CN117177963A - 杀微生物的喹啉/喹喔啉异喹啉衍生物 - Google Patents
杀微生物的喹啉/喹喔啉异喹啉衍生物 Download PDFInfo
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- CN117177963A CN117177963A CN202280029780.5A CN202280029780A CN117177963A CN 117177963 A CN117177963 A CN 117177963A CN 202280029780 A CN202280029780 A CN 202280029780A CN 117177963 A CN117177963 A CN 117177963A
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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中所定义的,所述化合物可用作杀有害生物剂、尤其可用作杀真菌剂。
Description
本发明涉及杀微生物的喹啉/喹喔啉异喹啉衍生物,例如作为活性成分,其具有杀微生物活性、特别是杀真菌活性。本发明还涉及这些喹啉/喹喔啉异喹啉衍生物的制备,涉及在这些喹啉/喹喔啉异喹啉衍生物的制备中有用的中间体,涉及这些中间体的制备,涉及包含这些喹啉/喹喔啉异喹啉衍生物中的至少一种的农用化学组合物,涉及这些组合物的制备并且涉及这些喹啉/喹喔啉异喹啉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、特别是真菌侵染的用途。
小麦是为其种子而耕种的草,为世界范围内主粮的谷物谷粒。小麦的许多物种一起构成了小麦属植物;最广泛种植的是普通小麦(T.aestivum)。然而,小麦的耕种存在许多挑战。小麦叶枯病(Septoria tritici blotch)是由子囊菌真菌禾生球腔菌(无性阶段:小麦壳针孢)引起的,并且是小麦最重要的病害之一——其是此作物最具经济破坏性的病害之一(是目前欧洲最经济上相关的病害)。因此,特别地,不断需要开发新的方法来控制或预防真菌植物病原体对谷物作物的侵染,例如禾生球腔菌对谷物、特别是小麦的侵染。
某些杀真菌喹啉和喹喔啉化合物分别描述于WO 2007/011022和WO 2017/090664中。
根据本发明,提供了一种具有式(I)的化合物:
其中,
A是N或CR8;
R1是氟、氰基、氯或甲基;
R2是氢或氟;
R3是C1-C4烷基或C3-C5环烷基;
R4是C1-C4烷基或C3-C5环烷基;
R5是卤素、C1-C4烷基、C2-C4烯基、C2-C4炔基、C1-C4烷氧基、羟基、C1-C4卤代烷基、C1-C4卤代烷氧基、C2-C4卤代烯基、氰基、硝基、-N(R9c)2、氰基C1-C3烷基、C3-C5环烷基、-CR9a(=NOR9b);
R6是氢、羟基、卤素、C1-C4烷基、C1-C4卤代烷基、氰基;
R7是氢或甲基;
R8是氢或甲基;
R9a是氢、C1-C4烷基或C3-C5环烷基;R9b是C1-C4烷基或C3-C5环烷基;并且R9c独立地选自氢或C1-C4烷基,或与它们所连接的氮原子一起形成4-、5-或6-元饱和杂环;
或其盐、对映异构体、互变异构体和/或N-氧化物。
出人意料地,已经发现,为实际目的,具有式(I)的新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、或包含这种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。
在取代基被指示为任选地被取代的情况下,这意指它们可以带有或可以不带有一个或多个相同或不同的取代基,例如一至四个取代基。通常地,同时存在不超过三个这样的任选的取代基。优选地,同时存在不超过两个这样的任选的取代基(即,该基团可以任选地被指示为“任选的”的取代基中的一个或两个取代)。在“任选的取代基”基团是较大的基团(如环烷基或苯基)时,最优选的是仅存在一个这样的任选的取代基。在基团被指示为被例如烷基取代时,这包括是其他基团的一部分的那些基团,例如烷硫基中的烷基。
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“羟基(hydroxyl)”或“羟基(hydroxy)”意指-OH基团。
如本文使用的,氰基意指-CN基团。
如本文使用的,硝基意指-NO2基团。
如本文使用的,术语“C1-C4烷基”是指仅由碳原子和氢原子组成的直链的或支链的烃链基团,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-C3烷基应相应地解释。C1-C4烷基的实例包括但不限于甲基、乙基、正丙基、1-甲基乙基(异丙基)、正丁基和1,1-二甲基乙基(叔丁基)。
如本文使用的,术语“C1-C4卤代烷基”是指被一个或多个相同或不同的卤素原子取代的如上一般定义的C1-C4烷基基团。C1-C4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“C2-C4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、具有从二至四个碳原子、通过单键附接至分子的其余部分。C2-C4烯基的实例包括但不限于乙烯基(次乙基)、丙-1-烯基、烯丙基(丙-2-烯基)和丁-1-烯基。
如本文使用的,术语“C2-C4卤代烯基”是指如上一般定义的C2-C4烯基基团,其被一个或多个相同或不同的卤素原子取代。
如本文使用的,术语“C2-C4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,具有从二至四个碳原子,并且通过单键附接至分子的其余部分。C2-C4炔基的实例包括但不限于乙炔基、丙-1-炔基、炔丙基(丙-2-炔基)和丁-1-炔基。
如本文使用的,术语“C3-C5环烷基”是指稳定的单环基团,其是饱和的并且含有3至5个碳原子。C3-C5环烷基的实例包括但不限于环丙基、环丁基和环戊基。
如本文使用的,术语“C1-C4烷氧基”是指具有式RaO-的基团,其中Ra是如上一般定义的C1-C4烷基基团。C1-C4烷氧基的实例包括但不限于甲氧基、乙氧基、丙氧基、异丙氧基。
如本文使用的,术语“C1-C4卤代烷氧基”是指被一个或多个相同或不同的卤素原子取代的如上定义的C1-C4烷氧基。C1-C4卤代烷氧基的实例包括但不限于氟甲氧基、二氟甲氧基、氟乙氧基、三氟甲氧基和三氟乙氧基。
如本文使用的,术语“氰基C1-3烷基”是指被一个或多个氰基基团取代的如上一般定义的C1-3烷基基团。氰基C1-3烷基的实例包括但不限于氰基甲基。
在具有式(I)的化合物中存在一个或多个可能的不对称碳原子意指化合物能以光学异构体形式(即对映异构体或非对映异构体的形式)存在。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体形式及其混合物。同样地,式(I)旨在包括所有可能的互变异构体。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)的化合物是呈游离形式、氧化形式(作为N-氧化物或S-氧化物)、共价水合形式、或盐形式(例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根据本发明的具有式(I)的化合物的取代基R1、R2、R3、R4、R5、R6、R7、A、R8、R9a、R9b和R9c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。
R1是氟、氯、氰基或甲基。优选地,R1是氟。
R2是氢或氟。在本发明的一些实施例中,R2是氢。在本发明的一些实施例中,R2是氟。
优选地,当R1是氟时,R2是氢或氟。
R3是C1-C4烷基或C3-C5环烷基。优选地,R3是C1-C4烷基。更优选地,R3是甲基、乙基或正丙基。最优选地,R3是甲基。
R4是C1-C4烷基或C3-C5环烷基。优选地,R4是C1-C4烷基。最优选地,R4是甲基。
R5是卤素、C1-C4烷基、C2-C4烯基、C2-C4炔基、C1-C4烷氧基、羟基、C1-C4卤代烷基、C1-C4卤代烷氧基、C2-C4卤代烯基、氰基、硝基、-N(R9c)2、氰基C1-C3烷基、C3-C5环烷基、CR9a(=NOR9b)。优选地,R5是卤素、氰基、甲基、乙基、甲氧基、乙氧基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、氰基甲基或环丙基。更优选地,R5是卤素或氰基。最优选地,R5是氯、溴或氰基。
R6是氢、羟基、卤素、C1-C4烷基、C1-C4卤代烷基或氰基。优选地,R6是氢、卤素或C1-C4烷基。更优选地,R6是氢、氯或甲基。最优选地,R6是氢或甲基。
R7是氢或甲基。优选地,R7是氢。
A是N或CR8。在本发明的一些实施例中,A是N。在本发明的其他实施例中,A是CR8,其中R8是氢或甲基,并且优选地,氢。
R9a是氢、C1-C4烷基或C3-C5环烷基;并且优选地氢或甲基。
R9b是C1-C4烷基或C3-C5环烷基;并且优选地甲基或乙基。
R9c独立地选自氢或C1-C4烷基,或与它们所连接的氮原子一起形成4-、5-或6-元饱和杂环基团,如氮杂环丁烷基、吡咯烷基或哌啶基。优选地,R9c是氢或甲基。
在本发明的优选实施例中,R1和R2是氟,或R1是氟并且R2是氢。在本发明的优选实施例中,R3和R4是甲基。
在本发明的某些实施例中,具有式(I)的化合物可以选自以下之一:
在本发明的某些实施例中,具有式(I)的化合物可以是对映异构体的外消旋混合物。另外,具有式(I)的化合物可以是如下的单独的对映异构体。
优选地,在具有式(I)的化合物中,R3和R4取代基具有如下的cis关系。
优选地,具有式(I)的化合物是选自表E(下文)中的E.01至E.15之一的化合物。
根据本发明,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根据本发明的化合物或包含这种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。优选地,植物病原性微生物是(i)禾生球腔菌,(ii)雪腐明梭孢(雪霉叶枯菌)或(iii)玉米赤霉菌(无性型:禾谷镰刀菌)。优选地,有用植物是谷物、特别是小麦。
在下表A1至A7中示出了具有式(I)的化合物的具体实例:
表A1提供了87种根据本发明的化合物,其各自具有式(IA)或式(IB):
其中R1是-F、R2和R7是-H并且A是-CH,并且其中R3、R4、R5和R6的值是如下表Z中定义的:
表Z
表A2提供了87种化合物,其各自具有式(IA)和式(IB),其中R1是-F、R2是F、R7是-H并且A是-CH,并且其中R3、R4、R5和R6的值是如上表Z中定义的。
表A3提供了87种化合物,其各自具有式(IA)和式(IB),其中R1是-F、R2是H、R7是-CH3并且A是-CH,并且其中R3、R4、R5和R6的值是如上表Z中定义的。
表A4提供了87种化合物,其各自具有式(IA)和式(IB),其中R1是-F、R2是H、R7是-H并且A是-N,并且其中R3、R4、R5和R6的值是如上表Z中定义的。
表A5提供了87种化合物,其各自具有式(IA)和式(IB),其中R1是-F、R2是-F、R7是-H并且A是-N,并且其中R3、R4、R5和R6的值是如上表Z中定义的。
表A6提供了87种化合物,其各自具有式(IA)和式(IB),其中R1是-F、R2是H、R7是-CH3并且A是-N,并且其中R3、R4、R5和R6的值是如上表Z中定义的。
表A7提供了87种化合物,其各自具有式(IA)和式(IB),其中R1是-F、R2是-F、R7是-CH3并且A是-N,并且其中R3、R4、R5和R6的值是如上表Z中定义的。
本发明的化合物可以如在以下方案中所示来制备,其中(除非另外说明)每一变量的定义是如以上针对具有式(I)的化合物所定义的。
如方案1中所示,具有通式(I)的化合物可以在脱水剂或布朗斯台德酸如硫酸或三氟甲烷磺酸酐的存在下,在惰性溶剂的存在或不存在下在从-70℃至+150℃的温度下,由具有式(III)的腈和具有式(II)的醇制备。
方案1.
