | H | F | H | H | H | Br | 187 |
66 | CH3 | H | F | H | H | H | Br | 184-185 |
67 | H | H | F | F | H | H | F | 183 |
68 | CH3 | H | F | F | H | H | F | 149 |
69 | H | H | F | F | F | F | F | 油状物 |
生物鉴定
A.利用分次稀释试验确定试验化合物对各种植物病原真菌的最小抑制浓度
MIC(最小抑制浓度)值是指生长介质中决定菌丝体生长的总抑制性能的活性组分最低浓度,该值可用24或48孔微量板的分次稀释试验测定。在对营养溶液中的试验化合物稀释并将其注入孔中时所用的是TECANRSP 500Robotic分样器。所用试验化合物的浓度分别为0.05、0.10、0.20、0.39、0.78、1.56、3.13、6.25、12.50、25.00、50.00和100.00mg/ml。将V8蔬菜汁(333ml)和碳酸钙(4.95g)混合,然后离心,用水(800ml)稀释上清液(200ml),并在121℃高压加热30分钟就可制得试验所需的营养溶液。
将各菌种(索兰尼式链格孢,ALTESO;灰葡萄孢,BOTRCI;leptosphaerianodorum,LEPTNO;致病疫霉,PHYTIN;Magnaporthe griseaf.sp.oryzae,PYRIOR;圆核腔菌,PYRNTE;立枯丝核菌,RHIZSO)加入到各孔中形成孢子悬浮液(50ml;5×105/ml)或在真菌琼脂培养基中形成琼脂切片(6mm)。
在适当的温度(18℃~25℃)下培养6~12天后,通过对板的外观检查可确定MIC值(表2,n.t.表示未测得)。
表2
实施例 | ALTESO | BOTRCI | LEPTNO | PHYTIN | PYRIOR | PYRNTE | RHISZO |
1 | 3.13 | 1.56 | 6.25 | 12.5 | 0.78 | 6.25 | 6.25 |
2 | 12.5 | 6.25 | 50 | 12.5 | 0.78 | 12.5 | 25 |
3 | 1.56 | 1.56 | 6.25 | 25 | 0.2 | 6.25 | 6.25 |
6 | 3.13 | 12.5 | 25 | >100 | 3.13 | 25 | 6.25 |
7 | 1.56 | 25 | 50 | >100 | 0.78 | 12.5 | 6.25 |
8 | 0.78 | 3.13 | 3.13 | >100 | 0.78 | 6.25 | 3.13 |
9 | 25 | 25 | 12.5 | >100 | 3.13 | >100 | 12.5 |
10 | 6.25 | >100 | 50 | 25 | 1.56 | >100 | 12.5 |
11 | 3.13 | 6.25 | 25 | 100 | 0.39 | 6.25 | 6.25 |
12 | 0.39 | 0.78 | 3.13 | >100 | 0.04 | 3.13 | 0.78 |
13 | 3.13 | 3.13 | >100 | >100 | 0.1 | >100 | 1.56 |
15 | 1.56 | 1.56 | 6.25 | >100 | 0.04 | 6.25 | 1.56 |
16 | 1.56 | 6.25 | 12.5 | >100 | 0.39 | 50 | 50 |
19 | 0.78 | 1.56 | >100 | >100 | 0.04 | >100 | 0.78 |
20 | 0.78 | 0.78 | 3.13 | >100 | 0.04 | 1.56 | 0.78 |
27 | 0.2 | 0.2 | 0.39 | >100 | 0.04 | >100 | 3.13 |
30 | 3.13 | 12.5 | >100 | >100 | 0.78 | 25 | >100 |
31 | 0.78 | 3.13 | 50 | >100 | 0.1 | 12.5 | 1.56 |
46 | 0.78 | 6.25 | >100 | 25 | 1.56 | 25 | >100 |
47 | 12.5 | 12.5 | 25 | >100 | 1.56 | >100 | 50 |
49 | 12.5 | 25 | 50 | 100 | 0.78 | 25 | 50 |
53 | 6.25 | 12.5 | >100 | >100 | 1.56 | >100 | >100 |
55 | 3.13 | 12.5 | 50 | >100 | 1.56 | >100 | >100 |
56 | 3.13 | 12.5 | >100 | >100 | 1.56 | 3.13 | >100 |
57 | 50 | >100 | >100 | >100 | 0.78 | 100 | >100 |
59 | 6.25 | 12.5 | 25 | >100 | 0.39 | >100 | 6.25 |
60 | 3.13 | 25 | 25 | 25 | 1.56 | 25 | 25 |
61 | 0.39 | 1.56 | 1.56 | 100 | 0.04 | 6.25 | 12.5 |
标准品 | 12.5 | 12.5 | 100 | >100 | 50 | 50 | 100 |
*标准品为5-氯-6-(2-氯苯基)-7-N-乙氨基-1,2,4-三唑并[1,5α]嘧啶;该化合物与实施例2的化合物相对应,但其中的7-(2,2,2-三氟乙基)氨基被7-乙氨基取代。
B.确定葡萄叶上的葡萄白粉病的残留防治活性,评估通式I的化合物对葡萄上的葡萄白粉病的防治效果的方法。
试验植物
在温度为18~25℃、相对湿度为50~70%的暖房中培养(Muller-Thurgau)培养物切块。长出6~8片叶子后,将植株修剪成平均每株有3~4片叶子。然后,将这些植物移植到装有植物测杆培养基的容器中。
应用
每次处理3~4株植物。在植物病原真菌侵害的3天前用通式I化合物处理。在喷雾槽中向植株喷洒20ml农药。上述通式I的化合物以0.5%的浓度溶于丙酮中。储液用水稀释至最终浓度。配得的杀真菌剂也在使用前用水稀释。
感染
将来自葡萄白粉病菌培养物的新形成孢子的葡萄叶的孢子撒在试验植物上作人工感染,让这些孢子在叶片上停留1个小时。继续将植物在温度为16~30℃的未额外照明的暖房中放置24小时。
评估
评估在植物受到侵害的21天后进行,通过计算对处理过的4片叶子的每片受侵害面积的平均值评估杀真菌剂效果。用ABBOTT公式即可算出活性%。
%活性=100-(经处理的植物虫害%/未经处理植物的虫害%)×100
评估结果如表3所示。
表3 葡萄上的葡萄白粉病
实施例 比率(ppm有效成份) 效果(%)3 25 10012.5 1006.25 1003.13 912 25 3812.5 196.25 53.13 08 25 10012.5 1006.25 1003.13 97 |
标准品* 25 512.5 116.25 23.13 0 |
*与测定MIC值所用的标准品相同。
