CN113382988A - 杀微生物2-酰基氨基-噻唑-4-甲酰胺衍生物 - Google Patents
杀微生物2-酰基氨基-噻唑-4-甲酰胺衍生物 Download PDFInfo
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- CN113382988A CN113382988A CN201980077628.2A CN201980077628A CN113382988A CN 113382988 A CN113382988 A CN 113382988A CN 201980077628 A CN201980077628 A CN 201980077628A CN 113382988 A CN113382988 A CN 113382988A
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- alkyl
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- methyl
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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,该化合物可用作杀有害生物剂,并且尤其可用作杀真菌剂。
Description
本发明涉及杀微生物的噻唑衍生物,例如作为活性成分,所述噻唑衍生物具有杀微生物活性、特别是杀真菌活性。本发明还涉及这些噻唑衍生物的制备,涉及包含所述噻唑衍生物中的至少一种的农用化学组合物,并且涉及所述噻唑衍生物或其组合物在农业或园艺中用于控制或防止植物、收获的粮食作物、种子或非生命材料被植物病原性微生物,优选是真菌侵染的用途。
WO 2010/012793和WO 2017/207362描述了噻唑衍生物作为杀有害生物剂。
根据本发明,提供了一种具有式(I)的化合物:
其中
Y是C-F、C-H或N;
R1是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6羟烷基、C1-C6烷氧基C1-C6烷基、C3-C6环烷基、C1-C6烷氧基C1-C3烷氧基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C4烷基、C1-C6烷氧基羰基氧基C1-C4烷基、C1-C6烷基羰基氧基C1-C4烷基、C2-C6烯氧基、C2-C6炔氧基、C1-C6烷基硫烷基、二(C1-C6烷基)氨基、苯基、苯基C1-C3烷基、苯基C1-C3烷氧基C1-C3烷基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环;
R2是氢、卤素、氰基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、或HC(O)NH-;
R3是C1-C8烷基,C1-C8卤代烷基,C1-C8烷氧基,C3-C8环烷基,C3-C8环烷基C1-C2烷基(其中所述环烷基任选地被1至3个由R4表示的基团取代),苯基,苯基C1-C2烷基,杂芳基,杂芳基C1-C2烷基,其中所述杂芳基是包含单独地选自氮、氧和硫的1、2、3或4个杂原子的5元或6元芳香族单环,杂环基,杂环基C1-C2烷基,其中所述杂环基是包含单独地选自氮、氧和硫的1、2或3个杂原子的4元、5元或6元非芳香族单环,或任选地包含单独地选自氮、氧和硫的1、2、3、4或5个杂原子的5元至10元非芳香族螺环碳双环或碳三环系统,并且其中所述螺环碳双环或碳三环系统各自任选地通过C1-C2亚烷基连接基键合至分子的剩余部分;
R4是卤素、C1-C4烷基、C1-C4烷氧基、或C1-C4卤代烷基;
X是N或C-H;
或其盐或N-氧化物。
其中具有式(I)的化合物不是2-(N-乙酰基-3-氟-苯胺基)-N-异丙基-5-甲基-噻唑-4-甲酰胺或2-(N-乙酰基-3-氟-苯胺基)-5-甲基-N-仲丁基-噻唑-4-甲酰胺。
出人意料地,为实际目的,已经发现了具有式(I)的新颖化合物有着非常有利水平的生物活性,用来保护植物对抗由真菌引起的疾病。
此外,已经发现,具有以下特征的新颖的具有式(I)的化合物当与它们相应的游离胺(其例如从WO 2017/207362中已知)比较时,可以示出改进的溶解度特性(特别是在非极性溶剂中),和/或光稳定性特性:其中R1是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6羟烷基、C1-C6烷氧基C1-C6烷基、C3-C6环烷基、C1-C6烷氧基C1-C3烷氧基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C4烷基、C1-C6烷氧基羰基氧基C1-C4烷基、C1-C6烷基羰基氧基C1-C4烷基、C2-C6烯氧基、C2-C6炔氧基、C1-C6烷基硫烷基、二(C1-C6烷基)氨基、苯基、苯基C1-C3烷基、苯基C1-C3烷氧基C1-C3烷基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环,特别是当R1是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6烷氧基C1-C6烷基、C3-C6环烷基、C1-C6烷氧基C1-C3烷氧基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C4烷基、C2-C6烯氧基、C2-C6炔氧基、C1-C6烷基硫烷基、苯基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环。
根据本发明的第二方面,提供了一种农用化学组合物,其包含杀真菌有效量的根据本发明的具有式(I)的化合物。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,提供了一种控制或防止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所述植物、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,所述用途可以包括或可以不包括通过手术或疗法来治疗人体或动物体的方法。
当取代基被表示为“被任选地取代”时,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,例如一个、两个或三个R4取代基。例如,被1、2或3个卤素取代的C1-C8烷基可以包括但不限于-CH2Cl、-CHCl2、-CCl3、-CH2F、-CHF2、-CF3、-CH2CF3或-CF2CH3基团。作为另一个实例,被1、2或3个卤素取代的C1-C6烷氧基可以包括但不限于CH2ClO-、CHCl2O-、CCl3O-、CH2FO-、CHF2O-、CF3O-、CF3CH2O-或CH3CF2O-基团。
如本文中所使用的,术语“氰基”是指-CN基团。
如本文中所使用的,术语“卤素”是指氟(氟代)、氯(氯代)、溴(溴代)或碘(碘代)。
如本文中所使用的,术语“C1-C8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,所述烃链基团不含不饱和度,具有从一至八个碳原子,并且其通过单键附接至分子的剩余部分。“C1-C6烷基”、“C1-C4烷基”和“C1-C3烷基”应相应地解释。C1-C8烷基的实例包括但不限于甲基、乙基、正丙基及其异构体,例如异丙基。“C1-C6亚烷基”基团是指C1-C6烷基的相应定义,不同之处在于此种基团是通过两个单键附接至分子的剩余部分。术语“C1-C2亚烷基”应被相应地解释。C1-C6亚烷基的实例包括但不限于-CH2-、-CH2CH2-和-(CH2)3-。
如本文中所使用的,术语“C1-C6羟烷基”是指被一个或多个羟基取代的如以上一般定义的C1-C8烷基基团。C1-C6羟烷基的实例包括但不限于1-羟乙基。
如本文中所使用的,术语“C1-C8卤代烷基”是指如以上一般定义的C1-C8烷基基团,所述基团被一个或多个相同的或不同的卤素原子取代。C1-C8卤代烷基的实例包括但不限于三氟甲基。
如本文中所使用的,术语“C1-C8烷氧基”是指具有式-ORa的基团,其中Ra是如以上一般定义的C1-C8烷基基团。术语“C1-C6烷氧基”、“C1-C4烷氧基”以及“C1-C3烷氧基”应相应地解释。C1-C8烷氧基的实例包括但不限于甲氧基、乙氧基、1-甲基乙氧基(异丙氧基)、和丙氧基。
如本文中所使用的,术语“C2-C6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,所述烃链基团含有至少一个可以是(E)-或(Z)-构型的双键,具有从二至六个碳原子,其通过单键附接至分子的剩余部分。术语“C2-C3烯基”应被相应地解释。C2-C6烯基的实例包括但不限于乙烯基(ethenyl)(乙烯基(vinyl))、丙-1-烯基、丙-2-烯基(烯丙基)和丁-1-烯基。
如本文中所使用的,术语“C2-C6烯基氧基”是指具有式-ORa的基团,其中Ra是如以上一般定义的C2-C6烯基基团。
如本文中所使用的,术语“C2-C6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,所述烃链基团包含至少一个三键,具有从二至六个碳原子,并且其通过单键附接至分子的剩余部分。术语“C2-C3炔基”应被相应地解释。C2-C6炔基的实例包括但不限于乙炔基、丙-1-炔基、丁-1-炔基。
如本文中所使用的,术语“C2-C6炔氧基”是指具有式-ORa的基团,其中Ra是如以上一般定义的C2-C6炔基基团。
如本文中所使用的,术语“C1-C6烷氧基C1-C6烷基”是指具有式RbORa-的基团,其中Rb是如以上一般定义的C1-C6烷基基团,并且Ra是如以上一般定义的C1-C6亚烷基基团。
如本文中所使用的,术语“C1-C6烷氧基C1-C3烷氧基”是指具有式RbORaO-的基团,其中Rb是如以上一般定义的C1-C6烷基基团,并且Ra是如以上一般定义的C1-C3烷基基团。
如本文中所使用的,术语“C1-C6烷氧基羰基”是指具有式RaOC(O)-的基团,其中Ra是如以上一般定义的C1-C6烷基基团。
如本文中所使用的,术语“C1-C6烷氧基羰基C1-C4烷基”是指具有式RaOC(O)Rb-的基团,其中Ra是如以上一般定义的C1-C6烷基基团,并且Rb是如以上一般定义的C1-C4亚烷基基团。
如本文中所使用的,术语“C1-C6烷氧基羰基氧基C1-C4烷基”是指具有式RaOCO2Rb-的基团,其中Ra是如以上一般定义的C1-C6烷基基团,并且Rb是如以上一般定义的C1-C4亚烷基基团。C1-C6烷氧基羰基氧基C1-C4烷基的实例包括但不限于1-甲氧基羰基氧基-乙基和1-甲氧基羰基氧基-甲基。
如本文中所使用的,术语“C1-C6烷基羰基氧基C1-C4烷基”是指具有式RaCO2Rb-的基团,其中Ra是如以上一般定义的C1-C6烷基基团,并且Rb是如以上一般定义的C1-C4亚烷基基团。C1-C6烷基羰基氧基C1-C4烷基的实例包括但不限于1-甲基羰基氧基-甲基。
如本文中所使用的,术语“C1-C6烷基硫烷基”是指具有式RaS-的基团,其中Ra是如以上一般定义的C1-C6烷基基团。
如本文中所使用的,术语“二(C1-C6烷基)氨基”是指具有式(Ra)(Rb)N-的基团,其中Ra和Rb各自单独地是如以上一般定义的C1-C6烷基基团。二(C1-C6烷基)氨基的实例包括但不限于二甲基氨基和二乙基氨基。
如本文中所使用的,术语“C3-C8环烷基”是指属于单环饱和环系统并包含3至8个碳原子的基团。术语“C3-C6环烷基”、“C3-C4环烷基”应相应地解释。C3-C6环烷基的实例包括但不限于环丙基、1-甲基环丙基、2-甲基环丙基、环丁基、1-甲基环丁基、1,1-二甲基环丁基、2-甲基环丁基、和2,2-二甲基环丁基。
如本文中所使用的,术语“C3-C8环烷基C1-C2烷基”是指通过如以上定义的C1-C2亚烷基连接基附接至分子的剩余部分的C3-C8环烷基环。
