CN110023287B - 具有含硫取代基的杀有害生物活性杂环衍生物 - Google Patents
具有含硫取代基的杀有害生物活性杂环衍生物 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
具有式(I)的化合物,其中取代基是如在权利要求1中所定义的,以及那些化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N‑氧化物可以用作杀昆虫剂并且可按照本身已知的方式制备。
Description
本发明涉及包含硫取代基的杀有害生物活性(特别是杀昆虫活性)杂环衍生物,涉及其制备方法,涉及包含那些化合物的组合物,并且涉及它们用于控制动物有害生物(包括节肢动物并且特别是昆虫、或蜱螨目的代表)的用途。
具有杀有害生物作用的杂环化合物是已知的并描述于例如WO 2015/002211、WO2015/121136和WO 2016/124557中。现已发现具有含硫苯基和吡啶基取代基的新型杀有害生物活性杂环硫亚胺和亚砜亚胺衍生物。
本发明因此涉及具有式I的化合物,
其中
A是CH或N;
X是S、SO或SO2;
R1是C1-C4烷基、C1-C4卤代烷基或C3-C6环烷基-C1-C4烷基;
R7和R8彼此独立地是C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C1-C6氰基烷基、C1-C4烷氧基C1-C4烷基、吡啶基或苯基,其中所述吡啶基或苯基可以被选自由以下项组成的组的取代基单取代或多取代:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或者
R7和R8与它们所连的硫原子一起形成四至六元饱和环系,所述环系可以被选自由以下项组成的组的取代基单取代或多取代:卤素、氰基、C1-C4烷基、C1-C4烷氧基和C1-C4卤代烷基;并且所述环系可以包含一个选自由以下项组成的组的杂原子:氮、硫和氧;
n是0或1;
Q是选自由以下项组成的组的基团:式Q1至Q3
其中箭头表示与结合基团A的环的连接点;
并且其中
X1是O、S或NR3,其中R3是C1-C4烷基;
R2是卤素、C1-C6卤代烷基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基或C1-C6卤代烷氧基;
G1是N或CH;
G2和G3彼此独立地是N或CH;并且
所述具有式I的化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N-氧化物。
具有至少一个碱性中心的具有式I的化合物可以例如与以下酸形成例如酸加成盐,这些酸为:强无机酸(例如矿物酸,例如高氯酸、硫酸、硝酸、硝基酸(nitrose acid)、磷酸或氢卤酸),强有机羧酸(例如未经取代的或像被卤素取代的C1-C4烷羧酸,例如乙酸(像饱和或不饱和的二羧酸),例如草酸、丙二酸、琥珀酸、马来酸、富马酸或邻苯二甲酸(像羟基羧酸),例如抗坏血酸、乳酸、苹果酸、酒石酸或柠檬酸,或像苯甲酸),或有机磺酸(例如未经取代的或像被卤素取代的C1-C4烷磺酸或芳基磺酸,例如甲磺酸或对甲苯磺酸)。具有至少一个酸性基团的具有式I的化合物可以例如与碱形成盐,例如矿物盐,例如碱金属或碱土金属盐,例如钠盐、钾盐或镁盐;或与氨或有机胺形成盐,例如吗啉、哌啶、吡咯烷、单、二或三低碳数烷基胺,例如乙胺、二乙胺、三乙胺或二甲基丙基胺,或单、二或三羟基低碳数烷基胺,例如单乙醇胺、二乙醇胺或三乙醇胺。
在取代基定义中出现的烷基可以是直链的或支链的,并且是例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、戊基、己基、壬基、癸基以及它们的支链异构体。烷基硫烷基、烷基亚磺酰基、烷基磺酰基、烷氧基、烯基和炔基基团衍生自所提及的烷基基团。烯基和炔基可以是单不饱和的或多不饱和的。
卤素通常是氟、氯、溴或碘。相应地,这也适用于与其他含义结合的卤素,例如卤代烷基或卤代苯基。
卤代烷基优选地具有从1至6个碳原子的链长。卤代烷基是例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟乙基和2,2,2-三氯乙基;优选地是三氯甲基、二氟氯甲基、二氟甲基、三氟甲基和二氯氟甲基。
烷氧基优选地具有从1至6个碳原子的优选的链长。烷氧基是例如甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基和叔丁氧基并且还是同分异构的戊氧基和己氧基基团;优选地是甲氧基和乙氧基。
烷氧基烷基基团优选地具有1至6个碳原子的链长,更优选地1至4个碳原子的链长。烷氧基烷基是例如甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、正丙氧基甲基、正丙氧基乙基、异丙氧基甲基或异丙氧基乙基。
烷基硫烷基是例如甲基硫烷基、乙基硫烷基、丙基硫烷基、异丙基硫烷基、丁基硫烷基、戊基硫烷基、以及己基硫烷基。
烷基亚磺酰基是例如甲基亚磺酰基、乙基亚磺酰基、丙基亚磺酰基、异丙基亚磺酰基、丁基亚磺酰基、戊基亚磺酰基和己基亚磺酰基。
烷基磺酰基是例如甲基磺酰基、乙基磺酰基、丙基磺酰基、异丙基磺酰基、丁基磺酰基、戊基磺酰基和己基磺酰基。
环烷基优选地具有从3至6个环碳原子,例如环丙基、环丁基、环戊基和环己基。
卤代烷氧基基团优选具有从1至4个碳原子的链长。卤代烷氧基是例如二氟甲氧基、三氟甲氧基或2,2,2-三氟乙氧基。
卤代烷基硫烷基基团优选地具有从1至4个碳原子的链长。卤代烷基硫烷基是例如二氟甲基硫烷基、三氟甲基硫烷基或2,2,2-三氟乙基硫烷基。类似的考虑适用于基团C1-C4卤代烷基亚磺酰基和C1-C4卤代烷基磺酰基,它们可以是例如三氟甲基亚磺酰基、三氟甲基磺酰基或2,2,2-三氟乙基磺酰基。
在本发明的上下文中,取代基定义中的“单到多取代的”典型地是指,取决于取代基的化学结构,单取代的到四次取代的,优选是单取代的到三次取代的,更优选是单或二取代的。
自由基表示甲基。
根据本发明的具有式I的化合物还包括在盐形成期间可能形成的水合物。
优选地,R7和R8彼此独立地是C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、吡啶基或苯基,其中所述吡啶基或苯基可以被选自由以下项组成的组的取代基单取代或多取代:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4烷氧基、C1-C4卤代烷基硫烷基、C1-C4卤代烷基亚磺酰基、C1-C4卤代烷基磺酰基和-C(O)C1-C4卤代烷基;或者
R7和R8与它们所连的硫原子一起形成四至六元饱和环系,所述环系可以被选自由以下项组成的组的取代基单取代或多取代:卤素、氰基、C1-C4烷基和C1-C4卤代烷基;并且所述环系可以包含一个选自由以下项组成的组的杂原子:氮、硫和氧。
具有式I的化合物的优选的组由具有式I-1的化合物表示
其中Q、A、n、R7和R8是如上文在式I下所定义的;并且其中Xa1是S、SO或SO2;Ra1是甲基、乙基、正丙基、异丙基或环丙基甲基。
在具有式I-1的化合物的所述优选的组中,A优选地是N,Xa1优选地是S或SO2,更优选地是SO2,并且Ra1优选地是乙基。在具有式I-1的化合物的另一个优选的组中,A优选地是CH,Xa1优选地是S或SO2,更优选地是SO2,并且Ra1优选地是乙基。
在具有式I-1的化合物的另一个优选的组中,n是0或1,特别地n优选地是1,并且R7和R8彼此独立地是C1-C6烷基、C3-C6环烷基或被C1-C4烷基单取代的苯基,甚至更优选地是甲基、乙基、环丙基或被甲基取代的苯基(优选地在第4位);特别地R7和R8彼此独立地是C1-C6烷基或C3-C6环烷基,甚至更优选地是甲基或环丙基。
在具有式I-1的化合物的又另一个优选的组中,n是0或1,优选地n是1,并且R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系不含或含有一个氧原子。
具有式I-1的化合物的所述尤其优选的组的另一个优选的实施例包括以下化合物,其中A是N或CH,特别是A优选地是N;Xa1优选地是SO2;Ra1优选地是乙基;n是0或1,特别地n优选地是1;并且R7和R8彼此独立地是C1-C6烷基、C3-C6环烷基或被C1-C4烷基单取代的苯基,甚至更优选地是甲基、乙基、环丙基或被甲基取代的苯基(优选地在第4位);特别是C1-C6烷基或C3-C6环烷基,甚至更优选地是甲基或环丙基;或者R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系不含或含有一个氧原子。
在具有式I-1的化合物和上述具有式I-1的化合物的所有优选实施例中,Q优选地选自Q1至Q3,特别是选自Q1和Q2,其中X1、R2、G1、G2和G3是如上文在式I下所定义的。在具有式I-1的化合物的所述尤其优选的组中,X1优选地是NR3,其中R3是C1-C4烷基,更优选地是甲基;R2优选地是C1-C6卤代烷基,更优选地是三氟甲基;G1是CH或N,特别地G1是CH;G2是CH;并且G3是N。
具有式I的化合物的另一个优选的组由具有式I-2的化合物表示
其中X1、R2、G1、A、n、R7和R8是如上文在式I下所定义的;并且其中Xa2是S、SO或SO2;Ra2是甲基、乙基、正丙基、异丙基或环丙基甲基。
在具有式I-2的化合物的所述优选的组中,A是CH或N,特别地A优选地是N;Xa2优选地是S或SO2,更优选地是SO2;并且Ra2优选地是乙基。在具有式I-2的化合物的另一个优选的组中,X1优选地是NR3,其中R3是C1-C4烷基,更优选地是甲基;R2优选地是C1-C6卤代烷基,更优选地是三氟甲基;并且G1是CH或N,优选地是CH。
在具有式I-2的化合物和上述具有式I-2的化合物的所有优选实施例中,n是0或1,特别地n优选地是1;并且R7和R8是如上文在式I下所定义的。具有式I-2的化合物的所述尤其优选的组的另一个优选的实施例包括以下化合物,其中R7和R8彼此独立地是C1-C6烷基、C3-C6环烷基或被C1-C4烷基单取代的苯基,甚至更优选地是甲基、乙基、环丙基或被甲基取代的苯基(优选地在第4位);特别是C1-C6烷基或C3-C6环烷基,甚至更优选地是甲基或环丙基;或者R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系不含或含有一个氧原子。
具有式I的化合物的另一个优选的组由具有式I-3的化合物表示
其中
A是CH或N;特别地A是N;
R2是C1-C6卤代烷基,优选地三氟甲基;
G1是N或CH,优选地CH;
n是0或1;特别地n是1;
R7和R8彼此独立地是C1-C6烷基、C3-C6环烷基或被C1-C4烷基单取代的苯基,优选地是甲基、乙基、环丙基或被甲基取代的苯基(优选地在第4位);特别是C1-C6烷基或C3-C6环烷基,优选地是甲基或环丙基;或者
R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系可以含有一个氧原子。
具有式I的化合物的又另一个优选的组由具有式I-3a的化合物表示
其中
A是CH或N;
R2是C1-C6卤代烷基,优选地三氟甲基;
G1是N或CH;
n是0或1;
R7和R8彼此独立地是C1-C6烷基或C3-C6环烷基,优选地是甲基、乙基或环丙基;或者
R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系可以含有一个氧原子。
具有式I的化合物的又另一个优选的组由具有式I-3b的化合物表示
其中
A是CH或N;
R2是C1-C6卤代烷基,优选地三氟甲基;
n是0或1;
R7和R8彼此独立地是C1-C6烷基或C3-C6环烷基,优选地是甲基、乙基或环丙基;或者
R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系可以含有一个氧原子。
具有式I的化合物的又另一个优选的组由具有式I-3c的化合物表示
其中
A是CH或N;
R2是C1-C6卤代烷基,优选地三氟甲基;
n是1;
R7和R8彼此独立地是C1-C6烷基或C3-C6环烷基,优选地是甲基、乙基或环丙基;或者
R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系可以含有一个氧原子。
具有式I的化合物的另一个优选的组由具有式I-4的化合物表示
其中R2、G3、A、n、R7和R8是如上文在式I下所定义的;并且其中Xa3是S、SO或SO2;Ra3是甲基、乙基、正丙基、异丙基或环丙基甲基。
在具有式I-4的化合物的所述优选的组中,A是CH或N,特别地A优选地是N;Xa3优选地是S或SO2,更优选地是SO2;并且Ra3优选地是乙基。在具有式I-4的化合物的另一个优选的组中,R2优选地是C1-C6卤代烷基,更优选地是三氟甲基;并且G3是CH或N,优选地是N。
在具有式I-4的化合物和上述具有式I-4的化合物的所有优选实施例中,n是0或1,特别是优选地是1;并且R7和R8是如上文在式I下所定义的。具有式I-4的化合物的所述尤其优选的组的另一个优选的实施例包括以下化合物,其中R7和R8彼此独立地是C1-C6烷基、C3-C6环烷基或被C1-C4烷基单取代的苯基,甚至更优选地是甲基、乙基、环丙基或被甲基取代的苯基(优选地在第4位);特别是C1-C6烷基或C3-C6环烷基,甚至更优选地是甲基或环丙基;或者R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系不含或含有一个氧原子。
具有式I的化合物的另一个优选的组由具有式I-5的化合物表示
其中
A是CH或N;特别地A是N;
R2是C1-C6卤代烷基,优选地三氟甲基;
G3是N或CH,优选地是N;
n是0或1;特别地n是1;
R7和R8彼此独立地是C1-C6烷基、C3-C6环烷基或被C1-C4烷基单取代的苯基,优选地是甲基、乙基、环丙基或被甲基取代的苯基(优选地在第4位);特别是C1-C6烷基或C3-C6环烷基,优选地是甲基或环丙基;或者
R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系可以含有一个氧原子。
具有式I的化合物的又另一个优选的组由具有式I-5a的化合物表示
其中
A是CH或N;
R2是C1-C6卤代烷基,优选地三氟甲基;
n是1;
R7和R8彼此独立地是C1-C6烷基、C3-C6环烷基或被C1-C4烷基单取代的苯基,优选地是甲基、乙基、环丙基或被甲基取代的苯基(优选地在第4位);或者
R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系可以含有一个氧原子。
具有式I的化合物的另一个优选的组由具有式I-7的化合物表示
其中R2、G2、G3、A、n、R7和R8是如上文在式I下所定义的;并且其中Xa4是S、SO或SO2;Ra4是甲基、乙基、正丙基、异丙基或环丙基甲基。
在具有式I-7的化合物的所述优选的组中,A是CH或N,优选地是N;Xa4优选地是S或SO2,更优选地是SO2;并且Ra4优选地是乙基。在具有式I-7的化合物的另一个优选的组中,R2优选地是C1-C6卤代烷基,更优选地是三氟甲基;G2是CH;并且G3是CH或N,优选地是N。
在具有式I-7的化合物和上述具有式I-7的化合物的所有优选实施例中,n是0或1,优选地是1;并且R7和R8是如上文在式I下所定义的。具有式I-7的化合物的所述尤其优选的组的另一个优选的实施例包括以下化合物,其中R7和R8彼此独立地是C1-C6烷基、C3-C6环烷基或被C1-C4烷基单取代的苯基,甚至更优选地是甲基、乙基、环丙基或被甲基取代的苯基(优选地在第4位);或者R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系不含或含有一个氧原子。
具有式I的化合物的另一个优选的组由具有式I-8的化合物表示
其中
A是CH或N;
R2是C1-C6卤代烷基,优选地三氟甲基;
G2是CH;
G3是N或CH,优选地是N;
n是0或1;
R7和R8彼此独立地是C1-C6烷基、C3-C6环烷基或被C1-C4烷基单取代的苯基,优选地是甲基、乙基、环丙基或被甲基取代的苯基(优选地在第4位);或者
R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系不含或含有一个氧原子。
具有式I的化合物的又另一个优选的组由具有式I-8a的化合物表示
其中
A是N;
R2是C1-C6卤代烷基,优选地三氟甲基;
n是1;
R7和R8彼此独立地是C1-C6烷基或C3-C6环烷基,优选地是甲基、乙基或环丙基;或者
R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系可以含有一个氧原子。
具有式I的化合物的杰出的组由具有式I-6的化合物表示
其中
A是CH或N;特别地A是N;
n是0或1;特别地n是1;
R7和R8彼此独立地是C1-C6烷基、C3-C6环烷基或苯基,该苯基被C1-C4烷基单取代,优选地是甲基、乙基、环丙基或被甲基取代的苯基(优选地在第4位);特别是C1-C6烷基或C3-C6环烷基,优选地是甲基或环丙基;或者
R7和R8与它们所连的硫原子一起形成四至六元饱和环系,优选地所述环系是未取代的,并且所述环系可以含有一个氧原子;并且
Q是选自由以下项组成的组的基团:式Q1a、Q1b、Q2a和Q3a
特别是选自Q1a和Q2a;
其中箭头表示与结合基团A的环的连接点;
并且其中
R2是C1-C6卤代烷基,优选地是三氟甲基。
根据本发明的用于制备具有式I的化合物的方法原则上通过本领域的技术人员已知的方法进行。更具体地,具有式I的化合物的亚组(其中X是SO(亚砜)和/或SO2(砜))可以借助相应的具有式I的硫化物(其中X是S)的氧化反应获得,该反应涉及诸如间氯过氧苯甲酸(mCPBA)、过氧化氢、过硫酸氢钾(oxone)、高碘酸钠、次氯酸钠或次氯酸叔丁酯等氧化剂之类的试剂。该氧化反应通常在溶剂存在下进行。在该反应中使用的溶剂的实例包括脂族卤代烃,诸如二氯甲烷和氯仿;醇,诸如甲醇和乙醇;醋酸;水;及其混合物。用于该反应的氧化剂的量相对于1摩尔生成亚砜化合物I的硫化物I通常为1摩尔至3摩尔,优选1摩尔至1.2摩尔,并且相对于1摩尔生成砜化合物I的硫化物I优选地为2摩尔至2.2摩尔。此类氧化反应例如公开于WO 2013/018928中。
其中n是1的具有式I的化合物的亚组(限定具有式Ia的化合物,其中X、R1、R7、R8、A和Q如式I中所定义)
方案1:
可以通过以下方式制备:使具有式II的化合物(其中X、R1、A和Q如式I中所定义,并且其中Xa是离去基团,例如氯、溴或碘(优选溴),或芳基磺酸根、烷基磺酸根或卤代烷基磺酸根,例如三氟甲磺酸根)与具有式III的试剂HN=S(O)R7R8(其中R7和R8如式I中所定义)反应(方案1)。该反应可以通过钯基催化剂(包括例如双(二亚苄基-丙酮)钯(0)(Pd(dba)2)、三(二亚苄基丙酮)二钯(0)(Pd2(dba)3,任选以其氯仿加合物的形式)或乙酸钯(II))和配体(例如XantPhos((5-二苯基膦基-9,9-二甲基-氧杂蒽-4-基)二苯基膦)、RuPhos(2-二环己基膦基-2′,6′-二异丙氧基联苯)、JohnPhos([1,1'-联苯基]-2-基双(1,1-二甲基-乙基)膦)、BINAP(2,2'-双(二苯基膦基)-1,1'-联萘)、tol-BINAP([2,2'-双(二对甲苯基膦基)-1,1'-联萘])或三(邻甲苯基)膦在碱(如碳酸钠、碳酸钾或碳酸铯或者叔丁醇钠或叔丁醇钾)存在下在溶剂或溶剂混合物(例如二噁烷、1,2-二甲氧基乙烷或甲苯)中优选在惰性气氛下催化。反应温度可以优先地在从室温到反应混合物沸点的范围内,或者该反应可以在微波辐射下进行。此类反应已例如描述于Journal of Organic Chemistry[有机化学杂志],65(1),169-175;2000,Tetrahedron Letters[四面体通讯],39(32),5731-5734;1998,Chem.Commun.[化学通讯],47,7665-7667;2011或Tetrahedron[四面体],70(37),6613-6622;2014中。替代性地,该反应可以通过铁(例如氯化铁(III))在配体(诸如N,N'-二甲基-1,2-乙二胺)和碱(诸如碳酸钠、碳酸钾或碳酸铯)存在下在溶剂或溶剂混合物(例如二噁烷、1,2-二甲氧基乙烷或甲苯)中优选在惰性气氛下催化。反应温度可以优先地在从室温到反应混合物沸点的范围内,或者该反应可以在微波辐射下进行。此类反应已例如描述于Advanced Synthesis&Catalysis[高级合成与催化],350(3),391-394;2008中。作为进一步的替代性方案,该反应可以由铜(例如碘化铜(I)、乙酸铜(I)或氧化铜(I))任选地在配体(诸如N,N'-二甲基-1,2-乙二胺)和碱(诸如碳酸钠、碳酸钾或碳酸铯,或者磷酸钾)存在下在溶剂或溶剂混合物(例如二噁烷、1,2-二甲氧基乙烷、甲苯、N,N-二甲基甲酰胺或二甲亚砜)中优选在惰性气氛下催化。反应温度可以优先地在从室温到反应混合物沸点的范围内,或者该反应可以在微波辐射下进行。此类反应已例如描述于Advanced Synthesis&Catalysis[高级合成与催化],349(17+18),2673-2676;2007或Angewandte Chemie,International Edition[应用化学国际版],48,5691-5693;2009中。
其中R7和R8如式I中所定义的具有式III的化合物是已知的化合物、可商购获得或可通过在文献中描述的已知方法制备,例如在Journal of the Chemical Society[化学学会会刊],3004-5;1965或e-EROS Encyclopedia of Reagents for Organic Synthesis[有机合成试剂百科全书],1-8;2013中。有利的是从容易获得的具有式V的硫化物开始(参见Chem.Commun.[化学通讯]53,348-351;2017)或从相应的具有式VI的亚砜化合物开始(参见Angewandte Chemie,International Edition[应用化学国际版],55,7203-7207;2016)的用于具有式III的化合物的制备方法,其中R7和R8如式I中所定义,
