CN111741958A - 作为害虫防治剂的稠合双环杂环衍生物 - Google Patents
作为害虫防治剂的稠合双环杂环衍生物 Download PDFInfo
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- CN111741958A CN111741958A CN201980014557.1A CN201980014557A CN111741958A CN 111741958 A CN111741958 A CN 111741958A CN 201980014557 A CN201980014557 A CN 201980014557A CN 111741958 A CN111741958 A CN 111741958A
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Classifications
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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Abstract
本发明涉及新的式(I)的化合物,其中Aa、Ab、Ac、Ad、Q、R1和n如说明书中所定义;涉及其作为杀螨剂和/或杀虫剂用于防治动物害虫的用途;以及涉及用于制备其的方法和中间体。
Description
本发明涉及新的式(I)的稠合双环杂环衍生物;其作为杀螨剂和/或杀虫剂用于防治动物害虫、特别是节肢动物且尤其是昆虫和蛛形纲动物的用途;以及用于制备其的方法和中间体。
具有杀虫特性的稠合杂环衍生物已记载于例如以下文献中:WO 2010/125985、WO2012/074135、WO 2012/086848、WO 2013/018928、WO 2013/191113、WO 2014/142292、WO2014/148451、WO 2015/000715、WO 2016/124563、WO 2016/124557、WO 2016/162318、WO2017/093180、WO 2017/125340、WO 2017/174414、EP-A-3241830、EP17154789.6、WO 2015/121136、WO 2015/002211、WO 2015/071180、WO 2016/020286、WO 2015/059039、WO 2015/190316、WO 2016/091731、WO 2016/107742、WO 2016/162318、PCT/EP2016/075365、WO2017/055185、EP3272756、EP 16189445.6、EP 16200177.0、EP17153317.7、WO 2016/129684、WO 2017/001311、WO 2017/001314、WO 2017/061497、WO 2017/084879、WO 2017/089190、WO2017/133994。
现代作物保护组合物必须满足许多要求,例如与程度、持久性和其作用谱以及可能的用途相关的要求。毒性、有益物种和传粉者的保护、环境特性、施用率、与其他活性成分或制剂助剂的相容性的问题很重要,合成活性成分所涉及的复杂性的问题也很重要,并且还可能出现抗性,仅提及一些参数。仅基于所有这些原因,对新的作物保护组合物的研究不能认为已经完成,并且持续需要与已知化合物相比至少在个别方面具有改进特性的新的化合物。
本发明的一个目的是提供在多方面拓宽农药谱和/或改善其活性的化合物。
现已发现新的稠合双环杂环衍生物,它们比已知化合物具有优点,优点的实例包括更好的生物学特性或环境特性、更广泛的施用方法、更好的杀虫活性或杀螨活性以及与作物植物良好的相容性。稠合双环杂环衍生物可以与其他用于改善功效的试剂结合使用,特别是对抗难以防治的昆虫。
因此,本发明提供新的式(I)的化合物
其中(构型1-1)
Aa为–C(R8)(R9)-,
Ab为–C(R10)(R11)-,
Ac为–C(R12)(R13)-,
Ad为–C(R14)(R15)-,
R1为(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-氰基烷基、(C1-C6)-羟基烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C1-C6)-卤代烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-烯氧基-(C1-C6)-烷基、(C2-C6)-卤代烯氧基-(C1-C6)-烷基、(C2-C6)-卤代烯基、(C2-C6)-氰基烯基、(C2-C6)-炔基、(C2-C6)-炔氧基-(C1-C6)-烷基、(C2-C6)-卤代炔氧基-(C1-C6)-烷基、(C2-C6)-卤代炔基、(C2-C6)-氰基炔基、(C3-C8)-环烷基、(C3-C8)-环烷基-(C3-C8)-环烷基、(C1-C6)-烷基-(C3-C8)-环烷基、卤代-(C3-C8)-环烷基、氨基、(C1-C6)-烷基氨基、二-(C1-C6)-烷基氨基、(C3-C8)-环烷基氨基、(C1-C6)-烷基羰基氨基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-卤代烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷基羰基-(C1-C6)-烷基、(C1-C6)-卤代烷基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基氨基、氨基磺酰基-(C1-C6)-烷基、(C1-C6)-烷基氨基磺酰基-(C1-C6)-烷基、二-(C1-C6)-烷基氨基磺酰基-(C1-C6)-烷基,
R8、R9、R10、R11、R12、R13、R14、R15独立地为氢、氰基、卤素、硝基、乙酰基、羟基、氨基、SCN、三-(C1-C6)-烷基甲硅烷基、(C3-C8)-环烷基、(C3-C8)-环烷基-(C3-C8)-环烷基、(C1-C6)-烷基-(C3-C8)-环烷基、卤代-(C3-C8)-环烷基、氰基-(C3-C8)-环烷基、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-氰基烷基、(C1-C6)-羟基烷基、羟基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-氰基烯基、(C2-C6)-炔基、(C2-C6)-卤代炔基、(C2-C6)-氰基炔基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-氰基烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C6)-烷氧基、(C1-C6)-烷基羟基亚氨基、(C1-C6)-烷氧基亚氨基、(C1-C6)-烷基-(C1-C6)-烷氧基亚氨基、(C1-C6)-卤代烷基-(C1-C6)-烷氧基亚氨基、(C1-C6)-烷硫基、(C1-C6)-卤代烷硫基、(C1-C6)-烷氧基-(C1-C6)-烷硫基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基、(C1-C6)-卤代烷基磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基磺酰基、(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰氧基、(C1-C6)-烷基羰基、(C1-C6)-烷硫基羰基、(C1-C6)-卤代烷基羰基、(C1-C6)-烷基羰基氧基、(C1-C6)-烷氧基羰基、(C1-C6)-卤代烷氧基羰基、氨基羰基、(C1-C6)-烷基氨基羰基、(C1-C6)-烷基氨基硫代羰基、二-(C1-C6)-烷基氨基羰基、二-(C1-C6)-烷基氨基硫代羰基、(C2-C6)-烯基氨基羰基、二-(C2-C6)-烯基氨基羰基、(C3-C8)-环烷基氨基羰基、(C1-C6)-烷基磺酰基氨基、(C1-C6)-烷基氨基、二-(C1-C6)-烷基氨基、氨基磺酰基、(C1-C6)-烷基氨基磺酰基、二-(C1-C6)-烷基氨基磺酰基、(C1-C6)-烷基亚砜亚胺基((C1-C6)-alkylsulfoximino)、氨基硫代羰基、(C1-C6)-烷基氨基硫代羰基、二-(C1-C6)-烷基氨基硫代羰基、(C3-C8)-环烷基氨基、NHCO-(C1-C6)-烷基((C1-C6)-烷基羰基氨基),
在每种情况下为任选地被相同或不同地单取代或多取代的芳基或杂芳基,其中(在杂芳基的情况下)可任选地存在至少一个羰基和/或其中在每种情况下的可能的取代基如下:氰基、羧基、卤素、硝基、乙酰基、羟基、氨基、SCN、三-(C1-C6)烷基甲硅烷基、(C3-C8)环烷基、(C3-C8)环烷基-(C3-C8)环烷基、(C1-C6)烷基-(C3-C8)环烷基、卤代(C3-C8)环烷基、(C1-C6)烷基、(C1-C6)卤代烷基、(C1-C6)氰基烷基、(C1-C6)羟基烷基、羟基羰基-(C1-C6)-烷氧基、(C1-C6)烷氧基羰基-(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷基、(C2-C6)烯基、(C2-C6)卤代烯基、(C2-C6)氰基烯基、(C2-C6)炔基、(C2-C6)卤代炔基、(C2-C6)氰基炔基、(C1-C6)烷氧基、(C1-C6)卤代烷氧基、(C1-C6)氰基烷氧基、(C1-C6)烷氧基羰基-(C1-C6)烷氧基、(C1-C6)烷氧基-(C1-C6)烷氧基、(C1-C6)烷基羟基亚氨基、(C1-C6)烷氧基亚氨基、(C1-C6)烷基-(C1-C6)烷氧基亚氨基、(C1-C6)卤代烷基-(C1-C6)烷氧基亚氨基、(C1-C6)烷硫基、(C1-C6)卤代烷硫基、(C1-C6)烷氧基-(C1-C6)烷硫基、(C1-C6)烷硫基-(C1-C6)烷基、(C1-C6)烷基亚磺酰基、(C1-C6)卤代烷基亚磺酰基、(C1-C6)烷氧基-(C1-C6)烷基亚磺酰基、(C1-C6)烷基亚磺酰基-(C1-C6)烷基、(C1-C6)烷基磺酰基、(C1-C6)卤代烷基磺酰基、(C1-C6)烷氧基-(C1-C6)烷基磺酰基、(C1-C6)烷基磺酰基-(C1-C6)烷基、(C1-C6)烷基磺酰氧基、(C1-C6)烷基羰基、(C1-C6)卤代烷基羰基、(C1-C6)烷基羰基氧基、(C1-C6)烷氧基羰基、(C1-C6)卤代烷氧基羰基、氨基羰基、(C1-C6)烷基氨基羰基、二-(C1-C6)烷基氨基羰基、(C2-C6)烯基氨基羰基、二-(C2-C6)-烯基氨基羰基、(C3-C8)环烷基氨基羰基、(C1-C6)烷基磺酰基氨基、(C1-C6)烷基氨基、二-(C1-C6)烷基氨基、氨基磺酰基、(C1-C6)烷基氨基磺酰基、二-(C1-C6)烷基氨基磺酰基、(C1-C6)烷基亚砜亚胺基、氨基硫代羰基、(C1-C6)烷基氨基硫代羰基、二-(C1-C6)烷基氨基硫代羰基、(C3-C8)环烷基氨基、(C1-C6)烷基羰基氨基,
Q为部分饱和的或饱和的杂环的或杂芳族的8、9、10、11或12元的稠合双环或三环的环体系,其中可任选地存在至少一个羰基和/或其中所述环体系任选地被相同或不同地单取代或多取代,并且其中所述取代基可独立地选自氰基、卤素、硝基、乙酰基、羟基、氨基、SCN、三-(C1-C6)-烷基甲硅烷基、(C3-C8)-环烷基、氰基-(C3-C8)-环烷基、(C3-C8)-环烷基-(C3-C8)-环烷基、(C1-C6)-烷基-(C3-C8)-环烷基、卤代-(C3-C8)-环烷基、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-氰基烷基、(C1-C6)-羟基烷基、羟基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-氰基烯基、(C2-C6)-炔基、(C2-C6)-炔氧基-(C1-C4)-烷基、(C2-C6)-卤代炔基、(C2-C6)-氰基炔基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-卤代烷氧基-(C1-C6)-烷基、(C2-C6)-烯氧基-(C1-C6)-烷基、(C2-C6)-卤代烯氧基-(C1-C6)-烷基、(C1-C6)-氰基烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C6)-烷氧基、(C1-C6)-烷基羟基亚氨基、(C1-C6)-烷氧基亚氨基、(C1-C6)-烷基-(C1-C6)-烷氧基亚氨基、(C1-C6)-卤代烷基-(C1-C6)-烷氧基亚氨基、(C1-C6)-烷硫基、(C1-C6)-卤代烷硫基、(C1-C6)-烷氧基-(C1-C6)-烷硫基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基、(C1-C6)-卤代烷基磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基磺酰基、(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰氧基、(C1-C6)-烷基羰基、(C1-C6)-烷基羰基-(C1-C6)-烷基、(C1-C6)-烷硫基羰基、(C1-C6)-卤代烷基羰基、(C1-C6)-烷基羰基氧基、(C1-C6)-烷氧基羰基、(C1-C6)-卤代烷氧基羰基、氨基羰基、(C1-C6)-烷基氨基羰基、(C1-C6)-烷基氨基硫代羰基、二-(C1-C6)-烷基氨基羰基、二-(C1-C6)-烷基氨基硫代羰基、(C2-C6)-烯基氨基羰基、二-(C2-C6)-烯基氨基羰基、(C3-C8)-环烷基氨基羰基、(C1-C6)-烷基磺酰基氨基、(C1-C6)-烷基氨基、二-(C1-C6)-烷基氨基、氨基磺酰基、(C1-C6)-烷基氨基磺酰基、二-(C1-C6)-烷基氨基磺酰基、(C1-C6)-烷基亚砜亚胺基、氨基硫代羰基、(C1-C6)-烷基氨基硫代羰基、二-(C1-C6)-烷基氨基硫代羰基、(C3-C8)-环烷基氨基、NHCO-(C1-C6)-烷基((C1-C6)-烷基羰基氨基),
或其中所述取代基可独立地选自苯基或5或6元杂芳族环,其中所述苯基或所述环可任选地被以下基团相同或不同地单取代或多取代:C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C1-C6-卤代烷基、C2-C6-卤代烯基、C2-C6-卤代炔基、C3-C6-卤代环烷基、卤素、CN、NO2、C1-C4-烷氧基、C1-C4-卤代烷氧基,
n为0、1或2。
另外还已发现,式(I)的化合物作为农药、优选作为杀虫剂和/或杀螨剂具有非常良好的功效,并且另外通常还具有非常好的植物相容性、特别是对于作物植物的相容性。
本发明的化合物由式(I)以一般性术语定义。在上下文中提及的式中给出的优选的取代基或基团的范围在下文中说明:
构型2-1
Aa优选为–C(R8)(R9)-,
Ab优选为–C(R10)(R11)-,
Ac优选为–C(R12)(R13)-,
Ad优选为–C(R14)(R15)-,
R1优选为(C1-C4)-烷基、(C1-C4)-羟基烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C1-C4)卤代烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)烯氧基-(C1-C4)烷基、(C2-C4)卤代烯氧基-(C1-C4)烷基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)炔氧基-(C1-C4)烷基、(C2-C4)卤代炔氧基-(C1-C4)烷基、(C2-C4)卤代炔基、(C2-C4)氰基炔基、(C3-C6)环烷基、(C3-C6)环烷基(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、(C1-C4)烷基氨基、二-(C1-C4)烷基氨基、(C3-C6)环烷基氨基、(C1-C4)烷基羰基氨基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)卤代烷硫基-(C1-C4)烷基、(C1-C4)烷基亚磺酰基-(C1-C4)烷基、(C1-C4)卤代烷基亚磺酰基-(C1-C4)烷基、(C1-C4)烷基磺酰基-(C1-C4)烷基、(C1-C4)烷基羰基-(C1-C4)烷基、(C1-C4)卤代烷基羰基-(C1-C4)烷基、(C1-C4)烷基磺酰基氨基,
R8、R9、R10、R11、R12、R13、R14、R15优选独立地为氢、氰基、卤素、硝基、乙酰基、羟基、氨基、SCN、三-(C1-C4)烷基甲硅烷基、(C3-C6)环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、氰基-(C3-C6)-环烷基、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C1-C4)羟基烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C2-C4)氰基炔基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C1-C4)氰基烷氧基、(C1-C4)烷氧基-(C1-C4)烷氧基、(C1-C4)烷基羟基亚氨基、(C1-C4)烷氧基亚氨基、(C1-C4)烷基-(C1-C4)烷氧基亚氨基、(C1-C4)卤代烷基-(C1-C4)烷氧基亚氨基、(C1-C4)烷硫基、(C1-C4)卤代烷硫基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)烷基亚磺酰基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)烷基亚磺酰基-(C1-C4)烷基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、(C1-C4)烷基磺酰基-(C1-C4)烷基、(C1-C4)烷基磺酰氧基、(C1-C4)烷基羰基、(C1-C4)卤代烷基羰基、氨基羰基、(C1-C4)烷基氨基羰基、二-(C1-C4)烷基氨基羰基、(C1-C4)烷基磺酰基氨基、(C1-C4)烷基氨基、二-(C1-C4)烷基氨基、氨基磺酰基、(C1-C4)烷基氨基磺酰基、二-(C1-C4)烷基氨基磺酰基、氨基硫代羰基、NHCO-(C1-C4)烷基((C1-C4)烷基羰基氨基),
以及优选为苯基或杂芳基,其各自任选地被相同或不同地单取代或双取代,其中(在杂芳基的情况下)可任选地存在至少一个羰基和/或其中在每种情况下的可能的取代基如下:氰基、卤素、硝基、乙酰基、氨基、(C3-C6)环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C1-C4)羟基烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C2-C4)氰基炔基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C1-C4)氰基烷氧基、(C1-C4)烷氧基-(C1-C4)烷氧基、(C1-C4)烷基羟基亚氨基、(C1-C4)烷氧基亚氨基、(C1-C4)烷基-(C1-C4)烷氧基亚氨基、(C1-C4)卤代烷基-(C1-C4)烷氧基亚氨基、(C1-C4)烷硫基、(C1-C4)卤代烷硫基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)烷基亚磺酰基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)烷基亚磺酰基-(C1-C4)烷基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、(C1-C4)烷基磺酰基-(C1-C4)烷基、(C1-C4)烷基磺酰氧基、(C1-C4)烷基羰基、(C1-C4)卤代烷基羰基、氨基羰基、(C1-C4)烷基氨基羰基、二-(C1-C4)烷基氨基羰基、(C1-C4)烷基磺酰基氨基、(C1-C4)烷基氨基、二-(C1-C4)烷基氨基、氨基磺酰基、(C1-C4)烷基氨基磺酰基、二-(C1-C4)烷基氨基磺酰基、NHCO-(C1-C4)烷基((C1-C4)烷基羰基氨基),
Q优选为杂芳族的8、9、10、11或12元的稠合双环或三环的环体系,其中可任选地存在至少一个羰基和/或其中所述环体系任选地被相同或不同地单取代或多取代,并且其中所述取代基可独立地选自:氰基、卤素、硝基、乙酰基、羟基、氨基、SCN、三-(C1-C6)-烷基甲硅烷基、(C3-C8)-环烷基、氰基-(C3-C8)-环烷基、(C3-C8)-环烷基-(C3-C8)-环烷基、(C1-C6)-烷基-(C3-C8)-环烷基、卤代-(C3-C8)-环烷基、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-氰基烷基、(C1-C6)-羟基烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-氰基烯基、(C2-C6)-炔基、(C2-C6)-炔氧基-(C1-C4)-烷基、(C2-C6)-卤代炔基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-卤代烷氧基-(C1-C6)-烷基、(C2-C6)-烯氧基-(C1-C6)-烷基、(C2-C6)-卤代烯氧基-(C1-C6)-烷基、(C1-C6)-氰基烷氧基、(C1-C6)-烷氧基-(C1-C6)-烷氧基、(C1-C6)-烷基羟基亚氨基、(C1-C6)-烷氧基亚氨基、(C1-C6)-烷基-(C1-C6)-烷氧基亚氨基、(C1-C6)-烷硫基、(C1-C6)-卤代烷硫基、(C1-C6)-烷氧基-(C1-C6)-烷硫基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基、(C1-C6)-卤代烷基磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基磺酰基、(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰氧基、(C1-C6)-烷基羰基、(C1-C6)-烷基羰基-(C1-C6)-烷基、(C1-C6)-烷硫基羰基、(C1-C6)-卤代烷基羰基、(C1-C6)-烷基羰基氧基、(C1-C6)-烷氧基羰基、(C1-C6)-卤代烷氧基羰基、氨基羰基、(C1-C6)-烷基氨基羰基、(C1-C6)-烷基氨基硫代羰基、二-(C1-C6)-烷基氨基羰基、二-(C1-C6)-烷基氨基硫代羰基、(C3-C8)-环烷基氨基羰基、(C1-C6)-烷基磺酰基氨基、(C1-C6)-烷基氨基、二-(C1-C6)-烷基氨基、氨基磺酰基、(C1-C6)-烷基氨基磺酰基、二-(C1-C6)-烷基氨基磺酰基、(C1-C6)-烷基亚砜亚胺基、氨基硫代羰基、(C1-C6)-烷基氨基硫代羰基、二-(C1-C6)-烷基氨基硫代羰基、(C3-C8)-环烷基氨基、NHCO-(C1-C6)-烷基((C1-C6)-烷基羰基氨基),或其中所述取代基可独立地选自苯基或5或6元杂芳族环,其中所述苯基或所述环可任选地被以下基团相同或不同地单取代或多取代:C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C1-C6-卤代烷基、C2-C6-卤代烯基、C2-C6-卤代炔基、C3-C6-卤代环烷基、卤素、CN、C1-C4-烷氧基、C1-C4-卤代烷氧基,
n优选为0、1或2。
构型3-1
Aa更优选为–C(R8)(R9)-,
Ab更优选为–C(R10)(R11)-,
Ac更优选为–C(R12)(R13)-,
Ad更优选为–C(R14)(R15)-,
R1更优选为(C1-C4)烷基、(C1-C4)羟基烷基、(C1-C4)卤代烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C3-C6)环烷基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)烷基亚磺酰基-(C1-C4)烷基或(C1-C4)烷基磺酰基-(C1-C4)烷基,
R8、R9、R10、R11、R12、R13、R14、R15更优选独立地为氢、氰基、卤素、硝基、羟基、氨基、SCN、三-(C1-C4)烷基甲硅烷基、(C3-C6)环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、氰基-(C3-C8)环烷基、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C2-C4)氰基炔基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C1-C4)氰基烷氧基、(C1-C4)烷基羟基亚氨基、(C1-C4)烷氧基亚氨基、(C1-C4)烷基-(C1-C4)烷氧基亚氨基、(C1-C4)烷硫基、(C1-C4)卤代烷硫基、(C1-C4)烷基亚磺酰基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、(C1-C4)烷基磺酰氧基、(C1-C4)烷基羰基、(C1-C4)卤代烷基羰基、氨基羰基、(C1-C4)烷基氨基羰基、二-(C1-C4)烷基氨基羰基、(C1-C4)烷基磺酰基氨基、(C1-C4)烷基氨基、二-(C1-C4)烷基氨基、氨基磺酰基、(C1-C4)烷基氨基磺酰基、二-(C1-C4)烷基氨基磺酰基、NHCO-(C1-C4)烷基((C1-C4)烷基羰基氨基),
以及更优选为苯基或杂芳基,其各自任选地被相同或不同地单取代或双取代,其中(在杂芳基的情况下)可任选地存在至少一个羰基和/或其中在每种情况下可能的取代基如下:氰基、卤素、(C3-C6)环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C2-C4)氰基炔基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C1-C4)烷基羟基亚氨基、(C1-C4)烷氧基亚氨基、(C1-C4)烷基-(C1-C4)烷氧基亚氨基、(C1-C4)烷硫基、(C1-C4)卤代烷硫基、(C1-C4)烷基亚磺酰基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、(C1-C4)烷基磺酰氧基、(C1-C4)烷基羰基、(C1-C4)卤代烷基羰基、氨基羰基、(C1-C4)烷基氨基羰基、二-(C1-C4)烷基氨基羰基、(C1-C4)烷基磺酰基氨基、(C1-C4)烷基氨基、二-(C1-C4)烷基氨基、氨基磺酰基、(C1-C4)烷基氨基磺酰基、二-(C1-C4)烷基氨基磺酰基、NHCO-(C1-C4)烷基((C1-C4)烷基羰基氨基),
Q更优选为选自Q1至Q21的杂芳族的9元或12元的稠合双环或三环的环体系:
R4更优选为(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-氰基烷基、(C1-C4)-羟基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-卤代烷氧基-(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-烯氧基-(C1-C4)-烷基、(C2-C4)-卤代烯氧基-(C1-C4)-烷基、(C2-C4)-卤代烯基、(C2-C4)氰基烯基、(C2-C4)-炔基、(C2-C4)-炔氧基-(C1-C4)-烷基、(C2-C4)-卤代炔基、(C3-C6)-环烷基、(C3-C6)-环烷基-(C3-C6)-环烷基、(C1-C4)-烷基-(C3-C6)-环烷基、卤代-(C3-C6)-环烷基、(C1-C4)-烷硫基-(C1-C4)-烷基、(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基、(C1-C4)-烷基磺酰基-(C1-C4)-烷基或(C1-C4)-烷基羰基-(C1-C4)-烷基,
R5、R6更优选独立地为氢、氰基、卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C2-C4)-烯基、(C2-C4)-卤代烯基、(C2-C4)-炔基、(C2-C4)-卤代炔基、(C3-C6)-环烷基、氰基-(C3-C6)-环烷基、(C3-C6)-环烷基-(C3-C6)-环烷基、(C1-C4)-烷基-(C3-C6)-环烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷氧基亚氨基、(C1-C4)-烷硫基、(C1-C4)-卤代烷硫基、(C1-C4)-烷基亚磺酰基、(C1-C4)-卤代烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C1-C4)-卤代烷基磺酰基、(C1-C4)-烷基磺酰氧基、(C1-C4)-烷基羰基、(C1-C4)-卤代烷基羰基、氨基羰基、(C1-C4)-烷基氨基羰基、二-(C1-C4)-烷基氨基羰基、(C1-C4)-烷基磺酰基氨基、(C1-C4)-烷基氨基、二-(C1-C4)-烷基氨基、氨基磺酰基、(C1-C4)-烷基氨基磺酰基或二-(C1-C4)-烷基氨基磺酰基,
R7更优选为氢、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C1-C4)羟基烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C1-C4)卤代烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)烯氧基-(C1-C4)烷基、(C2-C4)卤代烯氧基-(C1-C4)烷基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C3-C6)环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)烷基亚磺酰基-(C1-C4)烷基或(C1-C4)烷基磺酰基-(C1-C4)烷基,
n更优选为0、1或2。
构型4-1
Aa甚至更优选为–C(R8)(R9)-,
Ab甚至更优选为–C(R10)(R11)-,
Ac甚至更优选为–C(R12)(R13)-,
Ad甚至更优选为–C(R14)(R15)-,
R1甚至更优选为甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、叔丁基、环丁基、氟甲基、二氟甲基、三氟甲基、氟乙基、二氟乙基、三氟乙基、四氟乙基或五氟乙基,
R8、R9、R10、R11、R12、R13、R14、R15甚至更优选独立地为氢、氰基、卤素、(C1-C4)烷基、(C3-C6)-环烷基、氰基-(C3-C6)-环烷基、(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)烷基亚磺酰基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷硫基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)卤代烷基磺酰基或NHCO-(C1-C4)烷基((C1-C4)烷基羰基氨基),
Q甚至更优选为选自以下的杂芳族的9元或12元的稠合双环或三环的环体系:Q2、Q3、Q4、Q10、Q11、Q14、Q15、Q16、Q19、Q20或Q21,
R4甚至更优选为(C1-C4)-烷基或(C1-C4)-烷氧基-(C1-C4)-烷基,
R5甚至更优选为氢、氰基、卤素、(C1-C4)烷基、(C1-C4)卤代烷基、(C3-C6)环烷基、氰基-(C3-C6)-环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C1-C4)烷氧基亚氨基、(C1-C4)烷硫基、(C1-C4)卤代烷硫基、(C1-C4)烷基亚磺酰基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、(C1-C4)烷基羰基、(C1-C4)卤代烷基羰基、(C1-C4)烷基氨基羰基、二-(C1-C4)烷基氨基羰基、(C1-C4)烷基磺酰基氨基、(C1-C4)烷基氨基磺酰基或二-(C1-C4)烷基氨基磺酰基,
R6甚至更优选为氢或甲基,
R7甚至更优选为氢、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C1-C4)卤代烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C3-C6)环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)烷基亚磺酰基-(C1-C4)烷基或(C1-C4)烷基磺酰基-(C1-C4)烷基,
n甚至更优选为0、1或2。
构型5-1
Aa特别是–C(R8)(R9)-,
Ab特别是–C(R10)(R11)-,
Ac特别是–C(R12)(R13)-,
Ad特别是–C(R14)(R15)-,
R1特别是甲基、乙基、正丙基、异丙基或环丙基,
R8、R9、R10、R11、R12、R13、R14、R15特别地独立地为氢、氰基、环丙基、环丁基、氰基环丙基、氟、氯、溴、甲基、乙基、三氟甲基、二氟甲基、三氟乙基、甲氧基或乙氧基,
Q特别是选自以下的杂芳族的9元稠合双环的环体系:Q2、Q3、Q4、Q10、Q14、Q16或Q21,
R4特别是甲基、乙基、异丙基、甲氧基甲基或甲氧基乙基,
R5特别是氟、氯、溴、氟甲基、二氟甲基、三氟甲基、氟乙基(CH2CFH2、CHFCH3)、二氟乙基(CF2CH3、CH2CHF2、CHFCFH2)、三氟乙基(CH2CF3、CHFCHF2、CF2CFH2)、四氟乙基(CHFCF3、CF2CHF2)、五氟乙基、三氟甲氧基、二氟氯甲氧基、二氯氟甲氧基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基或氰基环丙基,
R6特别是氢,
R7特别是甲基、乙基、异丙基、环丙基、甲氧基甲基或甲氧基乙基,
n特别是0、1或2。
构型6-1
Aa尤其是–C(R8)(R9)-,
Ab尤其是–C(R10)(R11)-,
Ac尤其是–C(R12)(R13)-,
Ad尤其是–C(R14)(R15)-,
R1尤其是乙基,
R8尤其是氢,
R9尤其是氢,
R10尤其是氢或甲基,
R11尤其是氢,
R12尤其是氢、甲基或三氟甲基,
R13尤其是氢,
R14尤其是氢,
R15尤其是氢,
Q尤其是选自Q2或Q3的杂芳族的9元稠合双环环体系,
R4尤其是甲基,
R5尤其是三氟甲基、五氟乙基、三氟甲氧基、三氟甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基,
R6尤其是氢,
n尤其是2。
构型6-2
Aa尤其是–C(R8)(R9)-,
Ab尤其是–C(R10)(R11)-,
Ac尤其是–C(R12)(R13)-,
Ad尤其是–C(R14)(R15)-,
R1尤其是乙基,
R8尤其是氢,
R9尤其是氢,
R10尤其是氢、甲基或三氟甲基,
R11尤其是氢,
R12尤其是氢、甲基或三氟甲基,
R13尤其是氢,
R14尤其是氢,
R15尤其是氢,
Q尤其是选自Q2、Q3、Q4或Q21的杂芳族的9元稠合双环环体系,
R4尤其是甲基,
R5尤其是三氟甲基、五氟乙基、三氟甲氧基、三氟甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基,
R6尤其是氢,
R7尤其是甲基,
n尤其是2。
在一个优选的实施方案中,本发明涉及式(I)的化合物,其中Q为Q2,并且Aa、Ab、Ac、Ad、R1、R4、R5、R6、R8、R9、R10、R11、R12、R13、R14、R15和n具有在构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)或构型(6-1)或构型(6-2)中记载的定义。
在一个优选的实施方案中,本发明涉及式(I)的化合物,其中Q为Q3,并且Aa、Ab、Ac、Ad、R1、R4、R5、R6、R8、R9、R10、R11、R12、R13、R14、R15和n具有在构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)或构型(6-1)或构型(6-2)中记载的定义。
在一个优选的实施方案中,本发明涉及式(I)的化合物,其中Q为Q4,并且Aa、Ab、Ac、Ad、R1、R5、R6、R8、R9、R10、R11、R12、R13、R14、R15和n具有在构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)或构型(6-1)或构型(6-2)中记载的定义。
在一个优选的实施方案中,本发明涉及式(I)的化合物,其中Q为Q21,并且Aa、Ab、Ac、Ad、R1、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15和n具有在构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)或构型(6-1)或构型(6-2)中记载的定义。
在一个优选的实施方案中,本发明涉及式(I)的化合物,其中R8、R9、R10、R11、R12、R13、R14、R15为氢,并且Q、Aa、Ab、Ac、Ad、R1、R4、R5、R6、R7和n具有在构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)或构型(6-1)或构型(6-2)中记载的定义。
在一个优选的实施方案中,本发明涉及式(I)的化合物,其中R8、R9、R10、R11、R13、R14、R15为氢,R12为三氟甲基,并且Q、Aa、Ab、Ac、Ad、R1、R4、R5、R6、R7和n具有在构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)或构型(6-1)或构型(6-2)中记载的定义。
在一个优选的实施方案中,本发明涉及式(I)的化合物,其中R8、R9、R10、R11、R13、R14、R15为氢,R12为甲基,并且Q、Aa、Ab、Ac、Ad、R1、R4、R5、R6、R7和n具有在构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)或构型(6-1)或构型(6-2)中记载的定义。
在一个优选的实施方案中,本发明涉及式(I)的化合物,其中R8、R9、R11、R12、R13、R14、R15为氢,R10为甲基,并且Q、Aa、Ab、Ac、Ad、R1、R4、R5、R6、R7和n具有在构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)或构型(6-1)或构型(6-2)中记载的定义。
在一个优选的实施方案中,本发明涉及式(I)的化合物,其中R8、R9、R11、R12、R13、R14、R15为氢,R10为三氟甲基,并且Q、Aa、Ab、Ac、Ad、R1、R4、R5、R6、R7和n具有在构型(1-1)或构型(2-1)或构型(3-1)或构型(4-1)或构型(5-1)或构型(6-1)或构型(6-2)中记载的定义。