如本文中所使用的,术语“苯基C1-C3烷基”是指通过如以上定义的C1-C3亚烷基连接基附接至分子的剩余部分的苯环。
如本文中所使用的,术语“苯基C1-C3烷氧基C1-C3烷基”是指具有式RcRbORa-的基团,其中Ra和Rb各自独立地是如以上一般定义的C1-C3亚烷基基团,并且Rc是苯环。苯基C1-C3烷氧基C1-C3烷基的实例包括但不限于苄氧基甲基和1-苄氧基乙基。
如本文中所使用的,术语“杂芳基”是指包含单独地选自氮、氧和硫的1个、2个、3个或4个杂原子的5元或6元芳香族单环基团。杂芳基的实例包括但不限于呋喃基、吡咯基、噻吩基、吡唑基、咪唑基、噻唑基、异噻唑基、噁唑基、异噁唑基、三唑基、四唑基、吡嗪基、哒嗪基、嘧啶基或吡啶基。
如本文中所使用的,术语“杂芳基C1-C2烷基”是指通过如以上定义的C1-C2亚烷基连接基附接至分子的剩余部分的杂芳基环。
如本文中所使用的,术语“杂环基”是指包含1、2或3个杂原子的稳定的4元、5元或6元非芳香族单环,其中所述杂原子单独地选自氮、氧和硫。所述杂环基基团可以经碳原子或杂原子键合至分子的剩余部分。杂环基的实例包括但不限于吖丙啶基、氮杂环丁烷基、氧杂环丁烷基、硫杂环丁烷基、四氢呋喃基、吡咯烷基、吡唑烷基、咪唑烷基、哌啶基、哌嗪基、吗啉基、二氧戊环基、二硫杂环戊烷基和噻唑烷基。
如本文中所使用的,术语“杂环基C1-C2烷基”是指通过如以上所定义的C1-C2亚烷基连接基附接至分子的剩余部分的杂环基环。
如本文中所使用的,“螺环碳双环或碳三环”是非芳香族双环系统,其包含两个在一个碳原子上连接在一起的环,即共享一个碳原子。螺环碳双环或碳三环系统的实例包括但不限于螺[3.3]庚烷基、螺[3.4]辛烷基、螺[4.5]癸烷基、螺[环丁烷-1,2’-茚满基]、或螺[环戊烷-1,2’-四氢萘基]。
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光学异构形式(即对映体的形式或非对映体的形式)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形式。
在每种情况下,根据本发明的具有式(I)的化合物处于游离形式、氧化形式(如N-氧化物)或盐形式(例如农艺学上可用的盐形式)。
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在CRC Press,Boca Raton[博卡拉顿CRC出版社](1991)的名为“HeterocyclicN-oxides[杂环N-氧化物]”一书中描述了它们。
以下清单提供了关于具有式(I)的化合物的取代基R1、R2、R3、R4、X和Y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。
Y是C-F、C-H或N。在一个实施例中,Y是C-F。在另一个实施例中,Y是C-H。在另外的实施例中,Y是N。
R1是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6羟烷基、C1-C6烷氧基C1-C6烷基、C3-C6环烷基、C1-C6烷氧基C1-C3烷氧基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C4烷基、C1-C6烷氧基羰基氧基C1-C4烷基、C1-C6烷基羰基氧基C1-C4烷基、C2-C6烯氧基、C2-C6炔氧基、C1-C6烷基硫烷基、二(C1-C6烷基)氨基、苯基、苯基C1-C3烷基、苯基C1-C3烷氧基C1-C3烷基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环。
优选地,R1是氢、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4羟烷基、C1-C3烷氧基C1-C4烷基、C3-C6环烷基、C1-C4烷氧基C1-C3烷氧基、C1-C3烷氧基羰基、C1-C3烷氧基羰基C1-C4烷基、C1-C4烷氧基羰基氧基C1-C3烷基、C1-C4烷基羰基氧基C1-C3烷基、C3-C5炔氧基、C1-C4烷基硫烷基、二(C1-C4烷基)氨基、苯基、苯基C1-C3烷基、苯基C1-C3烷氧基C1-C3烷基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环。
更优选地,R1是氢、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3羟烷基、甲氧基C1-C4烷基、C3-C4环烷基、C1-C2烷氧基C1-C2烷氧基、C1-C3烷氧基羰基、甲氧基羰基C1-C3烷基、C1-C2烷氧基羰基氧基C1-C2烷基、C1-C2烷基羰基氧基C1-C2烷基、C3-C4炔氧基、C1-C3烷基硫烷基、二乙基氨基、苯基、苄基、苯氧基、苄氧基C1-C2烷基、或杂芳基,其中所述杂芳基是包含选自氧和硫的单个杂原子的5元或6元芳香族单环。
甚至更优选地,R1是氢、甲基、乙基、甲氧基、乙氧基、氟甲基、氯甲基、溴甲基、2,2,2-三氟乙基、1-羟乙基、甲氧基甲基、1-甲氧基乙基、1-乙氧基甲基、1-甲氧基-1-甲基乙基、环丙基、甲氧基乙氧基、乙氧基羰基、2-甲氧基-2-氧代-乙基、2-甲氧基-氧代-乙基、2-甲氧基-氧代-丙基、炔丙氧基、1-甲氧基羰基氧基-乙基、1-乙氧基羰基氧基-乙基、1-甲基羰基氧基-乙基、甲基羰基氧基甲基、甲基硫烷基、乙基硫烷基、异丙基硫烷基、二乙基氨基、苯基、苄基、苯氧基、苄氧基甲基、1-苄氧基乙基、2-呋喃基、或2-苯硫基(thiophenyl)。
仍更优选地,R1是氢、甲基、乙基、甲氧基、乙氧基、氟甲基、2,2,2-三氟乙基、1-羟乙基、1-乙氧基甲基、环丙基、甲氧基乙氧基、2-甲氧基-2-氧代-乙基、2-甲氧基-氧代-乙基、2-甲氧基-氧代-丙基、炔丙氧基、1-甲氧基羰基氧基-乙基、1-乙氧基羰基氧基-乙基、1-甲基羰基氧基-乙基、甲基羰基氧基甲基、异丙基硫烷基、二乙基氨基、苯基、苄基、苯氧基、苄氧基甲基、1-苄氧基乙基、2-呋喃基、或2-苯硫基。
在一组具体的实施例中,R1是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6烷氧基C1-C6烷基、C3-C6环烷基、C1-C6烷氧基C1-C3烷氧基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C4烷基、C2-C6烯氧基、C2-C6炔氧基、C1-C6烷基硫烷基、苯基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环。
优选地,R1是氢、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C3烷氧基C1-C4烷基、C3-C6环烷基、C1-C4烷氧基C1-C3烷氧基、C1-C3烷氧基羰基、C1-C3烷氧基羰基C1-C4烷基、C3-C5炔氧基、C1-C4烷基硫烷基、苯基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环。
更优选地,R1是氢、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、甲氧基C1-C4烷基、C3-C4环烷基、C1-C2烷氧基C1-C2烷氧基、C1-C3烷氧基羰基、甲氧基羰基C1-C3烷基、C3-C4炔氧基、C1-C3烷基硫烷基、苯基、苯氧基、或杂芳基,其中所述杂芳基是包含选自氧和硫的单个杂原子的5元或6元芳香族单环。
甚至更优选地,R1是氢、甲基、乙基、甲氧基、乙氧基、氟甲基、氯甲基、溴甲基、2,2,2-三氟乙基、甲氧基甲基、1-甲氧基乙基、1-甲氧基-1-甲基乙基、环丙基、甲氧基乙氧基、乙氧基羰基、2-甲氧基-2-氧代-乙基、2-甲氧基-氧代-乙基、2-甲氧基-氧代-丙基、炔丙氧基、甲基硫烷基、乙基硫烷基、异丙基硫烷基、苯基、苯氧基、2-呋喃基、或2-苯硫基。
仍更优选地,R1是氢、甲基、乙基、甲氧基、乙氧基、氟甲基、2,2,2-三氟乙基、环丙基、甲氧基乙氧基、2-甲氧基-2-氧代-乙基、2-甲氧基-氧代-乙基、2-甲氧基-氧代-丙基、炔丙氧基、异丙基硫烷基、苯基、苯氧基、2-呋喃基、或2-苯硫基。
R2是氢、卤素、氰基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、或HC(O)NH-。优选地,R2是氢、卤素、C1-C3烷基、C1-C3烷氧基、C1-C2卤代烷基、或HC(O)NH-,更优选卤素、C1-C2烷基、C1-C2烷氧基、或HC(O)NH-。甚至更优选地,R2是氯、溴、甲基、甲氧基、或HC(O)NH-。甚至更优选地,R2是甲基或HC(O)NH-,并且最优选甲基。
R3是C1-C8烷基,C1-C8卤代烷基,C1-C8烷氧基,C3-C8环烷基,C3-C8环烷基C1-C2烷基(其中所述环烷基任选地被1至3个由R4表示的基团取代),苯基,苯基C1-C2烷基,杂芳基,杂芳基C1-C2烷基,其中所述杂芳基是包含单独地选自氮、氧和硫的1、2、3或4个杂原子的5元或6元芳香族单环,杂环基,杂环基C1-C2烷基,其中所述杂环基是包含单独地选自氮、氧和硫的1、2或3个杂原子的4元、5元或6元非芳香族单环,或任选地包含单独地选自氮、氧和硫的1、2、3、4或5个杂原子的5元至10元非芳香族螺环碳双环或碳三环系统,并且其中所述螺环碳双环或碳三环系统各自任选地通过C1-C2亚烷基连接基键合至分子的剩余部分。
优选地,R3是C1-C6烷基,C1-C4卤代烷基,C1-C4烷氧基,C3-C6环烷基,C3-C6环烷基C1-C2烷基(其中所述环烷基任选地被1至3个由R4表示的基团取代),苯基,杂芳基,杂芳基C1-C2烷基,其中所述杂芳基是包含单独地选自氮、氧和硫的1、2或3个杂原子的5元或6元芳香族单环,杂环基,杂环基C1-C2烷基,其中所述杂环基是包含单独地选自氮、氧和硫的1、2或3个杂原子的4元、5元或6元非芳香族单环,或任选地包含单独地选自氮、氧和硫的1、2或3个杂原子的5元至12元非芳香族螺环碳双环或碳三环系统,并且其中所述螺环碳双环或碳三环系统各自任选地通过C1-C2亚烷基连接基键合至分子的剩余部分。
更优选地,R3是C1-C4烷基,C1-C3烷氧基,C3-C6环烷基,C3-C6环烷基C1-C2烷基(其中所述环烷基任选地被1至3个由R4表示的基团取代),苯基,杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1、2或3个杂原子的5元或6元芳香族单环,杂环基,其中所述杂环基是包含单独地选自氮、氧和硫的1、2或3个杂原子的4元、5元或6元非芳香族单环,或任选地包含选自氮、氧和硫的单个杂原子的5元至12元非芳香族螺环碳双环或碳三环系统。
甚至更优选地,R3是C3-C6环烷基,其中所述环烷基任选地被1或2个由R4表示的基团取代,或R3是6元至10元非芳香族螺环碳双环系统。
仍更优选地,R3是C3-C4环烷基,其中所述环烷基任选地被1或2个由R4表示的基团取代,或R3是6元至8元非芳香族螺环碳双环系统。
甚至仍更优选地,R3是环丁基、2,2-二甲基环丁基或螺[3.4]辛烷基,并且最优选环丁基、2,2-二甲基环丁基、或螺[3.4]辛烷-3-基。
R4是卤素、C1-C4烷基、C1-C4烷氧基、或C1-C4卤代烷基。优选地,R4是卤素、C1-C3烷基、C1-C3烷氧基、C1-C2卤代烷基,更优选卤素、C1-C3烷基、C1-C3烷氧基、或C1-C3卤代烷基。甚至更优选地,R4是C1-C3烷基,仍更优选甲基、乙基或异丙基,并且最优选地,R4是甲基。
X是N或C-H。在一个实施例中,X是N。在另一个实施例中,X是C-H。
在根据本发明的具有式(I)的化合物中,优选地:
R1是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6羟烷基、C1-C6烷氧基C1-C6烷基、C3-C6环烷基、C1-C6烷氧基C1-C3烷氧基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C4烷基、C1-C6烷氧基羰基氧基C1-C4烷基、C1-C6烷基羰基氧基C1-C4烷基、C2-C6烯氧基、C2-C6炔氧基、C1-C6烷基硫烷基、二(C1-C6烷基)氨基、苯基、苯基C1-C3烷基、苯基C1-C3烷氧基C1-C3烷基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环;