这些方法涉及例如氨、氨基甲酸铵或乙酸铵作为合适的氮源,并且在诸如甲苯、乙腈或甲醇的溶剂中在0℃至100℃的温度下优选在大约室温下由高价碘试剂如二乙酰氧基碘苯介导。
其中X、R1、A和Q如式I中所定义并且其中Xa是离去基团的具有式II的化合物,特别是那些其中Xa是卤素的化合物,是已知的化合物,或者可以通过已知的方法制备,或者可以类似于文献中描述的方法合成。具体参见WO 2016/071214(Q是Q2)、WO 2016/026848(Q是Q1,G1是CH)、WO 2016/059145(Q是Q1,G1是N)和WO 2016/020286(Q是Q3)。更具体地,其中Q是Q1并且其中X、R1和A如式I中所定义并且其中Xa是离去基团的具有式II的化合物,特别是那些其中Xa是卤素(甚至更优选氯、溴或碘)的化合物由下面的具有式II-Q1的化合物(方案1a)表示,其中G1、X1和R2如上文在式I下所定义。其中G1是CH的具有式II-Q1的化合物的制备可以类似于WO 2015/000715和WO 2016/026848中的描述而实现;其中G1是N的具有式II-Q1的化合物的制备可以类似于WO 2016/059145中的描述而实现。
类似地,其中Q是Q2并且其中X、R1和A如式I中所定义并且其中Xa是离去基团的具有式II的化合物,特别是那些其中Xa是卤素(甚至更优选氯、溴或碘)的化合物由下面的具有式II-Q2的化合物(方案1a)表示,其中G3和R2如上文在式I下所定义。其中G3是N的具有式II-Q2的化合物的制备可以类似于WO 2016/071214中的描述而实现;其中G3是CH的具有式II-Q2的化合物的制备可以类似于WO 2015/000715中的描述而实现。
此外,其中Q是Q3并且其中X、R1和A如式I中所定义并且其中Xa是离去基团的具有式II的化合物,特别是那些其中Xa是卤素(甚至更优选氯、溴或碘)的化合物由下面的具有式II-Q3的化合物(方案1a)表示,其中G2、G3和R2如上文在式I下所定义。其中G2和G3是CH的具有式II-Q3的化合物的制备可以类似于WO 2013/191113中的描述而实现;其中G2是N并且G3是CH的具有式II-Q3的化合物的制备也可以类似于WO 2013/191113中的描述而实现;其中G2是CH并且G3是N的具有式II-Q3的化合物的制备可以类似于WO 2017/134066中的描述而实现;其中G2和G3是N的具有式II-Q3的化合物的制备可以类似于WO 2016/020286中的描述而实现。
方案1a:
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替代性地,具有式Ia的化合物(其中X、R1、R7、R8、A和Q如式I中所定义)
方案2a
可以通过从其中n是0的具有式I的化合物的亚组(限定具有式Ib的化合物,其中X、R1、R7、R8、A和Q如式I中所定义)的氧化步骤来制备(方案2a)。在此类转化中,可以使用经典氧化试剂诸如KMnO4、NaMnO4、mCPBA、NaIO4/RuO2、NaIO4/RuCl3、H2O2或过硫酸氢钾在例如在Journal of Organic Chemistry[有机化学杂志],44,2510;1979或Monatshefte fuerChemie[化学月刊]116(10),1153-64;1985中所述的条件下进行。特别地,在WO 2008/097235和WO 2008/106006中描述了钌盐与碱金属高碘酸盐的组合使用以及替代性地碱金属高锰酸盐的使用。用于氧化的合适溶剂是例如二氯甲烷、氯仿、甲醇、乙醇或乙酸。
具有式Ib的化合物(其中X、R1、R7、R8、A和Q如式I中所定义)可以通过具有式IV的化合物(其中X、R1、A和Q如式I中所定义)与具有式V的硫化物试剂SR7R8(其中R7和R8如式I中所定义)在亚胺化反应条件下反应而制备。同样地,具有式Ia的化合物(其中X、R1、R7、R8、A和Q如式I中所定义)可以通过具有式IV的化合物(其中X、R1、A和Q如式I中所定义)与具有式VI的亚砜试剂S(O)R7R8(其中R7和R8如式I中所定义)在类似的亚胺化反应条件下反应而制备。典型的制备方法和反应条件可以在例如H.Okamura,C.Bolm,Org.Lett.[有机化学通讯]2004,6,1305-1307;H.Okamura,C.Bolm,Chem.Lett.[化学通讯]2004,33,482-487;D.Leca,K.Song,M.Amatore,L.Fensterbank,E.M.Malacria,Chem.Eur.J.[欧洲化学杂志]2004,10,906-916或M.Reggelin,C.Zur,Synthesis[合成],2000,1-64中找到。特别感兴趣的是无金属的亚胺化方法,这些方法涉及具有式IV的化合物、具有式V或VI的试剂和氧化剂,例如G.Y.Cho,C.Bolm,Tetrahedron Lett.[四面体通讯]2005,46,8007-8008中所述的PhI(OAc)2(高价碘)或者C.Bolm等人,Synthesis[合成]2010,第17期,2922-2925中所述的N-溴代琥珀酰亚胺(NBS)和碱如叔丁醇钠或叔丁醇钾。替代性地,也可以使用诸如N-碘代琥珀酰亚胺(NIS)或碘的氧化剂,如例如在O.G.Mancheno,C.Bolm,Org.Lett.[有机通讯]2007,9,3809-3811中所述。在WO 2008/106006中描述了用作氧化剂的次氯酸盐的实例,例如次氯酸钠NaOCl或次氯酸钙Ca(OCl)2。
其中R7和R8如式I中所定义的具有式V的化合物和具有式VI的化合物是已知的化合物、可商购获得或可通过文献中描述的已知方法制备。
替代性地,具有式Ib的化合物(其中X、R1、R7、R8、A和Q如式I中所定义)
方案2b
可以通过以下方式制备(方案2b):使具有式IV的化合物(其中X、R1、A和Q如式I中所定义)与具有式VI的亚砜试剂S(O)R7R8(其中R7和R8如式I中所定义)反应,例如通过涉及五氧化二磷(Monatsh.Chem.[化学]101,396-404;1970)或三氟乙酸酐(J.Org.Chem.[有机化学杂志]40,2758-2764;1975)在三乙胺存在下,且在诸如氯仿或二氯甲烷的溶剂中,在-80℃至100℃,优选-70℃至60℃的温度下。
其中X、R1、A和Q如式I中所定义的具有式IV的化合物可以由具有式II的化合物以两步法制备,其中X、R1、A和Q如式I中所定义,并且其中Xa是离去基团,例如氯、溴或碘,或芳基磺酸根、烷基磺酸根或卤代烷基磺酸根,例如三氟甲磺酸根(方案3)。
方案3:
这种转化涉及:(i)使具有式II的化合物(其中离去基团Xa优选地是氯或溴)与例如氨基甲酸叔丁酯、氨基甲酸苄酯(其中苯基可以任选地被一个或两个甲氧基取代)、二苯甲酮亚胺或苯基甲亚胺在Buchwald-Hartwig型交叉偶联条件下反应,生成具有式VII的化合物,其中X、R1、A和Q如式I中所定义,并且其中Xb是-NHC(O)Ot-Bu、-NHC(O)OCH2Ph(其中苯基可以任选地被一个或两个甲氧基取代)、-N=C(Ph)2或-N=CH(Ph);然后(ii)将具有式VII的中间体化合物水解成具有式IV的化合物。这种过程(i)可以通过钯基催化剂(包括例如双(二亚苄基丙酮)钯(0)(Pd(dba)2)、三(二亚苄基丙酮)二钯(0)(Pd2(dba)3,任选以其氯仿加合物的形式)或乙酸钯(II))和配体(例如XPhos(2-二环己基膦基-2′,4′,6′-三异丙基-联苯)、XantPhos((5-二苯基膦基-9,9-二甲基-氧杂蒽-4-基)二苯基膦)、RuPhos(2-二环己基膦基-2′,6′-二异丙氧基联苯)、JohnPhos([1,1'-联苯基]-2-基双(1,1-二甲基-乙基)膦)、BINAP(2,2'-双(二苯基膦基)-1,1'-联萘)、tol-BINAP([2,2'-双(二对甲苯基膦基)-1,1'-联萘])或三(邻甲苯基)膦,在碱(如碳酸钠、碳酸钾或碳酸铯或者叔丁醇钠或叔丁醇钾)存在下,在溶剂或溶剂混合物(例如二噁烷、1,2-二甲氧基乙烷或甲苯)中,优选在惰性气氛下,在优先地从室温到反应混合物沸点范围内的反应温度下催化,或者该反应可在微波辐射下进行。替代性地,这种过程(i)可以通过铜基催化剂(包括例如碘化铜(I)(Cul)或三氟甲磺酸铜(II)),任选地在配体(诸如2,2'-联吡啶、脯氨酸、N,N'-二甲基甘氨酸或乙二醇)存在下,在合适的碱(诸如三乙胺、碳酸钠、碳酸钾、碳酸铯、甲醇钠、叔丁醇钠、叔丁醇钾)存在下,在合适的溶剂(诸如1,4-二噁烷、N,N-二甲基甲酰胺、二甲基亚砜或N-甲基吡咯烷酮)中在100℃至180℃的温度下催化,或者该反应可在微波辐射下进行。水解(ii)通常可在本领域技术人员已知的酸性或碱性含水条件下进行。典型地,将具有式VII的化合物用氯化氢水溶液或三氟乙酸,任选地在溶剂(诸如1,4-二噁烷、四氢呋喃或二氯甲烷)存在下,在优先地从0℃至反应混合物沸点范围内的反应温度下处理,或者该反应可在微波辐射下进行。
替代性地,这种II至IV的转化涉及:(iii)使具有式II的化合物(其中离去基团Xa优选地是氯或溴)与例如叠氮化钠或叠氮基三甲基硅烷在叠氮化条件下反应,生成具有式VIII的化合物,其中X、R1、A和Q如式I中所定义;然后(iv)将具有式VIII的中间体化合物还原成具有式IV的化合物。这种过程(iii)可以在溶剂(诸如N,N-二甲基甲酰胺或二甲基亚砜)中,任选地在铜催化剂(诸如碘化铜)存在下,任选地在配体(诸如脯氨酸或N,N′-二甲基乙二胺)的进一步存在下在50℃至150℃的温度下进行。还原(iv)可以在本领域技术人员已知的条件下(参见例如:R.C.Larock,Synthetic Organic Methodology:ComprehensiveOrganic Transformations.[有机合成方法:综合有机转化]A Guide to FunctionalGroup Preparations[官能团制备指南],1989;第409页)在与这些条件相容的各种有机或含水溶剂中,在低于0℃直至溶剂体系沸点的温度下进行。替代性地,经由VIII从II至IV的顺序可以在一个步骤中进行,由此中间体叠氮化物VIII在铜催化剂条件下原位还原,如例如在Journal of Organic Chemistry[有机化学杂志](2010),75(14),4887-4890及其中引用的参考文献中所述。经由VIII进行的这种从II至IV的一锅法也描述于例如WO 2016/091731中。
替代性地,其中Q是Q1的具有式I的化合物(限定具有式I-Q1的化合物,其中X、R1、n、R7、R8、A、X1、G1和R2如式I中所定义)
方案4:
可以通过使具有式(X)的化合物环化而制备(方案4),其中X、R1、n、R7、R8、A、X1、G1和R2如式I中所定义,例如通过在乙酸或三氟乙酸(优选地当X1是NR3时,其中R3是C1-C4烷基)中,在0℃至180℃,优选20℃至150℃的温度下,任选地在微波辐射下加热。具有式(X)的化合物的环化也可以在酸催化剂(例如甲磺酸或对甲苯磺酸p-TsOH)存在下,在惰性溶剂(诸如N-甲基吡咯烷酮或二甲苯)中,在25℃至180℃,优选100℃-170℃的温度下实现。此类方法先前已在例如WO 2010/125985中描述。替代性地,可以使用三苯基膦、偶氮二甲酸二异丙酯(或偶氮二甲酸二乙酯)在惰性溶剂(诸如四氢呋喃THF)中,在20℃-50℃的温度下将具有式(X)的化合物转化为具有式I-Q1的化合物(优选地当X1是O时)。先前已针对这些转化描述了此类光延反应(Mitsunobu)条件(参见WO2009/131237)。
具有式(X)的化合物(其中X、R1、n、R7、R8、A、X1、G1和R2如式I中所定义)可以通过以下方式制备:
i)通过本领域技术人员已知的并描述于例如Tetrahedron[四面体],2005,61(46),10827-10852中的方法使具有式(XIII)的化合物活化,其中X、R1、n、R7、R8和A如式I中所定义,以形成活化物质(XII),其中X、R1、n、R7、R8和A如式I中所定义,并且其中X00是卤素,优选氯。例如,通过在催化量的N,N-二甲基甲酰胺DMF存在下,在惰性溶剂(诸如二氯甲烷CH2Cl2或四氢呋喃THF)中,在20℃至100℃,优选25℃的温度下,用例如草酰氯(COCl)2或亚硫酰氯SOCl2处理(XIII)来形成化合物(XII)(其中X00是卤素,优选地是氯)。替代性地,在惰性溶剂(诸如吡啶或四氢呋喃THF)中,任选地在碱(诸如三乙胺)存在下,在50℃-180℃的温度下,用例如1-乙基-3-(3-二甲氨基丙基)碳二亚胺EDC或二环己基碳二亚胺DCC处理具有式(XIII)的化合物,将产生活化物质(XII)(其中X00分别是X01或X02);随后
ii)将活化物质(XII)用具有式XI的化合物(其中X1、G1和R2如式I中所定义),在碱(诸如三乙胺、N,N-二异丙基乙胺或吡啶)存在下,在惰性溶剂(诸如二氯甲烷、四氢呋喃、二噁烷、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、乙腈、乙酸乙酯或甲苯)中,在0℃至50℃的温度下处理,以形成具有式(X)的化合物。其中X1、G1和R2如式I中所定义的具有式(XI)的化合物先前已在例如WO 2012/086848、WO 2015/000715和WO 2016/116338中进行了描述。
具有式(XIII)的化合物(其中X、R1、n、R7、R8和A如式I中所定义)
方案5:
可以通过以下方式制备(方案5):使具有式(XIVa)的化合物或具有式(XIVb)的化合物(其中X、R1、R7、R8和A如式I中所定义,并且其中R00是C1-C6烷基)在本领域技术人员已知的条件(使用例如如下的条件:在室温或直至回流条件下,氢氧化钠、氢氧化钾或氢氧化锂在甲醇、乙醇或二噁烷中的水溶液)下皂化。
具有式(XIVa)的化合物(其中X、R1、R7、R8和A如式I中所定义,并且其中R00是C1-C6烷基)可以通过以下方式制备:使具有式(XV)的化合物(其中X、R1和A如式I中所定义,并且其中R00是C1-C6烷基,并且其中Xa是离去基团,例如氯、溴或碘(优选氯或溴),或芳基磺酸根、烷基磺酸根或卤代烷基磺酸根,例如三氟甲磺酸根)与具有式III的试剂HN=S(O)R7R8(其中R7和R8如式I中所定义)在上文已描述的条件下(参见方案1,化合物II转化为Ia)反应。
具有式(XIVa)的化合物(其中X、R1、R7、R8和A如式I中所定义,并且其中R00是C1-C6烷基)也可以通过以下方式制备:使具有式(XIVb)的化合物(其中X、R1、R7、R8和A如式I中所定义,并且其中R00是C1-C6烷基)在上文已描述的条件下(参见方案2a,化合物Ib转化为Ia)氧化。替代性地,具有式(XIVa)的化合物(其中X、R1、R7、R8和A如式I中所定义,并且其中R00是C1-C6烷基)也可以由具有式(XVI)的化合物(其中X、R1和A如式I中所定义,并且其中R00是C1-C6烷基)在上文已描述的条件下(参见方案2a,化合物IV转化为Ia)制备。
具有式(XIVb)的化合物(其中X、R1、R7、R8和A如式I中所定义,并且其中R00是C1-C6烷基)可以通过以下方式制备:使具有式(XVI)的化合物(其中X、R1和A如式I中所定义,并且其中R00是C1-C6烷基)与具有式VI的试剂S(O)R7R8(其中R7和R8如式I中所定义)在上文已描述的条件下(参见方案2b,化合物IV转化为Ib)反应。替代性地,具有式(XIVb)的化合物(其中X、R1、R7、R8和A如式I中所定义,并且其中R00是C1-C6烷基)可以通过以下方式制备:使具有式(XVI)的化合物(其中X、R1和A如式I中所定义,并且其中R00是C1-C6烷基)与具有式V的试剂SR7R8(其中R7和R8如式I中所定义)在上文已描述的条件下(参见方案2a,化合物IV转化为Ib)反应。
具有式(XVI)的化合物(其中X、R1和A如式I中所定义,并且其中R00是C1-C6烷基)可以由具有式(XV)的化合物(其中X、R1和A如式I中所定义,并且其中R00是C1-C6烷基,并且其中Xa是离去基团,例如氯、溴或碘(优选氯或溴),或芳基磺酸根、烷基磺酸根或卤代烷基磺酸根,例如三氟甲磺酸根)在上文已描述的条件下(参见方案3,化合物II转化为IV)制备。
具有式(XV)的化合物(其中X、R1和A如式I中所定义,并且其中R00是C1-C6烷基,并且其中Xa是离去基团,例如氯、溴或碘,或芳基磺酸根、烷基磺酸根或卤代烷基磺酸根,例如三氟甲磺酸根),特别是其中Xa是卤素(甚至更优选地氯、溴或碘)的那些化合物是已知的化合物、可商购获得或可通过在文献中描述的已知方法制备,如例如在WO 2016/005263、WO2016/023954、WO 2016/026848和WO 2016/104746中。
其中X、R1、n、R7、R8和A如式I中所定义,并且其中X1是NR3,其中R3是C1-C4烷基,甚至更具体地,其中X1是NCH3,并且其中G1是CH且R2是C1-C6卤代烷基(优选三氟甲基)的具有式I-Q1的化合物(限定具有式I-Q1-A的化合物)
方案6:
可以由具有式(XIII)的化合物(其中X、R1、n、R7、R8和A如式I中所定义)和具有式(XI-A)的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基))根据上文在方案4中且例如在WO2015/000715中描述的方法和条件制备(方案6)。
在Rf是三氟甲基的特定情况下,具有式(XI-A)的化合物可以从可商购获得的反应物1和1’经由方案7中所示的顺序并根据WO 2011/161612、US 7767687、WO 2002/050062、WO2016/046071和WO 2015/000715中描述的方法制备。
方案7:
然而,所描述的路线包括许多降低所需最终产物的收率和质量的反应步骤。特别地,二氨基吡啶中间体7中的一个氮的选择性甲基化需要保护步骤(步骤a)和脱保护步骤(步骤b),这不利地造成整个顺序的原子经济性较低。
替代性地,具有式(XI-A)的化合物或其盐(诸如氢卤化物盐,优选盐酸盐或氢溴酸盐,或任何其他等价盐)(其中Rf是C1-C6卤代烷基(优选三氟甲基))可以有利地由具有式10的化合物或其盐(诸如氢卤化物盐,优选盐酸盐或氢溴酸盐,或任何其他等价盐)(其中Rf是C1-C6卤代烷基(优选三氟甲基))经由卤化和甲胺偶联而制备(方案8)。
方案8:
用于由具有式10的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基))制备具有式11的化合物或其盐(诸如氢卤化物盐,优选盐酸盐或氢溴酸盐,或任何其他等价盐)(其中Rf是C1-C6卤代烷基(优选三氟甲基),并且其中Hal是卤素,优选氯、溴或碘(更优选溴))的合适的卤化剂是例如N-氯代琥珀酰亚胺(NCS)、N-溴代琥珀酰亚胺(NBS)或N-碘代琥珀酰亚胺(NIS),或替代性地氯、溴或碘。此类卤化反应在惰性溶剂(诸如氯仿、四氯化碳、1,2-二氯乙烷、乙酸、醚、乙腈或N,N-二甲基甲酰胺)中,在20℃-200℃,优选室温至100℃的温度下进行。特别优选的是溴化试剂,诸如溴、N-溴代琥珀酰亚胺NBS、1,3-二溴-5,5-二甲基乙内酰脲和H2O2/NH4Br。甚至更优选的是溴化铵NH4Br和过氧化氢(诸如10重量%-30重量%的水溶液)在乙酸溶剂中的组合,温度为20℃-100℃。此类溴化从文献中是已知的,例如从Journalof Molecular Catalysis A:Chemical[分子催化学报A:化学],2007,267,30-33;Heterocycles[杂环],2013,87,1279和Synthetic Communications[合成通讯]2004,34,12,2143-2152中。
甲胺偶联条件涉及使具有式11的化合物或其盐(诸如氢卤化物盐,优选盐酸盐或氢溴酸盐,或任何其他等价盐)(其中Rf是C1-C6卤代烷基(优选三氟甲基),并且其中Hal是卤素,优选氯、溴或碘(更优选溴))与甲胺、甲胺盐(诸如氢卤化物盐,优选盐酸盐或氢溴酸盐,或任何其他等价盐)或合适的甲胺衍生物反应,以形成具有式(XI-A)的化合物或其盐(诸如氢卤化物盐,优选盐酸盐或氢溴酸盐,或任何其他等价盐),其中Rf是C1-C6卤代烷基(优选三氟甲基)。优选地,使用气态甲胺、或甲胺水溶液(强度为10重量%-40重量%)。这种过程可以通过过渡金属催化剂(诸如铜、钯或镍催化剂)任选地在合适的配体存在下催化。优选地,该偶联由铜基催化剂(包括例如碘化铜(I)(Cul)、氯化铜(I)(CuCl)、溴化铜(I)(CuBr)、氧化铜(I)(Cu2O)或硫酸铜(II)(CuSO4))任选地在配体存在下催化。优选的配体是8-羟基喹啉、6,7-二氢-5H-喹啉-8-酮肟和1-(2-吡啶基)乙酮肟。金属催化剂和配体的量可以在0.01mol%与25mol%之间,更优先地在0.1mol%与10mol%之间。该偶联可以在碱(诸如碳酸钠或碳酸钾、磷酸钠或磷酸钾、氢氧化钠或氢氧化钾)存在下,或者替代性地在使用甲胺进料而无另外的碱的情况下进行。典型地,该偶联反应在包含例如水、二噁烷、1,2-二甲氧基乙烷、甲醇、乙醇、四氢呋喃、二噁烷、二甲基亚砜DMSO或甲苯的溶剂或溶剂混合物中进行。优选的溶剂是水,或水与水混溶性共溶剂。优选地,该偶联反应在惰性气氛下,在优先地从室温至200℃,更优先地从50℃至150℃范围内的温度下进行。一些合适的催化剂和偶联条件描述于例如Adv.Synth.Catal.[高级合成与催化]2015,357,714-718和Green Chem.[绿色化学],2012,14,1268-1271中。
方案8中所示的制备具有式(XI-A)的化合物的顺序是特别有利的,因为它避免了方案7中描述的非生产性保护和脱保护步骤。
具有式10的化合物或其盐(诸如氢卤化物盐,优选盐酸盐或氢溴酸盐,或任何其他等价盐)(其中Rf是C1-C6卤代烷基(优选三氟甲基))可由具有式3的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基))经由活化和氨缩合步骤制备(方案9)。
