CN117083266A - 杀微生物的异烟酰胺衍生物 - Google Patents
杀微生物的异烟酰胺衍生物 Download PDFInfo
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- CN117083266A CN117083266A CN202280024757.7A CN202280024757A CN117083266A CN 117083266 A CN117083266 A CN 117083266A CN 202280024757 A CN202280024757 A CN 202280024757A CN 117083266 A CN117083266 A CN 117083266A
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Abstract
披露了具有式(I)的化合物,其中取代基是如权利要求1所定义的,这些化合物可用作杀有害生物剂、尤其可用作杀真菌剂。
Description
本发明涉及异烟酰胺衍生物,例如作为活性成分,这些异烟酰胺衍生物具有杀微生物活性、特别是杀真菌活性。本发明还涉及包含这些异烟酰胺衍生物中的至少一种的农用化学组合物,这些化合物的制备方法,以及这些异烟酰胺衍生物或组合物在农业或园艺中用于控制或预防植物、收获的粮食作物、种子或非生命材料被植物病原性微生物、优选真菌侵染的用途。
WO 2020/109391披露了哒嗪(硫代)酰胺衍生物用于控制植物病原性微生物的用途。WO 2021/224220披露了吡啶(硫代)酰胺作为杀真菌化合物的用途。JP 2001 294563披露了具有杀菌和除草活性的水杨酸酰胺。WO 2017/012966披露了可用于增加植物对非生物胁迫的胁迫耐受性的酰肼。
根据本发明,提供了一种具有式(I)的化合物:
其中:
L1是-O-或-CH2-或键;
R1选自氢、卤素、氰基、C1-C3-烷基或C1-C3-烷氧基;
R2选自氢、氰基、烷基硫基(mercaptyl)、卤素、C1-C3-烷基、C2-C4-烯基(如C2-C3-烯基)、C2-C3-炔基、C1-C3-烷氧基、C1-C3-氟烷基、C1-C3-氟烷氧基、C3-C4-环烷基或C1-C3-烷基磺酰基;
R3选自氢、卤素、氰基、甲基、C1-C4-烷基、C1-C3-氟烷基、C2-C4-烯基、C2-C4-炔基、C1-C4-烷氧基、C2-C4-烯氧基、C2-C5-炔氧基、C1-C3-氟烷氧基、C3-C4-环烷基;或者
R3是任选地被1或2个取代基取代的苯氧基,所述取代基独立地选自卤素、氰基、甲基、乙基、二氟甲基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、环丙基,
R4和R5独立地选自氢、氰基或甲基;或者
R4和R5与它们所附接的碳原子一起形成环丙基或环丁基;
R6和R7独立地选自氢、氟、氯、甲基、三氟甲基、羟基、甲氧基、甲氧基甲基、二氟甲氧基、烷基硫基、甲基硫烷基;或者
R6和R7与它们所附接的碳原子一起形成氧代基、环丙基或环丁基、或4元至6元单环杂环基团,所述单环杂环基团包含单独选自N、O和S的1或2个杂原子;或者
R4和R6与它们所附接的碳原子一起形成C3-C4-环烷基或4元至6元单环杂环基团,所述单环杂环基团包含单独选自N、O和S的1或2个杂原子,并且R5和R7独立地是氢或卤素;
R8是任选地被以下取代的苯基:
单个取代基,其选自C1-C4-烷基、C1-C2-卤代烷基、C1-C3-烷氧基、C1-C3-烷基硫烷基、C1-C3-烷基磺酰基、C1-C2-卤代烷氧基、C2-C3-烯基、C2-C3-卤代烯基、C2-C3-炔基、C3-C4-环烷基、C3-C4-环烷氧基或-NH(COC1-C3-烷基),或者
可以相同或不同的1、2或3个取代基,所述取代基独立地选自羟基、卤素、巯基、氨基、氰基、甲基、乙基、丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、甲基硫烷基、甲基磺酰基、二氟甲氧基、三氟甲氧基、环丙基、环丁基、环丙氧基、-NH(COCH3);并且
R9是任选地被以下取代的苯基:
单个取代基,其选自C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基、C1-C3-烷基硫烷基、C1-C3-烷基磺酰基、C1-C2-卤代烷氧基、C2-C3-烯基、C2-C3-卤代烯基、C2-C3-炔基、C3-C4-环烷基、C3-C4-环烷氧基;或者
可以相同或不同的1、2或3个取代基,所述取代基独立地选自羟基、卤素、巯基、氨基、氰基、甲基、乙基、丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、丙炔氧基(propynoxy)、甲基硫烷基、甲基磺酰基、二氟甲氧基、三氟甲氧基、环丙基、环丁基、环丙氧基、-NH(COCH3);或者
或其盐或N-氧化物。
出人意料地,已经发现,出于实际目的,新颖的具有式(I)的化合物具有非常有利水平的用来保护植物对抗由真菌引起的病害的生物活性。
根据本发明的第二方面,提供了一种包含杀真菌有效量的具有式(I)的化合物的农用化学组合物。此种农业组合物可以进一步包含至少一种另外的活性成分和/或农用化学上可接受的稀释剂或载体。
根据本发明的第三方面,提供了一种控制或预防有用植物被植物病原性微生物侵染的方法,其中将杀真菌有效量的具有式(I)的化合物、或包含此化合物作为活性成分的组合物施用至这些植物、其部分或其场所。
根据本发明的第四方面,提供了具有式(I)的化合物作为杀真菌剂的用途。根据本发明的这个特定方面,该用途可以不包括通过手术或疗法来治疗人体或动物体的方法。
如本文使用的,术语“羟基(hydroxyl)”或“羟基(hydroxy)”意指-OH基团。
如本文使用的,术语“巯基”意指-SH基团。
如本文使用的,术语“氰基”意指-CN基团。
如本文使用的,氨基意指-NH2基团。
如本文使用的,硝基意指-NO2基团。
如本文使用的,氧代意指=O基团(例如,如在羰基(C=O)基团中)。
如本文使用的,术语“卤素(halogen或halo)”是指氟(fluorine,fluoro)、氯(chlorine,chloro)、溴(bromine,bromo)或碘(iodine,iodo),优选氟、氯或溴。
如本文使用的,术语“C1-4烷基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,该烃链基团不含不饱和度,具有从一至四个碳原子,并且通过单键附接至分子的其余部分。C1-3烷基应相应地解释。C1-4烷基的实例包括但不限于甲基、乙基、异丙基。
如本文使用的,术语“C2-3烯基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,该烃链基团含有至少一个可以具有(E)或(Z)构型的双键,具有两个或三个碳原子,通过单键附接至分子的其余部分。C2-3烯基的实例包括但不限于丙-1-烯基、烯丙基(丙-2-烯基)。
如本文使用的,术语“C2-3卤代烯基”是指被一个或多个相同的或不同的卤素原子取代的如上定义的C2-3烯基。
如本文使用的,术语“C2-3炔基”是指仅由碳原子和氢原子组成的直链或支链的烃链基团,该烃链基团含有至少一个三键,具有两个或三个碳原子,并且通过单键附接至分子的其余部分。C2-3炔基的实例包括但不限于丙-1-炔基和炔丙基(丙-2-炔基)。
如本文使用的,术语“C1-3烷氧基”是指具有式RaO-的基团,其中Ra是如上一般定义的C1-3烷基。C1-3烷氧基的实例包括但不限于甲氧基、乙氧基、异丙氧基。
如本文使用的,术语“C1-4卤代烷基”是指被一个或多个相同的或不同的卤素原子取代的如上一般定义的C1-4烷基。C1-4卤代烷基的实例包括但不限于氟甲基、氟乙基、二氟甲基、三氟甲基、和2,2,2-三氟乙基。
如本文使用的,术语“C1-3氟烷基”是指被一个或多个氟原子取代的如上一般定义的C1-3烷基。C1-3氟烷基的实例包括但不限于二氟甲基和三氟甲基。
如本文使用的,术语“C1-3氟烷氧基”是指被一个或多个氟原子取代的如上一般定义的C1-3烷氧基。C1-3氟烷氧基的实例包括但不限于三氟甲氧基。
如本文使用的,术语“C3-4环烷基”是指饱和且含有3或4个碳原子的稳定的单环基团。
如本文使用的,术语“C1-3烷基硫烷基”是指具有式-SRa的基团,其中Ra是如上一般定义的C1-3烷基。
如本文使用的,术语“C1-3烷基磺酰基”是指具有式-S(O)2Ra的基团,其中Ra是如上一般定义的C1-3烷基。
在具有式(I)的化合物中一个或多个可能的不对称碳原子的存在意味着所述化合物能以手性异构体形式存在,即对映异构体或非对映异构体的形式。作为围绕单键的受限旋转的结果,还可能存在阻转异构体。式(I)旨在包括所有那些可能的异构体形式及其混合物。本发明包括具有式(I)的化合物的所有那些可能的异构形式及其混合物。同样地,式(I)旨在包括所有可能的互变异构体(包括内酰胺-内酰亚胺互变异构和酮-烯醇互变异构)(当存在时)。本发明包括具有式(I)的化合物的所有可能的互变异构体形式。
在每种情况下,根据本发明的具有式(I)的所述化合物是呈游离形式、氧化形式(作为N-氧化物)、共价水合形式、或盐形式(如农艺学上可用的或农用化学上可接受的盐形式)。
N-氧化物是叔胺的氧化形式或含氮杂芳香族化合物的氧化形式。例如,A.Albini和S.Pietra于1991年在博卡拉顿(Boca Raton)CRC出版社出版的名为“Heterocyclic N-oxides[杂环N-氧化物]”一书中描述了它们。
以下清单提供了关于本发明的具有式(I)的化合物的取代基L1、R1、R2、R3、R4、R5、R6、R7、R8和R9的定义,包括优选的定义。对于这些取代基中的任何一个,以下给出的任何定义都可以结合以下或在本文件中的其他地方给出的任何其他取代基的任何定义。
L1是-O-或-CH2-或键。在本发明的某些实施例中,L1是-O-。在本发明的某些实施例中,L1是-CH2-。在本发明的某些实施例中,L1是键。
R1选自氢、卤素、氰基、C1-C3-烷基或C1-C3-烷氧基。优选地,R1是氢、氯、甲基或甲氧基。最优选地,R1是氢。在本发明的实施例中,R1选自C1-C3-烷基或C1-C3-烷氧基,如甲基或甲氧基。
R2选自氢、氰基、烷基硫基、卤素、C1-C3-烷基、C2-C3-烯基、C2-C3-炔基、C1-C3-烷氧基、C1-C3-氟烷基、C1-C3-氟烷氧基、C3-C4-环烷基或C1-C3-烷基磺酰基。R2还可以选自氢、氰基、烷基硫基、卤素、C1-C3-烷基、C1-C3-烷氧基、C1-C3-氟烷基、C1-C3-氟烷氧基、C3-C4-环烷基或C1-C3-烷基磺酰基。优选地,R2是氢、氰基、烷基硫基、卤素、甲基、甲氧基、三氟甲基、环丙基或甲基磺酰基。最优选地,R2是氢、氯或甲基。在本发明的实施例中,R2是C1-C3-氟烷氧基。
R3选自氢、卤素、甲基、甲氧基、或氰基。优选地,R3是氢、氟、氯、溴、甲氧基或氰基。最优选地,R3是氢。R3还可以是氢、卤素、氰基、甲基、C1-C4-烷基、C1-C3-氟烷基、C2-C4-烯基、C2-C4-炔基、C1-C4-烷氧基、C2-C4-烯氧基、C2-C5-炔氧基、C1-C3-氟烷氧基、C3-C4-环烷基。该C1-C4-烷基、C1-C3-氟烷基、C2-C4-烯基、C2-C4-炔基、C1-C4-烷氧基、C2-C4-烯氧基、C2-C5-炔氧基、和C1-C3-氟烷氧基可以是直链或支链的。
R3还可以是苯氧基或被一个或两个取代基取代的苯氧基,该取代基独立地选自卤素、巯基、氨基、氰基、甲基、乙基、丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基,R3还可以是苯氧基或被一个取代基取代的苯氧基,该取代基选自卤素、巯基、氨基、氰基、甲基、乙基、丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基。
R4和R5独立地选自氢、氰基或甲基。优选地,R4和R5是氢。另外,R4和R5独立地选自氢和氰基。另外,R4和R5与它们所附接的碳原子一起形成环丙基或环丁基。
R6和R7独立地选自氢、氟、氯、甲基、三氟甲基、羟基、甲氧基、甲氧基甲基、二氟甲氧基、烷基硫基、甲基硫烷基。优选地,R6是氢、氟、甲基或甲氧基,并且R7是氢或氟。最优选地,R6是氢或氟,并且R7是氢或氟。另外,R6和R7与它们所附接的碳原子一起形成氧代基、环丙基或环丁基、或4元至6元单环杂环基团,该单环杂环基团包含单独选自N、O和S的1或2个杂原子,优选地R6和R7与它们所附接的碳原子一起形成环丙基、或环丁基。
R4和R6可以与它们所附接的碳原子一起形成C3-C4-环烷基(如环丙基)、或4元至6元单环杂环基团,该单环杂环基团包含单独选自N、O和S的1或2个杂原子,并且R5和R7独立地是氢或卤素。
R8是任选地被以下取代的苯基:
(a)单个取代基,其选自C1-C4-烷基、C1-C2-卤代烷基、C1-C3-烷氧基、C1-C3-烷基硫烷基、C1-C3-烷基磺酰基、C1-C2-卤代烷氧基、C2-C3-烯基、C2-C3-卤代烯基、C2-C3-炔基、C3-C4-环烷基、C3-C4-环烷氧基或-NH(COC1-C3-烷基);或者
(b)可以相同或不同的1、2或3个取代基,该取代基独立地选自羟基、卤素、巯基、氨基、氰基、甲基、乙基、丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、甲基硫烷基、甲基磺酰基、二氟甲氧基、三氟甲氧基、环丙基、环丁基、环丙氧基、-NH(COCH3)。
优选地,R8是任选地如以上对于(b)所定义的取代的苯基,其中可以有1或2个相同或不同的取代基。更优选地,R8是任选地被1或2个取代基取代的苯基,该取代基独立地选自羟基、卤素、氰基、甲基、乙基、二氟甲基、三氟甲基、甲氧基或乙氧基。最优选地,R8是任选地被1或2个取代基取代的苯基,该取代基独立地选自卤素、特别是氯,例如,R8是2,4-二氯苯基。
R9是任选地被以下取代的苯基:
单个取代基,其选自C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基、C1-C3-烷基硫烷基、C1-C3-烷基磺酰基、C1-C2-卤代烷氧基、C2-C3-烯基、C2-C3-卤代烯基、C2-C3-炔基、C3-C4-环烷基、C3-C4-环烷氧基;或者
可以相同或不同的1、2或3个取代基,该取代基独立地选自羟基、卤素、巯基、氨基、氰基、甲基、乙基、丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、甲基硫烷基、甲基磺酰基、二氟甲氧基、三氟甲氧基、环丙基、环丁基、环丙氧基、-NH(COCH3)。
优选地,R9是任选地被1或2个取代基取代的苯基,该取代基独立地选自羟基、卤素、巯基、氨基、氰基、甲基、乙基、丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、丙炔氧基、甲基硫烷基、甲基磺酰基、二氟甲氧基、三氟甲氧基、环丙基、环丁基、环氧丙基和-NH(COCH3)。
更优选地,R9是任选地被1或2个取代基取代的苯基,该取代基独立地选自卤素、氰基、甲基、乙基、二氟甲基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、丙炔氧基、甲基硫烷基、二氟甲氧基、三氟甲氧基、环丙基和-NH(COCH3)。甚至更优选地,R9是任选地被甲基、三氟甲基或环丙基取代(特别是在3位)的苯基。最优选地,R9是被甲基或环丙基取代的苯基,例如,3-甲基苯基或3-环丙基苯基。
优选地,根据式(I)的化合物选自在表T1(下文)中列出的化合物1.1至1.98;例如在表T1(下文)中列出的化合物1.1至1.88;如选自在表T1(下文)中列出的化合物1.1、1.2、1.4、1.5、1.6、1.7、1.8、1.9、1.10、1.11、1.12、1.13、1.14、1.15、1.17、1.18、1.19、1.20、1.21、1.22、1.23、1.24、1.25、1.26、1.27、1.28、1.29、1.30、1.31、1.32、1.33、1.34、1.35、1.36、1.37、1.38、1.39、1.40、1.43、1.44、1.45、1.46、1.47、1.48、1.49、1.50、1.51、1.52、1.53、1.54、1.55、1.56、1.57、1.58、1.59、1.62、1.63、1.64、1.65、1.66、1.67、1.68、1.69、1.71、1.72、1.73、1.74、1.75、1.78、1.79、1.80、1.81、1.82、1.83、1.84、1.85、1.86、1.87、1.88、1.89、1.90、1.91、1.92、1.93、1.94、1.95、1.96、1.97、1.98的化合物。例如,根据式(I)的化合物是在表T1(下文)中列出的化合物1.1或化合物1.22。
本发明的化合物可以是具有式(I)的化合物的对映异构体,如式(I-1)或式(I-2)或式(I-3)或式(I-4)所示的,其中R4和R5是不同的取代基和/或其中R6和R7是不同的取代基。
除非另外说明,否则根据本发明的具有式(I)的化合物可以如以下方案1至13中所示制备,其中L1、R1、R2、R3、R4、R5、R6、R7、R8和R9是如对于具有式(I)的化合物所定义的。
具有式(I)的化合物通过以下方式获得:具有式(II)的化合物(其中X是OH)和具有式(III)的胺化合物通过活化具有式(II)的化合物的羧酸官能团的酰胺偶联转化,其是通常通过以下方式而发生的过程:将羧酸的-OH转化为良好的离去基团如氯化物基团,例如通过使用(COCl)2或SOCl2,然后优选地在合适的溶剂(例如,N-甲基吡咯烷酮、乙腈、二甲基乙酰胺、二氯甲烷或四氢呋喃)中,优选地在25℃与60℃之间的温度下,并且任选地在碱(如三乙胺或N,N-二异丙基乙胺)的存在下;或可替代地在文献中针对酰胺偶联描述的条件(如1-丙烷膦酸环酐(T3P))下,在合适的溶剂(例如,乙腈)中,任选地在碱(例如,三乙胺或N,N-二异丙基乙胺)的存在下用具有式(III)的化合物处理。例如,参见Chem.Soc.Rev.[化学学会综述](2009),38,606和Chem.Soc.Rev.[化学学会综述](2011),40,5084。具有式(II)的化合物和具有式(III)的化合物是已知的或可商购的。这示于方案1中。
方案1
具有式(I)的化合物通过以下方式制备:使亲核的具有式(IV)的化合物与亲电的具有式(V)的化合物(其中Y是合适的离去基团,如氟、氯、溴、碘、BF3K、B(OH)2或B(频哪醇)),在碱(例如,KO-t-Bu、K3PO4、K2CO3、三乙胺、或Cs2CO3)的存在下,在合适的溶剂(例如,N-甲基吡咯烷酮、二甲基乙酰胺、乙腈、四氢呋喃、2-甲基四氢呋喃、环丁砜、或二甲基亚砜)中,在60℃与110℃之间的温度下,并且优选使用金属催化剂络合物(例如,Cu或Pd)进行反应。对于相关实例,参见Eur.J.Org.Chem.[欧洲有机化学杂志],(2011),18,3353;J.Org.Chem.[有机化学杂志],(2009),74,7951;Tetrahedron Lett.[四面体快报],(2012),53,5318。具有式(IV)的化合物是已知的或可商购的。这示于方案2中。
方案2
具有式(II)的化合物(其中X是C1-C4-烷氧基)通过以下方式制备:使亲核的具有式(IV)的化合物与亲电的具有式(VI)的化合物(其中X是OH或C1-C4-烷氧基,并且Y是合适的离去基团,如氟、氯、溴、碘、BF3K、B(OH)2或B(频哪醇)),在碱(例如,KO-t-Bu、K3PO4、K2CO3、三乙胺、或Cs2CO3)的存在下,在合适的溶剂(例如,N-甲基吡咯烷酮、二甲基乙酰胺、乙腈、四氢呋喃、2-甲基四氢呋喃、环丁砜、二甲基亚砜)中,在60℃与110℃之间的温度下,并且优选使用金属催化剂络合物(例如,Cu或Pd)进行反应。对于相关实例,参见Eur.J.Org.Chem.[欧洲有机化学杂志],(2011),18,3353;J.Org.Chem.[有机化学杂志],(2009),74,7951;Tetrahedron Lett.[四面体快报],(2012),53,5318;WO 2008/110313和WO 2012/136604。此外,具有式(II)的化合物,其中X=C1-C4-烷氧基,容易在文献中描述的条件下水解,以得到具有式(II)的化合物,其中X是OH。具有式(VI)的化合物是已知的或可商购的。这示于方案3中。
方案3
具有式(V)的化合物(其中Y是卤素或OH)可以通过以下方式获得:具有式(VI)的化合物(其中X是OH,并且Y是卤素或OH)和具有式(III)的胺化合物通过活化具有式(VI)的化合物的羧酸官能团的酰胺偶联转化,其是通常通过以下方式而发生的过程:将羧酸的-OH转化为良好的离去基团如氯化物基团,例如通过使用(COCl)2或SOCl2,然后优选地在合适的溶剂(例如,N-甲基吡咯烷酮、二甲基乙酰胺、二氯甲烷或四氢呋喃)中,优选地在25℃与60℃之间的温度下,并且任选地在碱(如三乙胺或N,N-二异丙基乙胺)的存在下;或可替代地在文献中针对酰胺偶联描述的条件(如1-丙烷膦酸环酐(T3P))下,在合适的溶剂(例如,乙腈)中,任选地在碱(例如,三乙胺或N,N-二异丙基乙胺)的存在下用具有式(III)的化合物处理。例如,参见Chem.Soc.Rev.[化学学会综述](2009),38,606和Chem.Soc.Rev.[化学学会综述](2011),40,5084。这示于方案4中。
方案4
可替代地,具有式(I)的化合物通过以下方式制备:用合适的有机金属(例如MeMgBr、MeZnCl、AlMe3)或有机类金属(例如,三甲基环三硼氧烷)试剂,在合适的金属(例如,CuBr)或催化剂络合物(例如,1,1'-双(二苯基膦基)二茂铁-二氯化钯(II))的存在下,任选地在碱(例如,K2CO3)的存在下,在惰性溶剂(如甲苯或2-甲基四氢呋喃)中,在从80℃至110℃的温度下处理具有式(VII)的化合物,其中Z是氯、溴、碘。对于实例,参见J.Org.Chem.[有机化学杂志](1987),52,3847;WO 2006/045514;WO 2004/080998。这示于以下方案5中。
方案5
具有式(VII)的化合物(其中Z是氯、溴或碘)可以通过以下方式获得:具有式(VIII)的化合物(其中X是OH,并且Z是氯、溴或碘)和具有式(III)的胺化合物通过活化具有式(VIII)的化合物的羧酸官能团的酰胺偶联转化,其是通常通过以下方式而发生的过程:将羧酸的-OH转化为良好的离去基团如氯化物基团,例如通过使用(COCl)2或SOCl2,然后优选地在合适的溶剂(例如,乙腈、二甲基乙酰胺、二氯甲烷或四氢呋喃)中,优选地在25℃与60℃之间的温度下,并且任选地在碱(如三乙胺或N,N-二异丙基乙胺)的存在下;或可替代地在文献中针对酰胺偶联描述的条件(如1-丙烷膦酸环酐(T3P))下,在合适的溶剂(例如,MeCN)中,任选地在碱(例如,三乙胺或N,N-二异丙基乙胺)的存在下用具有式(III)的化合物处理。例如,参见Chem.Soc.Rev.[化学学会综述](2009),38,606和Chem.Soc.Rev.[化学学会综述](2011),40,5084。这示于方案6中。
方案6
具有式(II)的化合物(其中X是OH或C1-C4-烷氧基)通过以下方式制备:用合适的有机金属(例如MeMgBr、MeZnCl、AlMe3)或有机类金属(例如,三甲基环三硼氧烷)试剂,在合适的金属源(例如,CuBr)或催化剂络合物(例如,1,1'-双(二苯基膦基)二茂铁-二氯化钯(II))的存在下,任选地在碱(例如,K2CO3)的存在下,在惰性溶剂(如甲苯或Me-THF)中,在从80℃至110℃的温度下处理具有式(VIII)的化合物(其中X是OH或C1-C4-烷氧基,并且Z是氯、溴、碘)。对于相关实例,参见:J.Org.Chem.[有机化学杂志](1987),52,3847;WO 2006/045514;WO 2004/080998。这示于方案7中。
方案7
具有式(VI)的化合物(其中X是OH或C1-C4-烷氧基,并且Y是OH或卤素)通过以下方式制备:用合适的有机金属(例如MeMgBr、MeZnCl、AlMe3)或有机类金属(例如,三甲基环三硼氧烷)试剂,在合适的金属源(例如,CuBr)或催化剂络合物(例如,1,1'-双(二苯基膦基)二茂铁-二氯化钯(II))的存在下,任选地在碱(例如,K2CO3)的存在下,在惰性溶剂(如甲苯或2-甲基四氢呋喃)中,在从60℃至110℃的温度下处理具有式(IX)的化合物(其中Z是溴、碘,并且Y是氟、氯或溴,优选氯)。J.Org.Chem.[有机化学杂志](1987),52,3847;WO 2006/045514;WO 2004/080998。具有式(IX)的化合物是已知的或可商购的。这示于方案8中。
方案8