R2是甲基;
R3是C1-C8烷基,C1-C8卤代烷基,C1-C8烷氧基,C3-C8环烷基,C3-C8环烷基C1-C2烷基(其中所述环烷基任选地被1至3个由R4表示的基团取代),苯基,苯基C1-C2烷基,杂芳基,杂芳基C1-C2烷基,其中所述杂芳基是包含单独地选自氮、氧和硫的1、2、3或4个杂原子的5元或6元芳香族单环,杂环基,杂环基C1-C2烷基,其中所述杂环基是包含单独地选自氮、氧和硫的1、2或3个杂原子的4元、5元或6元非芳香族单环,或任选地包含单独地选自氮、氧和硫的1、2、3、4或5个杂原子的5元至10元非芳香族螺环碳双环或碳三环系统,并且其中所述螺环碳双环或碳三环系统各自任选地通过C1-C2亚烷基连接基键合至分子的剩余部分;
R4是卤素、C1-C4烷基、C1-C4烷氧基、或C1-C4卤代烷基;
X是C N;并且
Y是C-F。
更优选地,R1是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6羟烷基、C1-C6烷氧基C1-C6烷基、C3-C6环烷基、C1-C6烷氧基C1-C3烷氧基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C4烷基、C1-C6烷氧基羰基氧基C1-C4烷基、C1-C6烷基羰基氧基C1-C4烷基、C2-C6炔氧基、C1-C6烷基硫烷基、二(C1-C6烷基)氨基、苯基、苯基C1-C3烷基、苯基C1-C3烷氧基C1-C3烷基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环;
R2是甲基;
R3是C3-C8环烷基,其中所述环烷基任选地被1至3个由R4表示的基团取代,或R3是任选地包含单独地选自氮、氧和硫的1、2、3、4或5个杂原子的5元至10元非芳香族螺环碳双环系统,并且其中所述螺环碳双环或碳三环系统各自任选地通过C1-C2亚烷基连接基键合至分子的剩余部分;
X是N;并且
Y是C-F。
甚至更优选地,R1是氢、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3羟烷基、甲氧基C1-C4烷基、C3-C4环烷基、C1-C2烷氧基C1-C2烷氧基、C1-C3烷氧基羰基、甲氧基羰基C1-C3烷基、C1-C2烷氧基羰基氧基C1-C2烷基、C1-C2烷基羰基氧基C1-C2烷基、C3-C4炔氧基、C1-C3烷基硫烷基、二乙基氨基、苯基、苄基、苯氧基、苄氧基C1-C2烷基、或杂芳基,其中所述杂芳基是包含选自氧和硫的单个杂原子的5元或6元芳香族单环;
R2是甲基;
R3是环丁基、2,2-二甲基环丁基、或螺[3.4]辛烷-3-基;
X是N;并且
Y是C-F。
仍更优选地,R1是氢、甲基、乙基、甲氧基、乙氧基、氟甲基、氯甲基、溴甲基、2,2,2-三氟乙基、1-羟乙基、甲氧基甲基、1-甲氧基乙基、1-乙氧基甲基、1-甲氧基-1-甲基乙基、环丙基、甲氧基乙氧基、乙氧基羰基、2-甲氧基-2-氧代-乙基、2-甲氧基-氧代-乙基、2-甲氧基-氧代-丙基、炔丙氧基、1-甲氧基羰基氧基-乙基、1-乙氧基羰基氧基-乙基、1-甲基羰基氧基-乙基、甲基羰基氧基-甲基、甲基硫烷基、乙基硫烷基、异丙基硫烷基、二乙基氨基、苯基、苄基、苯氧基、苄氧基甲基、1-苄氧基乙基、2-呋喃基、或2-苯硫基;
R2是甲基;
R3是环丁基、2,2-二甲基环丁基、或螺[3.4]辛烷-3-基;
X是N;并且
Y是C-F。
在一组具体的实施例中,在根据本发明的具有式(I)的化合物中,优选地:
R1是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6烷氧基C1-C6烷基、C3-C6环烷基、C1-C6烷氧基C1-C3烷氧基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C4烷基、C2-C6烯氧基、C2-C6炔氧基、C1-C6烷基硫烷基、苯基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环;
R2是甲基;
R3是C1-C8烷基,C1-C8卤代烷基,C1-C8烷氧基,C3-C8环烷基,C3-C8环烷基C1-C2烷基(其中所述环烷基任选地被1至3个由R4表示的基团取代),苯基,苯基C1-C2烷基,杂芳基,杂芳基C1-C2烷基,其中所述杂芳基是包含单独地选自氮、氧和硫的1、2、3或4个杂原子的5元或6元芳香族单环,杂环基,杂环基C1-C2烷基,其中所述杂环基是包含单独地选自氮、氧和硫的1、2或3个杂原子的4元、5元或6元非芳香族单环,或任选地包含单独地选自氮、氧和硫的1、2、3、4或5个杂原子的5元至10元非芳香族螺环碳双环或碳三环系统,并且其中所述螺环碳双环或碳三环系统各自任选地通过C1-C2亚烷基连接基键合至分子的剩余部分;
R4是卤素、C1-C4烷基、C1-C4烷氧基、或C1-C4卤代烷基;
X是C N;并且
Y是C-F。
更优选地,R1是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6烷氧基C1-C6烷基、C3-C6环烷基、C1-C6烷氧基C1-C3烷氧基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C4烷基、C2-C6炔氧基、C1-C6烷基硫烷基、苯基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环;
R2是甲基;
R3是C3-C8环烷基,其中所述环烷基任选地被1至3个由R4表示的基团取代,或R3是任选地包含单独地选自氮、氧和硫的1、2、3、4或5个杂原子的5元至10元非芳香族螺环碳双环系统,并且其中所述螺环碳双环或碳三环系统各自任选地通过C1-C2亚烷基连接基键合至分子的剩余部分;
X是N;并且
Y是C-F。
甚至更优选地,R1氢、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、甲氧基C1-C4烷基、C3-C4环烷基、C1-C2烷氧基C1-C2烷氧基、C1-C3烷氧基羰基、甲氧基羰基C1-C3烷基、C3-C4炔氧基、C1-C3烷基硫烷基、苯基、苯氧基、杂芳基,其中所述杂芳基是包含选自氧和硫的单个杂原子的5元或6元芳香族单环;
R2是甲基;
R3是环丁基、2,2-二甲基环丁基、或螺[3.4]辛烷-3-基;
X是N;并且
Y是C-F。
仍更优选地,R1是氢、甲基、乙基、甲氧基、乙氧基、氟甲基、氯甲基、溴甲基、2,2,2-三氟乙基、甲氧基甲基、1-甲氧基乙基、1-甲氧基-1-甲基乙基、环丙基、甲氧基乙氧基、乙氧基羰基、2-甲氧基-2-氧代-乙基、2-甲氧基-氧代-乙基、2-甲氧基-氧代-丙基、炔丙氧基、甲基硫烷基、乙基硫烷基、异丙基硫烷基、苯基、苯氧基、2-呋喃基、或2-苯硫基;
R2是甲基;
R3是环丁基、2,2-二甲基环丁基、或螺[3.4]辛烷-3-基;
X是N;并且
Y是C-F。
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。
根据本发明的具有式(I)的化合物(其中R1、R2、R3、X和Y是如对于式(I)定义的)可以通过如下方式获得:通过热加热或在碱的帮助下,将具有式(II)的化合物(其中R2、R3、X和Y是如对于式(I)定义的)与具有式(III)的化合物(其中R1是如对于式(I)定义的,并且R12是卤素,优选地是氯)进行转化。这在下面的方案1中示出。
方案1
具有式(II)的化合物(其中R2、R3、X和Y是如对于式(I)定义的)可以通过如下方式获得:通过热加热或在碱的帮助下或在过渡金属催化的Buchwald-Hartwig胺化条件下,将具有式(IV)的化合物(其中X和Y是如对于式(I)定义的)与具有式(V)的化合物(其中R2和R3是如对于式(I)定义的,并且R13是卤素,优选地是溴)进行转化。这在下面的方案2中示出。
方案2
具有式(V)的化合物(其中R2和R3是如对于式(I)定义的,并且R13是卤素,优选地是溴)可以通过如下方式获得:通过中间体酰氯或直接用肽偶联剂,将具有式(VI)的化合物(其中R2是如对于式(I)定义的,并且R13是卤素,优选地是溴)和具有式(VII)的化合物(其中R3是如对于式(I)定义的)进行转化。这在下面的方案3中示出。
方案3
具有式(VI)的化合物(其中R2是如对于式(I)定义的,并且R13是卤素,优选地是溴)可以通过用碱转化具有式(VIII)的化合物(其中R2是如对于式(I)定义的,R13是卤素,优选地是溴,并且R14是C1-C6烷基)来获得。这在下面的方案4中示出。
方案4
可替代地,具有式(II)的化合物(其中R2、R3、X和Y是如对于式(I)定义的)可以通过如下方式获得:通过中间体酰氯或直接用肽偶联剂,将具有式(IX)的化合物(其中R2、X和Y是如对于式(I)定义的)与具有式(VII)的化合物(其中R3是如对于式(I)定义的)进行转化。这在下面的方案5中示出。
方案5
具有式(IX)的化合物(其中R2、X和Y是如对于式(I)定义的)可以通过用碱转化具有式(X)的化合物(其中R2、X和Y是如对于式(I)定义的,并且R14是C1-C6烷基)来获得。这在下面的方案6中示出。
方案6
具有式(X)的化合物(其中R2、X、和Y是如对于式(I)定义的,并且R14是C1-C6烷基)可以通过如下方式获得:通过热加热或在碱的帮助下或在过渡金属催化的Buchwald-Hartwig胺化条件下,将具有式(IV)的化合物(其中X和Y是如对于式(I)定义的)与具有式(VII)的化合物(其中R2是如对于式(I)定义的,R12是卤素,优选地是溴,并且R13是C1-C6烷基)进行转化。这在下面的方案7中示出。
方案7
可替代地,具有式(X)的化合物(其中R2、X和Y是如对于式(I)定义的,并且R14是C1-C6烷基)可以通过如下方式获得:在过渡金属催化的Buchwald-Hartwig胺化条件下,将具有式(XI)的化合物(其中X和Y是如对于式(I)定义的,并且R13是卤素,优选地是溴或碘)与具有式(XII)的化合物(其中R2是如对于式(I)定义的,并且R14是C1-C6烷基)进行转化。这在下面的方案8中示出。
方案8
可替代地,具有式(II)的化合物(其中R2、R3、X和Y是如对于式(I)定义的)可以通过如下方式获得:通过热加热或在碱的帮助下或在过渡金属催化的Buchwald-Hartwig胺化条件下,将具有式(XI)的化合物(其中X和Y是如对于式(I)定义的,并且R13是卤素,优选地是溴或碘)与具有式(XIII)的化合物(其中R2和R3是如对于式(I)定义的)进行转化。这在下面的方案9中示出。
方案9
可替代地,根据本发明的具有式(I)的化合物(其中R1、R2、R3、X和Y是如对于式(I)定义的)可以通过如下方式获得:通过热加热或在碱的帮助下或在过渡金属催化的Buchwald-Hartwig胺化条件下,将具有式(V)的化合物(其中R2和R3是如对于式(I)定义的,并且R13是卤素,优选地是溴)与具有式(XIV)的化合物(其中R1、X和Y是如对于式(I)定义的)进行转化。这在下面的方案10中示出。
方案10
具有式(XIV)的化合物(其中R1、X和Y是如对于式(I)定义的)可以通过如下方式获得:通过热加热或在碱的帮助下,将具有式(XV)的化合物(其中X和Y是如对于式(I)定义的)与具有式(III)的化合物(其中R1是如对于式(I)定义的,并且R12是卤素,优选地是氯)进行转化。这在下面的方案11中示出。
方案11
可替代地,具有式(I)的化合物(其中R1、R2、R3、X和Y是如对于式(I)定义的)可以通过如下方式获得:通过热加热或在碱的帮助下,将具有式(XVI)的化合物(其中R1、R2、X和Y是如对于式(I)定义的)与具有式(VII)的化合物(其中R3是如对于式(I)定义的)进行转化。这在下面的方案12中示出。