在这些优选的定义中,除非另有说明,
卤素选自氟、氯、溴和碘,又优选选自氟、氯和溴。
芳基(包括作为较大的单元例如芳基烷基的一部分的芳基)选自:苯基、苄基、萘基、蒽基、菲基,并且又优选苯基,
杂芳基(hetaryl)(与杂芳基(heteroaryl)同义,包括作为较大单元例如杂芳基烷基的一部分的杂芳基)选自:呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,5-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、四唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、苯并呋喃基、苯并异呋喃基、苯并噻吩基、苯并异噻吩基、吲哚基、异吲哚基、吲唑基、苯并噻唑基、苯并异噻唑基、苯并噁唑基、苯并异噁唑基、苯并咪唑基、2,1,3-苯并噁二唑基、喹啉基、异喹啉基、噌啉基(cinnolinyl)、酞嗪基、喹唑啉基、喹喔啉基、萘啶基、苯并三嗪基、嘌呤基、蝶啶基和吲嗪基(indolizinyl),
杂环基是含有1或2个氮原子和/或一个氧原子和/或一个硫原子的饱和的4、5或6元环,例如氮杂环丁基(azetidinyl)、吡咯烷基、哌啶基、氧杂环丁基(oxetanyl)、四氢呋喃基、四氢吡喃基、二氧杂环己基(dioxanyl)、硫杂环丁基(thietanyl)、四氢噻吩基(tetrahydrothiophenyl)、四氢噻喃基、哌嗪基、吗啉基和硫代吗啉基。
在特别优选的定义中,除非另有说明,
卤素选自氟、氯、溴和碘,又优选选自氟、氯和溴。
芳基(包括作为较大的单元例如芳基烷基的一部分的芳基)选自:苯基、苄基、萘基、蒽基、菲基,并且又优选苯基,
杂芳基(包括作为较大单元例如杂芳基烷基的一部分的杂芳基)选自:吡啶基、嘧啶基、吡嗪基、哒嗪基、吡唑基、咪唑基、三唑基、噻唑基和四唑基,
杂环基选自氧杂环丁基、四氢呋喃基和哌嗪基。
在本发明的上下文中,除非另有不同定义,术语“烷基”——其本身或与其他术语结合,例如卤代烷基——应理解为意指饱和脂族烃基的基团,其具有1至12个碳原子并且可以是支链的或直链的。C1-C12-烷基基团的实例为甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基、1-甲基丁基、2-甲基丁基、1-乙基丙基、1,2-二甲基丙基、己基、正庚基、正辛基、正壬基、正癸基、正十一烷基和正十二烷基。在这些烷基基团中,特别优选C1-C6-烷基基团。特别优选C1-C4-烷基基团。
根据本发明,除非另有不同定义,术语“烯基”——其本身或与其他术语结合——应理解为意指具有至少一个双键的直链或支链的C2-C12-烯基基团,例如乙烯基、烯丙基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1,3-丁二烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1,3-戊二烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基和1,4-己二烯基。在这些基团中,优选C2-C6-烯基基团,特别优选C2-C4-烯基基团。
根据本发明,除非另有不同定义,术语“炔基”——其本身或与其他术语结合——应理解为意指具有至少一个三键的直链或支链的C2-C12-炔基基团,例如乙炔基、1-丙炔基和炔丙基。在这些基团中,优选C3-C6-炔基基团,特别优选C3-C4-炔基基团。炔基基团还可含有至少一个双键。
根据本发明,除非另有不同定义,术语“环烷基”——其本身或与其他术语结合——应理解为意指C3-C8-环烷基基团,例如环丙基、环丁基、环戊基、环己基、环庚基和环辛基。在这些基团中,优选C3-C6-环烷基基团。
术语“烷氧基”——其本身或与其他术语结合,例如卤代烷氧基——在本案中理解为意指O-烷基基团,其中术语“烷基”如上文所定义。
卤素取代的基团,例如卤代烷基,为单卤代或多卤代的,最高达可能的取代基的最大数目。在多卤代的情况下,卤素原子可以是相同的或不同的。这里的卤素是氟、氯、溴或碘,特别是氟、氯或溴。
除非另有说明,任选取代的基团可以是单取代或多取代的,其中在多取代的情况下,取代基可以是相同的或不同的。
以一般性术语给出或在优选范围内列出的基团定义或说明相应地适用于最终产物,并且适用于起始材料和中间体。这些基团定义可以根据需要彼此组合,即包括各自优选范围之间的组合。
根据本发明优选使用式(I)的化合物,其含有上文列为优选的含义的组合。
根据本发明特别优选使用式(I)的化合物,其含有上文列为特别优选的含义的组合。
根据本发明非常特别优选使用式(I)的化合物,其含有上文列为非常特别优选的定义的组合。
根据本发明最优选使用式(I)的化合物,其含有上文列为最优选的含义的组合。
根据本发明,特别地使用式(I)的化合物,其含有上文列为特别强调的的含义的组合。
根据取代基的性质,式(I)的化合物可为几何异构体和/或光学活性异构体或相应的不同组成的异构体混合物的形式。这些立体异构体为例如对映异构体、非对映异构体、阻转异构体或几何异构体。因此,本发明包括纯的立体异构体和这些异构体的任何期望的混合物。
本发明的式(I)的化合物可通过以下方案中所示的方法获得:
方法A-1
其中Q为Q1至Q9、Q19和Q21的式(I)的化合物可通过已知方法制备,例如类似于在WO2009/131237、WO2010/125985、WO2011/043404、WO2011/040629、WO2012/086848、WO2013/018928、WO2015/000715、WO2015/121136、WO2016/124563、WO2016/124557、WO2017/001311、WO2017/001314、WO2017/061497、WO2017/084879、WO2017/089190、WO2017/133994中记载的方法。
基团R1、R4、R5、R6、R7、Aa、Ab、Ac、Ad和n具有上文中记载的定义,A2和A3为CH或N,A4为O、S或N-R4,并且X1为卤素。
对于其中Q为Q21的式(I)的化合物,A2为羰基且A3为N-R7。
步骤a)
式(IV)的化合物可类似于US5576335中记载的方法,通过使式(II)的化合物与式(III)的羧酸在缩合剂或碱的存在下反应来制备。
式(II)的化合物是市售可得的或可通过已知方法制备,例如类似于US2003/69257、WO2006/65703、WO2009/131237、WO2010/125985、WO2011/043404、WO2011/040629、WO2012/086848、WO2013/018928、WO2015/000715、WO2016/091731、WO2016/142326、WO2016/169882、WO2016/23954或WO2017/84879中记载的方法。
式(III)的羧酸是市售可得的或可通过已知方法制备。可能的制备路线记载于方法E中。
式(II)的化合物与式(III)的羧酸的反应可以不用溶剂或在溶剂中进行,优选在选自常规溶剂的溶剂中进行该反应,所述常规溶剂在反应条件下是惰性的。优选醚类,例如二异丙基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷;卤代烃类,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;腈类,例如乙腈或丙腈;芳族烃类,例如甲苯或二甲苯;非质子极性溶剂,例如N,N-二甲基甲酰胺或N-甲基吡咯烷酮,或含氮化合物,例如吡啶。
合适的缩合剂为例如碳二亚胺,如1-(3-二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐(EDCI)或1,3-二环己基碳二亚胺。
合适的碱是通常用于这类反应中的无机碱。优选使用选自例如碱金属或碱土金属的乙酸盐、磷酸盐、碳酸盐和碳酸氢盐的碱。本文中,特别优选乙酸钠、磷酸钠、磷酸钾、碳酸铯、碳酸钠、碳酸钾、碳酸氢钠、碳酸氢钾。
该反应可以在减压下、在标准压力下或在高压下,和在0℃至180℃的温度下进行;优选所述反应在标准压力下和在20至140℃的温度下进行。
步骤b)
式(V)的化合物可通过使式(IV)的化合物缩合来制备,例如类似于WO2009/131237、WO2010/125985、WO2011/043404、WO2011/040629、WO2012/086848、WO2013/018928、WO2015/000715或WO 2015/121136中记载的方法。
向式(V)的化合物的转化可以不用溶剂或在溶剂中进行,优选在选自常规溶剂的溶剂中进行该反应,所述常规溶剂在反应条件下是惰性的。优选醚类,例如二异丙基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、叔丁基甲基醚;卤代烃类,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;腈类,例如乙腈或丙腈;芳族烃类,例如甲苯或二甲苯;非质子极性溶剂,例如N,N-二甲基甲酰胺或N-甲基吡咯烷酮,或含氮化合物,例如吡啶。
该反应可在缩合剂、酸、碱或氯化剂的存在下进行。
合适的缩合剂的实例是碳二亚胺,如1-(3-二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐(EDCI)或1,3-二环己基碳二亚胺;酸酐,如乙酸酐、三氟乙酸酐;三苯基膦、碱和四氯化碳的混合物;或三苯基膦和偶氮二酯(例如偶氮二羧酸二乙酯)的混合物。
可用于所述反应中的合适的酸的实例为磺酸如对甲苯磺酸;羧酸如乙酸,或多磷酸。
合适的碱的实例为氮杂环化合物,如吡啶、甲基吡啶、2,6-二甲基吡啶、1,8-二氮杂双环[5.4.0]-7-十一碳烯(DBU);叔胺,如三乙胺和N,N-二异丙基乙胺;无机碱,如磷酸钾、碳酸钾和氢化钠。
合适的氯化剂的实例为三氯氧磷。
该反应可以在减压下、在标准压力下或在高压下和在0℃至200℃的温度下进行。
步骤c)
其中n为0的式(I)的化合物可通过使式(V)的化合物与式(VIa)的化合物,在碱的存在下反应来制备。
式(VIa)的硫醇衍生物,例如甲硫醇、乙硫醇或异丙硫醇是市售可得的或可通过已知方法制备,例如类似于在US2006/25633、US2006/111591、US2820062、ChemicalCommunications,13(2000),1163-1164或Journal of the American Chemical Society,44(1922),第1329页中记载的方法。
向其中n为0的式(I)的化合物的转化可以不用溶剂或在溶剂中进行,优选在选自常规溶剂的溶剂中进行该反应,所述常规溶剂在反应条件下是惰性的。优选醚类,例如二异丙基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、叔丁基甲基醚;腈类,例如乙腈或丙腈;芳族烃类,例如甲苯或二甲苯;非质子极性溶剂,例如N,N-二甲基甲酰胺、N-甲基吡咯烷酮或二甲基亚砜。
合适的碱的实例为选自碱金属或碱土金属的乙酸盐、磷酸盐和碳酸盐的无机碱。在这里优选碳酸铯、碳酸钠和碳酸钾。其他合适的碱是碱金属氢化物,例如氢化钠。
该反应可以在减压下、在标准压力下或在高压下和在0℃至200℃的温度下进行。
在上述反应中,X1优选为氟或氯原子。
如果X1为溴或碘,则另一替代方法是使用合适的锂碱进行转金属化反应(transmetallation),随后与合适的市售可得的二硫化物反应;参见Bioorganic andMedicinal Chemistry Letters,20(2010),2770–2775。
此外,如果X1为溴或碘,则可类似于在JP2017/25059中记载的方法,使用合适的钯催化剂(例如双(二亚苄基丙酮)钯(0))在合适的配体(例如4,5-双(二苯基膦基)-9,9-二甲基氧杂蒽(Xantphos))的存在下以及在合适的碱(例如N,N-二异丙基乙胺)的存在下,引入式(VIa)的硫醇衍生物。该反应在溶剂中、优选在醚例如二噁烷中进行。
步骤d)
其中n为1的式(I)的化合物可通过氧化其中n为0的式(I)的化合物来制备。氧化通常在选自常规溶剂的溶剂中进行,所述常规溶剂在反应条件下是惰性的。优选卤代烃类,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;醇类,如甲醇或乙醇;甲酸、乙酸、丙酸或水。
合适的氧化剂的实例为过氧化氢、间氯过氧苯甲酸或高碘酸钠。
该反应可以在减压下、在标准压力下或在高压下和在-20℃至120℃的温度下进行。
步骤e)
其中n为2的式(I)的化合物可通过氧化其中n为1的式(I)的化合物来制备。氧化通常在溶剂中进行。优选卤代烃类,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;醇类,如甲醇或乙醇;甲酸、乙酸、丙酸或水。
合适的氧化剂的实例是过氧化氢和间氯过氧苯甲酸。
该反应可以在减压下、在标准压力下或在高压下和在-20℃至120℃的温度下进行。
步骤f)
其中n为2的式(I)的化合物也可以以一步法通过氧化其中n为0的式(I)的化合物来制备。氧化通常在溶剂中进行。优选卤代烃类,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;醇类,如甲醇或乙醇;甲酸、乙酸、丙酸或水。
合适的氧化剂的实例是过氧化氢和间氯过氧苯甲酸。
该反应可以在减压下、在标准压力下或在高压下和在-20℃至120℃的温度下进行。
方法A-2
其中n为2且Q为Q1至Q9、Q19和Q21的式(I)的化合物可通过已知方法制备,例如类似于在WO2009/131237、WO2010/125985、WO2011/043404、WO2011/040629、WO2012/086848、WO2013/018928、WO2015/000715和WO2015/121136中记载的方法。
基团R1、R4、R5、R6、R7、Aa、Ab、Ac、Ad、A2和A3具有上文记载的定义,A4为O、S或N-R4,且X1为卤素,优选溴或碘。
对于其中Q为Q21的式(I)的化合物,A2为羰基且A3为N-R7。
步骤a)
或者,其中n为2的式(II)的化合物也可以一步法制备,从式(V)的化合物开始,通过与式(VIb)的化合物的卤素-砜交换反应制备,例如类似于在Journal of OrganicChemistry 2005,70,2696-2700中记载的方法。该交换反应通常在溶剂中进行。优选使用极性非质子溶剂,例如二甲基亚砜或N,N-二甲基甲酰胺。
式(VIb)的化合物是市售可得的或可通过已知方法制备,例如类似于在OrganicSynthesis 1977,57,88-92;Tetrahedron Letters 1979,9,821-824和Bulletin de laSociete Chimique de France 1958,4,447-450中记载的方法。
合适的硫试剂的实例为亚磺酸的锂盐、钠盐或钾盐。
该反应可以在减压下、在标准压力下或在高压下和在-20℃至120℃的温度下进行。
方法B
其中Q代表Q10、Q11、Q14或Q15的式(I)的化合物可通过已知方法制备,例如类似于在US2009/203705、US2012/258951、WO2013/3298或J.Med.Chem.31,(1988)1590-1595中记载的方法。
基团R1、R5、R6、Aa、Ab、Ac、Ad和n具有上文中记载的定义。A2、A3、A4和A5为CH或N(其中A2、A3、A4和A5不全是N)且X1为卤素。
步骤a)
类似于在WO2015/107117、WO2011/75643或EP2671582中记载的方法,将式(III)的羧酸在O,N-二甲基羟胺盐酸盐的存在下转化成式(VI)的Weinreb酰胺。
式(III)的羧酸是市售可得的或可通过已知方法制备。可能的制备路线记载于方法E中。
步骤b)、c)
然后可使用格林试剂(例如甲基溴化镁)通过已知方法(例如类似于在WO2011/75643中记载的方法)将式(VI)的化合物转化成式(VII)的酮。式(VIII)的化合物可类似于例如在US2012/302573中记载的已知方法通过随后的卤化反应获得。
步骤d)
式(X)的化合物可通过用式(IX)的胺环化式(VIII)的化合物制备。环化通过类似于例如在WO2005/66177、WO2012/88411、WO2013/3298、US2009/203705、US2012/258951、WO2012/168733、WO2014/187762或J.Med.Chem.31(1988)1590-1595中记载的已知方法例如在乙醇、乙腈或N,N-二甲基甲酰胺中进行。
式(IX)的化合物是市售可得的。
步骤e)
其中n为0的式(I)的化合物可通过使式(X)的化合物与式(VIa)的化合物,在碱的存在下反应来制备。式(VIa)的硫醇衍生物,例如甲硫醇、乙硫醇或异丙硫醇是市售可得的或可通过已知方法制备,例如类似于在US2006/25633、US2006/111591、US2820062、Chemical Communications,13(2000),1163-1164或Journal of the American ChemicalSociety,44(1922),第1329页中记载的方法。
如果X1为溴或碘,则另一替代方法是使用合适的锂碱进行转金属化反应,随后与合适的市售可得的二硫化物反应;参见Bioorganic and Medicinal Chemistry Letters,20(2010),2770–2775。
此外,如果X1为溴或碘,则可类似于在JP2017/25059中记载的方法,使用合适的钯催化剂(例如双(二亚苄基丙酮)钯(0))在合适的配体(例如4,5-双(二苯基膦基)-9,9-二甲基氧杂蒽(Xantphos))的存在下以及在合适的碱(例如N,N-二异丙基乙胺)的存在下引入式(VIa)的硫醇衍生物。该反应在溶剂中、优选在醚例如二噁烷中进行。
步骤f)、g)
其中n为1的式(I)的化合物可通过氧化其中n为0的式(I)的化合物制备。氧化使用合适的氧化剂例如过氧化氢、间氯过氧苯甲酸或高碘酸钠通过已知方法进行。
其中n为2的式(I)的化合物可通过氧化其中n为1的式(I)的化合物制备。
氧化通常在溶剂中进行。优选卤代烃类,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;醇类,如甲醇或乙醇;甲酸、乙酸、丙酸或水。合适的氧化剂的实例是过氧化氢和间氯过氧苯甲酸。
步骤h)
其中n为2的式(I)的化合物也可通过氧化其中n为0的式(I)的化合物以一步法制备。氧化通常在溶剂中进行。优选卤代烃类,例如二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷或氯苯;醇类,如甲醇或乙醇;甲酸、乙酸、丙酸或水。合适的氧化剂的实例是过氧化氢和间氯过氧苯甲酸。
方法C
其中Q为Q16的式(I)的化合物可通过已知方法制备,例如类似于在WO2014/142292中记载的方法。
基团R4、R5、R6、Aa、Ab、Ac和Ad具有上文中记载的定义。X1为卤素。
步骤a)
式(XI)的化合物可类似于在US5374646或Bioorganic and Medicinal ChemistryLetters 2003,13,1093-1096中记载的方法,通过在缩合剂的存在下,使式(III)的化合物与氨源反应而制备。
式(III)的羧酸是市售可得的或可通过已知方法制备。可能的制备路线记载于方法E中。
在大多数情况下,所使用的氨源为氢氧化铵。
式(III)的化合物与氨源的反应优选在选自常规溶剂的溶剂中进行,所述常规溶剂在反应条件下是惰性的。优选醚类,例如二噁烷或四氢呋喃。
合适的缩合剂的实例为例如羰二咪唑。
该反应可以在减压下、在大气压力下或在高压下进行。优选地,该反应在大气压力和20至70℃的温度下进行。
步骤b)
式(XIII)的化合物可类似于在WO2014/142292中记载的方法,通过使式(XI)的化合物与式(XII)的化合物在钯催化剂的存在下,在碱性介质中反应而制备。
式(XII)的化合物可例如类似于在WO2014/142292中记载的方法制备。所使用的钯催化剂可以为例如[1,1′-双-(二苯基膦基)二茂铁]二氯化钯(II)。通常,所使用的碱为无机碱如叔丁醇钾。
反应在溶剂中进行。通常,使用甲苯。
该反应可以在减压下、在大气压力下或在高压下进行。优选地,反应在大气压力和20至110℃的温度下进行。
式(XIII)的化合物向式(I)的化合物的进一步转化类似于方法A进行。
方法D
其中Q代表Q12、Q13、Q17、Q18或Q20的式(I)的化合物可通过已知方法制备,例如类似于在WO2010/91310、WO2012/66061或WO2013/99041中记载的方法。
基团R5、R6、Aa、Ab、Ac和Ad具有上文中记载的定义,A2、A3和A6为CH或N(其中A2、A3和A6不能同时为N)。X1和X2为卤素。
步骤a)
式(XVI)的化合物可通过使式(XIV)的化合物与式(XV)的化合物在碱性条件下反应而制备,例如类似于在WO2006/19831、WO2009/127686、Chem.Eur.J.20(2014),974-978、WO2005/80388、WO2010/91310、WO2012/66061或WO2013/99041中记载的方法。
式(XIV)的化合物是市售可得的或可通过已知方法制备,例如类似于在WO2005/100353、WO2012/66061中或在European Journal of Medicinal Chemistry 45(2010),2214-2222中记载的方法。
式(XV)的化合物可通过已知方法,例如通过其中X2为卤素且X1为氢的中间体,类似于在WO2015/95788或WO2015/95792中记载的方法制备。随后X1从氢向卤素的转化使用卤化剂(例如N-氯代琥珀酰亚胺或N-溴代琥珀酰亚胺)通过已知方法,例如类似于在Synthesis47(2015),3221-3230;Bioorganic and Medicinal Chemistry Letters,27(2017)4044-4050或WO2011/50284中记载的方法进行。
所使用的碱通常为无机碱,如氢化钠、碳酸钾或碳酸铯。
向式(XVI)的化合物的转化通常在溶剂中进行,优选在腈中进行,例如乙腈或丙腈,或在非质子极性溶剂中进行,例如N,N-二甲基甲酰胺或N-甲基吡咯烷酮。
该反应可在减压下、在标准压力下或在高压下和在0℃至200℃的温度下进行。
或者,使式(XIV)的化合物与式(XV)的化合物反应以得到式(XVI)的化合物的反应也可通过钯催化的N-芳基化反应进行,例如类似于在Angewandte Chemie Int.Ed.2011,50,8944-8947中记载的方法。
式(XVI)的化合物向式(I)的化合物的进一步转化类似于方法A进行。
方法E
式(III)的羧酸是市售可得的或可通过已知方法制备,例如由式(XVII)的吡啶类似于在WO2006/15737、WO2007/108750、US2009/186902、WO2009/23179、WO2009/095253、WO2010/34738、WO2010/91411、WO2011/15343、WO2011/41713、WO2011/50284、WO2014/14874、WO2016/12896和Bioorganic and Medicinal Chemistry Letters,22(2012),3460-3466中记载的方法制备。
基团Aa、Ab、Ac和Ad具有上文中记载的定义,X-为卤离子、优选碘离子,X1为卤素且R16为(C1-C4)烷基。
步骤a)
可类似于在WO2009/095253、WO2011/15343、WO2014/14874或WO2010/34738中记载的方法,通过使式(XVII)的化合物与羟胺-O-磺酸在碱例如碳酸钾的存在下反应而将式(XVIII)的化合物转化成N-亚氨基吡啶鎓中间体,并且在第二步骤中将所述中间体在酸例如氢碘酸(HI)的存在下,在合适的溶剂例如乙醇中转化成式(XVIII)的1-氨基吡啶鎓衍生物。式(XVII)的吡啶衍生物是市售可得的。
步骤b)和c)
式(XX)的化合物可类似于在WO2009/095253、WO2011/15343、WO2014/14874或WO2010/34738中记载的方法,由式(XVIII)的化合物在与式(XIX)的炔烃的1,3-偶极环加成反应中制备。如果形成了异构体,则可通过色谱法将它们分离成单独的异构体。以这种方式,可以获得纯的异构形式的式(XX)的二酯。通过在合适的酸例如硫酸水溶液中加热,可通过脱羧反应以及同时酯官能的水解将式(XX)的化合物转化成式(XXI)的酸。
式(XIX)的化合物是市售可得的。
步骤d)
式(XXII)的化合物是市售可得的或可类似于在WO2006/15737、WO2007/108750或US2009/186902中记载的方法通过式(XXI)的化合物的加氢反应合成。
步骤e)
式(III)的化合物可通过已知方法由式(XXII)的化合物通过卤化反应制备,例如类似于在WO2009/23179、WO2010/91411、WO2011/41713、WO2011/50284、WO2016/12896和Bioorganic and Medicinal Chemistry Letters,22(2012),3460-3466中记载的方法,例如使用N-氯代琥珀酰亚胺或N-溴代琥珀酰亚胺作为卤化剂在溶剂例如二甲基甲酰胺、氯仿或乙腈中卤化。
方法和用途
本发明还涉及防治动物害虫的方法,其中可将式(I)的化合物作用于动物害虫和/或其生境。对动物害虫的防治优选在农业和林业以及材料保护中进行。这优选排除对人体或动物体进行的外科处理或治疗处理方法以及在人体或动物体上进行的诊断方法。
本发明还涉及式(I)的化合物用作农药、特别是作物保护组合物的用途。
在本申请上下文中,术语“农药”在每种情况下还总是包括术语“作物保护组合物”。
具有良好的植物耐受性、有利的恒温动物毒性和良好的环境相容性的式(I)的化合物适于保护植物和植物器官抵抗生物和非生物胁迫因素、提高采收率、改善采收材料的品质和防治在农业、园艺、畜牧业、水产养殖业、林业、园林和休闲设施、储存产品和材料保护以及卫生领域中遇到的动物害虫,尤其是昆虫、蛛形纲动物、蠕虫,尤其是线虫和软体动物。
在本专利申请的上下文中,术语“卫生”应理解为意指旨在预防疾病、尤其是感染性疾病以及用于保护人类和动物健康和/或保护环境和/或保持清洁的任意的和所有的措施、设备和方法。根据本发明,这尤其包括对例如纺织品或硬表面,尤其是由玻璃、木材、水泥、瓷、陶瓷、塑料或金属制成的表面进行清洁、消毒和杀菌以确保这些表面没有卫生害虫和/或其分泌物的措施。在这点上,本发明的保护范围优选排除施用于人体或动物体的外科处理或治疗处理方法,以及在人体或动物体上进行的诊断方法。
术语“卫生领域”涵盖其中所述卫生措施、设备和方法重要的所有区域、技术领域和工业应用,例如关于厨房、面包店、机场、浴室、泳池、百货店、旅馆、医院、厩舍、动物饲养等的卫生。
因此,术语“卫生害虫”应理解为意指一种或多种这样的动物害虫,其在卫生领域的存在是有问题的,尤其是出于健康原因。因此,一个主要目的是避免卫生领域中卫生害虫的存在和/或与其接触,或将卫生领域中卫生害虫的存在和/或与其接触限制至最小程度。这尤其可通过使用农药来实现,所述农药既可用于预防侵染也可用于预防现有侵染。还可使用防止或减少与害虫接触的制剂。卫生害虫包括例如下文中提及的生物。
因此,术语“卫生保护”涵盖保持和/或改进所述卫生措施、设备和方法的所有行为。
可将式(I)的化合物优选用作农药。其对通常敏感的且具有抗性的物种以及对全部或特定的发育阶段具有活性。上述害虫包括:
来自节肢动物门(Arthropoda)、特别是蛛形纲(Arachnida)的害虫,例如粉螨属(Acarus spp.),例如粗脚粉螨(Acarus siro),枸杞瘿螨(Aceria kuko)、柑橘瘤瘿螨(Aceria sheldoni),刺皮瘿螨属(Aculops spp.),针刺瘿螨属(Aculus spp.),例如福氏刺皮瘿螨(Aculus fockeui)、苹果刺锈螨(Aculus schlechtendali),花蜱属(Amblyommaspp.),山楂叶螨(Amphitetranychus viennensis),锐缘蜱属(Argas spp.),牛蜱属(Boophilus spp.),短须螨属(Brevipalpus spp.),例如紫红短须螨(Brevipalpusphoenicis)、Bryobia graminum、苜宿苔螨(Bryobia praetiosa),刺尾蝎属(Centruroidesspp.),皮螨属(Chorioptes spp.),鸡皮刺螨(Dermanyssus gallinae),屋尘螨(Dermatophagoides pteronyssinus),粉尘螨(Dermatophagoides farinae),革蜱属(Dermacentor spp.),始叶螨属(Eotetranychus spp.),例如核桃始叶螨(Eotetranychushicoriae)、梨上瘿螨(Epitrimerus pyri),真叶螨属(Eutetranychus spp.),例如班氏真叶螨(Eutetranychus banksi),瘿螨属(Eriophyes spp.),例如梨瘿螨(Eriophyes pyri)、家食甜螨(Glycyphagus domesticus)、红腿地螨(Halotydeus destructor),半跗线螨属(Hemitarsonemus spp.),例如茶半跗线螨(Hemitarsonemus latus)(=侧多食跗线螨(Polyphagotarsonemus latus)),璃眼蜱属(Hyalomma spp.),硬蜱属(Ixodes spp.),寇蛛属(Latrodectus spp.),斜蛛属(Loxosceles spp.),秋收恙螨(Neutrombiculaautumnalis),Nuphersa属,小爪螨属(Oligonychus spp.),例如咖啡小爪螨(Oligonychuscoffeae)、Oligonychus coniferarum、冬青小爪螨(Oligonychus ilicis)、甘蔗小爪螨(Oligonychus indicus)、芒果小爪螨(Oligonychus mangiferus)、草地小爪螨(Oligonychus pratensis)、石榴小爪螨(Oligonychus punicae)、樟小爪螨(Oligonychusyothersi),钝缘蜱属(Ornithodorus spp.),禽刺螨属(Ornithonyssus spp.),全爪螨属(Panonychus spp.),例如桔全爪螨(Panonychus citri)(=Metatetranychus citri)、苹果全爪螨(Panonychus ulmi)(=Metatetranychus ulmi)、桔芸锈螨(Phyllocoptrutaoleivora)、多趾宽叶螨(Platytetranychus multidigituli)、侧多食跗线螨(Polyphagotarsonemus latus),痒螨属(Psoroptes spp.),扇头蜱属(Rhipicephalusspp.),根螨属(Rhizoglyphus spp.),疥螨属(Sarcoptes spp.),中东金蝎(Scorpiomaurus),狭趺线螨属(Steneotarsonemus spp.),稻细螨(Steneotarsonemus spinki),跗线螨属(Tarsonemus spp.),例如乱跗线螨(Tarsonemus confusus)、白跗线螨(Tarsonemuspallidus),叶螨属(Tetranychus spp.),例如加拿大叶螨(Tetranychus canadensis)、朱砂叶螨(Tetranychus cinnabarinus)、土耳其斯坦叶螨(Tetranychus turkestani)、二斑叶螨(Tetranychus urticae)、阿氏真恙螨(Trombicula alfreddugesi),Vaejovis属,番茄斜背瘤瘿螨(Vasates lycopersici);
来自唇足纲(Chilopoda)的害虫,例如地蜈蚣属(Geophilus spp.)、蚰蜒属(Scutigera spp.);
来自弹尾目或弹尾纲(Collembola)的害虫,例如武装棘跳虫(Onychiurusarmatus)、绿圆跳虫(Sminthurus viridis);
来自倍足纲(Diplopoda)的害虫,例如千足虫(Blaniulus guttulatus);
来自昆虫纲(Insecta),例如蜚蠊目(Blattodea)的害虫,例如东方蜚蠊(Blattaorientalis),亚洲蜚蠊(Blattella asahinai),德国蜚蠊(Blattella germanica),马德拉蜚蠊(Leucophaea maderae),Loboptera decipiens,家屋蟑螂(Neostylopygarhombifolia),古巴蠊属(Panchlora spp.),木蠊属(Parcoblatta spp.),大蠊属(Periplaneta spp.),例如美洲大蠊(Periplaneta americana)、澳洲大蠊(Periplanetaaustralasiae),苏里南潜蠊(Pycnoscelus surinamensis),棕带蜚蠊(Supellalongipalpa);
来自鞘翅目(Coleoptera)的害虫,例如条纹南瓜甲(Acalymma vittatum),菜豆象(Acanthoscelides obtectus),喙丽金龟属(Adoretus spp.),小蜂窝甲虫(Aethinatumida),杨毛臀萤叶甲(Agelastica alni),窄吉丁属(Agrilus spp.),例如白蜡窄吉丁(Agrilus planipennis)、Agrilus coxalis、栗双线吉丁(Agrilus bilineatus)、桦铜吉丁(Agrilus anxius)、叩甲属(Agriotes spp.),例如直条叩头虫(Agriotes linneatus)、小麦金针虫(Agriotes mancus),黑菌虫(Alphitobius diaperinus),马铃薯鳃角金龟(Amphimallon solstitialis),家具窃蠹(Anobium punctatum),星天牛属(Anoplophoraspp.),例如光肩星天牛(Anoplophora glabripennis)、花象属(Anthonomus spp.),例如棉铃象甲(Anthonomus grundis),圆皮蠹属(Anthrenus spp.),长喙小象属(Apion spp.),阿鳃金龟属(Apogonia spp.),隐食甲属(Atomaria spp.),例如甜菜隐食甲(Atomarialinearis),毛皮蠹属(Attagenus spp.),灰暗船象(Baris caerulescens),恶条豆象(Bruchidius obtectus),豆象属(Bruchus spp.),例如豌豆象(Bruchus pisorum)、蚕豆象(Bruchus rufimanus),龟金花虫属(Cassida spp.),菜豆莹叶甲(Cerotoma trifurcata),龟象属(Ceuthorhynchus spp.),例如白菜籽龟象(Ceutorrhynchus assimilis)、甘蓝茎龟象(Ceutorrhynchus quadridens)、芜菁象甲(Ceutorrhynchus rapae),凹胫跳甲属(Chaetocnema spp.),例如甘薯跳甲(Chaetocnema confinis)、美国齿跳甲(Chaetocnemadenticulata)、荒地玉米跳甲(Chaetocnema ectypa)、Cleonus mendicus,宽胸叩头虫属(Conoderus spp.),根颈象属(Cosmopolites spp.),例如香蕉象甲(Cosmopolitessordidus),褐新西兰肋翅鳃角金龟(Costelytra zealundica),叩甲属(Ctenicera spp.),象虫属(Curculio spp.),例如核桃象甲(Curculio caryae)、大栗象(Curculiocaryatrypes)、美洲榛子象(Curculio obtusus)、小栗象(Curculio sayi),锈赤扁谷盗(Cryptolestes ferrugineus),长角扁谷盗(Cryptolestes pusillus),杨干隐喙象(Cryptorhynchus lapathi),芒果果核象甲(Cryptorhynchus mangiferae),细枝象属(Cylindrocopturus spp.),密点细枝象(Cylindrocopturus adspersus),洋松细枝象(Cylindrocopturus furnissi),大小蠹属(Dendroctonus spp.),例如山松大小蠹(Dendroctonus ponderosae),皮蠹属(Dermestes spp.),叶甲属(Diabrotica spp.),例如黄瓜条叶甲(Diabrotica balteata)、北方玉米根虫(Diabrotica barberi)、十一星叶甲食根亚种(Diabrotica undecimpunctata howardi)、Diabrotica undecimpunctataundecimpunctata、玉米根萤叶甲(Diabrotica virgifera virgifera)、玉米根虫(Diabrotica virgifera zeae),蛀野螟属(Dichocrocis spp.),水稻铁甲(Dicladispaarmigera),Diloboderus属,芽象属(Epicaerus spp.),食植瓢虫属(Epilachna spp.),例如南瓜瓢虫(Epilachna borealis)、墨西哥豆瓢虫(Epilachna varivestis),毛跳甲属(Epitrix spp.),例如黄瓜跳甲(Epitrix cucumeris)、茄子叶甲(Epitrix fuscula)、烟草跳甲(Epitrix hirtipennis)、美国马铃薯跳甲(Epitrix subcrinita)、块茎跳甲(Epitrixtuberis),钻孔虫属(Faustinus spp.),裸蛛甲(Gibbium psylloides),阔角谷盗(Gnathocerus cornutus),菜心螟(Hellula undalis),黑异爪蔗金龟(Heteronychusarator),寡节鳃金龟属(Heteronyx spp.),Hylamorpha elegans,北美家天牛(Hylotrupesbajulus),紫苜蓿叶象(Hypera postica),蓝绿象(Hypomeces squamosus),咪小蠹属(Hypothenemus spp.),例如咖啡果小蠹(Hypothenemus hampei)、苹枝小囊(Hypothenemusobscurus)、毛竹小蠹(Hypothenemus pubescens),甘蔗大褐齿爪鳃金龟(Lachnosternaconsanguinea),烟草甲(Lasioderma serricorne),长头谷盗(Latheticus oryzae),波缘薪甲属(Lathridius spp.),合瓜负泥虫属(Lema spp.),科罗拉多马铃薯甲虫(Leptinotarsa decemlineata),银潜蛾属(Leucoptera spp.),例如咖啡潜叶蛾(Leucoptera coffeella),Limonius ectypus,稻根象(Lissorhoptrus oryzophilus),卜象属(Listronotus(=Hyperodes)spp.),筒喙象属(Lixus spp.),Luperodes属,黄胸寡毛跳甲(Luperomorpha xanthodera),粉蠹属(Lyctus spp.),缢虎天牛属(Megacyllenespp.),例如刺槐缢虎天牛(Megacyllene robiniae),美洲叶甲属(Megascelis spp.),梳爪叩头虫属(Melanotus spp.),例如Melanotus longulus oregonensis,油菜露尾甲(Meligethes aeneus),鳃金龟属(Melolontha spp.),例如大栗鳃角金龟(Melolonthamelolontha),Migdolus属,墨天牛属(Monochamus spp.),象甲(Naupactusxanthographus),隐跗郭公虫属(Necrobia spp.),Neogalerucella属,黄蛛甲(Niptushololeucus),椰蛀犀金龟(Oryctes rhinoceros),锯谷盗(Oryzaephilus surinamensis),Oryzaphagus oryzae,耳象属(Otiorrhynchus spp.),例如苹果耳喙象(Otiorhynchuscribricollis)、大苜蓿耳象(Otiorhynchus ligustici)、大苜蓿耳喙象(Otiorhynchusovatus)、粗糙草莓耳喙象(Otiorhynchus rugosostriarus)、黑葡萄耳象(Otiorhynchussulcatus),泥虫属(Oulema spp.),例如黑角负泥虫(Oulema melanopus)、水稻负泥虫(Oulema oryzae),小青花金龟(Oxycetonia jucunda),辣根猿叶甲(Phaedoncochleariae),食叶鳃金龟属(Phyllophaga spp.),鳃金龟(Phyllophaga helleri),菜跳甲属(Phyllotreta spp.),例如辣根条跳甲(Phyllotreta armoraciae)、西方黑跳甲(Phyllotreta pusilla)、美条纹跳甲(Phyllotreta ramosa)、黄曲条跳甲(Phyllotretastriolata),日本弧丽金龟(Popillia japonica),安第斯马铃薯象属(Premnotrypesspp.),大谷蠹(Prostephanus truncatus),蚤跳甲属(Psylliodes spp.),例如马铃薯跳甲(Psylliodes affinis)、油菜金头跳甲(Psylliodes chrysocephala)、忽布跳甲(Psylliodes punctulata),蛛甲属(Ptinus spp.),暗色瓢虫(Rhizobius ventralis),谷蠹(Rhizopertha dominica),隐颏象属(Rhynchophorus spp.),红棕象甲(Rhynchophorusferrugineus),棕榈象甲(Rhynchophorus palmarum),小蠹属(Scolytus spp.),例如欧洲榆小蠹(Scolytus multistriatus),侧突双棘长蠹(Sinoxylon perforans),谷象属(Sitophilus spp.),例如麦子象鼻虫(Sitophilus granarius)、罗望子象(Sitophiluslinearis)、米象(Sitophilus oryzae)、玉米象(Sitophilus zeamais),尖隐喙象属(Sphenophorus spp.),药材甲(Stegobium paniceum),茎干象属(Sternechus spp.),例如豆茎象(Sternechus paludatus),宽幅天牛属(Symphyletes spp.),纤毛象属(Tanymecusspp.),例如玉米象鼻虫(Tanymecus dilaticollis)、印度纤毛象(Tanymecus indicus)、红豆草灰象甲(Tanymecus palliatus),黄粉虫(Tenebrio molitor),大谷盗(Tenebrioidesmauretanicus),拟谷盗属(Tribolium spp.),例如美洲黑拟谷盗(Tribolium audax)、赤拟谷盗(Tribolium castaneum)、杂拟谷盗(Tribolium confusum),斑皮蠹属(Trogodermaspp.),籽象属(Tychius spp.),脊虎天牛属(Xylotrechus spp.),距步甲属(Zabrusspp.),例如玉米距步甲(Zabrus tenebrioides);