具有式(III)的腈可以在过渡金属催化剂(如通过合适的支持配体稳定的Cu-或Pd-盐)和氰化物源(如KCN、Zn(CN)2或亚铁氰化钾)的存在下,在惰性溶剂如N,N-二甲基乙酰胺中,在20℃与150℃之间的温度下,由具有式(III-a)的化合物制备,其中R21是氯、溴、碘或三氟甲磺酰氧基。代表性条件描述于Org.Process Res.Dev.[有机加工研究与开发]2014,p.693-698中。可替代地,具有式(III)的腈可以通过本领域技术人员熟知的方法从具有式(IV-b)的羧酸通过官能团相互转化制备。这在方案2中示出。
方案2.
通过还原加成法由可商购试剂制备醇(II)是本领域技术人员熟知的。
可替代地,具有通式(I)的化合物可以在脱水剂如三氟甲磺酸酐或氯亚甲基(二甲基)氯化铵和碱如2,6-二甲基吡啶的存在下在惰性溶剂如二氯甲烷或氯苯中在-40℃至150℃之间的温度下由具有式(IV)的酰胺制备。这在方案3中示出。
方案3.
具有式(IV)的化合物可以在脱水剂如丙基膦酸酐或光气和碱如三乙胺的存在下在惰性溶剂如甲苯中由具有式(IV-b)的羧酸和具有式(IV-a)的胺制备。可替代地,具有式(IV)的化合物可以在过渡金属盐如乙酸钯(II)、膦配体(如1,1'-双(二苯基膦基)-二茂铁)和碱(如三乙胺)的存在下在溶剂如甲苯中在一氧化碳气氛下由具有式(III-a)(其中R21是氯、溴、碘或三氟甲磺酰氧基)和(IV-a)的化合物制备。这示于方案4中。
方案4.
具有式(IV-a)的胺可以通过许多独立的方法制备,其中代表性但非详尽的选择如下所述:
I.具有式(IV-a)的胺可以通过在氢气气氛下用合适的过渡金属催化剂如Pd黑处理还原具有式(V-a)的硝基化合物来制备。具有式(V-a)的硝基化合物可以在胺催化剂如乙酸铵的存在下由具有式(V-b)的硝基烷烃和具有式(V-c)的羰基化合物制备。这在方案5中示出。
方案5.
II.具有式(IV-a)的胺可以通过以下方式制备:在金属镁的存在下,将具有式(V-d)的苄基卤(其中X是氯、溴或碘)加成到具有式(V-e)的亚胺(其中R22是-S(O)C1-C4烷基、-S(O)1,3,5-三(丙-2-基)苯或对甲氧基苯,然后通过用布朗斯台德酸如盐酸处理来裂解R22-基团。这在方案6中示出。
方案6.
III.具有式(IV-a)的胺可以通过以下方式制备:在碱如二异丙基氨基锂的存在下,由具有式(V-f)的亚胺和具有式(V-d)的苄基卤(其中X是氯、溴或碘)制备,然后通过用水性酸或羟胺处理来水解亚胺基团。这在方案7中示出。
方案7.
IV.具有式(IV-a)的胺可以通过以下方式制备:在铜盐如CuI的存在下由具有式(V-g)的环氧化物和具有式(V-h)的格氏试剂(其中X是氯、溴或碘)制备,然后是所得羟基的熟知官能团相互转化。这在方案8中示出。
方案8.
具有式(V-b)、(V-c)、(V-d)、(V-e)、(V-f)、(V-g)和(V-h)的化合物的制备遵循本领域技术人员熟知的充分描述的文献优先级。
可替代地,具有式(I)的化合物可以通过以下方式制备:在脱水剂如MgSO4和任选的路易斯或布朗斯台德酸催化剂的存在下由具有式(IV-c)的醛和具有式(IV-a)的胺制备,然后用氧化剂如MnO2或NaOCl氧化具有式(V-e)的中间体胺。这在方案9中示出。
方案9.
可替代地,具有通式(I)的化合物可以在过渡金属盐(如乙酸钯(II)或NiCl2)、膦配体(如1,1'-双(二叔丁基膦基)二茂铁)和碱如K3PO4的存在下,在溶剂如THF或N,N-二甲基甲酰胺中,在-20℃与150℃之间的温度下由具有式(VI-a)的化合物(其中R23是-B(OH)2、-B(OC(CH3)2C(CH3)2O)、-Sn(C1-C4烷基)3、-SO2Na、-MgBr、-ZnBr或-Zn(新戊酸盐))和具有式(VI-b)的化合物(其中R24是氯、溴、碘、或-OSO2CF3)制备。具有式(VI-a)的化合物(其中R23是-B(OH)2、-B(OC(CH3)2C(CH3)2O)、-Sn(C1-C4烷基)3、-SO2Na、-MgBr、-ZnBr或-Zn(新戊酸盐))可以根据本领域技术人员熟知的并且在RSC Adv.[英国皇家化学会进展],2013,p.12518-12539中描述的文献报道的方法由具有式(III-a)的化合物(其中R21是氯、溴、碘或三氟甲磺酰氧基)制备。这在方案10中示出。
方案10.
可替代地,具有通式(I)的化合物可以在过渡金属盐(如乙酸钯(II)或NiCl2)、膦配体(如1,1'-双(二叔丁基膦基)二茂铁)、另外的催化添加剂如CuI和碱如K3PO4的存在下,在溶剂如THF或N,N-二甲基甲酰胺中,在-20℃与150℃之间的温度下由具有式(III-a)的化合物(其中R21是氯、溴、碘或-OSO2CF3)和具有式(VI-c)的化合物(其中R25是-B(OH)2、-Sn(C1-C4烷基)3、-CO2H或-SO2Na)制备。这在方案11中示出。
方案11.
具有式(VI-b)的化合物(其中R24是氯、溴、碘或-OSO2CF3)可以通过在惰性溶剂(如甲苯或DCM)中用适当的脱水剂如氯亚甲基(二甲基)氯化铵或三氟甲磺酸酐处理由具有式(VI-d)的化合物制备。具有式(VI-d)的化合物可以在乙酸钯(II)和苯醌的存在下由具有式(IV-a)的化合物获得,如Organometallics[有机金属]2013,p.649-659中所述。可替代地,具有式(VI-d)的化合物可在适当负载的过渡金属催化剂存在下通过催化氢化由具有式(VI-e)化合物获得。可替代地,具有式(VI-d)的化合物可以通过用甲醛或其等价物和路易斯酸或布朗斯台德酸处理由具有式(IV-a)的化合物制备以形成具有式(VI-f)的四氢异喹啉。然后可以在氧化剂如亚氯酸钠或次氯酸钠的存在下将具有式(VI-f)的化合物氧化成具有式(VI-d)的化合物。这在方案12中示出。
方案12
可替代地,具有式(I)的化合物可以通过使用本领域技术人员已知的标准合成技术转化另一种密切相关的具有式(I)的化合物来获得。非详尽的实例包括氧化反应、异构化反应、还原反应、氢化反应、水解反应、偶联反应、芳香族亲核或亲电取代反应、亲核取代反应、烷基化反应、亲核加成反应以及卤化反应。
以上方案中所述的某些中间体是新的并且如此形成本发明的另一个方面。
具有式(I)的这些化合物可以例如作为活性成分用于农业部门和相关领域,来控制植物有害生物或用于非生命材料上来控制腐败微生物或潜在地对人类有害的生物。这些新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。它们具有非常有用的治疗、预防和系统特性,并且可以用于保护许多栽培植物。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,而同时还保护例如稍后生长的那些植物部分免于植物病原性微生物的侵害。
还可以使用具有式(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”意指能够对真菌生长产生影响的这样一种化合物或这样的化合物的组合的量。控制或改变的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植物上形成屏障或其他防御以预防真菌侵染。
也可以将具有式(I)的化合物用作处理植物繁殖材料,例如种子(如果实、块茎、或谷粒),或植物插条(例如稻)的拌种剂,用于保护免受真菌侵染连同对抗在土壤中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对它们进行包衣,将具有式(I)的化合物施用至谷粒(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,根据本发明的化合物可以用于控制相关领域的真菌,例如在工业材料(包括木材以及与木材有关的工业产品)的保护中、在食品储存中、在卫生管理中。
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)免受真菌侵袭。
具有式(I)的化合物和含有它们的杀真菌组合物可以用于控制由广谱的真菌植物病原体引起的植物病害。它们有效地控制广谱的植物病害,如观赏植物、草皮、蔬菜、大田、谷物、以及水果作物的叶病原体。
可以被控制的病害的这些真菌和真菌载体连同植物病原性细菌和病毒是例如:
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))、假丝酵母属物种(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、间座壳属物种(Diaporthe spp)、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、朗氏镰刀菌(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(Gaeumannomyces graminis)、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(Leveillula taurica)、松针散盘壳(Lophodermium seditiosum)、雪霉叶枯菌(Microdochium nivale)、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(Phellinus igniarus)、瓶霉蚁属物种、茎点霉属物种、葡萄生拟茎点菌(Phomopsisviticola)、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、柄锈菌属物种(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))、孢子丝菌属物种(Sporothorix)、颖枯壳多孢(Stagonospora nodorum)、匍柄霉属物种(Stemphylium spp)、毛韧革菌(Stereum hirsutum)、水稻枯纹病菌(Thanatephorus cucumeris)、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、条黑粉菌属物种(Urocystis spp)、黑粉菌属物种(Ustilago spp)、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。
具体地,具有式(I)的化合物和含有它们的杀真菌组合物可以用于控制由担子菌纲、子嚢菌纲、卵菌纲和/或半知菌纲、Blasocladiomycete、壶菌纲、球囊菌纲(Glomeromycete)和/或毛霉菌纲(Mucoromycete)中的广谱的真菌植物病原体引起的植物病害。
这些病原体可以包括:
卵菌纲,包括疫霉病,如由辣椒疫霉菌、致病疫霉菌、大豆疫霉菌、草莓疫莓菌(Phytophthora fragariae)、烟草疫霉菌(Phytophthora nicotianae)、樟疫霉(Phytophthora cinnamomi)、柑橘生疫霉(Phytophthora citricola)、柑橘褐腐疫霉(Phytophthora citrophthora)和马铃薯绯腐病菌(Phytophthora erythroseptica)引起的那些;腐霉病,如由瓜果腐霉菌、强雄腐霉菌(Pythium arrhenomanes)、禾生腐霉菌、畸雌腐霉菌(Pythium irregulare)和终极腐霉菌引起的那些;由霜霉目如大葱霜霉菌(Peronospora destructor)、白菜霜霉菌、葡萄霜霉菌、向日葵霜霉菌、黄瓜霜霉菌、白锈菌(Albugo candida)、水稻霜霉病和莴苣霜霉菌引起的病害;以及其他,如螺壳状丝囊霉、Labyrinthula zosterae、高梁霜指霉(Peronosclerospora sorghi)和禾生指梗霉(Sclerospora graminicola)。