具有式(VIII)的化合物(其中X是OH或C1-C4-烷氧基,并且Z是氯或溴)通过以下方式制备:使亲核的具有式(IV)的化合物与亲电的具有式(IX)的化合物(其中X是OH或C1-C4-烷氧基,并且Y是合适的离去基团,如氟、氯、溴、碘、BF3K、B(OH)2或B(频哪醇),并且Z是氯或溴,优选溴),在碱(例如,KO-t-Bu、K2CO3、三乙胺、或Cs2CO3)的存在下,在合适的溶剂(例如,乙腈、四氢呋喃、2-甲基四氢呋喃、N-甲基吡咯烷酮、二甲基乙酰胺)中,在60℃与110℃之间的温度下,并且优选使用金属催化剂络合物(例如,Cu和Pd)进行反应。对于相关实例,参见Eur.J.Org.Chem.[欧洲有机化学杂志],(2011),18,3353;J.Org.Chem.[有机化学杂志],(2009),74,7951;Tetrahedron Lett.[四面体快报],(2012),53,5318。具有式(IX)的化合物是已知的或可商购的。这示于方案9中。
方案9
具有式(II)的化合物(其中X是OH或C1-C4-烷氧基)通过以下方式制备:使亲核的具有式(VI)的化合物(其中Y是OH,并且X是OH或C1-C4-烷氧基)与亲电的具有式(X)的化合物(其中E是氟、氯、溴、碘、BF3K、B(OH)2或B(频哪醇)),在合适的溶剂(例如,二氯甲烷、1,2-二氯甲烷、乙腈、四氢呋喃、2-甲基四氢呋喃、N-甲基吡咯烷酮、二甲基乙酰胺)中,在40℃与80℃之间的温度下,并使用金属源(例如,Cu(OAc)2),并且优选地在氧化剂(如O2)或合适的钯预催化剂(如RockPhos Pd G3)的存在下,在碱(例如,K3PO4)和合适的溶剂(例如,二甲醚或甲苯)的存在下,在20℃与80℃之间的温度下进行反应。对于相关实例,参见Org.Lett.[有机快报],(2003),5,1381;Tetrahedron Lett.[四面体快报](1998),39,2933;TetrahedronLett.[四面体快报],(2003),44,3863;和Org.Lett.[有机快报],(2013),15,2876。具有式(X)的化合物和具有式(VI)的化合物是已知的或可商购的。这示于方案10中。
方案10
具有式(I)的化合物通过以下方式制备:使亲核的具有式(V)的化合物(其中Y是OH)与亲电的具有式(X)的化合物(其中E是氯、溴、碘、BF3K、B(OH)2或B(频哪醇)),在合适的溶剂(例如,二氯甲烷、1,2-二氯甲烷、乙腈、四氢呋喃、2-甲基四氢呋喃)中,在40℃与80℃之间的温度下,并使用金属源(例如,Cu(OAc)2),任选地在氧化剂(如O2)或合适的钯预催化剂(如RockPhos Pd G3)的存在下,在碱(例如,K3PO4)和合适的溶剂(例如,二甲醚或甲苯)的存在下,在20℃与80℃之间的温度下进行反应。对于相关实例,参见Org.Lett.[有机快报],(2003),5,1381;Tetrahedron Lett.[四面体快报](1998),39,2933;Tetrahedron Lett.[四面体快报],(2003),44,3863;和Org.Lett.[有机快报],(2013),15,2876。具有式(X)的化合物是已知的或可商购的。这示于方案11中。
方案11
具有式(II)的化合物(其中X是C1-C4-烷氧基,并且R3是C1-C4-烷氧基、C2-C4-烯氧基、C2-C4-炔氧基、C1-C3-氟烷氧基、C3-C4-环烷氧基环烷基或苯氧基)通过以下方式制备:用具有式(XII)RZ-OH的化合物(其中RZ是C1-C4-烷氧基、C2-C4-烯氧基、C2-C4-炔氧基、C1-C3-氟烷氧基、C3-C4-环烷基或苯氧基),在碱(例如NaH、KO-t-Bu、K3PO4、K2CO3、三乙基胺、或Cs2CO3)的存在下,在合适的溶剂(例如,N-甲基吡咯烷酮、二甲基乙酰胺、乙腈、四氢呋喃、2-甲基四氢呋喃、环丁砜、二甲基亚砜)中,在20℃-120℃之间的温度下处理具有式(XI)的化合物(Z是卤素),以得到具有式(II)的化合物。对于相关实例,参见:F.Terrier,ModernNucleophilic Aromatic Substitution[现代亲核芳族取代],Wiley-VCH[威利-VCH出版社],魏因海姆,2013。此外,具有式(II)的化合物,其中X=C1-C4-烷氧基,容易在文献中描述的条件下水解,以得到具有式(II)的化合物,其中X是OH。这示于方案12中
方案12
可替代地,具有式(II)的化合物(其中R3是C1-C4-烷氧基、C2-C4-烯氧基、C2-C4-炔氧基、C1-C3-氟烷氧基、C3-C4-环烷氧基环烷基)通过以下方式制备:用具有式(XIII)RZ-LG的化合物(其中RZ是如上结合方案12所定义的,LG是合适的离去基团,如溴或氯),在碱(如NaH、KO-t-Bu、K3PO4、K2CO3、三乙基胺、或Cs2CO3)的存在下,在合适的溶剂(例如,N-甲基吡咯烷酮、二甲基乙酰胺、乙腈、四氢呋喃、2-甲基四氢呋喃、环丁砜、二甲基亚砜)中,在20℃与100℃之间的温度下处理具有式(XI)的化合物(其中Z是OH)。这示于方案13中
方案13
如已指示的,出人意料地,现在已经发现,为实际目的,本发明的具有式(I)的化合物具有非常有利水平的用来保护植物免受由真菌引起的疾病的生物活性。
具有式(I)的化合物可以在农业部门和相关使用领域中用作例如用于控制植物有害生物的活性成分,或者在非生命材料上用于控制腐败微生物或对人潜在有害的有机体。这些新颖化合物的特征是在低施用比率下具有优异的活性,植物耐受良好以及对环境安全。它们有非常有用的治疗性的、预防性的和系统性的特性并且可以用于保护很多栽培植物。具有式(I)的化合物可以用于抑制或破坏在不同的有用植物作物的植物或植物部分(果实、花、叶子、茎、块茎、根)上出现的有害生物,同时还保护了稍后生长的那些植物部分免于例如植物病原性微生物的侵害。
本发明进一步涉及用于通过处理植物或植物繁殖材料和/或收获的粮食作物来控制或预防易受微生物攻击的植物或植物繁殖材料和/或收获的食物作物的侵染的方法,其中将有效量的具有式(I)的化合物施用至所述植物、其部分或其场所。
还能使用具有式(I)的化合物作为杀真菌剂。如本文使用的,术语“杀真菌剂”意指控制、改变或预防真菌生长的化合物。术语“杀真菌有效量”在使用时意指能够对真菌生长产生影响的这种化合物或此类化合物的组合的量。控制或改变影响包括所有从自然发育的偏离,如杀死、阻滞等,并且预防包括在植物内或上面预防真菌感染的屏障或其他防御构造。
还能使用具有式(I)的化合物作为处理植物繁殖材料(例如,种子,如果实、块茎或谷粒)或植物插条的拌种剂,用于保护对抗真菌感染连同对抗土壤里存在的植物病原性真菌。可以在种植前用包含具有式(I)的化合物的组合物处理繁殖材料:例如可以在播种前拌种。还可以通过在液体配制品中浸渍种子或通过用固体配制品包衣它们,将具有式(I)的活性化合物施用至谷粒(包衣)。还可以在种植繁殖材料时,将组合物施用至种植位点,例如在播种期间施用至种子的犁沟。本发明还涉及处理植物繁殖材料的此类方法,并且涉及如此处理的植物繁殖材料。
此外,具有式(I)的化合物可以在相关领域中用于控制真菌,例如用于工业材料(包括木材以及与木材有关的工业产品)保护、食品储存、卫生管理。
此外,本发明可以用于保护非生命材料(例如木料、墙板和涂料)免于真菌侵袭。
具有式(I)的化合物例如针对疾病的真菌和真菌载体以及植物病原性细菌和病毒是有效的。这些病害的真菌和真菌载体以及植物病原性的细菌和病毒是例如:
伞枝梨头霉、链格孢属物种、丝囊霉属物种、壳二孢属物种、曲霉属物种(包括黄曲霉、烟曲霉、构巢曲霉、黑曲霉、土曲霉)、短梗霉属物种(包括出芽短梗霉(A.pullulans))、皮炎芽生菌、小麦白粉病菌、莴苣盘梗霉(Bremia lactucae)、葡萄座腔菌属物种(包括葡萄溃疡病菌(B.dothidea)、树花地衣葡萄座腔菌(B.obtusa))、葡萄孢属物种(包括灰葡萄孢(B.cinerea))、念珠菌属物种(包括白色念珠菌、光滑球念珠菌(C.glabrata)、克鲁斯念珠菌(C.krusei)、萄牙念珠菌(C.lusitaniae)、近平滑念珠菌(C.parapsilosis)、热带念珠菌(C.tropicalis))、Cephaloascus fragrans、长喙壳属物种、尾孢属物种(包括褐斑病菌(C.arachidicola))、晚斑病菌(Cercosporidium personatum)、枝孢霉属物种、麦角菌、粗球孢子菌、旋孢腔菌属物种、炭疽菌属物种(包括香蕉炭疽病菌(C.musae))、新型隐球菌、间座壳属(Diaporthe)物种、亚隔孢壳属物种、内脐蠕孢属物种、痂囊腔菌属物种、表皮癣菌属物种、梨火疫病菌、白粉菌属物种(包括菊科白粉菌(E.cichoracearum))、葡萄顶枯病菌(Eutypa lata)、镰刀菌属物种(包括大刀镰刀菌、禾谷镰刀菌、F.langsethiae、串珠镰刀菌、胶孢镰刀菌、茄病镰刀菌、尖孢镰刀菌、层出镰刀菌)、小麦全蚀病菌(Gaeumannomycesgraminis)、藤仓赤霉菌(Gibberella fujikuroi)、煤烟病菌(Gloeodes pomigena)、香蕉炭疽盘长孢菌(Gloeosporium musarum)、苹果炭疽病菌(Glomerella cingulate)、葡萄球座菌(Guignardia bidwellii)、植物受桧胶锈菌(Gymnosporangium juniperi-virginianae)、长蠕孢属物种、驼孢锈菌属物种、组织胞浆菌属物种(包括荚膜组织胞浆菌(H.capsulatum))、红线病菌、Leptographium lindbergi、辣椒白粉病菌(Leveillulataurica)、松针散盘壳菌(Lophodermium seditiosum)、雪霉叶枯菌(Microdochiumnivale)、小孢子菌属物种、链核盘菌属物种、毛霉属物种、球腔菌属物种(包括禾生球腔菌、苹果黑点病菌(M.pomi))、树梢枯病菌、云杉病菌、副球孢子菌属物种、青霉属物种(包括指状青霉、意大利青霉)、霉样真霉属物种、指霜霉属物种(包括玉蜀黍指霜霉、菲律宾霜指霉和高粱指霜霉)、霜霉属物种、颖枯壳针孢、豆薯层锈菌、桑黄火木针层孔菌(Phellinusigniarus)、瓶霉蚁属物种、茎点霉属物种、葡萄生拟茎点菌(Phomopsis viticola)、疫霉菌属物种(包括致病疫霉菌)、单轴霉属物种(包括霍尔斯单轴霉菌、葡萄霜霉病菌(P.viticola))、格孢腔菌属物种、叉丝单囊壳属物种(包括白叉丝单囊壳(P.leucotricha))、禾谷多粘菌(Polymyxa graminis)、甜菜多粘菌(Polymyxa betae)、小麦基腐病菌(Pseudocercosporella herpotrichoides)、假单胞菌属物种、假霜霉属物种(包括黄瓜霜霉病菌、葎草假霜霉)、Pseudopeziza tracheiphila、霜霉属物种(包括大麦柄锈菌(P.hordei)、小麦叶锈病菌(P.recondita)、条形柄锈菌(P.striiformis)、小麦褐锈菌(P.triticina))、埋核盘菌属物种、核腔菌属物种、梨孢属物种(包括稻瘟病菌(P.oryzae))、腐霉属物种(包括终极腐霉菌)、柱隔孢属物种、丝核菌属物种、微小根毛霉(Rhizomucor pusillus)、少根根霉、喙孢属物种、丝孢菌属物种(包括尖端赛多孢子菌和多育赛多孢子菌)、煤点病(Schizothyrium pomi)、核盘菌属物种、小核菌属物种、壳针孢属物种(包括颖枯壳针孢(S.nodorum)、小麦壳针孢(S.tritici))、草莓白粉病菌(Sphaerothecamacularis)、棕丝单囊壳(Sphaerotheca fusca)(黄瓜白粉病菌(Sphaerothecafuliginea))、孢子丝菌属(Sporothorix)物种、颖枯壳多孢(Stagonospora nodorum)、匍柄霉属(Stemphylium)物种、毛韧革菌(Stereum hirsutum)、水稻枯纹病菌(Thanatephoruscucumeris)、根串珠霉(Thielaviopsis basicola)、腥黑粉菌属物种、木霉属物种(包括哈茨木霉、拟康氏木霉、绿色木霉)、毛癣菌属物种、核瑚菌属物种、葡萄钩丝壳、条黑粉菌属(Urocystis)物种、黑粉菌属(Ustilago)物种、黑星菌属物种(包括苹果黑星菌(V.inaequalis))、轮枝孢属物种、以及黄单胞菌属物种。
具有式(I)的化合物可以用于例如草坪,观赏植物如花卉、灌木、阔叶树木或常绿植物,例如松柏类,以及树木注入、有害生物管理等。
在本发明的范围内,有待保护的目标作物和/或有用植物典型地包括多年生和一年生作物,如浆果植物,例如黑莓、蓝莓、蔓越莓、树莓以及草莓;谷物,例如大麦、玉蜀黍(玉米)、粟、燕麦、水稻、黑麦、高粱、黑小麦以及小麦;纤维植物,例如棉花、亚麻、大麻、黄麻以及剑麻;大田作物,例如糖甜菜和饲料甜菜、咖啡豆、啤酒花、芥菜、油菜(卡诺拉)、罂粟、甘蔗、向日葵、茶以及烟草;果树,例如苹果、杏、鳄梨、香蕉、樱桃、柑橘、油桃、桃、梨以及李子;草,例如百慕达草、蓝草、本特草、蜈蚣草、牛毛草、黑麦草、圣奥古斯丁草以及结缕草;药草,如罗勒、琉璃苣、细香葱、胡荽、薰衣草、独活草、薄荷、牛至、荷兰芹、迷迭香、鼠尾草以及百里香;豆类,例如菜豆、小扁豆、豌豆以及大豆;坚果,例如杏仁、腰果、落花生、榛子、花生、山核桃、开心果以及核桃;棕榈植物,例如油棕榈;观赏植物,例如花卉、灌木以及树木;其他树木,例如可可树、椰子树、橄榄树以及橡胶树;蔬菜,例如芦笋、茄子、西兰花、卷心菜、胡萝卜、黄瓜、大蒜、莴苣、西葫芦、甜瓜、秋葵、洋葱、胡椒、马铃薯、南瓜、大黄、菠菜以及番茄;和葡萄藤,例如葡萄。
术语“有用植物”应当理解为还包括由于常规育种方法或基因工程致使其对除草剂(像溴草腈)或除草剂类(例如像HPPD抑制剂、ALS抑制剂,例如氟嘧磺隆、氟丙磺隆和三氟啶磺隆、EPSPS(5-烯醇-丙酮-莽草酸-3-磷酸-合成酶)抑制剂、GS(谷氨酰胺合成酶)抑制剂或PPO(原卟啉原氧化酶)抑制剂)耐受的有用植物。已经通过常规育种方法(诱变)致使对咪唑啉酮(例如甲氧咪草烟)耐受的作物的实例是夏季油菜(卡诺拉)。已经通过基因工程方法致使对除草剂或除草剂类耐受的作物的实例包括草甘膦和草铵膦抗性玉蜀黍品种,它们是以/>Herculex/>和/>商标名可商购的。
术语“有用植物”应当理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成一种或多种选择性作用毒素的有用植物,这些毒素是如已知例如来自于产毒素细菌,尤其是芽孢杆菌属的那些细菌。
这样的植物的实例是:(玉蜀黍品种,表达CryIA(b)毒素);YieldGard/>(玉蜀黍品种,表达CryIIIB(b1)毒素);YieldGard/>(玉蜀黍品种,表达CryIA(b)和CryIIIB(b1)毒素);/>(玉蜀黍品种,表达Cry9(c)毒素);Herculex/>(玉蜀黍品种,表达CryIF(a2)毒素和获得对除草剂草铵膦铵盐耐受性的酶膦丝菌素N-乙酰基转移酶(PAT));NuCOTN/>(棉花品种,表达CryIA(c)毒素);(棉花品种,表达CryIA(c)毒素);Bollgard/>(棉花品种,表达CryIA(c)和CryIIA(b)毒素);/>(棉花品种,表达VIP毒素);/>(马铃薯品种,表达CryIIIA毒素);/>GT Advantage(GA21耐草甘膦性状)、CB Advantage(Bt11玉米螟(CB)性状)、/>RW(玉米根虫性状)以及/>
术语“作物”应当理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成一种或多种选择性作用毒素的作物植物,这些毒素是如已知例如来自于产毒素细菌,尤其是芽孢杆菌属的那些细菌。
可以由此类转基因植物表达的毒素包括例如,来自蜡样芽孢杆菌或日本金龟子芽孢杆菌的杀昆虫蛋白;或者来自苏云金芽孢杆菌的杀昆虫蛋白,如δ-内毒素,例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或者营养期杀昆虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A;或细菌定植线虫的杀昆虫蛋白,例如光杆状菌属物种(Photorhabdus spp.)或致病杆菌属物种(Xenorhabdus spp.),如发光杆菌(Photorhabdusluminescens)、嗜线虫致病杆菌(Xenorhabdus nematophilus);由动物产生的毒素,如蝎毒素、蛛毒素、蜂毒素和其他昆虫特异性神经毒素;由真菌产生的毒素,如链霉菌毒素,植物凝集素,如豌豆凝集素、大麦凝集素或雪花莲凝集素;凝集素(agglutinin);蛋白酶抑制剂,如胰蛋白酶抑制剂、丝蛋白酶抑制剂、马铃薯糖蛋白、胱抑素、木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),如蓖麻毒素、玉蜀黍-RIP、相思豆毒素、丝瓜籽毒蛋白、皂草毒素蛋白或异株泻根毒蛋白;类固醇代谢酶,如3-羟基类固醇氧化酶、蜕化类固醇-UDP-糖基-转移酶、胆固醇氧化酶、蜕化素抑制剂、HMG-COA-还原酶、离子通道阻断剂如钠通道或钙通道阻断剂、保幼激素酯酶、利尿激素受体、芪合酶、联苄合酶、几丁质酶和葡聚糖酶。
进一步,在本发明的背景下,δ-内毒素(例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C)或营养期杀昆虫蛋白(Vip)(例如Vip1、Vip2、Vip3或Vip3A)应理解为显然还包括混合型毒素、截短的毒素和经修饰的毒素。混合型毒素是通过那些蛋白的不同结构域的新组合重组产生的(参见例如,WO 02/15701)。截短的毒素,例如截短的Cry1Ab是已知的。在经修饰的毒素的情况下,天然存在的毒素的一个或多个氨基酸被替代。在这种氨基酸替代中,优选将非天然存在的蛋白酶识别序列插入毒素中,例如像在Cry3A055的情况下,一种组织蛋白酶-G-识别序列被插入Cry3A毒素中(参见WO 03/018810)。
此类毒素或能够合成此类毒素的转基因植物的实例披露于例如EP-A-0 374 753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878以及WO 03/052073中。
用于制备这样的转基因植物的方法通常是本领域技术人员已知的并且描述在例如以上提及的公开物中。CryI型脱氧核糖核酸及其制备例如从WO 95/34656、EP-A-0 367474、EP-A-0 401 979和WO 90/13651中已知。
包含在转基因植物中的毒素使得植物对有害昆虫有耐受性。此类昆虫可以存在于任何昆虫分类群,但尤其常见于甲虫(鞘翅目)、双翅昆虫(双翅目)和蛾(鳞翅目)。
包含一种或多种编码杀昆虫剂抗性并且表达一种或多种毒素的基因的转基因植物是已知的并且其中一些是可商购的。这样的植物的实例是:(玉蜀黍品种,表达Cry1Ab毒素);YieldGard/>(玉蜀黍品种,表达Cry3Bb1毒素);YieldGard/>(玉蜀黍品种,表达Cry1Ab和Cry3Bb1毒素);/>(玉蜀黍品种,表达Cry9C毒素);Herculex/>(玉蜀黍品种,表达Cry1Fa2毒素和获得对除草剂草铵膦铵的耐受性的酶膦丝菌素N-乙酰基转移酶(PAT));NuCOTN/>(棉花品种,表达Cry1Ac毒素);Bollgard/>(棉花品种,表达Cry1Ac毒素);Bollgard/>(棉花品种,表达Cry1Ac和Cry2Ab毒素);/>(棉花品种,表达Vip3A和Cry1Ab毒素);/>(马铃薯品种,表达Cry3A毒素);/>GT Advantage(GA21耐草甘膦性状)、/>CB Advantage(Bt11玉米螟(CB)性状)以及/>
这样的转基因作物的另外的实例是:
1.Bt11玉蜀黍,来自先正达种子公司(Syngenta Seeds SAS),霍比特路(Cheminde l'Hobit)27,F-31 790圣苏维尔(St.Sauveur),法国,登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达截短的Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt11玉蜀黍还转基因表达PAT酶以获得对除草剂草铵膦的耐受性。
2.Bt176玉蜀黍,来自先正达种子公司,霍比特路27,F-31 790圣苏维尔,法国,登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt176玉蜀黍还转基因表达酶PAT以获得对除草剂草铵膦的耐受性。
3.MIR604玉蜀黍,来自先正达种子公司,霍比特路27,F-31 790圣苏维尔,法国,登记号C/FR/96/05/10。通过转基因表达经修饰的Cry3A毒素使之具有昆虫抗性的玉蜀黍。此毒素是通过插入组织蛋白酶-G-蛋白酶识别序列而经修饰的Cry3A055。这样的转基因玉蜀黍植物的制备描述于WO 03/018810中。
4.MON 863玉蜀黍,来自孟山都欧洲公司(Monsanto Europe S.A.),270-272特弗伦大道(Avenue de Tervuren),B-1150布鲁塞尔,比利时,登记号C/DE/02/9。MON 863表达Cry3Bb1毒素,并且对某些鞘翅目昆虫有抗性。
5.IPC 531棉花,来自孟山都欧洲公司,270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/ES/96/02。
6.1507玉蜀黍,来自先锋海外公司(Pioneer Overseas Corporation),特德斯科大道(Avenue Tedesco),7B-1160布鲁塞尔,比利时,登记号C/NL/00/10。遗传修饰的玉蜀黍,表达蛋白质Cry1F以获得对某些鳞翅目昆虫的抗性,并且表达PAT蛋白质以获得对除草剂草铵膦的耐受性。
7.NK603×MON 810玉蜀黍,来自孟山都欧洲公司270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/GB/02/M3/03。通过将遗传修饰的品种NK603和MON 810杂交,由常规育种的杂交玉蜀黍品种构成。NK603×MON 810玉蜀黍转基因地表达由土壤杆菌属菌株CP4获得的蛋白CP4 EPSPS,其赋予对除草剂(含有草甘膦)的耐受性,以及还表达由苏云金芽孢杆菌库尔斯塔克亚种获得的Cry1Ab毒素,其带来对某些鳞翅目昆虫(包括欧洲玉米螟)的耐受性。
如本文使用的,术语“场所”意指植物在其中或其上生长的地方,或栽培植物的种子被播种的地方,或种子将要被置于土壤中的地方。它包括土壤、种子以及幼苗,连同建立的植被。
术语“植物”是指植物的所有有形部分,包括种子、幼苗、幼树、根、块茎、茎、秆、叶和果实。
术语“植物繁殖材料”应当被理解为表示所述植物的生殖部分,例如种子,这些部分可以用于所述植物的繁殖,以及营养性材料,如插条或块茎(例如马铃薯)。可以提及例如种子(在严格意义上)、根、果实、块茎、球茎、根茎以及植物的部分。还可以提及在发芽后或在出苗后将被移植的发芽植物和幼小植物。这些幼小植物可以通过浸渍进行完全或部分处理而在移植之前进行保护。优选地,“植物繁殖材料”应当理解为表示种子。
具有式(I)的化合物能以未修饰的形式使用,或者优选地,连同配制品领域中常规使用的辅助剂一起使用。为此目的,它们可以按已知方式便利地配制为可乳化浓缩物、可包衣的糊剂、直接可喷雾的或可稀释的溶液或悬浮液、稀释乳液、可湿性粉剂、可溶性粉剂、尘剂、颗粒以及还有包囊物,例如在聚合物的物质中。对于组合物的类型,根据预期目的以及当时环境来选择施用方法,如喷雾、雾化、撒粉、撒播、涂抹或浇灌。组合物还可以含有另外的辅助剂,如稳定剂、消泡剂、粘度调节剂、粘合剂或增粘剂,连同肥料、微量营养素供体或其他用于获得特殊效果的配制品。
合适的载体以及辅助剂,例如对于农业用途,可以是固体或液体的并且是在配制品技术中有用的物质,例如天然或再生的矿物物质,溶剂、分散体、湿润剂、增粘剂、增稠剂、粘合剂或肥料类。此类载体例如描述在WO 97/33890中。
悬浮液浓缩物是活性化合物的精细分散的固体颗粒悬浮于其中的水性配制品。此类配制品包含抗沉降剂和分散剂,并且可以进一步包含湿润剂以增强活性,以及消泡剂和晶体生长抑制剂。在使用时,将这些浓缩物在水中稀释,并且通常作为喷雾剂施用至有待处理的区域。活性成分的量的范围可以是从该浓缩物的0.5%至95%。
可湿性粉剂是以在水中或其他液态载体中容易分散的精细分散的颗粒形式。这些颗粒含有保留在固体基质中的活性成分。典型的固体基质包括漂白土、高岭土、硅石和其他容易湿化的有机或无机固体。可湿性粉剂通常含有从5%到95%的活性成分加上少量的润湿剂、分散剂或乳化剂。
可乳化浓缩物是在水中或其他液体中可分散的均匀的液体组合物并且可以完全由活性化合物与液体或固体乳化剂组成,或者还可以含有液态载体,如二甲苯、重芳烃石脑油、异佛尔酮和其他不挥发的有机溶剂。在使用时,将这些浓缩物分散在水中或其他液体中,并且通常作为喷雾剂施用至有待处理的区域。活性成分的量的范围可以是从该浓缩物的0.5%至95%。
颗粒配制品包括挤出物和较粗颗粒两者,并且通常在不稀释的情况下施用至需要处理的区域。用于颗粒配制品的典型载体包括沙、漂白土、凹凸棒石粘土、膨润土、蒙脱土、蛭石、珍珠岩、碳酸钙、砖、浮石、叶蜡石、高岭土、白云石、灰泥、木粉、碎玉米穗轴、碎花生壳、糖、氯化钠、硫酸钠、硅酸钠、硼酸钠、氧化镁、云母、氧化铁、氧化锌、氧化钛、氧化锑、冰晶石、石膏、硅藻土、硫酸钙以及其他有机或无机的吸收活性化合物或可被活性化合物包衣的材料。颗粒配制品通常含有5%至25%的活性成分,这些活性成分可以包括表面活性剂如重芳烃石脑油、煤油和其他石油馏分,或植物油;和/或粘着剂如糊精、胶或合成树脂。