C.叶面内吸性
C-1:葡萄品种为Muller-Thurgau
病原体:葡萄白粉病
试验步骤:
1.使葡萄切块生长在直径为8cm的塑料盒中,并放置在暖房中。
2.在空气压为500兆巴的条件下,用带有0.5mm圆形喷嘴的气刷沿横向区域将配得的化合物喷在刚生长完全的叶片上。用一张带有5mm宽细缝的卡纸作为遮掩物使其与叶片的轴线垂直,这样此时的喷洒区域就是较下方的叶片表面。用永久性记号笔在较上方的叶片表面标出区域位置,具有代表性的是距顶点4cm。上述操作完成后,不要移动该植株直至上述区域干燥为止。
3.经处理的植物在干燥后被移入暖房,并在其中放置2天使化合物充分发挥作用。继续向植物根部洒水。
4.施用化合物2天后,在暖房中通过喷洒的方法将白粉病菌孢子接种于葡萄植株。在试验植物上方空气中,用刷子对原培养植物的形成孢子而受到感染的叶片轻轻一掠,使孢子停留在叶片表面上部。评估在接种12~14后进行。
C-2小麦白粉病(WPM)
宿主: 小麦(Triticum aestivum L.)种类为Kanzler
病原体:小麦白粉病菌
试验步骤:
1.将小麦种子(8/罐)培植在直径为8cm的塑料罐中,并放置在暖房中。
2.当新叶完全长成时,将植株修剪成每罐有4片叶子的样子,并用永久性记号笔在其中2片的距叶片顶端5cm的较上方叶片表面做记号,这样就在每罐中分出两个经处理的区域和两个未经处理的区域。
3.在记号的下方叶片表面用移液管滴上5μl配得的化合物。上述操作需覆盖整个叶面宽度。完成上述操作后,不要移动植株直至其干燥为止(1个半小时或更长时间)。
4.经处理的植物在于燥后移入暖房,并在其中放置2天使化合物充分发挥作用。继续向植物根部洒水。
5.施用化合物2天后,在暖房中通过喷洒的方法将白粉病菌孢子接种于植株。在接种7~8天后进行评估。或者,给植株接种小麦叶锈病菌(小麦叶锈病原),并在7~8天后评估。
评估
对经过处理的叶片的3个不同的区域的虫害感染情况评估,测定化合物在这3个区域的不同吸收率。
中间吸收:测定中间区域的病害感染百分比(经处理的较下方叶片表面区域对应于做过记号的较上方叶片表面;区域宽度大约为5mm)。中间区域的病害防治百分比可由下式算出:
%活性=100-(经处理的植物病害%/未经处理植物的病害%)×100
远端吸收和近端吸收:以毫米为单位测出较上方叶片表面未受到病害感染的远端和近端区域。远端是指经处理区域到叶片顶点的方向,近端是指经处理区域到叶片底部的方向。计算未受病害感染的区域相对于经处理区域到叶片顶点或底部的距离的百分数(葡萄,40mm为100%)。即使远端和近端区域内的病害感染不严重,也需注意。
配制和防治:
1.在含5%丙酮和去离子水中的0.05%吐温20的溶剂/表面活性剂系统中配制化合物。在用吐温水稀释化合物前使其溶于丙酮中。用去离子水制备化合物。具有代表性的是在40ppm的条件下测定化合物。
2.包括三种防治方法:
用溶剂/表面活性剂溶液进行畦幅处理的植物和接种(未用溶剂)。
经过接种的未用化合物进行处理的植物(接种防治)。
上述评估结果如表4所示,其中的病害缩写如下:
小麦白粉病WPM
葡萄白粉病GPM
小麦叶锈病WLR
表4 叶面内吸性
实施例 | 病害 | 近端吸收(mm,从处理区域开始的距离) | 远端吸收(mm,从处理区域开始的距离) | 中间活性(%) |
1 | WPMGPMWLR | 365 | 435048 | 100100100 |
2 | GPMWLR | 84 | 3621 | 100100 |
3 | GPMWLR | 74 | 5023 | 100100 |
4 | GPMWLR | 73 | 326 | 100100 |
标准品2 | GPMWLR | 24 | 68 | 100100 |
标准品2为美国专利No.5,593,996揭示的5-氯-7-(4-甲基哌啶-1-基)-6-(2-氯-6-氟苯基-[1,2,4]三唑并[1,5-α]嘧啶。
Claims (10)
2.如权利要求1所述的化合物,其中,至少L1和L5之一表示卤原子。
3.如权利要求1或2所述的化合物,其中,R1表示氢原子或甲基。
4.如权利要求1~3的任一项所述的化合物,其中,R2表示氢原子或C1~10烷基。
5.如权利要求1~4的任一项所述的化合物,其中,至少R1和R2之一表示氢原子。
6.以下通式I表示的化合物:5-氯-6-(2-氯-6-氟苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-7-(2,2,2-三氟乙氨基)-6-(2,4,6-三氟苯基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-(2,2,2-三氟-乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-甲基苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N-(2,2,2-三氟乙基)-N-烯丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-烯丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-烯丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-烯丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-[N-(2,2,2-三氟乙基)-N-烯丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-甲基苯基)-7-[N-(2,2,2-三氟乙基)-N-烯丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-乙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-乙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N-(2,2,2-三氟乙基)-N-乙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-乙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-[N-(2,2,2-三氟乙基)-N-乙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-甲基苯基)-7-[N-(2,2,2-三氟乙基)-N-乙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(2-甲基丙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(2-甲基丙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(2-甲基丙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