子囊菌纲,包括斑纹病、斑点病、瘟病或疫病和/或腐病,例如由如下引起的那些:格孢菌目如大蒜白斑病菌(Stemphylium solani)、Stagonospora tainanensis、油橄榄环梗孢菌、玉米大斑病菌(Setosphaeria turcica)、Pyrenochaeta lycoperisici、枯叶格孢腔菌、实腐茎点霉(Phoma destructiva)、Phaeosphaeria herpotrichoides、Phaeocryptocus gaeumannii、Ophiosphaerella graminicola、小麦全蚀病(Ophiobolusgraminis)、十字花科小球腔菌(Leptosphaeria maculans)、软腐病菌(Hendersoniacreberrima)、壳针孢叶枯病菌(Helminthosporium triticirepentis)、玉米大斑病菌(Setosphaeria turcica)、大豆内脐蠕孢(Drechslera glycines)、西瓜蔓枯病菌(Didymella bryoniae)、油橄榄孔雀斑病菌(Cycloconium oleagineum)、多主棒孢菌、禾旋孢腔菌、火龙果黑斑病菌(Bipolaris cactivora)、苹果黑星病菌、圆核腔菌、燕麦草核腔菌(Pyrenophora tritici-repentis)、互隔链格孢菌、芸苔链格孢菌(Alternariabrassicicola)、茄链格孢菌和西红柿链格孢菌(Alternaria tomatophila);煤炱目(Capnodiales)如小麦壳针孢、颖枯壳针孢、大豆壳针孢(Septoria glycines)、落花生尾孢菌(Cercospora arachidicola)、大豆灰斑病菌、玉米灰斑病菌、荠白斑病菌(Cercosporella capsellae)以及麦叶白霉(Cercosporella herpotrichoides)、桃疮痂病菌(Cladosporium carpophilum)、散生枝孢(Cladosporium effusum)、褐孢霉(Passalorafulva)、尖孢枝孢(Cladosporium oxysporum)、Dothistroma septosporum、葡萄褐斑病菌(Isariopsis clavispora)、香蕉黑条叶斑病菌、禾生球腔菌(Mycosphaerellagraminicola)、散梗菌绒孢菌(Mycovellosiella koepkeii)、Phaeoisariopsisbataticola、葡萄褐斑病菌(Pseudocercospora vitis)、小麦基腐病菌、甜菜叶斑病菌、柱隔孢叶斑病菌(Ramularia collo-cygni);大角间座壳目如小麦全蚀病菌、稻瘟病菌(Magnaporthe grisea)、稻梨孢;间座壳目如榛子东部枯萎病菌、Apiognomoniaerrabunda、Cytospora platani、大豆北方茎溃疡病菌、毁灭性座盘孢(Disculadestructiva)、草莓日规壳菌(Gnomonia fructicola)、葡萄苦腐病菌、核桃黑盘壳菌(Melanconium juglandinum)、葡萄生拟茎点菌(Phomopsis viticola)、胡桃溃疡病菌(Sirococcus clavigignenti-juglandacearum)、干孢盾壳椿启介菌(Tubakia dryina)、Dicarpella spp.、苹果树腐烂病菌(Valsa ceratosperma);以及其他,如Actinothyriumgraminis、豌豆壳二孢、黄曲霉、烟曲霉菌、构巢曲霉、番木瓜座糙孢菌、叶斑病菌(Blumeriella jaapii)、假丝酵母属物种、煤炱病菌(Capnodium ramosum)、Cephaloascusspp.、麦类条斑病菌(Cephalosporium gramineum)、奇异长喙壳(Ceratocystisparadoxa)、毛壳菌属物种、拟白膜盘菌(Hymenoscyphus pseudoalbidus)、球孢子菌属物种、李属柱孢霉(Cylindrosporium padi)、双壳菌(Diplocarpon malae)、Drepanopezizacampestris、痂囊腔菌(Elsinoe ampelina)、黑附球菌、表皮癣菌属物种、葡萄顶枯病、白地霉、禾谷绒座壳(Gibellina cerealis)、高粱胶尾孢(Gloeocercospora sorghi)、煤烟病菌(Gloeodes pomigena)、Gloeosporium perennans;毒麦内生真菌(Gloeotiniatemulenta)、Griphospaeria corticola、利尼球梗孢(Kabatiella lini)、小孢粘束孢(Leptographium microsporum)、Leptosphaerulinia crassiasca、扰乱散斑壳(Lophodermium seditiosum)、禾谷盘二孢菌(Marssonina graminicola)、雪霉叶枯菌(Microdochium nivale)、美澳型核果褐腐病菌(Monilinia fructicola)、稻云形病(Monographella albescens)、甜瓜黑点根腐病菌(Monosporascus cannonballus)、丝环盘菌属物种(Naemacyclus spp.)、新榆枯萎病菌(Ophiostoma novo-ulmi)、巴西副球孢子菌(Paracoccidioides brasiliensis)、扩展青霉(Penicillium expansum)、杜鹃盘多毛孢霉(Pestalotia rhododendri)、霉样真霉属物种(Petriellidium spp.)、无柄盘菌属物种(Pezicula spp.)、大豆茎褐腐病菌(Phialophora gregata)、仁果黑痣菌(Phyllachorapomigena)、杂食动物瘤梗孢(Phymatotrichum omnivora)、隐秘囊孢菌(Physalosporaabdita)、烟草囊孢壳(Plectosporium tabacinum)、马铃薯皮斑病菌(Polyscytalumpustulans)、苜蓿假盘菌(Pseudopeziza medicaginis)、芸薹埋核盘菌(Pyrenopezizabrassicae)、高粱座枝孢(Ramulispora sorghi)、花旗松藩叶病菌(Rhabdoclinepseudotsugae)、大麦云纹病菌(Rhynchosporium secalis)、稻帚枝杆孢(Sacrocladiumoryzae)、足放线病菌属物种(Scedosporium spp.)、仁果裂盾菌(Schizothyrium pomi)、核盘菌(Sclerotinia sclerotiorum)、小核盘菌(Sclerotinia minor);小核菌属物种(Sclerotium spp.)、雪腐病核瑚菌(Typhula ishikariensis)、玛丽盘双端毛孢(Seimatosporiummariae)、Lepteutypa cupressi、Septocyta ruborum、鳄梨疮痂病菌(Sphaceloma perseae)、Sporonema phacidioides、千年枣眼点病菌(Stigminapalmivora)、Tapesia yallundae、梨外囊菌(Taphrina bullata)、棉花黑根腐病菌(Thielviopsis basicola)、Trichoseptoria fructigena、蝇粪病菌(Zygophialajamaicensis);白粉病,例如由白粉菌目如小麦白粉病菌、蓼白粉病菌、葡萄钩丝壳、黄瓜白粉病菌(Sphaerotheca fuligena)、白叉丝单囊壳、Podospaera macularis、二孢白粉菌(Golovinomyces cichoracearum)、鞑靼内丝白粉菌(Leveillula taurica)、扩散叉丝壳、Oidiopsis gossypii、榛球针壳(Phyllactinia guttata)以及Oidium arachidis引起的那些;霉,例如由葡萄座腔菌如小穴壳菌(Dothiorella aromatica)、连续色二孢(Diplodiaseriata)、比德瓦里球座菌(Guignardia bidwellii)、灰葡萄孢菌(Botrytis cinerea)、大葱孢盘菌(Botryotinia allii)、蚕豆孢盘菌(Botryotinia fabae)、扁桃壳梭菌(Fusicoccum amygdali)、龙眼焦腐病菌(Lasiodiplodia theobromae)、茶生大茎点霉(Macrophoma theicola)、菜豆壳球孢菌、葫芦科叶点霉(Phyllosticta cucurbitacearum)引起的那些;炭疽病,例如由小丛壳(Glommerelales)如盘长孢状刺盘孢、瓜类炭疽菌(Colletotrichum lagenarium)、棉花炭疽病菌、围小丛壳、以及禾生炭疽菌引起的那些;以及枯萎病或疫病,例如由肉座菌目如笔直顶孢霉、紫麦角菌、黄色镰刀菌、禾谷镰刀菌、大豆猝死综合症病菌(Fusarium virguliforme)、尖孢镰刀菌、胶孢镰刀菌、古巴尖孢镰孢(Fusarium oxysporum f.sp.cubense)、Gerlachia nivale、藤仓赤霉、玉米赤霉菌、胶枝霉属物种、疣孢漆斑菌、Nectria ramulariae、绿色木霉、粉红聚端孢菌以及鳄梨根腐病原菌(Verticillium theobromae)引起的那些。
担子菌纲,包括黑粉病例如由黑粉菌目如稻曲病菌(Ustilaginoidea virens)、大麦散黑穗病菌(Ustilago nuda)、小麦散黑穗菌(Ustilago tritici)、玉米黑粉菌(Ustilago zeae)引起的那些,锈病例如由柄锈菌如无花果蜡锈菌(Cerotelium fici)、云杉帚锈病菌(Chrysomyxa arctostaphyli)、番薯鞘锈菌(Coleosporium ipomoeae)、咖啡驼孢锈菌(Hemileia vastatrix)、落花生柄锈菌(Puccinia arachidis)、Pucciniacacabata、禾柄锈菌(Puccinia graminis)、隐匿柄锈菌(Puccinia recondita)、高粱柄锈菌(Puccinia sorghi)、大麦柄锈菌(Puccinia hordei)、大麦条形柄锈菌(Pucciniastriiformis f.sp.Hordei)、小麦条形柄锈菌(Puccinia striiformis f.sp.Secalis)、榛膨痂锈菌(Pucciniastrum coryli)引起的那些;或锈菌目如松疱锈病菌(Cronartiumribicola)、植物受桧胶锈菌(Gymnosporangium juniperi-viginianae)、杨树叶锈病菌(Melampsora medusae)、豆薯层锈菌(Phakopsora pachyrhizi)、短尖多胞锈菌(Phragmidiummucronatum)、Physopella ampelosidis、变色疣双胞锈菌(Tranzscheliadiscolor)以及蚕豆单孢锈菌(Uromyces viciae-fabae)引起的那些;以及其他腐病和病害,例如由隐球菌属物种、茶饼病菌、Marasmiellus inoderma、小菇属物种、丝黑穗病菌(Sphacelotheca reiliana)、雪腐病核瑚菌(Typhula ishikariensis)、冰草条黑粉菌(Urocystis agropyri)、Itersonilia perplexans、伏革菌(Corticiuminvisum)、地衣状伏革菌(Laetisaria fuciformis)、Waitea circinata、立枯丝核菌、Thanetephoruscucurmeris、大丽花叶黑粉菌(Entyloma dahliae)、Entylomella microspora、沼湿草尾孢黑粉菌(Neovossia moliniae)和小麦网腥黑穗病菌(Tilletia caries)引起的那些。
芽枝霉纲,如玉蜀黍节壶菌(Physoderma maydis)。
毛霉菌纲,如瓜笄霉菌(Choanephora cucurbitarum);毛霉属物种;少根根霉,
连同由与以上列出的那些紧密相关的其他物种和属引起的病害。
以上和以下对“禾生球腔菌”或“小麦壳针孢”的任何提及应理解为对小麦发酵壳针孢(Zymoseptoria tritici)(正确的分类学名称)的提及。
雪腐明梭孢(雪霉叶枯菌)是真菌植物病原体,其在所有的发育阶段期间攻击谷物,引起各种病害尤其如苗枯病、雪腐病、根腐病、以及赤霉病(ear blight)。
玉米赤霉菌(无性型:禾谷镰刀菌)是真菌植物病原体,其引起麦赤霉病(fusariumhead blight)(在小麦和大麦上的毁灭性病害)。而黄色镰刀菌同样是真菌植物病原体和苗枯病、根腐病、赤霉病、茎腐病、常见根腐病以及谷物的其他病害的致病病原,并且还是麦赤霉病的致病病原。麦赤霉病(FHB),也称为疮痂病,是小粒谷物(包括小麦、大麦、燕麦、黑麦、玉米、黑小麦、金丝雀草籽和一些饲草)的真菌病害。
除了它们的杀真菌活性之外,这些化合物和包含它们的组合物还可以具有对抗细菌如梨火疫病菌、软腐欧文氏菌(Erwinia caratovora)、野油菜黄单胞菌、丁香假单胞菌、马铃薯疮痂病菌(Strptomyces scabies)和其他相关物种以及某些原生动物的活性。