方案12
具有式(XVI)的化合物(其中R1、R2、X和Y是如对于式(I)定义的)可以通过如下方式获得:通过热加热或在碱的帮助下,将具有式(IX)的化合物(其中R2、X和Y是如对于式(I)定义的)与具有式(III)的化合物(其中R1是如对于式(I)定义的,并且R12是卤素,优选地是氯)进行转化。这在下面的方案13中示出。
方案13
可替代地,具有式(XVI)的化合物(其中R1、R2、X和Y是如对于式(I)定义的)可以通过如下方式获得:通过热加热或在碱的帮助下,将具有式(IX)的化合物(其中R2、X和Y是如对于式(I)定义的)与具有式(XVII)的化合物(其中R1是如对于式(I)定义的)进行转化。这在下面的方案14中示出。
方案14
出人意料地,为了实际的用途,现在已经发现了具有式(I)的新颖的化合物有着非常有利水平的生物活性,以保护植物免受真菌引起的疾病。
可以在农业部门和相关领域中使用具有式(I)的化合物,用作例如用于控制植物有害生物的活性成分,或者在用于控制腐败微生物或对人潜在有害的有机体的非生命材料上使用。所述新颖化合物的特色是在低施用率下具有优异的活性,植物耐受良好以及不危害环境。它们有非常有用的治疗的、预防的和系统性的特质并且可以用于保护无数栽培植株。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。
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防止易受微生物攻击的植物或植物繁殖材料和/或收获的粮食作物免受侵染的方法,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。如本文中所使用的,术语“杀真菌剂”意指控制、改变或防止真菌生长的化合物。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。控制或改变效果包括所有从自然发育的偏离,如杀死、阻滞等,并且防止包括在植物内或上面防止真菌感染的屏障或其他防御构造。
也可以将具有式(I)的化合物作为处理植物繁殖材料(如种子,例如果实、块茎、或谷物)、或植物插条(如大米)的拌种剂,用于保护对抗真菌感染或土壤里的植物病原性真菌。可以在种植之前将繁殖材料用包括具有式(I)的化合物的组合物处理,例如可以在播种之前敷裹种子。
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,从而将根据本发明的活性成分施用至谷粒(包衣)。还可以在种植所述繁殖材料时,将所述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这样的方法,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,所述领域是例如在工业材料(包括木材以及与木材有关的工业产品)的保护中、在食品存储中、在卫生管理中。
此外,本发明还可以用于保护非生命材料(例如木料、墙板和涂料)免受真菌攻击。
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的细菌和病毒可能是有效的。这些疾病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(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(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、小核菌属、壳针孢属(包括颖枯壳针孢(S.nodorum)、小麦壳针孢(S.tritici))、草莓白粉病菌(Sphaerotheca macularis)、棕丝单囊壳(Sphaerothecafusca)(黄瓜白粉病菌(Sphaerotheca fuliginea))、孢子丝菌属(Sporothorix)、颖枯壳多孢(Stagonospora nodorum)、匍柄霉属(Stemphylium)、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、木霉属(包括哈茨木霉)、拟康氏木霉、绿色木霉)、毛癣菌属、核瑚菌属、葡萄钩丝壳、条黑粉菌属(Urocystis)、黑粉菌属(Ustilago)、黑星菌属(包括苹果黑星菌(V.inaequalis))、轮枝孢属、以及黄单胞菌属。
在本发明的范围内,待保护的目标作物和/或有用植物通常包括多年生和一年生作物,例如浆果植物,如黑莓、蓝莓、蔓越莓、覆盆子和草莓;谷物,如大麦、玉蜀黍(玉米)、小米、燕麦、米、黑麦、高粱黑小麦和小麦;纤维植物,如棉花、亚麻、大麻、黄麻和剑麻;农作物,如糖和饲料甜菜、咖啡、啤酒花、芥末、油菜(卡诺拉)、罂粟、甘蔗、向日葵、茶和烟草;果树,如苹果、杏、鳄梨、香蕉、樱桃、柑橘、油桃、桃、梨和李子;草,如百慕达草、蓝草、弯草、蜈蚣草、羊茅、黑麦草、圣奥古斯丁草和动植物草;草药,如罗勒、琉璃苣、香葱、香菜、薰衣草、独活草、薄荷、牛至、荷兰芹、迷迭香、鼠尾草和百里香;豆类,如黄豆、扁豆、豌豆和大豆;坚果,如杏仁、腰果、落花生、榛子、花生、山核桃、开心果和核桃;棕榈植物,如油棕榈;观赏植物,如花、灌木和树;其他树木,例如可可、椰子、橄榄和橡胶;蔬菜,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、菠菜和番茄;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丁膦抗性玉米品种,它们在Herculex和商标名下是可商购的。
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,所述毒素如已知例如来自产毒素细菌,尤其是芽孢杆菌属的那些细菌。
此类植物的实例是:(玉米品种,表达CryIA(b)毒素);YieldGard(玉米品种,表达CryIIIB(b1)毒素);YieldGard(玉米品种,表达CryIA(b)和CryIIIB(b1)毒素);(玉米品种,表达Cry9(c)毒素);Herculex(玉米品种,表达CryIF(a2)毒素以及实现对除草剂草丁膦铵的耐受性的酶膦丝菌素N-乙酰转移酶(PAT));NuCOTN(棉花品种,表达CryIA(c)毒素);Bollgard(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(玉米根虫特性)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,所述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。
可通过此类转基因植物表达的毒素包括,例如来自于枯草芽孢杆菌或日本甲虫芽孢杆菌的杀虫蛋白质;或来自于苏云金芽孢杆菌的杀虫蛋白质,如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;或线虫共生细菌的杀虫蛋白质,例如光杆状菌属或致病杆菌属,如发光光杆状菌、嗜线虫致病杆菌;由动物产生的毒素,如蝎毒素、蜘蛛毒素、黄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;蛋白酶抑制剂,如胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯贮存蛋白(patatin)、半胱氨酸蛋白酶抑制剂、木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、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、蜕皮类固醇-UDP-糖基-转移酶、胆固醇氧化酶、蜕皮激素抑制剂、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、茋合酶、联苄合酶、几丁酶和葡聚糖酶。
在本发明的上下文中,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WO03/018810)。
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。这样的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。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以及Cry3Bb1毒素);(玉米品种,表达Cry9C毒素);Herculex(玉米品种,表达Cry1Fa2毒素以及实现对除草剂草丁膦铵的耐受性的酶膦丝菌素N-乙酰转移酶(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
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,已经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。该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(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/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的耐受性。
7.NK603×MON 810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/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×MON810玉米转基因地表达由土壤杆菌属物种菌株CP4获得的蛋白质CP4 EPSPS(使之耐除草剂(含有草甘膦)),以及还有由苏云金芽孢杆菌库尔斯塔克亚种(Bacillusthuringiensis subsp.kurstaki)获得的Cry1Ab毒素(使之耐某些鳞翅目昆虫,包括欧洲玉米螟)。
如本文中所使用的,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”应当理解为表示植物的生殖部分,如种子,所述部分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破土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。
在此提及的使用其俗名的杀有害生物剂是已知的,例如,从“The PesticideManual[杀有害生物剂手册]”,第15版,英国作物保护委员会(British Crop ProtectionCouncil)2009。
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、颗粒以及还有封装物,例如在聚合物的物质中。对于组合物的类型,根据预期的目的以及盛行环境来选择施用方法,如喷雾、雾化、撒粉、播散、包衣或倾倒。所述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,以及肥料、微量营养素供体或其他用于获得特殊效果的配制品。
合适的载体以及佐剂(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。这样的载体例如描述在WO 97/33890中。
具有式(I)的化合物通常以组合物的形式使用并且可同时地或与另外的化合物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、杀软体动物剂或几种这些制剂的混合物,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佐剂一起。
具有式(I)的化合物可以按用于控制或保护对抗植物病原性微生物的杀真菌组合物的形式使用,所述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以上所定义的个别化合物作为活性成分(处于游离形式或农用化学上可用的盐形式),以及至少一种上述佐剂。