来自革翅目(Dermaptera)的害虫,例如海岸肥螋(Anisolabis maritime)、欧洲球嫂(Forficula auricularia)、红蠼螋(Labidura riparia);
来自双翅目(Diptera)的害虫,例如伊蚊属(Aedes spp.),例如埃及伊蚊(Aedesaegypti)、白纹伊蚊(Aedes albopictus)、叮刺伊蚊(Aedes sticticus)、刺扰伊蚊(Aedesvexans),潜蝇属(Agromyza spp.),例如苜蓿斑潜蝇(Agromyza frontella)、美洲黍潜蝇(Agromyza parvicornis),按实蝇属(Anastrepha spp.),按蚊属(Anopheles spp.),例如四斑按蚊(Anopheles quadrimaculatus)、冈比亚按蚊(Anopheles gambiae),瘿蚊属(Asphondylia spp.),果实蝇属(Bactrocera spp.),例如瓜实蝇(Bactroceracucurbitae)、桔小实蝇(Bactrocera dorsalis)、油橄榄果实蝇(Bactrocera oleae),花园毛蚊(Bibio hortulanus),红头丽蝇(Calliphora erythrocephala),红头丽蝇(Calliphora vicina),地中海实蝇(Ceratitis capitata),摇蚊属(Chironomus spp.),金蝇属(Chrysomyia spp.),斑虻属(Chrysops spp.),高额麻虻(Chrysozona pluvialis),锥蝇属(Cochliomyia spp.),康瘿蚊属(Contarinia spp.),例如葡萄瘿蚊(Contariniajohnsoni)、甘蓝瘿蚊(Contarinia nasturtii)、梨叶瘿蚊(Contarinia pyrivora)、向日葵瘿蚊(Contarinia schulzi)、高粱瘿蚊(Contarinia sorghicola)、麦黄吸浆虫(Contarinia tritici),人皮蝇(Cordylobia anthropophaga),环足摇蚊(Cricotopussylvestris),库蚊属(Culex spp.),例如尖音库蚊(Culex pipiens)、致倦库蚊(Culexquinquefasciatus),库蠓属(Culicoides spp.),脉毛蚊属(Culiseta spp.),黄蝇属(Cuterebra spp.),橄榄实蝇(Dacus oleae),叶瘿蚊属(Dasineura spp.),例如油菜荚叶瘿蚊(Dasineura brassicae),地种蝇属(Delia spp.),例如葱地种蝇(Delia antiqua)、麦地种蝇(Delia coarctata)、毛跗地种蝇(Delia florilega)、灰地种蝇(Delia platura)、甘蓝地种蝇(Delia radicum),人肤蝇(Dermatobia hominis),果蝇属(Drosophila spp.),例如黄猩猩果蝇(Drosphila melanogaster)、樱桃果蝇(Drosophila suzukii),稻象属(Echinocnemus spp.),芹菜拟迈实蝇(Euleia heraclei),厕蝇属(Fannia spp.),胃蝇属(Gasterophilus spp.),舌蝇属(Glossina spp.),麻虻属(Haematopota spp.),毛眼水蝇属(Hydrellia spp.),大麦水蝇(Hydrellia griseola),种蝇属(Hylemya spp.),虱蝇属(Hippobosca spp.),皮蝇属(Hypoderma spp.),斑潜蝇属(Liriomyza spp.),例如菜斑潜蝇(Liriomyza brassicae)、南美斑潜蝇(Liriomyza huidobrensis)、美洲斑潜蝇(Liriomyza sativae),绿蝇属(Lucilia spp.),例如铜绿蝇(Lucilia cuprina),罗蛉属(Lutzomyia spp.),曼蚊属(Mansonia spp.),家蝇属(Musca spp.),例如家蝇(Muscadomestica)、舍蝇(Musca domestica vicina),狂蝇属(Oestrus spp.),瑞典麦杆蝇(Oscinella frit),Paratanytarsus属,Paralauterborniella subcincta,泉蝇属(Pegomya或Pegomyia spp.),例如甜菜蝇(Pegomya betae)、甜菜潜叶蝇(Pegomyahyoscyami)、悬钩子泉蝇(Pegomya rubivora),白蛉属(Phlebotomus spp.),草种蝇属(Phorbia spp.),伏蝇属(Phormia spp.),酪蝇(Piophila casei),芦笋实蝇(Platypareapoeciloptera),Prodiplosis属,胡萝卜茎蝇(Psila rosae),绕实蝇属(Rhagoletisspp.),例如樱桃实蝇(Rhagoletis cingulata)、核桃绕实蝇(Rhagoletis completa)、黑樱桃实蝇(Rhagoletis fausta)、欧洲甜樱桃绕实蝇(Rhagoletis indifferens)、越橘绕实蝇(Rhagoletis mendax)、苹果实蝇(Rhagoletis pomonella),麻蝇属(Sarcophaga spp.),蚋属(Simulium spp.),例如南方蚋(Simulium meridionale),螫蝇属(Stomoxys spp.),虻属(Tabanus spp.),根斑蝇属(Tetanops spp.),大蚊属(Tipula spp.),例如欧洲大蚊(Tipula paludosa)、牧场大蚊(Tipula simplex),木瓜驮实蝇(Toxotrypanacurvicauda);
来自半翅目(Hemiptera)的害虫,例如Acizzia acaciaebaileyanae、Acizziadodonaeae、木虱(Acizzia uncatoides),头尖蝗(Acrida turrita),无网长管蚜属(Acyrthosipon spp.),例如豌豆长管蚜(Acyrthosiphon pisum),Acrogonia属,Aeneolamia属,隆脉木虱属(Agonoscena spp.),粉虱属(Aleurocanthus spp.),欧洲甘蓝粉虱(Aleyrodes proletella),甘蔗穴粉虱(Aleurolobus barodensis),软毛粉虱(Aleurothrixus floccosus),植莲木风(Allocaridara malayensis),芒果叶蝉属(Amrasca spp.),例如小绿叶蝉(Amrasca bigutulla)、叶蝉(Amrasca devastans),飞廉短尾蚜(Anuraphis cardui),肾圆盾介壳虫属(Aonidiella spp.),例如红肾圆盾蚧(Aonidiella aurantii)、黄圆蹄盾蚧(Aonidiella citrina)、赤圆介壳虫(Aonidiellainornata),梨瘤蚜(Aphanostigma piri),蚜属(Aphis spp.),例如苹果黄蚜(Aphiscitricola)、豆蚜(Aphis craccivora)、甜菜蚜(Aphis fabae)、草莓根蚜(Aphisforbesi)、大豆蚜(Aphis glycines)、棉蚜(Aphis gossypii)、常春藤蚜(Aphis hederae)、葡萄藤蚜(Aphis illinoisensis)、中仲蚜(Aphis middletoni)、鼠李马铃薯蚜(Aphisnasturtii)、夹竹桃蚜(Aphis nerii)、苹果蚜(Aphis pomi)、绣线菊蚜(Aphisspiraecola)、喜荚蒾蚜(Aphis viburniphila),葡萄叶蜂(Arboridia apicalis),Arytainilla属,小圆盾蚧属(Aspidiella spp.),圆盾介壳虫属(Aspidiotus spp.),例如常春藤圆盾蚧(Aspidiotus nerii),Atanus属,茄沟无网蚜(Aulacorthum solani),烟粉虱(Bemisia tabaci),澳大利亚木虱(Blastopsylla occidentalis),Boreioglycaspismelaleucae,李短尾蚜(Brachycaudus helichrysi),微管蚜属(Brachycolus spp.),甘蓝蚜(Brevicoryne brassicae),喀木虱属(Cacopsylla spp.),例如梨木虱(Cacopsyllapyricola),小褐稻虱(Calligypona marginata),Capulinia属,黄头大叶蝉(Carneocephala fulgida),甘蔗绵蚜(Ceratovacuna lanigera),沫蝉科(Cercopidae),蜡蚧属(Ceroplastes spp.),草莓钉蚜(Chaetosiphon fragaefolii),蔗黄雪盾阶(Chionaspis tegalensis),荼绿叶蜂(Chlorita onukii),台湾大蝗(Chondracrisrosea),核桃黑斑蚜(Chromaphis juglandicola),褐圆蚧(Chrysomphalus aonidum)、黑褐圆盾蚧(Chrysomphalus ficus),玉米叶蝉(Cicadulina mbila),Coccomytilus halli,软蚧属(Coccus spp.),例如褐软蜡蚧(Coccus hesperidum)、长椭圆软蚧(Coccuslongulus)、橘软蜡蚧(Coccus pseudomagnoliarum)、咖啡绿软蚧(Coccus viridis),隐瘤蚜(Cryptomyzus ribis),Cryptoneossa属,梳木风属(Ctenarytaina spp.),黄翅叶蝶属(Dalbulus spp.),杜鹃粉虱(Dialeurodes chittendeni),柑橘粉虱(Dialeurodescitri),柑橘木虱(Diaphorina citri),白背盾蚧属(Diaspis spp.),双尾蚜属(Diuraphisspp.),Doralis属,草履介壳虫属(Drosicha spp.),西圆尾蚜属(Dysaphis spp.),例如锈条蚜(Dysaphis apiifolia)、车前圆尾蚜(Dysaphis plantaginea)、百合西圆尾蚜(Dysaphis tulipae),灰粉蚧属(Dysmicoccus spp.),小绿叶蝉属(Empoasca spp.),例如西部马铃薯叶蝉(Empoasca abrupta)、马铃薯小绿叶蝉(Empoasca fabae)、苹果小绿叶蝉(Empoasca maligna)、茄微叶蝉(Empoasca solana)、Empoasca stevensi,绵蚜属(Eriosoma spp.),例如美洲绵蚜(Eriosoma americanum)、苹果绵蚜(Eriosomalanigerum)、梨根绵蚜(Eriosoma pyricola),斑叶蝉属(Erythroneura spp.),Eucalyptolyma属,褐木虱属(Euphyllura spp.),殃叶蝉(Euscelis bilobatus),弗氏粉蚧属(Ferrisia spp.),围盾介壳虫属(Fiorinia spp.),Furcaspis oceanica,咖啡地粉阶(Geococcus coffeae),蓝盾木虱属(Glycaspis spp.),银合欢木虱(Heteropsyllacubana),颊木虱(Heteropsylla spinulosa),琉璃叶蝉(Homalodisca coagulata),桃大尾蚜(Hyalopterus arundinis),桃粉蚜(Hyalopterus pruni),吹绵蚧属(Icerya spp.),例如吹绵蚧(Icerya purchasi),片角叶蝉属(Idiocerus spp.),扁喙叶蝉属(Idioscopusspp.),灰飞虱(Laodelphax striatellus),蜡蚧属(Lecanium spp.),例如水土坚蚧(Lecanium corni)(=扁平球坚蚧(Parthenolecanium corni)),牡蛎蚧属(Lepidosaphesspp.),例如榆蛎盾蚧(Lepidosaphes ulmi),萝卜蚜(Lipaphis erysimi),日本长白盾蚧(Lopholeucaspis japonica),斑衣蜡蝉(Lycorma delicatula),长管蚜属(Macrosiphumspp.),例如马铃薯长管蚜(Macrosiphum euphorbiae)、百合长管蚜(Macrosiphum lilii)、蔷薇长管蚜(Macrosiphum rosae),紫菀点叶蝉(Macrosteles facifrons),沫蝶属(Mahanarva spp.),高粱蚜(Melanaphis sacchari),Metcalfiella属,Metcalfapruinosa,麦无网长管蚜(Metopolophium dirhodum),黑缘平翅斑蚜(Monelliacostalis),Monelliopsis pecanis,瘤蚜属(Myzus spp.),例如冬葱瘤额蚜(Myzusascalonicus)、李瘤蚜(Myzus cerasi)、女贞瘤蚜(Myzus ligustri)、堇菜瘤蚜(Myzusornatus)、桃蚜(Myzus persicae)、烟蚜(Myzus nicotianae),莴苣蚜(Nasonoviaribisnigri),新马粉虱属(Neomaskellia spp.),黑尾叶蝉属(Nephotettix spp.),例如黑尾叶蝉(Nephotettix cincticeps)、二条斑黑尾叶蝉(Nephotettix nigropictus),Nettigoniclla spectra,褐飞虱(Nilaparvata lugens),Oncometopia属,Ortheziapraelonga,中华稻蝗(Oxya chinensis),芽瘿木虱属(Pachypsylla spp.),杨梅粉虱(Parabemisia myricae),虱啮属(Paratrioza spp.),例如马铃薯木虱(Paratriozacockerelli),片盾蚧属(Parlatoria spp.),瘿绵蚜属(Pemphigus spp.),例如囊柄瘿绵蚜(Pemphigus bursarius)、杨脉瘿棉蚜(Pemphigus populivenae),玉米蜡蝉(Peregrinusmaidis),扁角飞虱属(Perkinsiella spp.),绵粉蚧属(Phenacoccus spp.),例如苏铁褐点并盾蚧(Phenacoccus madeirensis),杨平翅绵蚜(Phloeomyzus passerinii),忽布疣蚜(Phorodon humuli),葡萄根瘤蚜属(Phylloxera spp.),例如破倭蚜(Phylloxeradevastatrix)、警根瘤蚜(Phylloxera notabilis),苏铁褐点并盾蚧(Pinnaspisaspidistrae),臀纹粉蚧属(Planococcus spp.),例如桔粉介壳虫(Planococcus citri),Prosopidopsylla flava,梨形原绵腊蚧(Protopulvinaria pyriformis),桑白蚧(Pseudaulacaspis pentagona),粉蚧属(Pseudococcus spp.),例如嗜桔粉蚧(Pseudococcus calceolariae)、康氏粉蚧(Pseudococcus comstocki)、长尾粉蚧(Pseudococcus longispinus)、葡萄粉蚧(Pseudococcus maritimus)、暗色粉蚧(Pseudococcus viburni),杰木虱属(Psyllopsis spp.),木虱属(Psylla spp.),例如黄杨木虱(Psylla buxi)、苹木虱(Psylla mali)、梨木虱(Psylla pyri),金小蜂属(Pteromalusspp.),绵蚧属(Pulvinaria spp.),Pyrilla属,笠圆盾蚧属(Quadraspidiotus spp.),例如胡桃圆盾蚧(Quadraspidiotus juglansregiae)、杨笠圆盾蚧(Quadraspidiotusostreaeformis)、梨圆盾蚧(Quadraspidiotus perniciosus),Quesada gigas,平刺粉蚧属(Rastrococcus spp.),缢管蚜属(Rhopalosiphum spp.),例如玉米蚜(Rhopalosiphummaidis)、苹草缢管蚜(Rhopalosiphum oxyacanthae)、禾谷缢管蚜(Rhopalosiphum padi)、红腹缢管蚜(Rhopalosiphum rufiabdominale),黑盔蚧属(Saissetia spp.),例如咖啡黑盔蚧(Saissetia coffeae)、Saissetia miranda、Saissetia neglecta、橄榄黑盔蚧(Saissetia oleae),葡萄带叶蝉(Scaphoideus titanus),麦二叉蚜(Schizaphisgraminum),刺盾蚧(Selenaspidus articulatus),黄伪毛蚜(Sipha flava),麦长管蚜(Sitobion avenae),长唇基飞虱属(Sogata spp.),白背飞虱(Sogatella furcifera),稻飞风属(Sogatodes spp.),Stictocephala festina,树粉虱(Siphoninus phillyreae),Tenalaphara malayensis,Tetragonocephela属,美洲山核桃长斑蚜(Tinocalliscaryaefoliae),广胸沫蝉属(Tomaspis spp.),桔蚜属(Toxoptera spp.),例如桔二叉蚜(Toxoptera aurantii)、桔蚜(Toxoptera citricidus),温室粉虱(Trialeurodesvaporariorum),尖翅木虱属(Trioza spp.),例如柿木虱(Trioza diospyri),小叶蝉属(Typhlocyba spp.),矢盾介壳虫属(Unaspis spp.),葡萄根瘤蚜(Viteus vitifolii),么叶蝉属(Zygina spp.);
来自异翅亚目(Heteroptera)的害虫,例如麦蝽属(Aelia spp.),南瓜缘蝽(Anasatristis),拟丽蝽属(Antestiopsis spp.),Boisea属,土长蝽属(Blissus spp.),俊盲蝽属(Calocoris spp.),斑腿微剌盲蝽(Campylomma livida),异背长蝽属(Cavelerius spp.),臭虫属(Cimex spp.),例如Cimex adjunctus、热带臭虫(Cimex hemipterus)、温带臭虫(Cimex lectularius)、蝠臭虫(Cimex pilosellus),白辧麦寄蝇属(Collaria spp.),绿盲蝽(Creontiades dilutus),胡椒缘蝽(Dasynus piperis),Dichelops furcatus,厚氏长棒网蝽(Diconocoris hewetti),棉红蝽属(Dysdercus spp.),美洲蝽属(Euschistus spp.),例如褐蝽(Euschistus heros)、褐臭蝽(Euschistus servus)、三点美洲蝽(Euschistustristigmus)、三点美洲蝽(Euschistus variolarius),菜蝽属(Eurydema spp.),扁盾蝽属(Eurygaster spp.),茶翅蝽(Halyomorpha halys),盲蝽属(Heliopeltis spp.),Horciasnobilellus,稻缘蝽属(Leptocorisa spp.),异稻缘蝽(Leptocorisa varicornis),西部喙缘蝽(Leptoglossus occidentalis)、叶喙缘蝽(Leptoglossus phyllopus),丽盲蝽属(Lygocoris spp.),例如原丽盲蝽(Lygocoris pabulinus),草盲蝽属(Lygus spp.),例如灰豆草盲蝽(Lygus elisus)、豆荚盲蝽(Lygus hesperus)、美洲牧草盲蝽(Lyguslineolaris),蔗黑长蝽(Macropes excavatus),筛豆龟蝽(Megacopta cribraria),盲蝽科(Miridae),金光绿盲蝽(Monalonion atratum),绿蝽属(Nezara spp.),例如稻绿蝽(Nezara viridula),小长蝽属(Nysius spp.),稻蝽属(Oebalus spp.),Pentomidae,方背皮蝽(Piesma quadrata),壁蝽属(Piezodorus spp.),例如盖德拟壁蝽(Piezodorusguildinii),杂盲蝽属(Psallus spp.),Pseudacysta persea,红猎蝽属(Rhodnius spp.),可可褐盲蝽(Sahlbergella singularis),Scaptocoris castanea,黑蝽属(Scotinophoraspp.),梨冠网蝽(Stephanitis nashi),Tibraca属,锥猎蝽属(Triatoma spp.);
来自膜翅目(Hymenoptera)的害虫,例如顶切叶蚁属(Acromyrmex spp.),菜叶蜂属(Athalia spp.),例如黄翅菜叶蜂(Athalia rosae),切叶蚁属(Atta spp.),弓背蚁属(Camponotus spp.),长黄胡蜂属(Dolichovespula spp.),松叶蜂属(Diprion spp.),例如类欧松叶蜂(Diprion similis),实叶蜂属(Hoplocampa spp.),例如樱实叶蜂(Hoplocampacookei)、苹叶蜂(Hoplocampa testudinea),毛蚁属(Lasius spp.),阿根廷蚁(Linepithema(Iridiomyrmex)humile),小家蚁(Monomorium pharaonis),立毛蚁属(Paratrechina spp.),Paravespula属,斜结蚁属(Plagiolepis spp.),树蜂属(Sirexspp.),例如云杉树蜂(Sirex noctilis),红火蚁(Solenopsis invicta),Tapinoma属,白足狡臭蚁(Technomyrmex albipes),树蜂属(Urocerus spp.),胡蜂属(Vespa spp.),例如黄边胡蜂(Vespa crabro),小火蚁(Wasmannia auropunctata),黑树蜂属(Xeris spp.);
来自等足目(Isopoda)的害虫,例如鼠妇(Armadillidium vulgare)、栉水虱(Oniscus asellus)、球鼠妇(Porcellio scaber);
来自等翅目(Isoptera)的害虫,例如乳白蚁属(Coptotermes spp.),例如台湾乳白蚁(Coptotermes formosanus),堆角白蚁(Cornitermes cumulans),堆砂白蚁属(Cryptotermes spp.),楹白蚁属(Incisitermes spp.),木白蚁属(Kalotermes spp.),稻麦小白蚁(Microtermes obesi),象白蚁属(Nasutitermes spp.),土白蚁属(Odontotermesspp.),洞白蚁属(Porotermes spp.),散白蚁属(Reticulitermes spp.),例如北美散白蚁(Reticulitermes flavipes)、西方散白蚁(Reticulitermes hesperus);
来自鳞翅目(Lepidoptera)的害虫,例如小蜡螟(Achroia grisella),桑剑纹夜蛾(Acronicta major),褐带卷蛾属(Adoxophyes spp.),例如棉褐带卷蛾(Adoxophyesorana),烦夜蛾(Aedia leucomelas),地老虎属(Agrotis spp.),例如黄地老虎(Agrotissegetum)、小地老虎(Agrotis ipsilon),波纹夜蛾属(Alabama spp.),例如棉叶波纹夜蛾(Alabama argillacea),脐橙螟(Amyelois transitella),条麦蛾属(Anarsia spp.),干煞夜蛾属(Anticarsia spp.),例如大豆夜蛾(Anticarsia gemmatalis),条小卷蛾属(Argyroploce spp.),丫纹夜蛾属(Autographa spp.),甘蓝夜蛾(Barathra brassicae),苹髓尖蛾(Blastodacna atra),禾弄蝶(Borbo cinnara),棉潜蛾(Bucculatrixthurberiella),松尺蠖(Bupalus piniarius),蛀褐夜蛾属(Busseola spp.),Cacoecia属,茶细蛾(Caloptilia theivora),烟卷蛾(Capua reticulana),苹果蠹蛾(Carpocapsapomonella),桃蛀果蛾(Carposina niponensis),冬尺蛾(Cheimatobia brumata),禾草螟属(Chilo spp.),例如Chilo plejadellus、二化螟(Chilo suppressalis),苹果舞蛾(Choreutis pariana),色卷蛾属(Choristoneura spp.),锞纹夜蛾(Chrysodeixischalcites),葡萄果蠹蛾(Clysia ambiguella),卷螟属(Cnaphalocerus spp.),稻纵卷叶螟(Cnaphalocrocis medinalis),云卷蛾属(Cnephasia spp.),Conopomorpha属,球颈象属(Conotrachelus spp.),Copitarsia属,小卷蛾属(Cydia spp.),例如豌豆小卷蛾(Cydianigricana)、苹果蠹蛾(Cydia pomonella),Dalaca noctuides,绢野螟属(Diaphaniaspp.),Diparopsis属,小蔗螟(Diatraea saccharalis),梢斑螟属(Dioryctria spp.),例如Dioryctria zimmermani,钻夜蛾属(Earias spp.),Ecdytolopha aurantium,南美玉米苗斑螟(Elasmopalpus lignosellus),非洲蔗螟(Eldana saccharina),粉斑螟属(Ephestia spp.),例如烟草粉斑螟(Ephestia elutella)、地中海粉螟(Ephestiakuehniella),叶小卷蛾属(Epinotia spp.),苹淡褐卷蛾(Epiphyas postvittana),松尺蛾属(Erannis spp.),亚洲胡桃蛾(Erschoviella musculana),荚斑螟属(Etiella spp.),艳叶夜蛾属(Eudocima spp.),棕卷蛾属(Eulia spp.),女贞细卷蛾(Eupoeciliaambiguella),黄毒蛾属(Euproctis spp.),例如黄毒蛾(Euproctis chrysorrhoea),切夜蛾属(Euxoa spp.),脏切叶蛾属(Feltia spp.),大蜡螟(Galleria mellonella),细蛾属(Gracillaria spp.),小食心虫属(Grapholitha spp.),例如梨小食心虫(Grapholitamolesta)、杏小食心虫(Grapholita prunivora),蚀叶野螟属(Hedylepta spp.),铃夜蛾属(Helicoverpa spp.),例如棉铃虫(Helicoverpa armigera)、美洲棉铃虫(Helicoverpazea),实夜蛾属(Heliothis spp.),例如烟芽夜蛾(Heliothis virescens),褐织蛾(Hofmannophila pseudospretella),同斑螟属(Homoeosoma spp.),长卷蛾属(Homonaspp.),苹果巢蛾(Hyponomeuta padella),柿蒂虫(Kakivoria flavofasciata),亮灰蝶属(Lampides spp.),贪夜蛾属(Laphygma spp.),蠹食心虫(Laspeyresia molesta),茄黄斑螟(Leucinodes orbonalis),潜叶蛾属(Leucoptera spp.),例如咖啡潜叶蛾(Leucopteracoffeella),潜叶细蛾属(Lithocolletis spp.),例如苹细蛾(Lithocolletisblancardella),绿果冬夜蛾(Lithophane antennata),花翅小卷蛾属(Lobesia spp.),例如葡萄花翅小卷蛾(Lobesia botrana),豆白隆切根虫(Loxagrotis albicosta),毒蛾属(Lymantria spp.),例如舞毒蛾(Lymantria dispar),潜蛾属(Lyonetia spp.),例如桃潜蛾(Lyonetia clerkella),黄褐天幕毛虫(Malacosoma neustria),豆野螟(Marucatestulalis),甘蓝夜蛾(Mamestra brassicae),暮眼蝶(Melanitis leda),毛胫夜蛾属(Mocis spp.),Monopis obviella,粘虫(Mythimna separata),橡长角蛾(Nemapogoncloacellus),水螟属(Nymphula spp.),Oiketicus属,楸属(Omphisa spp.),秋尺蛾属(Operophtera spp.),麦秆夜蛾属(Oria spp.),瘤丛螟属(Orthaga spp.),秆野螟属(Ostrinia spp.),例如欧洲玉米螟(Ostrinia nubilalis),小眼夜蛾(Panolis flammea),稻弄蝶属(Parnara spp.),红铃麦蛾属(Pectinophora spp.),例如棉红铃虫(Pectinophora gossypiella),潜跳甲属(Perileucoptera spp.),块茎蛾属(Phthorimaeaspp.),例如马铃薯块茎蛾(Phthorimaea operculella),柑桔潜叶蛾(Phyllocnistiscitrella),小潜细蛾属(Phyllonorycter spp.),例如斑幕潜叶蛾(Phyllonorycterblancardella)、山楂潜叶蛾(Phyllonorycter crataegella),菜粉蝶属(Pieris spp.),例如菜粉蝶(Pieris rapae),荷兰石竹小卷蛾(Platynota stultana),印度谷螟(Plodiainterpunctella),金翅夜蛾属(Plusia spp.),小菜蛾(Plutella xylostella)(=小菜蛾(Plutella maculipennis)),Podesia spp.,例如Podesia syringae,小白巢蛾属(Praysspp.),斜纹夜蛾属(Prodenia spp.),烟草天蛾属(Protoparce spp.),黏虫属(Pseudaletia spp.),例如一星黏虫(Pseudaletia unipuncta),大豆尺夜蛾(Pseudoplusia includens),玉米螟(Pyrausta nubilalis),薄荷灰夜蛾(Rachiplusianu),禾螟属(Schoenobius spp.),例如Schoenobius bipunctifer,白禾螟属(Scirpophagaspp.),例如稻白螟(Scirpophaga innotata),黄地老虎(Scotia segetum),蛀茎夜蛾属(Sesamia spp.),例如大螟(Sesamia inferens),长须卷蛾属(Sparganothis spp.),灰翅夜蛾属(Spodoptera spp.),例如Spodoptera eradiana,甜菜夜蛾(Spodoptera exigua),草地贪夜蛾(Spodoptera frugiperda),Spodoptera praefica,展足蛾属(Stathmopodaspp.),Stenoma属,花生卷叶麦蛾(Stomopteryx subsecivella),透翅蛾属(Synanthedonspp.),安第斯马铃薯块茎蛾(Tecia solanivora),异舟蛾属(Thaumetopoea spp.),大豆夜蛾(Thermesia gemmatalis),木塞谷蛾(Tinea cloacella),袋谷蛾(Tinea pellionella),幕谷蛾(Tineola bisselliella),卷蛾属(Tortrix spp.),毛毡衣蛾(Trichophagatapetzella),粉夜蛾属(Trichoplusia spp.),例如粉纹夜蛾(Trichoplusia ni),三化螟(Tryporyza incertulas),番茄斑潜蝇(Tuta absoluta),灰蝶属(Virachola spp.);
来自直翅目(Orthoptera)或跳跃目(Saltatoria)的害虫,例如家蟋蟀(Achetadomesticus),Dichroplus属,蝼蛄属(Gryllotalpa spp.),例如欧洲蝼蛄(Gryllotalpagryllotalpa),蔗蝗属(Hieroglyphus spp.),飞蝗属(Locusta spp.),例如东亚飞蝗(Locusta migratoria),黑蝗属(Melanoplus spp.),例如迁飞黑蝗(Melanoplusdevastator),Paratlanticus ussuriensis,沙漠蝗(Schistocerca gregaria);