(2-甲基丙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-甲基苯基)-7-[N-(2,2,2-三氟乙基)-N-(2-甲基丙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-甲氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-甲氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N-(2,2,2-三氟乙基)-N-甲氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-甲基苯基)-7-[N-(2,2,2-三氟乙基)-N-甲氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-异丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-异丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N-(2,2,2-三氟乙基)-N-异丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[N-(2,2,2-三氟乙基)-N-异丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(1-苯基乙基)氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[N,N-二-(2,2,2-三氟乙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-甲基苯基)-7-[N,N-二-(2,2,2-三氟乙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-[N,N-二-(2,2,2-三氟乙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[N,N-二-(2,2,2-三氟乙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N,N-二-(2,2,2-三氟乙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N,N-二-(2,2,2-三氟乙基)-氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(1,2-二甲基丙基)氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[N-(2,2,2-三氟乙基)-N-(三甲基甲硅烷基)氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-溴-5-氯苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(4-氯苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(4-溴苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(4-甲氧基苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(4-硝基苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-(1-苯基-2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-[2-(1,1,1-三氟)丁氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯-6-氟苯基)-7-(1-苯基-2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氟苯基)-7-[2-(1,1,1-三氟)丁氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-(1-苯基-2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-(1-苯基-2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[2-(1,1,1-三氟)丁氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟苯基)-7-[2-(1,1,1-三氟)丁氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-[2-(1,1,1-三氟)丁氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2-氯苯基)-7-(1-苯基-2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4-二氟苯基)-7-(2,2,2-三氟乙氨基)-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,4,6-三氟苯基)-7-[2-(1,1,1-三氟)-3-甲基丁氨基]-[1,2,4]三唑并[1,5-α]嘧啶、5-氯-6-(2,6-二氟-4-甲氧基苯基)-7-[2-(1,1,1-三氟)丙氨基]-[1,2,4]三唑并[1,5-α]嘧啶。
8.一种杀真菌组合物,其中包含载体和作为活性组分的权利要求1~6的任一项所述的通式I表示的化合物中的至少一种。
9.在需进行防治的场所杀灭真菌的方法,其特征在于,在所述场所使用权利要求1~6的任一项所述的通式I表示的化合物或权利要求8所述的组合物。
10.权利要求1~6的任一项所述的通式I表示的化合物或权利要求8所述的组合物作为杀真菌剂使用的用途。
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DE3130633A1 (de) * | 1981-08-01 | 1983-02-17 | Basf Ag, 6700 Ludwigshafen | 7-amino-azolo(1,5-a)pyrimidine und diese enthaltende fungizide |
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CN1313467C (zh) * | 2001-07-18 | 2007-05-02 | 巴斯福股份公司 | 作为杀真菌剂的6-(2,6-二氟苯基)三唑并嘧啶 |
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