方案9:
具有式12的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基),并且其中LG是离去基团,例如氯、溴或碘(优选氯或溴),或芳基磺酸根(诸如对甲苯磺酸根或甲苯磺酸根-OTs)、烷基磺酸根(诸如甲磺酸根-OMs)或卤代烷基磺酸根(诸如三氟甲磺酸根-OTf))可以通过将具有式3的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基))在本领域技术人员已知的条件下用例如草酰氯、亚硫酰氯、光气、双光气、三光气、三氯氧磷、三溴氧磷、甲磺酰氯、甲苯磺酰氯或三氟甲磺酸酐中的任一种处理而制备。特别地,使具有式3的化合物与草酰氯,任选地在催化量的N,N-二甲基甲酰胺DMF存在下,在惰性溶剂(诸如二氯甲烷、环己烷或甲苯中),在优先地从室温至120℃,更优先地从25℃至100℃的温度下反应,将产生具有式12的化合物,其中LG是氯。
具有式10的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基))可以通过使具有式12的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基),并且其中LG是离去基团,例如氯、溴或碘(优选氯或溴),或芳基磺酸根(诸如对甲苯磺酸根或甲苯磺酸根-OTs)、烷基磺酸根(诸如甲磺酸根-OMs)或卤代烷基磺酸根(诸如三氟甲磺酸根-OTf))与氨NH3或氨等同物(诸如氢氧化铵NH4OH、氯化铵NH4Cl、乙酸铵NH4OAc、碳酸铵(NH4)2CO3和其他NH3替代物)反应而制备。该转化优选地在合适的溶剂(或稀释剂)(诸如醇、酰胺、酯、醚、腈、二甲基亚砜DMSO和水,特别优选的是甲醇、乙醇、2,2,2-三氟乙醇、丙醇、异丙醇、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二噁烷、四氢呋喃、二甲氧基乙烷、乙腈、二甲基亚砜、乙酸乙酯、水或其混合物)中,任选地在铜催化剂(例如碘化铜(I))存在下,有或没有添加剂(诸如L-脯氨酸、N,N'-二甲基环己烷-1,2-二胺或N,N’-二甲基乙二胺),任选地在碱(例如碳酸钾、碳酸钠或碳酸铯)存在下,在优先地从室温至180℃,更优先地从25℃至150℃范围内的温度下,任选地在微波辐射或使用高压釜的加压条件下进行。
替代性地,具有式10的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基))可以经由烷基化、Smiles重排和水解顺序制备(方案9)。在无机或有机碱(诸如碳酸氢钠、碳酸钾、三乙胺或吡啶)存在下,在惰性溶剂(诸如二噁烷、乙腈、甲苯、二甲基亚砜、N-甲基吡咯烷酮、N,N-二甲基甲酰胺或N,N-二甲基乙酰胺)中,在优先地从室温至200℃,更优先地从25℃至120℃的温度下,使具有式3的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基))与2-氯-乙酰胺反应(烷基化)将产生具有式13的化合物,其中Rf是C1-C6卤代烷基(优选三氟甲基)。任选地,可以分离和纯化具有式13的化合物。然而,有利的是,在进一步热活化时,具有式13的化合物可在一锅法中经历Smiles重排,然后在碱性反应条件下原位水解,直接得到所需的具有式10的化合物,其中Rf是C1-C6卤代烷基(优选三氟甲基))。通过将混合物加热至优先地从80℃至250℃,更优先地从120℃至200℃范围内的温度,并任选地使用微波加热来实现热活化。这种有利的一锅法可以类似于例如V.I.Tyvorskii,D.N.Bobrov,O.G.Kulinkovich,K.A.Tehrani,N.De Kimpe,Tetrahedron[四面体]2001,57,2051-2055中的描述而进行。
替代性地,具有式10的化合物或其盐(诸如氢卤化物盐,优选盐酸盐或氢溴酸盐,或任何其他等价盐)(其中Rf是C1-C6卤代烷基(优选三氟甲基))可以更直接地由可方便获得的反应物14(其中Y1独立地是卤素或C1-C4-烷氧基,或具有式14的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4)和反应物15(其中Rf是C1-C6卤代烷基(优选三氟甲基),并且其中Y2是C1-C6烷氧基、氯、氟或C1-C6二烷基-氨基)经由方案10中所示的顺序制备。
方案10:
具有式16的化合物或其盐(其中Rf是C1-C6卤代烷基(优选三氟甲基),并且其中Y1独立地是卤素或C1-C4-烷氧基,或具有式16的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4)可优选地在碱性条件下通过具有式14的化合物(其中Y1独立地是卤素或C1-C4-烷氧基,或具有式14的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4)与具有式15的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基),并且其中Y2是C1-C6烷氧基、氯、氟或C1-C6二烷基氨基)之间的缩合而制备。优选地,Y1是氯、甲氧基或乙氧基,并且Y2是甲氧基或乙氧基。缩合反应可在碱(诸如氢化钠NaH、二异丙基氨基锂LDA、六甲基二硅基胺基锂LiHMDS)存在下进行,或者该碱选自碱金属醇化物,诸如甲醇锂、甲醇钠和甲醇钾,或乙醇锂、乙醇钠和乙醇钾,或异丙醇锂、异丙醇钠和异丙醇钾,或叔丁醇锂、叔丁醇钠和叔丁醇钾。优选地,该碱是甲氧基钠NaOMe或乙氧基钠NaOEt,在溶剂(诸如甲苯、四氢呋喃THF、N-甲基吡咯烷酮NMP或N,N-二甲基甲酰胺DMF(或其混合物))中,在-78℃至120℃,优选0℃-100℃的温度下。在另一个实施例中,将碱溶于一元C1-C4醇,优选乙醇或甲醇,甚至更优选甲醇。溶于甲醇的碱甲醇钠是特别优选的。具有式16的化合物或其盐可以以不同的同分异构(例如E/Z同分异构体)和互变异构形式(例如16、16a和/或16b)存在。本发明涵盖所有比例的所有这些同分异构体和互变异构体及其混合物。
具有式17的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基),并且其中Y1独立地是卤素或C1-C4-烷氧基,或具有式17的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4)可以通过使具有式16的化合物或其盐或其互变异构体(其中Rf是C1-C6卤代烷基(优选三氟甲基),并且其中Y1独立地是卤素或C1-C4-烷氧基,或具有式16的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4)与氨NH3或氨等同物(诸如氢氧化铵NH4OH、氯化铵NH4Cl、溴化铵NH4Br、乙酸铵NH4OAc、甲酸铵NH4HCO2、碳酸铵(NH4)2CO3、硫酸铵和其他NH3替代物)反应而制备。优选地,氨源是气态氨。优选地,Y1是氯、甲氧基或乙氧基。该转化优选地在合适的溶剂(或稀释剂)(诸如酰胺、酯、醚、腈和二甲基亚砜DMSO,特别优选的是N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基吡咯烷酮、乙酸乙酯、四氢呋喃、1,4-二噁烷、乙腈和二甲基亚砜或其混合物)中,在优先地从室温至180℃,更优先地从25℃至150℃范围内的温下,任选地在微波辐射或使用高压釜的加压条件下进行。有利地,该反应在升高的氨压力(例如1巴-10巴)下进行。具有式17的化合物可以以不同的同分异构(例如E/Z同分异构体)和互变异构形式存在。本发明覆盖所有比例的所有这些同分异构体和互变异构体及其混合物。
具有式17的化合物
或其互变异构体和E/Z同分异构体;
其中Rf是C1-C6卤代烷基,优选三氟甲基;并且
Y1独立地是卤素或C1-C4-烷氧基,优选氯、甲氧基或乙氧基;或者
具有式17的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4;
是新型的并针对制备本发明的具有式(XI-A)的化合物而特别开发。因此,具有式17的化合物构成本发明的另一个目的。具有式(XI-A)的化合物的优选取代基定义也适用于具有式17的化合物。
甚至更优选地,具有式17的化合物中的Y1是C1-C4-烷氧基,优选甲氧基或乙氧基。
具有式10的化合物或其盐(诸如氢卤化物盐,优选盐酸盐或氢溴酸盐,或任何其他等价盐)(其中Rf是C1-C6卤代烷基(优选三氟甲基))可以通过使具有式17的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基),并且其中Y1独立地是卤素或C1-C4-烷氧基,或具有式17的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4),在合适的铵盐(例如氯化铵NH4Cl、溴化铵NH4Br、乙酸铵NH4OAc、甲酸铵NH4HCO2、碳酸铵(NH4)2CO3或铵硫酸,优选地,铵源是乙酸铵)存在下,在合适的酸(诸如乙酸或三氟乙酸,优选乙酸)存在下,在合适的溶剂(诸如乙腈、丙腈、1,4-二噁烷、N,N-二甲基甲酰胺、二甲基亚砜或N-甲基吡咯烷酮)中,在50℃至200℃的温度下环化而制备。优选地,Y1是氯、甲氧基或乙氧基。
在上述顺序(方案10)中,可分离具有式17的化合物并任选地进行纯化。在另一方面,本发明提供制备如上定义的具有式10的化合物的方法,该方法包括(方案10a)
方案10a:
使如上定义的具有式16的化合物或其盐、或其互变异构体和E/Z同分异构体与如上所述的氨(优选气态氨),优选地在压力下反应,并且不分离原位形成的化合物17,而将反应混合物直接送至环化步骤。在这种情况下,可以将合适的铵盐(优选乙酸铵)和合适的酸(诸如乙酸或三氟乙酸,优选乙酸)添加到反应混合物中进行环化反应。然后在50℃至200℃的温度下进行加热。
具有式14的化合物是已知的化合物、可商购获得或可通过已知的方法制备。4,4-二甲氧基丁-2-酮、4,4-二乙氧基丁-2-酮和4,4-二氯丁-2-酮是具有式14的化合物的优选实例。
具有式15的化合物是已知的化合物、可商购获得或可通过已知的方法制备。三氟乙酸甲酯和三氟乙酸乙酯是具有式15的化合物的优选实例。
在方案8至10中,Rf优选地是C1-C6氟代烷基,特别优选的是三氟甲基。
总之,本发明还涉及如方案11中所示的制备具有式(XI-A)的化合物的新方法。
方案11:
因此,本发明还提供了用于制备以下项的方法:具有式(XI-A)的化合物
或其盐,
其中Rf是C1-C6卤代烷基,优选三氟甲基,
该方法包括
a.使具有式14的化合物
其中Y1独立地是卤素或C1-C4-烷氧基,优选氯、甲氧基或乙氧基;或者
具有式14的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4;
与具有式15的化合物
其中Rf是C1-C6卤代烷基,优选三氟甲基;并且
Y2是C1-C6烷氧基、氯、氟或C1-C6二烷基氨基,优选甲氧基或乙氧基;
在碱存在下进行反应,以产生具有式16的化合物
或其盐;
或其互变异构体和E/Z同分异构体;
其中Rf是C1-C6卤代烷基,优选三氟甲基;并且
Y1独立地是卤素或C1-C4-烷氧基,优选氯、甲氧基或乙氧基;或者
具有式16的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4;并且
b.使具有式16的化合物
或其盐;
或其互变异构体和E/Z同分异构体;
其中Rf是C1-C6卤代烷基,优选三氟甲基;并且
Y1独立地是卤素或C1-C4-烷氧基,优选氯、甲氧基或乙氧基;或者
具有式16的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4;
与氨或其盐进行反应;
以产生具有式17的化合物
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或其互变异构体和E/Z同分异构体;
其中Rf是C1-C6卤代烷基,优选三氟甲基;并且
Y1独立地是卤素或C1-C4-烷氧基,优选氯、甲氧基或乙氧基;或者
具有式17的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4;并且
c.使具有式17的化合物
或其互变异构体和E/Z同分异构体;
其中Rf是C1-C6卤代烷基,优选三氟甲基;并且
Y1独立地是卤素或C1-C4-烷氧基,优选氯、甲氧基或乙氧基;或者
具有式17的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4;
与铵盐;
在酸存在下进行反应,以产生具有式10的化合物
或其盐;
其中Rf是C1-C6卤代烷基,优选三氟甲基;并且
d.使具有式10的化合物
或其盐;
其中Rf是C1-C6卤代烷基,优选三氟甲基;
与卤化剂进行反应;
以产生具有式11的化合物
或其盐;
其中Rf是C1-C6卤代烷基,优选三氟甲基;并且
Hal是卤素,优选氯、溴或碘,更优选溴;并且
e.使具有式11的化合物
或其盐;
其中Rf是C1-C6卤代烷基,优选三氟甲基;并且
Hal是卤素,优选氯、溴或碘,更优选溴;
与甲胺或其盐进行反应;
以产生具有式(XI-A)的化合物
或其盐;
其中Rf是C1-C6卤代烷基,优选三氟甲基。
优选地,步骤a.在合适的碱存在下进行。上面给出了合适的碱的实例。
优选地,步骤b.中的氨源是气态氨。甚至更优选地,该反应在升高的氨压力下进行。
优选地,步骤c.在合适的铵盐存在下进行。上面给出了合适的铵盐的实例。优选地,铵源是乙酸铵。优选地,步骤c.在合适的酸存在下进行。上面给出了合适的酸的实例。优选地,酸是乙酸。
优选地,步骤d.中的卤化剂是溴化剂。上面给出了溴化剂的实例。甚至更优选地,溴化剂是溴化铵和过氧化氢的组合,在乙酸溶剂中进行。在另一方面,本发明提供了用于制备具有式11的化合物的方法,该方法包括执行如上定义的步骤d.,由此将具有式10的化合物的乙酸溶液
i.在溴化铵存在下加热以形成反应混合物;并且
ii.将该反应混合物用过氧化氢水溶液处理。
优选地,步骤e.在合适的铜催化剂存在下且任选地在合适的配体存在下进行。上面给出了合适的铜催化剂和任选的配体的实例。优选地,在步骤e.中使用气态甲胺、或甲胺水溶液(强度为10重量%-40重量%)。
在另一方面,本发明还提供了用于制备如上定义的具有式10的化合物的方法,该方法包括
b1.使具有式16的化合物
或其盐;
或其互变异构体和E/Z同分异构体;
其中Rf是C1-C6卤代烷基,优选三氟甲基;并且
Y1独立地是卤素或C1-C4-烷氧基,优选氯、甲氧基或乙氧基;或者
具有式16的化合物中的两个基团Y1一起形成基团-O-(CH2)m-O-,其中m是2、3或4;
与氨或其盐进行反应;
以产生反应混合物;并且
b2.使所述混合物直接
与铵盐;
在酸存在下进行反应以产生具有式10的化合物
或其盐;
其中Rf是C1-C6卤代烷基,优选三氟甲基。
优选地,步骤b1.中的氨源是气态氨。甚至更优选地,该反应在升高的氨压力下进行。
优选地,步骤b2.在合适的铵盐存在下进行。上面给出了合适的铵盐的实例。优选地,铵源是乙酸铵。优选地,步骤b2.在合适的酸存在下进行。上面给出了合适的酸的实例。优选地,酸是乙酸。
如上所述由反应物14和15产生具有式10的化合物(其中Rf是C1-C6卤代烷基(优选三氟甲基))的顺序(方案11)是特别有利的,因为它具有较少的步骤并且避免了具有式3的化合物中的4-羟基基团的活化,否则会降低原子经济性并在取代步骤中生成化学计量的废物。在WO 2011/161612中描述了具有式3和12的化合物以及将3转化为12的方法。
在上述条件下由具有式16的化合物直接形成具有式10的化合物而不用分离17可能会令人惊讶,因为WO 2011/161612中公开的类似条件则提供具有式3的吡啶-4-醇化合物。
替代性地,其中Q是Q2的具有式I的化合物(限定具有式I-Q2的化合物,
其中X、R1、n、R7、R8、A、G3和R2如式I中所定义)
方案12:
可通过以下方式制备(方案12):使具有式(XVII)的化合物(其中X、R1、n、R7、R8和A如式I中所定义,并且其中Xc是离去基团,例如氯、溴或碘(优选氯或溴))与具有(XVIII)的化合物(其中G3和R2如式I中所定义),在惰性溶剂(例如乙醇或乙腈)中,任选地在合适的碱(例如碳酸钠、碳酸钾或碳酸铯)存在下,在80℃至150℃的温度下,任选地在微波加热条件下缩合。此类方法先前已经描述在例如WO 2012/49280或WO 2003/031587中。其中G3和R2如式I中所定义的具有式(XVIII)的化合物是已知的化合物、可商购获得或可通过本领域技术人员已知的已知方法制备。
具有式(XVII)的化合物(其中X、R1、n、R7、R8和A如式I中所定义,并且其中Xc是离去基团,例如氯、溴或碘(优选氯或溴))
方案13:
可通过以下方式制备(方案13):将具有式(XIXa)的化合物或具有式(XIXb)的化合物(其中X、R1、R7、R8和A如式I中所定义)用卤化剂(“Xc+”源)(例如N-溴代琥珀酰亚胺、N-碘代琥珀酰亚胺、N-氯代琥珀酰亚胺、I2、CuBr2、乙酸中的Br2、PhNMe3 +Br3 -),典型地在溶剂(诸如甲醇、乙腈、四氢呋喃、乙酸乙酯、氯仿或二氯甲烷或其混合物)中,在0℃至150℃,优选在室温至120℃的温度下,任选地在微波加热条件下处理。此类方法先前已经描述在例如WO2016/071214中。
具有式(XIXa)的化合物(其中X、R1、R7、R8和A如式I中所定义)可以通过以下方式制备:使具有式(XX)的化合物(其中X、R1和A如式I中所定义,并且其中Xa是离去基团,例如氯、溴或碘(优选氯或溴),或芳基磺酸根、烷基磺酸根或卤代烷基磺酸根,例如三氟甲磺酸根)与具有式III的试剂HN=S(O)R7R8(其中R7和R8如式I中所定义)在上文已描述的条件下(参见方案1,化合物II转化为Ia)反应。
具有式(XIXa)的化合物(其中X、R1、R7、R8和A如式I中所定义)也可以通过以下方式制备:使具有式(XIXb)的化合物(其中X、R1、R7、R8和A如式I中所定义)在上文已描述的条件下(参见方案2a,化合物Ib转化为Ia)氧化。替代性地,具有式(XIXa)的化合物(其中X、R1、R7、R8和A如式I中所定义)也可以由具有式(XXI)的化合物(其中X、R1和A如式I中所定义)在上文已描述的条件下(参见方案2a,化合物IV转化为Ia)制备。
具有式(XIXb)的化合物(其中X、R1、R7、R8和A如式I中所定义)可以通过使具有式(XXI)的化合物(其中X、R1和A如式I中所定义)与具有式VI的试剂S(O)R7R8(其中R7和R8如式I中所定义)在上文已描述的条件下(参见方案2b,化合物IV转化为Ib)反应而制备。替代性地,具有式(XIXb)的化合物(其中X、R1、R7、R8和A如式I中所定义)可以通过使具有式(XXI)的化合物(其中X、R1和A如式I中所定义)与具有式V的试剂SR7R8(其中R7和R8如式I中所定义)在上文已描述的条件下(参见方案2a,化合物IV转化为Ib)反应而制备。
具有式(XXI)的化合物(其中X、R1和A如式I中所定义)可以由具有式(XX)的化合物(其中X、R1和A如式I中所定义,并且其中Xa是离去基团,例如氯、溴或碘(优选氯或溴),或芳基磺酸根、烷基磺酸根或卤代烷基磺酸根,例如三氟甲磺酸根)在上文已描述的条件下(参见方案3,化合物II转化为IV)制备。
具有式(XX)的化合物(其中X、R1和A如式I中所定义,并且其中Xa是离去基团,例如氯、溴或碘,或芳基磺酸根、烷基磺酸根或卤代烷基磺酸根,例如三氟甲磺酸根),特别是那些其中Xa是卤素(甚至更优选地氯、溴或碘;特别优选的是氯或溴)的化合物是已知的化合物、可商购获得或可通过在文献中描述的已知方法制备,例如在WO 2016/071214中。
反应物可在碱存在下反应。合适的碱的实例是碱金属或碱土金属氢氧化物、碱金属或碱土金属氢化物、碱金属或碱土金属酰胺、碱金属或碱土金属醇盐、碱金属或碱土金属乙酸盐、碱金属或碱土金属碳酸盐、碱金属或碱土金属二烷基酰胺或者碱金属或碱土金属烷基甲硅烷基酰胺、烷基胺、亚烷基二胺、游离或N-烷基化的饱和或不饱和环烷基胺、碱性杂环化合物、氢氧化铵和碳环胺。可提及的实例是氢氧化钠、氢化钠、氨基钠、甲醇钠、乙酸钠、碳酸钠、叔丁醇钾、氢氧化钾、碳酸钾、氢化钾、二异丙基氨基锂、双(三甲基甲硅烷基)氨基钾、氢化钙、三乙胺、二异丙基乙胺、三亚乙基二胺、环己胺、N-环己基-N,N-二甲基胺、N,N-二乙基苯胺、吡啶、4-(N,N-二甲基氨基)吡啶、奎宁环、N-甲基吗啉、苄基三甲基氢氧化铵和1,8-二氮杂二环[5.4.0]十一碳-7-烯(DBU)。
反应物可以原样相互反应,即不添加溶剂或稀释剂。然而,在大多数情况下,添加惰性溶剂或稀释剂或这些物质的混合物是有利的。如果反应在碱存在下进行,则过量使用的碱如三乙胺、吡啶、N-甲基吗啉或N,N-二乙基苯胺也可用作溶剂或稀释剂。
该反应有利地是在从约-80℃到约+140℃,优选从约-30℃到约+100℃,在许多情况下在介于环境温度与约+80℃之间的温度进行。
具有式I的化合物能以本身已知的方法转化为另一种具有式I的化合物,这是通过以常规方式将具有式I的起始化合物的一个或多个取代基用根据本发明的另一个或其他一个或多个取代基的替代来实现的。
取决于所选的适合各自情况的反应条件以及起始材料,有可能例如,在一个反应步骤中仅将一个取代基用根据本发明的另一个取代基替代,或者在同一个反应步骤中可以将多个取代基用多个根据本发明的其他取代基来替代。
具有式I的这些化合物的盐能以本身已知的方式进行制备。因此,例如,具有式I的化合物的酸加成盐是通过用适合的酸或合适的离子交换试剂进行处理来获得的,并且与碱的盐是通过用适合的碱或用合适的离子交换试剂进行处理来获得的。
具有式I的化合物的盐能以常规方式转化为游离的化合物I、酸加成盐(例如通过用合适的碱性化合物或用合适的离子交换试剂进行处理)以及碱盐(例如通过用合适的酸或用合适的离子交换试剂进行处理)。