来自虱目(Phthiraptera)的害虫,例如畜虱属(Damalinia spp.),血虱属(Haematopinus spp.),毛虱属(Linognathus spp.),虱属(Pediculus spp.),葡萄根瘤蚜(Phylloxera vastatrix),阴虱(Phthirus pubis),嚼虱属(Trichodectes spp.);
来自啮虫目(Psocoptera)的害虫,例如Lepinotus属,书虱属(Liposcelis spp.);
来自蚤目(Siphonaptera)的害虫,例如角叶蚤属(Ceratophyllus spp.),栉首蚤属(Ctenocephalides spp.),例如犬栉首蚤(Ctenocephalides canis)、猫栉头蚤(Ctenocephalides felis),致痒蚤(Pulex irritans),穿皮潜蚤(Tunga penetrans),印鼠客蚤(Xenopsylla cheopis);
来自缨翅目(Thysanoptera)的害虫,例如玉米黄呆蓟马(Anaphothripsobscurus),稻蓟马(Baliothrips biformis),Chaetanaphothrips leeuweni,鲜食葡萄镰蓟马(Drepanothrips reuteri),Enneothrips flavens,花蓟马属(Frankliniella spp.),例如烟褐花蓟马(Frankliniella fusca)、西花蓟马(Frankliniella occidentalis)、苏花蓟马(Frankliniella schultzei)、东方花蓟马(Frankliniella tritici)、越桔花蓟马(Frankliniella vaccinii)、威廉期花蓟马(Frankliniella williamsi),简管蓟马属(Haplothrips spp.),阳蓟马属(Heliothrips spp.),温室条蓟马(Hercinothripsfemoralis),卡蓟马属(Kakothrips spp.),葡萄蓟马(Rhipiphorothrips cruentatus),硬蓟马属(Scirtothrips spp.),小豆蘧带蓟马(Taeniothrips cardamomi),蓟马属(Thripsspp.),例如棕榈蓟马(Thrips palmi)、葱蓟马(Thrips tabaci);
来自衣鱼目(Zygentoma)(=缨尾目(Thysanura))的害虫,例如栉衣鱼属(Ctenolepisma spp.),衣鱼(Lepisma saccharina),盗火虫(Lepismodes inquilinus),小灶衣鱼(Thermobia domestica);
来自综合纲(Symphyla)的害虫,例如么蚰属(Scutigerella spp.),例如白松虫(Scutigerella immaculata);
来自软体动物门(Mollusca)、例如双壳纲(Bivalvia)的害虫,例如饰贝属(Dreissena spp.);
以及来自腹足纲(Gastropoda)的害虫,例如阿勇蛞蝓属(Arion spp.),例如黑蛞蝓(Arion ater rufus),双脐螺属(Biomphalaria spp.),泡螺属(Bulinus spp.),野蛞蝓属(Deroceras spp.),例如光滑野蛞蝓(Deroceras laeve),土蜗属(Galba spp.),椎实螺属(Lymnaea spp.),钉螺属(Oncomelania spp.),福寿螺属(Pomacea spp.),琥珀螺属(Succinea spp.);
来自线虫动物门(Nematoda)的植物害虫,即植物寄生性线虫类(plant-parasiticnematodes),特别是野外垫刃属(Aglenchus spp.),例如居农野外垫刃线虫(Aglenchusagricola),粒线虫属(Anguina spp.),例如小麦粒线虫(Anguina tritici),滑刃线虫属(Aphelenchoides spp.),例如花生滑刃线虫(Aphelenchoides arachidis)、草莓滑刃线虫(Aphelenchoides fragariae),刺线虫属(Belonolaimus spp.),例如细小刺线虫(Belonolaimus gracilis)、长尾刺线虫(Belonolaimus longicaudatus)、诺顿刺线虫(Belonolaimus nortoni),伞滑刃线虫属(Bursaphelenchus spp.),例如椰子红环腐线虫(Bursaphelenchus cocophilus)、荒漠伞滑刃线虫(Bursaphelenchus eremus)、松材线虫(Bursaphelenchus xylophilus),坏死线虫属(Cacopaurus spp.),例如瘟疫坏死线虫(Cacopaurus pestis),小环线虫属(Criconemella spp.),例如弯曲小环线虫(Criconemella curvata)、刻线小环线虫(Criconemella onoensis)、装饰小环线虫(Criconemella ornata)、畸形小环线虫(Criconemella rusium)、薄叶小环线虫(Criconemella xenoplax)(=异盘中环线虫(Mesocriconema xenoplax)),轮线虫属(Criconemoides spp.),例如Criconemoides ferniae、Criconemoides onoense、Criconemoides ornatum,茎线虫属(Ditylenchus spp.),例如鳞球茎茎线虫(Ditylenchusdipsaci),锥线虫属(Dolichodorus spp.),球异皮线虫属(Globodera spp.),例如马铃薯白线虫(Globodera pallida)、马铃薯金线虫(Globodera rostochiensis),螺旋线虫属(Helicotylenchus spp.),例如双宫螺旋线虫(Helicotylenchus dihystera),半轮线虫属(Hemicriconemoides spp.),鞘线虫属(Hemicycliophora spp.),异皮线虫属(Heteroderaspp.),例如燕麦胞囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii),潜根线虫属(Hirschmaniella spp.),纽带线虫属(Hoplolaimus spp.),长针线虫属(Longidorus spp.),例如非洲长针线虫(Longidorusafricanus),根结线虫属(Meloidogyne spp.),例如哥伦比亚根结线虫(Meloidogynechitwoodi)、伪根结线虫(Meloidogyne fallax)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyne incognita),瓢线虫属(Meloinema spp.),珍珠线虫属(Nacobbus spp.),拟茎线虫属(Neotylenchus spp.),拟长针线虫属(Paralongidorusspp.),拟滑刃线虫属(Paraphelenchus spp.),拟毛刺线虫属(Paratrichodorus spp.),例如较小拟毛刺线虫(Paratrichodorus minor),针线虫属(Paratylenchus spp.),短体线虫属(Pratylenchus spp.),例如穿刺短体线虫(Pratylenchus penetrans),Pseudohalenchus属,平滑垫刃属(Psilenchus spp.),斑皮胞囊线虫属(Punctoderaspp.),五沟线虫属(Quinisulcius spp.),穿孔线虫属(Radopholus spp.),例如柑橘穿孔线虫(Radopholus citrophilus)、香蕉穿孔线虫(Radopholus similis),肾状线虫属(Rotylenchulus spp.),盘旋线虫属(Rotylenchus spp.),盾线虫属(Scutellonemaspp.),亚蛇形线虫属(Subanguina spp.),毛刺线虫属(Trichodorus spp.),例如短粗根毛刺线虫(Trichodorus obtusus)、原始毛刺线虫(Trichodorus primitivus),矮化线虫属(Tylenchorhynchus spp.),例如饰环矮化线虫(Tylenchorhynchus annulatus),半穿刺线虫属(Tylenchulus spp.),例如柑橘半穿刺线虫(Tylenchulus semipenetrans),剑线虫属(Xiphinema spp.),例如标准剑线虫(Xiphinema index)。
根据情况,在某些浓度或施用率下,还可将式(I)的化合物用作除草剂、安全剂、生长调节剂或用于改善植物性能的试剂,用作杀微生物剂或杀配子剂,例如用作杀真菌剂、抗霉菌剂、杀细菌剂、杀病毒剂(包括抗类病毒的试剂)或用作抗MLO(类支原体生物)和RLO(类立克次氏体生物)的试剂。根据情况,还可将它们用作用于合成其他活性成分的中间体或前体。
制剂
本发明还涉及作为农药的包含至少一种式(I)的化合物的制剂和由其制备的使用形式,例如浸液、滴液和喷雾液体。任选地,所述使用形式包含其他农药和/或改善作用的佐剂,例如渗透剂,例如植物油(例如菜籽油、葵花油)、矿物油(例如石蜡油)、植物脂肪酸的烷基酯(例如菜籽油甲酯或大豆油甲酯)或烷醇烷氧基化物;和/或铺展剂(spreader),例如烷基硅氧烷和/或盐,例如有机或无机铵盐或鏻盐,例如硫酸铵或磷酸氢二铵;和/或保持促进剂(retention promoter),例如磺基琥珀酸二辛酯或羟丙基瓜儿胶聚合物;和/或保湿剂,例如甘油;和/或肥料,例如含铵、含钾或含磷的肥料。
常规制剂为例如水溶性液剂(SL)、乳液浓缩剂(EC)、水乳剂(EW)、悬浮浓缩剂(SC、SE、FS、OD)、水分散性颗粒剂(WG)、颗粒剂(GR)和胶囊浓缩剂(CS);这些制剂和其他制剂类型例如由国际作物生命组织(Crop Life International)记载于以下文献中:农药说明书(Pesticide Specifications)、联合国粮农组织和世界卫生组织农药说明书开发与使用手册(Manual on development and use of FAO and WHO specifications forpesticides)、联合国粮农组织植物生产与保护文献-173(FAO Plant Production andProtection Papers–173)(由联合国粮农组织/世界卫生组织关于农药说明书的联合会议制订,2004,ISBN:9251048576)。除一种或多种式(I)的化合物外,所述制剂还任选地包含其他农业化学活性成分。
优选包含以下物质的制剂或使用形式:助剂,例如增量剂、溶剂、自发性促进剂、载体、乳化剂、分散剂、防冻剂、灭生物剂、增稠剂;和/或其他助剂,例如佐剂。在本发明的上下文中,佐剂为一种增强制剂的生物效应的组分,而该组分本身不具有任何生物效应。佐剂的实例为促进保持、铺展、对叶子表面的附着或渗透的试剂。
这些制剂以已知的方式制备,例如通过将式(I)的化合物与助剂混合而制备,所述助剂为例如增量剂、溶剂和/或固体载体和/或其他助剂,例如表面活性剂。所述制剂在合适的设备中制备或在施用之前或施用期间制备。
所用的助剂可为适于赋予式(I)的化合物的制剂或由这些制剂制备的使用形式(例如即用型农药如喷雾液体或拌种产品)特定的特性(如某些物理特性、技术特性和/或生物特性)的物质。
合适的增量剂为例如水、极性和非极性有机化学液体,例如选自芳族烃类和非芳族烃类(如石蜡、烷基苯、烷基萘、氯苯)、醇类和多元醇类(如果合适,其还可被取代、醚化和/或酯化)、酮类(如丙酮、环己酮)、酯类(包括脂肪和油)和(聚)醚类、简单的和取代的胺类、酰胺类、内酰胺类(如N-烷基吡咯烷酮)以及内酯类、砜类和亚砜类(如二甲基亚砜)、碳酸酯类和腈类。
如果所用的增量剂为水,则还可使用例如有机溶剂作为助溶剂。可用的液体溶剂主要为:芳族化合物如二甲苯、甲苯或烷基萘,氯代芳族烃类或氯代脂族烃类如氯苯、氯乙烯或二氯甲烷,脂族烃类如环己烷或石蜡,例如石油馏分、矿物油和植物油,醇类如丁醇或乙二醇及其醚类和酯类,酮类如丙酮、甲基乙基酮、甲基异丁基酮或环己酮,强极性溶剂如二甲基甲酰胺和二甲基亚砜,碳酸酯类例如碳酸丙烯酯、碳酸丁烯酯、碳酸二乙酯或碳酸二丁酯,或腈类如乙腈或丙腈。
原则上,可使用所有合适的溶剂。合适的溶剂的实例为芳族烃类,例如二甲苯、甲苯或烷基萘;氯代芳族烃类或氯代脂族烃类,例如氯苯、氯乙烯或二氯甲烷;脂族烃类,例如环己烷、石蜡、石油馏分、矿物油和植物油;醇类,例如甲醇、乙醇、异丙醇、丁醇或乙二醇及其醚类和酯类;酮类,例如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基亚砜,碳酸酯类例如碳酸丙烯酯、碳酸丁烯酯、碳酸二乙酯或碳酸二丁酯,腈类如乙腈或丙腈,以及水。
原则上,可使用所有合适的载体。合适的载体更特别地包括以下物质:例如铵盐和细磨的天然岩石如高岭土、矾土、滑石、白垩、石英、绿坡缕石、蒙脱石或硅藻土,以及细磨的合成岩石如高度分散的二氧化硅、氧化铝,以及天然或合成的硅酸盐、树脂、蜡和/或固体肥料。同样可使用这类载体的混合物。可用于颗粒剂的载体包括:例如粉碎并分级的天然岩石如方解石、大理石、浮石、海泡石、白云石和无机和有机粉末的合成颗粒,以及有机材料如锯屑、纸、椰壳、玉米穗轴和烟草茎的颗粒。
还可使用液化的气态增量剂或溶剂。特别合适的增量剂或载体为在标准温度和大气压力下为气态的那些增量剂或载体,例如气溶胶喷射剂如卤代烃类,以及丁烷、丙烷、氮气和二氧化碳。
具有离子或非离子性质的乳化剂和/或发泡剂、分散剂或润湿剂或这些表面活性物质的混合物的实例为聚丙烯酸的盐、木素磺酸的盐、苯酚磺酸的盐或萘磺酸的盐、环氧乙烷与脂肪醇或与脂肪酸或与脂肪胺的缩聚物、环氧乙烷与取代的酚类(优选烷基酚或芳基酚)的缩聚物、磺基琥珀酸酯的盐、牛磺酸衍生物(优选牛磺酸烷基酯)、羟乙基磺酸盐衍生物、聚乙氧基化的醇类或酚类的磷酸酯、多元醇的脂肪酸酯,以及含有硫酸酯、磺酸酯和磷酸酯的化合物的衍生物,例如烷基芳基聚乙二醇醚、烷基磺酸酯、烷基硫酸酯、芳基磺酸酯、蛋白质水解产物、木素亚硫酸盐废液和甲基纤维素。如果式(I)的化合物之一和/或惰性载体之一不溶于水并且如果在水中进行施用,则表面活性剂的存在是有利的。
可存在于制剂和由其获得的使用形式中的其他助剂包括染料如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,以及有机染料如茜素染料、偶氮染料和金属酞菁染料;以及营养素和微量营养素,如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
可存在的其他组分为稳定剂,如低温稳定剂、防腐剂、抗氧化剂、光稳定剂或改善化学和/或物理稳定性的其他试剂。还可存在发泡剂(foam generator)或消泡剂。
此外,所述制剂和由其获得的使用形式还可包含下列物质作为另外的助剂:粘着剂如羧甲基纤维素,以及粉末、颗粒或胶乳形式的天然和合成聚合物,如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,或天然磷脂类如脑磷脂和卵磷脂以及合成磷脂类。其他助剂可为矿物油和植物油。
如果合适,在所述制剂和由其获得的使用形式中还可存在其他助剂。这类添加剂的实例为香料、保护胶体、粘合剂、胶粘剂、增稠剂、触变剂、渗透剂、保持促进剂、稳定剂、螯合剂、络合剂、保湿剂、铺展剂。通常,式(I)的化合物可与通常用于制剂目的的任何固体或液体添加剂结合。
可用的保持促进剂包括所有那些降低动态表面张力的物质,例如磺基琥珀酸二辛酯;或所有那些增加粘弹性的物质,例如羟丙基瓜儿胶聚合物。
在本发明的上下文中,可用的渗透剂为所有那些通常用于改善农业化学活性成分向植物中渗透的物质。在本发明的上下文中,渗透剂通过其从(通常水性的)施用液体和/或从喷雾涂层渗入植物角质层中并因此增加活性成分在角质层中的移动性的能力来定义。可使用文献(Baur等人,1997,Pesticide Science 51,131-152)中记载的方法来测定该特性。实例包括醇烷氧基化物如椰子脂肪乙氧基化物(10)或异十三烷基乙氧基化物(12);脂肪酸酯类,例如菜籽油甲酯或大豆油甲酯;脂肪胺烷氧基化物,例如牛脂胺乙氧基化物(15);或铵盐和/或鏻盐,例如硫酸铵或磷酸氢二铵。
所述制剂优选包含0.00000001重量%至98重量%的式(I)的化合物,更优选0.01重量%至95重量%的式(I)的化合物,最优选0.5重量%至90重量%的式(I)的化合物,基于制剂的重量计。
在由所述制剂制备的使用形式(特别是农药)中,式(I)的化合物的含量可在宽范围内变化。在使用形式中,式(I)的化合物的浓度通常可为0.00000001重量%至95重量%、优选0.00001重量%至1重量%的式(I)的化合物,基于使用形式的重量计。施用以适于使用形式的常规方式进行。
混合物
式(I)的化合物还可与一种或多种合适的以下物质以混合物的形式使用:杀真菌剂、杀细菌剂、杀螨剂、杀软体动物剂、杀线虫剂、杀昆虫剂、微生物剂、有益生物、除草剂、肥料、驱鸟剂、植物性毒素(phytotonics)、止繁殖剂、安全剂、化学信息素和/或植物生长调节剂,以例如扩大作用谱、延长作用周期、提高作用速率、防止抵抗性或防止抗性的发展。此外,这类活性成分结合物可改善植物生长和/或提高对非生物因素(例如高温或低温)的耐受性、对干旱或对高的含水量或土壤盐渍度的耐受性。还可改善开花和结果性能、优化发芽能力和根系发育、促进采收并提高产量、影响成熟、提高采收产品的品质和/或营养价值、延长采收产品的保存期限和/或改善采收产品的加工性能。
此外,式(I)的化合物还可与其他活性成分或化学信息素如引诱剂和/或驱鸟剂和/或植物激活剂和/或生长调节剂和/或肥料以混合物的形式存在。同样地,式(I)的化合物还可用于改善植物性能,例如生长、采收物的产量和品质。
在本发明的一个特定的实施方案中,在制剂或由这些制剂制备的使用形式中,式(I)的化合物与其他化合物、优选如下文所述的那些化合物以混合物的形式存在。
如果下述化合物之一可以以不同的互变异构形式存在,则这些形式也包括在内,即使在每种情况下没有明确提及。根据情况,如果混合组分基于其官能团能够与合适的碱或酸形成盐,则所有提及的混合组分还可与合适的碱或酸形成盐。
杀昆虫剂/杀螨剂/杀线虫剂
本文中以其通用名称指定的活性成分是已知的并且记载于例如"The PesticideManual",第16版,British Crop Protection Council2012中,或可在因特网(例如,http://www.alanwood.net/pesticides)上检索。所述分类基于在提交本专利申请时可适用的IRAC作用方式分类方案(IRAC Mode of Action Classification Scheme)。
(1)乙酰胆碱酯酶(AChE)抑制剂,例如选自以下物质的氨基甲酸酯类:棉铃威(alanycarb)、涕灭威(aldicarb)、恶虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮砜威(butoxycarboxim)、甲萘威(carbaryl)、克百威(carbofuran)、丁硫克百威(carbosulfan)、乙硫苯威(ethiofencarb)、仲丁威(fenobucarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、甲硫威(methiocarb)、灭多威(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混杀威(trimethacarb)、灭除威(XMC)和灭杀威(xylylcarb);或选自以下物质的有机磷酸酯类:乙酰甲胺磷(acephate)、甲基吡啶磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、甲基谷硫磷(azinphos-methyl)、硫线磷(cadusafos)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、甲基毒死蜱(chlorpyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(dichlorvos)/DDVP、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、苯硫磷(EPN)、乙硫磷(ethion)、灭线磷(ethoprophos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟硫磷(fenitrothion)、倍硫磷(fenthion)、噻唑膦(fosthiazate)、庚烯磷(heptenophos)、imicyafos、异柳磷(isofenphos)、O-(甲氧基氨基硫代磷酰基)水杨酸异丙酯(isopropylO-(methoxyaminothiophosphoryl)salicylate)、异噁唑磷(isoxathion)、马拉松(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、亚砜磷(oxydemeton-methyl)、甲基对硫磷(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、甲基嘧啶磷(pirimiphos-methyl)、丙溴磷(profenofos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(triclorfon)和蚜灭磷(vamidothion)。
(2)GABA门控氯化物通道阻断剂,优选选自以下物质的环戊二烯有机氯类:氯丹(chlordane)和硫丹(endosulfan);或选自以下物质的苯基吡唑类(phenylpyrazoles(fiproles)):乙虫腈(ethiprole)和氟虫腈(fipronil)。
(3)钠通道调节剂,优选选自以下物质的拟除虫菊酯类(pyrethroids):氟丙菊酯(acrinathrin)、丙烯菊酯(allethrin)、d-顺式-反式丙烯菊酯、d-反式丙烯菊酯、联苯菊酯(bifenthrin)、生物丙烯菊酯(bioallethrin)、生物丙烯菊酯S-环戊烯基同分异构体、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、β-氟氯氰菊酯、三氟氯氰菊酯(cyhalothrin)、λ-三氟氯氰菊酯、γ-三氟氯氰菊酯、氯氰菊酯(cypermethrin)、α-氯氰菊酯、β-氯氰菊酯、θ-氯氰菊酯、ζ-氯氰菊酯、苯醚氰菊酯[(1R)-反式同分异构体](cyphenothrin[(1R)-trans isomer])、溴氰菊酯(deltamethrin)、右旋烯炔菊酯[(EZ)-(1R)同分异构体](empenthrin[(EZ)-(1R)isomer])、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、氰戊菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、τ-氟胺氰菊酯(tau-fluvalinate)、苄螨醚(halfenprox)、炔咪菊酯(imiprothrin)、噻嗯菊酯(kadethrin)、momfluorothrin、氯菊酯(permethrin)、苯醚菊酯[(1R)-反式同分异构体](phenothrin[(1R)-trans isomer])、右旋炔丙菊酯(prallethrin)、除虫菊素(除虫菊)(pyrethrins(pyrethrum))、苄呋菊酯(resmethrin)、氟硅菊酯(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、胺菊酯[(1R)同分异构体](tetramethrin[(1R)isomer)])、四溴菊酯(tralomethrin)和四氟苯菊酯(transfluthrin)或滴滴涕(DDT)或甲氧滴滴涕(methoxychlor)。
(4)烟碱能乙酰胆碱受体(nAChR)竞争调节剂,优选选自以下物质的新烟碱类(neonicotinoids):啶虫脒(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、噻虫啉(thiacloprid)和噻虫嗪(thiamethoxam),或烟碱(nicotine);或选自氟啶虫胺腈(sulfoxaflor)的亚砜亚胺类(sulfoximines);或选自氟吡呋喃酮(flupyradifurone)的丁烯酸内酯类(butenolides)。
(5)烟碱能乙酰胆碱受体(nAChR)变构调节剂,优选选自乙基多杀菌素(spinetoram)和多杀菌素(spinosad)的多杀菌素类(spinosyns)。
(6)谷氨酸酯门控氯化物通道(GluCl)变构调节剂,优选选自以下物质的阿维菌素类(avermectins)/米尔倍霉素类(milbemycins):阿维菌素(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectin benzoate)、雷皮菌素(lepimectin)和弥拜菌素(milbemectin)。
(7)保幼激素模拟物,优选选自以下物质的保幼激素类似物:烯虫乙酯(hydroprene)、烯虫炔酯(kinoprene)和烯虫酯(methoprene),或苯氧威(fenoxycarb)或吡丙醚(pyriproxyfen)。
(8)各种非特异性(多位点)抑制剂,优选选自以下物质的烷基卤化物类:甲基溴和其他烷基卤化物;或氯化苦(chloropicrin)或硫酰氟(sulphuryl fluoride)或硼砂(borax)或吐酒石(tartar emetic);或选自diazomet和威百亩(metam)的异氰酸甲酯产生剂。
(9)弦音器官(chordotonal organ)的TRPV通道调节剂,选自吡蚜酮(pymetrozine)和pyrifluquinazone。
(10)螨生长抑制剂,选自四螨嗪(clofentezine)、噻螨酮(hexythiazox)、氟螨嗪(diflovidazin)和乙螨唑(etoxazole)。
(11)昆虫中肠膜微生物干扰剂,选自:苏云金芽孢杆菌以色列亚种(Bacillusthuringiensis subspecies israelensis)、球形芽孢杆菌(Bacillus sphaericus)、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensis subspecies aizawai)、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subspecies kurstaki)、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subspecies tenebrionis)和选自以下物质的B.t植物蛋白:Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb和Cry34Ab1/35Ab1。
(12)线粒体ATP合酶抑制剂,优选选自丁醚脲(diafenthiuron)的ATP干扰剂;或选自以下物质的有机锡化合物:三唑锡(azocyclotin)、三环锡(cyhexatin)和苯丁锡(fenbutatin oxide),或炔螨特(propargite),或四氯杀螨砜(tetradifon)。
(13)通过间隔质子梯度作用的氧化磷酸化解偶联剂,选自:溴虫腈(chlorfenapyr)、二硝甲酚(DNOC)和氟虫胺(sulfluramid)。
(14)烟碱能乙酰胆碱受体通道阻断剂,选自:杀虫磺(bensultap)、杀螟丹盐酸盐(cartap hydrochloride)、杀虫环(thiocyclam)和杀虫双(thiosultap-sodium)。
(15)0型几丁质生物合成抑制剂,选自:双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、二氟脲(diflubenzuron)、氟环脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、虱螨脲(lufenuron)、氟酰脲(novaluron)、多氟脲(noviflumuron)、氟苯脲(teflubenzuron)和杀铃脲(triflumuron)。
(16)1型几丁质生物合成抑制剂,选自:噻嗪酮(buprofezin)。
(17)蜕皮干扰剂(尤其是对于双翅目),选自:灭蝇胺(cyromazine)。
(18)蜕皮激素受体激动剂,选自:环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)和虫酰肼(tebufenozide)。
(19)章鱼胺受体激动剂,选自:双甲脒(amitraz)。
(20)线粒体复合物III电子传递抑制剂,选自:氟蚁腙(hydramethylnon)、灭螨醌(acequinocyl)和嘧螨酯(fluacrypyrim)。
(21)线粒体复合物I电子传递抑制剂,优选选自以下物质的METI杀螨剂类:喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨灵(pyridaben)、吡螨胺(tebufenpyrad)和唑虫酰胺(tolfenpyrad),或鱼藤酮(rotenone)(鱼藤属(Derris))。
(22)电压依赖型钠通道阻断剂,选自:茚虫威(indoxacarb)和氰氟虫腙(metaflumizone)。
(23)乙酰基辅酶A(CoA)羧化酶抑制剂,优选选自以下物质的特窗酸和特特拉姆酸(tetramic acid)衍生物:螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)和螺虫乙酯(spirotetramat)。
(24)线粒体复合物IV电子传递抑制剂,优选选自以下物质的膦类化合物:磷化铝、磷化钙、膦和磷化锌;或选自以下物质的氰化物类:氰化钙、氰化钾和氰化钠。
(25)线粒体复合物II电子传递抑制剂,优选选自以下物质的β-酮腈衍生物类(beta-keto nitrile derivatives):腈吡螨酯(cyenopyrafen)和丁氟螨酯(cyflumetofen);或羧酰苯胺类(carboxanilide),选自:pyflubumide。
(28)兰尼碱(ryanodine)受体调节剂,优选选自以下物质的二酰胺类:氯虫苯甲酰胺(chlorantraniliprole)、氰虫酰胺(cyantraniliprole)和氟虫双酰胺(flubendiamide),
(29)弦音器官调节剂(具有不确定的靶结构),选自:氟啶虫酰胺(flonicamide)。
(30)其他活性成分,选自:啶喃环丙虫酯(afidopyropen)、阿福拉纳(afoxolaner)、印楝素(azadirachtin)、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴虫氟苯双酰胺(broflanilide)、溴螨酯(bromopropylate)、灭螨猛(chinomethionat)、氯丙炔菊酯(chloroprallethrin)、冰晶石(cryolite)、环溴虫酰胺(cyclaniliprole)、环氧虫啶(cycloxaprid)、氯氟氰虫酰胺(cyhalodiamide)、dicloromezotiaz、三氯杀螨醇(dicofol)、ε-甲氧苄氟菊酯(epsilon metofluthrin)、epsilon momfluthrin、flometoquin、fluazaindolizine、联氟砜(fluensulfone)、嘧虫胺(flufenerim)、氟菌螨酯(flufenoxystrobin)、丁虫腈(flufiprole)、fluhexafon、氟吡菌酰胺(fluopyram)、氟雷拉纳(fluralaner)、fluxametamide、呋喃虫酰肼(fufenozide)、戊吡虫胍(guadipyr)、heptafluthrin、氯噻啉(imidaclothiz)、异菌脲(iprodione)、κ-联苯菊酯(kappa-bifenthrin)、κ-七氟菊酯(kappa-tefluthrin)、lotilaner、氯氟醚菊酯(meperfluthrin)、哌虫啶(paichongding)、啶虫丙醚(pyridalyl)、pyrifluquinazon、嘧螨胺(pyriminostrobin)、spirobudiclofen、四氟醚菊酯(tetramethylfluthrin)、氟氰虫酰胺(tetraniliprole)、四氯虫酰胺(tetrachlorantraniliprole)、tigolaner、tioxazafen、硫氟肟醚(thiofluoximate)、三氟苯嘧啶(triflumezopyrim)和碘甲烷(iodomethane);另外基于坚强芽孢杆菌(Bacillus firmus)的制剂(I-1582,BioNeem,Votivo),和以下化合物:1-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯基}-3-(三氟甲基)-1H-1,2,4-三唑-5-胺(由WO2006/043635获知)(CAS 885026-50-6)、{1'-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]-5-氟螺[吲哚-3,4'-哌啶]-1(2H)-基}(2-氯吡啶-4-基)甲酮(由WO2003/106457获知)(CAS 637360-23-7)、2-氯-N-[2-{1-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]哌啶-4-基}-4-(三氟甲基)苯基]异烟酰胺(由WO2006/003494获知)(CAS 872999-66-1)、3-(4-氯-2,6-二甲基苯基)-4-羟基-8-甲氧基-1,8-二氮杂螺[4.5]癸-3-烯-2-酮(由WO 2010052161获知)(CAS 1225292-17-0)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-2-氧代-1,8-二氮杂螺[4.5]癸-3-烯-4-基乙基碳酸酯(由EP 2647626获知)(CAS-1440516-42-6)、4-(丁-2-炔-1-基氧基)-6-(3,5-二甲基哌啶-1-基)-5-氟嘧啶(由WO2004/099160获知)(CAS 792914-58-0)、PF1364(由JP2010/018586获知)(CAS登记号1204776-60-2)、N-[(2E)-1-[(6-氯吡啶-3-基)甲基]吡啶-2(1H)-亚基]-2,2,2-三氟乙酰胺(由WO2012/029672获知)(CAS 1363400-41-2)、(3E)-3-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-1,1,1-三氟丙-2-酮(由WO2013/144213获知)(CAS 1461743-15-6)、N-[3-(苄基氨基甲酰基)-4-氯苯基]-1-甲基-3-(五氟乙基)-4-(三氟甲基)-1H-吡唑-5-甲酰胺(由WO2010/051926获知)(CAS 1226889-14-0)、5-溴-4-氯-N-[4-氯-2-甲基-6-(甲基氨基甲酰基)苯基]-2-(3-氯-2-吡啶基)吡唑-3-甲酰胺(由CN103232431获知)(CAS 1449220-44-3)、4-[5-(3,5-二氯苯基)-4,5-二氢-5-(三氟甲基)-3-异噁唑基]-2-甲基-N-(顺式-1-氧代-3-硫杂环丁烷基)苯甲酰胺、4-[5-(3,5-二氯苯基)-4,5-二氢-5-(三氟甲基)-3-异噁唑基]-2-甲基-N-(反式-1-氧代-3-硫杂环丁烷基)苯甲酰胺和4-[(5S)-5-(3,5-二氯苯基)-4,5-二氢-5-(三氟甲基)-3-异噁唑基]-2-甲基-N-(顺式-1-氧代-3-硫杂环丁烷基)苯甲酰胺(由WO 2013/050317 A1获知)(CAS 1332628-83-7)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亚磺酰基]丙酰胺、(+)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亚磺酰基]丙酰胺和(-)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亚磺酰基]丙酰胺(由WO 2013/162715 A2、WO 2013/162716 A2、US 2014/0213448 A1获知)(CAS 1477923-37-7)、5-[[(2E)-3-氯-2-丙烯-1-基]氨基]-1-[2,6-二氯-4-(三氟甲基)苯基]-4-[(三氟甲基)亚磺酰基]-1H-吡唑-3-甲腈(由CN 101337937 A获知)(CAS1105672-77-2)、3-溴-N-[4-氯-2-甲基-6-[(甲基氨基)硫代甲基]苯基]-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺(Liudaibenjiaxuanan,由CN 103109816 A获知)(CAS 1232543-85-9);N-[4-氯-2-[[(1,1-二甲基乙基)氨基]羰基]-6-甲基苯基]-1-(3-氯-2-吡啶基)-3-(氟甲氧基)-1H-吡唑-5-甲酰胺(由WO 2012/034403 A1获知)(CAS 1268277-22-0)、N-[2-(5-氨基-1,3,4-噻二唑-2-基)-4-氯-6-甲基苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺(由WO 2011/085575 A1获知)(CAS 1233882-22-8)、4-[3-[2,6-二氯-4-[(3,3-二氯-2-丙烯-1-基)氧基]苯氧基]丙氧基]-2-甲氧基-6-(三氟甲基)嘧啶(由CN 101337940 A获知)(CAS 1108184-52-6);(2E)-2-[2-(4-氰基苯基)-1-[3-(三氟甲基)苯基]亚乙基]-N-[4-(二氟甲氧基)苯基]肼甲酰胺和2(Z)-2-[2-(4-氰基苯基)-1-[3-(三氟甲基)苯基]亚乙基]-N-[4-(二氟甲氧基)苯基]肼甲酰胺(由CN 101715774 A获知)(CAS 1232543-85-9);环丙烷甲酸3-(2,2-二氯乙烯基)-2,2-二甲基-4-(1H-苯并咪唑-2-基)苯酯(由CN 103524422A获知)(CAS 1542271-46-4);(4aS)-7-氯-2,5-二氢-2-[[(甲氧基羰基)[4-[(三氟甲基)硫基]苯基]氨基]羰基]茚并[1,2-e][1,3,4]噁二嗪-4a(3H)-甲酸甲酯(由CN 102391261 A获知)(CAS 1370358-69-2);6-脱氧-3-O-乙基-2,4-二-O-甲基-1-[N-[4-[1-[4-(1,1,2,2,2-五氟乙氧基)苯基]-1H-1,2,4-三唑-3-基]苯基]氨基甲酸酯]-α-L-吡喃甘露糖(由US2014/0275503 A1获知)(CAS 1181213-14-8);8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基哒嗪-3-基)-3-氮杂二环[3.2.1]辛烷(CAS 1253850-56-4)、(8-反式)-8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基哒嗪-3-基)-3-氮杂二环[3.2.1]辛烷(CAS 933798-27-7)、(8-顺式)-8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基哒嗪-3-基)-3-氮杂二环[3.2.1]辛烷(由WO 2007040280 A1、WO 2007040282 A1获知)(CAS934001-66-8)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)硫基]丙酰胺(由WO 2015/058021 A1、WO 2015/058028 A1获知)(CAS 1477919-27-9)和N-[4-(氨基硫代甲基)-2-甲基-6-[(甲基氨基)羰基]苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺(由CN 103265527 A获知)(CAS 1452877-50-7)、5-(1,3-二氧杂环己-2-基)-4-[[4-(三氟甲基)苯基]甲氧基]嘧啶(由WO 2013/115391 A1获知)(CAS 1449021-97-9)、3-(4-氯-2,6-二甲基苯基)-4-羟基-8-甲氧基-1-甲基-1,8-二氮杂螺[4.5]癸-3-烯-2-酮(由WO 2010/066780 A1、WO 2011/151146 A1获知)(CAS 1229023-34-0)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-1,8-二氮杂螺[4.5]癸烷-2,4-二酮(由WO 2014/187846 A1获知)(CAS 1638765-58-8)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-2-氧代-1,8-二氮杂螺[4.5]癸-3-烯-4-基甲酸乙酯(由WO 2010/066780 A1、WO 2011151146 A1获知)(CAS1229023-00-0)、N-[1-[(6-氯-3-吡啶基)甲基]-2(1H)-吡啶亚基]-2,2,2-三氟乙酰胺(由DE 3639877 A1、WO 2012029672 A1获知)(CAS 1363400-41-2)、[N(E)]-N-[1-[(6-氯-3-吡啶基)甲基]-2(1H)-吡啶亚基]-2,2,2-三氟乙酰胺(由WO 2016005276 A1获知)(CAS1689566-03-7)、[N(Z)]-N-[1-[(6-氯-3-吡啶基)甲基]-2(1H)-吡啶亚基]-2,2,2-三氟乙酰胺(CAS 1702305-40-5)、3-内-3-[2-丙氧基-4-(三氟甲基)苯氧基]-9-[[5-(三氟甲基)-2-吡啶基]氧基]-9-氮杂双环[3.3.1]壬烷(由WO 2011/105506 A1、WO 2016/133011 A1获知)(CAS 1332838-17-1)。