本发明提供了如下组合物,优选杀真菌组合物,其包括至少一种具有式(I)的化合物、农业上可接受的载体以及可任选地佐剂。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,另外的活性成分会导致出人意料的协同活性。
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、酰肼杀真菌剂、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、苯基磺酰胺杀真菌剂、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实例还包括以下: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、cyclobutrifluram、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、二克磷、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、硝辛酯杀螨剂、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、flupentiofenox、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、唑呀威、三氯丙氧磷、三活菌素、蚜灭多、甲烯氟虫腈(vaniliprole)、百杀辛、二辛酸铜、硫酸铜、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、Steinernema riobravis、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、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-基磷酸醋、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、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、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、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、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、法呢醇与橙花叔醇、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(fenpropidine)、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-S)、地茂散(chloroneb)、百菌清、环氟菌胺、霜脲氰、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)、噁唑菌酮、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)、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)、lvbenmixianan、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、pyraziflumid、inpyrfluxam、trolprocarb、氯氟醚菌唑、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、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、florylpicoxamid、苯吡克咪徳(fenpicoxamid)、异丁乙氧喹啉、ipflufenoquin、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、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、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、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、amectotractin、异菌脲、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,其可以由WO 2017/055473、WO2017/055469、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]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WO2018/153707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WO2016/202742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)。
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,例如伊维菌素、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、帕苯达唑以及所述类别的其他成员。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噁唑啉(如在US-5478855、US-4639771和DE-19520936中所披露的)组合使用。
本发明的化合物可以与如WO-9615121中所述的一般种类二氧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(例如WO-9611945、WO-9319053、WO-9325543、EP-626375、EP-382173、WO-9419334、EP-382173、以及EP-503538中所述的那些)组合使用。
本发明的化合物可以与其他杀体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(如虱螨脲);蜕皮激素促效剂(如虫酰肼等);新烟碱(如吡虫啉等)。
本发明的化合物可与萜烯生物碱组合使用,例如在WO 95/19363或WO 04/72086中描述的那些,特别是其中公开的化合物。
可以与本发明的化合物组合使用的这样的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、α-氯氰菊酯(alphametrin)、5-苄基-3-呋喃基甲基(E)-
(1R)-顺式-2,2-二甲基-3-(2-氧硫杂环戊-3-亚基甲基)环丙烷羧酸酯、联苯菊酯、β-氟氯氰菊酯、氟氯氰菊酯、α-氯氰菊酯(α-cypermethrin)、β-氯氰菊酯、生物烯丙菊酯、生物烯丙菊酯((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、cythithrin、苯醚氰菊酯、溴氰菊酯、炔戊菊酯、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、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、氟佐隆、氟螨脲、氟虫脲、氟铃脲、虱螨脲、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、苏云金芽孢杆菌、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(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。
本发明的另一方面涉及具有式(I)的化合物的、或优选的如以上定义的单独的化合物的、包括至少一种具有式(I)的化合物或至少一种优选的如以上定义的单独的化合物的组合物的、或包括至少一种具有式(I)的化合物或至少一种优选的如以上定义的单独的化合物的如以上定义与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途,用于控制或防止植物(例如有用植物(例如作物))、它们的繁殖材料(例如种子)、收获的作物(例如收获的粮食作物)、或非生命材料免于被昆虫或植物病原性微生物(优选是真菌有机体)侵染。
本发明的另一方面涉及控制或防止植物(例如有用植物(例如作物))、它们的繁殖材料(例如种子)、收获的作物(例如收获的粮食作物)、或非生命材料免于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)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单独的化合物作为活性成分施用至所述植物、植物的各部分或至其底部、它们的繁殖材料、或非生命材料的任何部分。
控制或防止是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。
控制或防止作物被植物病原性微生物(尤其是真菌)或昆虫侵染的优选的方法是叶面施用,所述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一种液体配制品浸泡所述植物的底部或者通过将处于固体形式的化合物例如以颗粒的形式(土壤施用)施用到土壤而经由土壤通过根(内吸作用)渗透所述植物。在水稻作物中,可以将这样的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涂覆而施用到种子(包衣)上。
一种配制品,例如包含具有式(I)的化合物、以及(如果希望的话)固体或液体佐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,典型地通过将所述化合物与增充剂(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/或研磨来进行制备。
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,适宜的剂量是从10mg至1g活性物质/kg种子。
当本发明的组合用于处理种子时,比率为0.001g至50g具有式(I)的化合物/kg种子、优选从0.01g至10g/kg种子,这一般是足够的。
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性浓缩物(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)、分散性油悬剂(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佐剂组合的任何技术上可行的配制品的形式。
能以常规方式生产这样的组合物,例如通过混合活性成分与适当的配制惰性剂(稀释剂、溶剂、填充剂及任选地其他配制成分,例如表面活性剂、杀生物剂、防冻剂、黏着剂、增稠剂及提供辅佐效果的化合物)。还可以使用意欲长期持续药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,用自身已知的方式将拌种配制品施用至种子。这样的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,配制品包括按重量计从0.01%至90%的活性成分,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辅助剂,所述活性剂是由至少具有式(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或类似物)组成的。按重量计,组合物的浓缩形式通常含有在约2%与80%之间、优选在约5%与70%之间的活性剂。按重量计,配制品的施用形式可以例如含有从0.01%至20%、优选从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。