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、玉米(maize,corn)、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、灌木以及树;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。
根据本发明的有用植物和/或目标作物包括常规的连同遗传增强或遗传工程处理的品种,例如像抗虫的(例如Bt.和VIP品种)连同抗病的、耐受除草剂的(例如抗草甘膦和抗草铵膦的玉米品种,以商标名和/>可商购)以及耐受线虫的品种。通过举例的方式,适合的遗传增强或遗传工程处理的作物品种包括Stoneville5599BR棉花和Stoneville 4892BR棉花品种。
术语“有用植物”和/或“目标作物”应理解为还包括由于常规育种方法或基因工程方法致使对除草剂(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、氟磺隆和三氟啶磺隆、EPSPS(5-烯醇-丙酮酰-莽草酸-3-磷酸-合酶(5-enol-pyrovyl-shikimate-3-phosphate-synthase))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抗草甘膦和抗草铵膦的玉米品种,以商标名/> 和/>可商购。
术语“有用植物”和/或“目标作物”应理解为包括天然地或已经致使对有害昆虫有抗性的那些。这包括通过使用重组DNA技术转化从而例如能够合成一种或多种选择性作用毒素的植物,这些毒素是如从例如产毒素的细菌已知的。可以被表达的毒素的实例包括δ-内毒素,营养期杀虫蛋白(Vip),细菌定殖线虫的杀虫蛋白,以及由蝎子、蛛形纲动物、黄蜂和真菌产生的毒素。已经被修饰为表达苏云金芽孢杆菌毒素的作物的实例是Bt maize(先正达种子公司(Syngenta Seeds))。包括编码杀虫抗性并且由此表达多于一种毒素的多于一种基因的作物的实例是/>(先正达种子公司)。作物或其种子材料还可以是对多种类型的有害生物具有抗性(当通过遗传修饰产生时的所谓的叠加转基因事件)。例如,植物可以具有表达杀虫蛋白同时耐受除草剂的能力,例如Herculex/>(陶氏益农公司(Dow AgroSciences),先锋良种国际公司(Pioneer Hi-Bred International))。
术语“有用植物”和/或“目标作物”应理解为还包括已经通过使用重组DNA技术进行转化使得它们能够合成具有选择性活性的抗病原物质,例如像所谓的“致病机理相关的蛋白”(PRP,参见例如EP-A-0 392 225)的有用植物。此类抗病原物质和能够合成此类抗病原物质的转基因植物的实例是已知的,例如从EP-A-0 392 225、WO 95/33818以及EP-A-0353 191已知的。生产此类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于例如以上提及的公开物中。
可由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虫蛋白;或者来自苏云金芽孢杆菌的杀虫蛋白,如δ-内毒素,例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或者营养期杀虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A;或细菌定植线虫的杀虫蛋白,例如光杆状菌属物种(Photorhabdusspp.)或致病杆菌属物种(Xenorhabdus spp.),如发光杆菌(Photorhabdus luminescens)、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;凝集素类(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、玉米-RIP、相思豆毒素、丝瓜籽蛋白、皂草素或异株泻根毒蛋白;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。
进一步地,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置换。在这种氨基酸置换中,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,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更多实例披露于例如EP-A-0 374753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878和WO 03/052073中。
用于制备此类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于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。
包括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)。
含有一种或多种编码杀虫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。此类植物的实例是:(玉米品种,表达Cry1Ab毒素);YieldGard/>(玉米品种,表达Cry3Bb1毒素);YieldGard/>(玉米品种,表达Cry1Ab和Cry3Bb1毒素);/>(玉米品种,表达Cry9C毒素);Herculex/>(玉米品种,表达Cry1Fa2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)、/>CBAdvantage(Bt11玉米螟(CB)性状)以及/>
此类转基因作物的另外的实例是:
1.Bt11玉米,来自先正达种子公司(Syngenta Seeds SAS),霍比特路(Chemin del'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玉米还转基因表达PAT酶以获得对除草剂草铵膦铵盐的耐受性。
2.Bt176玉米,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玉米还转基因表达酶PAT以获得对除草剂草铵膦铵盐的耐受性。
3.MIR604玉米,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米。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。此类转基因玉米植物的制备描述于WO 03/018810中。
4.MON 863玉米,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玉米,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。遗传修饰的玉米,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铵盐的耐受性。
7.NK603×MON 810玉米,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米品种构成。NK603×MON 810玉米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,或者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、叶子和果实。
术语“植物繁殖材料”应理解为表示植物的生殖部分,如种子(其可以用于植物的繁殖),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”应理解为表示种子。
本文中所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 ProtectionCouncil)2009已知的。
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、尘粉剂、颗粒剂以及还有胶囊(例如在聚合物质中)。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。此类配制品包括抗沉降剂和分散剂,并且可以进一步包括湿润剂以增强活性,以及消泡剂和晶体生长抑制剂。在使用时,将这些浓缩物稀释在水中,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%。
可湿性粉剂是呈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%至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,并且通常不用稀释地施用至需要处理的区域。用于颗粒配制品的典型载体包括砂、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。
尘粉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括溶剂。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剂。
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按重量计组成配制品的从0.1%到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、润湿剂、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,如壬基苯酚-C18乙氧基化物;醇-环氧烷加成产物,如十三烷醇-C16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、防泡剂、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。
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)的化合物通常以组合物的形式使用并且可与另外的化合物同时地或顺序地施用于作物区域或有待处理的植物。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)的化合物可以按用于控制或保护抵抗植物病原性微生物的(杀真菌的)组合物的形式使用,这些组合物包含至少一种具有式(I)的化合物或至少一种优选的如上所定义的各种化合物作为活性成分(以游离形式或以农用化学上可用的盐形式),并且包含至少一种上述辅助剂。
因此,本发明提供了一种组合物,优选地是杀真菌组合物,其包含至少一种具有式(I)的化合物和农业上可接受的载体以及任选地辅助剂。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,除了具有式(I)的化合物,所述组合物还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:1,2,4-噻二唑、2,6-二硝基苯胺、酰基丙氨酸、脂族含氮化合物、脒、氨基嘧啶醇、苯胺、苯胺-嘧啶类、蒽醌类、抗生素、芳基-苯基酮、苯甲酰胺、苯-磺酰胺、苯并咪唑、苯并噻唑、苯并硫代二唑(benzothiodiazole)、苯并噻吩、苯并吡啶、苯并噻二唑(benzthiadiazole)、苄基氨基甲酸酯、丁胺、氨基甲酸酯、甲酰胺、环丙酰菌胺(carpropamid)、氯腈(chloronitrile)、肉桂酸酰胺、含铜化合物、氰基乙酰胺、氰基丙烯酸酯、氰基咪唑、氰基亚甲基-噻唑烷、二腈(dicarbonitrile)、二甲酰胺、二甲酰亚胺、二甲基氨基磺酸盐、二硝基苯酚碳酸盐、二硝基苯酚、二硝基苯基巴豆酸酯、二苯基磷酸酯、二噻英并化合物、二硫代氨基甲酸酯、二硫醚、二硫戊环、乙基-氨基-噻唑甲酰胺、乙基-膦酸酯、呋喃甲酰胺、吡喃葡萄糖基、葡萄糖醛酸基、戊二腈、胍、除草剂/植物生长调节剂、己吡喃糖基抗生素、羟基(2-氨基)嘧啶、羟基苯胺、羟基异噁唑、咪唑、咪唑啉酮、杀虫剂/植物生长调节剂、异苯并呋喃酮、异噁唑烷基-吡啶、异噁唑啉、马来酰亚胺、扁桃酸酰胺、果胶衍生物、吗啉、去甲吗啉、N-苯基氨基甲酸酯、有机锡化合物、氧硫杂环己烷甲酰胺、噁唑、噁唑烷二酮、苯酚、苯氧基喹啉、苯基-乙酰胺、苯基酰胺、苯基苯甲酰胺、苯基-氧代-乙基-噻吩酰胺、苯基吡咯、苯基脲、硫代磷酸酯、磷酸、邻苯二甲酸、邻苯二甲酰亚胺、吡啶酰胺、哌嗪、哌啶、植物提取物、多氧霉素、丙酰胺、邻苯二甲酰亚胺、吡唑-4-甲酰胺、吡唑啉酮、哒嗪酮、吡啶、吡啶甲酰胺、吡啶基-乙基苯甲酰胺、嘧啶胺、嘧啶、嘧啶-胺、嘧啶酮-腙、吡咯烷、吡咯喹啉、喹唑啉酮、喹啉、喹啉衍生物、喹啉-7-甲酸、喹喔啉、螺缩酮胺、嗜球果伞素、氨磺酰三唑、磺酰胺、四唑肟、噻二嗪、噻二唑甲酰胺、噻唑甲酰胺、硫氰酸酯、噻吩甲酰胺、甲苯酰胺、三嗪、三唑苯并噻唑、三唑、三唑-硫酮、三唑-嘧啶胺、缬氨酰胺氨基甲酸酯、甲基膦酸铵、含砷化合物、苯并咪唑基氨基甲酸酯、羰腈、羧酰苯胺、甲酰胺酰胺、羧基苯酰胺、二苯基吡啶、呋喃酰苯胺、肼甲酰胺、咪唑啉乙酸酯、间苯二甲酸酯、异噁唑酮、汞盐、有机汞化合物、有机磷酸酯、噁唑烷二酮、戊基磺酰基苯、苯基苯甲酰胺、硫代膦酸酯、硫代磷酸酯、吡啶甲酰胺、吡啶基糠基醚、吡啶基甲基醚、SDHI、噻二嗪烷硫酮、噻唑烷。