粉尘剂是活性成分与精细分散的固体(如滑石、粘土、面粉以及其他有机与无机的作为分散剂和载体的固体)的自由流动的混合物。
微囊典型地是包裹在惰性多孔壳内的活性成分的微滴或颗粒,该惰性多孔壳允许以可控的速率让包住的材料逃逸到环境中。包囊的微滴的直径典型地为1至50微米。包裹的液体典型地占胶囊的重量的50%至95%并且除了活性化合物外还可以包含溶剂。包囊的颗粒通常是多孔颗粒,其中多孔膜将颗粒孔口密封,将活性物种以液体形式保留在颗粒孔内部。颗粒的直径的范围典型地是从1毫米至1厘米并且优选地1毫米至2毫米。颗粒通过挤出、凝聚或成球形成,或者是天然存在的。此类材料的实例是蛭石、烧结粘土、高岭土、凹凸棒石粘土、锯屑和碳精粒。壳或膜材料包括天然和合成橡胶、纤维材料、苯乙烯-丁二烯共聚物、聚丙烯腈、聚丙烯酸酯、聚酯、聚酰胺、聚脲、聚氨酯和淀粉黄原酸酯。
用于农用化学应用的其他有用配制品包括活性成分在溶剂(如丙酮、烷基化萘、二甲苯和其他有机溶剂)中的简单溶液,在该溶剂中活性成分以所希望的浓度完全溶解。也可以使用加压的喷雾剂,其中由于低沸点分散剂溶剂载体的蒸发活性成分以精细分散的形式分散。
在上述配制品类型中对于配制本发明的组合物有用的合适的农业辅助剂和载体是本领域技术人员熟知的。
可以利用的液态载体包括例如水、甲苯、二甲苯、石脑油、作物油、丙酮、甲基乙基酮、环己酮、乙酸酐、乙腈、乙酰苯、乙酸戊酯、2-丁酮、氯苯、环己烷、环己醇、乙酸烷基酯、二丙酮醇、1,2-二氯丙烷、二乙醇胺、对二乙基苯、二甘醇、松香酸二甘醇酯、二甘醇丁醚、二甘醇乙醚、二甘醇甲醚、N,N-二甲基甲酰胺、二甲亚砜、1,4-二噁烷、二丙二醇、二丙二醇甲醚、二丙二醇二苯甲酸酯、二丙二醇(diproxitol)、烷基吡咯烷酮、乙酸乙酯、2-乙基己醇、碳酸亚乙酯、1,1,1-三氯乙烷、2-庚酮、α-蒎烯、d-苧烯、乙二醇、乙二醇丁醚、乙二醇甲醚、γ-丁内酯、甘油、甘油二乙酸酯、甘油一乙酸酯、甘油三乙酸酯、十六烷、己二醇、乙酸异戊酯、乙酸异冰片酯、异辛烷、异佛尔酮、异丙苯、肉豆蔻酸异丙酯、乳酸、月桂胺、异丙叉丙酮、甲氧基丙醇、甲基异戊酮、甲基异丁基酮、月桂酸甲酯、辛酸甲酯、油酸甲酯、二氯甲烷、间二甲苯、正己烷、正辛胺、十八酸、乙酸辛胺酯、油酸、油胺、邻二甲苯、苯酚、聚乙二醇(PEG400)、丙酸、丙二醇、丙二醇单甲醚、对二甲苯、甲苯、磷酸三乙酯、三甘醇、二甲苯磺酸、石蜡、矿物油、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、甲醇、乙醇、异丙醇、以及更高分子量的醇(如戊醇、四氢糠醇、己醇、辛醇等)、乙二醇、丙二醇、甘油以及N-甲基-2-吡咯烷酮。水通常是用以稀释浓缩物的选用载体。
合适的固体载体包括例如滑石、二氧化钛、叶腊石粘土、硅石、凹凸棒石粘土、硅藻土(kieselguhr)、白垩、硅藻土(diatomaxeous earth)、石灰、碳酸钙、膨润土、漂白土、棉子壳、小麦粉、大豆粉、浮石、木粉、核桃壳粉以及木质素。
在所述液体和固体组合物中可有利地采用广泛的表面活性剂,尤其是被设计为可在施用前用载体稀释的那些。这些试剂在使用时通常占配制品重量的从0.1%至15%。它们在性质上可以是阴离子的、阳离子的、非离子的或聚合的并且可以作为乳化剂、湿润剂、悬浮剂或以其他目的采用。典型的表面活性剂包括烷基硫酸盐如月桂基硫酸二乙醇铵;烷基芳基磺酸盐,如十二烷基苯磺酸钙;烷基酚-环氧烷加成产物,如壬基酚-C.sub.18乙氧基化物;醇-环氧烷加成产物,如十三烷醇-C.sub.16乙氧基化物;皂,如硬脂酸钠;烷基萘磺酸盐,如二丁基萘磺酸钠;磺基琥珀酸二烷基酯的盐,如二(2-乙基己基)磺基琥珀酸钠;山梨糖醇酯,如山梨糖醇油酸酯;季胺,如月桂基三甲基氯化铵;脂肪酸的聚乙二醇酯,如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;以及磷酸单和二烷基酯的盐。
通常在农业组合物中使用的其他辅助剂包括结晶抑制剂、粘度调节剂、悬浮剂、喷雾液滴调节剂、颜料、抗氧化剂、发泡剂、消泡剂、遮光剂、相容性试剂、消泡剂、掩蔽剂、中和剂和缓冲剂、腐蚀抑制剂、染料、增味剂、铺展剂、渗透助剂、微量营养素、柔润剂、润滑剂以及固着剂。
此外,进一步地,其他杀生物的活性成分或组合物可以与本发明的组合物组合,并且用于本发明的方法中并且与本发明的组合物同时地或顺序地施用。当同时施用时,这些另外的活性成分可以连同本发明的组合物一起配制或混合于例如喷雾罐中。这些另外的杀生物的活性成分可以是杀真菌剂、除草剂、杀昆虫剂、杀细菌剂、杀螨剂、杀线虫剂和/或植物生长调节剂。
本文提及的使用其俗名的杀有害生物剂是,例如,从“The Pesticide Manual[杀有害生物剂手册]”,第15版,英国作物保护委员会(British Crop Protection Council)2009已知的。
此外,本发明的组合物还可以与一种或多种系统获得性抗性诱导剂(“SAR”诱导剂)一起施用。SAR诱导剂是已知的并且描述于例如美国专利号US 6,919,298中,并且包括例如水杨酸盐以及商用的SAR诱导剂阿拉酸式苯-S-甲基。
具有式(I)的化合物通常以农用化学组合物的形式使用并且可以与另外的化合物同时地或顺序地施用至有待处理的作物区域或植物。例如,这些另外的化合物可以是影响植物生长的肥料或微量营养素供体或其他制剂。它们还可以是选择性除草剂或非选择性除草剂,连同杀昆虫剂、杀真菌剂、杀细菌剂、杀线虫剂、杀软体动物剂或这些制剂中的若干种的混合物,如果希望的话连同配制品领域中通常使用的另外的载体、表面活性剂或促进施用的辅助剂一起。
具有式(I)的化合物可以按控制或保护对抗植物病原性微生物的(杀真菌的)组合物的形式使用,所述组合物包含作为活性成分的至少一种具有式(I)的化合物或至少一种优选的如本文所定义的个别化合物(处于游离形式或处于农用化学上可用的盐形式)和至少一种上述辅助剂。
因此,本发明提供了一种组合物,优选为杀真菌组合物,其包含至少一种具有式(I)的化合物、农业上可接受的载体的和任选的辅助剂。农业上可接受的载体是例如适合农业用途的载体。农业载体在本领域是熟知的。优选地,除了包含具有式(I)的化合物,所述组合物可以包含至少一种或多种杀有害生物活性化合物,例如另外的杀真菌活性成分。
具有式(I)的化合物可以是组合物的唯一活性成分,或者适当时它可以与一种或多种另外的活性成分(如杀有害生物剂、杀真菌剂、增效剂、除草剂或植物生长调节剂)混合。在一些情况下,另外的活性成分可以产生出乎意料的协同活性。
合适的另外的活性成分的实例包括以下:无环氨基酸(acycloamino acid)杀真菌剂、脂肪族氮杀真菌剂、酰胺杀真菌剂、苯胺杀真菌剂、抗生素杀真菌剂、芳香族杀真菌剂、含砷杀真菌剂、芳基苯基酮杀真菌剂、苯甲酰胺杀真菌剂、苯甲酰苯胺杀真菌剂、苯并咪唑杀真菌剂、苯并噻唑杀真菌剂、植物杀真菌剂、桥联联苯基杀真菌剂、氨基甲酸酯杀真菌剂、苯氨甲酸酯杀真菌剂、康唑杀真菌剂、铜杀真菌剂、二甲酰亚胺杀真菌剂、二硝基苯酚杀真菌剂、二硫代氨基甲酸酯杀真菌剂、二硫戊环杀真菌剂、糠酰胺杀真菌剂、糠苯胺杀真菌剂、酰肼真菌剂、咪唑杀真菌剂、汞杀真菌剂、吗啉杀真菌剂、有机磷杀真菌剂、有机锡杀真菌剂、氧硫杂环己二烯(oxathiin)杀真菌剂、噁唑杀真菌剂、苯硫酰胺杀真菌剂、多硫化物杀真菌剂、吡唑杀菌剂、吡啶杀真菌剂、嘧啶杀真菌剂、吡咯杀真菌剂、季铵杀真菌剂、喹啉杀真菌剂、醌杀真菌剂、喹喔啉杀真菌剂、嗜球果伞素杀真菌剂、磺酰苯胺(sulfonanilide)杀真菌剂、噻二唑杀真菌剂、噻唑杀真菌剂、噻唑烷杀真菌剂、硫代氨基甲酸酯杀真菌剂、噻吩杀真菌剂、三嗪杀真菌剂、三唑杀真菌剂、三唑并嘧啶杀真菌剂、尿素杀真菌剂、缬氨酰胺(valinamide)杀真菌剂、以及锌杀真菌剂。
合适的另外的活性成分的具体实例还包括选自由以下组成的物质组的化合物:石油、1,1-双(4-氯苯基)-2-乙氧基乙醇、2,4-二氯苯基苯磺酸酯、2-氟-N-甲基-N-1-萘乙酰胺、4-氯苯基苯基砜、乙酰虫腈、涕灭砜威、赛果、果满磷、胺吸磷、草酸氢胺吸磷、双甲脒、杀螨特、三氧化二砷、偶氮苯、偶氮磷、苯菌灵、苯诺沙磷(benoxafos)、苯甲酸苄酯、联苯吡菌胺、溴灭菊酯、溴烯杀、溴硫磷、溴螨酯、噻嗪酮、丁酮威、丁酮砜威、丁基哒螨灵、多硫化钙、八氯莰烯、氯灭杀威、三硫磷、螨蜱胺、灭螨猛、杀螨醚、杀虫脒、杀虫脒盐酸盐、杀螨醇、杀螨酯、敌螨特、乙酯杀螨醇、灭螨脒(chloromebuform)、灭虫脲、丙酯杀螨醇、虫螨磷、瓜菊酯I、瓜菊酯II、瓜菊酯、克罗散泰、蝇毒磷、克罗米通、巴毒磷、硫杂灵、果虫磷、DCPM、DDT、田乐磷、田乐磷-O、田乐磷-S、内吸磷-甲基、内吸磷-O、内吸磷-O-甲基、内吸磷-S、内吸磷-S-甲基、磺吸磷(demeton-S-methylsulfon)、抑菌灵、敌敌畏、二氯磷(dicliphos)、除螨灵、甲氟磷、消螨酚(dinex)、消螨酚(dinex-diclexine)、敌螨普-4、敌螨普-6、邻敌螨消、硝戊酯、硝辛酯、硝丁酯、敌杀磷、磺基二苯、戒酒硫、DNOC、苯氧炔螨(dofenapyn)、多拉克汀、因毒磷、依立诺克丁、益硫磷、乙嘧硫磷、抗螨唑、苯丁锡、苯硫威、必螨立克(fenpyrad)、唑螨酯、胺苯吡菌酮、除螨酯、氟硝二苯胺(fentrifanil)、氟螨噻、氟螨脲、联氟螨、氟杀螨、FMC 1137、伐虫脒、伐虫脒盐酸盐、胺甲威(formparanate)、γ-HCH、果绿定、苄螨醚、十六烷基环丙烷羧酸酯、水胺硫磷、茉莉菊酯I、茉莉菊酯II、碘硫磷、林丹、丙螨氰、灭蚜磷、二噻磷、甲硫芬、虫螨畏、溴甲烷、速灭威、自克威、米尔贝肟、丙胺氟、久效磷、茂果、莫昔克丁、二溴磷(naled)、4-氯-2-(2-氯-2-甲基-丙基)-5-[(6-碘-3-吡啶基)甲氧基]哒嗪-3-酮、氟蚁灵、尼可霉素、戊氰威、戊氰威1:1氯化锌络合物、氧乐果、亚异砜磷、砜拌磷、pp'-DDT、对硫磷、苄氯菊酯、芬硫磷、伏杀磷、硫环磷、磷胺、氯化松节油(polychloroterpenes)、杀螨素(polynactins)、丙氯诺、蜱虱威、残杀威、乙噻唑磷、发疏磷、除虫菊酯I、除虫菊酯II、除虫菊酯、哒嗪硫磷、嘧硫磷、喹硫磷(quinalphos)、喹硫磷(quintiofos)、R-1492、甘氨硫磷、鱼藤酮、八甲磷、克线丹、司拉克丁、苏硫磷、SSI-121、舒非仑、氟虫胺、硫特普、硫、氟螨嗪、τ-氟胺氰菊酯、TEPP、叔丁威、四氯杀螨砜、杀螨好、噻酚诺(thiafenox)、抗虫威、久效威、甲基乙拌磷、克杀螨、苏力菌素、威菌磷、苯螨噻、三唑磷、灭蚜唑(triazuron)、三氯丙氧磷、三活菌素、蚜灭多、甲烯氟虫腈(vaniliprole)、百杀辛(bethoxazin)、二辛酸铜、硫酸铜、环丙沙星(cybutryne)、二氯萘醌、双氯酚、茵多酸、三苯锡、熟石灰、代森钠、灭藻醌、醌萍胺、西玛津、三苯基乙酸锡、三苯基氢氧化锡、育畜磷、哌嗪、托布津、氯醛糖、倍硫磷、吡啶-4-胺、士的宁、1-羟基-1H-吡啶-2-硫酮、4-(喹喔啉-2-基氨基)苯磺酰胺、8-羟基喹啉硫酸盐、溴硝醇、氢氧化铜、甲酚、双吡硫翁、多地辛、敌磺钠、甲醛、汞加芬、春雷霉素、春雷霉素盐酸盐水合物、二(二甲基二硫代氨基甲酸)镍、三氯甲基吡啶、辛噻酮、奥索利酸、土霉素、羟基喹啉硫酸钾、噻菌灵、链霉素、链霉素倍半硫酸盐、叶枯酞、硫柳汞、棉褐带卷蛾GV、放射形土壤杆菌、钝绥螨属物种(Amblyseius spp.)、芹菜夜蛾NPV、原樱翅缨小蜂(Anagrus atomus)、短距蚜小蜂(Aphelinus abdominalis)、棉蚜寄生蜂(Aphidius colemani)、食蚜瘿蚊(Aphidoletes aphidimyza)、苜蓿银纹夜蛾NPV、球形芽孢杆菌(Bacillus sphaericusNeide)、布氏白僵菌(Beauveria brongniartii)、普通草蛉(Chrysoperla carnea)、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)、苹果蠹蛾GV、西伯利亚离颚茧蜂(Dacnusasibirica)、豌豆潜叶蝇姬小蜂(Diglyphus isaea)、丽蚜小蜂(Encarsia formosa)、桨角蚜小蜂(Eretmocerus eremicus)、嗜菌异小杆线虫(Heterorhabditis bacteriophora)和大异小杆线虫(H.megidis)、斑长足瓢虫(Hippodamia convergens)、橘粉介壳虫寄生蜂(Leptomastix dactylopii)、盲蝽(Macrolophus caliginosus)、甘蓝夜蛾NPV、黄阔柄跳小蜂(Metaphycus helvolus)、黄绿绿僵菌(Metarhizium anisopliae var.acridum)、金龟子绿僵菌小孢变种(Metarhizium anisopliae var.anisopliae)、欧洲新松叶蜂(Neodiprionsertifer)NPV和红头新松叶蜂(N.lecontei)NPV、小花蝽属物种、玫烟色拟青霉(Paecilomyces fumosoroseus)、智利小植绥螨(Phytoseiulus persimilis)、毛蚊线虫(Steinernema bibionis)、小卷蛾斯氏线虫(Steinernema carpocapsae)、夜蛾斯氏线虫、格氏线虫(Steinernema glaseri)、锐比斯氏线虫(Steinernema riobrave)、Steinernemariobravis、蝼蛄斯氏线虫(Steinernema scapterisci)、斯氏线虫属物种(Steinernemaspp.)、赤眼蜂属物种、西方盲走螨(Typhlodromus occidentalis)、蜡蚧轮枝菌(Verticillium lecanii)、唑磷嗪(apholate)、双(氮丙啶)甲氨基膦硫化物(bisazir)、白消安、迪麦替夫(dimatif)、六甲蜜胺(hemel)、六甲磷(hempa)、甲基涕巴(metepa)、甲硫涕巴(methiotepa)、甲基唑磷嗪(methyl apholate)、不孕啶(morzid)、氟幼脲(penfluron)、涕巴(tepa)、硫代六甲磷(thiohempa)、硫涕巴、曲他胺、尿烷亚胺、(E)-癸-5-烯-1-基乙酸酯与(E)-癸-5-烯-1-醇、(E)-十三碳-4-烯-1-基乙酸酯、(E)-6-甲基庚-2-烯-4-醇、(E,Z)-十四碳-4,10-二烯-1-基乙酸酯、(Z)-十二碳-7-烯-1-基乙酸酯、(Z)-十六碳-11-烯醛、(Z)-十六碳-11-烯-1-基乙酸酯、(Z)-十六碳-13-烯-11-炔-1-基乙酸酯、(Z)-二十-13-烯-10-酮、(Z)-十四碳-7-烯-1-醛、(Z)-十四碳-9-烯-1-醇、(Z)-十四碳-9-烯-1-基乙酸酯、(7E,9Z)-十二碳-7,9-二烯-1-基乙酸酯、(9Z,11E)-十四碳-9,11-二烯-1-基乙酸酯、(9Z,12E)-十四碳-9,12-二烯-1-基乙酸酯、14-甲基十八碳-1-烯、4-甲基壬-5-醇与4-甲基壬-5-酮、α-多纹素、西部松小蠹集合信息素、十二碳二烯醇(codlelure)、可得蒙(codlemone)、诱蝇酮(cuelure)、环氧十九烷、十二碳-8-烯-1-基乙酸酯、十二碳-9-烯-1-基乙酸酯、十二碳-8、10-二烯-1-基乙酸酯、dominicalure、4-甲基辛酸乙酯、丁香酚、南部松小蠹集合信息素(frontalin)、诱杀烯混剂(grandlure)、诱杀烯混剂I、诱杀烯混剂II、诱杀烯混剂III、诱杀烯混剂IV、己诱剂(hexalure)、齿小蠹二烯醇(ipsdienol)、小蠢烯醇(ipsenol)、金龟子性诱剂(japonilure)、三甲基二氧三环壬烷(lineatin)、夜蛾诱剂(litlure)、粉纹夜蛾性诱剂(looplure)、诱杀酯(medlure)、蒙托么克酸(megatomoic acid)、诱虫醚(methyleugenol)、诱虫烯(muscalure)、十八碳-2,13-二烯-1-基乙酸酯、十八碳-3,13-二烯-1-基乙酸酯、贺康彼(orfralure)、椰蛀犀金龟聚集信息素(oryctalure)、非乐康(ostramone)、诱虫环(siglure)、索迪叮(sordidin)、食菌甲诱醇(sulcatol)、十四碳-11-烯-1-基乙酸酯、地中海实蝇引诱剂(trimedlure)、地中海实蝇引诱剂A、地中海实蝇引诱剂B1、地中海实蝇引诱剂B2、地中海实蝇引诱剂C、创克括(trunc-call)、2-(辛基硫代)乙醇、避蚊酮(butopyronoxyl)、丁氧基(聚丙二醇)、己二酸二丁酯、邻苯二甲酸二丁酯、丁二酸二丁酯、避蚊胺、驱蚊灵(dimethyl carbate)、邻苯二甲酸二甲酯、乙基己二醇、己脲(hexamide)、甲喹丁(methoquin-butyl)、甲基新癸酰胺(methylneodecanamide)、草氨酸盐(oxamate)、派卡瑞丁(picaridin)、1-二氯-1-硝基乙烷、1,1-二氯-2,2-二(4-乙基苯基)乙烷、1,2-二氯丙烷与1,3-二氯丙烯、1-溴-2-氯乙烷、2,2,2-三氯-1-(3,4-二氯苯基)乙基乙酸酯、2,2-二氯乙烯基2-乙基亚磺酰基乙基甲基磷酸酯、2-(1,3-二硫戊环-2-基)苯基二甲基氨基甲酸酯、2-(2-丁氧基乙氧基)乙基硫氰酸酯、2-(4,5-二甲基-1,3-二氧戊环-2-基)苯基甲基氨基甲酸酯、2-(4-氯-3,5-二甲苯基氧基)乙醇、2-氯乙烯基二乙基磷酸酯、2-咪唑啉酮、2-异戊酰茚满-1,3-二酮、2-甲基(丙-2-炔基)氨基苯基甲基氨基甲酸酯、2-氰硫基乙基月桂酸酯、3-溴-1-氯丙-1-烯、3-甲基-1-苯基吡唑-5-基二甲基氨基甲酸酯、4-甲基(丙-2-炔基)氨基-3,5-二甲苯基甲基氨基甲酸酯、5,5-二甲基-3-氧代环己-1-烯基二甲基氨基甲酸酯、阿赛硫磷、丙烯腈、氯甲桥萘、阿洛氨菌素、除害威、α-蜕化素、磷化铝、灭害威、新烟碱、乙基杀扑磷(athidathion)、甲基吡啶磷、苏云金芽孢杆菌δ-内毒素、六氟硅酸钡、多硫化钡、熏菊酯、拜耳22/190、拜耳22408、β-氟氯氰菊酯、β-氯氰菊酯、戊环苄呋菊酯(bioethanomethrin)、生物氯菊酯、双(2-氯乙基)醚、硼砂、溴苯烯磷、溴-DDT、合杀威、畜虫威、特嘧硫磷(butathiofos)、丁酯磷、砷酸钙、氰化钙、二硫化碳、四氯化碳、巴丹盐酸盐、瑟瓦定(cevadine)、冰片丹、氯丹、十氯酮、氯仿、氯化苦、氯腈肟磷、氯吡唑磷(chlorprazophos)、顺式苄呋菊酯(cis-resmethri)、顺式苄呋菊酯(cismethrin)、氰菊酯(clocythrin)、乙酰亚砷酸铜、砷酸铜、油酸铜、畜虫磷(coumithoate)、冰晶石、CS 708、苯腈磷、杀螟腈、环虫菊酯、赛灭磷、d-胺菊酯、DAEP、棉隆、脱甲基克百威(decarbofuran)、除线特(diamidafos)、异氯磷、除线磷、敌来死(dicresyl)、环虫腈、狄氏剂、二乙基5-甲基吡唑-3-基磷酸酯、喘定(dior)、四氟甲醚菊酯、地麦威、苄菊酯、甲基毒虫畏、敌蝇威、丙硝酚、戊硝酚、地乐酚、苯虫醚、蔬果磷、噻喃磷、DSP、脱皮甾酮、EI 1642、EMPC、EPBP、牛津郡丙硫磷(etaphos)、乙硫苯威、甲酸乙酯、二溴乙烷、二氯乙烷、环氧乙烷、EXD、皮蝇磷、乙苯威、杀螟硫磷、氧嘧酰胺(fenoxacrim)、吡氯氰菊酯、丰索磷、乙基倍硫磷、氟氯双苯隆(flucofuron)、丁苯硫磷、磷砒酯、丁环硫磷、呋线威、抗虫菊、双胍辛盐、双胍辛乙酸盐、四硫代碳酸钠、苄螨醚、HCH、HEOD、七氯、速杀硫磷、HHDN、氰化氢、喹啉威、IPSP、氯唑磷、碳氯灵、异艾氏剂、异柳磷、移栽灵、稻瘟灵、噁唑磷、保幼激素I、保幼激素II、保幼激素III、氯戊环、烯虫炔酯、砷酸铅、溴苯磷、啶虫磷、噻唑磷、间异丙苯基甲基氨基甲酸酯、磷化镁、叠氮磷、甲基减蚜磷、灭蚜硫磷、氯化亚汞、甲亚砜磷、威百亩、威百亩钾盐、威百亩钠盐、甲基磺酰氟、丁烯胺磷、甲氧普林、甲醚菊酯、甲氧滴滴涕、异硫氰酸甲酯、甲基氯仿、二氯甲烷、恶虫酮、灭蚁灵、奈肽磷、萘、NC-170、烟碱、硫酸烟碱、硝虫噻嗪、原烟碱、O-5-二氯-4-碘代苯基O-乙基乙基硫代膦酸酯、O,O-二乙基O-4-甲基-2-氧代-2H-苯并吡喃-7-基硫代膦酸酯、O,O-二乙基O-6-甲基-2-丙基嘧啶-4-基硫代膦酸酯、O,O,O',O'-四丙基二硫代焦磷酸酯、油酸、对-二氯苯、甲基对硫磷、五氯苯酚、月桂酸五氯苯酯、PH 60-38、芬硫磷、对氯硫磷、磷化氢、甲基辛硫磷、甲胺嘧磷、多氯二环戊二烯异构体、亚砷酸钾、硫氰酸钾、早熟素I、早熟素II、早熟素III、酰胺嘧啶磷、丙氟菊酯、猛杀威、丙硫磷、吡菌磷、反灭虫菊、苦木提取物(quassia)、喹硫磷-甲基、畜宁磷、碘柳胺、苄呋菊脂、鱼藤酮、噻嗯菊酯、鱼尼汀、利阿诺定、沙巴藜芦(sabadilla)、八甲磷、克线丹、SI-0009、噻丙腈、亚砷酸钠、氰化钠、氟化钠、六氟硅酸钠、五氯苯酚钠、硒酸钠、硫氰酸钠、磺苯醚隆(sulcofuron)、磺苯醚隆钠盐(sulcofuron-sodium)、硫酰氟、硫丙磷、焦油、噻螨威、TDE、丁基嘧啶磷、双硫磷、环戊烯丙菊酯、四氯乙烷、噻氯磷、杀虫环、杀虫环草酸盐、虫线磷、杀虫单、杀虫单钠、四溴菊酯、反氯菊酯、唑蚜威、异皮蝇磷-3(trichlormetaphos-3)、毒壤膦、混杀威、三氟甲氧威(tolprocarb)、氯啶菌酯、烯虫硫酯、藜芦定、藜芦碱、XMC、泽他米林(zetamethrin)、磷化锌、唑虫磷、氯氟醚菊酯、四氟醚菊酯、双(三丁基锡)氧化物、溴乙酰胺、磷酸铁、氯硝柳胺-乙醇胺、三丁基氧化锡、吡吗啉、蜗螺杀、1,2-二溴-3-氯丙烷、1,3-二氯丙烯、3,4-二氯四氢噻吩1,1-二氧化物、3-(4-氯苯基)-5-甲基罗丹宁、5-甲基-6-硫代-1,3,5-噻二嗪-3-基乙酸、6-异戊烯基氨基嘌呤、茴香苷、苯氯噻(benclothiaz)、细胞分裂素、DCIP、糠醛、异酰胺磷(isamidofos)、激动素、疣孢漆斑菌组合物、四氯噻吩、二甲苯酚、玉米素、乙基黄原酸钾、阿拉酸式苯、阿拉酸式苯-S-甲基、大虎杖(Reynoutria sachalinensis)提取物、α-氯代醇、安妥、碳酸钡、双鼠脲、溴鼠隆、溴敌隆、溴鼠胺、氯鼠酮、胆钙化醇、氯杀鼠灵、克灭鼠、杀鼠萘、杀鼠嘧啶、鼠得克、噻鼠灵、敌鼠、钙化醇、氟鼠灵、氟乙酰胺、氟鼠啶、氟鼠啶盐酸盐、鼠特灵、毒鼠磷、磷、杀鼠酮、灭鼠优、海葱糖苷、氟乙酸钠、硫酸铊、杀鼠灵、2-(2-丁氧基乙氧基)乙基胡椒酸酯、5-(1,3-苯并二氧杂环戊烯-5-基)-3-己基环己-2-烯酮、具有橙花叔醇的法呢醇、增效炔醚、MGK 264、增效醚、增效醛、增效酯(propyl isomer)、S421、增效散、芝麻林素(sesasmolin)、亚砜、蒽醌、环烷酸铜、王铜、二环戊二烯、塞仑、环烷酸锌、福美锌、衣马宁、利巴韦林、氯吲哚酰肼、氧化汞、甲基托布津、阿扎康唑、联苯三唑醇、糠菌唑、环唑醇、苯醚甲环唑、烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、呋吡菌胺、己唑醇、抑霉唑、亚胺唑、种菌唑、叶菌唑、腈菌唑、多效唑、稻瘟酯、戊菌唑、丙硫菌唑、啶斑肟(pyrifenox)、咪鲜胺、丙环唑、啶菌唑、硅氟唑、戊唑醇、氟醚唑、三唑酮、三唑醇、氟菌唑、灭菌唑、嘧啶醇、氯苯嘧啶醇、氟苯嘧啶醇、乙嘧酚磺酸酯(bupirimate)、甲菌定(dimethirimol)、乙菌定(ethirimol)、十二环吗啉、苯锈啶(fenpropidin)、丁苯吗啉、螺环菌胺、十三吗啉、嘧菌环胺、嘧菌胺、嘧霉胺(pyrimethanil)、拌种咯、咯菌腈、苯霜灵(benalaxyl)、呋霜灵(furalaxyl)、甲霜灵、R-甲霜灵、呋酰胺、恶霜灵(oxadixyl)、多菌灵、咪菌威(debacarb)、麦穗宁、噻苯达唑、乙菌利(chlozolinate)、菌核利(dichlozoline)、甲菌利(myclozoline)、腐霉利(procymidone)、乙烯菌核利(vinclozoline)、啶酰菌胺(boscalid)、萎锈灵、甲呋酰胺、氟酰胺(flutolanil)、灭锈胺、氧化萎锈灵、吡噻菌胺(penthiopyrad)、噻呋酰胺、多果定、双胍辛胺、嘧菌酯、醚菌胺、烯肟菌酯、烯肟菌胺、氟菌螨酯、氟嘧菌酯、醚菌酯、苯氧菌胺、肟菌酯、肟醚菌胺、啶氧菌酯、唑菌胺酯、唑胺菌酯、唑菌酯、福美铁、代森锰锌、代森锰、代森联、甲基代森锌、代森锌、敌菌丹(captafol)、克菌丹、唑呋草、灭菌丹、对甲抑菌灵、波尔多混合剂、氧化铜(copper