下表1展示了根据本发明的具有式(I)的单独的化合物。
表1:根据本发明的具有式(I)的单独的化合物
其中
a)具有式(I.a)的820种化合物:
其中R1、R2、X和Y是如在表1中定义的。
b)具有式(I.b)的820种化合物:
其中R1、R2、X和Y是如在表1中定义的。
c)具有式(I.c)的820种化合物:
其中R1、R2、X和Y是如在表1中定义的。
配制品实例
将活性成分与佐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。
将活性成分与佐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末。
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
将活性成分与佐剂混合并且研磨,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。
包衣颗粒剂
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。以该方式获得非尘的包衣颗粒剂。
悬浮液浓缩物
将精细地研磨的活性成分与佐剂紧密地混合,得到悬浮液浓缩物,从所述悬浮液浓缩液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
将精细地研磨的活性成分与佐剂紧密地混合,得到悬浮液浓缩物,从所述悬浮液浓缩液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)进行混合。将该混合物在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。向该乳液中添加在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。所述胶囊悬浮液配制品含有28%的活性成分。中等胶囊的直径是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。
实例
接下来的实例用来阐明本发明。本发明的化合物与已知的化合物的区别可以在于在低施用率下更大的疗效,这可以由本领域的普通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对抗由真菌引起的疾病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)、改进的物理-化学特性、或增加的生物可降解性)。
缩写清单
℃=摄氏度
CDCl3=氯仿-d
d=二重峰
Pd2(dba)3=三(二亚苄基丙酮)二钯(0)
DIPEA=N,N-二异丙基乙胺
DMF=二甲基甲酰胺
HATU=1-[双(二甲基氨基)亚甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓3-氧化六氟磷酸盐
m=多重峰
MHz=兆赫兹
mp=熔点
N=正常
ppm=百万分率
q=四重峰
s=单峰
t=三重峰
THF=四氢呋喃
Xantphos=4,5-双(二苯基膦基)-9,9-二甲基呫吨
实例1:本实例说明2-[乙酰基-(2,6-二氟-4-吡啶基)氨基]-N-(2,2-二甲基环丁基)-5-甲基-噻唑-4-甲酰胺(化合物I.b.596)的制备
a)2-[(2,6-二氟-4-吡啶基)氨基]-5-甲基-噻唑-4-甲酸甲酯的制备
在氩气氛下,将Xantphos(0.2当量)、Pd2(dba)3(0.1当量)以及碳酸铯(2当量)添加至经脱气的、经搅拌的2-溴-5-甲基-噻唑-4-甲酸甲酯(4.6g,18.5mmol,1当量)和2,6-二氟吡啶-4-胺(1当量)在1,4-二噁烷(660mL)中的混合物中。将反应加热至回流并且搅拌4h,然后使温度冷却至室温。将混合物用乙酸乙酯稀释并且经硅藻土过滤,并且使用旋转蒸发器将所得滤液浓缩。通过硅胶柱色谱法(洗脱液环己烷/乙酸乙酯混合物)纯化,得到希望的2-[(2,6-二氟-4-吡啶基)氨基]-5-甲基-噻唑-4-甲酸甲酯(1.8g,6.31mmol)。1H-NMR(400MHz,CDCl3):δ=2.73(s,3H),3.94(s,3H),6.75(s,1H)。
b)2-[(2,6-二氟-4-吡啶基)氨基]-5-甲基-噻唑-4-甲酸的制备
将一水氢氧化锂(4当量)添加至在四氢呋喃(35mL)和水(12mL)的混合物中的2-[(2,6-二氟-4-吡啶基)氨基]-5-甲基-噻唑-4-甲酸(1.8g,6.31mmol)的溶液中。将反应混合物在室温下搅拌16h,然后在真空中除去溶剂。将残余物用乙酸乙酯和水稀释,然后缓慢添加2N盐酸直至达到3-4的pH。通过过滤分离所形成的沉淀物,并且用水洗涤两次,得到希望的产物2-[(2,6-二氟-4-吡啶基)氨基]-5-甲基-噻唑-4-甲酸(1.55g,5.71mmol)。1H-NMR(400MHz,(CD3)2SO):δ=2.69(s,3H),7.30(s,2H),11.35(bs,1H),12.90(bs,1H)。
c)2-[(2,6-二氟-4-吡啶基)氨基]-N-(2,2-二甲基环丁基)-5-甲基-噻唑-4-甲酰胺的制备
将(2,2-二甲基环丁基)氯化铵(1.1当量)、HATU(1.1当量)和DIP{EA(2.6当量)按顺序添加至2-[(2,6-二氟-4-吡啶基)氨基]-5-甲基-噻唑-4-甲酸(250mg,0.92mmol,1当量)的DMF溶液(9.2mL)中。将所得溶液在室温下搅拌1h直至消耗起始材料(LCMS控制)。然后,将饱和NaHCO3溶液添加至混合物中并且将溶液用乙酸乙酯萃取三次。将有机相合并,经硫酸钠干燥,并且通过旋转蒸发器除去挥发物。通过硅胶柱色谱法(洗脱液:环己烷/乙酸乙酯的混合物)纯化,得到希望的产物2-[(2,6-二氟-4-吡啶基)氨基]-N-(2,2-二甲基环丁基)-5-甲基-噻唑-4-甲酰胺(280mg,86%产率)。1H-NMR(400MHz,CDCl3):d=1.17(s,3H),1.20(s,3H),1.50-1.75(m,2H),1.86-1.92(m,1H),2.29-2.36(m,1H),2.79(s,3H),4.25-4.31(m,1H),6.87(s,2H),7.32(d,1H),7.67(s,1H)。
d)2-[乙酰基-(2,6-二氟-4-吡啶基)氨基]-N-(2,2-二甲基环丁基)-5-甲基-噻唑-4-甲酰胺(化合物I.b.596)
将2-[(2,6-二氟-4-吡啶基)氨基]-N-(2,2-二甲基环丁基)-5-甲基-噻唑-4-甲酰胺(1.9g,5.4mmol)在乙酰氯(20ml)中的混合物在回流下搅拌3天。然后使反应冷却至室温并且通过旋转蒸发器除去挥发物。通过硅胶柱色谱法(洗脱液:环己烷/乙酸乙酯的混合物)纯化所得的粗材料,得到希望的产物2-[乙酰基-(2,6-二氟-4-吡啶基)氨基]-N-(2,2-二甲基环丁基)-5-甲基-噻唑-4-甲酰胺(1.57g,3.98mmol,74%产率)。1H-NMR(400MHz,CDCl3):d=0.92(s,3H),1.12(s,3H),1.48-1.75(m,3H),2.10-2.30(m,1H),2.17(s,3H),2.79(s,3H),4.25-4.31(m,1H),6.87(s,2H),7.32(d,1H)。
贯穿本说明书,以摄氏度(℃)给出温度并且“m.p.”是指熔点。LC/MS是指液相色谱质谱,并且所述装置的说明和方法是:
方法A:来自沃特斯公司(Waters)的ACQUITY UPLC,沃特斯UPLC HSS T3,1.8μm粒度,30×2.1mm柱,0.85mL/min.,60℃,H2O/MeOH 95:5+0.05%HCOOH(90%)/CH3CN+0.05%HCOOH(10%)–1.2min.–CH3CN+0.05%HCOOH(100%)–0.30min.,来自沃特斯公司的ACQUITY SQD质谱仪,电离法:电喷射(ESI),极性:正离子;毛细管电压(kV)3.00,锥孔电压(V)30.00,提取器(V)2.00,源温度(℃)150,去溶剂化温度(℃)350,锥孔反吹气流(L/Hr)0,去溶剂化气流(L/Hr)650)。
方法B:来自沃特斯公司的ACQUITY UPLC,沃特斯UPLC HSS T3,1.8μm粒度,30×2.1mm柱,0.85mL/min.,60℃,H2O/MeOH 95:5+0.05%HCOOH(90%)/CH3CN+0.05%HCOOH(10%)–2.7min.–CH3CN+0.05%HCOOH(100%)–0.30min.,来自沃特斯公司的ACQUITY SQD质谱仪,电离法:电喷射(ESI),极性:正离子,毛细管电压(kV)3.00,锥孔电压(V)30.00,提取器(V)2.00,源温度(℃)150,去溶剂化温度(℃)350,锥孔反吹气流量(L/Hr)0,去溶剂化气体流量(L/Hr)650))。
方法C:MS:来自沃特斯的ZQ质谱仪(单四极杆质谱仪)
仪器参数:离子化方法:电喷射极性:正(负)离子毛细管电压(kV)3.00,锥孔电压(V)30.00,提取器(V)2.00,气体温度(℃)350,干燥气体流量(mL/min)9.8,等离子体气压力(Neb press)45psig,质量范围:90至1000Da。
HPLC:来自安捷伦的HP 1100HPLC:溶剂脱气装置、四元泵(ZCQ)/二元泵(ZDQ)、加热管柱室以及二极管阵列检测器。柱:porpshell 120C18,2.7μm粒度,120埃,4.6×50mm,温度:30℃。DAD波长范围(nm):190至400溶剂梯度:A=水+0.1%HCOOH。B=乙腈+0.08%HCOOH。流动相:
方法D:如方法C的质谱仪。
HPLC:岛津LC-20A。柱:迪马公司(Dikma),DiamonsilC18(2)(5μm,150*4.6mm)。
流动相A:H2O(添加0.1%TFA);流动相B:ACN(添加0.1%TFA)。流量:1.0ml/min。
检测:UV@254nm。炉温:40℃。流动相:
时间(min) | A% | B% |
0 | 90 | 10 |
15 | 0 | 100 |
25 | 0 | 100 |
27 | 90 | 10 |
35 | 90 | 10 |
表2:表1中选定化合物的熔点和LC/MS数据(Rt=保留时间)。
出人意料地,已经发现具有式(I)的新颖化合物(即其中R1是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6烷氧基C1-C6烷基、C3-C6环烷基、C1-C6烷氧基C1-C3烷氧基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C4烷基、C2-C6烯氧基、C2-C6炔氧基、C1-C6烷基硫烷基、苯基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环),当相比于它们相应的游离胺(从WO 2017/207362中已知)时可以示出改进的溶解度(特别是在非极性溶剂中)和/或光稳定性特性。
贯穿下列描述,LogP意指分配系数的对数,ppm意指百万分率,并且T50表示化合物在照射条件下的半衰期。
下面呈现用于这些测量的方法。
分配系数
通过HPLC方法使用涂覆有辛醇的反相迷你柱测量辛醇-水分配系数(表示为LogP)。分配系数P与HPLC保留因子成正比。该方法的通用原理已经描述于例如J.Pharm.Sci.[药物科学杂志],67(1978)1364-1367中。