合适的另外的活性成分的实例还包括以下:选自由以下组成的物质组的化合物:石油油料、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、氯杀螨、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、内吸磷-S-甲基砜、抑菌灵、敌敌畏、二克磷(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、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、发硫磷、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、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、环丁腈(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、芹菜夜蛾NPV、原樱翅缨小蜂、短距蚜小蜂、棉蚜寄生蜂、食蚜瘿蚊、苜蓿银纹夜蛾NPV、球形芽孢杆菌、布氏白僵菌、普通草蛉、孟氏隐唇瓢虫、苹果蠹蛾GV、西伯利亚离颚茧蜂、豌豆潜叶蝇姬小蜂、丽蚜小蜂、桨角蚜小蜂、嗜菌异小杆线虫和大异小杆线虫、斑长足瓢虫、橘粉介壳虫寄生蜂、盲蝽、甘蓝夜蛾NPV、黄阔柄跳小蜂、黄绿绿僵菌、金龟子绿僵菌小孢变种、欧洲新松叶蜂NPV和红头新松叶蜂NPV、小花蝽属物种、玫烟色拟青霉、智利小植绥螨、毛蚊线虫、小卷蛾斯氏线虫、夜蛾斯氏线虫、格氏线虫、锐比斯氏线虫、里氏斯氏线虫(Steinernemariobravis)、蝼蛄斯氏线虫、斯氏线虫属物种、赤眼蜂属物种、西方盲走螨、蜡蚧轮枝菌、唑磷嗪、双(氮丙啶)甲氨基膦硫化物、白消安、迪麦替夫、六甲蜜胺、六甲磷、甲基涕巴、甲硫涕巴、甲基唑磷嗪、不孕啶、氟幼脲、涕巴、硫代六甲磷、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、可得蒙、诱蝇酮、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、诱杀烯混剂、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、齿小蠹二烯醇、小蠢烯醇、金龟子性诱剂、三甲基二氧三环壬烷、夜蛾诱剂(litlure)、粉纹夜蛾性诱剂、诱杀酯、蒙托么克酸(megatomoic acid)、诱虫醚、诱虫烯、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、椰蛀犀金龟聚集信息素、非乐康、诱虫环、索迪叮(sordidin)、食菌甲诱醇、十四碳-11-烯-1-基乙酸酯、地中海实蝇引诱剂、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、trunc-call、2-(辛基硫代)-乙醇、避蚊酮、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、邻苯二甲酸二甲酯、乙基己二醇、己脲、甲喹丁、甲基新癸酰胺、草氨酸盐、派卡瑞丁、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、艾氏剂、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-resmethrin)、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、赛灭磷、d-胺菊酯、DAEP、棉隆、脱甲基克百威(decarbofuran)、除线特、异氯磷、除线磷、dicresyl、环虫腈、狄氏剂、二乙基5-甲基吡唑-3-基磷酸酯、喘定(dilor)、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、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、恶唑磷、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、以及氯氟醚菊酯、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、2-氟-N-(3-甲氧基苯基)-9H-嘌呤-6-胺、苯氯噻、细胞分裂素、DCIP、糠醛、异酰胺磷、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、氯吲哚酰肼、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、胡椒基丁醚、增效醛、丙基异构体、S421、增效散、芝麻林素、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、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(simeconazole)、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(enestroburin)、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、克菌丹、唑呋草、灭菌丹、对甲抑菌灵、波尔多混合剂、氧化铜、代森锰铜、喹啉铜、酞菌酯、克瘟散、异稻瘟净、氯瘟磷、甲基立枯磷、敌菌灵、苯噻菌胺、灭瘟素(blasticidin)、地茂散(chloroneb)、百菌清、环氟菌胺、霜脲氰、cyclobutrifluram、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)、氟吡菌胺(fluopicolide)、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(flubeneteram)、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、isoflucypram、异噻菌胺、敌派美创(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(fluindapyr)、甲香菌酯(jiaxiangjunzhi)、利本米昔安(lvbenmixianan)、二氯苯噻唑(dichlobentiazox)、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)、特罗卡普(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]甲磺酸酯、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、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(florylpicoxamid)、苯吡克咪徳(fenpicoxamid)、异丁乙氧喹啉、伊氟芬喹(ipflufenoquin)、奎富马林(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、甲酰四脯氨酸(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、氟沙普罗林(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、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、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、N-辛基-N'-[2-(辛基氨基)乙基]乙烷-1,2-二胺、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、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-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']二吡咯-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]硫代苯甲酰胺;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)。
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、埃玛菌素、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喹酰胺/马可氟汀类驱蠕虫药剂的衍生物及类似物以及抗寄生虫噁唑啉(如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一般种类二氧代吗啉抗寄生虫剂的衍生物及类似物(如WO96/15121中所述)以及还与驱蠕虫活性的环酯肽(如WO 96/11945、WO 93/19053、WO 93/25543、EP 0 626 375、EP 0 382173、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、异丙磷、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、磷克、亚胺硫磷、磷胺、甲拌磷、肟硫磷、虫螨磷、虫螨磷-甲基、丙溴磷、丙虫磷、proetamphos、丙硫磷、吡唑硫磷、哒嗪硫磷、喹硫磷、硫灭克磷、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、三氟氯氰菊酯、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、三氟氯氰菊酯、λ-高效氯氟氰菊酯、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、敌螨酯、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 sspaizawai)、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:恩诺沙星、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、泰妙菌素、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(ceftiour)、卡洛芬、氰氟虫腙、吡喹酮(praziquarantel)、三氯苯达唑、氟甲磺姆(flumetylsulforim)、氟氧康唑(fluoxytioconazole)、氟芬氧泽(flufenoxadiazam)、甲匹康米德(metarylpicoxamid)。
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”意指选自由如在表A1至A7或(下)表E中所示的化合物组成的组中的一种化合物:
选自由以下组成的物质组的化合物:石油油料+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、果螨磷+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、氯杀螨+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、内吸磷-S-甲基砜+TX、抑菌灵+TX、敌敌畏+TX、二克磷(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、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、发硫磷+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、环丁腈(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+TX、芹菜夜蛾NPV+TX、原樱翅缨小蜂+TX、短距蚜小蜂+TX、棉蚜寄生蜂+TX、食蚜瘿蚊+TX、苜蓿银纹夜蛾NPV+TX、球形芽孢杆菌+TX、布氏白僵菌+TX、普通草蛉+TX、孟氏隐唇瓢虫+TX、苹果蠹蛾GV+TX、西伯利亚离颚茧蜂+TX、豌豆潜叶蝇姬小蜂+TX、丽蚜小蜂+TX、桨角蚜小蜂+TX、嗜菌异小杆线虫和大异小杆线虫+TX、斑长足瓢虫+TX、橘粉介壳虫寄生蜂+TX、盲蝽+TX、甘蓝夜蛾NPV+TX、黄阔柄跳小蜂+TX、黄绿绿僵菌+TX、金龟子绿僵菌小孢变种+TX、欧洲新松叶蜂NPV和红头新松叶蜂NPV+TX、小花蝽属物种+TX、玫烟色拟青霉+TX、智利小植绥螨+TX、毛蚊线虫+TX、小卷蛾斯氏线虫+TX、夜蛾斯氏线虫+TX、格氏线虫+TX、锐比斯氏线虫+TX、里氏斯氏线虫(Steinernemariobravis)+TX、蝼蛄斯氏线虫+TX、斯氏线虫属物种+TX、赤眼蜂属物种+TX、西方盲走螨+TX、蜡蚧轮枝菌+TX、唑磷嗪+TX、双(氮丙啶)甲氨基膦硫化物+TX、白消安+TX、迪麦替夫+TX、六甲蜜胺+TX、六甲磷+TX、甲基涕巴+TX、甲硫涕巴+TX、甲基唑磷嗪+TX、不孕啶+TX、氟幼脲+TX、涕巴+TX、硫代六甲磷+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+TX、可得蒙+TX、诱蝇酮+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+TX、诱杀烯混剂+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+TX、齿小蠹二烯醇+TX、小蠢烯醇+TX、金龟子性诱剂+TX、三甲基二氧三环壬烷+TX、夜蛾诱剂(litlure)+TX、粉纹夜蛾性诱剂+TX、诱杀酯+TX、蒙托么克酸(megatomoic acid)+TX、诱虫醚+TX、诱虫烯+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+TX、椰蛀犀金龟聚集信息素+TX、非乐康+TX、诱虫环+TX、索迪叮(sordidin)+TX、食菌甲诱醇+TX、十四碳-11-烯-1-基乙酸酯+TX、地中海实蝇引诱剂+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、trunc-call+TX、2-(辛基硫代)-乙醇+TX、避蚊酮+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+TX、邻苯二甲酸二甲酯+TX、乙基己二醇+TX、己脲+TX、甲喹丁+TX、甲基新癸酰胺+TX、草氨酸盐+TX、派卡瑞丁+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、艾氏剂+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-resmethrin)+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、CS708+TX、苯腈磷+TX、杀螟腈+TX、环虫菊+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+TX、异氯磷+TX、除线磷+TX、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(dilor)+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 1642+TX、EMPC+TX、EPBP+TX、etaphos+TX、乙硫苯威+TX、甲酸乙酯+TX、二溴乙烷+TX、二氯乙烷+TX、环氧乙烷+TX、EXD+TX、皮蝇磷+TX、乙苯威+TX、杀螟硫磷+TX、氧嘧酰胺(fenoxacrim)+TX、吡氯氰菊酯+TX、丰索磷+TX、乙基倍硫磷+TX、氟氯双苯隆(flucofuron)+TX、丁苯硫磷+TX、磷砒酯+TX、丁环硫磷+TX、呋线威+TX、抗虫菊+TX、双胍辛盐+TX、双胍辛乙酸盐+TX、四硫代碳酸钠+TX、苄螨醚+TX、HCH+TX、HEOD+TX、七氯+TX、速杀硫磷+TX、HHDN+TX、氰化氢+TX、喹啉威+TX、IPSP+TX、氯唑磷+TX、碳氯灵+TX、异艾氏剂+TX、异柳磷+TX、移栽灵+TX、稻瘟灵+TX、恶唑磷+TX、保幼激素I+TX、保幼激素II+TX、保幼激素III+TX、氯戊环+TX、烯虫炔酯+TX、砷酸铅+TX、溴苯磷+TX、啶虫磷+TX、噻唑磷+TX、间异丙苯基甲基氨基甲酸酯+TX、磷化镁+TX、叠氮磷+TX、甲基减蚜磷+TX、灭蚜硫磷+TX、氯化亚汞+TX、甲亚砜磷+TX、威百亩+TX、威百亩钾盐+TX、威百亩钠盐+TX、甲基磺酰氟+TX、丁烯胺磷+TX、甲氧普林+TX、甲醚菊酯+TX、甲氧滴滴涕+TX、异硫氰酸甲酯+TX、甲基氯仿+TX、二氯甲烷+TX、恶虫酮+TX、灭蚁灵+TX、奈肽磷+TX、萘+TX、NC-170+TX、烟碱+TX、硫酸烟碱+TX、硝虫噻嗪+TX、原烟碱+TX、O-5-二氯-4-碘苯基O-乙基乙基硫代膦酸酯+TX、O,O-二乙基O-4-甲基-2-氧代-2H-苯并吡喃-7-基硫代膦酸酯+TX、O,O-二乙基O-6-甲基-2-丙基嘧啶-4-基硫代膦酸酯+TX、O,O,O',O'-四丙基二硫代焦磷酸酯+TX、油酸+TX、对-二氯苯+TX、甲基对硫磷+TX、五氯苯酚+TX、月桂酸五氯苯酯+TX、PH 60-38+TX、芬硫磷+TX、对氯硫磷+TX、磷化氢+TX、甲基辛硫磷+TX、甲胺嘧磷+TX、多氯二环戊二烯异构体+TX、亚砷酸钾+TX、硫氰酸钾+TX、早熟素I+TX、早熟素II+TX、早熟素III+TX、酰胺嘧啶磷+TX、丙氟菊酯+TX、猛杀威+TX、丙硫磷+TX、吡菌磷+TX、反灭虫菊+TX、苦木提取物(quassia)+TX、喹硫磷-甲基+TX、畜宁磷+TX、碘柳胺+TX、苄呋菊脂+TX、鱼藤酮+TX、噻嗯菊酯+TX、鱼尼汀+TX、利阿诺定+TX、沙巴藜芦(sabadilla)+TX、八甲磷+TX、克线丹+TX、SI-0009+TX、噻丙腈+TX、亚砷酸钠+TX、氰化钠+TX、氟化钠+TX、六氟硅酸钠+TX、五氯苯酚钠+TX、硒酸钠+TX、硫氰酸钠+TX、磺苯醚隆(sulcofuron)+TX、磺苯醚隆钠盐(sulcofuron-sodium)+TX、硫酰氟+TX、硫丙磷+TX、焦油+TX、噻螨威+TX、TDE+TX、丁基嘧啶磷+TX、双硫磷+TX、环戊烯丙菊酯+TX、四氯乙烷+TX、噻氯磷+TX、杀虫环+TX、杀虫环草酸盐+TX、虫线磷+TX、杀虫单+TX、杀虫单钠+TX、四溴菊酯+TX、反氯菊酯+TX、唑蚜威+TX、异皮蝇磷-3(trichlormetaphos-3)+TX、毒壤膦+TX、混杀威+TX、三氟甲氧威(tolprocarb)+TX、氯啶菌酯+TX、烯虫硫酯+TX、藜芦定+TX、藜芦碱+TX、XMC+TX、泽他米林(zetamethrin)+TX、磷化锌+TX、唑虫磷+TX、以及氯氟醚菊酯+TX、四氟醚菊酯+TX、双(三丁基锡)氧化物+TX、溴乙酰胺+TX、磷酸铁+TX、氯硝柳胺-乙醇胺+TX、三丁基氧化锡+TX、吡吗啉+TX、蜗螺杀+TX、1,2-二溴-3-氯丙烷+TX、1,3-二氯丙烯+TX、3,4-二氯四氢噻吩1,1-二氧化物+TX、3-(4-氯苯基)-5-甲基罗丹宁+TX、5-甲基-6-硫代-1,3,5-噻二嗪-3-基乙酸+TX、6-异戊烯基氨基嘌呤+TX、2-氟-N-(3-甲氧基苯基)-9H-嘌呤-6-胺+TX、苯氯噻+TX、细胞分裂素+TX、DCIP+TX、糠醛+TX、异酰胺磷+TX、激动素+TX、疣孢漆斑菌组合物+TX、四氯噻吩+TX、二甲苯酚+TX、玉米素+TX、乙基黄原酸钾+TX、阿拉酸式苯+TX、阿拉酸式苯-S-甲基+TX、大虎杖提取物+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、胡椒基丁醚+TX、增效醛+TX、丙基异构体+TX、S421+TX、增效散+TX、芝麻林素+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(simeconazole)+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(enestroburin)+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+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+TX、代森锰铜+TX、喹啉铜+TX、酞菌酯+TX、克瘟散+TX、异稻瘟净+TX、氯瘟磷+TX、甲基立枯磷+TX、敌菌灵+TX、苯噻菌胺+TX、灭瘟素(blasticidin)+TX、地茂散(chloroneb)+TX、百菌清+TX、环氟菌胺+TX、霜脲氰+TX、cyclobutrifluram+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(flubeneteram)+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、isoflucypram+TX、异噻菌胺+TX、敌派美创(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(fluindapyr)+TX、甲香菌酯(jiaxiangjunzhi)+TX、利本米昔安(lvbenmixianan)+TX、二氯苯噻唑(dichlobentiazox)+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、特罗卡普(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]甲磺酸酯+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、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(florylpicoxamid)+TX、苯吡克咪徳(fenpicoxamid)+TX、异丁乙氧喹啉+TX、伊氟芬喹(ipflufenoquin)+TX、奎富马林(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、甲酰四脯氨酸(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、氟沙普罗林(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(amectotractin)+TX、异菌脲+TX、N-辛基-N'-[2-(辛基氨基)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+TX(这种化合物可以由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+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+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']二吡咯-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]硫代苯甲酰胺+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、氟甲磺姆(flumetylsulforim)+TX、氟氧康唑(fluoxytioconazole)+TX、氟芬氧泽(flufenoxadiazam)+TX、甲匹康米德(metarylpicoxamid)+TX。