具有式I的化合物的盐能以本身已知的方式转化为具有式I的化合物的其他盐、酸加成盐,例如转变成为其他酸加成盐,例如通过在合适的溶剂中用酸的合适的金属盐(如钠盐、钡盐或银盐,例如用乙酸银)来处理无机酸的盐(如盐酸盐),在该合适的溶剂中所形成的无机盐(例如氯化银)是不溶的并且因此从该反应混合物中沉淀出。
取决于程序或反应条件,具有成盐性质的具有式I的化合物可以游离形式或盐形式获得。
根据分子中存在的不对称碳原子的数目、绝对和相对构型和/或根据分子中存在的非芳香族双键的构型,在每种情况下为游离形式或为盐形式的具有式I的化合物和适当时其互变异构体可以可能的同分异构体之一的形式或作为其混合物存在,例如以纯同分异构体的形式,如对映体和/或非对映体,或作为同分异构体混合物,如对映异构体混合物,例如外消旋体、非对映体混合物或外消旋体混合物存在;本发明涉及纯同分异构体以及所有可能的同分异构体混合物,并且在上文和下文中都应如此理解,即使立体化学细节未在所有情况下明确提及。
处于游离形式或处于盐形式的具有式I的化合物的非对映异构体混合物或外消旋体混合物(它们的获得可以取决于已选定的起始材料和程序)能够在这些组分的物理化学差异的基础上,例如通过分步结晶、蒸馏和/或层析法以已知的方式分离成纯的非对映异构体或外消旋体。
能够以类似方式获得的对映异构体混合物(如外消旋体)可以通过已知方法拆分成光学对映体,例如通过从光学活性溶剂再结晶;通过在手性吸附剂上的层析法,例如在乙酰纤维素上的高效液相层析法(HPLC);借助于合适的微生物,通过用特异性固定化酶裂解;通过形成包含化合物,例如使用手性冠醚,其中仅一种对映异构体被络合;或通过转化成非对映异构盐,例如通过使碱性最终产物外消旋体与光学活性酸(如羧酸例如樟脑酸、酒石酸或苹果酸,或磺酸例如樟脑磺酸)反应,并且分离能够以此方式获得的非对映异构体混合物,例如基于其不同溶解度通过分步结晶,从而获得非对映异构体,从这些非对映异构体可以通过合适的试剂(例如碱性试剂)的作用使所希望的对映异构体变成游离。
纯的非对映异构体或对映异构体能根据本发明来获得,不仅是通过分离合适的异构体混合物,还可以是通过普遍已知的非对映立体选择性或对映选择性合成的方法,例如通过根据本发明利用一种合适的立体化学的起始材料进行该方法。
可以通过使具有式I的化合物与适合的氧化剂(例如H2O2/尿素加合物)在酸酐(例如三氟乙酸酐)的存在下进行反应来制备N-氧化物。此类氧化从文献中是已知的,例如从J.Med.Chem.[药物化学杂志],32(12),2561-73,1989或WO 00/15615中。
如果单个组分具有不同的生物活性,有利的是在每一情况下分离或合成生物学上更有效的异构体,例如对映异构体或非对映异构体或异构体混合物,例如对映异构体混合物或非对映异构体混合物。
如果适当的话,具有式I的化合物和适当时其互变异构体(在每种情况下处于游离形式或处于盐形式)还能以水合物的形式获得和/或包括其他溶剂,例如可以用于使以固体形式存在的化合物结晶的那些。
根据下表1至9的化合物可以按照上述方法制备。随后的这些实例旨在说明本发明并展示具有式I的优选化合物。
表1:该表披露了14种具有式I-1a的化合物1.001至1.014:
其中X11是S,并且A、R11、G1、R2、n、R7和R8如下定义:
表1:
以及表1的化合物的N-氧化物。环C3是环丙基。
表2:该表披露了14种具有式I-1a的化合物2.001至2.014,其中X11是SO,并且A、R11、G1、R2、n、R7和R8如表1中所定义。
表3:该表披露了14种具有式I-1a的化合物3.001至3.014,其中X11是SO2,并且A、R11、G1、R2、n、R7和R8如表1中所定义。
表4:该表披露了9种具有式I-2a的化合物4.001至4.009:
其中X11是S,并且A、R11、G3、R2、n、R7和R8如下定义:
表4:
以及表4的化合物的N-氧化物。环C3是环丙基。
表5:该表披露了9种具有式I-2a的化合物5.001至5.009,其中X11是SO,并且A、R11、G3、R2、n、R7和R8如表4中所定义。
表6:该表披露了9种具有式I-2a的化合物6.001至6.009,其中X11是SO2,并且A、R11、G3、R2、n、R7和R8如表4中所定义。
表7:该表披露了4种具有式I-3a的化合物7.001至7.004:
其中X11是S,并且A、R11、G2、G3、R2、n、R7和R8如下定义:
表7:
以及表7的化合物的N-氧化物。环C3是环丙基。
表8:该表披露了4种具有式I-3a的化合物8.001至8.004,其中X11是SO,并且A、R11、G2、G3、R2、n、R7和R8如表7中所定义。
表9:该表披露了4种具有式I-3a的化合物9.001至9.004,其中X11是SO2,并且A、R11、G2、G3、R2、n、R7和R8如表7中所定义。
根据本发明的具有式I的化合物在有害生物控制领域中是有预防和/或治疗价值的活性成分,即使是在低的施用量下,它们具有非常有利的杀生物谱并且是温血物种、鱼以及植物良好耐受的。根据本发明的这些活性成分作用于正常敏感的以及还有抗药的动物有害生物(如昆虫或蜱螨目的代表)的所有的或个别的发育阶段。根据本发明的活性成分的杀昆虫或杀螨活性可以本身直接表现出来,即立即或仅在过去一些时间之后(例如在蜕皮期间)发生对有害生物的破坏;或间接表现出来,例如降低产卵和/或孵化率,对应于至少50%至60%的破坏率(死亡率)的良好活性。
上述动物有害生物的实例是:
来自蜱螨目,例如
下毛瘿螨属(Acalitus spp.)、针刺瘿螨属(Aculus spp)、窄瘿螨属(Acaricalusspp.)、瘤瘿螨属(Aceria spp.)、粗脚粉螨(Acarus siro)、钝眼蜱属(Amblyomma spp.)、锐缘蜱属(Argas spp.)、牛蜱属(Boophilus spp.)、短须螨属(Brevipalpus spp.)、苔螨属(Bryobia spp)、上三节瘿螨属(Calipitrimerus spp.)、皮螨属(Chorioptes spp.)、鸡皮刺螨(Dermanyssus gallinae)、表皮螨属(Dermatophagoides spp)、始叶螨属(Eotetranychus spp)、瘿螨属(Eriophyes spp.)、半跗线螨属(Hemitarsonemus spp)、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、小爪螨属(Olygonychus spp)、钝缘蜱属(Ornithodoros spp.)、侧多食跗线螨(Polyphagotarsone latus)、全爪螨属(Panonychusspp.)、桔芸锈螨(Phyllocoptruta oleivora)、植食螨(Phytonemus spp.)、跗线螨属(Polyphagotarsonemus spp)、痒螨属(Psoroptes spp.)、扇头蜱属(Rhipicephalusspp.)、根嗜螨属(Rhizoglyphus spp.)、疥螨属(Sarcoptes spp.)、狭跗线螨属(Steneotarsonemus spp)、跗线属(Tarsonemus spp.)以及叶螨属(Tetranychus spp.);
来自虱目,例如
血虱属(Haematopinus spp.)、长颚虱属(Linognathus spp.)、人虱(Pediculusspp.)、天疱疮属(Pemphigus spp.)以及木虱(Phylloxera spp.);
来自鞘翅目,例如
缺隆叩甲属(Agriotes spp.)、欧洲鳃角金龟(Amphimallon majale)、东方异丽金龟(Anomala orientalis)、花象属(Anthonomus spp.)、蜉金龟属(Aphodius spp)、玉米拟花萤(Astylus atromaculatus)、Ataenius属、甜菜隐食甲(Atomaria linearis)、甜菜胫跳甲(Chaetocnema tibialis)、萤叶甲属(Cerotoma spp)、单叶叩甲属(Conoderus spp)、根颈象属(Cosmopolites spp.)、绿金龟(Cotinisnitida)、象虫属(Curculio spp.)、圆头犀金龟属(Cyclocephala spp)、圆头犀金龟属(Dermestes spp.)、根萤叶甲属(Diabroticaspp.)、阿根廷兜虫(Diloboderus abderus)、食植瓢虫属(Epilachna spp.)、Eremnus属、黑异爪蔗金龟(Heteronychus arator)、咖啡果小蠹(Hypothenemus hampei)、Lagriavilosa、马铃薯甲虫(Leptinotarsa decemLineata)、稻水象属(Lissorhoptrus spp.)、Liogenys属、Maecolaspis属、栗色绒金龟(Maladera castanea)、美洲叶甲亚种(Megascelis spp)、油菜花露尾甲(Melighetes aeneus)、金龟属(Melolontha spp.)、Myochrous armatus、锯谷盗属(Orycaephilus spp.)、耳喙象属(Otiorhynchus spp.)、鳃角金龟属(Phyllophaga spp.)、斑象属(Phlyctinus spp.)、丽金龟属(Popillia spp.)、油菜跳甲属(Psylliodes spp.)、Rhyssomatus aubtilis、劫根蠹属(Rhizopertha spp.)、金龟子科(Scarabeidae)、米象属(Sitophilus spp.)、麦蛾属(Sitotroga spp.)、伪切根虫属(Somaticus spp.)、Sphenophorus属、大豆茎象(Sternechus subsignatus)、拟步行虫属(Tenebrio spp.)、拟谷盗属(Tribolium spp.)以及斑皮蠹属(Trogoderma spp.);
来自双翅目,例如
伊蚊属(Aedes spp.)、疟蚊属(Anopheles spp)、高梁芒蝇(Antherigonasoccata.)、橄榄果实蝇(Bactrocea oleae)、花园毛蚊(Bibio hortulanus)、迟眼蕈蚊属(Bradysia spp.)、红头丽蝇(Calliphora erythrocephala)、小条实蝇属(Ceratitisspp.)、金蝇属(Chrysomyia spp.)、库蚊属(Culex spp.)、黄蝇属(Cuterebra spp.)、寡鬃实蝇属(Dacus spp.)、地种蝇属(Delia spp)、黑腹果蝇(Drosophilamelanogaster)、厕蝇属(Fannia spp.)、胃蝇属(Gastrophilus spp.)、Geomyza tripunctata、舌蝇属(Glossinaspp.)、皮蝇属(Hypoderma spp.)、虱蝇属(Hyppobosca spp.)、斑潜蝇属(Liriomyzaspp.)、绿蝇属(Lucilia spp.)、潜蝇属(Melanagromyza spp.)、家蝇属(Musca spp.)、狂蝇属(Oestrus spp.)、瘿蚊属(Orseolia spp.)、瑞典麦秆蝇(Oscinella frit)、藜泉蝇(Pegomyia hyoscyami)、草种蝇属(Phorbia spp.)、绕实蝇属(Rhagoletis spp)、Riveliaquadrifasciata、Scatella属、蕈蚊属(Sciara spp.)、刺蝇属(Stomoxys spp.)、虻属(Tabanus spp.)、绦虫属(Tannia spp.)以及大蚊属(Tipula spp.);
来自半翅目,例如
瘤缘蝽(Acanthocoris scabrator)、绿蝽属、苜蓿盲蝽、Amblypeltanitida、海虾盾缘蝽(Bathycoelia thalassina)、土长蝽属、臭虫属、Clavigralla tomentosicollis、盲蝽属(Creontiades spp.)、可可瘤盲蝽、Dichelops furcatus、棉红蝽属、Edessa属、美洲蝽属(Euchistus spp.)、六斑菜蝽(Eurydema pulchrum)、扁盾蝽属、茶翅蝽、具凹巨股长蝽(Horciasnobilellus)、稻缘蝽属、草盲蝽属、热带硕蚧属、卷心菜斑色蝽(Murgantiahistrionic)、Neomegalotomus属、烟盲蝽(Nesidiocoris tenuis)、绿蝽属、拟长蝽(Nysiussimulans)、Oebalus insularis、皮蝽属、壁蝽属、红猎蝽属、可可盲蝽象、Scaptocoriscastanea、黑蝽属(Scotinophara spp.)、Thyanta属、锥鼻虫属、木薯网蝽(Vatigailludens);
无网长管蚜属、Adalges属、Agalliana ensigera、Agonoscena targionii、粉虱属(Aleurodicus spp.)、刺粉虱属(Aleurocanthus spp.)、甘蔗穴粉虱、软毛粉虱(Aleurothrixus floccosus)、甘蓝粉虱(Aleyrodes brassicae)、棉叶蝉(Amarascabiguttula)、Amritodus atkinson、肾圆盾蚧属、蚜科、蚜属、蚧属(Aspidiotus spp.)、茄沟无网蚜、Bactericera cockerelli、小粉虱属、短尾蚜属(Brachycaudus spp.)、甘蓝蚜、喀木虱属、双尾蚜(Cavariella aegopodii Scop.)、蜡蚧属、褐圆蚧、网籽草叶圆蚧、Cicadella属、大白叶蝉(Cofana spectra)、隐瘤蚜属、Cicadulina属、褐软蚧、玉米黄翅叶蝉、裸粉虱属、柑橘木虱、麦双尾蚜、西圆尾蚜属、小绿叶蝉属、苹果绵蚜、葡萄斑叶蝉属、蜡蛤属、赤桉木虱(Glycaspis brimblecombei)、菜缢管蚜、大尾蚜属(Hyalopterus spp.)、超瘤蚜种、檬果绿叶蝉(Idioscopus clypealis)、Jacobiasca lybica、灰飞虱属、球坚蚧、蛎盾蚧属、萝卜蚜(Lopaphis erysimi)、Lyogenys maidis、长管蚜属、Mahanarva属、蛾蜡蝉科(Metcalfa pruinosa)、麦无网蚜、Myndus crudus、瘤蚜属、台湾韭蚜、黑尾叶蝉属、褐飞虱属(Nilaparvata spp.)、梨大绿蚜、Odonaspis ruthae、寄生甘蔗绵蚜、杨梅缘粉虱、考氏木虱、片盾蚧属、瘿绵蚜属、玉米蜡蝉、扁角飞虱属、忽布疣蚜、根瘤蚜属、动性球菌属、白盾蚧属、粉蚧属、棉盲蝽(Pseudatomoscelis seriatus)、木虱属、棉蚧(Pulvinariaaethiopica)、笠圆盾蚧属、Quesada gigas、电光叶蝉(Recilia dorsalis)、缢管蚜属、黑盔蚧属、带叶蝉属、二叉蚜属、麦蚜属(Sitobion spp.)、白背飞虱、苜蓿膜翅角蝉(Spissistilus festinus)、条斑飞虱(Tarophagus Proserpina)、声蚜属、粉虱属、Tridiscus sporoboli、葵粉蚧属(Trionymus spp.)、非洲木虱、桔矢尖蚧、Zyginaflammigera、Zyginidia scutellaris;
来自膜翅目,例如
顶切叶蚁属(Acromyrmex)、三节叶蜂属(Arge spp.)、布切叶白蚁属(Atta spp.)、茎叶蜂属(Cephus spp.)、松叶蜂属(Diprion spp.)、锯角叶蜂科(Diprionidae)、松叶蜂(Gilpinia polytoma)、梨实蜂属(Hoplocampa spp.)、毛蚁属(Lasius spp.)、小黄家蚁(Monomorium pharaonis)、新松叶蜂属(Neodiprion spp.)、农蚁属(Pogonomyrmex spp)、Slenopsis invicta、水蚁属(Solenopsis spp.)以及胡蜂属(Vespa spp.);
来自等翅目,例如
家白蚁属(Coptotermes spp)、白蚁(Corniternes cumulans)、楹白蚁属(Incisitermes spp)、大白蚁属(Macrotermes spp)、澳白蚁属(Mastotermes spp)、小白蚁属(Microtermes spp)、散白蚁属(Reticulitermes spp.);热带火蚁(Solenopsisgeminate)
来自鳞翅目(Lepidoptera),例如,
长翅卷蛾属、褐带卷蛾属、透翅蛾属、地夜蛾属、棉叶虫、Amylois属、黎豆夜蛾、黄卷蛾属、银蛾属(Argyresthia spp.)、带卷蛾属、丫纹夜蛾属、棉潜蛾、玉米楷夜蛾、粉斑螟蛾、桃蛀果蛾、禾草螟属、卷叶蛾属、越蔓桔草螟(Chrysoteuchia topiaria)、葡萄果蠹蛾、卷叶螟属、云卷蛾属、纹卷蛾属、鞘蛾属、磷翅目粉蝶、Cosmophila flava、草螟属、大菜螟、苹果异形小卷蛾、黄杨木蛾、小卷蛾属、黄杨绢野螟、杆草螟属、苏丹棉铃虫、金刚钻属、非洲茎螟、粉螟属、叶小卷蛾属(Epinotia spp.)、细斑灯蛾、Etiella zinckinella、花小卷蛾属、环针单纹蛾、黄毒蛾属、切根虫属、Feltia jaculiferia、小食心虫属(Grapholitaspp.)、绿青虫蛾、实夜蛾属、菜螟、切叶野螟属(Herpetogramma spp.)、美国白蛾、番茄蠹蛾、Lasmopalpus lignosellus、旋纹潜叶蛾、潜叶细蛾属、葡萄花翅小卷蛾、Loxostegebifidalis、毒蛾属、潜蛾属、幕枯叶蛾属、甘蓝夜蛾、烟草天蛾、光腹夜蛾属(Mythimnaspp.)、夜蛾属、秋尺蛾属、Orniodes indica、欧洲玉米螟、超小卷蛾属、褐卷蛾属、小眼夜蛾、蛀茎夜蛾、Pectinophora gossypiela、咖啡潜叶蛾、一星黏虫、马铃薯麦蛾、菜粉蝶、粉蝶属、小菜蛾、芽蛾属、尺叶蛾属、薄荷灰夜蛾、西方豆地香(Richia albicosta)、白禾螟属(Scirpophaga spp.)、蛀茎夜蛾属、长须卷蛾属、灰翅夜蛾属、棉大卷叶螟、兴透翅蛾属、异舟蛾属、卷叶蛾属、粉纹夜蛾、番茄斑潜蝇、以及巢蛾属;
来自食毛目(Mallophaga),例如,
畜虱属(Damalinea spp.)和啮毛虱属(Trichodectes spp.);
来自直翅目(Orthoptera),例如,
蠊属(Blatta spp.)、小蠊属(Blattella spp.)、蝼蛄属(Gryllotalpa spp.)、马德拉蜚蠊(Leucophaea maderae)、飞蝗属(Locusta spp.)、北痣蟋蟀(Neocurtillahexadactyla)、大蠊属(Periplaneta spp.)、痣蟋蟀属(Scapteriscus spp.)、以及沙漠蝗属(Schistocerca spp.);
来自啮虫目(Psocoptera),例如,
虱啮属(Liposcelis spp.);
来自蚤目(Siphonaptera),例如,
角叶蚤属(Ceratophyllus spp.)、栉头蚤属(Ctenocephalides spp.)以及开皇客蚤(Xenopsylla cheopis);
来自缨翅目(Thysanoptera),例如,
Calliothrips phaseoli、花蓟马属(Frankliniella spp.)、阳蓟马属(Heliothrips spp)、褐带蓟马属(Hercinothrips spp.)、单亲蓟马属(Parthenothripsspp.)、非洲桔硬蓟马(Scirtothrips aurantii)、大豆蓟马(Sericothrips variabilis)、带蓟马属(Taeniothrips spp.)、蓟马属(Thrips spp);
来自缨尾目(Thysanura),例如,衣鱼(Lepisma saccharina)。
根据本发明的活性成分可用于控制、也就是遏制或破坏上述类型的有害生物,这些有害生物特别出现在植物上,尤其是在农业中、在园艺中以及在林业中的有用的植物和观赏植物上,或者在这些植物的器官上,例如果实、花、叶、茎、块茎或根,并且在一些情况下,甚至在一个随后的时间点形成的植物器官仍保持受保护以抵抗这些有害生物。
特别地,适宜的目标作物是,谷物,如小麦、大麦、黑麦、燕麦、稻、玉米或高梁;甜菜,如糖用甜菜或饲料甜菜;水果,例如梨果、核果或无核小果,如苹果、梨、李子、桃、杏、樱桃或浆果,例如草莓、覆盆子或黑莓;豆科作物,如菜豆、小扁豆、豌豆或大豆;油料作物,如油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻、可可豆或落花生;瓜类作物,如南瓜、黄瓜或甜瓜;纤维植物,如棉花、亚麻、大麻或黄麻;柑橘类水果,如橙子、柠檬、葡萄柚或橘子;蔬菜,如菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、番茄、马铃薯或灯笼椒;樟科,如鳄梨、肉桂或樟脑;以及还有烟草、坚果、咖啡、茄子、甘蔗、荼、胡椒、葡萄藤、蛇麻草、车前草科以及乳胶植物。
本发明的组合物和/或方法还可以用在任何观赏植物和/或蔬菜作物(包括花、灌木、阔叶树和常绿植物)上。
例如,本发明可以用于任何以下观赏植物物种:藿香蓟属、假面花属(Alonsoaspp.)、银莲花属、南非葵、春黄菊属、金鱼草属、紫菀属、秋海棠属(例如丽格海棠、四季秋海棠、球根秋海棠(B.tubéreux))、叶子花属、雁河菊属(Brachycome spp.)、芸苔属(观赏植物)、蒲包草属、辣椒、长春花、美人蕉属、矢车菊属、菊属、瓜叶菊属(银叶菊)、金鸡菊属、青锁龙(Crassula coccinea)、火红萼距花(Cuphea ignea)、大丽花属、翠雀属、荷包牡丹、彩虹菊属(Dorotheantus spp.)、洋桔梗、连翘属、倒挂金钟属、鼠曲草老颧草(Geraniumgnaphalium)、大丁草属、千日红、天芥菜属、向日葵属、木槿属、绣球花属、绣球属、嫣红蔓、凤仙花属(非洲凤仙花)、血苋属(Iresines spp.)、伽蓝菜属、马缨丹、三月花葵、狮耳花、百合属、日中花属、沟酸浆属、美国薄荷属、龙面花属、万寿菊属、石竹属(康乃馨)、美人蕉属、酢浆草属、雏菊属、天竺葵属(盾叶天竺葵、马蹄纹天竺葵)、堇菜属(三色堇)、碧冬茄属、草夹竹桃属、香茶菜属(Plecthranthus spp.)、一品红属、爬山虎属(五叶爬山虎、爬山虎)、报春花属、毛茛属、杜鹃花属、蔷薇属(玫瑰)、黄雏菊属、非洲堇属、鼠尾草属、紫扇花(Scaevola aemola)、蛾蝶花(Schizanthus wisetonensis)、景天属、茄属、苏非尼亚矮牵牛属(Surfinia spp.)、万寿菊属、烟草属、马鞭草属、百日草属以及其他花坛植物。