将沃特斯HPLC系统(model 1525二元泵;带有恒温器的2707自动进样器以及model2298光电二极管阵列检测器)与Hichrom迷你柱以及含有被调节至7的pH的、被1-辛醇(奥德里奇公司(Aldrich),HPLC级)饱和的20mM磷酸盐缓冲剂的水性流动相一起使用。所使用的迷你柱为HiRPB固定相,内径4.6mm乘以长4mm或内径2mm×长10mm。使用苯甲醚(奥德里奇公司,99%+纯度,LogP 2.11)作为校准系统的主要参比物。
光稳定性
光稳定性测试通过使用再现阳光的光谱和强度的过滤的氙灯系统(阿特拉斯(Atlas)Suntest)照射玻璃表面上的化合物和配制品的薄膜沉积物来进行。将Suntest的光谱输出功率设置为750W/m2,其是中午时典型的每日最大辐照度水平(英国,仲夏)。
典型地,将测试化合物溶解在HPLC级的甲醇中,以得到1g/L的储备溶液。可替代地,将配制的化合物以相同的浓度悬浮于水中。将2μL测试溶液的液滴点样到在3D打印的支架上的显微镜盖片上,使其干燥,然后在Suntest中照射不同的时间。然后将盖片从Suntest中移出并且放置在4打兰(dram)小瓶中;添加1mL洗涤溶剂(典型地30:70乙腈:0.2%水性甲酸),并且摇动小瓶以将化合物萃取至溶液中。通过反相HPLC,典型地使用带有光电二极管阵列(PDA)和沃特斯柱(BEH C18,100×2.1mm×1.7μm)的沃特斯UPLC系统,使用0.2%甲酸酸化的混合的水:乙腈流动相来分析溶液。在对于每种候选化合物的最佳波长下检测峰,并且PDA峰面积用于定量。使用损失%相对于时间的图来估计T50值,其是测试化合物最初损失50%所花费的时间。
可溶性
在缓冲剂水溶液(10mM混合磷酸盐,pH 7.20)中或在庚烷中制备测试化合物的饱和溶液。典型地,在最初处于超声浴中20分钟时间段后,使在2打兰(dram)小瓶中的带有1mL缓冲剂或庚烷的1mg测试化合物在筒式振动器(roller shaker)上过夜(20小时)。然后,将饱和样品通过Millex-HV 0.45微米注射器驱动的过滤器(取决于溶剂为水性型式或非水性型式)过滤。然后通过在LCMS上直接进样分析水性样品,并将使用PDA检测的峰面积与已知浓度的标准品进行比较;首先干燥庚烷样品并且将其重新溶解于LC相容溶剂中,该溶剂典型地为30:70乙腈:0.2%甲酸。方案的变化包括对预期具有极低溶解度的化合物的过滤器预饱和,以及对油的饱和样品的离心。
下表3说明了相对于WO 2017/207362的现有技术化合物的出人意料的物理化学特性(分配系数LogP,在庚烷中的溶解度和/或光稳定性)。
表3
生物学实例
实例B1:茄链格孢菌/番茄/叶圆片(早枯病)
将番茄叶圆片栽培品种Baby置于多孔板(24孔格式)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2天,用真菌的孢子悬浮液接种所述叶圆片。在气候室中在12/12h(照明/黑暗)的光方案下,在23℃/21℃(白天/夜晚)和80%rh下培育接种的叶圆片,并且化合物活性被评估为,在未处理的对照叶圆片上出现适当水平的疾病损害时(施用以后5-7天),与未处理的相比的疾病控制百分比。
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,以下化合物在200ppm处对茄链格孢菌给出至少80%的控制:I.b.595、I.b.596、I.b.600、I.b.603、I.b.604、I.b.606、I.b.607、I.b.608、I.b.612、I.b.613、I.b.617、I.b.815、I.b.816、I.b.817、I.b.818、I.c.812、I.c.813。
实例B2:灰葡萄孢菌(Botryotinia fuckeliana,Botrytis cinerea)/液体培养(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(沃格尔(Vogels)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。将所述测试板在24℃下进行孵育并且施用之后3-4天通过光度法测定对生长的抑制。
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,以下化合物在20ppm处对灰葡萄孢菌给出至少80%的控制:I.b.595、I.b.596、I.b.600、I.b.612、I.b.613、I.b.815、I.b.818。
实例B3:瓜小丛壳菌(Glomerella lagenarium)(瓜类炭疽菌(Colletotrichumlagenarium))/液体培养(炭疽病)
将来自低温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。将所述测试板在24℃下孵育并且施用3-4天以后通过光度法测量对生长的抑制。
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,以下化合物在20ppm处对瓜小丛壳菌给出至少80%的控制:I.b.595、I.b.596、I.b.600、I.b.603、I.b.604、I.b.606、I.b.607、I.b.608、I.b.612、I.b.613、I.b.815、I.b.816、I.b.817、I.b.818、I.b.820、I.c.600、I.c.811、I.c.812、I.c.813、I.c.814。
实例B4:小麦白粉病菌(Blumeria graminis f.sp.tritici,Erysiphe graminisf.sp.Tritici)/小麦/叶圆片预防性(小麦上的白粉病)
将小麦叶段栽培品种Kanzler置于多孔板(24孔规格)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,通过在所述测试板之上摇动白粉病感染的植物来接种叶圆片。在气候箱中,在24h黑暗、随后是12h光照/12h黑暗的光照方案下,在20℃和60%rh下孵育经接种的叶圆片,并且在未处理的对照叶段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疾病发展的未处理的对照相比时,以下化合物在200ppm下给出对小麦白粉病菌的至少80%的控制:I.a.596、I.a.600、I.a.601、I.a.812、I.b.595、I.b.596、I.b.598、I.b.599、I.b.600、I.b.603、I.b.604、I.b.606、I.b.607、I.b.608、I.b.610、I.b.612、I.b.613、I.b.614、I.b.615、I.b.616、I.b.617、I.b.618、I.b.815、I.b.816、I.b.817、I.b.818、I.b.820、I.c.596、I.c.600、I.c.811、I.c.812、I.c.813、I.c.814。
实例B5: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)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天之后,用真菌的孢子悬浮液接种所述小穗。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孵育接种的小穗,并且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天之后),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疾病发展的未处理的对照相比时,以下化合物在200ppm处对黄色镰刀菌给出至少80%的控制:I.b.600。
实例B6:玉米赤霉(黄色镰刀菌(Fusarium graminearum)/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)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疾病发展的未处理的对照相比时,以下化合物在200ppm处对玉米赤霉给出至少80%的控制:I.b.607。
实例B7:颖枯壳针孢(Phaeosphaeria nodorum,Septoria nodorum)/小麦/叶圆片预防性(颖斑枯病)
将小麦叶段栽培品种Kanzler置于多孔板(24孔规格)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2天,用真菌的孢子悬浮液接种所述叶圆片。在气候室中在12h照明/12h黑暗的光方案下,在20℃和75%rh下孵育接种的测试叶圆片,并且化合物活性被评估为,在未处理的对照叶圆片上出现适当水平的疾病损害时(施用后5-7天),与未处理的相比的疾病控制百分比。
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,以下化合物在200ppm处对颖枯壳针孢给出至少80%的控制:I.b.603、I.b.604、I.b.607、I.a.812。
实例B8:雪腐明梭孢(Monographella nivalis)(雪霉叶枯菌(Microdochiumnivale))/液体培养(谷类根腐病)
将来自低温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。将所述测试板在24℃下进行孵育并且施用之后4-5天通过光度法测定对生长的抑制。
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,以下化合物在20ppm处对雪腐明梭孢给出至少80%的控制:I.a.600、I.b.595、I.b.596、I.b.600、I.b.603、I.b.604、I.b.606、I.b.607、I.b.608、I.b.612、I.b.613、I.b.615、I.b.616、I.b.817、I.b.618、I.b.815、I.b.816、I.b.818、I.b.820、I.c.600、I.c.811、I.c.812、I.c.813、I.c.814。
实例B9:落花生球腔菌(落花生尾孢菌)/液体培养(早期叶斑病)
将来自低温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。将所述测试板在24℃下进行孵育并且施用之后4-5天通过光度法测定对生长的抑制。
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,以下化合物在20ppm处对落花生球腔菌给出至少80%的控制:I.b.595、I.b.600、I.b.603、I.b.604、I.b.606、I.b.607、I.b.612、I.b.816、I.c.812。
实例B10:豆薯层锈菌/大豆/预防性(大豆锈病)
将大豆叶圆片置于多孔板(24孔规格)中的水琼脂上,并且用在水中稀释的配制的测试化合物进行喷雾。施用后一天,通过在下部叶表面喷雾孢子悬浮液来接种叶圆片。在气候室中,在黑暗中在20℃和75%rh下的24-36小时的孵育期之后,用12h照明/天和75%rh将叶圆片保持在20℃。当在未处理的对照叶圆片中出现适当水平的疾病损害时(施用后12-14天),作为与未处理的相比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疾病发展的未处理的对照相比时,以下化合物在200ppm下给出对豆薯层锈菌的至少80%的控制:I.a.601、I.b.595、I.b.600、I.b.603、I.b.604、I.b.612、I.b.613、I.b.815、I.b.816、I.b.818。
实例B11:葡萄生单轴霉/葡萄/叶圆片预防性(晚疫病)
将葡萄藤叶圆片置于多孔板(24孔规格)中的水琼脂培养基上,并且用在水中稀释的配制的测试化合物喷雾。在施用之后1天,将所述叶圆片用真菌的孢子悬浮液进行接种。在气候箱中,在12h照明/12h黑暗的光方案下,在19℃和80%rh下孵育所述接种的叶圆片,并且化合物活性被评估为,在未处理的对照叶圆片中出现适当水平的疾病损害时(施用后6-8天),与未处理的相比的疾病控制百分比。