在活性成分之后的括号中的参考号,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;英国作物保护委员会]中时,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 ofPesticide 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。
上述活性成分中的大多数通过上文中所谓的“通用名”来提及,在不同的情形中使用相应的“ISO通用名”或其他“通用名”。若名称不是“通用名”,则所使用的名称类别改为在特定化合物的圆括号中给出;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。
选自如表A1至A7或表E(下文)中所示的一种化合物的具有式(I)的化合物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,给予特别优选的是从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,特别是处于以下比率: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。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A1至A7或表E(下文)中所示的化合物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(其由单一活性成分组分的单独配制品构成)(如“桶混制剂”)施用,以及当以顺序方式(即,一个接着另一个地,在适度短时期内,如几小时或几天)施用时组合使用单一活性成分施用。施用如表A1至A7或表E(下文)中所示的化合物和一种或多种如上所述的活性成分的顺序对于实施本发明并不是至关重要的。
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;和在至少一种助剂的存在下,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定义的各种化合物的、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各种化合物的组合物的、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各种化合物(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)、或非生命材料被植物病原性微生物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,该方法包括将具有式(I)的化合物或优选的如以上定义的各种化合物作为活性成分施用至这些植物、这些植物的部分或其场所、其繁殖材料、或这些非生命材料的任何部分。
控制或预防意指将被昆虫或植物病原性微生物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(尤其是真菌有机体)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、或含有所述化合物中的至少一种的农用化学组合物。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浸泡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,可以将此类颗粒施用到灌水的稻田中。具有式(I)的化合物还可以通过用杀真菌剂的液体配制品浸渍种子或块茎、或用固体配制品对其进行包衣而施用到种子(包衣)上。
配制品(例如含有具有式(I)的化合物、以及(如果需要)固体或液体辅助剂或用于封装具有式(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补充剂(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))密切地混合和/或研磨。
组合物的施用方法,即控制上述类型的有害生物的方法,如喷雾、雾化、撒粉、刷涂、拌种、撒播或浇灌(它们被选择为适于当时环境的预期目的)以及组合物用于控制上述类型的有害生物的用途是本发明的其他主题。典型的浓度比是在0.1与1000ppm之间、优选在0.1与500ppm之间的活性成分。每公项的施用比率优选是每公项1g至2000g活性成分、更优选10至1000g/ha、最优选10至600g/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。
当本发明的组合用于处理种子时,0.001至50g具有式(I)的化合物/kg种子、优选从0.01至10g/kg种子的比率总体上是足够的。
适当地,预防性(意指在病害发展之前)或治疗性(意指在病害发展之后)施用根据本发明的包含具有式(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效力的常规缓释配制品。特别地,有待以喷雾形式施用的配制品(如水分散性浓缩物(例如EC、SC、DC、OD、SE、EW、EO等)、可湿性粉剂及颗粒剂)可以含有表面活性剂(如润湿剂和分散剂)及提供辅助效果的其他化合物,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,以适合的拌种配制品形式,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,配制品包含按重量计从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%的固体或液体配制品惰性剂和一种或多种辅助剂,该活性剂由至少具有式(I)的化合物与组分(B)和(C)一起、以及任选地其他活性剂(特别是杀微生物剂或防腐剂等)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。
实例
以下实例用来说明本发明。
本发明的某些化合物与已知的化合物的区别可以在于在低施用比率下更大的效力,这可以由本领域技术人员使用在实例中概述的实验程序,使用更低的施用比率(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)的化合物可以具有许多益处,尤其包括用于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、增加的安全特性(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“m.p.”意指熔点。LC/MS意指液相色谱-质谱,并且下面描述了装置和方法的说明。
配制品实例
将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
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在植物保护中可以使用的具有任何所需稀释度的乳液可以通过用水稀释从这种浓缩物获得。
通过将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尘粉剂。此类粉剂还可以用于种子的干拌种。
挤出机颗粒
将活性成分与辅助剂混合并且研磨,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润湿的高岭土上。以此方式获得无尘的包衣颗粒剂。
悬浮液浓缩物
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将精细研磨的活性成分与辅助剂密切地混合,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。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且通过喷雾、浇灌或浸渍保护免受微生物的侵染。
种子处理用的可流动浓缩物
溶液形式)
单偶氮-颜料钙盐 5%
硅酮油(处于在水中75%的乳液的形式) 0.2%
水 45.3%
将精细研磨的活性成分与辅助剂密切地混合,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。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且通过喷雾、浇灌或浸渍保护免受微生物的侵染。
缓慢释放的胶囊悬浮液
将28份的具有式(I)的化合物的组合与2份的芳族溶剂以及7份的甲苯二异氰酸酯/多亚甲基-多苯基异氰酸酯-混合物(8:1)进行混合。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2.8份的1,6-二氨基己烷在5.3份的水中的混合物。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包含28%的活性成分。介质胶囊的直径是8-15微米。
将所得配制品在适用于此目的的装置中作为水性悬浮液施用到种子上。
缩写清单:
Aq=水溶液
Ar=氩
br s=宽单峰
CDCl3=氯仿-d
℃=摄氏度
DCM=二氯甲烷
dd=双二重峰
DMF=二甲基甲酰胺
d=二重峰
EtOAc=乙酸乙酯
equiv.=当量
h=小时
HCl=盐酸
M=摩尔
m=多重峰
MeOD=甲醇-d
MeOH=甲醇
MgSO4=硫酸镁
min=分钟
MHz=兆赫兹
mp=熔点
NaHCO3=碳酸氢钠
NaOH=氢氧化钠
NH4Cl=氯化铵
ppm=百万分率
RT=室温
Rt=保留时间
s=单峰
t=三重峰
THF=四氢呋喃
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:
实例A1:7,8-二氟-3-[外消旋-(3S,4S)-5-氯-3,4-二甲基-3,4-二氢异喹啉-1-基]喹啉(化合物E.01)
步骤1:
在0℃向2-氯苯乙酮(5.00g,31.37mmol)在THF(50mL)和MeOH(15mL)中的溶液中添加硼氢化钠(1.21g,31.37mmol),将所得溶液升温至室温并搅拌3h。将饱和NH4Cl溶液添加到反应混合物中,并将混合物在水与EtOAc之间分配。将有机相经MgSO4干燥、过滤并浓缩以得到1-(2-氯苯基)乙醇,其不经进一步纯化而使用。
LC-MS(方法G1),Rt=1.21min,(M+H)=139。
1H NMR(400MHz,CDCl3)δppm:7.62(dd,1H),7.27-7.39(m,2H),7.18-7.26(m,1H),5.31(q,1H),2.13(s,1H),1.51(d,3H)。
步骤2:
向在0℃下冷却的1-(2-氯苯基)乙醇(5.7g,36mmol)在二乙醚(60mL)中的溶液中添加三溴化磷(2.1mL,22mmol)。将反应混合物在0℃下搅拌10min,逐渐升温至室温并在该温度搅拌90min。然后添加冰冷的水并将所得混合物快速搅拌10min。将反应混合物用EtOAc萃取,将有机相用H2O洗涤、经MgSO4干燥、过滤并减压浓缩。通过快速色谱法(二氧化硅,环己烷:EtOAc)纯化残余物以得到呈无色液体的1-(1-溴乙基)-2-氯-苯。
1H NMR(400MHz,CDCl3)δppm:7.65(dd,1H),7.21-7.39(m,3H),5.66(q,1H),2.04-2.08(m,3H)。
步骤3:
将2-甲基丙烷-2-亚磺酰胺(2.00g,16.5mmol)、MgSO4(9.93g,82.5mmol)和乙醛(1.72mL,33mmol)在DCM(33mL)中的悬浮液在室温下搅拌18h。通过过滤除去固体,并且减压浓缩滤液以得到呈橙色液体的N-亚乙基-2-甲基-丙烷-2-亚磺酰胺,其不经进一步纯化而使用。
LC-MS(方法G):Rt=0.65min,(M+H)=148。
1H NMR(400MHz,CDCl3)δppm:8.08-8.14(m,1H),2.26(d,3H),1.22(s,9H)。
步骤4:
向镁屑(0.22g,9.11mmol)在二乙醚(3mL)中的悬浮液中添加2滴二异丁基氢化铝(在甲苯中1M)。然后滴加1-(1-溴乙基)-2-氯-苯(0.80g,3.65mmol)在二乙醚(3mL)中的溶液。将反应混合物在室温下搅拌15min,然后冷却至0℃。添加在二乙醚(2mL)中的N-亚乙基-2-甲基-丙烷-2-亚磺酰胺(0.48g,3.28mmol),将反应混合物逐渐升温至室温并在室温下再搅拌2h。添加冰冷的水并用EtOAc萃取混合物。将有机相用H2O洗涤、经MgSO4干燥、过滤并减压浓缩。通过快速色谱法(二氧化硅,环己烷:EtOAc)纯化残余物以得到呈异构体混合物的N-[2-(2-氯苯基)-1-甲基-丙基]-2-甲基-丙烷-2-亚磺酰胺。