例如,本发明可以用于任何以下蔬菜物种:葱属(Allium spp.)(蒜(A.sativum)、玉葱(A.cepa)、洋葱(A.oschaninii)、韭葱(A.Porrum)、火葱(A.ascalonicum)、葱(A.fistulosum))、雪维菜(Anthriscus cerefolium)、芹菜(Apium graveolus)、芦笋(Asparagus officinalis)、莙荙菜(Beta vulgarus)、芸苔属(Brassica spp.)(野甘蓝(B.Oleracea)、白菜(B.pekinensis)、芜菁(B.rapa))、辣椒(Capsicum annuum)、鹰嘴豆(Cicer arietinum)、栽培菊苣(Cichorium endivia)、菊苣属(Cichorum spp.)(菊苣(C.intybus)、栽培菊苣(C.endivia))、西瓜(Citrillus Ianatus)、香瓜属(Cucumis spp.)(黄瓜(C.sativus)、甜瓜(C.melo))、南瓜属(Cucurbita spp.)(西葫芦(C.pepo)、笋瓜(C.maxima))、菜蓟属(Cyanara spp.)(洋蓟(C.scolymus)、刺菜蓟(C.cardunculus))、野胡萝卜(Daucus carota)、茴香(Foeniculum vulgare)、金丝桃属(Hypericum spp.)、莴苣(Lactuca sativa)、番茄属(Lycopersicon spp.)(L.esculentum、L.lycopersicum)、薄荷属(Mentha spp.)、罗勒(Ocimum basilicum)、皱叶欧芹(Petroselinum crispurn)、菜豆属(Phaseolus spp.)(菜豆(P.vulgaris)、红花菜豆(P.coccineus))、豌豆(Pisum sativum)、萝卜(Raphanus sativus)、食用大黄(Rheum rhaponticum)、迷迭香属(Rosemarinusspp.)、鼠尾草属(Salvia spp.)、黑婆罗门参(Scorzonera hispanica)、茄子(Solanummelongena)、菠菜(Spinacea oleracea)、新缬草属(Valerianella spp.)(禾穗新缬草(V.locusta)、绵毛果小缬草(V.eriocarpa))和蚕豆(Vicia faba)。
优选的观赏植物物种包括非洲堇(African violet)、秋海棠属、大丽花属、大丁草属、绣球属、马鞭草属、蔷薇属、伽蓝菜属、一品红属、紫菀属、矢车菊属、金鸡菊属、翠雀属、美国薄荷属、草夹竹桃属、黄雏菊属、景天属、碧冬茄属、堇菜属、凤仙花属、老鹳草属、菊属、毛茛属、倒挂金钟属、鼠尾草属、绣球花属、迷迭香、鼠尾草、圣约翰草(St.Johnswort)、薄荷(mint)、甜椒(sweet pepper)、番茄和黄瓜(cucumber)。
根据本发明的这些活性成分尤其适合于控制棉花、蔬菜、玉米、水稻以及大豆作物上的扁豆蚜、黄瓜条叶甲、烟芽夜蛾、桃蚜、小菜蛾以及海灰翅夜蛾。根据本发明的这些活性成分另外尤其适合于控制甘蓝夜蛾(优选地在蔬菜上)、苹果蠹蛾(优选地在苹果上)、小绿叶蝉(优选地在蔬菜、葡萄园里)、马铃薯叶甲(优选地在马铃薯上)以及二化螟(优选地在水稻上)。
根据本发明的这些活性成分尤其适合于控制棉花、蔬菜、玉米、水稻以及大豆作物上的扁豆蚜、黄瓜条叶甲、烟芽夜蛾、桃蚜、小菜蛾以及海灰翅夜蛾。根据本发明的这些活性成分另外尤其适合于控制甘蓝夜蛾(优选地在蔬菜上)、苹果蠹蛾(优选地在苹果上)、小绿叶蝉(优选地在蔬菜、葡萄园里)、马铃薯叶甲(优选地在马铃薯上)以及二化螟(优选地在水稻上)。
在另一个方面中,本发明还可涉及一种控制由植物寄生线虫(内寄生的-、半内寄生的-和外寄生线虫)对植物及其部分的损害的方法,尤其是以下植物寄生线虫,诸如根结线虫(root knot nematodes)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogyne javanica)、花生根结线虫(Meloidogyne arenaria)以及其他根结线虫物种;孢囊形成线虫(cyst-formingnematodes)、马铃薯金线虫(Globodera rostochiensis)以及其他球孢囊线虫属(Globodera)物种;禾谷孢囊线虫(Heterodera avenae)、大豆孢囊线虫(Heteroderaglycines)、甜菜孢囊线虫(Heterodera schachtii)、红三叶异皮线虫(Heteroderatrifolii)、以及其他异皮线虫属(Heterodera)物种;种瘿线虫(Seed gall nematodes)、粒线虫属(Anguina)物种;茎及叶面线虫(Stem and foliar nematodes)、滑刃线虫属(Aphelenchoides)物种;刺毛线虫(Sting nematodes)、长尾刺线虫(Belonolaimuslongicaudatus)以及其他刺线虫属(Belonolaimus)物种;松树线虫(Pine nematodes)、松材线虫(Bursaphelenchus xylophilus)以及其他伞滑刃属(Bursaphelenchus)物种;环形线虫(Ring nematodes)、环线虫属(Criconema)物种、小环线虫属(Criconemella)物种、轮线虫属(Criconemoides)物种、中环线虫属(Mesocriconema)物种;茎及鳞球茎线虫(Stemand bulb nematodes)、(腐烂茎线虫(Ditylenchus destructor)、鳞球茎茎线虫(Ditylenchus dipsaci)以及其他茎线虫属(Ditylenchus)物种;维线虫(Awl nematodes)、锥线虫属(Dolichodorus)物种;螺旋线虫(Spiral nematodes)、多头螺旋线虫(Heliocotylenchus multicinctus)以及其他螺旋线虫属(Helicotylenchus)物种;鞘及鞘形线虫(Sheath and sheathoid nematodes)、鞘线虫属(Hemicycliophora)物种以及半轮线虫属(Hemicriconemoides)物种;潜根线虫属(Hirshmanniella)物种;支线虫(Lancenematodes)、冠线虫属(Hoploaimus)物种;假根结线虫(false rootknot nematodes)、珍珠线虫属(Nacobbus)物种;针状线虫(Needle nematodes)、横带长针线虫(Longidoruselongatus)以及其他长针线虫属(Longidorus)物种;大头针线虫(Pin nematodes)、短体线虫属(Pratylenchus)物种;腐线虫(Lesion nematodes)、花斑短体线虫(Pratylenchusneglectus)、穿刺短体线虫(Pratylenchus penetrans)、弯曲短体线虫(Pratylenchuscurvitatus)、古氏短体线虫(Pratylenchus goodeyi)以及其他短体线虫属物种;柑桔穿孔线虫(Burrowing nematodes)、香蕉穿孔线虫(Radopholus similis)以及其他内侵线虫属(Radopholus)物种;肾状线虫(Reniform nematodes)、罗柏氏盘旋线虫(Rotylenchusrobustus)、肾形盘旋线虫(Rotylenchus reniformis)以及其他盘旋线虫属(Rotylenchus)物种;盾线虫属(Scutellonema)物种;短粗根线虫(Stubby root nematodes)、原始毛刺线虫(Trichodorus primitivus)以及其他毛刺线虫属(Trichodorus)物种、拟毛刺线虫属(Paratrichodorus)物种;矮化线虫(Stunt nematodes)、马齿苋矮化线虫(Tylenchorhynchus claytoni)、顺逆矮化线虫(Tylenchorhynchus dubius)以及其他矮化线虫属(Tylenchorhynchus)物种;柑桔线虫(Citrus nematodes)、穿刺线虫(Tylenchulus)物种;短剑线虫(Dagger nematodes)、剑线虫属(Xiphinema)物种;以及其他植物寄生线虫物种,诸如亚粒线虫属(Subanguina spp.)、根结线虫属(Hypsoperine spp.)、大刺环线虫属(Macroposthonia spp.)、矮化线虫属(Melinius spp.)、刻点胞囊属(Punctoderaspp.)、以及五沟线虫属(Quinisulcius spp.)。
本发明所述的化合物还具有针对软体动物的活性。其实例包括例如福寿螺科;蛞蝓科(Arion)(黑蛞蝓(A.ater)、环状蛞蝓(A.circumscriptus)、棕阿勇蛞蝓(A.hortensis)、红蛞蝓(A.rufus));巴蜗牛科(Bradybaenidae)(灌木巴蜗牛(Bradybaenafruticum));葱蜗牛属(Cepaea)(花园葱蜗牛(C.hortensis)、森林葱蜗牛(C.Nemoralis));ochlodina;野蛞蝓属(Deroceras)(野灰蛞蝓(D.agrestis)、D.empiricorum、光滑野蛞蝓(D.laeve)、网纹野蛞蝓(D.reticulatum));圆盘螺属(Discus)(圆形圆盘蜗牛(D.rotundatus));Euomphalia;土蜗属(Galba)(截口土蜗(G.trunculata));小蜗牛属(Helicelia)(伊塔拉小蜗牛(H.itala)、布维小蜗牛(H.obvia));大蜗牛科(Helicidae)Helicigona arbustorum);Helicodiscus;大蜗牛(Helix)(开口大蜗牛(H.aperta));蛞蝓属(Limax)(利迈科斯蛞蝓(L.cinereoniger)、黄蛞蝓(L.flavus)、边缘蛞蝓(L.marginatus)、大蛞蝓(L.maximus)、柔蛞蝓(L.tenellus));椎实螺属(Lymnaea);Milax(小蛞蝓科)(黑色小蛞蝓(M.gagates)、边缘小蛞蝓(M.marginatus)、硕氏小蛞蝓(M.sowerbyi));钻螺属(Opeas);瓶螺属(Pomacea)(福寿螺(P.canaticulata));瓦娄蜗牛属(Vallonia)和Zanitoides。
术语“作物”应当理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成一种或多种选择性作用毒素的作物植物,这些毒素是如已知例如来自于产毒素细菌,尤其是芽孢杆菌属的那些细菌。
可由此类转基因植物表达的毒素包括例如杀昆虫蛋白,例如来自蜡样芽胞杆菌或日本金龟子芽孢杆菌的杀昆虫蛋白;或者来自苏云金芽孢杆菌的杀昆虫蛋白,诸如δ-内毒素,例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或者营养期杀昆虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A;或细菌定植线虫的杀昆虫蛋白,例如光杆状菌属某些种(Photorhabdus spp.)或致病杆菌属某些种(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,植物凝集素类(lectin),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。
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,例如在Cry3A055的情况下,一种组织蛋白酶-G-识别序列被插入Cry3A毒素中(参见WO 03/018810)。
这样的毒素或能够合成这样的毒素的转基因植物的实例披露于例如EP-A-0 374753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878以及WO 03/052073中。
用于制备这样的转基因植物的方法通常是本领域技术人员已知的并且描述在例如以上提及的公开物中。CryI型脱氧核糖核酸及其制备例如从WO 95/34656、EP-A-0 367474、EP-A-0 401 979和WO 90/13651中已知。
包括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)。
包含一种或多种编码杀昆虫剂抗性并且表达一种或多种毒素的基因的转基因植物是已知的并且其中一些是可商购的。这样的植物的实例是:(玉米品种,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按盐耐药性的酶膦丝菌素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/>
这样的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。这样的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丁膦铵的耐受性。
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菌株CP4获得的蛋白质CP4EPSPS,使之耐除草剂(含有草甘膦),以及由苏云金芽孢杆菌库尔斯塔克亚种获得的Cry1Ab毒素,使之耐某些鳞翅目昆虫,包括欧洲玉米螟。
抗昆虫的植物的转基因作物还描述于BATS(生物安全与可持续发展中心(Zentrumfür Biosicherheit und Nachhaltigkeit),BATS中心(Zentrum BATS),克拉斯崔舍(Clarastrasse)13,巴塞尔(Basel)4058,瑞士)报告2003(http://bats.ch)中。
术语“作物”应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具有选择性作用的抗病原物质的作物植物,这些抗病原物质是例如像所谓的“病程相关蛋白”(PRP,参见例如EP-A-0 392 225)。这样的抗病原物质和能够合成这样的抗病原物质的转基因植物的实例例如从EP-A-0 392 225、WO 95/33818和EP-A-0 353 191是已知的。生产这样的转基因植物的方法对于本领域的普通技术人员而言通常是已知的并且描述于例如以上提及的公开物中。
可由此类转基因植物表达的抗病原物质包括例如离子通道阻断剂,诸如钠通道和钙通道的阻断剂,例如病毒KP1、KP4或KP6毒素;芪合酶;联苄合酶;几丁质酶;葡聚糖酶;所谓“病程相关蛋白”(PRP;参见例如EP-A-0 392 225);由微生物产生的抗病原物质,例如肽抗生素或杂环抗生素(参见例如WO 95/33818)或参与植物病原体防御的蛋白质或多肽因子(所谓“植物疾病抗性基因”,如WO 03/000906所述)。
根据本发明的组合物的其他使用范围是保护所储存的货物和储藏室以及保护原材料,诸如木材、纺织品、地板或建筑物,以及在卫生领域中,尤其是保护人类、家畜以及多产的牲畜免遭所提及类型的有害生物。
本发明还提供了用于控制有害生物(如蚊和其他的疾病媒介物;同样参见http://www.who.int/malaria/vector_control/irs/en/)的方法。在一个实施例中,用于控制有害生物的方法包括通过涂刷、轧制、喷雾、涂布或浸渍,向目标有害生物、它们的场所或表面或基质施用本发明的组合物。通过举例,通过本发明的方法考虑到了表面(诸如墙、天花板或地板表面)的IRS(室内滞留喷雾)施用。在另一个实施例中,考虑到了将此类组合物施用于如下基底,诸如无纺或织物材料,该材料处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中使用)。
在一个实施例中,用于控制此类有害生物的方法包括向目标有害生物、它们的场所或表面或基质施用杀有害生物有效量的本发明的组合物,以便于在该表面或基质上提供有效的滞留的杀有害生物活性。这样的施用可以通过涂刷、轧制、喷雾、涂布或浸渍本发明的杀有害生物组合物来进行。通过举例,通过本发明的方法考虑到了表面(诸如墙、天花板或地板表面)的IRS施用,以便于在该表面上提供有效的滞留的杀有害生物活性。在另一个实施例中,考虑了施用这样的组合物以用于在基底上的有害生物的残留控制,该基底是诸如处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中)的织物材料。
有待处理的基质(包括无纺物、织物或网织品)可以由天然纤维,诸如棉花、拉菲亚树叶纤维、黄麻、亚麻、剑麻、粗麻布或羊毛,或者合成纤维,诸如聚酰胺、聚酯、聚丙烯、聚丙烯腈等等制成。聚酯是特别适合的。纺织品处理的方法是已知的,例如WO 2008/151984、WO2003/034823、US 5631072、WO 2005/64072、WO 2006/128870、EP 1724392、WO 2005/113886或WO 2007/090739。
根据本发明的组合物的其他使用范围是针对所有观赏树木连同所有种类的果树和坚果树的树木注射/树干处理领域。
在树木注射/树干处理领域中,根据本发明的这些化合物特别适合于对抗来自上述鳞翅目和来自鞘翅目的钻木昆虫,尤其是对抗下表A和B中列出的蛀木虫:
表A.具有经济重要性的外来蛀木虫的实例。
表B.具有经济重要性的本地蛀木虫的实例。
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本发明也可以用于控制任何可以存在于草坪草中的昆虫有害生物,包括例如甲虫、毛虫、火蚁、地面珍珠(ground pearl)、千足虫、潮虫、螨虫、蝼蛄、介壳虫、粉蚧蜱、沫蝉、南方麦小蝽以及蛴螬。本发明可以用于控制处于其生命周期的各个阶段的昆虫有害生物,包括卵、幼虫、若虫和成虫。
具体而言,本发明可用于控制用草坪草的根部喂养的昆虫有害生物,该昆虫有害生物包括蛴螬(诸如圆头犀金龟属(Cyclocephala spp.)(例如标记的金龟子、C.lurida)、Rhizotrogus属(例如欧洲金龟子,欧洲切根鳃金龟(R.majalis))、黄栌属(Cotinus spp.)(例如绿六月甲虫(Green June beetle)、C.nitida)、弧丽金龟属(Popillia spp.)(例如日本甲虫、龟纹瓢虫(P.japonica))、鳃角金龟属(Phyllophaga spp.)(例如五月/六月甲虫)、Ataenius属(例如草坪草黑金龟(Black turfgrass ataenius)、A.spretulus)、绒毛金龟属(Maladera spp.)(例如亚洲花园甲虫(Asiatic garden beetle)、M.castanea)以及Tomarus属)、地面珍珠(硕蚧属(Margarodes spp.))、蝼蛄(褐黄色的、南方的、以及短翅的;痣蟋蟀属(Scapteriscus spp.)、非洲蝼蛄(Gryllotalpa africana))以及大蚊幼虫(leatherjackets)(欧洲大蚊(European crane fly)、大蚊属(Tipula spp.))。
本发明还可以用于控制茅草住宅的草坪草的昆虫有害生物,这些昆虫有害生物包括粘虫(诸如秋夜蛾(fall armyworm)草地贪夜蛾(Spodoptera frugiperda),和常见夜蛾一星黏虫(Pseudaletia unipuncta))、切根虫,象鼻虫(尖隐喙象属(Sphenophorus spp.),诸如S.venatus verstitus和牧草长喙象(S.parvulus))以及草地螟(如草螟属(Crambusspp.)和热带草地螟,Herpetogramma phaeopteralis)。
本发明还可以用于控制在地上生活并取食草坪草叶子的草坪草中的昆虫有害生物,这些昆虫有害生物包括麦小蝽(诸如南方麦小蝽,南方杆长蝽(Blissus insularis))、狗牙根螨(Bermudagrass mite)(Eriophyes cynodoniensis)、盖氏虎尾草粉蚧(草竹粉蚧(Antonina graminis))、两线沫蝉(Propsapia bicincta)、叶蝉、切根虫(夜蛾科)、以及麦二叉蚜。
本发明还可以用于控制草坪草中的其他有害生物,诸如在草坪中创建蚁巢的外引红火蚁(红火蚁(Solenopsis invicta))。
在卫生领域中,根据本发明的组合物是有效地对抗外寄生虫诸如硬蜱、软蜱、疥螨、秋螨、蝇(叮咬和舔舐)、寄生性蝇幼虫,虱、发虱、鸟虱和跳蚤。
此类寄生虫的实例是:
虱目:血虱属、长腭虱属、人虱属以及阴虱属、管虱属。
食毛目:毛羽虱属、短角鸟虱属、鸭虱属、牛羽虱属、Werneckiella属、Lepikentron属、畜虱属、啮毛虱属以及猫羽虱属。