杀真菌剂
本文中以其通用名称指定的活性成分是已知的并且记载于例如"PesticideManual"(第16版,British Crop Protection Council)中或可在因特网(例如:http://www.alanwood.net/pesticides)上检索。
根据情况,如果混合组分基于其官能团能够与合适的碱或酸形成盐,则在(1)至(15)类中提及的所有混合组分均可与合适的碱或酸形成盐。根据情况,在(1)至(15)类中提及的所有杀真菌混合组分可包括互变异构形式。
1)麦角固醇生物合成抑制剂,例如(1.001)环丙唑醇(cyproconazole)、(1.002)苯醚甲环唑(difenoconazole)、(1.003)氟环唑(epoxiconazole)、(1.004)环酰菌胺(fenhexamid)、(1.005)苯锈啶(fenpropidin)、(1.006)丁苯吗啉(fenpropimorph)、(1.007)胺苯吡菌酮(fenpyrazamine)、(1.008)氟喹唑(fluquinconazole)、(1.009)粉唑醇(flutriafol)、(1.010)抑霉唑(imazalil)、(1.011)抑霉唑硫酸盐(imazalil sulfate)、(1.012)种菌唑(ipconazole)、(1.013)叶菌唑(metconazole)、(1.014)腈菌唑(myclobutanil)、(1.015)多效唑(paclobutrazol)、(1.016)咪鲜胺(prochloraz)、(1.017)丙环唑(propiconazole)、(1.018)丙硫菌唑(prothioconazole)、(1.019)啶菌噁唑(pyrisoxazole)、(1.020)螺环菌胺(spiroxamine)、(1.021)戊唑醇(tebuconazole)、(1.022)四氟醚唑(tetraconazole)、(1.023)三唑醇(triadimenol)、(1.024)十三吗啉(tridemorph)、(1.025)灭菌唑(triticonazole)、(1.026)(1R,2S,5S)-5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.027)(1S,2R,5R)-5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.028)(2R)-2-(1-氯环丙基)-4-[(1R)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.029)(2R)-2-(1-氯环丙基)-4-[(1S)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.030)(2R)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.031)(2S)-2-(1-氯环丙基)-4-[(1R)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.032)(2S)-2-(1-氯环丙基)-4-[(1S)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.033)(2S)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.034)(R)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(1.035)(S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(1.036)[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(1.037)1-({(2R,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧戊环-2-基}甲基)-1H-1,2,4-三唑、(1.038)1-({(2S,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧戊环-2-基}甲基)-1H-1,2,4-三唑、(1.039)1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.040)1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.041)1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.042)2-[(2R,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.043)2-[(2R,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.044)2-[(2R,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.045)2-[(2R,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.046)2-[(2S,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.047)2-[(2S,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.048)2-[(2S,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.049)2-[(2S,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.050)2-[1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.051)2-[2-氯-4-(2,4-二氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.052)2-[2-氯-4-(4-氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.053)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.054)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)戊-2-醇、(1.055)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.056)2-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.057)2-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.058)2-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.059)5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.060)5-(烯丙基硫烷基)-1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.061)5-(烯丙基硫烷基)-1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.062)5-(烯丙基硫烷基)-1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.063)N'-(2,5-二甲基-4-{[3-(1,1,2,2-四氟乙氧基)苯基]硫烷基}苯基)-N-乙基-N-甲基酰亚氨基甲酰胺、(1.064)N'-(2,5-二甲基-4-{[3-(2,2,2-三氟乙氧基)苯基]硫烷基}苯基)-N-乙基-N-甲基酰亚氨基甲酰胺、(1.065)N'-(2,5-二甲基-4-{[3-(2,2,3,3-四氟丙氧基)苯基]硫烷基}苯基)-N-乙基-N-甲基酰亚氨基甲酰胺、(1.066)N'-(2,5-二甲基-4-{[3-(五氟乙氧基)苯基]硫烷基}苯基)-N-乙基-N-甲基酰亚氨基甲酰胺、(1.067)N'-(2,5-二甲基-4-{3-[(1,1,2,2-四氟乙基)硫烷基]苯氧基}苯基)-N-乙基-N-甲基酰亚氨基甲酰胺、(1.068)N'-(2,5-二甲基-4-{3-[(2,2,2-三氟乙基)硫烷基]苯氧基}苯基)-N-乙基-N-甲基酰亚氨基甲酰胺、(1.069)N'-(2,5-二甲基-4-{3-[(2,2,3,3-四氟丙基)硫烷基]苯氧基}苯基)-N-乙基-N-甲基酰亚氨基甲酰胺、(1.070)N'-(2,5-二甲基-4-{3-[(五氟乙基)硫烷基]苯氧基}苯基)-N-乙基-N-甲基酰亚氨基甲酰胺、(1.071)N'-(2,5-二甲基-4-苯氧基苯基)-N-乙基-N-甲基酰亚氨基甲酰胺、(1.072)N'-(4-{[3-(二氟甲氧基)苯基]硫烷基}-2,5-二甲基苯基)-N-乙基-N-甲基酰亚氨基甲酰胺、(1.073)N'-(4-{3-[(二氟甲基)硫烷基]苯氧基}-2,5-二甲基苯基)-N-乙基-N-甲基酰亚氨基甲酰胺、(1.074)N'-[5-溴-6-(2,3-二氢-1H-茚-2-基氧基)-2-甲基吡啶-3-基]-N-乙基-N-甲基酰亚氨基甲酰胺、(1.075)N'-{4-[(4,5-二氯-1,3-噻唑-2-基)氧基]-2,5-二甲基苯基}-N-乙基-N-甲基酰亚氨基甲酰胺、(1.076)N'-{5-溴-6-[(1R)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基酰亚氨基甲酰胺、(1.077)N'-{5-溴-6-[(1S)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基酰亚氨基甲酰胺、(1.078)N'-{5-溴-6-[(顺式-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基酰亚氨基甲酰胺、(1.079)N'-{5-溴-6-[(反式-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基酰亚氨基甲酰胺、(1.080)N'-{5-溴-6-[1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基酰亚氨基甲酰胺、(1.081)mefentrifluconazole、(1.082)ipfentrifluconazole。
2)呼吸链复合物I或II抑制剂,例如(2.001)苯并烯氟菌唑(benzovindiflupyr)、(2.002)联苯吡菌胺(bixafen)、(2.003)啶酰菌胺(boscalid)、(2.004)萎锈灵(carboxin)、(2.005)氟吡菌酰胺(fluopyram)、(2.006)氟酰胺(flutolanil)、(2.007)氟唑菌酰胺(fluxapyroxad)、(2.008)呋吡菌胺(furametpyr)、(2.009)异丙噻菌胺(isofetamid)、(2.010)吡唑萘菌胺(isopyrazam)(反式差向异构对映体1R,4S,9S)、(2.011)吡唑萘菌胺(反式差向异构对映体1S,4R,9R)、(2.012)吡唑萘菌胺(反式差向异构外消旋体1RS,4SR,9SR)、(2.013)吡唑萘菌胺(顺式差向异构外消旋体1RS,4SR,9RS与反式差向异构外消旋体1RS,4SR,9SR的混合物)、(2.014)吡唑萘菌胺(顺式差向异构对映体1R,4S,9R)、(2.015)吡唑萘菌胺(顺式差向异构对映体1S,4R,9S)、(2.016)吡唑萘菌胺(顺式差向异构外消旋体1RS,4SR,9RS)、(2.017)戊苯吡菌胺(penflufen)、(2.018)吡噻菌胺(penthiopyrad)、(2.019)氟唑菌酰羟胺(pydiflumetofen)、(2.020)pyraziflumid、(2.021)氟唑环菌胺(sedaxane)、(2.022)1,3-二甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.023)1,3-二甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.024)1,3-二甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.025)1-甲基-3-(三氟甲基)-N-[2'-(三氟甲基)联苯-2-基]-1H-吡唑-4-甲酰胺、(2.026)2-氟-6-(三氟甲基)-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)苯甲酰胺、(2.027)3-(二氟甲基)-1-甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.028)3-(二氟甲基)-1-甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.029)3-(二氟甲基)-1-甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.030)3-(二氟甲基)-N-(7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1-甲基-1H-吡唑-4-甲酰胺、(2.031)3-(二氟甲基)-N-[(3R)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(2.032)3-(二氟甲基)-N-[(3S)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(2.033)5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺、(2.034)N-(2-环戊基-5-氟苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.035)N-(2-叔丁基-5-甲基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.036)N-(2-叔丁基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.037)N-(5-氯-2-乙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.038)N-(5-氯-2-异丙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.039)N-[(1R,4S)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-桥亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.040)N-[(1S,4R)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-桥亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.041)N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.042)N-[2-氯-6-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.043)N-[3-氯-2-氟-6-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.044)N-[5-氯-2-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.045)N-环丙基-3-(二氟甲基)-5-氟-1-甲基-N-[5-甲基-2-(三氟甲基)苄基]-1H-吡唑-4-甲酰胺、(2.046)N-环丙基-3-(二氟甲基)-5-氟-N-(2-氟-6-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(2.047)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基-5-甲基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(2.048)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基苄基)-1-甲基-1H-吡唑-4-硫代甲酰胺、(2.049)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(2.050)N-环丙基-3-(二氟甲基)-5-氟-N-(5-氟-2-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(2.051)N-环丙基-3-(二氟甲基)-N-(2-乙基-4,5-二甲基苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.052)N-环丙基-3-(二氟甲基)-N-(2-乙基-5-氟苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.053)N-环丙基-3-(二氟甲基)-N-(2-乙基-5-甲基苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.054)N-环丙基-N-(2-环丙基-5-氟苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.055)N-环丙基-N-(2-环丙基-5-甲基苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(2.056)N-环丙基-N-(2-环丙基苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺。
3)呼吸链复合物III抑制剂,例如(3.001)唑嘧菌胺(ametoctradin)、(3.002)安美速(amisulbrom)、(3.003)嘧菌酯(azoxystrobin)、(3.004)甲香菌酯(coumethoxystrobin)、(3.005)丁香菌酯(coumoxystrobin)、(3.006)氰霜唑(cyazofamid)、(3.007)醚菌胺(dimoxystrobin)、(3.008)烯肟菌酯(enoxastrobin)、(3.009)恶唑菌酮(famoxadon)、(3.010)咪唑菌酮(fenamidon)、(3.011)氟菌螨酯(flufenoxystrobin)、(3.012)氟嘧菌酯(fluoxastrobin)、(3.013)醚菌酯(kresoxim-methyl)、(3.014)苯氧菌胺(metominostrobin)、(3.015)肟醚菌胺(orysastrobin)、(3.016)啶氧菌酯(picoxystrobin)、(3.017)唑菌胺酯(pyraclostrobin)、(3.018)唑胺菌酯(pyrametostrobin)、(3.019)唑菌酯(pyraoxystrobin)、(3.020)肟菌酯(trifloxystrobin)、(3.021)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯基乙烯基]氧基}苯基)亚乙基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺、(3.022)(2E,3Z)-5-{[1-(4-氯苯基)-1H-吡唑-3-基]氧基}-2-(甲氧基亚氨基)-N,3-二甲基戊-3-烯酰胺、(3.023)(2R)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺、(3.024)(2S)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺、(3.025)(3S,6S,7R,8R)-8-苄基-3-[({3-[(异丁酰氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧杂环壬烷-7-基2-甲基丙酸酯、(3.026)2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺、(3.027)N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰氨基-2-羟基苯甲酰胺、(3.028)(2E,3Z)-5-{[1-(4-氯-2-氟苯基)-1H-吡唑-3-基]氧基}-2-(甲氧基亚氨基)-N,3-二甲基戊-3-烯酰胺、(3.029){5-[3-(2,4-二甲基苯基)-1H-吡唑-1-基]-2-甲基苄基}氨基甲酸甲酯。
4)有丝分裂和细胞分裂抑制剂,例如(4.001)多菌灵(carbendazim)、(4.002)乙霉威(diethofencarb)、(4.003)噻唑菌胺(ethaboxam)、(4.004)氟吡菌胺(fluopicolid)、(4.005)戊菌隆(pencycuron)、(4.006)噻菌灵(thiabendazole)、(4.007)甲基硫菌灵(thiophanate-methyl)、(4.008)苯酰菌胺(zoxamide)、(4.009)3-氯-4-(2,6-二氟苯基)-6-甲基-5-苯基哒嗪、(4.010)3-氯-5-(4-氯苯基)-4-(2,6-二氟苯基)-6-甲基哒嗪、(4.011)3-氯-5-(6-氯吡啶-3-基)-6-甲基-4-(2,4,6-三氟苯基)哒嗪、(4.012)4-(2-溴-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.013)4-(2-溴-4-氟苯基)-N-(2-溴-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.014)4-(2-溴-4-氟苯基)-N-(2-溴苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.015)4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.016)4-(2-溴-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.017)4-(2-溴-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.018)4-(2-氯-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.019)4-(2-氯-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.020)4-(2-氯-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.021)4-(2-氯-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.022)4-(4-氯苯基)-5-(2,6-二氟苯基)-3,6-二甲基哒嗪、(4.023)N-(2-溴-6-氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.024)N-(2-溴苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.025)N-(4-氯-2,6-二氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺。
5)具有多位点活性能力的化合物,例如(5.001)波尔多混合剂(Bordeauxmixture)、(5.002)敌菌丹(captafol)、(5.003)克菌丹(captan)、(5.004)百菌清(chlorthalonil)、(5.005)氢氧化铜、(5.006)环烷酸铜、(5.007)氧化铜、(5.008)氯氧化铜、(5.009)硫酸铜(2+)、(5.010)二氰蒽醌(dithianon)、(5.011)多果定(dodin)、(5.012)灭菌丹(folpet)、(5.013)代森锰锌(mancozeb)、(5.014)代森锰(maneb)、(5.015)代森联(metiram)、(5.016)代森联锌(zinc metiram)、(5.017)羟基喹啉铜(copper oxine)、(5.018)甲基代森锌(propineb)、(5.019)硫和包括多硫化钙的硫制剂、(5.020)福美双(thiram)、(5.021)代森锌(zineb)、(5.022)福美锌(ziram)、(5.023)6-乙基-5,7-二氧代-6,7-二氢-5H-吡咯并[3’,4’:5,6][1,4]二噻英并[2,3-c][1,2]噻唑-3-甲腈。
6)能引发宿主防御的化合物,例如(6.001)苯并噻二唑(acibenzolar-S-methyl)、(6.002)异噻菌胺(isotianil)、(6.003)烯丙苯噻唑(probenazole)、(6.004)噻酰菌胺(tiadinil)。
7)氨基酸和/或蛋白质生物合成抑制剂,例如(7.001)嘧菌环胺(cyprodinil)、(7.002)春雷霉素(kasugamycin)、(7.003)春雷霉素盐酸盐水合物(kasugamycinhydrochloride hydrate)、(7.004)氧四环素(oxytetracycline)、(7.005)嘧霉胺(pyrimethanil)、(7.006)3-(5-氟-3,3,4,4-四甲基-3,4-二氢异喹啉-1-基)喹啉。
8)ATP产生抑制剂,例如(8.001)硅噻菌胺(silthiofam)。
9)细胞壁合成抑制剂,例如(9.001)苯噻菌胺(benthiavalicarb)、(9.002)烯酰吗啉(dimethomorph)、(9.003)氟吗啉(flumorph)、(9.004)异丙菌胺(iprovalicarb)、(9.005)双炔酰菌胺(mandipropamid)、(9.006)吡吗啉(pyrimorph)、(9.007)霜霉灭(valifenalate)、(9.008)(2E)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮、(9.009)(2Z)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮。
10)脂质和膜合成抑制剂,例如(10.001)霜霉威(propamocarb)、(10.002)霜霉威盐酸盐(propamocarb hydrochloride)、(10.003)甲基立枯磷(tolclofos-methyl)。
11)黑色素生物合成抑制剂,例如(11.001)三环唑(tricyclazole)、(11.002)2,2,2-三氟乙基{3-甲基-1-[(4-甲基苯甲酰基)氨基]丁-2-基}氨基甲酸酯。
12)核酸合成抑制剂,例如(12.001)苯霜灵(benalaxyl)、(12.002)精苯霜灵(benalaxyl-M)(kiralaxyl)、(12.003)甲霜灵(metalaxyl)、(12.004)高效甲霜灵(metalaxyl-M)(精甲霜灵(mefenoxam))。
13)信号转导抑制剂,例如(13.001)咯菌腈(fludioxonil)、(13.002)异菌脲(iprodione)、(13.003)腐霉利(procymidone)、(13.004)丙氧喹啉(proquinazid)、(13.005)喹氧灵(quinoxyfen)、(13.006)乙烯菌核利(vinclozolin)。
14)可用作解偶联剂的化合物,例如(14.001)氟啶胺(fluazinam)、(14.002)消螨多(meptyldinocap)。
15)其他化合物,例如(15.001)脱落酸(abscisic acid)、(15.002)苯噻硫氰(benthiazole)、(15.003)bethoxazin、(15.004)卡巴西霉素(capsimycin)、(15.005)香芹酮(carvone)、(15.006)灭螨猛(chinomethionat)、(15.007)硫杂灵(cufraneb)、(15.008)环氟菌胺(cyflufenamid)、(15.009)霜脲氰(cymoxanil)、(15.010)环丙磺酰胺(cyprosulfamide)、(15.011)flutianil、(15.012)三乙膦酸铝(fosetyl-aluminium)、(15.013)三乙膦酸钙(fosetyl-calcium)、(15.014)三乙膦酸钠(fosetyl-sodium)、(15.015)异硫氰酸甲酯(methyl isothiocyanate)、(15.016)苯菌酮(metrafenon)、(15.017)米多霉素(mildiomycin)、(15.018)纳他霉素(natamycin)、(15.019)福美镍(nickel dimethyldithiocarbamate)、(15.020)酞菌酯(nitrothal-isopropyl)、(15.021)oxamocarb、(15.022)氟噻唑吡乙酮(oxathiapiprolin)、(15.023)oxyfenthiin、(15.024)五氯苯酚及其盐、(15.025)膦酸及其盐、(15.026)霜霉威乙膦酸盐(propamocarb-fosetylate)、(15.027)pyriofenone(chlazafenone)、(15.028)异丁乙氧喹啉(tebufloquin)、(15.029)叶枯酞(tecloftalam)、(15.030)甲磺菌胺(tolnifanide)、(15.031)1-(4-{4-[(5R)-5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.032)1-(4-{4-[(5S)-5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.033)2-(6-苄基吡啶-2-基)喹唑啉、(15.034)2,6-二甲基-1H,5H-[1,4]二噻英并[2,3-c:5,6-c']二吡咯-1,3,5,7(2H,6H)-四酮、(15.035)2-[3,5-双(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.036)2-[3,5-双(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氯-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.037)2-[3,5-双(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氟-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.038)2-[6-(3-氟-4-甲氧基苯基)-5-甲基吡啶-2-基]喹唑啉、(15.039)2-{(5R)-3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯、(15.040)2-{(5S)-3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯、(15.041)2-{2-[(7,8-二氟-2-甲基喹啉-3-基)氧基]-6-氟苯基}丙-2-醇、(15.042)2-{2-氟-6-[(8-氟-2-甲基喹啉-3-基)氧基]苯基}丙-2-醇、(15.043)2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯、(15.044)2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}苯基甲磺酸酯、(15.045)2-苯基苯酚及其盐、(15.046)3-(4,4,5-三氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、(15.047)3-(4,4-二氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、(15.048)4-氨基-5-氟嘧啶-2-醇(互变异构形式:4-氨基-5-氟嘧啶-2(1H)-酮)、(15.049)4-氧代-4-[(2-苯乙基)氨基]丁酸、(15.050)5-氨基-1,3,4-噻二唑-2-硫醇、(15.051)5-氯-N'-苯基-N'-(丙-2-炔-1-基)噻吩2-磺酰肼、(15.052)5-氟-2-[(4-氟苄基)氧基]嘧啶-4-胺、(15.053)5-氟-2-[(4-甲基苄基)氧基]嘧啶-4-胺、(15.054)9-氟-2,2-二甲基-5-(喹啉-3-基)-2,3-二氢-1,4-苯并氧杂吖庚因、(15.055)丁-3-炔-1-基{6-[({[(Z)-(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸酯、(15.056)(2Z)-3-氨基-2-氰基-3-苯基丙烯酸乙酯、(15.057)吩嗪-1-甲酸、(15.058)3,4,5-三羟基苯甲酸丙酯、(15.059)喹啉-8-醇、(15.060)喹啉-8-醇硫酸酯(2:1)、(15.061){6-[({[(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁酯、(15.062)5-氟-4-亚氨基-3-甲基-1-[(4-甲基苯基)磺酰基]-3,4-二氢嘧啶-2(1H)-酮。
作为混合组分的生物农药
可将式(I)的化合物与生物农药结合。
生物农药尤其包括细菌、真菌、酵母、植物提取物和由微生物形成的产物,包括蛋白质和次级代谢物。
生物农药包括细菌,如形成孢子的细菌、根部定殖细菌和用作生物杀昆虫剂、杀真菌剂或杀线虫剂的细菌。
用作或可用作生物农药的这类细菌的实例为:
解淀粉芽孢杆菌(Bacillus amyloliquefaciens),菌株FZB42(DSM 231179),或蜡样芽孢杆菌(Bacillus cereus),特别是蜡样芽孢杆菌菌株CNCM I-1562,或坚强芽孢杆菌,菌株I-1582(登记号CNCM I-1582),或短小芽孢杆菌(Bacillus pumilus),特别是菌株GB34(登记号ATCC 700814)和菌株QST2808(登记号NRRL B-30087),或枯草芽孢杆菌(Bacillussubtilis),特别是菌株GB03(登记号ATCC SD-1397),或枯草芽孢杆菌菌株QST713(登记号NRRL B-21661)或枯草芽孢杆菌菌株OST 30002(登记号NRRL B-50421),苏云金芽孢杆菌(Bacillus thuringiensis),特别是苏云金芽孢杆菌以色列亚种(血清型H-14),菌株AM65-52(登记号ATCC 1276),或苏云金芽孢杆菌鲇泽亚种,特别是菌株ABTS-1857(SD-1372),或苏云金芽孢杆菌库尔斯塔克亚种菌株HD-1,或苏云金芽孢杆菌拟步行甲亚种菌株NB 176(SD-5428),穿刺芽孢杆菌(Pasteuria penetrans),巴斯德氏芽菌属(Pasteuria spp.)(肾形线虫(Rotylenchulus reniformis nematode))-PR3(登记号ATCC SD-5834),细黄链霉菌(Streptomyces microflavus)菌株AQ6121(=QRD31.013,NRRL B-50550),鲜黄链霉菌(Streptomyces galbus)菌株AQ 6047(登记号NRRL 30232)。