oxide)、代森锰铜(mancopper)、喹啉铜(oxine-copper)、酞菌酯(nitrothal-isopropyl)、克瘟散、异稻瘟净(iprobenphos)、氯瘟磷(phosdiphen)、甲基立枯磷(tolclofos-methyl)、敌菌灵、苯噻菌胺、灭瘟素(blasticidin)-S、地茂散(chloroneb)、百菌清、环氟菌胺、霜脲氰、环丁氟菌胺、双氯氰菌胺(diclocymet)、哒菌酮(diclomezine)、氯硝胺(dicloran)、乙霉威(diethofencarb)、烯酰吗啉、氟吗啉、二噻农(dithianon)、噻唑菌胺(ethaboxam)、土菌灵(etridiazole)、恶唑菌酮、咪唑菌酮(fenamidone)、稻瘟酰胺(fenoxanil)、嘧菌腙(ferimzone)、氟啶胺(fluazinam)、flumetylsulforim、氟吡菌胺(fluopicolide)、fluoxytioconazole、磺菌胺(flusulfamide)、氟唑菌酰胺、环酰菌胺、三乙膦酸铝(fosetyl-aluminium)、恶霉灵(hymexazol)、丙森锌、赛座灭(cyazofamid)、磺菌威(methasulfocarb)、苯菌酮、戊菌隆(pencycuron)、苯酞、多氧霉素(polyoxins)、霜霉威(propamocarb)、吡菌苯威、碘喹唑酮(proquinazid)、咯喹酮(pyroquilon)、苯啶菌酮(pyriofenone)、喹氧灵、五氯硝基苯、噻酰菌胺、咪唑嗪(triazoxide)、三环唑、嗪氨灵、有效霉素、缬菌胺、苯酰菌胺(zoxamide)、双炔酰菌胺(mandipropamid)、氟苯醚酰胺、吡唑萘菌胺(isopyrazam)、氟唑环菌胺(sedaxane)、苯并烯氟菌唑、氟唑菌酰羟胺、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3’,4’,5’-三氟-联苯-2-基)-酰胺、异氟环丙胺、异噻菌胺、二吡米曲尼(dipymetitrone)、6-乙基-5,7-二氧代-吡咯并[4,5][1,4]二噻英并[1,2-c]异噻唑-3-甲腈、2-(二氟甲基)-N-[3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺、4-(2,6-二氟苯基)-6-甲基-5-苯基-哒嗪-3-甲腈、(R)-3-(二氟甲基)-1-甲基-N-[1,1,3-三甲基茚满-4-基]吡唑-4-甲酰胺、4-(2-溴-4-氟-苯基)-N-(2-氯-6-氟-苯基)-2,5-二甲基-吡唑-3-胺、4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、氟茚唑菌胺、甲香菌酯(jiaxiangjunzhi)、利本米昔安、二氯苯噻唑、曼德斯宾(mandestrobin)、3-(4,4-二氟-3,4-二氢-3,3-二甲基异喹啉-1-基)喹诺酮、2-[2-氟-6-[(8-氟-2-甲基-3-喹啉基)氧基]苯基]丙-2-醇、噻哌菌灵(oxathiapiprolin)、N-[6-[[[(1-甲基四唑-5-基)-苯基-亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸叔丁酯、联苯吡嗪菌胺(pyraziflumid)、氟虫胺(inpyrfluxam)、氨基甲酸酯类杀菌剂(trolprocarb)、氯氟醚菌唑、一苯三氟康唑(ipfentrifluconazole)、2-(二氟甲基)-N-[(3R)-3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺、N'-(2,5-二甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒、N'-[4-(4,5-二氯噻唑-2-基)氧基-2,5-二甲基-苯基]-N-乙基-N-甲基-甲脒、[2-[3-[2-[1-[2-[3,5-双(二氟甲基)吡唑-1-基]乙酰基]-4-哌啶基]噻唑-4-基]-4,5-二氢异噁唑-5-基]-3-氯-苯基]甲磺酸盐、N-[6-[[(Z)-[(1-甲基四唑-5-基)-苯基-亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸丁-3-炔酯、N-[[5-[4-(2,4-二甲基苯基)三唑-2-基]-2-甲基-苯基]甲基]氨基甲酸甲酯、3-氯-6-甲基-5-苯基-4-(2,4,6-三氟苯基)哒嗪、吡啶甲酰氯(pyridachlometyl)、3-(二氟甲基)-1-甲基-N-[1,1,3-三甲基茚满-4-基]吡唑-4-甲酰胺、1-[2-[[1-(4-氯苯基)吡唑-3-基]氧基甲基]-3-甲基-苯基]-4-甲基-四唑-5-酮、1-甲基-4-[3-甲基-2-[[2-甲基-4-(3,4,5-三甲基吡唑-1-基)苯氧基]甲基]苯基]四唑-5-酮、氨基吡芬(aminopyrifen)、唑嘧菌胺、吲唑磺菌胺、氟唑菌苯胺、(Z,2E)-5-[1-(4-氯苯基)吡唑-3-基]氧基-2-甲氧基亚氨基-N,3-二甲基-戊-3-烯胺、氟啶酰菌胺、苯吡克咪徳(fenpicoxamid)、异丁乙氧喹啉、氟苯喹(ipflufenoquin)、奎诺福林(quinofumelin)、异丙噻菌胺、N-[2-[2,4-二氯-苯氧基]苯基]-3-(二氟甲基)-1-甲基-吡唑-4-甲酰胺、N-[2-[2-氯-4-(三氟甲基)苯氧基]苯基]-3-(二氟甲基)-1-甲基-吡唑-4-甲酰胺、苯噻菌酯、氰烯菌酯、5-氨基-1,3,4-噻二唑-2-硫醇锌盐(2:1)、氟吡菌酰胺、氟噻唑菌腈、氟醚菌酰胺、吡丙炔(pyrapropoyne)、哌碳唑(picarbutrazox)、2-(二氟甲基)-N-(3-乙基-1,1-二甲基-茚满-4-基)吡啶-3-甲酰胺、2-(二氟甲基)-N-((3R)-1,1,3-三甲基茚满-4-基)吡啶-3-甲酰胺、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苯甲腈、美特尔特特拉普罗(metyltetraprole)、2-(二氟甲基)-N-((3R)-1,1,3-三甲基茚满-4-基)吡啶-3-甲酰胺、α-(1,1-二甲基乙基)-α-[4'-(三氟甲氧基)[1,1'-二苯基]-4-基]-5-嘧啶甲醇、氟哌啶(fluoxapiprolin)、烯肟菌酯(enoxastrobin)、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苯甲腈、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-硫烷基-1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苯甲腈、抗倒酯、丁香菌酯、中生菌素、噻菌铜、噻唑锌、阿米托林(amectotractin)、异菌脲、辛菌胺、N'-[5-溴-2-甲基-6-[(1S)-1-甲基-2-丙氧基-乙氧基]-3-吡啶基]-N-乙基-N-甲基-甲脒、N'-[5-溴-2-甲基-6-[(1R)-1-甲基-2-丙氧基-乙氧基]-3-吡啶基]-N-乙基-N-甲基-甲脒、N'-[5-溴-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒、N'-[5-氯-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒、N'-[5-溴-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-异丙基-N-甲基-甲脒(这些化合物可以由WO 2015/155075中描述的方法制备);N'-[5-溴-2-甲基-6-(2-丙氧基丙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒(此化合物可以由IPCOM000249876D中描述的方法制备);N-异丙基-N'-[5-甲氧基-2-甲基-4-(2,2,2-三氟-1-羟基-1-苯基-乙基)苯基]-N-甲基-甲脒、N'-[4-(1-环丙基-2,2,2-三氟-1-羟基-乙基)-5-甲氧基-2-甲基-苯基]-N-异丙基-N-甲基-甲脒(这些化合物可以由WO 2018/228896中描述的方法制备);N-乙基-N'-[5-甲氧基-2-甲基-4-[(2-三氟甲基)氧杂环丁烷-2-基]苯基]-N-甲基-甲脒、N-乙基-N'-[5-甲氧基-2-甲基-4-[(2-三氟甲基)四氢呋喃-2-基]苯基]-N-甲基-甲脒(这些化合物可以由WO 2019/110427中描述的方法制备);N-[(1R)-1-苄基-3-氯-1-甲基-丁-3-烯基]-8-氟-喹啉-3-甲酰胺、N-[(1S)-1-苄基-3-氯-1-甲基-丁-3-烯基]-8-氟-喹啉-3-甲酰胺、N-[(1R)-1-苄基-3,3,3-三氟-1-甲基-丙基]-8-氟-喹啉-3-甲酰胺、N-[(1S)-1-苄基-3,3,3-三氟-1-甲基-丙基]-8-氟-喹啉-3-甲酰胺、N-[(1R)-1-苄基-1,3-二甲基-丁基]-7,8-二氟-喹啉-3-甲酰胺、N-[(1S)-1-苄基-1,3-二甲基-丁基]-7,8-二氟-喹啉-3-甲酰胺、8-氟-N-[(1R)-1-[(3-氟苯基)甲基]-1,3-二甲基-丁基]喹啉-3-甲酰胺、8-氟-N-[(1S)-1-[(3-氟苯基)甲基]-1,3-二甲基-丁基]喹啉-3-甲酰胺、N-[(1R)-1-苄基-1,3-二甲基-丁基]-8-氟-喹啉-3-甲酰胺、N-[(1S)-1-苄基-1,3-二甲基-丁基]-8-氟-喹啉-3-甲酰胺、N-((1R)-1-苄基-3-氯-1-甲基-丁-3-烯基)-8-氟-喹啉-3-甲酰胺、N-((1S)-1-苄基-3-氯-1-甲基-丁-3-烯基)-8-氟-喹啉-3-甲酰胺(这些化合物可以由WO2017/153380中描述的方法制备);1-(6,7-二甲基吡唑并[1,5-a]吡啶-3-基)-4,4,5-三氟-3,3-二甲基-异喹啉、1-(6,7-二甲基吡唑并[1,5-a]吡啶-3-基)-4,4,6-三氟-3,3-二甲基-异喹啉、4,4-二氟-3,3-二甲基-1-(6-甲基吡唑并[1,5-a]吡啶-3-基)异喹啉、4,4-二氟-3,3-二甲基-1-(7-甲基吡唑并[1,5-a]吡啶-3-基)异喹啉、1-(6-氯-7-甲基-吡唑并[1,5-a]吡啶-3-基)-4,4-二氟-3,3-二甲基-异喹啉(这些化合物可以由WO 2017/025510中描述的方法制备);1-(4,5-二甲基苯并咪唑-1-基)-4,4,5-三氟-3,3-二甲基-异喹啉、1-(4,5-二甲基苯并咪唑-1-基)-4,4-二氟-3,3-二甲基-异喹啉、6-氯-4,4-二氟-3,3-二甲基-1-(4-甲基苯并咪唑-1-基)异喹啉、4,4-二氟-1-(5-氟-4-甲基-苯并咪唑-1-基)-3,3-二甲基-异喹啉、3-(4,4-二氟-3,3-二甲基-1-异喹啉基)-7,8-二氢-6H-环戊二烯并[e]苯并咪唑(这些化合物可以由WO 2016/156085中描述的方法制备);N-甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]环丙烷甲酰胺、N,2-二甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、N-乙基-2-甲基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、1-甲氧基-3-甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、1,3-二甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、3-乙基-1-甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、4,4-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮、5,5-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮、1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]吡唑-4-甲酸乙酯、N,N-二甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]-1,2,4-三唑-3-胺(这些化合物可以由WO 2017/055473、WO 2017/055469、WO 2017/093348和WO 2017/118689中描述的方法制备);2-[6-(4-氯苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇(此化合物可以由WO 2017/029179中描述的方法制备);2-[6-(4-溴苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇(此化合物可以由WO 2017/029179中描述的方法制备);3-[2-(1-氯环丙基)-3-(2-氟苯基)-2-羟基-丙基]咪唑-4-甲腈(此化合物可以由WO 2016/156290中描述的方法制备);3-[2-(1-氯环丙基)-3-(3-氯-2-氟-苯基)-2-羟基-丙基]咪唑-4-甲腈(此化合物可以由WO2016/156290中描述的方法制备);2-氨基-6-甲基-吡啶-3-甲酸(4-苯氧基苯基)甲酯(此化合物可以由WO 2014/006945中描述的方法制备);2,6-二甲基-1H,5H-[1,4]二噻英并[2,3-c:5,6-c']联吡咯-1,3,5,7(2H,6H)-四酮(此化合物可以由WO 2011/138281中描述的方法制备)、N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯硫代甲酰胺;N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺;(Z,2E)-5-[1-(2,4-二氯苯基)吡唑-3-基]氧基-2-甲氧基亚氨基-N,3-二甲基-戊-3-烯酰胺(此化合物可以由WO 2018/153707中描述的方法制备);N'-(2-氯-5-甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒;N'-[2-氯-4-(2-氟苯氧基)-5-甲基-苯基]-N-乙基-N-甲基-甲脒(此化合物可以由WO 2016/202742中描述的方法制备);2-(二氟甲基)-N-[(3S)-3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺(此化合物可以由WO 2014/095675中描述的方法制备);(5-甲基-2-吡啶基)-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲酮、(3-甲基异噁唑-5-基)-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲酮(这些化合物可以由WO 2017/220485中描述的方法制备);2-氧代-N-丙基-2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙酰胺(此化合物可以由WO 2018/065414中描述的方法制备);1-[[5-[5-(三氟甲基)-1,2,4-噁二唑-3-基]-2-噻吩基]甲基]吡唑-4-甲酸乙酯(此化合物可以由WO 2018/158365中描述的方法制备);2,2-二氟-N-甲基-2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙酰胺、N-[(E)-甲氧基亚氨基甲基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、N-[(Z)-甲氧基亚氨基甲基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、N-[N-甲氧基-C-甲基-碳酰亚胺基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺(这些化合物可以由WO 2018/202428中描述的方法制备)、氟哌啶(fluoxapiprolin)、烯肟菌酯、抗倒酯、丁香菌酯。
N-甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]环丙烷甲酰胺、N,2-二甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、N-乙基-2-甲基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、1-甲氧基-3-甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、1,3-二甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、3-乙基-1-甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、4,4-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮、5,5-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮、1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]吡唑-4-甲酸乙酯、N,N-二甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]-1,2,4-三唑-3-胺。此段落中的化合物可以由WO 2017/055473、WO 2017/055469、WO 2017/093348和WO 2017/118689中描述的方法制备。
2-[6-(4-氯苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇(此化合物可以由WO 2017/029179中描述的方法制备),2-[6-(4-溴苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇(此化合物可以由WO 2017/029179中描述的方法制备),3-[2-(1-氯环丙基)-3-(2-氟苯基)-2-羟基-丙基]咪唑-4-甲腈(此化合物可以由WO 2016/156290中描述的方法制备),3-[2-(1-氯环丙基)-3-(3-氯-2-氟-苯基)-2-羟基-丙基]咪唑-4-甲腈(此化合物可以由WO 2016/156290中描述的方法制备),
2-氨基-6-甲基-吡啶-3-甲酸(4-苯氧基苯基)甲酯(此化合物可以由WO 2014/006945中描述的方法制备),2,6-二甲基-1H,5H-[1,4]二噻英并[2,3-c:5,6-c']联吡咯-1,3,5,7(2H,6H)-四酮(此化合物可以由WO 2011/138281中描述的方法制备),N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯硫代甲酰胺、N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、(Z,2E)-5-[1-(2,4-二氯苯基)吡唑-3-基]氧基-2-甲氧基亚氨基-N,3-二甲基-戊-3-烯酰胺(此化合物可以由WO 2018/153707中描述的方法制备),N'-(2-氯-5-甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒、N'-[2-氯-4-(2-氟苯氧基)-5-甲基-苯基]-N-乙基-N-甲基-甲脒(此化合物可以由WO 2016/202742中描述的方法制备),2-(二氟甲基)-N-[(3S)-3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺(此化合物可以由WO 2014/095675中描述的方法制备),中生菌素、噻菌铜、噻唑锌、阿米托林、异菌脲、环丁氟仑(cyclobutrifluram)、氟苯醚酰胺、茴香苷(anisiflupurin)。N-[(1R)-1-苄基-3-氯-1-甲基-丁-3-烯基]-8-氟-喹啉-3-甲酰胺、N-[(1S)-1-苄基-3-氯-1-甲基-丁-3-烯基]-8-氟-喹啉-3-甲酰胺、N-[(1R)-1-苄基-3,3,3-三氟-1-甲基-丙基]-8-氟-喹啉-3-甲酰胺、N-[(1S)-1-苄基-3,3,3-三氟-1-甲基-丙基]-8-氟-喹啉-3-甲酰胺、N-[(1R)-1-苄基-1,3-二甲基-丁基]-7,8-二氟-喹啉-3-甲酰胺、N-[(1S)-1-苄基-1,3-二甲基-丁基]-7,8-二氟-喹啉-3-甲酰胺、8-氟-N-[(1R)-1-[(3-氟苯基)甲基]-1,3-二甲基-丁基]喹啉-3-甲酰胺、8-氟-N-[(1S)-1-[(3-氟苯基)甲基]-1,3-二甲基-丁基]喹啉-3-甲酰胺、N-[(1R)-1-苄基-1,3-二甲基-丁基]-8-氟-喹啉-3-甲酰胺、N-[(1S)-1-苄基-1,3-二甲基-丁基]-8-氟-喹啉-3-甲酰胺、N-((1R)-1-苄基-3-氯-1-甲基-丁-3-烯基)-8-氟-喹啉-3-甲酰胺、N-((1S)-1-苄基-3-氯-1-甲基-丁-3-烯基)-8-氟-喹啉-3-甲酰胺(这些化合物可以由WO 2017/153380中描述的方法制备)。
1-(6,7-二甲基吡唑并[1,5-a]吡啶-3-基)-4,4,5-三氟-3,3-二甲基-异喹啉、1-(6,7-二甲基吡唑并[1,5-a]吡啶-3-基)-4,4,6-三氟-3,3-二甲基-异喹啉、4,4-二氟-3,3-二甲基-1-(6-甲基吡唑并[1,5-a]吡啶-3-基)异喹啉、4,4-二氟-3,3-二甲基-1-(7-甲基吡唑并[1,5-a]吡啶-3-基)异喹啉、1-(6-氯-7-甲基-吡唑并[1,5-a]吡啶-3-基)-4,4-二氟-3,3-二甲基-异喹啉(这些化合物可以由WO 2017/025510中描述的方法制备);1-(4,5-二甲基苯并咪唑-1-基)-4,4,5-三氟-3,3-二甲基-异喹啉、1-(4,5-二甲基苯并咪唑-1-基)-4,4-二氟-3,3-二甲基-异喹啉、6-氯-4,4-二氟-3,3-二甲基-1-(4-甲基苯并咪唑-1-基)异喹啉、4,4-二氟-1-(5-氟-4-甲基-苯并咪唑-1-基)-3,3-二甲基-异喹啉、3-(4,4-二氟-3,3-二甲基-1-异喹啉基)-7,8-二氢-6H-环戊二烯并[e]苯并咪唑(这些化合物可以由WO 2016/156085中描述的方法制备)。
N'-[5-溴-2-甲基-6-[(1S)-1-甲基-2-丙氧基-乙氧基]-3-吡啶基]-N-乙基-N-甲基-甲脒、N'-[5-溴-2-甲基-6-[(1R)-1-甲基-2-丙氧基-乙氧基]-3-吡啶基]-N-乙基-N-甲基-甲脒、N'-[5-溴-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒、N'-[5-氯-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒、N'-[5-溴-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-异丙基-N-甲基-甲脒,(这些化合物可以由WO2015/155075中所描述的方法制备);N'-[5-溴-2-甲基-6-(2-丙氧基丙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒(此化合物可以由IPCOM000249876D中描述的方法制备);N-异丙基-N'-[5-甲氧基-2-甲基-4-(2,2,2-三氟-1-羟基-1-苯基-乙基)苯基]-N-甲基-甲脒、N'-[4-(1-环丙基-2,2,2-三氟-1-羟基-乙基)-5-甲氧基-2-甲基-苯基]-N-异丙基-N-甲基-甲脒(这些化合物可以由WO 2018/228896中描述的方法制备);N-乙基-N'-[5-甲氧基-2-甲基-4-[(2-三氟甲基)氧杂环丁烷-2-基]苯基]-N-甲基-甲脒、N-乙基-N'-[5-甲氧基-2-甲基-4-[(2-三氟甲基)四氢呋喃-2-基]苯基]-N-甲基-甲脒(这些化合物可以由WO 2019/110427中描述的方法制备)。
(5-甲基-2-吡啶基)-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲酮、(3-甲基异噁唑-5-基)-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲酮(这些化合物可以由WO 2017/220485中描述的方法制备);2-氧代-N-丙基-2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙酰胺(此化合物可以由WO 2018/065414中描述的方法制备);