双翅目及长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属、疟蚊属、库蚊属、蚋属(Simulium spp.)、真蚋属(Eusimulium spp.)、白蛉属(Phlebotomusspp.)、罗蛉属(Lutzomyia spp.)、库蠓属(Culicoides spp.)、斑虻属(Chrysops spp.)、驼背虻属(Hybomitra spp.)、黄虻属(Atylotus spp.)、虻属、麻虻属(Haematopota spp.)、Philipomyia属、蜂虱蝇属(Braula spp.)、家蝇属、齿股蝇属(Hydrotaea spp.)、螫蝇属、黑角蝇属(Haematobia spp.)、莫蝇属(Morellia spp.)、厕蝇属、舌蝇属、丽蝇属(Calliphoraspp.)、绿蝇属、金蝇属、污蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属、皮蝇属、胃蝇属(Gasterophilus spp.)、虱蝇属(Hippobosca spp.)、羊虱蝇属(Lipoptenaspp.)和蜱蝇属(Melophagus spp.)。
蚤目(Siphonapterida),例如蚤属(Pulex spp.)、栉头蚤属、客蚤属(Xenopsyllaspp.)、角叶蚤属。
异翅目(Heteropterida),例如臭虫属、锥鼻虫属属、红猎蝽属、锥蝽属(Panstrongylus spp.)。
蜚蠊目(Blattarida),例如东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、德国小蠊(Blattelagermanica)以及夏柏拉蟑螂属(Supellaspp.)。
蜱螨(Acaria)亚纲(螨科(Acarida))和后气门目(Meta-stigmata)和中气门目(Meso-stigmata),例如锐缘蜱属、钝缘蜱属(Ornithodorus spp.)、耳蜱属(Otobiusspp.)、硬蜱属、钝眼蜱属、牛蜱属(Boophilus spp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemophysalis spp.)、璃眼蜱属、扇头蜱属、皮刺螨属(Dermanyssus spp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸刺螨属(Sternostoma spp.)和瓦螨属(Varroa spp.)。
轴螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨目(Acaridida)(无气门亚目(Astigmata)),例如蜂盾螨属(Acarapis spp.)、姬螯属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形螨属(Demodex spp.)、恙螨属(Trombicula spp.)、牦螨属(Listrophorus spp.)、粉螨属(Acarus spp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、痒螨属、皮螨属、耳疥螨属(Otodectesspp.)、疥螨属、耳螨属(Notoedres spp.)、鸟疥螨属(Knemidocoptes spp.)、胞螨属(Cytodites spp.)以及鸡雏螨属(Laminosioptes spp.)。
根据本发明的组合物还适用于保护材料诸如木材、纺织品、塑料、粘合剂、胶、漆料、纸张和卡片、皮革、地板和建筑等免受昆虫侵染。
根据本发明的这些组合物可用于,例如,对抗下列有害生物:甲虫,如北美家天牛、多毛绿虎天牛、家具窃蠹、报死窃蠹、Ptilinuspecticornis、Dendrobium pertinex、细齿叉尾长蠹、Priobium carpini、褐粉蠹、非洲粉蠹、南方粉蠹、抱扁蠹、软毛粉蠹、扁腿粉蠹、鳞毛粉蠹、材小蠹属、木小蠹属、黑长蠹、红腹槲长蠹、棕异翅长蠹、双棘长蠢属以及竹蠹,并且还有膜翅目,如蓝黑树蜂、大树蜂、泰加大树蜂和Urocerus augu,以及白蚁类,如黄颈木白蚁、麻头堆砂白蚁、印巴结构木异白蚁、黄肢散白蚁、桑特散白蚁、欧洲散白蚁、达氏澳白蚁、内华达动白蚁和台湾家白蚁,以及无翼昆虫类,如衣鱼。
根据本发明的化合物可以按未经修饰的形式用作杀有害生物剂,但它们通常以多种方式使用配制佐剂(诸如载体、溶剂以及表面活性物质)被配制成组合物。这些配制品可以处于不同的实体形式,例如,处于以下形式:撒粉剂、凝胶、可湿性粉剂、水可分散性颗粒剂、水可分散性片剂、泡腾压缩片剂、可乳化的浓缩物、微可乳化浓缩物、水包油乳剂、可流动油、水性分散体、油性分散体、悬乳剂、胶囊悬浮液、可乳化的颗粒剂、可溶性液体、水可溶性浓缩物(以水或水混溶性有机溶剂作为载体)、浸渍的聚合物膜或处于已知的其他形式,例如从关于杀有害生物剂的FAO和WHO标准的发展和使用的手册(Manual on Developmentand Use of FAO and WHO Specifications for Pesticides),联合国,第1版,二次修订(2010)中已知的。此类配制品可以直接使用或者可以使用前稀释再使用。可以利用例如水、液体肥料、微量营养素、生物有机体、油或溶剂来稀释。
可以通过例如将活性成分与配制品佐剂混合来制备这些配制品以便获得处于精细分散固体、颗粒、溶液、分散体或乳剂形式的组合物。这些活性成分还可以与其他佐剂(例如精细分散固体、矿物油、植物或动物的油、改性的植物或动物的油、有机溶剂、水、表面活性物质或它们的组合)来一起配制。
这些活性成分还可以被包含于非常精细的微胶囊中。微胶囊在多孔载体中含有活性成分。这使活性成分能以受控的量值(例如,缓慢释放)释放到环境中。微胶囊通常具有从0.1至500微米的直径。它们包含的活性成分的量按重量计是胶囊重量的约从25%至95%。这些活性成分可以处于整体性的固体的形式、处于固体或液体分散体中的精细颗粒的形式或处于合适溶液的形式。包囊的膜可以包括例如天然的或合成的橡胶,纤维素、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、聚氨酯或化学改性的聚合物以及淀粉黄原酸酯、或本领域的普通技术人员已知的其他聚合物。可替代地,可以形成非常精细的微胶囊,其中活性成分在基础物质的固体基质中是以精细分散颗粒的形式被包含的,但这些微胶囊本身未经包裹。
适合于制备根据本发明的这些组合物的配制佐剂本身是已知的。作为液体载体可以使用:水、甲苯、二甲苯、石油醚、植物油、丙酮、甲基乙基酮、环己酮、酸酐、乙腈、乙酰苯、乙酸戊酯、2-丁酮、碳酸丁烯酯、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、松脂酸二乙二醇酯、二甘醇丁基醚、二甘醇乙基醚、二甘醇甲醚、N,N-二甲基甲酰胺、二甲基亚砜、1,4-二噁烷、二丙二醇、二丙二醇甲基醚、双丙甘醇二苯甲酸酯、二丙二醇、烷基吡咯烷酮、乙酸乙酯、2-乙基己醇、碳酸乙烯酯、1,1,1-三氯乙烷、2-庚酮、α-蒎烯、d-苧烯、乳酸乙酯、乙二醇、乙二醇丁基醚、乙二醇甲基醚、γ-丁内酯、丙三醇、乙酸甘油酯、二乙酸甘油酯、三乙酸甘油酯、十六烷、己二醇、乙酸异戊基酯、乙酸异冰片基酯、异辛烷、异佛尔酮、异丙苯、肉豆蔻酸异丙酯、乳酸、月桂胺、异亚丙基丙酮、甲氧基丙醇、甲基异戊基酮、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、十八烷酸、辛胺乙酸酯、油酸、油烯基胺、邻二甲苯、苯酚、聚乙二醇、丙酸、乳酸丙酯、碳酸亚丙酯、丙二醇、丙二醇甲基醚、对-二甲苯、甲苯、磷酸三乙酯、三乙二醇、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、丙二醇甲基醚、二乙二醇甲基醚、甲醇、乙醇、异丙醇以及更高分子量的醇,例如戊醇、四氢呋喃醇、己醇、辛醇、乙二醇、丙二醇、甘油、N-甲基-2-吡咯烷酮等。
适合的固体载体是例如滑石、二氧化钛、叶蜡石黏土、硅石、凹凸棒石黏土、硅藻土、石灰石、碳酸钙、膨润土、钙蒙脱土、棉籽壳、小麦粉、大豆粉、浮石、木粉、胡桃壳粉、木质素和类似的物质。
许多表面活性物质可以有利地用在固体和液体配制品两者中,尤其是在使用前可被载体稀释的那些配制品中。表面活性物质可以是阴离子的、阳离子的、非离子的或聚合的并且它们可以用作乳化剂、湿润剂或悬浮剂或用于其他目的。典型的表面活性物质包括例如烷基硫酸酯的盐,如十二烷基硫酸二乙醇铵;烷基芳基磺酸酯的盐,如十二烷基苯磺酸钙;烷基酚/氧化烯加成产物,如乙氧基化壬基苯酚;醇/氧化烯加成产物,如乙氧基化十三烷醇;皂,如硬脂酸钠;烷基萘磺酸酯的盐,如二丁基萘磺酸钠;磺基丁二酸二烷基酯的盐,如二(2-乙基己基)磺基丁二酸钠;山梨糖醇酯,如山梨糖醇油酸酯;季铵,如氯化十二烷基三甲基铵;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-烷酯的盐;以及还有其他物质,例如描述于:McCutcheon'sDetergents and Emulsifiers Annual[麦卡琴清洁剂和乳化剂年鉴],MC出版公司(MCPublishing Corp.),里奇伍德,新泽西州(Ridgewood New Jersey)(1981)。
可以用于杀有害生物配制品的其他佐剂包括结晶作用抑制剂、粘度改性剂、悬浮剂、染料、抗氧化剂、发泡剂、光吸收剂、混合助剂、消泡剂、络合剂、中和或改变pH的物质与缓冲液、腐蚀抑制剂、香料、湿润剂、吸收增强剂、微量营养素、增塑剂、助流剂、润滑剂、分散剂、增稠剂、防冻剂、杀微生物剂、以及液体与固体肥料。
根据本发明的组合物可以包括添加剂,该添加剂包括植物或动物来源的油、矿物油、此类油的烷基酯或此类油与油衍生物的混合物。在根据本发明所述的组合物中的油添加剂的量通常是该待施用的混合物的0.01%到10%。例如,可以在喷雾混合物已经制备以后将该油添加剂以所希望的浓度加入喷雾罐中。优选的油添加剂包括矿物油或植物来源的油,例如菜籽油、橄榄油或葵花籽油;乳化的植物油;植物来源的油的烷基酯,例如甲基衍生物;或动物来源的油,如鱼油或牛脂。优选的油添加剂包括C8-C22脂肪酸的烷基酯,尤其是C12-C18脂肪酸的甲基衍生物,例如月桂酸、棕榈酸以及油酸(分别为月桂酸甲酯、棕榈酸甲酯和油酸甲酯)的甲基酯。许多油衍生物获知于Compendium of Herbicide Adjuvants[除草剂佐剂纲要],第10版,南伊利诺伊大学,2010。
这些本发明组合物总体上包括按重量计从0.1%至99%,尤其是按重量计从0.1%至95%的本发明的化合物以及按重量计从1%至99.9%的配制佐剂,该配制佐剂优选地包括按重量计从0至25%的表面活性物质。而商用产品可以优选地被配制为浓缩物,最终使用者将通常使用稀释配制品。
施用比率在宽范围之内变化并且取决于土壤的性质、施用方法、作物植物、待控制的有害生物、主要气候条件、以及受施用方法、施用时间以及目标作物支配的其他因素。一般来讲,可以将化合物以从1l/ha至2000l/ha,尤其是从10l/ha到1000l/ha的比率施用。
优选的配制品可以具有以下组成(重量%):
可乳化的浓缩物:
活性成分:1%至95%,优选60%至90%
表面活性剂:1%至30%,优选5%至20%
液体载体:1%至80%,优选1%至35%
尘剂:
活性成分:0.1%至10%,优选0.1%至5%
固体载体:99.9%至90%,优选99.9%至99%
悬浮液浓缩物:
活性成分:5%至75%,优选10%至50%
水:94%至24%,优选88%至30%
表面活性剂:1%至40%,优选2%至30%
可湿性粉剂:
活性成分:0.5%至90%,优选1%至80%
表面活性剂:0.5%至20%,优选1%至15%
固体载体:5%至95%,优选15%至90%
颗粒剂:
活性成分:0.1%至30%,优选0.1%至15%
固体载体:99.5%至70%,优选97%至85%
以下实例进一步展示了(但不限制)本发明。
可湿性粉剂 | a) | b) | c) |
活性成分 | 25% | 50% | 75% |
木质素磺酸钠 | 5% | 5% | - |
月桂基硫酸钠 | 3% | - | 5% |
二异丁基萘磺酸钠 | - | 6% | 10% |
苯酚聚乙二醇醚(7-8mol的环氧乙烷) | - | 2% | - |
高度分散的硅酸 | 5% | 10% | 10% |
高岭土 | 62% | 27% | - |
将该组合与这些佐剂充分混合并且将混合物在适当的研磨机中充分研磨,从而获得了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。
干种子处理用的粉剂 | a) | b) | c) |
活性成分 | 25% | 50% | 75% |
轻质矿物油 | 5% | 5% | 5% |
高度分散的硅酸 | 5% | 5% | - |
高岭土 | 65% | 40% | - |
滑石 | - | 20% |
将该组合与佐剂充分混合并且将该混合物在适合的研磨机中充分研磨,从而获得可以直接用于种子处理的粉剂。
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。
尘剂 | a) | b) | c) |
活性成分 | 5% | 6% | 4% |
滑石 | 95% | - | - |
高岭土 | - | 94% | - |
矿物填料 | - | - | 96% |
通过将该组合与载体混合并且将混合物在适当的研磨机中研磨而获得即用型尘剂。这样的粉剂还可以用于种子的干拌种。
挤出机颗粒 | |
活性成分 | 15% |
木质素磺酸钠 | 2% |
羧甲基纤维素 | 1% |
高岭土 | 82% |
将该组合与这些佐剂混合并且研磨,并且将混合物用水湿润。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 | 8% |
聚乙二醇(分子量200) | 3% |
高岭土 | 89% |
将这种精细研磨的组合在混合器中均匀地施用于用聚乙二醇湿润的高岭土中。以此方式获得无尘的包衣的颗粒剂。
悬浮液浓缩物
将精细地研磨的组合与佐剂紧密地混合,得到悬浮液浓缩物,从该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。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、浇注或浸渍进行保护。
种子处理用的可流动性浓缩物
将精细地研磨的组合与佐剂紧密地混合,得到悬浮液浓缩物,从该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。使用这样的稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷洒、浇注或浸渍进行保护。
缓释的胶囊悬浮液
将28份的组合与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。向此乳液中加入在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加入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。将所得配制品作为适用于此目的装置中的水性悬浮液施用到种子上。
配制品类型包括乳液浓缩物(EC)、悬浮液浓缩物(SC)、悬乳液(SE)、胶囊悬浮液(CS)、水可分散性颗粒剂(WG)、可乳化性颗粒剂(EG)、油包水型乳液(EO)、水包油型乳液(EW)、微乳液(ME)、油分散体(OD)、油悬剂(OF)、油溶性液剂(OL)、可溶性浓缩物(SL)、超低容量悬浮液(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)、可溶性颗粒剂(SG)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。
制备实例:
“Mp”是指以℃计的熔点。自由基表示甲基基团。在Brucker400MHz光谱仪上记录1HNMR测量值,化学位移相对于TMS标准物以ppm给出。光谱在如指定的氘代溶剂中测量。以下任一种LCMS方法用于表征化合物。每种化合物获得的特征性LCMS值是保留时间(“Rt”,以分钟记录)和测得的分子离子(M+H)+。
LCMS和GCMS方法:
方法1:
在来自沃特世公司(Waters)的配备有电喷雾源(极性:正离子或负离子,毛细管:3.00kV,锥孔范围(Cone range):30V-60V,萃取器:2.00V,源温度:150℃,脱溶剂化温度:350℃,锥孔气体流量:0L/h,脱溶剂化气体流量:650L/h,质量范围:100Da至900Da)的质谱仪(ZQ单四极杆质谱仪)以及来自沃特世公司的以下Acquity UPLC上记录光谱:二元泵、加热柱室和二极管阵列检测器。溶剂脱气机、二元泵、加热柱室和二极管阵列检测器。柱:Waters UPLCHSS T3,1.8μm,30x 2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:0min 0%B,100%A;1.2-1.5min 100%B;流量(ml/min)0.85。
方法2:
在来自沃特世公司的配备有电喷雾源(极性:正离子或负离子,毛细管:3.00kV,锥孔范围:30V-60V,萃取器:2.00V,源温度:150℃,脱溶剂化温度:350℃,锥孔气体流量:0L/h,脱溶剂化气体流量:650L/h,质量范围:100Da至900Da)的质谱仪(SQD或ZQ单四极杆质谱仪)以及来自沃特世公司的以下Acquity UPLC上记录光谱:二元泵、加热柱室和二极管阵列检测器。溶剂脱气机、二元泵、加热柱室和二极管阵列检测器。柱:Waters UPLC HSS T3,1.8μm,30x 2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:0min 0%B,100%A;2.7-3.0min 100%B;流量(ml/min)0.85。
方法3:
在来自安捷伦科技公司(Agilent Technologies)的配备有电喷雾源(极性:正负极性开关,毛细管:4.00kV,碎裂器:100.00V,气体温度:350℃,气体流量:11L/min,雾化器气体:45psi,质量范围:110Da-1000Da,DAD波长范围:210nm-400nm)的质谱仪(6410三重四极杆质谱仪)上记录光谱。柱:KINETEX EVO C18,长度50mm,直径4.6mm,粒度2.6μm。柱温箱温度为40℃。溶剂梯度:A=含0.1%甲酸的水:乙腈(95:5v/v)。B=含0.1%甲酸的乙腈。梯度=0min 90%A,10%B;0.9-1.8min 0%A,100%B;2.2-2.5min 90%A,10%B。流量1.8mL/min。
方法4:
在来自沃特世公司的配备有电喷雾源(极性:正负极性开关,毛细管:3.00kV,锥孔电压:41.00V,源温度:150℃,脱溶剂化气体流量:1000L/h,脱溶剂化温度:500℃,锥孔气体流量:50L/h,质量范围:110Da-800Da,PDA波长范围:210nm-400nm)的质谱仪(Acquity SDS质谱仪)上记录光谱。柱:Acquity UPLC HSS T3C18,长度30mm,直径2.1mm,粒度1.8μm。柱温箱温度为40℃。溶剂梯度:A=含0.1%甲酸的水:乙腈(95:5v/v)。B=含0.05%甲酸的乙腈。梯度=0min 90%A,10%B;0.2min 50%A,50%B;0.7-1.3min0%A,100%B;1.4-1.6min90%A,10%B。流量0.8mL/min。
方法5:
在来自沃特世公司的配备有电喷雾源(极性:正离子或负离子,毛细管:2.50kV,锥孔电压:41V,萃取器:3.00V,源温度:150℃,脱溶剂化温度:500℃,锥孔气体流量:50L/h,脱溶剂化气体流量:1000L/h,质量范围:100Da至600Da)的质谱仪(SQ检测器2单四极杆质谱仪)以及来自沃特世公司的以下Acquity UPLC上记录光谱:四元泵、加热柱室和二极管阵列检测器。柱使用Waters UPLC HSST3,1.8μm,30x 2.1mm。柱温箱温度为40℃。DAD波长范围(nm):200至350。溶剂梯度:A=水+5%乙腈+0.05%HCOOH,B=乙腈+0.05%HCOOH。梯度=0min 90%A,10%B;0.2min 50%A,50%B;0.7-1.3min 0%A,100%B;1.4-1.6min 90%A,10%B。流量0.6mL/min。
a)具有式(I)的化合物的实例的制备:
实例P1:[5-乙基磺酰基-6-[7-(三氟甲基)咪唑并[1,2-c]嘧啶-2-基]-3-吡啶基]
亚氨基-二甲基-氧代-λ6-硫烷(化合物P1)的制备:
向氩气下的微波小瓶中的2-(5-氯-3-乙基磺酰基-2-吡啶基)-7-(三氟甲基)咪唑并[1,2-c]嘧啶(WO 16/071214)(0.4g,1.024mmol)的甲苯(8.2mL)溶液中添加(S)-(-)-BINAP(0.1971g,0.3071mmol)、碳酸铯(0.8338g,2.559mmol)、乙酸钯(II)(0.046g,0.2047mmol),接着添加亚氨基-二甲基-氧代-λ6-硫烷(0.2479g,2.661mmol)。将小瓶密封,并且将混合物在微波中在160℃下搅拌30分钟。经HYFLO过滤反应混合物,并且减压蒸发滤液。通过Combiflash在硅胶上(在二氯甲烷中0-5%的甲醇梯度)纯化残余物,并且合并含有产物的级分并浓缩。将残余物在乙醚中搅拌30分钟,过滤悬浮液,并且将固体真空干燥,以得到呈固体的[5-乙基磺酰基-6-[7-(三氟甲基)咪唑并[1,2-c]嘧啶-2-基]-3-吡啶基]亚氨基-二甲基-氧代-λ6-硫烷(化合物P1)(150mg),mp 241℃-243℃。LCMS(方法1):448(M+H)+,保留时间0.75min。
实例P2:[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-
吡啶基]亚氨基-二甲基-λ4-硫烷(化合物P17)的制备:
向氩气下的5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]吡啶-3-胺(WO 16/091731)(200mg,0.52mmol)和五氧化二磷(147mg,1.04mmol)在无水氯仿(5ml)中的悬浮液中滴加二甲基亚砜(142mg,0.13ml,1.82mmol)和三乙胺(55mg,76μl,0.54mmol)的混合物,同时保持内部温度低于35℃-40℃。将混合物在室温下搅拌过夜。将反应混合物小心倒入冰冷的NaOH水溶液(相对于五氧化二磷过量),同时保持内部温度低于10℃。将水相用氯仿萃取几次,将合并的有机层用水和盐水洗涤,经硫酸钠干燥,过滤并减压浓缩。通过Combiflash在硅胶上(5%的甲醇的乙酸乙酯溶液)纯化残余物,得到呈固体的[5-乙基磺酰基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]亚氨基-二甲基-λ4-硫烷(化合物P17)(108mg),mp 208℃-210℃。LCMS(方法1):446(M+H)+,保留时间0.66min。
表P:具有式(I)的化合物的实例
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b)具有式16、17、10、11、12和(XI-A,其中Rf是CF3)的中间体的制备:
实例P-I1:(Z)-6,6,6-三氟-5-羟基-1,1-二甲氧基-己-4-烯-3-酮(化合物16-A)
在室温下向经搅拌的4,4-二甲氧基丁-2-酮(47.39g)和三氟乙酸乙酯(76.54g)的混合物中滴加甲醇钠的甲醇溶液(25质量%,123mL)并继续在相同温度下搅拌6小时。然后将反应混合物冷却至10℃,并逐滴添加20%的H3PO4水溶液(150mL)直至pH~4。将反应混合物在水与乙酸乙酯之间分配,分离有机层。将水相用乙酸乙酯再萃取两次。将合并的有机层经硫酸钠干燥并减压浓缩,得到呈棕色油状物的(Z)-6,6,6-三氟-5-羟基-1,1-二甲氧基-己-4-烯-3-酮(16-A)(64.05g)。LCMS(方法5):227.26(M-H+),保留时间0.53min。
1H NMR(400MHz,CDCl3)δppm 5.98(s,1H),4.79(t,J=5.7Hz,1H),3.39-3.35(m,7H),2.76(d,J=5.6Hz,2H)。
实例P-I2:(Z)-4-氨基-1,1,1-三氟-6,6-二甲氧基-己-3-烯-2-酮(化合物17-A):
使用气态NH3吹扫经搅拌的(Z)-6,6,6-三氟-5-羟基-1,1-二甲氧基-己-4-烯-3-酮(16-A)(8.50g)的二噁烷溶液1小时。将容器密封并在40℃下加热8小时。然后将反应混合物冷却至室温并减压浓缩。通过快速色谱法纯化残余物,得到呈棕色油状物的(Z)-4-氨基-1,1,1-三氟-6,6-二甲氧基-己-3-烯-2-酮(17-A)(5.92g)。LCMS(方法5):226.28(M+H+),保留时间0.88min。
1H NMR(400MHz,DMSO-d6)δppm 2.60(d,J=5.8Hz,2H),3.26(s,6H),4.66(t,J=5.8Hz,1H),5.35(s,1H),8.93(br s,1H),9.88(brs,1H)。
实例P-I3:2-(三氟甲基)吡啶-4-胺(化合物10-A):
方法A:得自化合物(17-A)
向经搅拌的(Z)-4-氨基-1,1,1-三氟-6,6-二甲氧基-己-3-烯-2-酮(17-A)(4.34g)的乙腈溶液中添加NH4OAc(7.35g)然后添加乙酸(3.1mL)。将容器密封并在150℃下加热8小时。然后将反应混合物冷却至室温,用水稀释并用CH2Cl2萃取两次。将合并的有机层用盐水洗涤,经硫酸钠干燥并减压浓缩。通过快速色谱法纯化粗产物,得到呈淡黄色油状物的2-(三氟甲基)吡啶-4-胺(10-A)(1.86g)。LCMS(方法5):163.24(M+H+),保留时间0.19min。
1H NMR(400MHz,DMSO-d6)δ6.56(br.s.,2H)6.65(dd,J=5.6,1.96Hz,1H)6.89(d,J=2.1Hz,1H)8.09(d,J=5.6Hz,1H)。
方法B:经由Smiles重排
在室温下向经搅拌的2-(三氟甲基)吡啶-4-醇(4.7g)的N,N-二甲基乙酰胺(50mL)溶液中添加碳酸钾(9.96g),然后添加2-氯-乙酰胺(3.23g)。将反应混合物加热至90℃并在相同温度下继续搅拌3小时。将反应温度进一步升至150℃并在相同温度下搅拌3小时。将反应混合物在水与叔丁基甲醚TBME之间分配。分离有机层,将水层用TBME再萃取两次。将合并的有机层用盐水洗涤,经硫酸钠干燥并减压浓缩,得到呈淡黄色油状物的2-(三氟甲基)吡啶-4-胺(10-A)(3.97g)。
用方法B生成的样品显示出与用方法A产生的样品相同的分析数据。
方法C:来自化合物(12-A)
向经搅拌的4-氯-2-(三氟甲基)吡啶(12-A)(0.180g)在DMSO(2mL)中的悬浮液中添加CuI(0.038g),然后添加L-脯氨酸(0.0461g)、碳酸钾(0.208g)和氢氧化铵(25%,1.39g)。将反应容器密封并在100℃下加热5小时。将反应混合物在TBME与饱和NaHCO3水溶液之间分配。分离有机层,将水层用TBME再萃取。将合并的有机层用盐水洗涤,经硫酸钠干燥并减压浓缩。通过快速色谱法纯化残余物,得到呈淡黄色油状物的2-(三氟甲基)吡啶-4-胺(10-A)。
用方法C生成的样品显示出与用方法A产生的样品相同的分析数据。
方法D:来自化合物(16-A)
使用气态NH3将经搅拌的(Z)-6,6,6-三氟-5-羟基-1,1-二甲氧基-己-4-烯-3-酮(16-A)(0.90g)的丙腈溶液饱和1小时。密封反应容器并在50℃下加热6小时。然后将反应混合物冷却至室温,添加NH4OAc(0.94g),然后添加乙酸(0.71g)。将容器密封并在150℃下加热8小时。关闭反应容器并在150℃下加热6小时。然后将反应混合物冷却至室温,用水稀释并用CH2Cl2萃取两次。将合并的有机层用盐水洗涤,经硫酸钠干燥并减压浓缩。通过快速色谱法纯化粗产物,得到呈淡黄色油状物的2-(三氟甲基)吡啶-4-胺(10-A)(0.315g)。
用方法D生成的样品显示出与用方法A产生的样品相同的分析数据。
实例P-I4:5-溴-2-(三氟甲基)吡啶-4-胺(化合物11-A):
向经搅拌的2-(三氟甲基)吡啶-4-胺(10-A)(4.84g)的乙酸(50mL)溶液中添加溴化铵(3.77g),并将混合物加热至70℃。在70℃下经1小时向反应混合物中滴加过氧化氢(30%的水溶液,4.58mL),并在相同温度下继续加热1小时。将反应混合物冷却至室温并小心地倒到10%的亚硫酸氢钠水溶液(150mL)上。沉淀出固体,将其滤出并干燥,得到呈白色固体的5-溴-2-(三氟甲基)吡啶-4-胺(11-A)(5.59g)。LCMS(方法5):241.06(M+H+),保留时间0.77min。
1H NMR(400MHz,CDCl3)δppm 6.96(s,1H)8.43-8.51(m,1H)。
实例P-I5:N3-甲基-6-(三氟甲基)吡啶-3,4-二胺(化合物XI-A,其中Rf是CF3):
(XI-A,其中Rf是CF3)
向经搅拌的5-溴-2-(三氟甲基)吡啶-4-胺(11-A)(1.89g)和甲胺MeNH2(40%水溶液,10.2mL)在水中的悬浮液中添加CuI(0.076g),随后添加1-(2-吡啶基)乙酮肟(0.0678g)。密封反应容器并在85℃下加热6小时。将反应混合物在TBME与饱和NaHCO3水溶液之间分配。分离有机层,将水层用TBME再萃取。将合并的有机层用盐水洗涤,经硫酸钠干燥并减压浓缩。通过快速色谱法纯化残余物,得到呈白色固体的N3-甲基-6-(三氟甲基)吡啶-3,4-二胺(XI-A,其中Rf是CF3)(1.10g),mp 138℃-140℃。LCMS(方法5):192.33(M+H+),保留时间0.15min。
1H NMR(400MHz,DMSO-d6)δppm 2.80(d,J=4.9Hz,3H)5.22(br d,J=5.0Hz,1H)5.82(s,2H)6.84(s,1H)7.58(s,1H)。
实例P-I6:4-氯-2-(三氟甲基)吡啶(化合物12-A):
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在25℃下经5分钟向经搅拌的2-(三氟甲基)吡啶-4-醇(9.4g)在50mL环己烷和一滴DMF中的溶液中滴加乙二酰氯(2.6当量)。添加后,将反应混合物加热至80℃保持3小时。将反应混合物冷却至室温,然后滴加50mL水。将水相用3x 100mL TBME萃取。将合并的TBME层用70ml饱和碳酸氢钠水溶液洗涤。将有机层经硫酸钠干燥并减压浓缩,得到呈黄色液体的4-氯-2-(三氟甲基)吡啶(12-A)(7.31g)。LCMS(方法5):192(M+H+),保留时间0.96min。
1H NMR(400MHz,CDCl3)δppm 7.51(dd,J=5.2,1.5Hz,1H)7.71(d,J=1.6Hz,1H)8.64(d,J=5.3Hz,1H)。
通过加入其他具有杀昆虫、杀螨和/或杀真菌活性的成分,根据本发明的组合物的活性可以显著地加宽,并且适合于普遍情况。具有式I的化合物与其他具有杀昆虫、杀螨和/或杀真菌活性的成分的混合物还可以具有另外的意料之外的优点,这些优点还可以在更宽的意义上描述为协同活性。例如,植物对其更好的耐受性、降低的植物毒性、昆虫可以在它们的不同发育阶段得到控制、或者在它们的生产期间(例如,在研磨或者混合过程中,在它们的储藏或它们的使用过程中)更好的行为。
在这里,添加的适当活性成分的代表是以下类别的活性成分:有机磷化合物、硝基酚衍生物、硫脲、保幼激素、甲脒、二苯甲酮衍生物、脲、吡咯衍生物、氨基甲酸酯、拟除虫菊酯、氯化烃、酰基脲、吡啶基亚甲基氨基衍生物、大环内酯、新烟碱和苏云金芽孢杆菌制剂。
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”表示“选自由本发明的表1至9和表P中所述的化合物组成的组的一种化合物”):
一种佐剂,该佐剂选自由以下物质组成的组:石油(别名)(628)+TX,
一种杀螨剂,该杀螨剂选自由以下物质组成的组:1,1-双(4-氯苯基)-2-乙氧基乙醇(IUPAC名称)(910)+TX、2,4-二氯苯基苯磺酸盐(IUPAC/化学文摘名称)(1059)+TX、2-氟-N-甲基-N-1-萘基乙酰胺(IUPAC名称)(1295)+TX、4-氯苯基苯基砜(IUPAC名称)(981)+TX、阿维菌素(1)+TX、灭螨醌(3)+TX、乙酰虫腈[CCN]+TX、氟丙菊酯(9)+TX、涕灭威(16)+TX、涕灭砜威(863)+TX、α-氯氰菊酯(202)+TX、赛果(870)+TX、磺胺螨酯[CCN]+TX、果满磷(872)+TX、胺吸磷(875)+TX、胺吸磷草酸氢盐(875)+TX、双甲脒(24)+TX、杀螨特(881)+TX、三氧化二砷(882)+TX、AVI 382(化合物代码)+TX、AZ 60541(化合物代码)+TX、乙基谷硫磷(44)+TX、甲基谷硫磷(45)+TX、偶氮苯(IUPAC名称)(888)+TX、三唑锡(46)+TX、偶氮磷(889)+TX、苯菌灵(62)+TX、苯噁磷(别名)[CCN]+TX、苯螨特(71)+TX、苯甲酸苄酯(IUPAC名称)[CCN]+TX、联苯肼酯(74)+TX、联苯菊酯(76)+TX、乐杀螨(907)+TX、溴灭菊酯(别名)+TX、溴烯杀(918)+TX、溴硫磷(920)+TX、乙基溴硫磷(921)+TX、溴螨酯(94)+TX、稻虱净(99)+TX、丁酮威(103)+TX、丁酮砜威(104)+TX、丁基哒螨灵(别名)+TX、多硫化钙(IUPAC名称)(111)+TX、毒杀芬(941)+TX、氯灭杀威(943)+TX、西维因(115)+TX、卡巴呋喃(118)+TX、三硫磷(947)+TX、CGA 50’439(开发代码)(125)+TX、灭螨猛(126)+TX、氯杀螨(959)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、溴虫腈(130)+TX、杀螨醇(968)+TX、杀螨酯(970)+TX、敌螨丹(971)+TX、毒虫畏(131)+TX、克氯苯(975)+TX、灭螨眯(977)+TX、灭虫脲(978)+TX、丙酯杀螨醇(983)+TX、毒死蜱(145)+TX、甲基毒死蜱(146)+TX、虫螨磷(994)+TX、瓜菊酯I(696)+TX、瓜菊酯II(696)+TX、瓜菊酯(696)+TX、四螨嗪(158)+TX、氯氰碘柳胺(别名)[CCN]+TX、蝇毒磷(174)+TX、克罗米通(别名)[CCN]+TX、丁烯磷(1010)+TX、硫杂灵(1013)+TX、果虫磷(1020)+TX、丁氟螨酯(CAS登记号:400882-07-7)+TX、三氟氯氰菊酯(196)+TX、三环锡(199)+TX、氯氰菊酯(201)+TX、DCPM(1032)+TX、DDT(219)+TX、田乐磷(1037)+TX、田乐磷-O(1037)+TX、田乐磷-S(1037)+TX、内吸磷(1038)+TX、内吸磷甲基(224)+TX、内吸磷-O(1038)+TX、内吸磷-O-甲基(224)+TX、内吸磷-S(1038)+TX、内吸磷-S-甲基(224)+TX、内吸磷-S-甲基砜(1039)+TX、丁醚脲(226)+TX、氯亚胺硫磷(1042)+TX、二嗪农(227)+TX、抑菌灵(230)+TX、敌敌畏(236)+TX、二克磷(dicliphos)(别名)+TX、开乐散(242)+TX、百治磷(243)+TX、除螨灵(1071)+TX、甲氟磷(1081)+TX、乐果(262)+TX、二活菌素(别名)(653)+TX、消螨酚(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、消螨通(269)+TX、敌螨普(270)+TX、敌螨普-4[CCN]+TX、敌螨普-6[CCN]+TX、邻敌螨消(1090)+TX、硝戊酯(1092)+TX、硝辛酯(1097)+TX、硝丁酯(1098)+TX、敌杀磷(1102)+TX、二苯砜(IUPAC名称)(1103)+TX、戒酒硫(别名)[CCN]+TX、乙拌磷(278)+TX、DNOC(282)+TX、苯氧炔螨(1113)+TX、多拉菌素(别名)[CCN]+TX、硫丹(294)+TX、因毒磷(1121)+TX、EPN(297)+TX、依立诺克丁(别名)[CCN]+TX、乙硫磷(309)+TX、益果(1134)+TX、乙螨唑(320)+TX、乙嘧硫磷(1142)+TX、抗螨唑(1147)+TX、喹螨醚(328)+TX、苯丁锡(330)+TX、苯硫威(337)+TX、甲氰菊酯(342)+TX、吡螨胺(别名)+TX、唑螨酯(345)+TX、除螨酯(1157)+TX、芳氟胺(1161)+TX、氰戊菊酯(349)+TX、氟虫腈(354)+TX、嘧螨酯(360)+TX、啶蜱脲(1166)+TX、氟螨噻(1167)+TX、氟环脲(366)+TX、氟氰戊菊酯(367)+TX、联氟螨(1169)+TX、氟虫脲(370)+TX、氟氯苯菊酯(372)+TX、氟杀螨(1174)+TX、氟胺氰菊酯(1184)+TX、FMC 1137(开发代码)(1185)+TX、杀螨脒(405)+TX、杀螨脒盐酸盐(405)+TX、安果(1192)+TX、胺甲威(1193)+TX、γ-HCH(430)+TX、果绿定(1205)+TX、苄螨醚(424)+TX、庚烯磷(432)+TX、十六烷基环丙烷甲酸酯(IUPAC/化学文摘名称)(1216)+TX、噻螨酮(441)+TX、碘甲烷(IUPAC名称)(542)+TX、水胺硫磷(别名)(473)+TX、异丙基O-(甲氧基氨基硫代磷酰基)水杨酸盐(IUPAC名称)(473)+TX、伊佛霉素(别名)[CCN]+TX、茉莉菊酯I(696)+TX、茉莉菊酯II(696)+TX、碘硫磷(1248)+TX、灵丹(430)+TX、氯芬奴隆(490)+TX、马拉硫磷(492)+TX、丙螨氰(1254)+TX、灭蚜磷(502)+TX、地胺磷(1261)+TX、甲硫芬(别名)[CCN]+TX、虫螨畏(1266)+TX、甲胺磷(527)+TX、杀扑磷(529)+TX、灭虫威(530)+TX、灭多虫(531)+TX、甲基溴(537)+TX、速灭威(550)+TX、速灭磷(556)+TX、兹克威(1290)+TX、密灭汀(557)+TX、米尔贝肟(别名)[CCN]+TX、丙胺氟(1293)+TX、久效磷(561)+TX、茂果(1300)+TX、莫昔克丁(别名)[CCN]+TX、二溴磷(567)+TX、NC-184(化合物代码)+TX、NC-512(化合物代码)+TX、氟蚁灵(1309)+TX、日光霉素(nikkomycins)(别名)[CCN]+TX、戊氰威(1313)+TX、戊氰威1:1氯化锌络合物(1313)+TX、NNI-0101(化合物代码)+TX、NNI-0250(化合物代码)+TX、氧化乐果(594)+TX、草氨酰(602)+TX、异亚砜磷(1324)+TX、砜拌磷(1325)+TX、pp'-DDT(219)+TX、对硫磷(615)+TX、苄氯菊酯(626)+TX、石油(别名)(628)+TX、芬硫磷(1330)+TX、稻丰散(631)+TX、甲拌磷(636)+TX、伏杀磷(637)+TX、硫环磷(1338)+TX、亚胺硫磷(638)+TX、磷胺(639)+TX、辛硫磷(642)+TX、甲基嘧啶磷(652)+TX、聚氯萜烯(传统名称)(1347)+TX、浏阳霉素(653)+TX、丙氯醇(1350)+TX、丙溴磷(662)+TX、蜱虱威(1354)+TX、克螨特(671)+TX、巴胺磷(673)+TX、残杀威(678)+TX、乙噻唑磷(1360)+TX、发硫磷(1362)+TX、除虫菊酯I(696)+TX、除虫菊酯II(696)+TX、除虫菊酯(696)+TX、哒螨灵(699)+TX、哒嗪硫磷(701)+TX、嘧螨醚(706)+TX、嘧硫磷(1370)+TX、喹硫磷(quinalphos)(711)+TX、喹硫磷(quintiofos)(1381)+TX、R-1492(开发代码)(1382)+TX、RA-17(开发代码)(1383)+TX、鱼藤酮(722)+TX、八甲磷(1389)+TX、克线丹(别名)+TX、司拉克丁(别名)[CCN]+TX、SI-0009(化合物代码)+TX、苏硫磷(1402)+TX、螺螨酯(738)+TX、螺甲螨酯(739)+TX、SSI-121(开发代码)(1404)+TX、舒非仑(别名)[CCN]+TX、氟虫胺(750)+TX、治螟磷(753)+TX、硫磺(754)+TX、SZI-121(开发代码)(757)+TX、τ-氟胺氰菊酯(398)+TX、吡螨胺(763)+TX、TEPP(1417)+TX、叔丁威(别名)+TX、杀虫畏(777)+TX、四氯杀螨砜(786)+TX、杀螨素(别名)(653)+TX、杀螨好(1425)+TX、噻芬诺(别名)+TX、抗虫威(1431)+TX、久效威(800)+TX、甲基乙拌磷(801)+TX、克杀螨(1436)+TX、苏云金素(别名)[CCN]+TX、威菌磷(1441)+TX、苯螨噻(1443)+TX、三唑磷(820)+TX、唑蚜威(triazuron)(别名)+TX、敌百虫(824)+TX、三氯丙氧磷(1455)+TX、三活菌素(别名)(653)+TX、蚜灭多(847)+TX、氟吡唑虫(vaniliprole)[CCN]和YI-5302(化合物代码)+TX,
杀藻剂,该杀藻剂选自由以下组成的物质组:3-苯并[b]噻吩-2-基-5,6-二氢-1,4,2-噁噻嗪-4-氧化物[CCN]+TX、二辛酸铜(IUPAC名称)(170)+TX、硫酸铜(172)+TX、cybutryne[CCN]+TX、二氢萘醌(dichlone)(1052)+TX、双氯酚(232)+TX、茵多酸(295)+TX、三苯锡(fentin)(347)+TX、熟石灰[CCN]+TX、代森钠(nabam)(566)+TX、灭藻醌(quinoclamine)(714)+TX、醌萍胺(quinonamid)(1379)+TX、西玛津(730)+TX、三苯锡乙酸盐(IUPAC名称)(347)和氢氧化三苯锡(IUPAC名称)(347)+TX,
一种驱蠕虫剂,该驱蠕虫剂选自由以下物质组成的组:阿维菌素(1)+TX、育畜磷(1011)+TX、多拉菌素(别名)[CCN]+TX、埃玛菌素(291)+TX、埃玛菌素苯甲酸酯(291)+TX、依立诺克丁(别名)[CCN]+TX、伊维菌素(别名)[CCN]+TX、米尔贝肟(别名)[CCN]+TX、莫昔克丁(别名)[CCN]+TX、胡椒嗪(别名)[CCN]+TX、司拉克丁(别名)[CCN]+TX、多杀菌素(737)和托布津(thiophanate)(1435)+TX,
杀鸟剂,该杀鸟剂选自由以下组成的物质组:氯醛糖(127)+TX、异狄氏剂(1122)+TX、倍硫磷(346)+TX、吡啶-4-胺(IUPAC名称)(23)和士的宁(745)+TX,
一种杀细菌剂,该杀细菌剂选自由以下物质组成的组:1-羟基-1H-吡啶-2-硫酮(IUPAC名称)(1222)+TX、4-(喹喔啉-2-基氨基)苯磺酰胺(IUPAC名称)(748)+TX、8-羟基喹啉硫酸盐(446)+TX、溴硝醇(97)+TX、二辛酸铜(IUPAC名称)(170)+TX、氢氧化铜(IUPAC名称)(169)+TX、甲酚[CCN]+TX、双氯酚(232)+TX、双硫氧吡啶(1105)+TX、多地辛(1112)+TX、敌磺钠(fenaminosulf)(1144)+TX、甲醛(404)+TX、汞加芬(别名)[CCN]+TX、春雷霉素(483)+TX、春雷霉素盐酸盐水合物(483)+TX、二(二甲基二硫代氨基甲酸盐)镍(IUPAC名称)(1308)+TX、三氯甲基吡啶(nitrapyrin)(580)+TX、辛噻酮(octhilinone)(590)+TX、奥索利酸(606)+TX、土霉素(611)+TX、羟基喹啉硫酸钾(446)+TX、烯丙苯噻唑(probenazole)(658)+TX、链霉素(744)+TX、链霉素倍半硫酸盐(744)+TX、叶枯酞(766)+TX和硫柳汞(别名)[CCN]+TX,