用作或可用作生物农药的真菌和酵母的实例为:
球孢白僵菌(Beauveria bassiana),特别是菌株ATCC 74040,盾壳霉(Coniothyrium minitans),特别是菌株CON/M/91-8(登记号DSM-9660),蜡蚧菌属(Lecanicillium spp.),特别是菌株HRO LEC 12,蜡蚧轮枝菌(Lecanicillium lecanii)(先前称为蜡蚧轮枝孢(Verticillium lecanii)),特别是菌株KV01,绿僵菌(Metarhiziumanisopliae),特别是菌株F52(DSM3884/ATCC 90448),核果梅奇酵母(Metschnikowiafructicola),特别是菌株NRRL Y-30752,玫烟色拟青霉(Paecilomyces fumosoroseus)(新名称:玫烟色棒束孢(Isaria fumosorosea)),特别是菌株IFPC 200613或菌株Apopka 97(登记号ATCC 20874),淡紫色拟青霉(Paecilomyces lilacinus),特别是淡紫色拟青霉菌株251(AGAL 89/030550),黄色蠕形霉(Talaromyces flavus),特别是菌株V117b,深绿木霉(Trichoderma atroviride),特别是菌株SC1(登记号CBS 122089),哈茨木霉(Trichodermaharzianum),特别是哈茨木霉(T.harzianum rifai)T39(登记号CNCM I-952)。
用作或可用作生物农药的病毒的实例为:
棉褐带卷蛾(Adoxophyes orana)(夏季水果卷叶蛾(summer fruit tortrix))颗粒体病毒(GV)、苹果蠹蛾(Cydia pomonella)(codling moth)颗粒体病毒(GV)、棉铃虫(Helicoverpa armigera)(cotton bollworm)核多角体病毒(NPV)、甜菜夜蛾(Spodopteraexigua)(beet armyworm)mNPV、草地贪夜蛾(Spodoptera frugiperda)(fall armyworm)mNPV、海灰翅夜蛾(Spodoptera littoralis)(非洲棉叶虫(African cotton leafworm))NPV。
还包括作为“接种物”添加到植物或植物部位或植物器官并通过其特定性能促进植物生长和植物健康的细菌和真菌。实例包括:
土壤杆菌属(Agrobacterium spp.),茎瘤固氮根瘤菌(Azorhizobiumcaulinodans),固氮螺菌属(Azospirillum spp.),固氮菌属(Azotobacter spp.),慢生根瘤菌属(Bradyrhizobium spp.),伯克霍尔德菌属(Burkholderia spp.),特别是洋葱伯克霍尔德菌(Burkholderia cepacia)(先前称为洋葱假单胞菌(Pseudomonas cepacia)),巨孢囊霉属(Gigaspora spp.)或Gigaspora monosporum,球囊霉属(Glomus spp.),蜡蘑属(Laccaria spp.),布氏乳杆菌(Lactobacillus buchneri),类球囊霉属(Paraglomusspp.),Pisolithus tinctorus,假单胞菌属(Pseudomonas spp.),根瘤菌属(Rhizobiumspp.),特别是三叶草根瘤菌(Rhizobium trifolii),须腹菌属(Rhizopogon spp.),硬皮马勃属(Scleroderma spp.),乳牛肝菌属(Suillus spp.),链霉菌属(Streptomyces spp.)。
用作或可用作生物农药的植物提取物和由微生物形成的产物(包括蛋白质和次级代谢物)的实例为:
大蒜(Allium sativum)、苦艾(Artemisia absinthium)、印楝素(azadirachtin)、Biokeeper WP、Cassia nigricans、苦皮藤(Celastrus angulatus)、Chenopodiumanthelminticum、几丁质、Armour-Zen、欧洲鳞毛蕨(Dryopteris filix-mas)、问荆(Equisetum arvense)、Fortune Aza、Fungastop、Heads Up(藜麦皂苷提取物(Chenopodiumquinoa saponin extract))、除虫菊(pyrethrum)/除虫菊酯(pyrethrins)、苏里南苦木(Quassia amara)、栎(Quercus)、皂树(Quillaja)、Regalia、“RequiemTM杀昆虫剂”、鱼藤酮(rotenone)、鱼尼丁(ryania)/兰尼碱(ryanodine)、聚合草(Symphytum officinale)、菊蒿(Tanacetum vulgare)、百里酚(thymol)、Triact 70、TriCon、Tropaeulum majus、大荨麻(Urtica dioica)、藜芦碱(Veratrin)、白槲寄生(Viscum album)、十字花科(Brassicaceae)提取物(尤其是油菜粉或芥茉粉)。
作为混合组分的安全剂
可将式(I)的化合物与安全剂结合,所述安全剂例如解草嗪(benoxacor)、解毒喹(cloquintocet(-mexyl))、解草胺腈(cyometrinil)、环丙磺酰胺(cyprosulfamide)、二氯丙烯胺(dichlormid)、解草唑(fenchlorazole(-ethyl))、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草噁唑(furilazole)、双苯噁唑酸(isoxadifen(-ethyl))、吡唑解草酯(mefenpyr(-diethyl))、萘二甲酸酐(naphthalic anhydride)、解草腈(oxabetrinil)、2-甲氧基-N-({4-[(甲基氨基甲酰基)氨基]苯基}磺酰基)苯甲酰胺(CAS129531-12-0)、4-(二氯乙酰基)-1-氧杂-4-氮杂螺[4.5]癸烷(CAS 71526-07-3)、2,2,5-三甲基-3-(二氯乙酰基)-1,3-噁唑烷(CAS 52836-31-4)。
植物和植物部位
可根据本发明处理所有的植物和植物部位。在本文中,植物应理解为意指所有的植物和植物种群,例如需要和不需要的野生植物或作物植物(包括天然存在的作物植物),例如谷类(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、甜菜、甘蔗、番茄、甜椒、黄瓜、甜瓜、胡萝卜、西瓜、洋葱、莴苣、菠菜、韭菜、菜豆、甘蓝(Brassica oleracea)(例如卷心菜)和其他蔬菜种类、棉花、烟草、油菜以及水果植物(果实为苹果、梨、柑橘类果实和葡萄)。作物植物可为可通过常规育种和优化方法或通过生物技术和基因工程方法或这些方法的组合而获得的植物,包括转基因植物且包括可受或不受植物育种者权利保护的植物栽培种。植物应理解为意指所有的发育阶段,如种子、幼苗、幼小(未成熟的)植物直至并包括成熟植物。植物部位应理解为意指植物的地上和地下所有的部位和器官,如芽、叶、花和根,给出的实例为叶、针叶、茎、枝、花、子实体、果实和种子,以及根、块茎和根茎。植物部位还包括采收的植物或采收的植物部位以及无性繁殖和有性繁殖材料,例如插条、块茎、根茎、幼枝(slip)和种子。
本发明的使用式(I)的化合物对植物和植物部位的处理通过常规处理方法直接进行或使所述化合物作用于其环境、生境或贮存空间来进行,所述常规处理方法为例如浸渍、喷雾、蒸发、弥雾(fogging)、散布(scattering)、涂抹、注射,并且对于繁殖材料、尤其是对于种子,还通过施加一层或多层包衣来进行。
如上所述,可根据本发明处理所有的植物及其部位。在一个优选的实施方案中,处理野生植物品种和植物栽培种或通过常规生物育种方法如杂交或原生质体融合而获得的那些植物及其部位。在另一个优选的实施方案中,处理通过基因工程方法——如果合适与常规方法结合——获得的转基因植物和植物栽培种(遗传修饰生物体)及其部位。术语“部位”或“植物的部位”或“植物部位”已在上文进行了解释。根据本发明,特别优选处理各市售的常规植物栽培种的植物或在使用中的那些植物。植物栽培种应理解为意指具有新的特性(“性状”)且通过常规育种、诱变或重组DNA技术获得的植物。它们可为栽培种、变种、生物型或基因型。
转基因植物、种子处理和整合株系(integration event)
待根据本发明处理的优选的转基因植物或植物栽培种(通过基因工程获得的那些植物)包括通过遗传修饰而接受了遗传物质的所有植物,所述遗传物质赋予这些植物特别有利的、有用的特性(“性状”)。此类特性的实例为更好的植物生长、提高的对高温或低温的耐受性、提高的对干旱或者对水或土壤盐渍度水平的耐受性、增强的开花性能、更容易的采收、加速的成熟、更高的采收产量、采收产品的更高的品质和/或更高的营养价值、采收产品的更好的保存能力和/或加工性能。这类特性的其他且特别强调的实例为:由于例如在植物内形成的毒素、特别是通过来自苏云金芽孢杆菌的遗传物质(例如通过基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF及其组合)在植物内形成的那些毒素而使植物对动物害虫和微生物害虫如昆虫、蛛形纲动物、线虫、螨、蛞蝓和蜗牛的抗性增强,以及由例如系统获得性抗性(SAR)、系统素、植物抗毒素、诱导子(elicitor)和抗性基因以及相应表达的蛋白质和毒素引起植物对植物病原性真菌、细菌和/或病毒的抗性增强,以及植物对某些除草活性化合物例如咪唑啉酮类、磺酰脲类、草甘膦或草丁膦(phosphinothricin)的耐受性提高(例如“PTA”基因)。赋予所述期望特性(“性状”)的基因还可彼此结合地存在于转基因植物中。提及的转基因植物的实例包括重要的作物植物,如谷类(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、甜菜、甘蔗、番茄、豌豆和其他蔬菜品种、棉花、烟草、油菜以及水果植物(果实为苹果、梨、柑橘类果实和葡萄),特别强调玉米、大豆、小麦、稻、马铃薯、棉花、甘蔗、烟草和油菜。特别强调的特性(“性状”)为植物对昆虫、蛛形纲动物、线虫以及蛞蝓和蜗牛的抗性增强。
作物保护——处理的类型
使用常规处理方法用式(I)的化合物对植物和植物部位进行直接处理,或通过作用于其环境、生境或贮存空间进行处理,所述常规处理方法例如浸渍、喷雾、雾化、灌溉、蒸发、撒粉、弥雾、撒播、发泡、涂布、铺展(spreading-on)、注射、浇水(浸透)、滴灌,并且对于繁殖材料、特别是对于种子,所述常规处理方法还有干种子处理、液体种子处理、浆料处理,包壳,用一层或多层包衣包覆等。还可通过超低容量法施用式(I)的化合物或将施用形式或式(I)的化合物本身注入土壤中。
一种优选的对植物的直接处理为叶面施用,意指将式(I)的化合物施用于叶面,在这种情况下,应根据所述害虫的侵染水平来调节处理频率和施用率。
对于内吸性活性成分,式(I)的化合物还通过根系进入植物。然后通过将式(I)的化合物作用于植物的生境来处理植物。这可例如通过浸透或通过混入土壤或营养液中来完成,意指用式(I)的化合物的液体形式浸渍植物的位置(例如土壤或水培体系),或通过土壤施用来完成,意指将本发明的式(I)的化合物以固体形式(例如以颗粒剂的形式)引入植物的位置中,或通过滴灌施用(通常也称为“化学灌溉”),意指在特定的时间段内在植物位置中的指定位点通过地面滴管或地下滴管将本发明式(I)的化合物与不同量的水一起引入。对于水稻作物,这还可通过将固体施用形式(例如以颗粒剂的形式)的式(I)的化合物计量加入水稻田中来完成。
种子处理
通过对植物的种子进行处理来防治动物害虫早已为人所知,并且是不断改进的主题。然而,对种子的处理引起了一系列始终不能以令人满意的方式解决的问题。因此,期望开发保护种子和发芽植物的方法,所述方法在贮存期间、在播种后或在植物出苗后无需或至少显著降低额外的农药施用。此外,期望优化使用的活性成分的量,从而为种子和发芽植物提供最佳保护,使其免受动物害虫侵袭,而使用的活性成分不会损害植物本身。特别地,用于种子处理的方法还应考虑抵抗或耐受害虫的转基因植物所固有的杀昆虫特性或杀线虫特性,以使用最少量的农药实现对种子以及发芽植物的最佳保护。
因此,本发明还特别涉及一种通过用式(I)的化合物之一处理种子来保护种子和发芽植物免受害虫侵袭的方法。本发明的保护种子和发芽植物免受害虫侵袭的方法还包括这样的方法,其中用式(I)的化合物和混合组分在一次操作中同时对种子进行处理或依序对种子进行处理。其另外还包括这样的方法,其中用式(I)的化合物和混合组分在不同的时间对种子进行处理。
本发明还涉及式(I)的化合物用于处理种子以保护种子和所得植物免受动物害虫侵袭的用途。
本发明还涉及已用本发明的式(I)的化合物进行处理以保护其免受动物害虫侵袭的种子。本发明还涉及已用式(I)的化合物和混合组分同时进行处理的种子。本发明还涉及已用式(I)的化合物和混合组分在不同时间进行处理的种子。对于已用式(I)的化合物和混合组分在不同时间进行处理的种子,各物质可以以不同的层存在于种子上。在这种情况下,包含式(I)的化合物和混合组分的层可任选地通过中间层隔开。本发明还涉及这样的种子:其中将式(I)的化合物和混合组分作为包衣的一部分或作为除包衣之外的另一层或另几层进行施用。
本发明还涉及这样的种子:在用式(I)的化合物处理后,对其进行薄膜包衣处理以避免种子受灰尘磨损。
在式(I)的化合物内吸性地起作用时,产生的优点之一在于对种子进行处理不仅保护种子本身,还保护由其产生的植物在出苗后免受动物害虫的侵袭。以这种方式,可免除在播种时或播种后不久对作物进行即时处理。
另一个优点在于,用式(I)的化合物对种子进行处理可增强被处理的种子的发芽和出苗。
同样认为有利的是,式(I)的化合物还可特别地用于转基因种子。
此外,式(I)的化合物可与信号技术组合物结合使用,使得通过共生体(例如根瘤菌、菌根和/或植物内生细菌或真菌)而更好地定殖,和/或优化固氮作用。
式(I)的化合物适于保护在农业、温室、林业或园艺中使用的任何植物品种的种子。更具体而言,所述种子为谷类(例如小麦、大麦、黑麦、粟和燕麦)、玉米、棉花、大豆、稻、马铃薯、向日葵、咖啡、烟草、加拿大油菜(canola)、油菜、甜菜(例如糖用甜菜和饲用甜菜)、花生、蔬菜类(例如番茄、黄瓜、菜豆、十字花科蔬菜、洋葱和莴苣)、水果植物、草坪植物和观赏植物的种子。特别有意义的是处理谷类(例如小麦、大麦、黑麦和燕麦)、玉米、大豆、棉花、加拿大油菜、油菜、蔬菜类和稻的种子。
如上所述,用式(I)的化合物对转基因种子进行处理也是特别重要的。这涉及通常含有至少一种异源基因的植物的种子,所述异源基因控制特别是具有杀昆虫和/或杀线虫特性的多肽的表达。转基因种子中的异源基因可来源于微生物如芽孢杆菌属(Bacillus)、根瘤菌属(Rhizobium)、假单胞菌属(Pseudomonas)、沙雷氏菌属(Serratia)、木霉属(Trichoderma)、棒形杆菌属(Clavibacter)、球囊霉属(Glomus)或粘帚霉属(Gliocladium)。本发明特别适于处理包含至少一种来源于芽孢杆菌属的异源基因的转基因种子。异源基因更优选来源于苏云金芽孢杆菌。
在本发明的上下文中,将式(I)的化合物施用至种子。优选地,在种子足够稳定以在处理过程中不发生损害的状态下处理种子。通常,可在采收和播种之间的任意时间处理种子。通常使用已从植物中分离并且已经除去穗轴、外壳、茎、表皮、绒毛或果肉的种子。例如,可使用已经采收、清洁并且干燥至允许存储的含水量的种子。或者,还可使用干燥后已用例如水进行处理然后再干燥(例如灌注(priming))的种子。对于稻的种子,还可使用已在例如水中浸泡直至其到达稻胚(“胚乳期(pigeon breast stage)”)的某一阶段的种子,这可刺激发芽并使出苗更均匀。
在处理种子时,通常必须注意对施用至种子的式(I)的化合物的量和/或其他添加剂的量进行选择,使得种子的发芽不受到不利影响,或所得植物不受到损害。对于在某些施用率下可以表现出植物毒性效应的活性成分,必须特别确保这一点。
通常,将式(I)的化合物以合适的制剂形式施用至种子。用于种子处理的合适的制剂和方法是本领域技术人员已知的。
可将式(I)的化合物转化为常规的拌种制剂,如溶液剂、乳剂、悬浮剂、粉剂、泡沫剂、浆剂或其他种子包衣组合物,以及ULV制剂。
这些制剂以已知方式通过将式(I)的化合物与常规添加剂混合而制备,所述常规添加剂为例如常规增量剂和溶剂或稀释剂、染料、润湿剂、分散剂、乳化剂、消泡剂、防腐剂、二次增稠剂、胶粘剂、赤霉素以及水。
可存在于可根据本发明使用的拌种制剂中的染料为通常用于此类目的的所有染料。可使用微溶于水的颜料或溶于水的染料。实例包括已知的名称为罗丹明B、C.I.颜料红112和C.I.溶剂红1的染料。
可存在于可根据本发明使用的拌种制剂中的有用的润湿剂为促进润湿并且通常用于农业化学活性成分的制剂的所有物质。可优选使用萘磺酸烷基酯,如萘磺酸二异丙酯或萘磺酸二异丁酯。
可存在于可根据本发明使用的拌种制剂中的合适的分散剂和/或乳化剂为通常用于农业化学活性成分的制剂的所有非离子、阴离子和阳离子分散剂。可优选使用非离子或阴离子分散剂或非离子或阴离子分散剂的混合物。合适的非离子分散剂特别包括环氧乙烷/环氧丙烷嵌段聚合物、烷基酚聚乙二醇醚和三苯乙烯基苯酚聚乙二醇醚,及其磷酸化或硫酸化衍生物。合适的阴离子分散剂特别是木素磺酸盐、聚丙烯酸盐和芳基磺酸酯-甲醛缩合物。
可存在于可根据本发明使用的拌种制剂中的消泡剂为通常用于农业化学活性成分的制剂的所有抑制泡沫的物质。可优选使用有机硅(silicone)消泡剂和硬脂酸镁。
可存在于可根据本发明使用的拌种制剂中的防腐剂为可在农业化学组合物中用于此类目的的所有物质。实例包括双氯酚和苄醇半缩甲醛。
可存在于可根据本发明使用的拌种制剂中的二次增稠剂为可在农业化学组合物中用于此类目的的所有物质。优选的实例包括纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土以及细分散的二氧化硅。
可存在于可根据本发明使用的拌种制剂中的有用的粘着剂为可用于拌种产品中的所有常规粘合剂。优选的实例包括聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和甲基纤维素(tylose)。
可存在于可根据本发明使用的拌种制剂中的赤霉素优选为赤霉素A1、A3(=赤霉酸)、A4和A7;特别优选使用赤霉酸。赤霉素是已知的(参见R.Wegler"Chemie derPflanzenschutz-and ",第2卷,Springer Verlag,1970,第401-412页)。
可根据本发明使用的拌种制剂可直接或预先用水稀释后用于处理多种不同种类的种子。例如,浓缩剂或可通过用水稀释而由其获得的制剂可用于对以下种子进行拌种:谷类(如小麦、大麦、黑麦、燕麦和黑小麦)的种子以及玉米、稻、油菜、豌豆、菜豆、棉花、向日葵、大豆和甜菜的种子,或多种不同的蔬菜种子。可根据本发明使用的拌种制剂或其稀释的使用形式还可用于对转基因植物的种子进行拌种。
为了使用可根据本发明使用的拌种制剂或通过添加水而由其制得的使用形式处理种子,通常可用于拌种的所有混合单元都是有用的。具体而言,拌种的步骤为:以分批或连续操作的方式将种子置入混合器中;加入特定所需量的拌种制剂(以其本身或预先用水稀释后);以及进行混合直至制剂均匀地分布在种子上。如果合适,随后进行干燥操作。
可根据本发明使用的拌种制剂的施用率可在相对宽的范围内变化。这取决于制剂中式(I)的化合物的具体含量以及种子。式(I)的化合物的施用率通常为每千克种子0.001至50g,优选为每千克种子0.01至15g。
动物健康
在动物健康领域,即兽医学领域,式(I)的化合物对动物寄生虫、特别是体外寄生虫或体内寄生虫具有活性。术语“体内寄生虫”特别包括蠕虫和原生动物,如球虫目(coccidia)。体外寄生虫通常且优选为节肢动物,特别是昆虫或螨类。
在兽医学领域,具有有利的恒温动物毒性的式(I)的化合物适于防治在家畜、育种动物、动物园动物、实验室动物、实验动物和家养动物的动物育种和动物饲养中出现的寄生虫。它们对寄生虫的所有或特定发育阶段均具有活性。
农业家畜包括例如哺乳动物,如绵羊、山羊、马、驴、骆驼、水牛、兔、驯鹿、扁角鹿,以及特别是牛和猪;或家禽如火鸡、鸭、鹅,以及特别是鸡;或例如水产养殖中的鱼或甲壳类动物;或——根据情况——为昆虫如蜜蜂。
家养动物包括例如哺乳动物,如仓鼠、豚鼠、大鼠、小鼠、毛丝鼠、雪貂,以及特别是狗、猫、笼养鸟;爬行动物、两栖动物或观赏鱼。
在一个具体的实施方案中,将式(I)的化合物给予哺乳动物。
在另一个具体的实施方案中,将式(I)的化合物给予鸟类,即笼养鸟或特别是家禽。
使用式(I)的化合物来防治动物寄生虫旨在减少或预防疾病、死亡病例和性能降低(对于肉、奶、羊毛、皮、蛋、蜂蜜等),使得动物饲养更经济和更简单,并可实现更好的动物健康。
关于动物健康领域,在本发明的上下文中,术语“防治(control)”或“防治(controlling)”意指式(I)的化合物可有效地将特定寄生虫在感染此类寄生虫的动物中的发病率降低至无害的程度。更具体而言,在本发明的上下文中,“防治”意指式(I)的化合物可杀死各寄生虫、抑制其生长或抑制其繁殖。
节肢动物包括但不限于,例如,
来自虱目(Anoplurida)的节肢动物,例如血虱属(Haematopinus spp.)、毛虱属(Linognathus spp.)、虱属(Pediculus spp.)、阴虱属(Phtirus spp.)和管虱属(Solenopotes spp.);
来自食毛目(Mallophagida)以及钝角亚目(Amblycerina)和细角亚目(Ischnocerina)的节肢动物,例如牛羽虱属(Bovicola spp.)、Damalina属、猫羽虱属(Felicola spp.);Lepikentron属、禽虱属(Menopon spp.)、啮毛虱属(Trichodectesspp.)、毛羽虱属(Trimenopon spp.)、巨羽虱属(Trinoton spp.)、Werneckiella属;
来自双翅目(Diptera)以及长角亚目(Nematocerina)和短角亚目(Brachycerina)的节肢动物,例如伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、黄虻属(Atylotusspp.)、蜂虱蝇属(Braula spp.)、丽蝇属(Calliphora spp.)、金蝇属(Chrysomyia spp.)、斑虻属(Chrysops spp.)、库蚊属(Culex spp.)、库蠓属(Culicoides spp.)、真蚋属(Eusimulium spp.)、厕蝇属(Fannia spp.)、胃蝇属(Gasterophilus spp.)、舌蝇属(Glossina spp.)、角蝇属(Haematobia spp.)、麻虻属(Haematopota spp.)、虱蝇属(Hippobosca spp.)、瘤虻属(Hybomitra spp.)、齿股蝇属(Hydrotaea spp.)、皮蝇属(Hypoderma spp.)、羊虱蝇属(Lipoptena spp.)、绿蝇属(Lucilia spp.)、罗蛉属(Lutzomyia spp.)、蜱蝇属(Melophagus spp.)、莫蝇属(Morellia spp.)、家蝇属(Muscaspp.)、短蚋亚属(Odagmia spp.)、狂蝇属(Oestrus spp.)、Philipomyia属、白蛉属(Phlebotomus spp.)、鼻狂蝇属(Rhinoestrus spp.)、麻蝇属(Sarcophaga spp.)、蚋属(Simulium spp.)、螫蝇属(Stomoxys spp.)、虻属(Tabanus spp.)、大蚊属(Tipula spp.)、维蚋属(Wilhelmia spp.)、污蝇属(Wohlfahrtia spp.);
来自蚤目(Siphonapterida)的节肢动物,例如角叶蚤属(Ceratophyllus spp.)、栉首蚤属(Ctenocephalides spp.)、蚤属(Pulex spp.)、潜蚤属(Tunga spp.)、客蚤属(Xenopsylla spp.);
来自异翅目(heteropterida)的节肢动物,例如臭虫属(Cimex spp.)、锥蝽属(Panstrongylus spp.)、红猎蝽属(Rhodnius spp.)、锥猎蝽属(Triatoma spp.);以及来自蜚蠊目的讨厌的害虫和卫生害虫。
此外,对于节肢动物,示例性地而非限制性地提及以下蜱螨亚纲(Acari):
来自蜱螨亚纲(蜱螨目(Acarina))和后气门目(Metastigmata)的节肢动物,例如隐喙蜱科(Argasidae),如锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodorus spp.)、残缘蜱属(Otobius spp.),硬蜱科(Ixodidae),如花蜱属(Amblyomma spp.)、革蜱属(Dermacentorspp.)、血蜱属(Haemaphysalis spp.)、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、扇头蜱属(牛蜱属)(Rhipicephalus(Boophilus)spp.)、扇头蜱属(Rhipicephalus spp.)(多宿主蜱的原属);来自中气门目(Mesostigmata)的节肢动物,如皮刺螨属(Dermanyssusspp.)、禽刺螨属(Ornithonyssus spp.)、肺刺螨属(Pneumonyssus spp.)、刺利螨属(Raillietia spp.)、胸刺螨属(Sternostoma spp.)、热厉螨属(Tropilaelaps spp.)、瓦螨属(Varroa spp.);来自辐螨目(Actinedida)(前气门目(Prostigmata))的节肢动物,例如蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、蠕形螨属(Demodex spp.)、Listrophorus属、肉螨属(Myobia spp.)、新恙螨属(Neotrombicula spp.)、禽螯螨属(Ornithocheyletia spp.)、疮螨属(Psorergates spp.)、恙螨属(Trombicula spp.);和来自粉螨目(Acaridida)(无气门目(Astigmata))的节肢动物,例如粉螨属(Acarus spp.)、嗜木螨属(Caloglyphus spp.)、足螨属(Chorioptes spp.)、胞螨属(Cytodites spp.)、颈下螨属(Hypodectes spp.)、疙螨属(Knemidocoptes spp.)、鸡雏螨属(Laminosioptesspp.)、背肛螨属(Notoedres spp.)、耳螨属(Otodectes spp.)、痒螨属(Psoroptes spp.)、翅螨属(Pterolichus spp.)、疥螨属(Sarcoptes spp.)、Trixacarus属、食酪螨属(Tyrophagus spp.)。
寄生原生动物的实例包括,但不限于:
鞭毛纲(Mastigophora)(鞭毛虫纲(Flagellata)),如:
后滴门(Metamonada):双滴虫目(Diplomonadida),例如贾第虫属(Giardiaspp.)、旋核鞭毛虫属(Spironucleus spp.)。
副基体纲(Parabasala):毛滴虫目(Trichomonadida),例如组织滴虫属(Histomonas spp.)、五毛滴虫属(Pentatrichomonas spp.)、四毛滴虫属(Tetratrichomonas spp.)、毛滴虫属(Trichomonas spp.)、三毛滴虫属(Tritrichomonasspp.)。
眼虫门(Euglenozoa):锥体虫目(Trypanosomatida),例如利什曼原虫属(Leishmania spp.)、锥体虫属(Trypanosoma spp.)。
肉足鞭毛亚门(Sarcomastigophora)(根足亚纲(Rhizopoda))如内阿米巴科(Entamoebidae),例如内变形虫属(Entamoeba spp.),Centramoebidae,例如棘阿米巴属(Acanthamoeba sp.),Euamoebidae,例如哈氏虫属(Hartmanella sp.)。
囊泡虫类(Alveolata)如顶复亚门(Apicomplexa)(孢子虫类(Sporozoa)):例如隐孢子虫属(Cryptosporidium spp.);艾美目(Eimeriida),例如贝诺孢子虫属(Besnoitiaspp.)、囊等孢球虫属(Cystoisospora spp.)、艾美球虫属(Eimeria spp.)、哈蒙属(Hammondia spp.)、等孢子球虫属(Isospora spp.)、新孢子虫属(Neospora spp.)、肉孢子虫属(Sarcocystis spp.)、弓形虫属(Toxoplasma spp.);Adeleida,例如肝簇虫属(Hepatozoon spp.)、克洛西埃拉属(Klossiella spp.);血孢子虫目(Haemosporida),例如住白虫属(Leucocytozoon spp.)、疟原虫属(Plasmodium spp.);梨形虫目(Piroplasmida),例如巴倍虫属(Babesia spp.)、纤毛虫属(Ciliophora spp.)、Echinozoon属、泰勒虫属(Theileria spp.);Vesibuliferida,例如肠袋虫属(Balantidiumspp.)、Buxtonella属。
微孢子门(Microspora)如脑胞内原虫属(Encephalitozoon spp.)、肠孢子虫属(Enterocytozoon spp.)、球虫属(Globidium spp.)、小孢子虫属(Nosema spp.),以及例如Myxozoa属。
对人类或动物致病的蠕虫,包括例如棘头动物门(Acanthocephala)、线虫类(nematodes)、舌形动物门(Pentastoma)和扁形动物门(Platyhelminthes)(例如单殖亚纲(Monogenea)、绦虫类(cestodes)和吸虫类(trematodes))。
示例性蠕虫包括,但不限于:
单殖亚纲(Monogenea):例如,指环虫属(Dactylogyrus spp.)、三代虫属(Gyrodactylus spp.)、Microbothrium属、多盘虫属(Polystoma spp.)、Troglecephalus属;
多节绦虫类:假叶目(Pseudophyllidea),例如,吸叶绦虫属(Bothridium spp.)、裂头绦虫属(Diphyllobothrium spp.)、大复殖孔绦虫属(Diplogonoporus spp.)、Ichthyobothrium属、舌状绦虫属(Ligula spp.)、裂头绦虫属(Schistocephalus spp.)、迭宫绦虫属(Spirometra spp.);
圆叶目(cyclophyllida),例如:Andyra属、裸头绦虫属(Anoplocephala spp.)、无卵黄腺属(Avitellina spp.)、伯特绦虫属(Bertiella spp.)、鸣绦虫属(Cittotaeniaspp.)、戴文氏绦虫属(Davainea spp.)、双睾绦虫属(Diorchis spp.)、Diplopylidium属、复孔绦虫属(Dipylidium spp.)、棘球属(Echinococcus spp.)、Echinocotyle属、棘鳞绦虫属(Echinolepis spp.)、泡尾绦虫属(Hydatigera spp.)、膜壳绦虫属(Hymenolepisspp.)、乔伊属(Joyeuxiella spp.)、中殖孔绦虫属(Mesocestoides spp.)、莫尼茨绦虫属(Moniezia spp.)、副裸头属(Paranoplocephala spp.)、瑞列绦虫属(Raillietina spp.)、斯泰勒绦虫属(Stilesia spp.)、带绦虫属(Taenia spp.)、曲子宫绦虫属(Thysanieziaspp.)、遂体绦虫属(Thysanosoma spp.)。
吸虫类:复殖纲(Digenea),例如,澳毕吸虫属(Austrobilharzia spp.)、短咽属(Brachylaima spp.)、杯殖属(Calicophoron spp.)、下弯属(Catatropis spp.)、支睾属(Clonorchis spp.)、肛瘤吸虫属(Collyriclum spp.)、殖盘属(Cotylophoron spp.)、环腔属(Cyclocoelum spp.)、双腔属(Dicrocoelium spp.)、双穴吸虫属(Diplostomum spp.)、棘隙属(Echinochasmus spp.)、棘缘属(Echinoparyphium spp.)、棘口属(Echinostomaspp.)、阔盘属(Eurytrema spp.)、片吸虫属(Fasciola spp.)、Fasciolides属、姜片虫属(Fasciolopsis spp.)、菲策属(Fischoederius spp.)、腹袋吸虫属(Gastrothylacusspp.)、巨毕吸虫属(Gigantobilharzia spp.)、巨盘属(Gigantocotyle spp.)、异形吸虫属(Heterophyes spp.)、低颈属(Hypoderaeum spp.)、彩蚴吸虫属(Leucochloridium spp.)、后殖吸虫属(Metagonimus spp.)、次睾属(Metorchis spp.)、侏形吸虫属(Nanophyetusspp.)、背孔属(Notocotylus spp.)、后睾吸虫属(Opisthorchis spp.)、东毕血吸虫属(Ornithobilharzia spp.)、并殖吸虫属(Paragonimus spp.)、同盘属(Paramphistomumspp.)、斜睾吸虫属(Plagiorchis spp.)、茎双穴吸虫属(Posthodiplostomum spp.)、前殖属(Prosthogonimus spp.)、血吸虫属(Schistosoma spp.)、毛血吸虫属(Trichobilharziaspp.)、隐孔吸虫属(Troglotrema spp.)、盲腔属(Typhlocoelum spp.)。
线虫类:毛形目(Trichinellida),例如,毛细线虫属(Capillaria spp.)、毛线虫属(Trichinella spp.)、Trichomosoides属、鞭虫属(Trichuris spp.);
垫刃目(Tylenchida),例如:细丝鲶属(Micronema spp.)、Parastrangyloides属、类圆线虫属(Strongyloides spp.);
杆形目(Rhabditina),例如,猫圆线虫属(Aelurostrongylus spp.)、裂口线虫属(Amidostomum spp.)、钩虫属(Ancylostoma spp.)、管圆线虫属(Angiostrongylus spp.)、Bronchonema属、仰口线虫属(Bunostomum spp.)、夏柏特线虫属(Chabertia spp.)、古柏线虫属(Cooperia spp.)、Cooperioides属、环体线虫属(Crenosoma spp.)、盅口属(Cyathostomum spp.)、Cyclococercus属、Cyclodontostomum属、杯环属(Cylicocyclusspp.)、杯冠属(Cylicostephanus spp.)、柱咽属(Cylindropharynx spp.)、囊尾线虫属(Cystocaulus spp.)、网尾线虫属(Dictyocaulus spp.)、麂圆线虫属(Elaphostrongylusspp.)、类丝虫属(Filaroides spp.)、球首属(Globocephalus spp.)、Graphidium属、辐首属(Gyalocephalus spp.)、血矛线虫属(Haemonchus spp.)、Heligmosomoides属、猪圆属(Hyostrongylus spp.)、马歇尔属(Marshallagia spp.)、后圆线虫属(Metastrongylusspp.)、缪勒线虫属(Muellerius spp.)、板口线虫属(Necator spp.)、细颈线虫属(Nematodirus spp.)、新圆线虫属(Neostrongylus spp.)、日圆线虫属(Nippostrongylusspp.)、尖柱属(Obeliscoides spp.)、食道齿属(Oesophagodontus spp.)、结节线虫属(Oesophagostomum spp.)、盘头线虫属(Ollulanus spp.);鸟圆属(Ornithostrongylusspp.)、奥斯勒属(Oslerus spp.)、胃线虫属(Ostertagia spp.)、副古柏线虫属(Paracooperia spp.)、Paracrenosoma属、类副丝虫属(Parafilaroides spp.)、副鹿圆线虫属(Parelaphostrongylus spp.)、Pneumocaulus属、肺圆线虫属(Pneumostrongylusspp.)、盂口属(Poteriostomum spp.)、原圆线虫属(Protostrongylus spp.)、锐尾线虫属(Spicocaulus spp.)、冠尾属(Stephanurus spp.)、圆线虫属(Strongylus spp.)、比翼属(Syngamus spp.)、背带线虫属(Teladorsagia spp.)、毛线属(Trichonema spp.)、毛圆线虫属(Trichostrongylus spp.)、三齿属(Triodontophorus spp.)、Troglostrongylus属、钩虫属(Uncinaria spp.);