1-[[5-[5-(三氟甲基)-1,2,4-噁二唑-3-基]-2-噻吩基]甲基]吡唑-4-甲酸乙酯(此化合物可以由WO 2018/158365中描述的方法制备);2,2-二氟-N-甲基-2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙酰胺、N-[(E)-甲氧基亚氨基甲基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、N-[(Z)-甲氧基亚氨基甲基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、N-[N-甲氧基-C-甲基-碳酰亚胺基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺(这些化合物可以由WO 2018/202428中描述的方法制备);N-(2-氟苯基)-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺,[(1S,2S)-1-甲基-2-(邻甲苯基)丙基](2S)-2-[(4-甲氧基-3-丙酰基氧基-吡啶-2-羰基)氨基]丙酸酯,辛菌胺、氯吲哚酰肼、嘧啶类杀菌剂(flumetylsulforim)、氟康唑(fluoxytioconazole)。
具有式(I)的化合物与活性成分的以下混合物是优选的。缩写“TX”意指选自由以下组成的组的一种组合物:如表A-1至A-48或B-1至B-40(下文)中所示的化合物,或表T1(下文)中所列出的化合物1.1至1.98:
选自由以下组成的物质组的化合物:石油+TX、1,1-双(4-氯苯基)-2-乙氧基乙醇+TX、2,4-二氯苯基苯磺酸酯+TX、2-氟-N-甲基-N-1-萘乙酰胺+TX、4-氯苯基苯基砜+TX、乙酰虫腈+TX、涕灭砜威+TX、赛果+TX、果满磷+TX、胺吸磷+TX、草酸氢胺吸磷+TX、双甲脒+TX、杀螨特+TX、三氧化二砷+TX、偶氮苯+TX、偶氮磷+TX、苯菌灵+TX、苯诺沙磷(benoxafos)+TX、苯甲酸苄酯+TX、联苯吡菌胺+TX、溴灭菊酯+TX、溴烯杀+TX、溴硫磷+TX、溴螨酯+TX、噻嗪酮+TX、丁酮威+TX、丁酮砜威+TX、丁基哒螨灵+TX、多硫化钙+TX、八氯莰烯+TX、氯灭杀威+TX、三硫磷+TX、螨蜱胺+TX、灭螨猛+TX、杀螨醚+TX、杀虫脒+TX、杀虫脒盐酸盐+TX、杀螨醇+TX、杀螨酯+TX、敌螨特+TX、乙酯杀螨醇+TX、灭螨脒(chloromebuform)+TX、灭虫脲+TX、丙酯杀螨醇+TX、虫螨磷+TX、瓜菊酯I+TX、瓜菊酯II+TX、瓜菊酯+TX、克罗散泰+TX、蝇毒磷+TX、克罗米通+TX、巴毒磷+TX、硫杂灵+TX、果虫磷+TX、DCPM+TX、DDT+TX、田乐磷+TX、田乐磷-O+TX、田乐磷-S+TX、内吸磷-甲基+TX、内吸磷-O+TX、内吸磷-O-甲基+TX、内吸磷-S+TX、内吸磷-S-甲基+TX、磺吸磷(demeton-S-methylsulfon)+TX、抑菌灵+TX、敌敌畏+TX、二氯磷(dicliphos)+TX、除螨灵+TX、甲氟磷+TX、消螨酚(dinex)+TX、消螨酚(dinex-diclexine)+TX、敌螨普-4+TX、敌螨普-6+TX、邻敌螨消+TX、硝戊酯+TX、硝辛酯+TX、硝丁酯+TX、敌杀磷+TX、磺基二苯+TX、戒酒硫+TX、DNOC+TX、苯氧炔螨(dofenapyn)+TX、多拉克汀+TX、因毒磷+TX、依立诺克丁+TX、益硫磷+TX、乙嘧硫磷+TX、抗螨唑+TX、苯丁锡+TX、苯硫威+TX、必螨立克(fenpyrad)+TX、唑螨酯+TX、胺苯吡菌酮+TX、除螨酯+TX、氟硝二苯胺(fentrifanil)+TX、氟螨噻+TX、氟螨脲+TX、联氟螨+TX、氟杀螨+TX、FMC 1137+TX、伐虫脒+TX、伐虫脒盐酸盐+TX、胺甲威(formparanate)+TX、γ-HCH+TX、果绿定+TX、苄螨醚+TX、十六烷基环丙烷羧酸酯+TX、水胺硫磷+TX、茉莉菊酯I+TX、茉莉菊酯II+TX、碘硫磷+TX、林丹+TX、丙螨氰+TX、灭蚜磷+TX、二噻磷+TX、甲硫芬+TX、虫螨畏+TX、溴甲烷+TX、速灭威+TX、自克威+TX、米尔贝肟+TX、丙胺氟+TX、久效磷+TX、茂果+TX、莫昔克丁+TX、二溴磷(naled)+TX、4-氯-2-(2-氯-2-甲基-丙基)-5-[(6-碘-3-吡啶基)甲氧基]哒嗪-3-酮+TX、氟蚁灵+TX、尼可霉素+TX、戊氰威+TX、戊氰威1:1氯化锌络合物+TX、氧乐果+TX、亚异砜磷+TX、砜拌磷+TX、pp'-DDT+TX、对硫磷+TX、苄氯菊酯+TX、芬硫磷+TX、伏杀磷+TX、硫环磷+TX、磷胺+TX、氯化松节油(polychloroterpenes)+TX、杀螨素(polynactins)+TX、丙氯诺+TX、蜱虱威+TX、残杀威+TX、乙噻唑磷+TX、发疏磷+TX、除虫菊酯I+TX、除虫菊酯II+TX、除虫菊酯+TX、哒嗪硫磷+TX、嘧硫磷+TX、喹硫磷(quinalphos)+TX、喹硫磷(quintiofos)+TX、R-1492+TX、甘氨硫磷+TX、鱼藤酮+TX、八甲磷+TX、克线丹+TX、司拉克丁+TX、苏硫磷+TX、SSI-121+TX、舒非仑+TX、氟虫胺+TX、硫特普+TX、硫+TX、氟螨嗪+TX、τ-氟胺氰菊酯+TX、TEPP+TX、叔丁威+TX、四氯杀螨砜+TX、杀螨好+TX、噻酚诺(thiafenox)+TX、抗虫威+TX、久效威+TX、甲基乙拌磷+TX、克杀螨+TX、苏力菌素+TX、威菌磷+TX、苯螨噻+TX、三唑磷+TX、灭蚜唑(triazuron)+TX、三氯丙氧磷+TX、三活菌素+TX、蚜灭多+TX、甲烯氟虫腈(vaniliprole)+TX、百杀辛(bethoxazin)+TX、二辛酸铜+TX、硫酸铜+TX、环丙沙星(cybutryne)+TX、二氯萘醌+TX、双氯酚+TX、茵多酸+TX、三苯锡+TX、熟石灰+TX、代森钠+TX、灭藻醌+TX、醌萍胺+TX、西玛津+TX、三苯基乙酸锡+TX、三苯基氢氧化锡+TX、育畜磷+TX、哌嗪+TX、托布津+TX、氯醛糖+TX、倍硫磷+TX、吡啶-4-胺+TX、士的宁+TX、1-羟基-1H-吡啶-2-硫酮+TX、4-(喹喔啉-2-基氨基)苯磺酰胺+TX、8-羟基喹啉硫酸盐+TX、溴硝醇+TX、氢氧化铜+TX、甲酚+TX、双吡硫翁+TX、多地辛+TX、敌磺钠+TX、甲醛+TX、汞加芬+TX、春雷霉素+TX、春雷霉素盐酸盐水合物+TX、二(二甲基二硫代氨基甲酸)镍+TX、三氯甲基吡啶+TX、辛噻酮+TX、奥索利酸+TX、土霉素+TX、羟基喹啉硫酸钾+TX、噻菌灵+TX、链霉素+TX、链霉素倍半硫酸盐+TX、叶枯酞+TX、硫柳汞+TX、棉褐带卷蛾GV+TX、放射形土壤杆菌+TX、钝绥螨属物种(Amblyseius spp.)+TX、芹菜夜蛾NPV+TX、原樱翅缨小蜂(Anagrus atomus)+TX、短距蚜小蜂(Aphelinus abdominalis)+TX、棉蚜寄生蜂(Aphidius colemani)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)+TX、苜蓿银纹夜蛾NPV+TX、球形芽孢杆菌(Bacillussphaericus Neide)+TX、布氏白僵菌(Beauveria brongniartii)+TX、普通草蛉(Chrysoperla carnea)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)+TX、苹果蠹蛾GV+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)+TX、丽蚜小蜂(Encarsia formosa)+TX、桨角蚜小蜂(Eretmocerus eremicus)+TX、嗜菌异小杆线虫(Heterorhabditis bacteriophora)和大异小杆线虫(H.megidis)+TX、斑长足瓢虫(Hippodamia convergens)+TX、橘粉介壳虫寄生蜂(Leptomastix dactylopii)+TX、盲蝽(Macrolophus caliginosus)+TX、甘蓝夜蛾NPV+TX、黄阔柄跳小蜂(Metaphycus helvolus)+TX、黄绿绿僵菌(Metarhizium anisopliae var.acridum)+TX、金龟子绿僵菌小孢变种(Metarhizium anisopliae var.anisopliae)+TX、欧洲新松叶蜂(Neodiprion sertifer)NPV和红头新松叶蜂(N.lecontei)NPV+TX、小花蝽属物种+TX、玫烟色拟青霉(Paecilomycesfumosoroseus)+TX、智利小植绥螨(Phytoseiulus persimilis)+TX、毛蚊线虫(Steinernema bibionis)+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)+TX、夜蛾斯氏线虫+TX、格氏线虫(Steinernema glaseri)+TX、锐比斯氏线虫(Steinernema riobrave)+TX、Steinernema riobravis+TX、蝼蛄斯氏线虫(Steinernema scapterisci)+TX、斯氏线虫属物种(Steinernema spp.)+TX、赤眼蜂属物种+TX、西方盲走螨(Typhlodromusoccidentalis)+TX、蜡蚧轮枝菌(Verticillium lecanii)+TX、唑磷嗪(apholate)+TX、双(氮丙啶)甲氨基膦硫化物(bisazir)+TX、白消安+TX、迪麦替夫(dimatif)+TX、六甲蜜胺(hemel)+TX、六甲磷(hempa)+TX、甲基涕巴(metepa)+TX、甲硫涕巴(methiotepa)+TX、甲基唑磷嗪(methyl apholate)+TX、不孕啶(morzid)+TX、氟幼脲(penfluron)+TX、涕巴(tepa)+TX、硫代六甲磷(thiohempa)+TX、硫涕巴+TX、曲他胺+TX、尿烷亚胺+TX、(E)-癸-5-烯-1-基乙酸酯与(E)-癸-5-烯-1-醇+TX、(E)-十三碳-4-烯-1-基乙酸酯+TX、(E)-6-甲基庚-2-烯-4-醇+TX、(E,Z)-十四碳-4,10-二烯-1-基乙酸酯+TX、(Z)-十二碳-7-烯-1-基乙酸酯+TX、(Z)-十六碳-11-烯醛+TX、(Z)-十六碳-11-烯-1-基乙酸酯+TX、(Z)-十六碳-13-烯-11-炔-1-基乙酸酯+TX、(Z)-二十-13-烯-10-酮+TX、(Z)-十四碳-7-烯-1-醛+TX、(Z)-十四碳-9-烯-1-醇+TX、(Z)-十四碳-9-烯-1-基乙酸酯+TX、(7E,9Z)-十二碳-7,9-二烯-1-基乙酸酯+TX、(9Z,11E)-十四碳-9,11-二烯-1-基乙酸酯+TX、(9Z,12E)-十四碳-9,12-二烯-1-基乙酸酯+TX、14-甲基十八碳-1-烯+TX、4-甲基壬-5-醇与4-甲基壬-5-酮+TX、α-多纹素+TX、西部松小蠹集合信息素+TX、十二碳二烯醇(codlelure)+TX、可得蒙(codlemone)+TX、诱蝇酮(cuelure)+TX、环氧十九烷+TX、十二碳-8-烯-1-基乙酸酯+TX、十二碳-9-烯-1-基乙酸酯+TX、十二碳-8+TX、10-二烯-1-基乙酸酯+TX、dominicalure+TX、4-甲基辛酸乙酯+TX、丁香酚+TX、南部松小蠹集合信息素(frontalin)+TX、诱杀烯混剂(grandlure)+TX、诱杀烯混剂I+TX、诱杀烯混剂II+TX、诱杀烯混剂III+TX、诱杀烯混剂IV+TX、己诱剂(hexalure)+TX、齿小蠹二烯醇(ipsdienol)+TX、小蠢烯醇(ipsenol)+TX、金龟子性诱剂(japonilure)+TX、三甲基二氧三环壬烷(lineatin)+TX、夜蛾诱剂(litlure)+TX、粉纹夜蛾性诱剂(looplure)+TX、诱杀酯(medlure)+TX、蒙托么克酸(megatomoic acid)+TX、诱虫醚(methyl eugenol)+TX、诱虫烯(muscalure)+TX、十八碳-2,13-二烯-1-基乙酸酯+TX、十八碳-3,13-二烯-1-基乙酸酯+TX、贺康彼(orfralure)+TX、椰蛀犀金龟聚集信息素(oryctalure)+TX、非乐康(ostramone)+TX、诱虫环(siglure)+TX、索迪叮(sordidin)+TX、食菌甲诱醇(sulcatol)+TX、十四碳-11-烯-1-基乙酸酯+TX、地中海实蝇引诱剂(trimedlure)+TX、地中海实蝇引诱剂A+TX、地中海实蝇引诱剂B1+TX、地中海实蝇引诱剂B2+TX、地中海实蝇引诱剂C+TX、创克括(trunc-call)+TX、2-(辛基硫代)乙醇+TX、避蚊酮(butopyronoxyl)+TX、丁氧基(聚丙二醇)+TX、己二酸二丁酯+TX、邻苯二甲酸二丁酯+TX、丁二酸二丁酯+TX、避蚊胺+TX、驱蚊灵(dimethyl carbate)+TX、邻苯二甲酸二甲酯+TX、乙基己二醇+TX、己脲(hexamide)+TX、甲喹丁(methoquin-butyl)+TX、甲基新癸酰胺(methylneodecanamide)+TX、草氨酸盐(oxamate)+TX、派卡瑞丁(picaridin)+TX、1-二氯-1-硝基乙烷+TX、1,1-二氯-2,2-二(4-乙基苯基)乙烷+TX、1,2-二氯丙烷与1,3-二氯丙烯+TX、1-溴-2-氯乙烷+TX、2,2,2-三氯-1-(3,4-二氯苯基)乙基乙酸酯+TX、2,2-二氯乙烯基2-乙基亚磺酰基乙基甲基磷酸酯+TX、2-(1,3-二硫戊环-2-基)苯基二甲基氨基甲酸酯+TX、2-(2-丁氧基乙氧基)乙基硫氰酸酯+TX、2-(4,5-二甲基-1,3-二氧戊环-2-基)苯基甲基氨基甲酸酯+TX、2-(4-氯-3,5-二甲苯基氧基)乙醇+TX、2-氯乙烯基二乙基磷酸酯+TX、2-咪唑啉酮+TX、2-异戊酰茚满-1,3-二酮+TX、2-甲基(丙-2-炔基)氨基苯基甲基氨基甲酸酯+TX、2-氰硫基乙基月桂酸酯+TX、3-溴-1-氯丙-1-烯+TX、3-甲基-1-苯基吡唑-5-基二甲基氨基甲酸酯+TX、4-甲基(丙-2-炔基)氨基-3,5-二甲苯基甲基氨基甲酸酯+TX、5,5-二甲基-3-氧代环己-1-烯基二甲基氨基甲酸酯+TX、阿赛硫磷+TX、丙烯腈+TX、氯甲桥萘+TX、阿洛氨菌素+TX、除害威+TX、α-蜕化素+TX、磷化铝+TX、灭害威+TX、新烟碱+TX、乙基杀扑磷(athidathion)+TX、甲基吡啶磷+TX、苏云金芽孢杆菌δ-内毒素+TX、六氟硅酸钡+TX、多硫化钡+TX、熏菊酯+TX、拜耳22/190+TX、拜耳22408+TX、β-氟氯氰菊酯+TX、β-氯氰菊酯+TX、戊环苄呋菊酯(bioethanomethrin)+TX、生物氯菊酯+TX、双(2-氯乙基)醚+TX、硼砂+TX、溴苯烯磷+TX、溴-DDT+TX、合杀威+TX、畜虫威+TX、特嘧硫磷(butathiofos)+TX、丁酯磷+TX、砷酸钙+TX、氰化钙+TX、二硫化碳+TX、四氯化碳+TX、巴丹盐酸盐+TX、瑟瓦定(cevadine)+TX、冰片丹+TX、氯丹+TX、十氯酮+TX、氯仿+TX、氯化苦+TX、氯腈肟磷+TX、氯吡唑磷(chlorprazophos)+TX、顺式苄呋菊酯(cis-resmethri)+TX、顺式苄呋菊酯(cismethrin)+TX、氰菊酯(clocythrin)+TX、乙酰亚砷酸铜+TX、砷酸铜+TX、油酸铜+TX、畜虫磷(coumithoate)+TX、冰晶石+TX、CS 708+TX、苯腈磷+TX、杀螟腈+TX、环虫菊酯+TX、赛灭磷+TX、d-胺菊酯+TX、DAEP+TX、棉隆+TX、脱甲基克百威(decarbofuran)+TX、除线特(diamidafos)+TX、异氯磷+TX、除线磷+TX、敌来死(dicresyl)+TX、环虫腈+TX、狄氏剂+TX、二乙基5-甲基吡唑-3-基磷酸酯+TX、喘定(dior)+TX、四氟甲醚菊酯+TX、地麦威+TX、苄菊酯+TX、甲基毒虫畏+TX、敌蝇威+TX、丙硝酚+TX、戊硝酚+TX、地乐酚+TX、苯虫醚+TX、蔬果磷+TX、噻喃磷+TX、DSP+TX、脱皮甾酮+TX、EI 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sachalinensis)提取物+TX、α-氯代醇+TX、安妥+TX、碳酸钡+TX、双鼠脲+TX、溴鼠隆+TX、溴敌隆+TX、溴鼠胺+TX、氯鼠酮+TX、胆钙化醇+TX、氯杀鼠灵+TX、克灭鼠+TX、杀鼠萘+TX、杀鼠嘧啶+TX、鼠得克+TX、噻鼠灵+TX、敌鼠+TX、钙化醇+TX、氟鼠灵+TX、氟乙酰胺+TX、氟鼠啶+TX、氟鼠啶盐酸盐+TX、鼠特灵+TX、毒鼠磷+TX、磷+TX、杀鼠酮+TX、灭鼠优+TX、海葱糖苷+TX、氟乙酸钠+TX、硫酸铊+TX、杀鼠灵+TX、2-(2-丁氧基乙氧基)乙基胡椒酸酯+TX、5-(1,3-苯并二氧杂环戊烯-5-基)-3-己基环己-2-烯酮+TX、具有橙花叔醇的法呢醇+TX、增效炔醚+TX、MGK 264+TX、增效醚+TX、增效醛+TX、增效酯(propyl isomer)+TX、S421+TX、增效散+TX、芝麻林素(sesasmolin)+TX、亚砜+TX、蒽醌+TX、环烷酸铜+TX、王铜+TX、二环戊二烯+TX、塞仑+TX、环烷酸锌+TX、福美锌+TX、衣马宁+TX、利巴韦林+TX、氧化汞+TX、甲基托布津+TX、阿扎康唑+TX、联苯三唑醇+TX、糠菌唑+TX、环唑醇+TX、苯醚甲环唑+TX、烯唑醇+TX、氟环唑+TX、腈苯唑+TX、氟喹唑+TX、氟硅唑+TX、粉唑醇+TX、呋吡菌胺+TX、己唑醇+TX、抑霉唑+TX、亚胺唑+TX、种菌唑+TX、叶菌唑+TX、腈菌唑+TX、多效唑+TX、稻瘟酯+TX、戊菌唑+TX、丙硫菌唑+TX、啶斑肟(pyrifenox)+TX、咪鲜胺+TX、丙环唑+TX、啶菌唑+TX、硅氟唑+TX、戊唑醇+TX、氟醚唑+TX、三唑酮+TX、三唑醇+TX、氟菌唑+TX、灭菌唑+TX、嘧啶醇+TX、氯苯嘧啶醇+TX、氟苯嘧啶醇+TX、乙嘧酚磺酸酯(bupirimate)+TX、甲菌定(dimethirimol)+TX、乙菌定(ethirimol)+TX、十二环吗啉+TX、苯锈啶(fenpropidin)+TX、丁苯吗啉+TX、螺环菌胺+TX、十三吗啉+TX、嘧菌环胺+TX、嘧菌胺+TX、嘧霉胺(pyrimethanil)+TX、拌种咯+TX、咯菌腈+TX、苯霜灵(benalaxyl)+TX、呋霜灵(furalaxyl)+TX、甲霜灵+TX、R-甲霜灵+TX、呋酰胺+TX、恶霜灵(oxadixyl)+TX、多菌灵+TX、咪菌威(debacarb)+TX、麦穗宁+TX、噻苯达唑+TX、乙菌利(chlozolinate)+TX、菌核利(dichlozoline)+TX、甲菌利(myclozoline)+TX、腐霉利(procymidone)+TX、乙烯菌核利(vinclozoline)+TX、啶酰菌胺(boscalid)+TX、萎锈灵+TX、甲呋酰胺+TX、氟酰胺(flutolanil)+TX、灭锈胺+TX、氧化萎锈灵+TX、吡噻菌胺(penthiopyrad)+TX、噻呋酰胺+TX、多果定+TX、双胍辛胺+TX、嘧菌酯+TX、醚菌胺+TX、烯肟菌酯+TX、烯肟菌胺+TX、氟菌螨酯+TX、氟嘧菌酯+TX、醚菌酯+TX、苯氧菌胺+TX、肟菌酯+TX、肟醚菌胺+TX、啶氧菌酯+TX、唑菌胺酯+TX、唑胺菌酯+TX、唑菌酯+TX、福美铁+TX、代森锰锌+TX、代森锰+TX、代森联+TX、甲基代森锌+TX、代森锌+TX、敌菌丹(captafol)+TX、克菌丹+TX、唑呋草+TX、灭菌丹+TX、对甲抑菌灵+TX、波尔多混合剂+TX、氧化铜(copper oxide)+TX、代森锰铜(mancopper)+TX、喹啉铜(oxine-copper)+TX、酞菌酯(nitrothal-isopropyl)+TX、克瘟散+TX、异稻瘟净(iprobenphos)+TX、氯瘟磷(phosdiphen)+TX、甲基立枯磷(tolclofos-methyl)+TX、敌菌灵+TX、苯噻菌胺+TX、灭瘟素(blasticidin)-S+TX、地茂散(chloroneb)+TX、百菌清+TX、环氟菌胺+TX、霜脲氰+TX、环丁氟菌胺+TX、双氯氰菌胺(diclocymet)+TX、哒菌酮(diclomezine)+TX、氯硝胺(dicloran)+TX、乙霉威(diethofencarb)+TX、烯酰吗啉+TX、氟吗啉+TX、二噻农(dithianon)+TX、噻唑菌胺(ethaboxam)+TX、土菌灵(etridiazole)+TX、恶唑菌酮+TX、咪唑菌酮(fenamidone)+TX、稻瘟酰胺(fenoxanil)+TX、嘧菌腙(ferimzone)+TX、氟啶胺(fluazinam)+TX、氟吡菌胺(fluopicolide)+TX、磺菌胺(flusulfamide)+TX、氟唑菌酰胺+TX、环酰菌胺+TX、三乙膦酸铝(fosetyl-aluminium)+TX、恶霉灵(hymexazol)+TX、丙森锌+TX、赛座灭(cyazofamid)+TX、磺菌威(methasulfocarb)+TX、苯菌酮+TX、戊菌隆(pencycuron)+TX、苯酞+TX、多氧霉素(polyoxins)+TX、霜霉威(propamocarb)+TX、吡菌苯威+TX、碘喹唑酮(proquinazid)+TX、咯喹酮(pyroquilon)+TX、苯啶菌酮(pyriofenone)+TX、喹氧灵+TX、五氯硝基苯+TX、噻酰菌胺+TX、咪唑嗪(triazoxide)+TX、三环唑+TX、嗪氨灵+TX、有效霉素+TX、缬菌胺+TX、苯酰菌胺(zoxamide)+TX、双炔酰菌胺(mandipropamid)+TX、氟苯醚酰胺+TX、吡唑萘菌胺(isopyrazam)+TX、氟唑环菌胺(sedaxane)+TX、苯并烯氟菌唑+TX、氟唑菌酰羟胺+TX、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3’,4’,5’-三氟-联苯-2-基)-酰胺+TX、异氟环丙胺+TX、异噻菌胺+TX、二吡米曲尼(dipymetitrone)+TX、6-乙基-5,7-二氧代-吡咯并[4,5][1,4]二噻英并[1,2-c]异噻唑-3-甲腈+TX、2-(二氟甲基)-N-[3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+TX、4-(2,6-二氟苯基)-6-甲基-5-苯基-哒嗪-3-甲腈+TX、(R)-3-(二氟甲基)-1-甲基-N-[1,1,3-三甲基茚满-4-基]吡唑-4-甲酰胺+TX、4-(2-溴-4-氟-苯基)-N-(2-氯-6-氟-苯基)-2,5-二甲基-吡唑-3-胺+TX、4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺+TX、氟茚唑菌胺+TX、甲香菌酯(jiaxiangjunzhi)+TX、利本米昔安+TX、二氯苯噻唑+TX、曼德斯宾(mandestrobin)+TX、3-(4,4-二氟-3,4-二氢-3,3-二甲基异喹啉-1-基)喹诺酮+TX、2-[2-氟-6-[(8-氟-2-甲基-3-喹啉基)氧基]苯基]丙-2-醇+TX、噻哌菌灵(oxathiapiprolin)+TX、N-[6-[[[(1-甲基四唑-5-基)-苯基-亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸叔丁酯+TX、联苯吡嗪菌胺(pyraziflumid)+TX、氟虫胺(inpyrfluxam)+TX、氨基甲酸酯类杀菌剂(trolprocarb)+TX、氯氟醚菌唑+TX、一苯三氟康唑(ipfentrifluconazole)+TX、2-(二氟甲基)-N-[(3R)-3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+TX、N'-(2,5-二甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒+TX、N'-[4-(4,5-二氯噻唑-2-基)氧基-2,5-二甲基-苯基]-N-乙基-N-甲基-甲脒+TX、[2-[3-[2-[1-[2-[3,5-双(二氟甲基)吡唑-1-基]乙酰基]-4-哌啶基]噻唑-4-基]-4,5-二氢异噁唑-5-基]-3-氯-苯基]甲磺酸盐+TX、N-[6-[[(Z)-[(1-甲基四唑-5-基)-苯基-亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸丁-3-炔酯+TX、N-[[5-[4-(2,4-二甲基苯基)三唑-2-基]-2-甲基-苯基]甲基]氨基甲酸甲酯+TX、3-氯-6-甲基-5-苯基-4-(2,4,6-三氟苯基)哒嗪+TX、吡啶甲酰氯(pyridachlometyl)+TX、3-(二氟甲基)-1-甲基-N-[1,1,3-三甲基茚满-4-基]吡唑-4-甲酰胺+TX、1-[2-[[1-(4-氯苯基)吡唑-3-基]氧基甲基]-3-甲基-苯基]-4-甲基-四唑-5-酮+TX、1-甲基-4-[3-甲基-2-[[2-甲基-4-(3,4,5-三甲基吡唑-1-基)苯氧基]甲基]苯基]四唑-5-酮+TX、氨基吡芬(aminopyrifen)+TX、唑嘧菌胺+TX、吲唑磺菌胺+TX、氟唑菌苯胺+TX、(Z,2E)-5-[1-(4-氯苯基)吡唑-3-基]氧基-2-甲氧基亚氨基-N,3-二甲基-戊-3-烯胺+TX、氟啶酰菌胺+TX、苯吡克咪徳(fenpicoxamid)+TX、异丁乙氧喹啉+TX、氟苯喹(ipflufenoquin)+TX、奎诺福林(quinofumelin)+TX、异丙噻菌胺+TX、N-[2-[2,4-二氯-苯氧基]苯基]-3-(二氟甲基)-1-甲基-吡唑-4-甲酰胺+TX、N-[2-[2-氯-4-(三氟甲基)苯氧基]苯基]-3-(二氟甲基)-1-甲基-吡唑-4-甲酰胺+TX、苯噻菌酯+TX、氰烯菌酯+TX、5-氨基-1,3,4-噻二唑-2-硫醇锌盐(2:1)+TX、氟吡菌酰胺+TX、氟噻唑菌腈+TX、氟醚菌酰胺+TX、吡丙炔(pyrapropoyne)+TX、哌碳唑(picarbutrazox)+TX、2-(二氟甲基)-N-(3-乙基-1,1-二甲基-茚满-4-基)吡啶-3-甲酰胺+TX、2-(二氟甲基)-N-((3R)-1,1,3-三甲基茚满-4-基)吡啶-3-甲酰胺+TX、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苯甲腈+TX、美特尔特特拉普罗(metyltetraprole)+TX、2-(二氟甲基)-N-((3R)-1,1,3-三甲基茚满-4-基)吡啶-3-甲酰胺+TX、α-(1,1-二甲基乙基)-α-[4'-(三氟甲氧基)[1,1'-二苯基]-4-基]-5-嘧啶甲醇+TX、氟哌啶(fluoxapiprolin)+TX、烯肟菌酯(enoxastrobin)+TX、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苯甲腈+TX、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-硫烷基-1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苯甲腈+TX、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-硫代-4H-1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苯甲腈+TX、抗倒酯+TX、丁香菌酯+TX、中生菌素+TX、噻菌铜+TX、噻唑锌+TX、阿米托林+TX、异菌脲+TX、N-辛基-N'-[2-(辛氨基)乙基]乙烷-1,2-二胺+TX;N'-[5-溴-2-甲基-6-[(1S)-1-甲基-2-丙氧基-乙氧基]-3-吡啶基]-N-乙基-N-甲基-甲脒+TX、N'-[5-溴-2-甲基-6-[(1R)-1-甲基-2-丙氧基-乙氧基]-3-吡啶基]-N-乙基-N-甲基-甲脒+TX、N'-[5-溴-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒+TX、N'-[5-氯-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒+TX、N'-[5-溴-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-异丙基-N-甲基-甲脒+TX(这些化合物可以由WO2015/155075中描述的方法制备);N'-[5-溴-2-甲基-6-(2-丙氧基丙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒+TX(此化合物可以由IPCOM000249876D中描述的方法制备);N-异丙基-N'-[5-甲氧基-2-甲基-4-(2,2,2-三氟-1-羟基-1-苯基-乙基)苯基]-N-甲基-甲脒+TX、N'-[4-(1-环丙基-2,2,2-三氟-1-羟基-乙基)-5-甲氧基-2-甲基-苯基]-N-异丙基-N-甲基-甲脒+TX(这些化合物可以由WO2018/228896中描述的方法制备);N-乙基-N'-[5-甲氧基-2-甲基-4-[2-三氟甲基)氧杂环丁烷-2-基]苯基]-N-甲基-甲脒+TX、N-乙基-N'-[5-甲氧基-2-甲基-4-[2-三氟甲基)四氢呋喃-2-基]苯基]-N-甲基-甲脒+TX(这些化合物可以由WO2019/110427中描述的方法制备);N-[(1R)-1-苄基-3-氯-1-甲基-丁-3-烯基]-8-氟-喹啉-3-甲酰胺+TX、N-[(1S)-1-苄基-3-氯-1-甲基-丁-3-烯基]-8-氟-喹啉-3-甲酰胺+TX、N-[(1R)-1-苄基-3,3,3-三氟-1-甲基-丙基]-8-氟-喹啉-3-甲酰胺+TX、N-[(1S)-1-苄基-3,3,3-三氟-1-甲基-丙基]-8-氟-喹啉-3-甲酰胺+TX、N-[(1R)-1-苄基-1,3-二甲基-丁基]-7,8-二氟-喹啉-3-甲酰胺+TX、N-[(1S)-1-苄基-1,3-二甲基-丁基]-7,8-二氟-喹啉-3-甲酰胺+TX、8-氟-N-[(1R)-1-[(3-氟苯基)甲基]-1,3-二甲基-丁基]喹啉-3-甲酰胺+TX、8-氟-N-[(1S)-1-[(3-氟苯基)甲基]-1,3-二甲基-丁基]喹啉-3-甲酰胺+TX、N-[(1R)-1-苄基-1,3-二甲基-丁基]-8-氟-喹啉-3-甲酰胺+TX、N-[(1S)-1-苄基-1,3-二甲基-丁基]-8-氟-喹啉-3-甲酰胺+TX、N-((1R)-1-苄基-3-氯-1-甲基-丁-3-烯基)-8-氟-喹啉-3-甲酰胺+TX、N-((1S)-1-苄基-3-氯-1-甲基-丁-3-烯基)-8-氟-喹啉-3-甲酰胺+TX(这些化合物可以由WO 2017/153380中描述的方法制备);
1-(6,7-二甲基吡唑并[1,5-a]吡啶-3-基)-4,4,5-三氟-3,3-二甲基-异喹啉+TX、1-(6,7-二甲基吡唑并[1,5-a]吡啶-3-基)-4,4,6-三氟-3,3-二甲基-异喹啉+TX、4,4-二氟-3,3-二甲基-1-(6-甲基吡唑并[1,5-a]吡啶-3-基)异喹啉+TX、4,4-二氟-3,3-二甲基-1-(7-甲基吡唑并[1,5-a]吡啶-3-基)异喹啉+TX、1-(6-氯-7-甲基-吡唑并[1,5-a]吡啶-3-基)-4,4-二氟-3,3-二甲基-异喹啉+TX(这些化合物可以由WO 2017/025510中描述的方法制备);1-(4,5-二甲基苯并咪唑-1-基)-4,4,5-三氟-3,3-二甲基-异喹啉+TX、1-(4,5-二甲基苯并咪唑-1-基)-4,4-二氟-3,3-二甲基-异喹啉+TX、6-氯-4,4-二氟-3,3-二甲基-1-(4-甲基苯并咪唑-1-基)异喹啉+TX、4,4-二氟-1-(5-氟-4-甲基-苯并咪唑-1-基)-3,3-二甲基-异喹啉+TX、3-(4,4-二氟-3,3-二甲基-1-异喹啉基)-7,8-二氢-6H-环戊二烯并[e]苯并咪唑+TX(这些化合物可以由WO 2016/156085中描述的方法制备);N-甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]环丙烷甲酰胺+TX、N,2-二甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺+TX、N-乙基-2-甲基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺+TX、1-甲氧基-3-甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲+TX、1,3-二甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲+TX、3-乙基-1-甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲+TX、N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺+TX、4,4-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮+TX、5,5-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮+TX、1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]吡唑-4-甲酸乙酯+TX、N,N-二甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]-1,2,4-三唑-3-胺+TX。此段落中的化合物可以由WO 2017/055473、WO 2017/055469、WO 2017/093348和WO 2017/118689中描述的方法制备;2-[6-(4-氯苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇+TX(此化合物可以由WO 2017/029179中描述的方法制备);2-[6-(4-溴苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇+TX(此化合物可以由WO2017/029179中描述的方法制备);3-[2-(1-氯环丙基)-3-(2-氟苯基)-2-羟基-丙基]咪唑-4-甲腈+TX(此化合物可以由WO 2016/156290中描述的方法制备);3-[2-(1-氯环丙基)-3-(3-氯-2-氟-苯基)-2-羟基-丙基]咪唑-4-甲腈+TX(此化合物可以由WO 2016/156290中描述的方法制备);2-氨基-6-甲基-吡啶-3-甲酸(4-苯氧基苯基)甲酯+TX(此化合物可以由WO2014/006945中描述的方法制备);2,6-二甲基-1H,5H-[1,4]二噻英并[2,3-c:5,6-c']联吡咯-1,3,5,7(2H,6H)-四酮+TX(此化合物可以由WO 2011/138281中描述的方法制备);N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯硫代甲酰胺+TX;N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺+TX;(Z,2E)-5-[1-(2,4-二氯苯基)吡唑-3-基]氧基-2-甲氧基亚氨基-N,3-二甲基-戊-3-烯胺+TX(此化合物可以由WO 2018/153707中描述的方法制备);N’-(2-氯-5-甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒+TX;N'-[2-氯-4-(2-氟苯氧基)-5-甲基-苯基]-N-乙基-N-甲基-甲脒+TX(此化合物可以由WO 2016/202742中描述的方法制备);2-(二氟甲基)-N-[(3S)-3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+TX(此化合物可以由WO 2014/095675中描述的方法制备);(5-甲基-2-吡啶基)-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲酮+TX、(3-甲基异噁唑-5-基)-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲酮+TX(这些化合物可以由WO 2017/220485中描述的方法制备);2-氧代-N-丙基-2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙酰胺+TX(此化合物可以由WO 2018/065414中描述的方法制备);1-[[5-[5-(三氟甲基)-1,2,4-噁二唑-3-基]-2-噻吩基]甲基]吡唑-4-甲酸乙酯+TX(此化合物可以由WO 2018/158365中描述的方法制备);2,2-二氟-N-甲基-2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙酰胺+TX、N-[(E)-甲氧基亚氨基甲基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺+TX、N-[(Z)-甲氧基亚氨基甲基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺+TX、N-[N-甲氧基-C-甲基-碳酰亚胺基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺+TX(这些化合物可以由WO2018/202428中描述的方法制备)、氯吲哚酰肼+TX、辛菌胺+TX、氯吲哚酰肼+TX、嘧啶类杀菌剂+TX、氟康唑+TX。
在活性成分之后的括号中的参考例如[3878-19-1]是指化学文摘登记号。上文描述的混合配伍物是已知的。在活性成分包括在“The Pesticide Manual[杀有害生物剂手册]”[The Pesticide Manual-AWorld Compendium[杀有害生物剂手册-全球概览];第13版;编辑:C.D.S.TomLin;The British Crop Protection Coimcil[英国农作物保护委员会]]中的情况下,它们在其中以上文对于特定化合物的圆括号中所给出的条目编号来描述;例如化合物“阿维菌素”以条目编号(1)来描述。在“[CCN]”在上文添加到特定化合物的情况下,所述的化合物包括在“Compendium of Pesticide Common Names[杀有害生物剂通用名纲要]”中,其可以在互联网[A.Wood;Compendium of Pesticide Common Names,1995-2004]上获得;例如,化合物“乙酰虫腈”描述于互联网地址http://www.alanwood.net/pesticides/acetoprole.html中。
多数上述活性成分在上文中通过所谓的“通用名”来提及,在单个情形中使用相应的“ISO通用名”或另一“通用名”。若名称不是“通用名”,则所使用的名称种类以特定化合物的圆括号中所给出的名称来代替;在这种情况下,使用IUPAC名称、IUPAC/化学文摘名、“化学名称”、“惯用名”、“化合物名称”或“开发代码”,或若既不使用那些名称之一也不使用“通用名”,则使用“别名”。“CAS登记号”意指化学文摘登记号。
具有式(I)的化合物(选自如表A-1至A-48或B-1至B-40(下文)中所示的一种化合物、或表T1(下文)中列出的化合物1.1至1.98)的活性成分混合物优选地是处于从100:1至1:6000的混合比率,尤其是从50:1至1:50,更尤其是处于从20:1至1:20的比率,甚至更尤其是从10:1至1:10,非常尤其是从5:1和1:5,特别优选的是从2:1至1:2的比率,并且从4:1至2:1的比率同样是优选的,尤其是处于1:1、或5:1、或5:2、或5:3、或5:4、或4:1、或4:2、或4:3、或3:1、或3:2、或2:1、或1:5、或2:5、或3:5、或4:5、或1:4、或2:4、或3:4、或1:3、或2:3、或1:2、或1:600、或1:300、或1:150、或1:35、或2:35、或4:35、或1:75、或2:75、或4:75、或1:6000、或1:3000、或1:1500、或1:350、或2:350、或4:350、或1:750、或2:750、或4:750的比率。那些混合比率是按重量计的。
如上所述的混合物可以被用于控制有害生物的方法中,该方法包括将包含如上所述的混合物的组合物施用于有害生物或其环境中,通过手术或疗法用于处理人或动物体的方法以及在人或动物体上实施的诊断方法除外。
包含如表A-1至A-48或B-1至B-40(下文)中所示的化合物、或表T1(下文)中列出的化合物1.1至1.98,以及一种或多种如上所述的活性成分的混合物可以例如以单一的“掺水即用”的形式施用,以组合的喷雾混合物(该混合物由单一活性成分组分的单独配制品构成)(如“桶混制剂”)施用,并且当以顺序的方式(即,一个在另一个适度短的时期之后,如几小时或几天)施用时组合使用这些单一活性成分来施用。施用如表A-1至A-48或B-1至B-40(下文)中所示的化合物、或表T1(下文)中列出的化合物1.1至1.98以及一种或多种如上所述的活性成分的顺序对于实施本发明不是至关重要的。
本发明的化合物也可以与驱蠕虫药剂组合使用。此类驱蠕虫药剂包括选自大环内酯类化合物的化合物,如伊维菌素、阿维菌素、阿巴美丁、依马克丁、依立诺克丁、多拉克汀、司拉克丁、莫昔克丁、奈马克丁以及米尔倍霉素衍生物,如在EP-357460、EP-444964以及EP-594291中所述。另外的驱蠕虫药剂包括半合成及生物合成阿维菌素/米尔倍霉素衍生物,如在US-5015630、WO-9415944以及WO-9522552中所述的那些。另外的驱蠕虫药剂包括苯并咪唑类,如阿苯达唑、坎苯达唑、芬苯达唑、氟苯达唑、甲苯达唑、奥芬达唑、奥苯达唑、帕苯达唑以及该类别的其他成员。另外的驱蠕虫药剂包括咪唑并噻唑类以及四氢嘧啶类,如四咪唑、左旋咪唑、双羟萘酸噻嘧啶、奥克太尔或莫仑太尔。另外的驱蠕虫药剂包括杀吸虫剂(如三氯苯达唑和氯舒隆)以及杀绦虫剂(如吡喹酮和依西太尔)。
本发明的化合物可以与对郝青酰胺(paraherquamide)/马可氟汀(marcfortine)类驱蠕虫药剂的衍生物及类似物以及抗寄生虫剂噁唑啉(如在US-5478855、US-4639771和DE-19520936中所披露的那些)组合使用。
本发明的化合物可以与如WO 96/15121中所述的一般种类二氧代吗啉抗寄生虫剂的衍生物及类似物以及还与驱蠕虫活性的环状缩酚肽(如WO 96/11945、WO 93/19053、WO93/25543、EP 0 626 375、EP 0 382 173、WO 94/19334、EP 0 382 173和EP 0 503 538中所述的那些)组合使用。
本发明的化合物可以与其他杀外寄生虫药(ectoparasiticide)组合使用;例如,氟虫腈;拟除虫菊酯;有机磷酸酯;昆虫生长调节剂如氯芬奴隆;蜕皮激素激动剂如虫酰肼等;新烟碱类如吡虫啉等。
本发明的化合物可以与萜烯生物碱类组合使用,例如国际专利申请公开号WO 95/19363或WO 04/72086中所述的那些,特别是其中所披露的化合物。
可以与本发明的化合物组合使用的此类生物活性化合物的其他实例包括但不限于以下:
有机磷酸酯:乙酰甲胺磷、甲基吡噁磷、乙基谷硫磷、甲基谷硫磷、溴硫磷、乙基溴硫磷、硫线磷、四氯乙磷(chlorethoxyphos)、毒死蜱、氯芬磷、氯甲磷、内吸磷、内吸磷-S-甲基、内吸磷-S-甲基砜、氯亚胺硫磷、二嗪磷、敌敌畏、百治磷、乐果、乙拌磷、乙硫磷、灭线磷、氧嘧啶磷、伐灭磷、苯线磷、杀螟硫磷、丰索磷、倍硫磷、吡氟硫磷、地虫磷、安果、噻唑磷、庚烯磷、氯唑磷、异拌磷、异噁唑磷、马拉硫磷、虫螨畏、甲胺磷、杀扑磷、甲基对硫磷、速灭磷、久效磷、二溴磷、氧乐果、甲基氧代内吸磷、对氧磷、对硫磷、甲基对硫磷、稻丰散、伏杀硫磷、硫环磷、磷虫威、亚胺硫磷、磷胺、甲拌磷、肟硫磷、嘧啶磷、嘧啶磷-甲基、丙溴磷、丙虫磷、proetamphos、丙硫磷、吡唑硫磷、哒嗪硫磷、喹硫磷、硫丙磷、替美磷、特丁磷、丁基嘧啶磷、司替罗磷、二甲硫吸磷(thimeton)、三唑磷、敌百虫、灭蚜硫磷。
氨基甲酸酯:棉铃威、涕灭威、2-仲丁苯基甲基氨基甲酸酯、丙硫克百威、甲萘威、克百威、丁硫克百威、地虫威、乙硫苯威、苯氧威、芬硫克、呋线威、HCN-801、异丙威、茚虫威、灭虫威、灭多虫、5-甲基-间-异丙苯基丁炔基(甲基)氨基甲酸酯、杀线威、抗蚜威、残杀威、硫双威、久效威、唑蚜威、UC-51717。
拟除虫菊酯:氟丙菊酯、烯丙菊酯、顺式氯氰菊酯、5-苄基-3-呋喃甲基(E)-(1R)-顺式-2,2-二甲基-3-(2-氧代硫杂环戊烷-3-亚基甲基)环丙烷甲酸酯、联苯菊酯、β-氟氯氰菊酯、氟氯氰菊酯、a-氯氰菊酯、β-氯氰菊酯、生物丙烯菊酯、生物丙烯菊酯((S)-环戊基异构体)、生物苄呋菊酯、联苯菊酯、NCI-85193、乙氰菊酯、氯氟氰菊酯、氯氰菊酯、苯氰菊酯、溴氰菊酯、烯炔菊酯、高氰戊菊酯、醚菊酯、五氟苯菊酯、甲氰菊酯、氰戊菊酯、氟氰戊菊酯、氟氯苯菊酯、氟胺氰菊酯(D异构体)、炔咪菊酯、氯氟氰菊酯、λ-氯氟氰菊酯、苄氯菊酯、苯醚菊酯、炔丙菊酯、除虫菊酯(天然产物)、苄呋菊酯、胺菊酯、四氟苯菊酯、θ-氯氰菊酯、氟硅菊酯、t-氟胺氰菊酯、七氟菊酯、四溴菊酯、ζ-氯氰菊酯。
节肢动物生长调节剂:a)甲壳质合成抑制剂:苯甲酰脲:定虫隆、除虫脲、啶蜱脲、氟螨脲、氟虫脲、氟铃脲、氯芬奴隆、双苯氟脲、伏虫脲、杀虫脲、噻嗪酮、苯虫醚、噻螨酮、乙螨唑、四螨嗪(chlorfentazine);b)蜕皮激素拮抗剂:氯虫酰肼、甲氧虫酰肼、虫酰肼;c)保幼激素类似物:吡丙醚、烯虫酯(包括S-烯虫酯)、苯氧威;d)脂质生物合成抑制剂:螺螨酯。
其他抗寄生虫药:灭螨醌、双甲脒、AKD-1022、ANS-118、印楝素、苏云金杆菌、杀虫磺、联苯肼酯、乐杀螨、溴螨酯、BTG-504、BTG-505、毒杀芬、杀螟丹、乙酯杀螨醇、杀虫脒、溴虫腈、环虫酰肼、噻虫胺、赛灭净、敌克隆登(diacloden)、杀螨隆、DBI-3204、二活菌素、二羟基甲基二羟基吡咯烷、敌螨通、敌螨普、硫丹、乙虫腈、醚菊酯、喹螨醚、氟螨嗪(flumite)、MTI-800、唑螨酯、嘧螨酯、氟螨噻、溴氟菊酯、氟螨嗪、三氟醚、苄螨醚(fluproxyfen)、苄螨醚(halofenprox)、氟蚁腙、IKI-220、水硅钠石、NC-196、印度薄荷草(neem guard)、尼敌诺特呋喃(nidinorterfuran)、烯啶虫胺、SD-35651、WL-108477、啶虫丙醚、克螨特、普罗芬布特(protrifenbute)、吡蚜酮、哒螨酮、嘧螨醚、NC-1111、R-195、RH-0345、RH-2485、RYI-210、S-1283、S-1833、SI-8601、氟硅菊酯、硅罗玛汀(silomadine)、多杀菌素、吡螨胺、三氯杀螨砜、四抗菌素、噻虫啉、杀虫环、噻虫嗪、唑虫酰胺、唑蚜威、三乙多杀菌素、三活菌素、增效炔醚、波塔雷克(vertalec)、YI-5301。
生物剂:苏云金芽孢杆菌亚莎华亚种(Bacillus thuringiensis ssp aizawai)、苏云金芽孢杆菌库斯塔克亚种(kurstaki)、苏云金芽孢杆菌δ内毒素、杆状病毒、昆虫病原细菌、病毒以及真菌。
杀细菌剂:金霉素、土霉素、链霉素。
其他生物剂:恩氟沙星、非班太尔、喷沙西林、美洛昔康、头孢氨苄、卡那霉素、匹莫苯、克仑特罗、奥美拉唑、硫姆林、贝那普利、皮瑞普(pyriprole)、头孢喹肟、氟苯尼考、布舍瑞林、头孢维星、托拉菌素、头孢噻呋、卡洛芬、美氟腙、吡喹酮、三氯苯达唑。
根据本发明的组合物还可以包含另外的固体或液体助剂,如稳定剂,例如未环氧化的或环氧化的植物油(例如环氧化的椰子油、菜籽油或大豆油),消泡剂(例如硅酮油),防腐剂,粘度调节剂,粘合剂和/或增粘剂,肥料或其他用于获得特定效果的活性成分,例如杀细菌剂、杀真菌剂、杀线虫剂、植物活化剂、杀软体动物剂或除草剂。
根据本发明的组合物是以本身已知的方式,在不存在助剂的情况下,例如通过研磨、筛选和/或压缩固体活性成分;和在至少一种助剂存在下,例如通过紧密混合活性成分与一种或多种助剂和/或将活性成分与一种或多种助剂一起研磨来制备。用于制备组合物的这些方法和用于制备这些组合物的化合物(I)的用途也是本发明的主题。
本发明的另一个方面涉及具有式(I)的化合物的或优选的如本文所定义的单独化合物的、包含至少一种具有式(I)的化合物或至少一种优选的如以上定义的单独化合物的组合物的、或包含至少一种具有式(I)的化合物或至少一种优选的如以上定义的单独化合物(与如上所述的其他杀真菌剂或杀昆虫剂混合)的杀真菌或杀昆虫混合物的用于控制或预防植物(例如有用植物(如作物植物))、其繁殖材料(例如种子)、收获的作物(例如收获的粮食作物)、或非生命材料被昆虫或植物病原性微生物(优选真菌有机体)侵染的用途。
本发明的另一方面涉及控制或预防植物(例如有用植物(如作物植物))、其繁殖材料(例如种子)、收获的作物(例如收获的粮食作物)、或非生命材料被昆虫或植物病原性或腐败微生物或对人潜在有害的有机体(尤其是真菌有机体)侵染的方法,所述方法包括将具有式(I)的化合物或优选的如以上定义的个别化合物作为活性成分施用至所述植物、所述植物的部分或其场所、其繁殖材料、或所述非生命材料的任何部分。
控制或预防意指被植物病原性或腐败微生物或对人潜在有害的有机体(尤其是真菌有机体)的侵染减少至这样一个被证明改进的水平。
控制或预防作物植物被植物病原性微生物(尤其是真菌生物体)或昆虫侵染的优选的方法是叶面施用,该方法包括施用具有式(I)的化合物、或含有至少一种所述化合物的农用化学组合物。施用频率和施用比率将取决于受相应的病原体或昆虫侵染的风险。然而,具有式(I)的化合物还可以通过用液体配制品湿透植物的场所或者通过将处于固体形式的化合物例如以颗粒形式施用到土壤(土壤施用)而经由土壤通过根(内吸作用)渗透植物。在水稻作物中,可以将此类颗粒剂施用至灌水的稻田中。具有式(I)的化合物也可以通过以下方式施用于种子(包衣):将种子或块茎用杀真菌剂的液体配制品浸渍,或用固体配制品对它们包衣。
配制品(例如含有具有式(I)的化合物、以及(如果希望的话)固体或液体辅助剂或用于包囊具有式(I)的化合物的单体的组合物)可以按已知方式制备,典型地通过将化合物与增充剂(例如溶剂、固体载体以及任选地表面活性化合物(表面活性剂))进行密切地混合和/或研磨。
有利的施用比率通常是从5g至2kg的活性成分(a.i.)/公顷(ha),优选从10g至1kga.i./ha,最优选从20g至600g a.i./ha。当作为种子浸泡试剂使用时,适当的剂量是从10mg至1g活性物质/kg种子。