LC-MS(方法G1),Rt=1.15min(异构体1)和1.19min(异构体2),(M+H)=288。
步骤5:
向在0℃下的N-[2-(2-氯苯基)-1-甲基-丙基]-2-甲基-丙烷-2-亚磺酰胺(2.29g,7.16mmol)在MeOH(14mL)中的溶液中添加HCl(在二噁烷中4M,3.6mL)。将所得混合物升温至室温并搅拌1h。然后将反应混合物用水性NaOH(2M)溶液碱化并用EtOAc萃取。将有机相经MgSO4干燥、过滤并减压浓缩。将残余物溶解在乙腈(70mL)中并用7,8-二氟喹啉-3-甲酸(1.58g,7.55mmol)、三乙胺(2.65mL,18.9mmol)和丙基膦酸酐(在EtOAc中50%,7.64mL,12.84mmol)处理。将所得溶液在室温下搅拌6h,然后添加水并用EtOAc萃取混合物。将有机相用H2O洗涤、经MgSO4干燥、过滤并真空浓缩。通过快速色谱法(二氧化硅,环己烷:EtOAc)纯化残余物以得到N-[2-(2-氯苯基)-1-甲基-丙基]-7,8-二氟-喹啉-3-甲酰胺。
LC-MS(方法G1),Rt=1.13min,(M+H)=374。
1H NMR(400MHz,CDCl3)δppm:9.28(d,1H),8.62(t,1H),7.72(d,1H),7.51-7.56(m,1H),7.28-7.43(m,4H),7.20-7.23(m,1H),6.06-6.18(br d,1h),4.58-4.71(m,1H),3.67(quint,1H),1.38(d,3H),1.19(d,3H)。
19F NMR(377MHz,CDCl3)δppm:132.15(s,1F),150.2(s.1F)。
步骤6:
向在-5℃下的N-[2-(2-氯苯基)-1-甲基-丙基]-7,8-二氟喹啉-3-甲酰胺(0.36g,0.96mmol)在DCM(5mL)中的悬浮液中添加三氟甲磺酸酐(0.19mL,1.15mmol)。将反应混合物在-5℃下老化90min,并且然后添加2,6-二叔丁基吡啶(0.33mL,1.44mmol)。将反应混合物逐渐升温至室温并在此温度下搅拌16h。然后添加水并将混合物用EtOAc萃取。将有机相用水性NaHCO3溶液洗涤、经MgSO4干燥、过滤并真空浓缩。通过快速色谱法(二氧化硅,环己烷:EtOAc)纯化残余物以得到3-(5-氯-3,4-二甲基-3,4-二氢异喹啉-1-基)-7,8-二氟-喹啉。
LC-MS(方法G1),Rt=1.11min,(M+H)=357。
1H NMR(400MHz,CD3OD)δppm:9.13(d,1H),8.6(s,1H),7.94(ddd,1H),7.63-7-75(m,2H),7.37(t,1H),7.23-7.29(m,1H),3.8(dd,1H),3.35-3.39(m,1H),1.68(d,3H),1.11(d,3H)。
19F NMR(377MHz,CD3OD)δppm:136.16(s,1F),154.36(s.1F)。
实例A2:(3S,4S或3R,4R)-5-氯-1-(8-氟-3-喹啉基)-3,4-二甲基-3,4-二氢异喹啉(化合物E.10和E.11)
将外消旋-5-氯-1-(8-氟-3-喹啉基)-3,4-二甲基-3,4-二氢异喹啉的对映异构体通过制备型SFC(Sepiatec Prep SFC 100)经手性固定相(DaicelIC,5μm,2.0cm×25cm)分离。流动相:A:CO2 B:2-丙醇,无梯度:35% B,背压:150巴,流速:60ml/min,检测:UV 245nm,样品浓度:在MeOH/乙腈中20mg/mL,注射:1000μl。获得化合物E.10(对映异构体1,共2种)作为第一洗脱异构体,获得化合物E.11(对映异构体2,共2种)作为第二洗脱异构体。
分析方法
方法G:
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,其装备有电喷射源(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:100Da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,30×2.1mm,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G1:
在来自沃特斯公司的质谱仪(SQD、SQDII单四极杆质谱仪)上记录光谱,其装备有电喷射源(极性:正离子和负离子),毛细管电压: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:110Da至850Da)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 C18,1.8μm,30×2.1mm,温度:40℃,DAD波长范围(nm):230至400,溶剂梯度:A=水+0.05% HCOOH,B=乙腈+0.05%HCOOH:梯度:10%-100%B,在1.6min内;流量(mL/min)0.60。
方法H1:
在SFC沃特斯Acquity UPC2/QDa上记录光谱,其中在PDA检测器沃特斯AcquityUPC2上进行检测。柱:Daicel SFCIC,3μm,0.3cm×10cm,40℃,流动相:A:CO2 B:2-丙醇,无梯度:30% B,在4.8min内,ABPR:1800psi,流速:2.0ml/min,检测:240nm,样品浓度:在乙腈中1mg/mL,注射:1μL
表E:具有式(I)的化合物的熔点(mp)和/或LC/MS数据(保留时间(Rt)):
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黄色镰刀菌/液体培养(赤霉病)
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。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将测试板在24℃下进行培育并且在施用后3-4天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,表E中的以下化合物在20ppm下对黄色镰刀菌给出至少80%的控制:
E.01、E.02、E.03、E.04、E.05、E.0 6、E.07、E.09、E.10、E.12、E.13、E.14、E.15。
黄色镰刀菌/小麦/小穗预防性(赤霉病)
将小麦小穗栽培品种Monsun置于多孔板(24孔规格)中的琼脂上,并且用在水中稀释的配制的测试化合物喷雾。在施用后1天,用真菌的孢子悬浮液对小穗进行接种。在气候室中在72h半黑暗随后是12h光照/12h黑暗的光方案下,将接种的小穗在20℃和60%相对湿度下进行培育,并且在未处理的比较小穗上出现适当水平的病害损害时(施用后6-8天),作为与未处理的相比时的病害控制百分比来评估化合物的活性。
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,表E中的以下化合物在200ppm下对黄色镰刀菌给出至少80%的控制:
E.03、E.05、E.09、E.10、E.12、E.14、E.15。
玉米赤霉(禾谷镰刀菌)/小麦/小穗预防性(赤霉病)
将小麦小穗栽培品种Monsun置于多孔板(24孔规格)中的琼脂上,并且用在水中稀释的配制的测试化合物喷雾。施用后一天,将小穗用真菌的孢子悬浮液接种。在人工气候室中在72h半黑暗随后是的12h光照/12h黑暗的一个光方案下,在20℃和60%rh孵育接种的测试叶圆片,在未处理的对照小穗上出现适当水平的疾病损害时(施用后6-8天),作为与未处理的相比时的疾病控制百分比来评估化合物的活性。
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,表E中的以下化合物在200ppm下对玉米赤霉给出至少80%的控制:
E.06、E.09、E.10、E.14。
雪腐明梭孢(雪霉叶枯菌)/液体培养(谷物根腐病)
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。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将测试板在24℃下进行培育并且在施用后4-5天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,表E中的以下化合物在20ppm下对雪腐明梭孢给出至少80%的控制:
E.01、E.03、E.05、E.06、E.07、E.09、E.10、E.11、E.12、E.13、E.14、E.15。
禾生球腔菌(小麦壳针孢)/液体培养(叶枯病(Septoriablotch))
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。在将测试化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌孢子的营养肉汤。将测试板在24℃下进行培育并且在施用后4-5天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疾病发展的未处理的对照相比时,表E中的以下化合物在20ppm处对禾生球腔菌给出至少80%的控制:
E.02、E.03、E.05、E.06、E.07、E.10、E.11、E.14、E.15。
在小麦上的禾生球腔菌(小麦壳针孢)/预防性
在喷雾室中,用在水中稀释的配制的(可乳化的浓缩物)测试化合物喷雾2周龄的小麦植物栽培品种Riband。在施用后一天,通过在其上喷雾孢子悬浮液来对测试植物进行接种,并且然后将其在温室中保持在22℃/21℃(白天/夜晚)。当在未处理的检查植物上出现适当水平的病害时直接评估病害损害,并且与未处理的对照进行比较来计算效力(施用后16-19天)。
当与在相同条件下显示出广泛的疾病发展的未处理的对照相比时,表E中的以下化合物在60ppm处对禾生球腔菌给出至少80%的控制:
E.03、E.05、E.10、E.13、E.14、E.15。
Claims (15)
1.一种具有式(I)的化合物:
其中,
A是N或CR8;
R1是氟、氰基、氯或甲基;
R2是氢或氟;
R3是C1-C4烷基或C3-C5环烷基;
R4是C1-C4烷基或C3-C5环烷基;
R5是卤素、C1-C4烷基、C2-C4烯基、C2-C4炔基、C1-C4烷氧基、羟基、C1-C4卤代烷基、C1-C4卤代烷氧基、C2-C4卤代烯基、氰基、硝基、-N(R9c)2、氰基C1-C3烷基、C3-C5环烷基、-CR9a(=NOR9b);
R6是氢、羟基、卤素、C1-C4烷基、C1-C4卤代烷基、氰基;
R7是氢或甲基;
R8是氢或甲基;
R9a是氢、C1-C4烷基或C3-C5环烷基;R9b是C1-C4烷基或C3-C5环烷基;并且R9c独立地选自氢或C1-C4烷基,或与它们所连接的氮原子一起形成4-、5-或6-元饱和杂环;
或其盐、对映异构体、互变异构体和/或N-氧化物。
2.根据权利要求1所述的化合物,其中,A是CR8。
3.根据权利要求1或权利要求2所述的化合物,其中,R1是氟。
4.根据权利要求1至3中任一项所述的化合物,其中,R3和R4是甲基。
5.根据权利要求1至4中任一项所述的化合物,其中,R5是卤素、氰基、甲基、乙基、甲氧基、乙氧基、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、氰基甲基或环丙基。
6.根据权利要求1至5中任一项所述的化合物,其中,R5是卤素或氰基。
7.根据权利要求1至6中任一项所述的化合物,其中,R6是氢、卤素或C1-C4烷基。
8.根据权利要求1至7中任一项所述的化合物,其中,R7是氢。
9.根据权利要求1至8中任一项所述的化合物,其中,R8是氢。
10.根据权利要求1至9中任一项所述的化合物,其中,所述具有式(I)的化合物由式(IA)或式(IB)表示:
11.一种农用化学组合物,其包含杀真菌有效量的根据权利要求1至10中任一项所述的化合物。
12.根据权利要求11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。
13.一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10中任一项所述的化合物、或包含所述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。
14.根据权利要求13所述的方法,其中,所述植物病原性微生物是禾生球腔菌并且所述有用植物是谷物、特别是小麦。
15.根据权利要求1至10中任一项所述的化合物作为杀真菌剂的用途。
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