旋尾目(Spirurida),例如,棘唇线虫属(Acanthocheilonema spp.)、异尖属(Anisakis spp.)、鸡蛔虫属(Ascaridia spp.);蛔虫属(Ascaris spp.)、似蛔属(Ascaropsspp.)、无刺属(Aspiculuris spp.)、贝蛔属(Baylisascaris spp.)、布鲁线虫属(Brugiaspp.)、Cercopithifilaria属、Crassicauda属、双瓣线虫属(Dipetalonema spp.)、恶丝虫属(Dirofilaria spp.)、龙线虫属(Dracunculus spp.);Draschia属、蛲虫属(Enterobiusspp.)、丝虫属(Filaria spp.)、颚口线虫属(Gnathostoma spp.)、筒线虫属(Gongylonemaspp.)、丽线虫属(Habronema spp.)、异刺线虫属(Heterakis spp.);类平滑丝虫属(Litomosoides spp.)、罗阿丝虫属(Loa spp.)、盘尾丝虫属(Onchocerca spp.)、尖尾线虫属(Oxyuris spp.)、副柔线虫属(Parabronema spp.)、副丝虫属(Parafilaria spp.)、副蛔虫属(Parascaris spp.)、栓尾线虫属(Passalurus spp.)、泡翼属(Physaloptera spp.)、Probstmayria属、Pseudofilaria属、腹腔丝虫属(Setaria spp.)、Skjrabinema属、旋尾线虫属(Spirocerca spp.)、冠丝虫属(Stephanofilaria spp.)、Strongyluris属、管状线虫属(Syphacia spp.)、吸吮线虫属(Thelazia spp.)、弓蛔线虫属(Toxascaris spp.)、弓蛔虫属(Toxocara spp.)、吴策线虫属(Wuchereria spp.)。
棘头动物门(Acanthocephala):少棘目(Oligacanthorhynchida),例如,巨吻棘头虫属(Macracanthorhynchus spp.)、前睾属(Prosthenorchis spp.);念珠目(Moniliformida),例如,念珠棘虫属(Moniliformis spp.)。
多形目(Polymorphida),例如:细颈属(Filicollis spp.);棘吻目(Echinorhynchida),例如棘头花属(Acanthocephalus spp.)、棘吻虫属(Echinorhynchusspp.)、似细吻棘头虫属(Leptorhynchoides spp.)。
舌形动物门(Pentastoma):蛇舌状虫目(Porocephalida),例如,舌形虫属(Linguatula spp.)。
在兽医领域中和动物饲养中,通过本领域通常已知的方法如经肠内、肠外、真皮或鼻的途径以合适的制剂形式给予式(I)的化合物。给予可为预防性的、后期预防性的(metaphylactic)或治疗性的。
因此,本发明的一个实施方案涉及将式(I)的化合物用作药物。
另一个方面涉及将式(I)的化合物用作抗体内寄生虫剂(antiendoparasiticagent)。
本发明的另一个具体方面涉及将式(I)的化合物用作抗蠕虫剂(antithelminthicagent),特别是用作杀线虫剂、杀扁形动物剂(platyhelminthicide)、杀棘头虫剂(acanthocephalicide)或杀舌形动物剂(pentastomicide)。
本发明的另一个具体方面涉及将式(I)的化合物用作抗原生动物剂(antiprotozoic agent)。
另一个方面涉及将式(I)的化合物用作抗体外寄生虫剂(antiectoparasiticagent),尤其是杀节肢动物剂(arthropodicide),非常特别地是杀昆虫剂或杀螨剂。
本发明的其他方面为兽医制剂,其包含有效量的至少一种式(I)的化合物和至少一种下列物质:药学上可接受的赋形剂(例如固体或液体稀释剂)、药学上可接受的助剂(例如表面活性剂),特别是通常在兽医制剂中使用的药学上可接受的赋形剂和/或通常在兽医制剂中使用的药学上可接受的助剂。
本发明的一个相关方面为一种制备如本文中所述的兽医制剂的方法,其包括以下步骤:将至少一种式(I)的化合物与药学上可接受的赋形剂和/或助剂混合,特别是与通常在兽医制剂中使用的药学上可接受的赋形剂和/或通常在兽医制剂中使用的助剂混合。
本发明的另一个具体方面为兽医制剂及其制备方法,所述兽医制剂选自所提及方面的杀体外寄生虫制剂(ectoparasiticidal formulation)和杀体内寄生虫制剂(endoparasiticidal formulation),尤其是选自抗蠕虫制剂、抗原生动物制剂和杀节肢动物制剂,非常特别地选自杀线虫制剂、杀扁形动物(platyhelminthicidal)制剂、杀棘头虫(acanthocephalicidal)制剂、杀舌形动物(pentastomicidal)制剂、杀昆虫制剂和杀螨制剂。
另一个方面涉及一种通过在有需要的动物、尤其是非人类动物中使用有效量的式(I)的化合物来治疗寄生感染、尤其是由选自本文中提及的体外寄生虫和体内寄生虫的寄生虫所引起的感染的方法。
另一个方面涉及一种通过在有需要的动物、尤其是非人类动物中使用如本文中所定义的兽医制剂来治疗寄生感染、尤其是由选自本文中提及的体外寄生虫和体内寄生虫的寄生虫所引起的感染的方法。
另一个方面涉及式(I)的化合物在动物、尤其是非人类动物中治疗寄生感染、尤其是由选自本文中提及的体外寄生虫和体内寄生虫的寄生虫所引起的感染的用途。
在动物健康或兽医学的情况下,术语“治疗”包括预防性的、后期预防性的和治疗性的治疗。
在特定的实施方案中,以这种方法为兽医学领域提供至少一种式(I)的化合物与其他活性成分、尤其是与杀体内寄生虫剂和杀体外寄生虫剂的混合物。
在动物健康领域,“混合物”不仅意指将两种(或多种)不同的活性成分配制在共同的制剂中并相应地一起使用,而且还涉及包含各活性成分单独的制剂的产品。因此,当使用多于两种活性成分时,所有的活性成分可配制在共同的制剂中或所有的活性成分可配制在单独的制剂中;同样可为这样的混合形式:其中一些活性成分一起配制而一些活性化合物单独配制。单独的制剂使得所述活性成分可以单独施用或连续施用。
本文中以其“通用名称”指定的活性成分是已知的,并且记载于例如"PesticideManual"(参见上文)中或者可在因特网(例如:http://www.alanwood.net/pesticides)上检索。
作为混合组分的选自杀体外寄生虫剂的示例性活性成分包括——在没有任何应构成限制的意图的情况下——上文中详细列出的杀昆虫剂和杀螨剂。根据上述基于当前IRAC作用方式分类方案的分类,下文列出可使用的其他活性成分:(1)乙酰胆碱酯酶(AChE)抑制剂;(2)GABA门控氯化物通道阻断剂;(3)钠通道调节剂;(4)烟碱能乙酰胆碱受体(nAChR)竞争调节剂;(5)烟碱能乙酰胆碱受体(nAChR)变构调节剂;(6)谷氨酸酯门控氯化物通道(GluCl)变构调节剂;(7)保幼激素模拟物;(8)多种非特异性(多位点)抑制剂;(9)弦音器官调节剂;(10)螨生长抑制剂;(12)线粒体ATP合酶抑制剂,如ATP干扰剂;(13)通过间隔质子梯度作用的氧化磷酸化解偶联剂;(14)烟碱能乙酰胆碱受体通道阻断剂;(15)0型几丁质生物合成抑制剂;(16)1型几丁质生物合成抑制剂;(17)蜕皮干扰剂(尤其是在双翅目中);(18)蜕皮激素受体激动剂;(19)章鱼胺受体激动剂;(21)线粒体复合物I电子传递抑制剂;(25)线粒体复合物II电子传递抑制剂;(20)线粒体复合物III电子传递抑制剂;(22)电压依赖型钠通道阻断剂;(23)乙酰基辅酶A(CoA)羧化酶抑制剂;(28)兰尼碱受体调节剂;
具有未知的或不确定的作用机理的活性成分,例如氟硝二苯胺(fentrifanil)、氧嘧酰胺(fenoxacrim)、cycloprene、乙酯杀螨醇(chlorobenzilate)、杀虫脒(chlordimeform)、氟苯灭(flubenzimin)、环虫腈(dicyclanil)、磺胺螨酯(amidoflumet)、灭螨猛(quinomethionat)、苯螨噻(triarathene)、clothiazoben、杀螨好(tetrasul)、油酸钾、石油、噁虫酮(metoxadiazone)、gossyplur、氟螨嗪(flutenzine)、溴螨酯(brompropylate)、冰晶石(cryolite);
选自其他类的化合物,例如畜虫威(butacarb)、敌蝇威(dimetilan)、除线威(cloethocarb)、磷虫威(phosphocarb)、嘧啶磷(pirimiphos(-ethyl))、对硫磷(parathion(-ethyl))、虫螨畏(methacrifos)、o-水杨酸异丙酯(isopropyl o-salicylate)、敌百虫(trichlorfon)、trigolaner、硫丙磷(sulprofos)、丙虫磷(propaphos)、克线丹(sebufos)、哒硫磷(pyridathion)、发硫磷(prothoate)、除线磷(dichlofenthion)、砜吸磷(demeton-S-methyl sulfone)、氯唑磷(isazofos)、苯腈膦(cyanofenphos)、氯亚磷(dialifos)、三硫磷(carbophenothion)、autathiofos、aromfenvinfos(-methyl)、谷硫磷(azinphos(-ethyl))、毒死蜱(chlorpyrifos(-ethyl))、丁苯硫磷(fosmethilan)、碘硫磷(iodofenphos)、蔬果磷(dioxabenzofos)、安果(formothion)、地虫磷(fonofos)、吡氟硫磷(flupyrazofos)、丰索磷(fensulfothion)、乙嘧硫磷(etrimfos);
有机氯化合物,例如毒杀芬(camphechlor)、林丹(lindane)、七氯(heptachlor);或苯基吡唑类,例如乙酰虫腈(acetoprole)、pyrafluprole、pyriprole、氟吡唑虫(vaniliprole)、维吉霉素(sisapronil);或异噁唑啉类,例如sarolaner、阿福拉纳(afoxolaner)、lotilaner、氟雷拉纳(fluralaner);
拟除虫菊酯类(pyrethroid),例如(顺式、反式)甲氧苄氟菊酯(metofluthrin)、丙氟菊酯(profluthrin)、三氟醚菊酯(flufenprox)、溴氟菊酯(flubrocythrinate)、fubfenprox、五氟苯菊酯(fenfluthrin)、protrifenbut、反灭虫菊(pyresmethrin)、RU15525、环戊烯丙菊酯(terallethrin)、顺式苄呋菊脂(cis-resmethrin)、heptafluthrin、bioethanomethrin、生物氯菊酯(biopermethrin)、吡氯氰菊酯(fenpyrithrin)、顺式氯氰菊酯(cis-cypermethrin)、顺式苄氯菊酯(cis-permethrin)、功夫菊酯(clocythrin)、λ-氯氟氰菊酯(cyhalothrin(lamda-))、chlovaporthrin,或卤代烃化合物(HCH),
新烟碱类(neonicotinoids),例如硝虫噻嗪(nithiazine)
dicloromezotiaz、三氟苯嘧啶(triflumezopyrim)
大环内酯类,例如奈马克丁(nemadectin)、伊维菌素(ivermectin)、拉替菌素(latidectin)、莫西菌素(moxidectin)、塞拉菌素(selamectin)、依立诺克丁(eprinomectin)、多拉菌素(doramectin)、甲胺基阿维菌素苯甲酸盐(emamectinbenzoate);米尔贝肟(milbemycin oxime)烯虫硫酯(triprene)、保幼醚(epofenonane)、苯虫醚(diofenolan);
生物制剂、激素或信息素,例如天然产物,例如苏云金素(thuringiensin)、十二碳二烯醇(codlemone)或印楝(neem)组分
二硝基酚类,例如敌螨普(dinocap)、消螨通(dinobuton)、乐杀螨(binapacryl);
苯甲酰脲类,例如氟佐隆(fluazuron)、氟幼脲(penfluron),
脒衍生物类,例如chlormebuform、螨蜱胺(cymiazole)、得米地曲(demiditraz)
蜂巢瓦螨属杀螨剂类(beehive varroa acaricide),例如有机酸类,例如甲酸、草酸。
作为混合组分的选自杀体内寄生虫剂的示例性活性成分包括,但不限于抗蠕虫活性成分和抗原生动物活性成分。
抗蠕虫活性成分包括但不限于以下杀线虫活性化合物、杀吸虫活性化合物和/或杀绦虫活性化合物:
大环内酯类,例如:依立诺克丁(eprinomectin)、阿维菌素(abamectin)、奈马克丁(nemadectin)、莫西菌素(moxidectin)、多拉菌素(doramectin)、塞拉菌素(selamectin)、雷皮菌素(lepimectin)、拉替菌素(latidectin)、弥拜菌素(milbemectin)、伊维菌素(ivermectin)、埃玛菌素(emamectin)、美倍霉素(milbemycin);
苯并咪唑类和probenzimidazole,例如:奥苯达唑(oxibendazole)、甲苯咪唑(mebendazole)、三氯苯达唑(triclabendazole)、托布津(thiophanate)、帕苯咪唑(parbendazole)、奥芬达唑(oxfendazole)、奈托比胺(netobimin)、芬苯达唑(fenbendazole)、苯硫氨酯(febantel)、噻苯咪唑(thiabendazole)、环苯达唑(cyclobendazole)、坎苯达唑(cambendazole)、阿苯达唑亚砜(albendazole sulfoxide)、阿苯达唑(albendazole)、氟苯达唑(flubendazole);
缩肽类(depsipeptide),优选环状缩肽类,特别是24元环状缩肽类,例如:emodepside、PF1022A;
四氢嘧啶类,例如:莫仑太尔(morantel)、噻嘧啶(pyrantel)、奥克太尔(oxantel);
咪唑并噻唑类,例如:丁咪唑(butamisole)、左旋咪唑(levamisole)、四咪唑(tetramisole);
氨基苯基脒类,例如:阿米太尔(amidantel)、脱酰阿米太尔(dAMD)、三苯双脒(tribendimidine);
氨基乙腈类,例如:莫奈太尔(monepantel);
paraherquamide,例如:paraherquamide、得曲恩特(derquantel);
水杨酰苯胺类(salicylanilide),例如:三溴沙仑(tribromsalan)、溴沙尼特(bromoxanide)、溴替尼特(brotianide)、氯碘沙尼(clioxanide)、氯生太尔(closantel)、氯硝柳胺(niclosamide)、羟氯扎胺(oxyclozanide)、雷复尼特(rafoxanide);
取代的酚类,例如:硝碘酚腈(nitroxynil)、硫氯酚(bithionol)、双碘硝酚(disophenol)、六氯芬(hexachlorophene)、硝氯酚(niclofolan)、meniclopholan;
有机磷酸酯类,例如:三氯磷酸酯(trichlorfon)、naphthalofos、敌敌畏(dichlorvos)/DDVP、育畜磷(crufomate)、蝇毒磷(coumaphos)、哈洛克酮(haloxon);
哌嗪酮类/喹啉类,例如:吡喹酮(praziquantel)、依西太尔(epsiprantel);
哌嗪类,例如:哌嗪、羟嗪;
四环素类,例如:四环素、氯四环素(chlorotetracycline)、多西霉素(doxycycline)、氧四环素(oxytetracycline)、罗利环素(rolitetracycline);
各种其他种类,例如:丁萘脒(bunamidine)、尼立达唑(niridazole)、雷琐太尔(resorantel)、omphalotin、奥替普拉(oltipraz)、硝硫氰酯(nitroscanate)、硝碘酚腈(nitroxynil)、奥沙尼喹(oxamniquin)、mirasan、盐酸卢甘宋(miracil)、硫蒽酮(lucanthon)、海恩酮(hycanthon)、海托林(hetolin)、依米丁(emetin)、乙胺嗪(diethylcarbamazine)、双氯芬、地芬尼泰(diamfenetide)、氯硝安定(clonazepam)、酚乙铵(bephenium)、硝硫氰胺(amoscanate)、氯舒隆(clorsulon)。
抗原生动物活性成分包括,但不限于以下活性成分:
三嗪类,例如:地克珠利(diclazuril)、帕托珠利(ponazuril)、来曲珠利(letrazuril)、托曲珠利(toltrazuril);
聚醚离子载体类,例如:莫能菌素(monensin)、沙利霉素(salinomycin)、马杜霉素(maduramicin)、甲基盐霉素(narasin);
大环内酯类,例如:美尔贝霉素(milbemycin)、红霉素(erythromycin);
喹诺酮类,例如:恩诺沙星(enrofloxacin)、普多沙星(pradofloxacin);
奎宁类,例如:氯喹(chloroquine);
嘧啶类,例如:乙嘧啶(pyrimethamine);
磺酰胺类,例如:磺胺喹噁啉(sulfaquinoxaline)、甲氧苄氨嘧啶(trimethoprim)、磺胺氯吡嗪(sulfaclozin);
硫胺素类,例如:氨丙啉(amprolium);
林可酰胺类(lincosamide),例如:氯林肯霉素(clindamycin);
碳酰苯胺类,例如:咪多卡(imidocarb);
硝基呋喃类,例如:硝呋莫司(nifurtimox);
喹唑啉酮生物碱类,例如:卤夫酮(halofuginone);
各种其他种类,例如:奥沙尼喹(oxamniquin)、巴龙霉素(paromomycin);
微生物疫苗或抗原类,例如:罗氏巴贝斯虫亚种(Babesia canis rossi)、柔嫩艾美耳球虫(Eimeria tenella)、早熟艾美耳球虫(Eimeria praecox)、毒害艾美耳球虫(Eimeria necatrix)、和缓艾美耳球虫(Eimeria mitis)、巨型艾美耳球虫(Eimeriamaxima)、布氏艾美耳球虫(Eimeria brunetti)、堆型艾美耳球虫(Eimeria acervulina)、韦氏巴贝斯虫亚种(Babesia canis vogeli)、婴儿利什曼虫(Leishmania infantum)、犬巴贝斯虫亚种(Babesia canis canis)、胎生网尾线虫(Dictyocaulus viviparus)。
根据情况,如果混合组分基于其官能团能够与合适的碱或酸形成盐,则所提及的所有混合组分还可与合适的碱或酸形成盐。
病媒防治(vector control)
还可将式(I)的化合物用于病媒防治。在本发明的上下文中,病媒是能够将病原体(例如病毒、蠕虫、单细胞生物和细菌)从贮主(reservoir)(植物、动物、人类等)传播到宿主的节肢动物,特别是昆虫或蛛形纲动物。病原体可被机械地传播至宿主(例如通过非叮咬蝇(non-stinging fly)传播的沙眼)或在注入后传播至宿主(例如通过蚊子传播的疟原虫)。
病媒及其传播的疾病或病原体的实例为:
1)蚊
-按蚊:疟疾、丝虫病;
-库蚊:日本脑炎、丝虫病、其他病毒性疾病、其他蠕虫的传播;
-伊蚊:黄热病、登革热、其他病毒性疾病、丝虫病;
-蚋科(Simuliidae):蠕虫的传播、特别是旋盘尾丝虫(Onchocerca volvulus);
-毛蠓科(Psychodidae):利什曼病的传播
2)虱:皮肤感染、流行性斑疹伤寒;
3)蚤:鼠疫、地方性斑疹伤寒、绦虫类;
4)蝇:昏睡病(锥虫病);霍乱、其他细菌性疾病;
5)螨:螨病、流行性斑疹伤寒、立克次氏体痘、兔热病、圣路易斯脑炎、蜱媒脑炎(TBE)、克里米亚-刚果出血热(Crimean-Congo haemorrhagic fever)、疏螺旋体病(borreliosis);
6)蜱:borellioses如伯氏疏螺旋体(Borrelia bungdorferi sensu lato.)、达氏疏螺旋体(Borrelia duttoni)、蜱媒脑炎、Q热(贝氏柯克斯体(Coxiella burnetii))、巴贝西虫病(babesioses)(犬巴贝斯虫亚种)、埃里希体病(ehrlichiosis)。
在本发明的上下文中,病媒的实例为可将植物病毒传播到植物的昆虫,例如蚜虫、蝇、叶蝉或蓟马。能够传播植物病毒的其他病媒为叶螨、虱、甲虫和线虫。
在本发明的上下文中,病媒的其他实例为可将病原体传播到动物和/或人类的昆虫和蛛形纲动物如蚊,特别是伊蚊属,按蚊属,例如冈比亚按蚊(A.gambiae)、阿拉伯按蚊(A.arabiensis)、不吉按蚊(A.funestus)、大劣按蚊(A.dirus)(疟疾),和库蚊属;毛蠓科(Psychodidae)如白蛉属(Phlebotomus)、罗蛉属(Lutzomyia);虱;蚤;蝇;螨和蜱。
如果式(I)的化合物为抗破坏性的(resistance-breaking),则病媒防治也是可行的。
式(I)的化合物适用于预防由病媒传播的疾病和/或病原体。因此,本发明的另一个方面为式(I)的化合物用于病媒防治的用途,例如在农业、园艺、林业、花园和休闲设施中,以及在材料和贮存产品的保护中。
工业材料的保护
式(I)的化合物适于保护工业材料抵抗昆虫的侵袭或破坏,所述昆虫例如来自鞘翅目、膜翅目、等翅目、鳞翅目、啮虫目和衣鱼目。
在本发明的上下文中,工业材料应理解为意指无生命材料,如优选塑料、胶粘剂、胶料、纸和卡片、皮革、木材、加工的木制品和涂料组合物。特别优选本发明用于保护木材的用途。
在另一个实施方案中,式(I)的化合物与至少一种其他杀昆虫剂和/或至少一种杀真菌剂一起使用。
在另一个实施方案中,式(I)的化合物为即用型农药的形式,意指它们可不经进一步的改性而施用于所述材料。有用的其他杀昆虫剂或杀真菌剂特别包括上文中提及的那些。
出人意料地,还已发现,式(I)的化合物可用于保护与盐水或微咸水接触的物体(特别是船体、筛、网、建筑物、系泊用具和信号系统)免受污损。同样地,式(I)的化合物可单独或与其他活性成分结合用作抗污剂。
在卫生领域中的动物害虫的防治
式(I)的化合物适于防治卫生领域中的动物害虫。更具体而言,本发明可用于室内保护领域、卫生保护领域和贮存产品的保护中,特别是用于防治在封闭空间(例如住宅、工厂车间、办公室、车辆舱室、动物饲养设施)中遇到的昆虫、蛛形纲动物、蜱和螨。为了防治动物害虫,将式(I)的化合物单独使用或与其他活性成分和/或助剂结合使用。其优选用于室内杀昆虫剂产品中。式(I)的化合物对敏感和抗性物种以及对所有发育阶段均有效。
这些害虫包括以下害虫:例如,蛛形纲,蝎目(Scorpiones)、蜘蛛目(Araneae)和盲蛛目(Opiliones);唇足纲和倍足纲;昆虫纲蜚蠊目,鞘翅目、革翅目、双翅目、异翅目、膜翅目、等翅目、鳞翅目、虱目、啮虫目、跳跃目或直翅目、蚤目和衣鱼目;以及软甲纲(Malacostraca)等足目。
通过以下方式进行施用:例如,气雾剂、无压喷雾产品(例如泵式喷雾剂和雾化喷雾剂)、自动起雾体系、喷雾剂、泡沫剂、凝胶剂、具有由纤维素或塑料制成的蒸发片剂(evaporator tablet)的蒸发产品、液体蒸发剂、凝胶和薄膜蒸发剂、推进器驱动的蒸发剂、无动力或无源的蒸发体系、捕蛾纸、捕蛾袋和捕蛾胶,作为颗粒剂或粉剂,用于撒播的饵料或饵站(bait station)。
制备实施例:
2-[3-乙基磺酰基-5-(三氟甲基)-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基]-3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶(I-1)
在120℃下在微波合成设备(Anton Paar,Monowave 400)中将265.0mg(0.56mmol)2-[3-溴-5-(三氟甲基)-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基]-3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶、657.2mg(5.66mmol)乙基亚磺酸钠和16.2mg(0.08mmol)碘化亚铜(I)在15ml的N,N-二甲基甲酰胺中搅拌12小时。随后,向反应混合物中加入氯化钠溶液,并将其用乙酸乙酯萃取。将有机相用硫酸钠干燥,然后在减压下蒸馏出溶剂。残余物通过柱色谱纯化法通过制备型HPLC纯化,使用水/乙腈梯度作为洗脱液。
logP(HCOOH):3.21;MH+:482;1H NMR(400MHz,DMSO-d6)ppm:1.26(t,3H),2.18-2.22(m,1H),2.33-2.37(m,1H),3.00-3.06(m,1H),3.19(br.s,1H),3.47-3.53(m,1H),3.75(q,2H),3.95(s,3H),4.30-4.36(m,1H),4.47-4.51(m,1H),8.64(s,1H),8.86(s,1H)。
2-[3-溴-5-(三氟甲基)-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-基]-3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶
在室温下在氩气下,将250mg(1.30mmol)N2-甲基-5-(三氟甲基)吡啶-2,3-二胺、502mg(1.63mmol)3-溴-5-(三氟甲基)-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-甲酸和251mg(1.30mmol)1-(3-二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐(EDCI)在10ml吡啶中搅拌16小时。在减压下除去反应混合物中的溶剂,向残余物中加入水,并将其用乙酸乙酯萃取。将有机相用硫酸钠干燥,然后在减压下蒸馏出溶剂。然后将残余物在10ml浓乙酸中在100℃下搅拌8小时。混合物用水稀释,并用乙酸乙酯萃取三次。用水和碳酸氢钠溶液洗涤合并的有机相,除去有机相,并用乙酸乙酯萃取水相。将合并的有机相用硫酸钠干燥,然后在减压下蒸馏出溶剂。
logP(HCOOH):3.99;MH+:468;1H NMR(400MHz,DMSO-d6)ppm:2.12-2.17(m,1H),2.33-2.37(m,1H),2.76-2.83(m,1H),3.05-3.10(m,1H),3.17(br.s,1H),4.10(s,3H),4.24-4.32(m,1H),4.44-4.48(m,1H),8.61(s,1H),8.80(s,1H)。
3-溴-5-(三氟甲基)-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-甲酸
将881mg(3.76mmol)5-(三氟甲基)-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-甲酸和337mg(4.13mmol)N-溴代琥珀酰亚胺溶于60ml氯仿中,并在室温下搅拌72小时。向反应混合物中加入水,除去有机相并用硫酸钠干燥,然后在减压下蒸馏出溶剂。
logP(HCOOH):1.75;MH+:313;1H NMR(400MHz,DMSO-d6)ppm:2.00-2.10(m,1H),2.27-2.33(m,1H),2.64-2.71(m,1H),2.93-2.98(m,1H),3.05-3.14(s,1H),4.11-4.19(m,1H),4.31-4.35(m,1H),12.95(br.s,1H)。
5-(三氟甲基)-4,5,6,7-四氢吡唑并[1,5-a]吡啶-2-甲酸
在4巴下在100mg(0.44mmol)氧化钯(IV)的存在下,将1.00g(4.34mmol)5-(三氟甲基)吡唑并[1,5-a]吡啶-2-甲酸在65ml乙醇中氢化12小时。随后,将反应混合物通过Celite过滤并用乙醇洗涤,在减压下蒸馏出溶剂。
logP(HCOOH):1.28;MH+:235;1H NMR(400MHz,DMSO-d6)ppm:1.98-2.08(m,1H),2.26-2.30(m,1H),2.74-2.81(m,1H),2.97-3.08(m,1H),3.11-3.16(s,1H),4.10-4.17(m,1H),4.30-4.34(m,1H),6.52(s,1H),12.50(br.s,1H)。
类似于所述实施例,并通过上述制备方法,可获得以下式(I)的化合物:
5-(三氟甲基)吡唑并[1,5-a]吡啶-2-甲酸
在80℃下将2.00g(6.61mmol)5-(三氟甲基)吡唑并[1,5-a]吡啶-2,3-二甲酸二甲酯在50ml 50%的硫酸中搅拌3小时。用冰浴进行冷却,同时用5N的氢氧化钠溶液使冷却的溶液碱化,并用乙酸乙酯萃取。用2N的盐酸将水相调节至pH 2-3,并用水稀释直至溶解完全。将水相用乙酸乙酯萃取三次,并用硫酸钠干燥,然后在减压下蒸馏出溶剂。残余物通过柱色谱纯化法通过制备型HPLC纯化,使用水/乙腈混合物作为洗脱液。
logP(HCOOH):1.58;MH+:231;1H NMR(400MHz,DMSO-d6)ppm:7.29-7.32(m,2H),8.36(s,1H),8.93(d,1H),13.4(br.s,1H)。
5-(三氟甲基)吡唑并[1,5-a]吡啶-2,3-二甲酸二甲酯
在室温下,向1.00g(3.44mmol)4-(三氟甲基)-1-氨基碘化吡啶鎓和953mg(6.89mmol)碳酸钾在7ml二甲基甲酰胺中的初始进料中滴加514mg(3.62mmol)乙炔二甲酸二甲酯。将反应混合物在室温下搅拌2小时,在此期间引入空气。随后,过滤混合物,除去母液,并在减压下蒸馏出溶剂。将残余物溶于水中,并用乙醚萃取。将有机相用硫酸钠干燥,然后在减压下蒸馏出溶剂。
logP(HCOOH):2.57;MH+:303;1H NMR(400MHz,DMSO-d6)ppm:3.89(s,3H),3.95(s,3H),7.57(d,1H),8.38(s,1H),9.15(d,1H)。
4-(三氟甲基)-1-氨基碘化吡啶鎓
向8.54g(67.9mmol)羟胺-O-磺酸在50ml水中的初始进料中加入10.00g(67.9mmol)4-(三氟甲基)吡啶。将混合物在90℃下搅拌30分钟,并且在冷却之后,加入9.395g(67.9mmol)碳酸钾。将残余物溶于85ml乙醇中并过滤,向母液中加入9ml氢碘酸(67.9mmol,57%强度)。在-20℃下保持14小时后,过滤出沉淀的固体,并且无需进一步纯化即可进一步转化。
类似于所述实施例,并且通过上述制备方法,可获得以下式(I)的化合物:
分析测定
如果在文本的特定段落中没有针对特定的分析测定方法的单独说明,则下文中记载的分析测定方法涉及整个文档中的任何信息。
logP值
logP值根据EEC Directive 79/831Annex V.A8通过HPLC(高效液相色谱)在反向柱(C 18)上测量。温度:55℃。
在酸性范围内的LC-MS测定在pH 2.7下使用0.1%甲酸水溶液和乙腈(含有0.1%甲酸)作为洗脱液进行;线性梯度为10%乙腈至95%乙腈。表中称为logP(HCOOH)。
在中性范围内的LC-MS测定在pH 7.8下使用0.001摩尔碳酸氢铵水溶液和乙腈作为洗脱液进行;线性梯度为10%乙腈至95%乙腈。在表中称为logP(中性)。
使用具有已知logP值的直链的烷-2-酮(具有3至16个碳原子)进行校准(通过两个连续烷酮之间的线性内插法基于保留时间测定logP值)。
质谱
在酸性色谱条件下通过LC-MS进行测定[M+H]+或M-,使用1ml甲酸每升乙腈和0.9ml甲酸每升Millipore水作为洗脱液。使用Zorbax Eclipse Plus C18 50mm*2.1mm,1.8μm柱,柱箱温55℃。
仪器:
LC-MS3:Waters UPLC,具有SQD2质谱仪和SampleManager自动进样器。线性梯度:0.0至1.70分钟,从10%乙腈至95%乙腈;1.70至2.40分钟,恒定为95%乙腈,流速0.85ml/分钟。
LC-MS6和LC-MS7:Agilent 1290LC,Agilent MSD质谱仪,HTS PAL自动进样器。线性梯度:0.0至1.80分钟,从10%乙腈至95%乙腈;1.80至2.50分钟,恒定为95%乙腈,流速1.0ml/分钟。
在中性色谱条件下通过LC-MS使用乙腈和Millipore水以79mg/l碳酸铵作为洗脱液进行测定[M+H]+。
仪器:
LC-MS4:Waters IClass Acquity,具有QDA质谱仪和FTN自动进样器(WatersAcquity 1.7μm 50mm*2.1mm柱,柱箱温45℃)。线性梯度:0.0至2.10分钟,从10%乙腈至95%乙腈;2.10至3.00分钟,恒定为95%乙腈,流速0.7ml/分钟。
LC-MS5:Agilent 1100LC System,具有MSD质谱仪和HTS PAL自动进样器(柱:Zorbax XDB C18 1.8μm 50mm*4.6mm,柱箱温55℃)。线性梯度:0.0至4.25分钟,从10%乙腈至95%乙腈;4.25至5.80分钟,恒定为95%乙腈,流速2.0ml/分钟。
在所有情况下,由对具有3至16个碳的同源系列的直链烷-2-酮的校准测量来确定保留时间指数,其中将第一种烷酮的系数设为300,将最后一种烷酮的系数设为1600,并且以线性方式将连续烷酮内插在所述值之间。
1H NMR光谱的测量使用装有1.7mm TCI探头的Bruker Avance III 400MHz光谱仪在溶剂CD3CN、CDCl3或d6-DMSO中的溶液中进行,使用四甲基硅烷作为标准物(0.00ppm)。或者,使用装有5mm CPNMP探头的Bruker Avance III 600MHz光谱仪或装有5mm TCI探头的Bruker Avance NEO 600MHz光谱仪进行测量。通常,测量在298K的探头温度下进行。如果使用了不同的测量温度,则对此单独说明。
所选实施例的NMR数据
NMR峰列表方法
所选实施例的1H-NMR数据以1H-NMR峰列表的形式记录。对于每个信号峰,首先列出了以ppm计的δ值,然后在圆括号中列出了信号强度。不同信号峰的δ值-信号强度数对通过分号彼此间隔列出。
因此,一个实施例的峰列表采取以下形式:
δ1(强度1);δ2(强度2);……;δi(强度i);……;δn(强度n)
尖峰信号的强度与NMR谱的打印实例中以cm计的信号高度有关,并且显示了信号强度的真实比例。在宽信号的情况下,可以显示几个峰或信号的中间部分及其与谱图中的最强信号相比的相对强度。
为校准1H NMR谱的化学位移,使用四甲基硅烷和/或溶剂的化学位移,特别是在谱图在DMSO中测量的情况下。因此,在NMR峰列表中,四甲基硅烷峰可以出现,但不是必须出现。
1H NMR峰列表与常规的1H NMR打印件相似,并且因此通常包含在常规的NMR说明中列出的所有峰。
另外,与常规的1H NMR打印件一样,它们可以显示溶剂信号、目标化合物的立体异构体(其同样形成本发明的主题)信号和/或杂质的峰的信号。
在溶剂和/或水的δ范围内的化合物信号的报告中,1H NMR峰列表中显示了常见的溶剂峰(例如DMSO在DMSO-D6中的峰)和水的峰,平均来看,其通常具有高的强度。
平均来看,目标化合物的立体异构体的峰和/或杂质的峰通常具有低于目标化合物(例如纯度>90%)的峰的强度。
此类立体异构体和/或杂质可以是特定的制备方法所特有的。因此,它们的峰可以通过“副产物指纹(side-product fingerprints)”帮助识别对制备方法的再现。
如果需要,通过已知方法(MestreC、ACD模拟,以及使用经验估算的预期值)计算目标化合物的峰的专业人员可任选地使用额外的强度过滤器来分离目标化合物的峰。这种分离与在常规的1H NMR说明中挑选相关峰类似。
可在研究公开数据库(the Research Disclosure Database)第564025号中找到1H NMR峰列表的其他详细信息。
用途实施例
猫栉头蚤(Ctenocephalides felis)—与成年猫蚤的体外接触试验
为涂覆测试管,首先将9mg活性成分溶于1ml分析用丙酮中,然后用分析用丙酮稀释至所需的浓度。通过在定轨振荡器上转动和摇晃(在30rpm下摇晃旋转2小时),将250μl溶液均匀分布在25ml玻璃管的内壁和底部上。在均匀分布的情况下,使用900ppm的活性成分溶液和44.7cm2的内表面积,可实现5μg/cm2的基于面积的剂量。
在溶剂蒸发后,在试管中装入5-10只成年猫蚤(猫栉头蚤),用带孔的塑料盖封闭,并在室温和环境湿度下平放培育。48小时后,测定功效。为此,将试管直立,并将蚤敲至试管底部。将在底部保持静止不动或以不协调的方式移动的蚤视为死亡或将要死亡。
如果在该试验中,在5μg/cm2的施用率下实现至少80%的功效,则物质对猫栉头蚤显示出良好的功效。100%功效意指所有蚤均死亡或将要死亡。0%功效意指没有蚤受到伤害。
在该试验中,例如,制备实施例的以下化合物在5μg/cm2(=500g/ha)的施用率下显示出100%的功效:I-05。
血红扇头蜱(Rhipicephalus sanguineus)—与成年棕色狗蜱的体外接触试验
为涂覆测试管,首先将9mg活性成分溶于1ml分析用丙酮中,然后用分析用丙酮稀释至所需的浓度。通过在定轨振荡器上转动和摇晃(在30rpm下摇晃旋转2小时),将250μl溶液均匀分布在25ml试验管的内壁和底部上。在均匀分布的情况下,使用900ppm的活性成分溶液和44.7cm2的内表面积,可实现5μg/cm2的基于面积的剂量。
在溶剂蒸发后,在试管中装入5-10只成年狗蜱(血红扇头蜱),用带孔的塑料盖封闭,并在黑暗中在室温和环境湿度下平放培育。48小时后,测定功效。为此,将蜱敲至试管底部,并在45-50℃下在加热板上温育至多5分钟。将在底部保持静止不动或以不协调的方式移动以致其不能通过向上爬来有意避开热量的蜱视为死亡或将要死亡。
如果在该试验中在5μg/cm2的施用率下实现至少80%的功效,则物质对血红扇头蜱显示出良好的功效。100%功效意指所有蜱均死亡或将要死亡。0%功效意指没有蜱受到伤害。
在该试验中,例如,制备实施例的以下化合物在5μg/cm2(=500g/ha)的施用率下显示出100%的功效:I-05。
微小牛蜱(Boophilus microplus)—注射试验
溶剂:二甲基亚砜
为制备合适的活性成分制剂,将10mg活性成分与0.5ml溶剂混合,并用溶剂将该浓缩液稀释至所需浓度。
将1μl活性成分溶液注射到5只饱食的成年雌性牛蜱(cattle ticks)(微小牛蜱)的腹部中。将动物转移到培养皿中并放置在温控室中。
7天后通过产下受精卵来评估功效。将没有明显能育性的卵存储在温控箱中,直至在约42天后孵出幼虫。100%功效意指没有蜱产下任何受精卵;0%意指所有的卵都是能育的。
在该试验中,例如,制备实施例的以下化合物在20μg/动物的施用率下显示出100%的功效:I-05、I-13。
猫栉头蚤—口服试验
溶剂:二甲基亚砜
为制备合适的活性成分制剂,将10mg活性成分与0.5ml二甲基亚砜混合。用柠檬酸牛血稀释得到所需浓度。
将约20只未喂食的成年猫蚤(猫栉头蚤)放入到一个顶部和底部用纱布封闭的腔室内。将底端用石蜡膜封闭的金属圆柱体放置到腔室上。圆柱体含有血液/活性成分制剂,蚤可通过石蜡膜吸取所述制剂。
在2天后,评估以%计的杀死率。100%意指所有的蚤均已被杀死;0%意指没有蚤被杀死。
在该试验中,例如,制备实施例的以下化合物在100ppm的施用率下显示出100%的功效:I-11、I-13。
在该试验中,例如,制备实施例的以下化合物在100ppm的施用率下显示出95%的功效:I-05。
在该试验中,例如,制备实施例的以下化合物在100ppm的施用率下显示出90%的功效:I-02、I-15。