当本发明所述的组合用于处理种子时,比率为0.001至50g具有式(I)的化合物/kg种子、优选从0.01至10g/kg种子,这一般是足够的。
适当地,预防性(意指在疾病发展之前)或治愈性(意指疾病发展之后)施用包含根据本发明的具有式(I)的化合物的组合物。
本发明的组合物能以任何常规形式使用,例如,以双包装、干种子处理用的粉剂(DS)、种子处理用的乳液(ES)、种子处理用的可流动浓缩物(FS)、种子处理用的溶液(LS)、种子处理用的水分散性粉剂(WS)、种子处理用的胶囊悬浮液(CF)、种子处理用的凝胶(GF)、乳液浓缩物(EC)、悬浮液浓缩物(SC)、悬浮乳液(SE)、胶囊悬浮液(CS)、水分散性颗粒(WG)、可乳化性颗粒(EG)、油包水型乳液(EO)、水包油型乳液(EW)、微乳液(ME)、油分散剂(OD)、油悬剂(OF)、油溶性液剂(OL)、可溶性浓缩物(SL)、超低容量悬浮剂(SU)、超低容量液剂(UL)、母药(TK)、可分散性浓缩物(DC)、可湿性粉剂(WP)或与农业上可接受的辅助剂组合的任何技术上可行的配制品的形式。
能以常规方式生产此类组合物,例如通过混合活性成分与适当的配制品惰性剂(稀释剂、溶剂、填充剂及任选地其他配制成分,如表面活性剂、杀生物剂、防冻剂、粘着剂、增稠剂及提供辅助效果的化合物)。还可以使用旨在长期持续功效的常规缓释配制品。特别地,有待以喷雾形式(如水分散性浓缩物(例如EC、SC、DC、OD、SE、EW、EO等)、可湿性粉剂及颗粒)施用的配制品可以含有表面活性剂(如湿润剂和分散剂)及提供辅佐效果的其他化合物,例如甲醛与萘磺酸盐、烷基芳基磺酸盐、木质素磺酸盐、脂肪烷基硫酸盐及乙氧基化烷基酚和乙氧基化脂肪醇的缩合产物。
使用本发明的组合及稀释剂,以合适的拌种配制品形式,例如具有对种子的良好粘着性的水性悬浮液或干粉剂形式,用本身已知的方式将拌种配制品施用至种子。此类拌种配制品在本领域是已知的。拌种配制品可以含有包囊形式的单一活性成分或活性成分的组合,例如作为缓释胶囊或微胶囊。
通常,这些配制品包括按重量计从0.01%至90%的活性剂、从0至20%的农业上可接受的表面活性剂及10%至99.99%的固体或液体配制惰性剂和一种或多种辅助剂,该活性剂由至少具有式(I)的化合物任选地连同其他活性剂(特别是杀微生物剂或防腐剂等)一起组成。组合物的浓缩形式通常含有按重量计在约2%与80%之间、优选在约5%与70%之间的活性剂。配制品的施用形式可以例如含有按重量计从0.01%至20%、优选按重量计从0.01%至5%的活性剂。然而商用的产品将优选地被配制为浓缩物,最终使用者将通常使用稀释的配制品。
然而优选的是将商用的产品配制为浓缩物,最终使用者将通常使用稀释的配制品。
根据下表A-1至A-48和B-1至B-40的化合物可以根据以上描述的方法制备。随后的这些实例旨在说明本发明并且展示优选的具有式(I)的化合物。
表A:此表披露了根据本发明的具有式(Ia)的化合物的64个取代基定义(G):
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其中根据本发明的具有式(I)的化合物的G(包含-N(H)-、R4、R5、R6、R7、R8和L1)是
并且其中G取代基是如下所定义的:
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因此,以下化合物在表A-1至A-48中进行了具体描述了,其中式(Ia)的取代基如下:
表A-1:此表提供了64种具有式(Ia)的化合物A-1.01至A-1.64,其中R9是3-环丙基苯基,R1是氢,R2是甲基,R3是氢,并且G取代基是如上表A中所定义的。
例如,化合物A-1.23具有以下结构:
表A-2:此表提供了64种具有式(Ia)的化合物A-2.01至A-2.64,其中R9是3-甲基苯基,R1是氢,R2是甲基,R3是氢,并且G取代基是如上表A中所定义的。
表A-3:此表提供了64种具有式(Ia)的化合物A-3.01至A-3.64,其中R9是3-(三氟甲基)苯基,R1是氢,R2是甲基,R3是氢,并且G取代基是如上表A中所定义的。
例如,化合物A-3.23具有以下结构:
表A-4:此表提供了64种具有式(Ia)的化合物A-4.01至A-4.64,其中R9是苯基,R1是氢,R2是甲基,R3是氢,并且G取代基是如上表A中所定义的。
表A-5:此表提供了64种具有式(Ia)的化合物A-5.01至A-5.64,其中R9是3-环丙基苯基,R1是氢,R2是氯,R3是氢,并且G取代基是如上表A中所定义的。
表A-6:此表提供了64种具有式(Ia)的化合物A-6.01至A-6.64,其中R9是3-甲基苯基,R1是氢,R2是氯,R3是氢,并且G取代基是如上表A中所定义的。
表A-7:此表提供了64种具有式(Ia)的化合物A-7.01至A-7.64,其中R9是3-(三氟甲基)苯基,R1是氢,R2是氯,R3是氢,并且G取代基是如上表A中所定义的。
表A-8:此表提供了64种具有式(Ia)的化合物A-8.01至A-8.64,其中R9是苯基,R1是氢,R2是氯,R3是氢,并且G取代基是如上表A中所定义的。
表A-9:此表提供了64种具有式(Ia)的化合物A-9.1至A-9.64,其中R9是3-环丙基苯基,R1是氢,R2是氢,R3是氯,并且G取代基是如上表A中所定义的。
例如,化合物A-9.59具有以下结构:
表A-10:此表提供了64种具有式(Ia)的化合物A-10.1至A-10.64,其中R9是3-甲基苯基,R1是氢,R2是氢,R3是氯,并且G取代基是如上表A中所定义的。
表A-11:此表提供了8种具有式(Ia)的化合物A-11.23和A-11.58至A-11.64,其中R9是3-环丙基苯基,R1是甲基,R2是氢,R3是氢,并且G取代基是如上表A中所定义的。
表A-12:此表提供了8种具有式(Ia)的化合物A-12.23和A-12.58至A-12.64,其中R9是3-甲基苯基,R1是甲基,R2是氢,R3是氢,并且G取代基是如上表A中所定义的。
表A-13:此表提供了8种具有式(Ia)的化合物A-13.23和A-13.58至A-13.64,其中R9是3-环丙基苯基,R1是甲氧基,R2是氢,R3是氢,并且G取代基是如上表A中所定义的。
表A-14:此表提供了8种具有式(Ia)的化合物A-14.23和A-14.58至A-14.64,其中R9是3-甲基苯基,R1是甲氧基,R2是氢,R3是氢,并且G取代基是如上表A中所定义的。
表A-15:此表提供了8种具有式(Ia)的化合物A-15.23和A-15.58至A-15.64,其中R9是3-环丙基苯基,R1是氢,R2是氰基,R3是氢,并且G取代基是如上表A中所定义的。
表A-16:此表提供了8种具有式(Ia)的化合物A-16.23和A-16.58至A-16.64,其中R9是3-甲基苯基,R1是氢,R2是氰基,R3是氢,并且G取代基是如上表A中所定义的。
表A-17:此表提供了64种具有式(Ia)的化合物A-17.1至A-17.64,其中R9是3-环丙基苯基,R1是氢,R2是氢,R3是氢,并且G取代基是如上表A中所定义的。
表A-18:此表提供了64种具有式(Ia)的化合物A-18.1至A-18.64,其中R9是3-甲基苯基,R1是氢,R2是氢,R3是氢,并且G取代基是如上表A中所定义的。
表A-19:此表提供了8种具有式(Ia)的化合物A-19.23和A-19.58至A-19.64,其中R9是3-环丙基苯基,R1是氢,R2是氢,R3是溴,并且G取代基是如上表A中所定义的。
表A-20:此表提供了8种具有式(Ia)的化合物A-20.23和A-20.58至A-20.64,其中R9是3-甲基苯基,R1是氢,R2是氢,R3是溴,并且G取代基是如上表A中所定义的。
表A-21:此表提供了64种具有式(Ia)的化合物A-21.1至A-21.64,其中R9是3-环丙基苯基,R1是氢,R2是氢,R3是氰基,并且G取代基是如上表A中所定义的。
表A-22:此表提供了64种具有式(Ia)的化合物A-22.1至A-22.64,其中R9是3-甲基苯基,R1是氢,R2是氢,R3是氰基,并且G取代基是如上表A中所定义的。
表A-23:此表提供了64种具有式(Ia)的化合物A-23.1至A-23.64,其中R9是3-环丙基苯基,R1是氢,R2是氢,R3是氟,并且G取代基是如上表A中所定义的。
表A-24:此表提供了64种具有式(Ia)的化合物A-24.1至A-24.64,其中R9是3-甲基苯基,R1是氢,R2是氢,R3是氟,并且G取代基是如上表A中所定义的。
表A-25:此表提供了8种具有式(Ia)的化合物A-25.23和A-25.58至A-25.64,其中R9是3-环丙基苯基,R1是氢,R2是甲氧基,R3是氢,并且G取代基是如上表A中所定义的。
表A-26:此表提供了8种具有式(Ia)的化合物A-26.23和A-26.58至A-26.64,其中R9是3-甲基苯基,R1是氢,R2是甲氧基,R3是氢,并且G取代基是如上表A中所定义的。
表A-27:此表提供了8种具有式(Ia)的化合物A-27.23和A-27.58至A-27.64,其中R9是3-环丙基苯基,R1是氢,R2是环丙基,R3是氢,并且G取代基是如上表A中所定义的。
例如,化合物A-27.23具有以下结构:
表A-28:此表提供了8种具有式(Ia)的化合物A-28.27和A-28.58至A-28.64,其中R9是3-甲基苯基,R1是氢,R2是环丙基,R3是氢,并且G取代基是如上表A中所定义的。
表A-29:此表提供了8种具有式(Ia)的化合物A-29.27和A-29.58至A-29.64,其中R9是3-环丙基苯基,R1是氢,R2是溴,R3是氢,并且G取代基是如上表A中所定义的。
表A-30:此表提供了8种具有式(Ia)的化合物A-30.27和A-30.58至A-30.64,其中R9是3-甲基苯基,R1是氢,R2是溴,R3是氢,并且G取代基是如上表A中所定义的。
表A-31:此表提供了8种具有式(Ia)的化合物A-31.27和A-31.58至A-31.64,其中R9是3-环丙基苯基,R1是氢,R2是氟,R3是氢,并且G取代基是如上表A中所定义的。
表A-32:此表提供了8种具有式(Ia)的化合物A-32.27和A-32.58至A-32.64,其中R9是3-甲基苯基,R1是氢,R2是氟,R3是氢,并且G取代基是如上表A中所定义的。
表A-33:此表提供了8种具有式(Ia)的化合物A-33.27和A-33.58至A-33.64,其中R9是3-环丙基苯基,R1是氢,R2是三氟甲基,R3是氢,并且G取代基是如上表A中所定义的。
表A-34:此表提供了8种具有式(Ia)的化合物A-34.27和A-34.58至A-34.64,其中R9是3-甲基苯基,R1是氢,R2是三氟甲基,R3是氢,并且G取代基是如上表A中所定义的。
表A-35:此表提供了8种具有式(Ia)的化合物A-35.27和A-35.58至A-35.64,其中R9是3-环丙基苯基,R1是氢,R2是甲基硫烷基,R3是氢,并且G取代基是如上表A中所定义的。
表A-36:此表提供了8种具有式(Ia)的化合物A-36.27和A-36.58至A-36.64,其中R9是3-甲基苯基,R1是氢,R2是甲基硫烷基,R3是氢,并且G取代基是如上表A中所定义的。
表A-37:此表提供了8种具有式(Ia)的化合物A-37.27和A-37.58至A-37.64,其中R9是3-环丙基苯基,R1是氢,R2是甲基磺酰基,R3是氢,并且G取代基是如上表A中所定义的。
表A-38:此表提供了8种具有式(Ia)的化合物A-38.27和A-38.58至A-38.64,其中R9是3-甲基苯基,R1是氢,R2是甲基磺酰基,R3是氢,并且G取代基是如上表A中所定义的。
表A-39:此表提供了8种具有式(Ia)的化合物A-39.27和A-39.58至A-39.64,其中R9是3-环丙基苯基,R1是氯,R2是甲基,R3是氢,并且G取代基是如上表A中所定义的。
表A-40:此表提供了8种具有式(Ia)的化合物A-40.27和A-40.58至A-40.64,其中R9是3-甲基苯基,R1是氯,R2是甲基,R3是氢,并且G取代基是如上表A中所定义的。
表A-41:此表提供了8种具有式(Ia)的化合物A-41.27和A-41.58至A-41.64,其中R9是3-环丙基苯基,R1是甲基,R2是氯,R3是氢,并且G取代基是如上表A中所定义的。
表A-42:此表提供了8种具有式(Ia)的化合物A-42.27和A-42.58至A-42.64,其中R9是3-甲基苯基,R1是甲基,R2是氯,R3是氢,并且G取代基是如上表A中所定义的。
表A-43:此表提供了64种具有式(Ia)的化合物A-43.1至A-43.64,其中R9是3-环丙基苯基,R1是氢,R2是氢,R3是甲基,并且G取代基是如上表A中所定义的。
表A-44:此表提供了64种具有式(Ia)的化合物A-44.1至A-44.64,其中R9是3-甲基苯基,R1是氢,R2是氢,R3是甲基,并且G取代基是如上表A中所定义的。
表A-45:此表提供了64种具有式(Ia)的化合物A-45.01至A-45.64,其中R9是3-环丙基苯基,R1是氢,R2是氢,R3是甲氧基,并且G取代基是如上表A中所定义的。
表A-46:此表提供了64种具有式(Ia)的化合物A-46.01至A-46.64,其中R9是3-甲基苯基,R1是氢,R2是氢,R3是甲氧基,并且G取代基是如上表A中所定义的。
表A-47:此表提供了64种具有式(Ia)的化合物A-47.01至A-47.64,其中R9是3-(三氟甲基)苯基,R1是氢,R2是氢,R3是甲氧基,并且G取代基是如上表A中所定义的。
表A-48:此表提供了64种具有式(Ia)的化合物A-48.01至A-48.64,其中R9是苯基,R1是氢,R2是氢,R3是甲氧基,并且G取代基是如上表A中所定义的。
通过进一步解释,在表A-1至A-48中,其中化合物被标识为,例如化合物A-1.01,这定义了具有式(Ia)的化合物,该化合物具有如表A-1中描述的R1、R2、R3和R9取代基,以及上表A中编号为“1”的G取代基,化合物A-1.02、A-1.03等以此类推。相同的考虑适用于下表B-1至B-40中披露的化合物。
表B:此表披露了根据本发明的具有式(Ia)的化合物的41个取代基定义(R9):
其中根据本发明的具有式(I)的化合物的G(包含-N(H)-、R4、R5、R6、R7、R8和L1)是
并且其中R9取代基是如下所定义的:
因此,以下化合物在表B-1至B-40中进行了具体描述了,其中式(Ia)的取代基如下:
表B-1:此表提供了41种具有式(Ia)的化合物B-1.01至B-1.41,其中R1是氢,R2是甲基,R3是氢,G是[2-(2,4-二氯苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
例如,化合物B-1.05和B-1.06具有以下结构:
表B-2:此表提供了41种具有式(Ia)的化合物B-2.01至B-2.41,其中R1是氢,R2是甲基,R3是氢,G是[2-(2,4-二氯苯基)乙基氨基],并且R9取代基是如上表B中所定义的。
表B-3:此表提供了41种具有式(Ia)的化合物B-3.01至B-3.41,其中R1是氢,R2是甲基,R3是氢,G是[2-(2,4-二氯苯基)-2,2-二氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-4:此表提供了41种具有式(Ia)的化合物B-4.01至B-4.41,其中R1是氢,R2是氯,R3是氢,G是[2-(2,4-二氯苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-5:此表提供了41种具有式(Ia)的化合物B-5.01至B-5.41,其中R1是氢,R2是氯,R3是氢,G是[2-(2,4-二氯苯基)-2,2-二氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-6:此表提供了41种具有式(Ia)的化合物B-6.01至B-6.41,其中R1是氢,R2是氯,R3是氢,G是[2-(2,4-二氯苯基)乙基氨基],并且R9取代基是如上表B中所定义的。
表B-7:此表提供了41种具有式(Ia)的化合物B-7.01至B-7.41,其中R1是氢,R2是甲基,R3是氢,G是[2-(2,4-二甲基苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-8:此表提供了41种具有式(Ia)的化合物B-8.01至B-8.41,其中R1是氢,R2是甲基,R3是氢,G是[2-(2,4-二甲基苯基)乙基氨基],并且R9取代基是如上表B中所定义的。
表B-9:此表提供了41种具有式(Ia)的化合物B-9.01至B-9.41,其中R1是氢,R2是甲基,R3是氢,G是[2-(2,4-二甲基苯基)-2,2-二氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-10:此表提供了41种具有式(Ia)的化合物B-10.01至B-10.41,其中R1是氢,R2是氯,R3是氢,G是[2-(2,4-二甲基苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-11:此表提供了41种具有式(Ia)的化合物B-11.01至B-11.41,其中R1是氢,R2是氯,R3是氢,G是[2-(2,4-二甲基苯基)乙基氨基],并且R9取代基是如上表B中所定义的。
表B-12:此表提供了41种具有式(Ia)的化合物B-12.01至B-12.41,其中R1是氢,R2是氯,R3是氢,G是[2-(2,4-二甲基苯基)-2,2-二氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-13:此表提供了41种具有式(Ia)的化合物B-13.01至B-13.41,其中R1是氢,R2是氢,R3是氟,G是[2-(2,4-二氯苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-14:此表提供了41种具有式(Ia)的化合物B-14.01至B-14.41,其中R1是氢,R2是氢,R3是氟,G是[2-(2,4-二氯苯基)乙基氨基],并且R9取代基是如上表B中所定义的。
表B-15:此表提供了41种具有式(Ia)的化合物B-15.01至B-15.41,其中R1是氢,R2是氢,R3是氟,G是[2-(2,4-二氯苯基)-2,2-二氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-16:此表提供了41种具有式(Ia)的化合物B-16.01至B-16.41,其中R1是氢,R2是氢,R3是甲基,G是[2-(2,4-二氯苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-17:此表提供了41种具有式(Ia)的化合物B-17.01至B-17.41,其中R1是氢,R2是氢,R3是甲基,G是[2-(2,4-二氯苯基)乙基氨基],并且R9取代基是如上表B中所定义的。
表B-18:此表提供了41种具有式(Ia)的化合物B-18.01至B-18.41,其中R1是氢,R2是氢,R3是甲基,G是[2-(2,4-二氯苯基)-2,2-二氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-19:此表提供了41种具有式(Ia)的化合物B-19.01至B-19.41,其中R1是氢,R2是氢,R3是氟,G是[2-(2,4-二甲基苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-20:此表提供了41种具有式(Ia)的化合物B-20.01至B-20.41,其中R1是氢,R2是氢,R3是氟,G是[2-(2,4-二甲基苯基)乙基氨基],并且R9取代基是如上表B中所定义的。
表B-21:此表提供了41种具有式(Ia)的化合物B-21.01至B-21.41,其中R1是氢,R2是氢,R3是氟,G是[2-(2,4-二甲基苯基)-2,2-二氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-22:此表提供了41种具有式(Ia)的化合物B-22.01至B-22.41,其中R1是氢,R2是氢,R3是甲基,G是[2-(2,4-二甲基苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-23:此表提供了41种具有式(Ia)的化合物B-23.01至B-23.41,其中R1是氢,R2是氢,R3是甲基,G是[2-(2,4-二甲基苯基)乙基氨基],并且R9取代基是如上表B中所定义的。
表B-24:此表提供了41种具有式(Ia)的化合物B-24.01至B-24.41,其中R1是氢,R2是氢,R3是甲基,G是[2-(2,4-二甲基苯基)-2,2-二氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-25:此表提供了41种具有式(Ia)的化合物B-25.01至B-25.41,其中R1是氢,R2是氢,R3是甲氧基,G是[2-(2,4-二氯苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-26:此表提供了41种具有式(Ia)的化合物B-26.01至B-26.41,其中R1是氢,R2是氢,R3是甲氧基,G是[2-(2,4-二氯苯基)乙基氨基],并且R9取代基是如上表B中所定义的。
表B-27:此表提供了41种具有式(Ia)的化合物B-27.01至B-27.41,其中R1是氢,R2是氢,R3是甲氧基,G是[2-(2,4-二氯苯基)-2,2-二氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-28:此表提供了41种具有式(Ia)的化合物B-28.01至B-28.41,其中R1是氢,R2是氢,R3是甲氧基,G是[2-(2,4-二甲基苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-29:此表提供了41种具有式(Ia)的化合物B-29.01至B-29.41,其中R1是氢,R2是氢,R3是甲氧基,G是[2-(2,4-二甲基苯基)乙基氨基],并且R9取代基是如上表B中所定义的。
表B-30:此表提供了41种具有式(Ia)的化合物B-30.01至B-30.41,其中R1是氢,R2是氢,R3是甲氧基,G是[[2-(2,4-二甲基苯基)-2,2-二氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-31:此表提供了41种具有式(Ia)的化合物B-31.01至B-31.41,其中R1是氢,R2是甲基,R3是氢,G是[(2S)-2-(2,4-二氯苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-32:此表提供了41种具有式(Ia)的化合物B-32.01至B-32.41,其中R1是氢,R2是甲基,R3是氢,G是[(2S)-2-(2,4-二甲基苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-33:此表提供了41种具有式(Ia)的化合物B-33.01至B-33.41,其中R1是氢,R2是氯,R3是氢,G是[(2S)-2-(2,4-二甲基苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-34:此表提供了41种具有式(Ia)的化合物B-34.01至B-34.41,其中R1是氢,R2是氯,R3是氢,G是[(2S)-2-(2,4-二氯苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-35:此表提供了41种具有式(Ia)的化合物B-35.01至B-35.41,其中R1是氢,R2是氢,R3是甲基,G是[(2S)-2-(2,4-二氯苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-36:此表提供了41种具有式(Ia)的化合物B-36.01至B-36.41,其中R1是氢,R2是氢,R3是甲基,G是[(2S)-2-(2,4-二甲基苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-37:此表提供了41种具有式(Ia)的化合物B-37.01至B-37.41,其中R1是氢,R2是氢,R3是氟,G是[(2S)-2-(2,4-二氯苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-38:此表提供了41种具有式(Ia)的化合物B-38.01至B-38.41,其中R1是氢,R2是氢,R3是氟,G是[(2S)-2-(2,4-二甲基苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-39:此表提供了41种具有式(Ia)的化合物B-39.01至B-39.41,其中R1是氢,R2是氢,R3是甲氧基,,G是[(2S)-2-(2,4-二氯苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