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,以下化合物在200ppm处对葡萄生单轴霉给出至少80%的控制:I.b.603、I.b.607。
实例B12:小麦隐匿柄锈菌(Puccinia recondita f.sp.tritici)/小麦/叶圆片治疗法(褐锈病)
将小麦叶段栽培品种Kanzler置于多孔板(24孔规格)内的琼脂上。用真菌的孢子悬浮液接种所述叶碎片。在19℃和75%rh下,在黑暗中储存板。在接种后1天,施用在水中稀释的配制的测试化合物。在气候室中,在12h光照/12h黑暗的光照方案下,在19℃和75%rh下孵育叶段,并且在未处理的对照叶段中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疾病发展的未处理的对照相比时,以下化合物在200ppm下给出对小麦隐匿柄锈菌的至少80%的控制:I.b.595、I.b.600、I.b.603、I.b.604、I.b.606、I.b.607、I.b.608、I.b.612、I.b.618、I.b.815、I.b.816、I.b.818。
实例B13:小麦隐匿柄锈菌/小麦/叶圆片预防性(褐锈病)
将小麦叶段栽培品种Kanzler置于多孔板(24孔规格)的琼脂上,并且用在水中稀释的配制的测试化合物喷雾。在施用之后1天,将所述叶圆片用真菌的孢子悬浮液进行接种。在气候室中,在12h光照/12h黑暗的光照方案下,在19℃和75%rh下孵育经接种的叶段,并且在未处理的对照叶段中出现适当水平的疾病损害时(施用后7-9天),作为与未处理的相比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疾病发展的未处理的对照相比时,以下化合物在200ppm下给出对小麦隐匿柄锈菌的至少80%的控制:I.a.596、I.a.600、I.a.601、I.a.812、I.b.595、I.b.596、I.b.600、I.b.603、I.b.604、I.b.606、I.b.607、I.b.608、I.b.612、I.b.613、I.b.614、I.b.618、I.b.815、I.b.816、I.b.817、I.b.818、I.c.600、I.c.811、I.c.812、I.c.813、I.c.814。
实例B14:稻瘟病菌(稻梨孢)/稻/叶圆片预防(稻瘟病)
将稻叶段栽培品种Ballila置于多孔板(24孔规格)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2天之后,用真菌的孢子悬浮液接种所述叶片段。在气候箱中,在24h黑暗,随后是12h光照/12h黑暗的光方案下,在22℃和80%rh(相对湿度)孵育所述接种的叶片段,并且在未处理的检验叶片段中出现适当的疾病损害水平时(施用后5-7天之后),作为与未处理的相比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疾病发展的未处理的对照相比时,以下化合物在200ppm处对稻瘟病菌给出至少80%的控制:I.a.596、I.a.600、I.a.601、I.a.812、I.b.595、I.b.596、I.b.598、I.b.600、I.b.603、I.b.604、I.b.606、I.b.607、I.b.608、I.b.612、I.b.613、I.b.614、I.b.615、I.b.616、I.b.617、I.b.618、I.b.815、I.b.816、I.b.817、I.b.818、I.b.820、I.c.596、I.c.596、I.c.600、I.c.811、I.c.812、I.c.813、I.c.814。
实例B15:圆核腔菌(Pyrenophora teres)/大麦/叶圆片预防性(网斑病)
将大麦叶段栽培品种Hasso置于多孔板(24孔格式)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2天之后用真菌的孢子悬浮液接种所述叶片段。在人工气候室中在12h光照/12h黑暗的一个光方案下,在20℃和65%rh孵育接种的叶片段,并且在未处理的对照叶片段上出现适当水平的疾病损害时(施用后5-7天之后),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疾病发展的未处理的对照相比时,以下化合物在200ppm处对圆核腔菌给出至少80%的控制:I.a.600、I.b.595、I.b.596、I.b.600、I.b.603、I.b.604、I.b.607、I.b.608、I.b.612、I.b.613、I.b.617、I.b.815、I.b.816、I.b.818、I.c.596、I.c.600、I.c.811、I.c.812、I.c.813。
实例B16:核盘菌/液体培养(棉状腐病)
将真菌的新生长的液体培养物的菌丝体片段直接混入营养肉汤(PDB(马铃薯葡萄糖肉汤))中。在将试验化合物的(DMSO)溶液置于微量滴定板(96孔规格)中之后,添加含有真菌材料的营养培养液。将所述测试板在24℃下进行孵育并且施用之后3-4天通过光度法测定对生长的抑制。
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,以下化合物在20ppm处对核盘菌给出至少80%的控制:I.b.607、I.b.612。
实例B17:禾生球腔菌(Mycosphaerella graminicola)(小麦壳针孢(Septoriatritici))/液体培养(叶枯病(Septoria blotch))
将来自低温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。将所述测试板在24℃下进行孵育并且施用之后4-5天通过光度法测定对生长的抑制。
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,以下化合物在20ppm处对禾生球腔菌给出至少80%的控制:I.b.595、I.b.596、I.b.600、I.b.603、I.b.604、I.b.606、I.b.607、I.b.612、I.b.815、I.b.816、I.b.817、I.b.818、I.c.811、I.c.812、I.c.813、I.c.814。
Claims (15)
1.一种具有式(I)的化合物:
其中,
Y是C-F、C-H或N;
R1是氢、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6羟烷基、C1-C6烷氧基C1-C6烷基、C3-C6环烷基、C1-C6烷氧基C1-C3烷氧基、C1-C6烷氧基羰基、C1-C6烷氧基羰基C1-C4烷基、C1-C6烷氧基羰基氧基C1-C4烷基、C1-C6烷基羰基氧基C1-C4烷基、C2-C6烯氧基、C2-C6炔氧基、C1-C6烷基硫烷基、二(C1-C6烷基)氨基、苯基、苯基C1-C3烷基、苯基C1-C3烷氧基C1-C3烷基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环;
R2是氢、卤素、氰基、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、或HC(O)NH-;
R3是C1-C8烷基,C1-C8卤代烷基,C1-C8烷氧基,C3-C8环烷基,C3-C8环烷基C1-C2烷基(其中所述环烷基任选地被1至3个由R4表示的基团取代),苯基,苯基C1-C2烷基,杂芳基,杂芳基C1-C2烷基,其中所述杂芳基是包含单独地选自氮、氧和硫的1、2、3或4个杂原子的5元或6元芳香族单环,杂环基,杂环基C1-C2烷基,其中所述杂环基是包含单独地选自氮、氧和硫的1、2或3个杂原子的4元、5元或6元非芳香族单环,或任选地包含单独地选自氮、氧和硫的1、2、3、4或5个杂原子的5元至10元非芳香族螺环碳双环或碳三环系统,并且其中所述螺环碳双环或碳三环系统各自任选地通过C1-C2亚烷基连接基键合至分子的剩余部分;
R4是卤素、C1-C4烷基、C1-C4烷氧基、或C1-C4卤代烷基;
X是N或C-H;
或其盐或N-氧化物。
2.根据权利要求1所述的化合物,其中,R1是氢、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基、C1-C4羟烷基、C1-C3烷氧基C1-C4烷基、C3-C6环烷基、C1-C4烷氧基C1-C3烷氧基、C1-C3烷氧基羰基、C1-C3烷氧基羰基C1-C4烷基、C1-C4烷氧基羰基氧基C1-C3烷基、C1-C4烷基羰基氧基C1-C3烷基、C3-C5炔氧基、C1-C4烷基硫烷基、二(C1-C4烷基)氨基、苯基、苯基C1-C3烷基、苯基C1-C3烷氧基C1-C3烷基、苯氧基、或杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1或2个杂原子的5元或6元芳香族单环。
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、C1-C3烷基、C1-C3烷氧基、C1-C3卤代烷基、C1-C3羟烷基、甲氧基C1-C4烷基、C3-C4环烷基、C1-C2烷氧基C1-C2烷氧基、C1-C3烷氧基羰基、甲氧基羰基C1-C3烷基、C1-C2烷氧基羰基氧基C1-C2烷基、C1-C2烷基羰基氧基C1-C2烷基、C3-C4炔氧基、C1-C3烷基硫烷基、二乙基氨基、苯基、苄基、苯氧基、苄氧基C1-C2烷基、或杂芳基,其中所述杂芳基是包含选自氧和硫的单个杂原子的5元或6元芳香族单环。
4.根据权利要求1至3中任一项所述的化合物,其中,R1是氢、甲基、乙基、甲氧基、乙氧基、氟甲基、氯甲基、溴甲基、2,2,2-三氟乙基、1-羟乙基、甲氧基甲基、1-甲氧基乙基、1-乙氧基甲基、1-甲氧基-1-甲基乙基、环丙基、甲氧基乙氧基、乙氧基羰基、2-甲氧基-2-氧代-乙基、2-甲氧基-氧代-乙基、2-甲氧基-氧代-丙基、炔丙氧基、1-甲氧基羰基氧基-乙基、1-乙氧基羰基氧基-乙基、1-甲基羰基氧基-乙基、甲基羰基氧基甲基、甲基硫烷基、乙基硫烷基、异丙基硫烷基、二乙基氨基、苯基、苄基、苯氧基、苄氧基甲基、1-苄氧基乙基、2-呋喃基、或2-苯硫基(thiophenyl)。
5.根据权利要求1至4中任一项所述的化合物,其中,R2是卤素、C1-C2烷基、C1-C2烷氧基或HC(O)NH-。
6.根据权利要求1至5中任一项所述的化合物,其中,R2是甲基。
7.根据权利要求1至6中任一项所述的化合物,其中,R3是C1-C4烷基,C1-C3烷氧基,C3-C6环烷基,C3-C6环烷基C1-C2烷基(其中所述环烷基任选地被1至3个由R4表示的基团取代),苯基,杂芳基,其中所述杂芳基是包含单独地选自氮、氧和硫的1、2或3个杂原子的5元或6元芳香族单环,杂环基,其中所述杂环基是包含单独地选自氮、氧和硫的1、2或3个杂原子的4元、5元或6元非芳香族单环,或任选地包含选自氮、氧和硫的单个杂原子的5元至12元非芳香族螺环碳双环或碳三环系统。
8.根据权利要求1至7中任一项所述的化合物,其中,R3是C3-C4环烷基,其中所述环烷基任选地被1或2个由R4表示的基团取代,或R3是6元至8元非芳香族螺环碳双环系统。
9.根据权利要求1至8中任一项所述的化合物,其中,X是N。
10.根据权利要求1至9中任一项所述的化合物,其中,Y是C-F。
11.根据权利要求1至10中任一项所述的化合物,其中,R3是环丁基、2,2-二甲基环丁基或螺[3.4]辛烷基。
12.一种农用化学组合物,所述农用化学组合物包含杀真菌有效量的根据权利要求1至11中任一项所述的具有式(I)的化合物。
13.根据权利要求12所述的组合物,所述组合物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。
14.一种控制或防止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中任一项所述的具有式(I)的化合物作为杀真菌剂的用途。
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