铜绿蝇(Lucilia cuprina)试验
溶剂:二甲基亚砜
为制备合适的活性成分制剂,将10mg活性成分与0.5ml二甲基亚砜混合,并用水将浓缩液稀释至所需浓度。
将约20只澳大利亚绵羊绿头蝇(Australian sheep blowfly)(铜绿蝇)的L1幼虫转移到含有切碎的马肉和所需浓度的活性成分制剂的试验容器中。
2天后,测定以%计的杀死率。100%意指所有的幼虫都已被杀死;0%意指没有幼虫被杀死。
在该试验中,例如,制备实施例的以下化合物在100ppm的施用率下显示出100%的功效:I-02。
家蝇(Musca
domestica)试验
溶剂:二甲基亚砜
为制备合适的活性成分制剂,将10mg活性成分与0.5ml二甲基亚砜混合,并用水将浓缩液稀释至所需浓度。
向含有用糖溶液和所需浓度的活性成分制剂处理的海绵的容器中装入10只成年家蝇(家蝇)。
2天后,测定以%计的杀死率。100%意指所有的蝇都已被杀死;0%意指没有蝇被杀死。
在该试验中,例如,制备实施例的以下化合物在100ppm的施用率下显示出80%的功效:I-02、I-05。
黄瓜条叶甲(Diabrotica
balteata)—喷洒试验
溶剂:78 重量份的丙酮
1.5 重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性成分制剂,将1重量份活性成分溶于所述给定重量份的溶剂中,并用含有浓度为1000ppm的乳化剂的水补足直至获得所需浓度。通过用含有乳化剂的水稀释来制备其他试验浓度。
将预溶胀的小麦谷粒(小麦(Triticum aestivum))在装有琼脂和少量水的多孔板中温育1天(每孔5颗种子)。向发芽的小麦种子喷洒所需浓度的活性成分制剂。随后,使每个空腔感染10-20只黄瓜条叶甲甲虫幼虫。
7天后,测定以%计的功效。100%意指所有的小麦植物都已经如未经处理、未被感染的对照组那样成长;0%意指没有小麦植物生长。
在该试验中,例如,制备实施例的以下化合物在160μg/孔的施用率下显示出100%的良好的活性:I-17、I-18、I-19。
桃蚜(Myzus persicae)—口服试验
溶剂:100 重量份的丙酮
为制备合适的活性化合物制剂,将1重量份活性成分溶于所述重量份的溶剂中,并用水配补足至所需浓度。
将50μl活性成分制剂转移到微量滴定板中,并用150μl IPL41昆虫培养基(33%+15%糖)补足至200μl的最终体积。随后,用石蜡膜密封所述板,第二微量滴定板中的绿桃蚜(桃蚜)的混合种群可刺穿石蜡膜并吸取所述溶液。
5天后,测定以%计的功效。100%意指所有的蚜虫都已被杀死,0%意指没有蚜虫被杀死。
在该试验中,例如,制备实施例的以下化合物在4ppm的施用率下显示出100%的功效:I-01、I-02、I-03、I-04、I-05、I-07、I-08、I-10、I-11、I-12、I-13、I-14、I-17、I-18、I-19。
在该试验中,例如,制备实施例的以下化合物在4ppm的施用率下显示出90%的功效:I-09、I-15、I-16。
桃蚜—喷洒试验
溶剂:78.0 重量份的丙酮
1.5 重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性成分制剂,将1重量份活性成分溶于所述重量份的溶剂中,并用含有浓度为1000ppm的乳化剂的水补足至所需浓度。为制备其他试验浓度,将所述制剂用含有乳化剂的水稀释。
用含所需浓度的活性成分制剂喷洒感染所有阶段的绿桃蚜(桃蚜)的大白菜(白菜(Brassica pekinensis))的叶盘。
5天后,测定以%计的功效。100%意指所有的蚜虫都已被杀死,0%意指没有蚜虫被杀死。
在该试验中,例如,制备实施例的以下化合物在100g/ha的施用率下显示出100%的功效:I-04、I-05、I-14。
在该试验中,例如,制备实施例的以下化合物在100g/ha的施用率下显示出90%的功效:I-02、I-03、I-06、I-09、I-10、I-11、I-12、I-13、I-15、I-18。
辣根猿叶虫(Phaedon cochleariae)—喷洒试验
溶剂:78.0 重量份的丙酮
1.5 重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性成分制剂,将1重量份活性成分溶于所述重量份的溶剂中,并用含有浓度为1000ppm的乳化剂的水补足至所需浓度。为制备其他试验浓度,将所述制剂用含有乳化剂的水稀释。
用所需浓度的活性成分制剂喷洒大白菜(白菜(Brassica pekinensis))的叶盘,并且在干燥后,用芥菜甲虫(辣根猿叶虫)的幼虫侵害。
7天后,测定以%计的功效。100%意指所有的甲虫幼虫都已被杀死,0%意指没有甲虫幼虫被杀死。
在该试验中,例如,制备实施例的以下化合物在100g/ha的施用率下显示出100%的功效:I-01、I-03、I-12。
草地贪夜蛾(Spodoptera frugiperda)—喷洒试验
溶剂:78.0 重量份的丙酮
1.5 重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性成分制剂,将1重量份活性成分溶于所述重量份的溶剂中,并用含有浓度为1000ppm的乳化剂的水补足至所需浓度。为制备其他试验浓度,将所述制剂用含有乳化剂的水稀释。
用所需浓度的活性成分制剂喷洒玉米(玉米(Zea mays))的叶盘,并且在干燥后,用粘虫(草地贪夜蛾)的毛虫侵害。
7天后,测定以%计的功效。100%意指所有的毛虫都已被杀死,0%意指没有毛虫被杀死。
在该试验中,例如,制备实施例的以下化合物在100g/ha的施用率下显示出100%的功效:I-01、I-08、I-13、I-15、I-17、I-19。
在该试验中,例如,制备实施例的以下化合物在100g/ha的施用率下显示出83%的功效:I-11。
二斑叶螨(Tetranychus urticae)—喷洒试验,OP抗性的
溶剂:78.0 重量份的丙酮
1.5 重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性成分制剂,将1重量份活性成分溶于所述重量份的溶剂中,并用含有浓度为1000ppm的乳化剂的水补足至所需浓度。为制备其他试验浓度,将所述制剂用含有乳化剂的水稀释。
用所需浓度的活性成分制剂喷洒感染所有阶段的温室红叶螨(二斑叶螨)的豆叶(菜豆)的叶盘。
6天后,测定以%计的功效。100%意指所有的叶螨都已被杀死,0%意指没有叶螨被杀死。
在该试验中,例如,制备实施例的以下化合物在100g/ha的施用率下显示出100%的功效:I-04、I-13。
在该试验中,例如,制备实施例的以下化合物在100g/ha的施用率下显示出90%的功效:I-10。
Claims (11)
1.式(I)的化合物
其中
Aa为-C(R8)(R9)-,
Ab为–C(R10)(R11)-,
Ac为–C(R12)(R13)-,
Ad为–C(R14)(R15)-,
R1为(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-氰基烷基、(C1-C6)-羟基烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C1-C6)-卤代烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-烯氧基-(C1-C6)-烷基、(C2-C6)-卤代烯氧基-(C1-C6)-烷基、(C2-C6)-卤代烯基、(C2-C6)-氰基烯基、(C2-C6)-炔基、(C2-C6)-炔氧基-(C1-C6)-烷基、(C2-C6)-卤代炔氧基-(C1-C6)-烷基、(C2-C6)-卤代炔基、(C2-C6)-氰基炔基、(C3-C8)-环烷基、(C3-C8)-环烷基-(C3-C8)-环烷基、(C1-C6)-烷基-(C3-C8)-环烷基、卤代-(C3-C8)-环烷基、氨基、(C1-C6)-烷基氨基、二-(C1-C6)-烷基氨基、(C3-C8)-环烷基氨基、(C1-C6)-烷基羰基氨基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-卤代烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-卤代烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷基羰基-(C1-C6)-烷基、(C1-C6)-卤代烷基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-卤代烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基氨基、氨基磺酰基-(C1-C6)-烷基、(C1-C6)-烷基氨基磺酰基-(C1-C6)-烷基、二-(C1-C6)-烷基氨基磺酰基-(C1-C6)-烷基,
R8、R9、R10、R11、R12、R13、R14、R15独立地为氢、氰基、卤素、硝基、乙酰基、羟基、氨基、SCN、三-(C1-C6)-烷基甲硅烷基、(C3-C8)-环烷基、(C3-C8)-环烷基-(C3-C8)-环烷基、(C1-C6)-烷基-(C3-C8)-环烷基、卤代-(C3-C8)-环烷基、氰基-(C3-C8)-环烷基、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-氰基烷基、(C1-C6)-羟基烷基、羟基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-氰基烯基、(C2-C6)-炔基、(C2-C6)-卤代炔基、(C2-C6)-氰基炔基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-氰基烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C6)-烷氧基、(C1-C6)-烷基羟基亚氨基、(C1-C6)-烷氧基亚氨基、(C1-C6)-烷基-(C1-C6)-烷氧基亚氨基、(C1-C6)-卤代烷基-(C1-C6)-烷氧基亚氨基、(C1-C6)-烷硫基、(C1-C6)-卤代烷硫基、(C1-C6)-烷氧基-(C1-C6)-烷硫基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基、(C1-C6)-卤代烷基磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基磺酰基、(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰氧基、(C1-C6)-烷基羰基、(C1-C6)-烷硫基羰基、(C1-C6)-卤代烷基羰基、(C1-C6)-烷基羰基氧基、(C1-C6)-烷氧基羰基、(C1-C6)-卤代烷氧基羰基、氨基羰基、(C1-C6)-烷基氨基羰基、(C1-C6)-烷基氨基硫代羰基、二-(C1-C6)-烷基氨基羰基、二-(C1-C6)-烷基氨基硫代羰基、(C2-C6)-烯基氨基羰基、二-(C2-C6)-烯基氨基羰基、(C3-C8)-环烷基氨基羰基、(C1-C6)-烷基磺酰基氨基、(C1-C6)-烷基氨基、二-(C1-C6)-烷基氨基、氨基磺酰基、(C1-C6)-烷基氨基磺酰基、二-(C1-C6)-烷基氨基磺酰基、(C1-C6)-烷基亚砜亚胺基、氨基硫代羰基、(C1-C6)-烷基氨基硫代羰基、二-(C1-C6)-烷基氨基硫代羰基、(C3-C8)-环烷基氨基、NHCO-(C1-C6)-烷基((C1-C6)-烷基羰基氨基),
在每种情况下为任选地被相同或不同地单取代或多取代的芳基或杂芳基,其中(在杂芳基的情况下)可任选地存在至少一个羰基和/或其中在每种情况下的可能的取代基如下:氰基、羧基、卤素、硝基、乙酰基、羟基、氨基、SCN、三-(C1-C6)烷基甲硅烷基、(C3-C8)环烷基、(C3-C8)环烷基-(C3-C8)环烷基、(C1-C6)烷基-(C3-C8)环烷基、卤代(C3-C8)环烷基、(C1-C6)烷基、(C1-C6)卤代烷基、(C1-C6)氰基烷基、(C1-C6)羟基烷基、羟基羰基-(C1-C6)-烷氧基、(C1-C6)烷氧基羰基-(C1-C6)烷基、(C1-C6)烷氧基-(C1-C6)烷基、(C2-C6)烯基、(C2-C6)卤代烯基、(C2-C6)氰基烯基、(C2-C6)炔基、(C2-C6)卤代炔基、(C2-C6)氰基炔基、(C1-C6)烷氧基、(C1-C6)卤代烷氧基、(C1-C6)氰基烷氧基、(C1-C6)烷氧基羰基-(C1-C6)烷氧基、(C1-C6)烷氧基-(C1-C6)烷氧基、(C1-C6)烷基羟基亚氨基、(C1-C6)烷氧基亚氨基、(C1-C6)烷基-(C1-C6)烷氧基亚氨基、(C1-C6)卤代烷基-(C1-C6)烷氧基亚氨基、(C1-C6)烷硫基、(C1-C6)卤代烷硫基、(C1-C6)烷氧基-(C1-C6)烷硫基、(C1-C6)烷硫基-(C1-C6)烷基、(C1-C6)烷基亚磺酰基、(C1-C6)卤代烷基亚磺酰基、(C1-C6)烷氧基-(C1-C6)烷基亚磺酰基、(C1-C6)烷基亚磺酰基-(C1-C6)烷基、(C1-C6)烷基磺酰基、(C1-C6)卤代烷基磺酰基、(C1-C6)烷氧基-(C1-C6)烷基磺酰基、(C1-C6)烷基磺酰基-(C1-C6)烷基、(C1-C6)烷基磺酰氧基、(C1-C6)烷基羰基、(C1-C6)卤代烷基羰基、(C1-C6)烷基羰基氧基、(C1-C6)烷氧基羰基、(C1-C6)卤代烷氧基羰基、氨基羰基、(C1-C6)烷基氨基羰基、二-(C1-C6)烷基氨基羰基、(C2-C6)烯基氨基羰基、二-(C2-C6)-烯基氨基羰基、(C3-C8)环烷基氨基羰基、(C1-C6)烷基磺酰基氨基、(C1-C6)烷基氨基、二-(C1-C6)烷基氨基、氨基磺酰基、(C1-C6)烷基氨基磺酰基、二-(C1-C6)烷基氨基磺酰基、(C1-C6)烷基亚砜亚胺基、氨基硫代羰基、(C1-C6)烷基氨基硫代羰基、二-(C1-C6)烷基氨基硫代羰基、(C3-C8)环烷基氨基、(C1-C6)烷基羰基氨基,
Q为部分饱和的或饱和的杂环的或杂芳族的8、9、10、11或12元的稠合双环或三环的环体系,其中可任选地存在至少一个羰基和/或其中所述环体系任选地被相同或不同地单取代或多取代,并且其中所述取代基可独立地选自:氰基、卤素、硝基、乙酰基、羟基、氨基、SCN、三-(C1-C6)-烷基甲硅烷基、(C3-C8)-环烷基、氰基-(C3-C8)-环烷基、(C3-C8)-环烷基-(C3-C8)-环烷基、(C1-C6)-烷基-(C3-C8)-环烷基、卤代-(C3-C8)-环烷基、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-氰基烷基、(C1-C6)-羟基烷基、羟基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-氰基烯基、(C2-C6)-炔基、(C2-C6)-炔氧基-(C1-C4)-烷基、(C2-C6)-卤代炔基、(C2-C6)-氰基炔基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-卤代烷氧基-(C1-C6)-烷基、(C2-C6)-烯氧基-(C1-C6)-烷基、(C2-C6)-卤代烯氧基-(C1-C6)-烷基、(C1-C6)-氰基烷氧基、(C1-C6)-烷氧基羰基-(C1-C6)-烷氧基、(C1-C6)-烷氧基-(C1-C6)-烷氧基、(C1-C6)-烷基羟基亚氨基、(C1-C6)-烷氧基亚氨基、(C1-C6)-烷基-(C1-C6)-烷氧基亚氨基、(C1-C6)-卤代烷基-(C1-C6)-烷氧基亚氨基、(C1-C6)-烷硫基、(C1-C6)-卤代烷硫基、(C1-C6)-烷氧基-(C1-C6)-烷硫基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基、(C1-C6)-卤代烷基磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基磺酰基、(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰氧基、(C1-C6)-烷基羰基、(C1-C6)-烷基羰基-(C1-C6)-烷基、(C1-C6)-烷硫基羰基、(C1-C6)-卤代烷基羰基、(C1-C6)-烷基羰基氧基、(C1-C6)-烷氧基羰基、(C1-C6)-卤代烷氧基羰基、氨基羰基、(C1-C6)-烷基氨基羰基、(C1-C6)-烷基氨基硫代羰基、二-(C1-C6)-烷基氨基羰基、二-(C1-C6)-烷基氨基硫代羰基、(C2-C6)-烯基氨基羰基、二-(C2-C6)-烯基氨基羰基、(C3-C8)-环烷基氨基羰基、(C1-C6)-烷基磺酰基氨基、(C1-C6)-烷基氨基、二-(C1-C6)-烷基氨基、氨基磺酰基、(C1-C6)-烷基氨基磺酰基、二-(C1-C6)-烷基氨基磺酰基、(C1-C6)-烷基亚砜亚胺基、氨基硫代羰基、(C1-C6)-烷基氨基硫代羰基、二-(C1-C6)-烷基氨基硫代羰基、(C3-C8)-环烷基氨基、NHCO-(C1-C6)-烷基((C1-C6)-烷基羰基氨基),
或其中所述取代基可独立地选自苯基或5或6元杂芳族环,其中所述苯基或所述环可任选地被以下基团相同或不同地单取代或多取代:C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C1-C6-卤代烷基、C2-C6-卤代烯基、C2-C6-卤代炔基、C3-C6-卤代环烷基、卤素、CN、NO2、C1-C4-烷氧基、C1-C4-卤代烷氧基,
n为0、1或2。
2.根据权利要求1的式(I)的化合物,其中
Aa为–C(R8)(R9)-,
Ab为–C(R10)(R11)-,
Ac为–C(R12)(R13)-,
Ad为–C(R14)(R15)-,
R1为(C1-C4)-烷基、(C1-C4)-羟基烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C1-C4)卤代烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)烯氧基-(C1-C4)烷基、(C2-C4)卤代烯氧基-(C1-C4)烷基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)炔氧基-(C1-C4)烷基、(C2-C4)卤代炔氧基-(C1-C4)烷基、(C2-C4)卤代炔基、(C2-C4)氰基炔基、(C3-C6)环烷基、(C3-C6)环烷基(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、(C1-C4)烷基氨基、二-(C1-C4)烷基氨基、(C3-C6)环烷基氨基、(C1-C4)烷基羰基氨基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)卤代烷硫基-(C1-C4)烷基、(C1-C4)烷基亚磺酰基-(C1-C4)烷基、(C1-C4)卤代烷基亚磺酰基-(C1-C4)烷基、(C1-C4)烷基磺酰基-(C1-C4)烷基、(C1-C4)烷基羰基-(C1-C4)烷基、(C1-C4)卤代烷基羰基-(C1-C4)烷基、(C1-C4)烷基磺酰基氨基,
R8、R9、R10、R11、R12、R13、R14、R15独立地为氢、氰基、卤素、硝基、乙酰基、羟基、氨基、SCN、三-(C1-C4)烷基甲硅烷基、(C3-C6)环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、氰基-(C3-C6)-环烷基、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C1-C4)羟基烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C2-C4)氰基炔基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C1-C4)氰基烷氧基、(C1-C4)烷氧基-(C1-C4)烷氧基、(C1-C4)烷基羟基亚氨基、(C1-C4)烷氧基亚氨基、(C1-C4)烷基-(C1-C4)烷氧基亚氨基、(C1-C4)卤代烷基-(C1-C4)烷氧基亚氨基、(C1-C4)烷硫基、(C1-C4)卤代烷硫基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)烷基亚磺酰基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)烷基亚磺酰基-(C1-C4)烷基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、(C1-C4)烷基磺酰基-(C1-C4)烷基、(C1-C4)烷基磺酰氧基、(C1-C4)烷基羰基、(C1-C4)卤代烷基羰基、氨基羰基、(C1-C4)烷基氨基羰基、二-(C1-C4)烷基氨基羰基、(C1-C4)烷基磺酰基氨基、(C1-C4)烷基氨基、二-(C1-C4)烷基氨基、氨基磺酰基、(C1-C4)烷基氨基磺酰基、二-(C1-C4)烷基氨基磺酰基、氨基硫代羰基、NHCO-(C1-C4)烷基((C1-C4)烷基羰基氨基),以及为苯基或杂芳基,其各自任选地被相同或不同地单取代或双取代,其中(在杂芳基的情况下)可任选地存在至少一个羰基和/或其中在每种情况下的可能的取代基如下:氰基、卤素、硝基、乙酰基、氨基、(C3-C6)环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C1-C4)羟基烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C2-C4)氰基炔基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C1-C4)氰基烷氧基、(C1-C4)烷氧基-(C1-C4)烷氧基、(C1-C4)烷基羟基亚氨基、(C1-C4)烷氧基亚氨基、(C1-C4)烷基-(C1-C4)烷氧基亚氨基、(C1-C4)卤代烷基-(C1-C4)烷氧基亚氨基、(C1-C4)烷硫基、(C1-C4)卤代烷硫基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)烷基亚磺酰基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)烷基亚磺酰基-(C1-C4)烷基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、(C1-C4)烷基磺酰基-(C1-C4)烷基、(C1-C4)烷基磺酰氧基、(C1-C4)烷基羰基、(C1-C4)卤代烷基羰基、氨基羰基、(C1-C4)烷基氨基羰基、二-(C1-C4)烷基氨基羰基、(C1-C4)烷基磺酰基氨基、(C1-C4)烷基氨基、二-(C1-C4)烷基氨基、氨基磺酰基、(C1-C4)烷基氨基磺酰基、二-(C1-C4)烷基氨基磺酰基、NHCO-(C1-C4)烷基((C1-C4)烷基羰基氨基),
Q为杂芳族的8、9、10、11或12元的稠合双环或三环的环体系,其中可任选地存在至少一个羰基和/或其中所述环体系任选地被相同或不同地单取代或多取代,并且其中所述取代基可独立地选自:氰基、卤素、硝基、乙酰基、羟基、氨基、SCN、三-(C1-C6)-烷基甲硅烷基、(C3-C8)-环烷基、氰基-(C3-C8)-环烷基、(C3-C8)-环烷基-(C3-C8)-环烷基、(C1-C6)-烷基-(C3-C8)-环烷基、卤代-(C3-C8)-环烷基、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-氰基烷基、(C1-C6)-羟基烷基、(C1-C6)-烷氧基-(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-卤代烯基、(C2-C6)-氰基烯基、(C2-C6)-炔基、(C2-C6)-炔氧基-(C1-C4)-烷基、(C2-C6)-卤代炔基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-卤代烷氧基-(C1-C6)-烷基、(C2-C6)-烯氧基-(C1-C6)-烷基、(C2-C6)-卤代烯氧基-(C1-C6)-烷基、(C1-C6)-氰基烷氧基、(C1-C6)-烷氧基-(C1-C6)-烷氧基、(C1-C6)-烷基羟基亚氨基、(C1-C6)-烷氧基亚氨基、(C1-C6)-烷基-(C1-C6)-烷氧基亚氨基、(C1-C6)-烷硫基、(C1-C6)-卤代烷硫基、(C1-C6)-烷氧基-(C1-C6)-烷硫基、(C1-C6)-烷硫基-(C1-C6)-烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基亚磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰基、(C1-C6)-卤代烷基磺酰基、(C1-C6)-烷氧基-(C1-C6)-烷基磺酰基、(C1-C6)-烷基磺酰基-(C1-C6)-烷基、(C1-C6)-烷基磺酰氧基、(C1-C6)-烷基羰基、(C1-C6)-烷基羰基-(C1-C6)-烷基、(C1-C6)-烷硫基羰基、(C1-C6)-卤代烷基羰基、(C1-C6)-烷基羰基氧基、(C1-C6)-烷氧基羰基、(C1-C6)-卤代烷氧基羰基、氨基羰基、(C1-C6)-烷基氨基羰基、(C1-C6)-烷基氨基硫代羰基、二-(C1-C6)-烷基氨基羰基、二-(C1-C6)-烷基氨基硫代羰基、(C3-C8)-环烷基氨基羰基、(C1-C6)-烷基磺酰基氨基、(C1-C6)-烷基氨基、二-(C1-C6)-烷基氨基、氨基磺酰基、(C1-C6)-烷基氨基磺酰基、二-(C1-C6)-烷基氨基磺酰基、(C1-C6)-烷基亚砜亚胺基、氨基硫代羰基、(C1-C6)-烷基氨基硫代羰基、二-(C1-C6)-烷基氨基硫代羰基、(C3-C8)-环烷基氨基、NHCO-(C1-C6)-烷基((C1-C6)-烷基羰基氨基),
或其中所述取代基可独立地选自苯基或5或6元杂芳族环,其中所述苯基或所述环可任选地被以下基团相同或不同地单取代或多取代:C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C6-环烷基、C1-C6-卤代烷基、C2-C6-卤代烯基、C2-C6-卤代炔基、C3-C6-卤代环烷基、卤素、CN、C1-C4-烷氧基、C1-C4-卤代烷氧基,
n为0、1或2。
3.根据权利要求1的式(I)的化合物,其中
Aa为–C(R8)(R9)-,
Ab为–C(R10)(R11)-,
Ac为–C(R12)(R13)-,
Ad为–C(R14)(R15)-,
R1为(C1-C4)烷基、(C1-C4)羟基烷基、(C1-C4)卤代烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C3-C6)环烷基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)烷基亚磺酰基-(C1-C4)烷基或(C1-C4)烷基磺酰基-(C1-C4)烷基,
R8、R9、R10、R11、R12、R13、R14、R15独立地为氢、氰基、卤素、硝基、羟基、氨基、SCN、三-(C1-C4)烷基甲硅烷基、(C3-C6)环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、氰基-(C3-C8)环烷基、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C2-C4)氰基炔基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C1-C4)氰基烷氧基、(C1-C4)烷基羟基亚氨基、(C1-C4)烷氧基亚氨基、(C1-C4)烷基-(C1-C4)烷氧基亚氨基、(C1-C4)烷硫基、(C1-C4)卤代烷硫基、(C1-C4)烷基亚磺酰基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、(C1-C4)烷基磺酰氧基、(C1-C4)烷基羰基、(C1-C4)卤代烷基羰基、氨基羰基、(C1-C4)烷基氨基羰基、二-(C1-C4)烷基氨基羰基、(C1-C4)烷基磺酰基氨基、(C1-C4)烷基氨基、二-(C1-C4)烷基氨基、氨基磺酰基、(C1-C4)烷基氨基磺酰基、二-(C1-C4)烷基氨基磺酰基、NHCO-(C1-C4)烷基((C1-C4)烷基羰基氨基),
以及苯基或杂芳基,其各自任选地被相同或不同地单取代或双取代,其中(在杂芳基的情况下)可任选地存在至少一个羰基和/或其中在每种情况下可能的取代基如下:氰基、卤素、(C3-C6)环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C2-C4)氰基炔基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C1-C4)烷基羟基亚氨基、(C1-C4)烷氧基亚氨基、(C1-C4)烷基-(C1-C4)烷氧基亚氨基、(C1-C4)烷硫基、(C1-C4)卤代烷硫基、(C1-C4)烷基亚磺酰基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、(C1-C4)烷基磺酰氧基、(C1-C4)烷基羰基、(C1-C4)卤代烷基羰基、氨基羰基、(C1-C4)烷基氨基羰基、二-(C1-C4)烷基氨基羰基、(C1-C4)烷基磺酰基氨基、(C1-C4)烷基氨基、二-(C1-C4)烷基氨基、氨基磺酰基、(C1-C4)烷基氨基磺酰基、二-(C1-C4)烷基氨基磺酰基、NHCO-(C1-C4)烷基((C1-C4)烷基羰基氨基),
Q为选自Q1至Q21的杂芳族的9元或12元的稠合双环或三环的环体系:
R4为(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-氰基烷基、(C1-C4)-羟基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-卤代烷氧基-(C1-C4)-烷基、(C2-C4)-烯基、(C2-C4)-烯氧基-(C1-C4)-烷基、(C2-C4)-卤代烯氧基-(C1-C4)-烷基、(C2-C4)-卤代烯基、(C2-C4)氰基烯基、(C2-C4)-炔基、(C2-C4)-炔氧基-(C1-C4)-烷基、(C2-C4)-卤代炔基、(C3-C6)-环烷基、(C3-C6)-环烷基-(C3-C6)-环烷基、(C1-C4)-烷基-(C3-C6)-环烷基、卤代-(C3-C6)-环烷基、(C1-C4)-烷硫基-(C1-C4)-烷基、(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基、(C1-C4)-烷基磺酰基-(C1-C4)-烷基或(C1-C4)-烷基羰基-(C1-C4)-烷基,
R5、R6独立地为氢、氰基、卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C2-C4)-烯基、(C2-C4)-卤代烯基、(C2-C4)-炔基、(C2-C4)-卤代炔基、(C3-C6)-环烷基、氰基-(C3-C6)-环烷基、(C3-C6)-环烷基-(C3-C6)-环烷基、(C1-C4)-烷基-(C3-C6)-环烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷氧基亚氨基、(C1-C4)-烷硫基、(C1-C4)-卤代烷硫基、(C1-C4)-烷基亚磺酰基、(C1-C4)-卤代烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C1-C4)-卤代烷基磺酰基、(C1-C4)-烷基磺酰氧基、(C1-C4)-烷基羰基、(C1-C4)-卤代烷基羰基、氨基羰基、(C1-C4)-烷基氨基羰基、二-(C1-C4)-烷基氨基羰基、(C1-C4)-烷基磺酰基氨基、(C1-C4)-烷基氨基、二-(C1-C4)-烷基氨基、氨基磺酰基、(C1-C4)-烷基氨基磺酰基或二-(C1-C4)-烷基氨基磺酰基,
R7为氢、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C1-C4)羟基烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C1-C4)卤代烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)烯氧基-(C1-C4)烷基、(C2-C4)卤代烯氧基-(C1-C4)烷基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C3-C6)环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)烷基亚磺酰基-(C1-C4)烷基或(C1-C4)烷基磺酰基-(C1-C4)烷基,
n为0、1或2。
4.根据权利要求1的式(I)的化合物,其中
Aa为–C(R8)(R9)-,
Ab为–C(R10)(R11)-,
Ac为–C(R12)(R13)-,
Ad为–C(R14)(R15)-,
R1为甲基、乙基、正丙基、异丙基、环丙基、正丁基、异丁基、叔丁基、环丁基、氟甲基、二氟甲基、三氟甲基、氟乙基、二氟乙基、三氟乙基、四氟乙基或五氟乙基,
R8、R9、R10、R11、R12、R13、R14、R15独立地为氢、氰基、卤素、(C1-C4)烷基、(C3-C6)-环烷基、氰基-(C3-C6)-环烷基、(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)烷基亚磺酰基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷硫基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)卤代烷基磺酰基或NHCO-(C1-C4)烷基((C1-C4)烷基羰基氨基),
Q为选自以下的杂芳族的9元或12元的稠合双环或三环的环体系:Q2、Q3、Q4、Q10、Q11、Q14、Q15、Q16、Q19、Q20或Q21,
R4为(C1-C4)-烷基或(C1-C4)-烷氧基-(C1-C4)-烷基,
R5为氢、氰基、卤素、(C1-C4)烷基、(C1-C4)卤代烷基、(C3-C6)环烷基、氰基-(C3-C6)-环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、(C1-C4)烷氧基、(C1-C4)卤代烷氧基、(C1-C4)烷氧基亚氨基、(C1-C4)烷硫基、(C1-C4)卤代烷硫基、(C1-C4)烷基亚磺酰基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、(C1-C4)烷基羰基、(C1-C4)卤代烷基羰基、(C1-C4)烷基氨基羰基、二-(C1-C4)烷基氨基羰基、(C1-C4)烷基磺酰基氨基、(C1-C4)烷基氨基磺酰基或二-(C1-C4)烷基氨基磺酰基,
R6为氢或甲基,
R7为氢、(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)氰基烷基、(C1-C4)烷氧基-(C1-C4)烷基、(C1-C4)卤代烷氧基-(C1-C4)烷基、(C2-C4)烯基、(C2-C4)卤代烯基、(C2-C4)氰基烯基、(C2-C4)炔基、(C2-C4)卤代炔基、(C3-C6)环烷基、(C3-C6)环烷基-(C3-C6)环烷基、(C1-C4)烷基-(C3-C6)环烷基、卤代(C3-C6)环烷基、(C1-C4)烷硫基-(C1-C4)烷基、(C1-C4)烷基亚磺酰基-(C1-C4)烷基或(C1-C4)烷基磺酰基-(C1-C4)烷基,
n为0、1或2。
5.根据权利要求1的式(I)的化合物,其中
Aa为–C(R8)(R9)-,
Ab为–C(R10)(R11)-,
Ac为–C(R12)(R13)-,
Ad为–C(R14)(R15)-,
R1为甲基、乙基、正丙基、异丙基或环丙基,
R8、R9、R10、R11、R12、R13、R14、R15独立地为氢、氰基、环丙基、环丁基、氰基环丙基、氟、氯、溴、甲基、乙基、三氟甲基、二氟甲基、三氟乙基、甲氧基或乙氧基,
Q为选自以下的杂芳族的9元的稠合双环的环体系:Q2、Q3、Q4、Q10、Q14、Q16或Q21,
R4为甲基、乙基、异丙基、甲氧基甲基或甲氧基乙基,
R5为氟、氯、溴、氟甲基、二氟甲基、三氟甲基、氟乙基(CH2CFH2、CHFCH3)、二氟乙基(CF2CH3、CH2CHF2、CHFCFH2)、三氟乙基(CH2CF3、CHFCHF2、CF2CFH2)、四氟乙基(CHFCF3、CF2CHF2)、五氟乙基、三氟甲氧基、二氟氯甲氧基、二氯氟甲氧基、三氟甲硫基、三氟甲基亚磺酰基、三氟甲基磺酰基或氰基环丙基,
R6为氢,
R7为甲基、乙基、异丙基、环丙基、甲氧基甲基或甲氧基乙基,
n为0、1或2。
6.根据权利要求1的式(I)的化合物,其中
Aa为–C(R8)(R9)-,
Ab为–C(R10)(R11)-,
Ac为–C(R12)(R13)-,
Ad为–C(R14)(R15)-,
R1为乙基,
R8为氢,
R9为氢,
R10为氢、甲基或三氟甲基,
R11为氢,
R12为氢、甲基或三氟甲基,
R13为氢,
R14为氢,
R15为氢,
Q为选自Q2、Q3、Q4或Q21的杂芳族的9元稠合的双环环体系,
R4为甲基,
R5为三氟甲基、五氟乙基、三氟甲氧基、三氟甲硫基、三氟甲基亚磺酰基或三氟甲基磺酰基,
R6为氢,
R7为甲基,
n为2。
8.农用化学制剂,其包含根据权利要求1的式(I)的化合物以及增量剂和/或表面活性剂。
9.根据权利要求8的农用化学制剂,另外包含其他农用化学活性成分。
10.防治动物害虫的方法,其特征在于将根据权利要求1的式(I)的化合物或根据权利要求8或9的农用化学制剂作用于动物害虫和/或其生境。
11.根据权利要求1的式(I)的化合物或根据权利要求8或9的农用化学制剂用于防治动物害虫的用途。
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ES2906077T3 (es) | 2022-04-13 |
TW201945363A (zh) | 2019-12-01 |
EP3755700B1 (de) | 2021-11-24 |
WO2019162174A1 (de) | 2019-08-29 |
EP3755700A1 (de) | 2020-12-30 |
KR20200122353A (ko) | 2020-10-27 |
BR112020016926B1 (pt) | 2022-08-30 |
AR114330A1 (es) | 2020-08-19 |
US11019821B2 (en) | 2021-06-01 |
JP2021514949A (ja) | 2021-06-17 |
BR112020016926A2 (pt) | 2020-12-15 |
US20200383334A1 (en) | 2020-12-10 |
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