表B-40:此表提供了41种具有式(Ia)的化合物B-40.01至B-40.41,其中R1是氢,R2是氢,R3是甲氧基,,G是[(2S)-2-(2,4-二甲基苯基)-2-氟-乙基]氨基],并且R9取代基是如上表B中所定义的。
优选地,具有式(I)的化合物不代表化合物A-01.61、A-01.62、A-02.61、A-02.62、A-03.61、A-03.62、A-05.23、A-05.61、A-05.62、A-06.23、A-06.61、A-06.62、A-07.23、A-07.59、A-07.61、A-07.62、A-08.62、A-27.61、A-27.62、B-08.06、B-09.06、B-11.02、B-11.06、B-11.11、B-11.12、B-11.15、B-11.23、B-11.24、B-11.25、B-11.38、B-11.40、或B-12.06。还优选地,具有式(I)的化合物不代表如表T1中所列出的化合物1.3、1.16、1.41、1.42、1.60、1.61、1.70、1.76或1.77。
实例
接下来的实例用来说明本发明。
本发明的化合物与已知化合物的区别可以在于在低施用率下更大的疗效,这可以由本领域的技术人员使用在实例中概述的实验程序,使用更低的施用率(如果必要的话)例如,50ppm、12.5ppm、6ppm、3ppm、1.5ppm、0.8ppm或0.2ppm来证实。
具有式(I)的化合物可以具有任何数量的益处,尤其包括针对保护植物免受由真菌引起的病害的有利水平的生物活性或对于用作农用化学品活性成分的优越特性(例如,更高的生物活性、有利的活性谱、增加的安全性(包括改善的作物耐受性)、改善的物理-化学特性、或增加的生物可降解性)。
贯穿本说明书,以摄氏度(℃)给出温度并且“mp”意指熔点。LC/MS意指液相色谱法质谱法,并且对装置和方法A的描述如下:
方法A:
在来自沃特斯公司(Waters)的质谱仪(SQD、SQDII单四极杆质谱仪)上记录光谱,该质谱仪装备有电喷射源(极性:正离子和负离子),毛细管电压:3.00kV,锥孔范围:30V,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650L/h,质量范围:100至900Da)和来自沃特斯公司的Acquity UPLC:二元泵、经加热的柱室、二极管阵列检测器和ELSD检测器。柱:Waters UPLC HSS T3,1.8μm,30x 2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5% MeOH+0.05% HCOOH,B=乙腈+0.05% HCOOH;梯度:10%-100% B,在1.2min内;流量(mL/min)0.85。
方法B:
在来自沃特斯公司的质谱仪(Acquity QDa质谱仪)上记录谱图,该质谱仪装备有电喷射源(极性:正和负极性转换,毛细管:0.8kV,锥孔范围:25V,源温度:120℃,去溶剂化温度:600℃,锥孔气体流量:50l/h,去溶剂化气体流量:1000L/h,质量范围:110至850Da和来自沃特斯公司的Acquity UPLC:四元溶剂管理器,加热柱室,二极管阵列检测器和ELSD检测器。柱:Waters UPLC HSS T3,1.8μm,30x 2.1mm,温度:40℃,PDA波长范围(nm):230至400,溶剂梯度:A=具有0.1%甲酸的水:乙腈:95:5v/v,B=具有0.05%甲酸的乙腈,梯度:0min-1.0min,10% B-90% A;1.0min-4.50min10%-100% B;4.51min-5.30min,100% B,0% A;5.31min-5.50min100%-10% B;5.51min-6.00min,10% B,90% A;流量(ml/min)0.6。
必要时,在对映异构体意义上纯的最终化合物可以在适当时从外消旋材料经由标准物理分离技术(例如反相手性色谱法)或通过立体选择性合成技术(例如通过使用手性起始材料)获得。
必要时,在对映异构体意义上纯的最终化合物可以在适当时从外消旋材料经由标准物理分离技术(例如反相手性色谱法)或通过立体选择性合成技术(例如通过使用手性起始材料)获得。
配制品实例
将该活性成分与辅助剂充分混合并且将混合物在合适的研磨机中充分研磨,从而提供可以用水稀释而给出所希望的浓度的悬浮液的可湿性粉剂。
将该活性成分与辅助剂充分混合并且将混合物在合适的研磨机中充分研磨,从而提供可以直接用于种子处理的粉剂。
可乳化浓缩物
在植物保护中可以使用的具有任何所要求的稀释的乳液可以通过用水稀释从这种浓缩物中获得。
通过将该活性成分与载体混合并且将混合物在合适的研磨机中研磨而获得即用型粉尘剂。这样的粉剂还可以用于种子的干拌种。
挤出的颗粒剂
将活性成分与辅助剂混合并研磨,并且将混合物用水润湿。将混合物挤出并且然后在空气流中干燥。
包衣的颗粒
活性成分[具有式(I)的化合物] 8%
聚乙二醇(分子量200) 3%
高岭土 89%
将精细研磨的活性成分在混合器中均匀地施用到用聚乙二醇湿润的高岭土上。以此方式获得无尘的包衣的颗粒。
悬浮液浓缩物
将精细研磨的活性成分与辅助剂紧密地混合,得到悬浮液浓缩物,从该悬浮液浓缩物可以通过用水稀释获得任何所希望的稀释度的悬浮液。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷雾、浇灌或浸渍进行保护。
种子处理用的可流动性浓缩物
将精细研磨的活性成分与辅助剂紧密地混合,得到悬浮液浓缩物,从该悬浮液浓缩物可以通过用水稀释获得任何所希望的稀释度的悬浮液。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷雾、浇灌或浸渍进行保护。
缓释的胶囊悬浮液
将28份的具有式(I)的化合物的组合与2份的芳香族溶剂以及7份的甲苯二异氰酸酯/多亚甲基-聚苯基异氰酸酯-混合物(8:1)混合。将此混合物在1.2份的聚乙烯醇、0.05份的消泡剂以及51.6份的水的混合物中进行乳化直至达到所希望的粒度。向此乳液中添加在5.3份的水中的2.8份的1,6-己二胺混合物。将混合物搅拌直至聚合反应完成。
将获得的胶囊悬浮液通过添加0.25份的增稠剂以及3份的分散剂进行稳定。该胶囊悬浮液配制品含有28%的活性成分。介质胶囊的直径是8-15微米。
将所得配制品作为适用于此目的装置中的水性悬浮液施用到种子上。
缩写清单:
aq. =水溶液
℃ =摄氏度
DCM =二氯甲烷
DMF =二甲基甲酰胺
DMSO =二甲基亚砜
DMSO-d6 =氘代二甲基亚砜
EtOAc =乙酸乙酯
equiv. =当量
h =小时
M =摩尔
min =分钟
mp =熔点
ppm =百万分率
RT =室温
Rt =保留时间
LC/MS =液相色谱法-质谱法(用于LC/MS分析的装置和方法的描述在上文给出)。
制备实例:
以下实例进一步说明了(但不限制)本发明。本领域技术人员将从这些程序中迅速地认识到有关反应物以及有关反应条件和技术的适当变体。
除非另外指出,否则1H NMR光谱是在400MHz(兆赫)下记录的并且化学位移以ppm记录。使用了以下缩写:s=单峰;br s=宽单峰;d=二重峰;dd=双二重峰;dt=双三重峰;t=三重峰,tt=三三重峰,q=四重峰,quin=五重峰,sept=七重峰;m=多重峰。
实例1:此实例说明了2-氯-N-[2-(2,4-二氯苯基)乙基]-5-(3-甲基苯氧基)吡啶-4-甲酰胺(表T1的化合物1.4)的制备。
a)5-溴-2-氯-N-[2-(2,4-二氯苯基)乙基]吡啶-4-甲酰胺的制备
将5-溴-2-氯吡啶-4-甲酸(0.52g,2.19mmol)、2-(2,4-二氯苯基)乙胺(0.5g,2.63mmol)、丙烷膦酸酐(T3P,在乙酸乙酯中50%,4.19g,6.59mmol)和三乙胺(0.48g,4.8mmol)在11mL的乙酸乙酯中的混合物在室温下搅拌2h。随后,将反应混合物用乙酸乙酯稀释并用饱和碳酸氢钠水溶液和盐水洗涤。将有机层经硫酸钠干燥并在减压下蒸发,将残余物通过色谱法在硅胶上使用环己烷/乙酸乙酯作为洗脱剂体系进行纯化,以产生5-溴-2-氯-N-[2-(2,4-二氯苯基)乙基]吡啶-4-甲酰胺(0.78g,1.91mmol)。
1H NMR(400MHz,CDCl3)δppm 3.12(t,2H),3.78(t,2H),6.09(bs,1H),7.25(d,1H),7.43-7.50(m,2H),8.58(s,1H),9.11(s,1H)。
b)2-氯-N-[2-(2,4-二氯苯基)乙基]-5-(3-甲基苯氧基)吡啶-4-甲酰胺的制备
将N-苄基-N'-(2-甲基-1-萘基)草酰胺(10mg,0.03mmol)、磷酸钾(0.13g,0.63mmol)和碘化铜(I)(3.1mg,0.02mmol)添加到5-溴-2-氯-N-[2-(2,4-二氯苯基)乙基]吡啶-4-甲酰胺(0.13g,0.32mmol)和间甲酚(42mg,0.38mmol)在1mL的二甲基亚砜的溶液中。将反应混合物在110℃下搅拌30min,然后冷却至室温,用水稀释并用乙酸乙酯萃取。将有机层用盐水洗涤,经硫酸钠干燥并在减压下浓缩。将残余物通过色谱法在硅胶上使用环己烷/乙酸乙酯作为洗脱剂体系进行纯化,以产生2-氯-N-[2-(2,4-二氯苯基)乙基]-5-(3-甲基苯氧基)吡啶-4-甲酰胺(94mg,0.21mmol)。
1H NMR(400MHz,CDCl3)δppm 2.41(s,3H),3.03(t,2H),3.78(t,2H),6.77-6.80(m,2H),6.95(d,1H),7.07-7.16(m,2H),7.32(t,1H),7.61(bs,1H),7.98(s,1H),8.10(s,1H)。
实例2:此实例说明了N-[2-(2,4-二氯苯基)-2-氟-乙基]-2-甲基-5-(3-甲基苯氧基)吡啶-4-甲酰胺(表T1的化合物1.1)的制备。
a)2-甲基-5-(3-甲基苯氧基)吡啶-4-甲酸的制备
将N-苄基-N'-(2-甲基-1-萘基)草酰胺(37mg,0.11mmol)、磷酸钾(0.50g,2.37mmol)和碘化铜(I)(11mg,0.06mmol)添加到5-氯-2-甲基吡啶-4-甲酸乙酯(0.22g,1.18mmol)和间甲酚(0.13g,1.18mmol)在3mL的二甲基亚砜的溶液中。将反应混合物在110℃下搅拌1h,然后冷却至室温,用水稀释并用乙酸乙酯萃取。将有机层用盐水洗涤,经硫酸钠干燥并在减压下浓缩。将残余物通过色谱法在硅胶上使用环己烷/乙酸乙酯作为洗脱剂体系进行纯化,以产生2-甲基-5-(3-甲基苯氧基)吡啶-4-甲酸(75mg,0.31mmol)。
1H NMR(400MHz,DMSO-d6)δppm 2.50-2.54(m,6H),6.53-6.61(m,2H),7.01-7.07(m,2H),7.78(s,1H),8.02(s,1H)。
b)N-[2-(2,4-二氯苯基)-2-氟-乙基]-2-甲基-5-(3-甲基苯氧基)吡啶-4-甲酰胺
的制备
将2-甲基-5-(3-甲基苯氧基)吡啶-4-甲酸(25mg,0.1mmol)、2-(2,4-二氯苯基)-2-氟乙胺盐酸盐(30mg,0.12mmol)、丙烷膦酸酐(T3P,在乙酸乙酯中50%,0.19g,0.31mmol)和三乙胺(24mg,0.24mmol)在1mL的乙酸乙酯中的混合物在室温下搅拌2h。随后,将反应混合物用乙酸乙酯稀释并用饱和碳酸氢钠水溶液和盐水洗涤。将有机层经硫酸钠干燥并在减压下蒸发,将残余物通过色谱法在硅胶上使用环己烷/乙酸乙酯作为洗脱剂体系进行纯化,以产生N-[2-(2,4-二氯苯基)-2-氟-乙基]-2-甲基-5-(3-甲基苯氧基)吡啶-4-甲酰胺(23mg,0.05mmol)。
1H NMR(400MHz,CDCl3)δppm 2.40(s,3H),2.61(s,3H),3.75-3.88(m,1H),4.09-4.18(m,2H),6.82-6.85(m,2H),7.06-7.13(m,2H),7.31-7.38(m,2H),7.89(s,1H),7.95(bs,1H),8.18(s,1H)。
表T1:根据式(I)的化合物的LCMS数据和/或保留时间(Rt):
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生物学实例/测试方法:
茄链格孢菌(Alternaria solani)(番茄早枯病)
将番茄叶圆片置于多孔板(24孔规格)中的水琼脂上并用测试溶液进行喷雾。干燥之后,将叶圆片用真菌的孢子悬浮液接种。适当的孵育之后,化合物的活性4dpi(孵育之后的天数)被评定为预防性杀真菌活性。
当与在相同条件下显示出广泛的病害发展的未处理的对照相比时,来自表T1的以下化合物在200ppm下对茄链格孢给出至少80%的控制:
1.1、1.7、1.14、1.20、1.39、1.41、1.87、1.94、1.95、1.98。
富克葡萄孢盘菌(Botryotinia fuckeliana)又名灰葡萄孢菌(灰霉病)
将来自冷冻储存的真菌分生孢子直接混入营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的DMSO溶液置于微量滴定板(96孔规格)中并且向其中添加含有真菌孢子的营养肉汤。将这些测试板在24℃下温育并且在72小时之后光度测定地确定对生长的抑制。
当与在相同条件下显示出广泛的病害发展的未处理的对照相比时,来自表T1的以下化合物在20ppm下对富克葡萄孢盘菌给出至少80%的控制:
1.1、1.2、1.3、1.4、1.5、1.6、1.7、1.8、1.9、1.10、1.13、1.14、1.15、1.16、1.17、1.20、1.21、1.22、1.24、1.32、1.35、1.38、1.39、1.41、1.42、1.43、1.45、1.47、1.53、1.54、1.55、1.57、1.58、1.59、1.60、1.61、1.62、1.66、1.67、1.68、1.70、1.71、1.75、1.76、1.77、1.78、1.79、1.80、1.81、1.82、1.84、1.85、1.86、1.87、1.88、1.89、1.90、1.92、1.91、1.93、1.94、1.95、1.96、1.98。
富克葡萄孢盘菌又名灰葡萄孢菌(番茄上的灰霉病)
在喷雾室中,用在水中稀释的配制的测试化合物喷雾处理4周龄的番茄植物栽培品种Roter Gnom。在施用后两天,通过用孢子悬浮液对其进行喷雾来接种测试植物。将接种的测试植物在温室中在20℃和95%rh下进行温育,并且在未处理的比较植物上出现适当水平的病害时(施用后5-6天),评估被病害覆盖的叶面积百分比。
当与在相同条件下显示出广泛的病害发展的未处理的对照相比时,来自表T1的以下化合物在200ppm下对富克葡萄孢盘菌给出至少50%的控制:
1.1、1.3、1.4、1.5、1.6、1.7、1.8、1.9、1.10、1.11、1.13、1.14、1.15、1.16、1.20、1.21、1.22、1.35、1.38、1.39、1.41、1.43、1.91、1.60、1.61、1.70、1.58、1.70、1.79、1.80、1.81、1.82、1.84、1.85、1.87、1.88、1.91。
瓜小丛壳菌(Glomerella lagenarium)又名瓜类炭疽菌(Colletotrichum
lagenarium)(炭疽病)
将来自冷冻储存的真菌分生孢子直接混入营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的DMSO溶液置于微量滴定板(96孔规格)中并且向其中添加含有真菌孢子的营养肉汤。将这些测试板在24℃下孵育并且72小时之后在620nm下通过光度法确定对生长的抑制。
当与在相同条件下显示出广泛的病害发展的未处理的对照相比时,来自表T1的以下化合物在20ppm下对瓜小丛壳菌给出至少80%的控制:
1.1、1.2、1.3、1.5、1.6、1.7、1.8、1.9、1.10、1.11、1.12、1.13、1.14、1.15、1.16、1.17、1.19、1.20、1.21、1.22、1.23、1.24、1.26、1.29、1.31、1.32、1.33、1.34、1.35、1.39、1.41、1.42、1.43、1.46、1.47、1.53、1.57、1.58、1.60、1.61、1.63、1.65、1.66、1.68、1.71、1.74、1.75、1.76、1.77、1.78、1.79、1.80、1.81、1.82、1.84、1.85、1.86、1.87、1.88、1.89、1.90、1,91、1.92、1.93、1.94、1.95、1.96、1.97、1.98。
黄色镰刀菌(根腐病)
将来自冷冻储存的真菌分生孢子直接混入营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的DMSO溶液置于微量滴定板(96孔规格)中并且向其中添加含有真菌孢子的营养肉汤。将这些测试板在24℃下温育并且在72小时之后光度测定地确定对生长的抑制。
当与在相同条件下显示出广泛的病害发展的未处理的对照相比时,来自表T1的以下化合物在20ppm下对黄色镰刀菌给出至少80%的控制:
1.1、1.41、1.67、1.94。
颖枯壳针孢(Phaeosphaeria nodorum,又名Septoria nodorum)(小麦颖斑枯病)
将小麦叶段置于多孔板(24孔规格)中的琼脂上并且用测试溶液进行喷雾。干燥之后,将叶圆片用真菌的孢子悬浮液接种。在适当的温育之后,化合物的活性4dpi(孵育之后的天数)被评定为预防性杀真菌活性。
当与在相同条件下显示出广泛的病害发展的未处理的对照相比时,来自表T1的以下化合物在200ppm下对颖枯壳针孢给出至少80%的控制:
1.1、1.3、1.7、1.14、1.39、1.41、1.86、1.87、1.92、1.94、1.95。
雪腐明梭孢(Monographella nivalis),又名雪霉叶枯菌(Microdochium
nivale),雪腐镰刀菌(Fusarium nivale)(雪霉病,根腐病):
将来自冷冻储存的真菌分生孢子直接混入营养肉汤(PDB马铃薯右旋糖肉汤)中。将测试化合物的DMSO溶液置于微量滴定板(96孔规格)中并且向其中添加含有真菌孢子的营养肉汤。将这些测试板在24℃下孵育并且72小时之后在620nm下通过光度法确定对生长的抑制。
当与在相同条件下显示出广泛的病害发展的未处理的对照相比时,来自表T1的以下化合物在20ppm下对雪腐明梭孢给出至少80%的控制:
1.1、1.13、1.14、1.28、1.36、1.39、1.41、1.44、1.46、1.49、1.50、1.60、1.63、1.70、1.78、1.79、1.81、1.84、1.85、1.86、1.87、1.88、1.92、1.94、1.95、1.96。
圆核腔菌(Pyrenophora teres)(大麦网斑病(Net blotch of barley))
将大麦叶节置于多孔板(24孔板)的琼脂中并且喷洒试验溶液。干燥之后,将叶圆片用真菌的孢子悬浮液接种。适当的温育之后,化合物的活性4dpi(温育之后的天数)被评定为预防性杀真菌活性。
当与在相同条件下显示出广泛的病害发展的未处理的对照相比时,来自表T1的以下化合物在200ppm下对圆核腔菌给出至少80%的控制:
1.1、1.3、1.14、1.39、1.41、1.85、1.87、1.88、1.94。
核盘菌(Sclerotinia sclerotiorum)(棉状腐病(Cottony rot),白霉病(white
mold))
将从新鲜液体培养物制备的真菌的菌丝体片段直接混入营养肉汤(PDB马铃薯葡萄糖肉汤)中。将测试化合物的DMSO溶液置于微量滴定板(96孔规格)中并且向其中添加含有真菌孢子的营养肉汤。将这些测试板在24℃下孵育并且72小时之后在620nm下通过光度法确定对生长的抑制。
当与在相同条件下显示出广泛的病害发展的未处理的对照相比时,来自表T1的以下化合物在20ppm下对核盘菌给出至少80%的控制:
1.1、1.2、1.3、1.5、1.7、1.8、1.13、1.14、1.20、1.39、1.41、1.70、1.79、1.81、1.85、1.87、1.88、1.92、1.94、1.95、1.96。
Claims (15)
1.一种具有式(I)的化合物:
其中:
L1是-O-或-CH2-或键;
R1选自氢、卤素、氰基、C1-C3-烷基或C1-C3-烷氧基;
R2选自氢、氰基、烷基硫基、卤素、C1-C3-烷基、C2-C4-烯基、C2-C3-炔基、C1-C3-烷氧基、C1-C3-氟烷基、C1-C3-氟烷氧基、C3-C4-环烷基或C1-C3-烷基磺酰基;
R3选自氢、卤素、氰基、甲基、C1-C4-烷基、C1-C3-氟烷基、C2-C4-烯基、C2-C4-炔基、C1-C4-烷氧基、C2-C4-烯氧基、C2-C5-炔氧基、C1-C3-氟烷氧基、C3-C4-环烷基;或者
R3是任选地被1或2个取代基取代的苯氧基,所述取代基独立地选自卤素、氰基、甲基、乙基、二氟甲基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、环丙基,
R4和R5独立地选自氢、氰基或甲基;或者
R4和R5与它们所附接的碳原子一起形成环丙基或环丁基;
R6和R7独立地选自氢、氟、氯、甲基、三氟甲基、羟基、甲氧基、甲氧基甲基、二氟甲氧基、烷基硫基、甲基硫烷基;或者
R6和R7与它们所附接的碳原子一起形成氧代基、环丙基或环丁基、或4元至6元单环杂环基团,所述单环杂环基团包含单独选自N、O和S的1或2个杂原子;或者
R4和R6与它们所附接的碳原子一起形成C3-C4-环烷基或4元至6元单环杂环基团,所述单环杂环基团包含单独选自N、O和S的1或2个杂原子,并且R5和R7独立地是氢或卤素;
R8是任选地被以下取代的苯基:
单个取代基,其选自C1-C4-烷基、C1-C2-卤代烷基、C1-C3-烷氧基、C1-C3-烷基硫烷基、C1-C3-烷基磺酰基、C1-C2-卤代烷氧基、C2-C3-烯基、C2-C3-卤代烯基、C2-C3-炔基、C3-C4-环烷基、C3-C4-环烷氧基或-NH(COC1-C3-烷基),或者
可以相同或不同的1、2或3个取代基,所述取代基独立地选自羟基、卤素、巯基、氨基、氰基、甲基、乙基、丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、甲基硫烷基、甲基磺酰基、二氟甲氧基、三氟甲氧基、环丙基、环丁基、环丙氧基、-NH(COCH3);并且
R9是任选地被以下取代的苯基:
单个取代基,其选自C1-C4-烷基、C1-C2-卤代烷基、C1-C4-烷氧基、C1-C3-烷基硫烷基、C1-C3-烷基磺酰基、C1-C2-卤代烷氧基、C2-C3-烯基、C2-C3-卤代烯基、C2-C3-炔基、C3-C4-环烷基、C3-C4-环烷氧基;或者
可以相同或不同的1、2或3个取代基,所述取代基独立地选自羟基、卤素、巯基、氨基、氰基、甲基、乙基、丙基、异丙基、二氟甲基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、丙炔氧基、甲基硫烷基、甲基磺酰基、二氟甲氧基、三氟甲氧基、环丙基、环丁基、环丙氧基、-NH(COCH3);或者
或其盐或N-氧化物。
2.根据权利要求1所述的化合物,其中,L1是键。
3.根据权利要求1或权利要求2所述的化合物,其中,R1是氢、氯、甲基或甲氧基,并且优选氢。
4.根据权利要求1至3中任一项所述的化合物,其中,R2是氢、氰基、烷基硫基、卤素、甲基、甲氧基、三氟甲基、环丙基或甲基磺酰基。
5.根据权利要求1至4中任一项所述的化合物,其中,R2是氢、氯或甲基。
6.根据权利要求1至5中任一项所述的化合物,其中,R3是氢、甲基、氟、氯、溴或氰基、甲氧基。
7.根据权利要求1至6中任一项所述的化合物,其中,R4和R5是氢。
8.根据权利要求1至7中任一项所述的化合物,其中,R6是氢或氟,并且R7是氢或氟。
9.根据权利要求1至8中任一项所述的化合物,其中,R8是任选地被1或2个取代基取代的苯基,所述取代基独立地选自羟基、卤素、氰基、甲基、乙基、二氟甲基、三氟甲基、甲氧基或乙氧基。
10.根据权利要求1至9中任一项所述的化合物,其中,R9是任选地被1或2个取代基取代的苯基,所述取代基独立地选自卤素、氰基、甲基、乙基、二氟甲基、三氟甲基、甲氧基、乙氧基、丙氧基、异丙氧基、叔丁氧基、丙炔氧基、甲基硫烷基、二氟甲氧基、三氟甲氧基、环丙基和-NH(COCH3)。
11.根据权利要求1至10中任一项所述的化合物,其中,R9是任选地被单个取代基取代的苯基,所述取代基选自乙基、甲基、三氟甲基、环丙基或氰基。
12.一种农用化学组合物,其包含杀真菌有效量的根据权利要求1至11中任一项所述的化合物。
13.根据权利要求12所述的组合物,其进一步包含至少一种另外的活性成分和/或农用化学上可接受的稀释剂或载体。
14.一种控制或预防有用植物被植物病原性微生物侵染的方法,其中将杀真菌有效量的根据权利要求1至11中任一项所述的化合物、或包含此化合物作为活性成分的组合物施用于所述植物、其部分或其场所。
15.根据权利要求1至11中任一项所述的化合物作为杀真菌剂的用途。
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