一种生物剂,该生物剂选自由以下物质构成的组:棉褐带卷蛾颗粒体病毒(Adoxophyes orana GV)(12)+TX、放射形土壤杆菌(Agrobacterium radiobacter)(别名)(13)+TX、捕食螨(Amblyseius spp.)(别名)(19)+TX、斧菜夜蛾核多角体病毒(Anagraphafalcifera NPV)(别名)(28)+TX、原缨翅缨小蜂(Anagrus atomus)(别名)(29)+TX、短距虫牙小蜂(Aphelinus abdominalis)(别名)(33)+TX、棉虫牙寄生蜂(Aphidius colemani)(别名)(34)+TX、食蚜癭蚊(Aphidoletes aphidimyza)(别名)(35)+TX、苜蓿银纹夜蛾核多角体病毒(Autographa californica NPV)(别名)(38)+TX、坚硬芽孢杆菌(Bacillus firmus)(别名)(48)+TX、球形芽孢杆菌(Bacillus sphaericus Neide)(学名)(49)+TX、苏云金芽孢杆菌(Bacillus thuringiensis Berliner)(学名)(51)+TX、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensis subsp.aizawai)(学名)(51)+TX、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensis subsp.israelensis)(学名)(51)+TX、苏云金芽孢杆菌日本亚种(Bacillus thuringiensis subsp.japonensis)(学名)(51)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subsp.kurstaki)(学名)(51)+TX、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subsp.tenebrionis)(学名)(51)+TX、球孢白僵菌(Beauveria bassiana)(别名)(53)+TX、布氏白僵菌(Beauveria brongniartii)(别名)(54)+TX、普通草蛉(Chrysoperla carnea)(别名)(151)+TX、孟氏隐唇票瓜虫(Cryptolaemus montrouzieri)(178)+TX、苹果蠢蛾颗粒体病毒(Cydia pomonella GV)(别名)(191)+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)(别名)(212)+TX、碗豆潜叶蝇姬小蜂(Diglyphus isaea)(别名)(254)+TX、丽蚜小蜂(Encarsia formosa)(学名)(293)+TX、奖角蚜小蜂(Eretmocerus eremicus)(别名)(300)+TX、玉米穆夜蛾核多角体病毒(Helicoverpazea NPV)(431)+TX、嗜菌异小杆线虫(Heterorhabditis bacteriophora)和大异小杆线虫(H.megidis)(别名)(433)+TX、会聚长足瓢虫(Hippodamia convergens)(别名)(442)+TX、橘粉介壳虫寄生蜂(Leptomastix dactylopii)(别名)(488)+TX、盲畴(Macrolophuscaliginosus)(别名)(491)+TX、甘蓝夜蛾核多角体病毒(Mamestra brassicae NPV)(494)+TX、黄阔柄跳小蜂(Metaphycus helvolus)(别名)(522)+TX、金龟子绿僵菌蝗变种(Metarhizium anisopliae var.acridum)(学名)(523)+TX、金龟子绿僵菌小孢变种(Metarhizium anisopliae var.anisopliae)(学名)(523)+TX、松黄叶蜂核多角体病毒(Neodiprion sertifer NPV)和红头松树叶蜂核多角体病毒(N.lecontei NPV)(别名)(575)+TX、小花畴(Orius spp.)(别名)(596)+TX、玫烟色拟青霉(Paecilomycesfumosoroseus)(别名)(613)+TX、智利捕植螨(Phytoseiulus persimilis)(别名)(644)+TX、甜菜夜蛾(Spodoptera exigua)多核衣壳核多角体病毒(学名)(741)+TX、毛蚊线虫(Steinernema bibionis)(别名)(742)+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)(别名)(742)+TX、夜蛾斯氏线虫(Steinernema feltiae)(别名)(742)+TX、格氏斯氏线虫(Steinernema glaseri)(别名)(742)+TX、Steinernema riobrave(别名)(742)+TX、Steinernema riobravis(别名)(742)+TX、蝼蛄斯氏线虫(Steinernema scapterisci)(别名)(742)+TX、斯万氏线虫属(Steinernema spp.)(别名)(742)+TX、赤眼蜂属(Trichogramma spp.)(别名)(826)+TX、西方盲走螨(Typhlodromus occidentalis)(别名)(844)和蜡蚧轮枝菌(Verticillium lecanii)(848)+TX,
土壤消毒剂,该土壤消毒剂选自由以下组成的物质组:碘甲烷(IUPAC名称)(542)和甲基溴(537)+TX,
一种化学不育剂,该化学不育剂选自由以下物质组成的组:唑磷嗪(apholate)[CCN]+TX、双(氮丙啶)甲氨基膦硫化物(bisazir)(别名)[CCN]+TX、白消安(别名)[CCN]+TX、除虫脲(250)+TX、迪麦替夫(dimatif)(别名)[CCN]+TX、六甲蜜胺(hemel)[CCN]+TX、六甲磷(hempa)[CCN]+TX、甲基涕巴(metepa)[CCN]+TX、甲硫涕巴(methiotepa)[CCN]+TX、不育特(methyl apholate)[CCN]+TX、不孕啶(morzid)[CCN]+TX、氟幼脲(penfluron)(别名)[CCN]+TX、涕巴(tepa)[CCN]+TX、硫代六甲磷(thiohempa)(别名)[CCN]+TX、噻替派(别名)[CCN]+TX、曲他胺(别名)[CCN]和尿烷亚胺(别名)[CCN]+TX,
一种昆虫信息素,该昆虫信息素选自由以下物质组成的组:(E)-癸-5-烯-1-基乙酸酯与(E)-癸-5-烯-1-醇(IUPAC名称)(222)+TX、(E)-十三碳-4-烯-1-基乙酸酯(IUPAC名称)(829)+TX、(E)-6-甲基庚-2-烯-4-醇(IUPAC名称)(541)+TX、(E,Z)-十四碳-4,10-二烯-1-基乙酸酯(IUPAC名称)(779)+TX、(Z)-十二碳-7-烯-1-基乙酸酯(IUPAC名称)(285)+TX、(Z)-十六碳-11-烯醛(IUPAC名称)(436)+TX、(Z)-十六碳-11-烯-1-基乙酸酯(IUPAC名称)(437)+TX、(Z)-十六碳-13-烯-11-炔-1-基乙酸酯(IUPAC名称)(438)+TX、(Z)-二十-13-烯-10-酮(IUPAC名称)(448)+TX、(Z)-十四碳-7-烯-1-醛(IUPAC名称)(782)+TX、(Z)-十四碳-9-烯-1-醇(IUPAC名称)(783)+TX、(Z)-十四碳-9-烯-1-基乙酸酯(IUPAC名称)(784)+TX、(7E,9Z)-十二碳-7,9-二烯-1-基乙酸酯(IUPAC名称)(283)+TX、(9Z,11E)-十四碳-9,11-二烯-1-基乙酸酯(IUPAC名称)(780)+TX、(9Z,12E)-十四碳-9,12-二烯-1-基乙酸酯(IUPAC名称)(781)+TX、14-甲基十八-1-烯(IUPAC名称)(545)+TX、4-甲基壬醛-5-醇与4-甲基壬醛-5-酮(IUPAC名称)(544)+TX、α-多纹素(multistriatin)(别名)[CCN]+TX、小蠹性信息素(别名)[CCN]+TX、十二碳烯醇(别名)[CCN]+TX、十二碳二烯醇(别名)(167)+TX、诱蝇酮(别名)(179)+TX、环氧十九烷(disparlure)(277)+TX、十二碳-8-烯-1基乙酸酯(IUPAC名称)(286)+TX、十二碳-9-烯-1-基乙酸酯(IUPAC名称)(287)+TX、十二碳-8+TX、10-二烯-1-基乙酸酯(IUPAC名称)(284)+TX、多米尼卡引诱剂(dominicalure)(别名)[CCN]+TX、4-甲基辛酸乙酯(IUPAC名称)(317)+TX、丁香酚(别名)[CCN]+TX、南部松小蠹诱剂(frontalin)(别名)[CCN]+TX、诱虫十六酯(gossyplure)(别名)(420)+TX、诱杀烯混剂(grandlure)(421)+TX、诱杀烯混剂I(别名)(421)+TX、诱杀烯混剂II(别名)(421)+TX、诱杀烯混剂III(别名)(421)+TX、诱杀烯混剂IV(别名)(421)+TX、己诱剂[CCN]+TX、齿小蠹二烯醇(别名)[CCN]+TX、小蠢烯醇(别名)[CCN]+TX、金龟子性诱剂(japonilure)(别名)(481)+TX、三甲基二氧三环壬烷(lineatin)(别名)[CCN]+TX、夜蛾诱剂(litlure)(别名)[CCN]+TX、粉纹夜蛾性诱剂(looplure)(别名)[CCN]+TX、诱杀酯[CCN]+TX、美加特酸(megatomoic acid)(别名)[CCN]+TX、诱虫醚(别名)(540)+TX、诱虫烯(563)+TX、十八-2,13-二烯-1-基乙酸酯(IUPAC名称)(588)+TX、十八-3,13-二烯-1-基乙酸酯(IUPAC名称)(589)+TX、梨小食心虫性信息素(orfralure)(别名)[CCN]+TX、椰蛀犀金龟聚集信息素(oryctalure)(别名)(317)+TX、非乐康(ostramone)(别名)[CCN]+TX、诱虫环[CCN]+TX、索迪叮(sordidin)(别名)(736)+TX、食菌甲诱醇(别名)[CCN]+TX、十四-11-烯-1-基乙酸酯(IUPAC名称)(785)+TX、特诱酮(839)+TX、特诱酮A(别名)(839)+TX、特诱酮B1(别名)(839)+TX、特诱酮B2(别名)(839)+TX、特诱酮C(别名)(839)和创科尔(trunc-call)(别名)[CCN]+TX,
昆虫驱避剂,该昆虫驱避剂选自由以下组成的物质组:2-(辛基硫代)乙醇(IUPAC名称)(591)+TX、避蚊酮(butopyronoxyl)(933)+TX、丁氧基(聚丙二醇)(936)+TX、己二酸二丁酯(IUPAC名称)(1046)+TX、邻苯二甲酸二丁酯(1047)+TX、丁二酸二丁酯(IUPAC名称)(1048)+TX、避蚊胺[CCN]+TX、避蚊胺[CCN]+TX、驱蚊酯(dimethyl carbate)[CCN]+TX、乙基己二醇(1137)+TX、己脲[CCN]+TX、甲喹丁(methoquin-butyl)(1276)+TX、甲基新癸酰胺[CCN]+TX、氨羰基甲酸酯(oxamate)[CCN]和羟哌酯[CCN]+TX,
一种杀昆虫剂,该杀昆虫剂选自由以下物质组成的组:1-二氯-1-硝基乙烷(IUPAC/化学文摘名称)(1058)+TX、1,1-二氯-2,2-双(4-乙基苯基)乙烷(IUPAC名称)(1056)+TX、1,2-二氯丙烷(IUPAC/化学文摘名称)(1062)+TX、1,2-二氯丙烷与1,3-二氯丙烯(IUPAC名称)(1063)+TX、1-溴-2-氯乙烷(IUPAC/化学文摘名称)(916)+TX、2,2,2-三氯-1-(3,4-二氯苯基)乙基乙酸酯(IUPAC名称)(1451)+TX、2,2-二氯乙烯基2-乙基亚磺酰基乙基甲基磷酸盐(IUPAC名称)(1066)+TX、2-(1,3-二四氢噻吩-2-基)苯基二甲基氨基甲酸酯(IUPAC/化学文摘名称)(1109)+TX、2-(2-丁氧基乙氧基)乙基硫氰酸酯(IUPAC/化学文摘名称)(935)+TX、2-(4,5-二甲基-1,3-二氧戊环-2-基)苯基甲基氨基甲酸酯(IUPAC/化学文摘名称)(1084)+TX、2-(4-氯-3,5-二甲苯基氧基)乙醇(IUPAC名称)(986)+TX、2-氯乙烯基二乙基磷酸酯(IUPAC名称)(984)+TX、2-咪唑烷酮(IUPAC名称)(1225)+TX、2-异戊酰茚满-1,3-二酮(IUPAC名称)(1246)+TX、2-甲基(丙-2-炔基)氨基苯基甲基氨基甲酸酯(IUPAC名称)(1284)+TX、2-硫代氰酰乙基十二酸酯(IUPAC名称)(1433)+TX、3-溴-1-氯丙-1-烯(IUPAC名称)(917)+TX、3-甲基-1-苯基吡唑-5-基二甲基氨基甲酸酯(IUPAC名称)(1283)+TX、4-甲基(丙-2-炔基)氨基-3,5-二甲苯基甲基氨基甲酸酯(IUPAC名称)(1285)+TX、5,5-二甲基-3-氧代环己-1-烯基二甲基氨基甲酸酯(IUPAC名称)(1085)+TX、阿维菌素(1)+TX、高灭磷(2)+TX、啶虫脒(4)+TX、家蝇磷(别名)[CCN]+TX、乙酰虫腈[CCN]+TX、氟丙菊酯(9)+TX、丙烯腈(IUPAC名称)(861)+TX、棉铃威(15)+TX、涕灭威(16)+TX、涕灭砜威(863)+TX、艾氏剂(864)+TX、丙烯菊酯(17)+TX、阿洛氨菌素(别名)[CCN]+TX、除害威杀虫剂(866)+TX、α-氯氰菊酯(202)+TX、α-蜕化素(别名)[CCN]+TX、磷化铝(640)+TX、赛果(870)+TX、果满磷(872)+TX、灭害威(873)+TX、胺吸磷(875)+TX、胺吸磷草酸氢盐(875)+TX、双甲脒(24)+TX、新烟碱(877)+TX、乙基杀扑磷(883)+TX、AVI 382(化合物代码)+TX、AZ 60541(化合物代码)+TX、印楝素(别名)(41)+TX、甲基吡噁磷(42)+TX、乙基谷硫磷(44)+TX、甲基谷硫磷(45)+TX、偶氮磷(889)+TX、苏云金芽孢杆菌δ内毒素(别名)(52)+TX、氟硅酸钡(别名)[CCN]+TX、多硫化钡(IUPAC/化学文摘名称)(892)+TX、熏菊酯[CCN]+TX、拜耳22/190(开发代码)(893)+TX、拜耳22408(开发代码)(894)+TX、噁虫威(58)+TX、丙硫克百威(60)+TX、杀虫磺(66)+TX、β-氟氯氰菊酯(194)+TX、β-氯氰菊酯(203)+TX、联苯菊酯(76)+TX、生物丙烯菊酯(78)+TX、生物丙烯菊酯S-环戊烯基同分异构体(别名)(79)+TX、生物乙菊酯(bioethanomethrin)[CCN]+TX、生物氯菊酯(biopermethrin)(908)+TX、菊精(80)+TX、双(2-氯乙基)醚(IUPAC名称)(909)+TX、双三氟虫脲(83)+TX、硼砂(86)+TX、溴灭菊酯(别名)+TX、溴苯烯磷(914)+TX、溴烯杀(918)+TX、溴-DDT(别名)[CCN]+TX、溴硫磷(920)+TX、乙基溴硫磷(921)+TX、合杀威(924)+TX、稻虱净(99)+TX、畜虫威(926)+TX、特嘧硫磷(butathiofos)(927)+TX、丁酮威(103)+TX、丁酯磷(932)+TX、丁酮砜威(104)+TX、丁基哒螨灵(别名)+TX、硫线磷(109)+TX、砷酸钙[CCN]+TX、氰化钙(444)+TX、多硫化钙(IUPAC名称)(111)+TX、毒杀芬(941)+TX、氯灭杀威(943)+TX、胺甲萘(115)+TX、卡巴呋喃(118)+TX、二硫化碳(IUPAC/化学文摘名称)(945)+TX、四氯化碳(IUPAC名称)(946)+TX、三硫磷(947)+TX、丁硫克百威(119)+TX、杀螟丹(123)+TX、杀螟丹盐酸盐(123)+TX、瑟瓦定(别名)(725)+TX、冰片丹(960)+TX、氯丹(128)+TX、十氯酮(963)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、氯氧磷(129)+TX、溴虫腈(130)+TX、毒虫畏(131)+TX、定虫隆(132)+TX、氯甲磷(136)+TX、氯仿[CCN]+TX、三氯硝基甲烷(141)+TX、氯腈肟磷(989)+TX、灭虫吡啶(chlorprazophos)(990)+TX、毒死蜱(145)+TX、甲基毒死蜱(146)+TX、虫螨磷(994)+TX、环虫酰肼(150)+TX、瓜菊酯I(696)+TX、瓜菊酯II(696)+TX、瓜菊酯(696)+TX、灭虫菊(cis-resmethrin)+TX、顺式苄呋菊酯(别名)(80)+TX、氰菊酯(别名)+TX、除线威(999)+TX、氯氰碘柳胺(别名)[CCN]+TX、噻虫胺(165)+TX、乙酰亚砷酸铜[CCN]+TX、砷酸铜[CCN]+TX、油酸铜[CCN]+TX、蝇毒磷(174)+TX、畜虫磷(1006)+TX、克罗米通(别名)[CCN]+TX、丁烯磷(1010)+TX、育畜磷(1011)+TX、冰晶石(cryolite)(别名)(177)+TX、CS 708(开发代码)(1012)+TX、苯腈膦(1019)+TX、杀螟腈(184)+TX、果虫磷(1020)+TX、环虫菊[CCN]+TX、乙氰菊酯(188)+TX、氟氯氰菊酯(193)+TX、三氟氯氰菊酯(196)+TX、氯氰菊酯(201)+TX、苯醚氰菊酯(206)+TX、灭蝇胺(209)+TX、赛灭磷(别名)[CCN]+TX、右旋柠檬烯(别名)[CCN]+TX、右旋胺菊酯(别名)(788)+TX、DAEP(1031)+TX、棉隆(216)+TX、DDT(219)+TX、单甲基克百威(decarbofuran)(1034)+TX、溴氰菊酯(223)+TX、田乐磷(1037)+TX、田乐磷-O(1037)+TX、田乐磷-S(1037)+TX、内吸磷(1038)+TX、甲基内吸磷(224)+TX、内吸磷-O(1038)+TX、内吸磷-O-甲基(224)+TX、内吸磷-S(1038)+TX、内吸磷-S-甲基(224)+TX、内吸磷-S-甲基砜(1039)+TX、丁醚脲(226)+TX、氯亚胺硫磷(1042)+TX、杀线虫剂(diamidafos)(1044)+TX、二嗪农(227)+TX、异氯磷(1050)+TX、除线磷(1051)+TX、敌敌畏(236)+TX、二克磷(dicliphos)(别名)+TX、二甲苯基(dicresyl)(别名)[CCN]+TX、百治磷(243)+TX、地昔尼尔(244)+TX、狄氏剂(1070)+TX、二乙基5-甲基吡唑-3-基磷酸盐(IUPAC名称)(1076)+TX、二氟脲(250)+TX、二羟丙茶碱(别名)[CCN]+TX、四氟甲醚菊酯[CCN]+TX、甲氟磷(1081)+TX、地麦威(1085)+TX、乐果(262)+TX、苄菌酯(1083)+TX、二甲基毒虫威(265)+TX、敌蝇威(1086)+TX、消螨酚(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、硝丙酚(1093)+TX、戊硝酚(1094)+TX、地乐酚(1095)+TX、呋虫胺(271)+TX、苯虫醚(1099)+TX、蔬果磷(1100)+TX、二氧威(1101)+TX、敌杀磷(1102)+TX、乙拌磷(278)+TX、地可磷(1108)+TX、DNOC(282)+TX、多拉菌素(别名)[CCN]+TX、DSP(1115)+TX、脱皮甾酮(别名)[CCN]+TX、EI 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25475(开发代码)(1386)+TX、鱼尼丁(别名)(1387)+TX、利阿诺定(传统名称)(1387)+TX、藜芦碱(别名)(725)+TX、八甲磷(1389)+TX、克线丹(sebufos)(别名)+TX、司拉克丁(别名)[CCN]+TX、SI-0009(化合物代码)+TX、SI-0205(化合物代码)+TX、SI-0404(化合物代码)+TX、SI-0405(化合物代码)+TX、氟硅菊酯(728)+TX、SN 72129(开发代码)(1397)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟化钠(IUPAC/化学文摘名称)(1399)+TX、六氟硅酸钠(1400)+TX、五氯酚钠(623)+TX、硒酸钠(IUPAC名称)(1401)+TX、硫氰酸钠[CCN]+TX、苏硫磷(1402)+TX、多杀菌素(737)+TX、螺甲螨酯(739)+TX、螺虫乙酯(spirotetrmat)(CCN)+TX、磺苯醚隆(sulcofuron)(746)+TX、磺苯醚隆钠(746)+TX、氟虫胺(750)+TX、治螟磷(753)+TX、磺酰氟(756)+TX、硫丙磷(1408)+TX、焦油(别名)(758)+TX、τ-氟胺氰菊酯(398)+TX、噻螨威(1412)+TX、TDE(1414)+TX、虫酰肼(762)+TX、吡螨胺(763)+TX、丁基嘧啶磷(764)+TX、氟苯脲(768)+TX、七氟菊酯(769)+TX、双硫磷(770)+TX、TEPP(1417)+TX、环戊烯丙菊酯(1418)+TX、叔丁威(别名)+TX、特丁磷(773)+TX、四氯乙烷[CCN]+TX、杀虫畏(777)+TX、胺菊酯(787)+TX、θ-氯氰菊酯(204)+TX、噻虫啉(791)+TX、久效威(thiafenox)(别名)+TX、噻虫嗪(792)+TX、噻喃磷(thicrofos)(1428)+TX、抗虫威(1431)+TX、杀虫环(798)+TX、杀虫环草酸氢(798)+TX、硫双威(799)+TX、久效威(800)+TX、二甲硫吸磷(801)+TX、硫磷嗪(1434)+TX、杀虫双(thiosultap)(803)+TX、杀虫双钠盐(thiosultap-sodium)(803)+TX、苏云金素(别名)[CCN]+TX、唑虫酰胺(809)+TX、四溴菊酯(812)+TX、四氟苯菊酯(813)+TX、反氯菊酯(transpermethrin)(1440)+TX、威菌磷(1441)+TX、唑蚜威(818)+TX、三唑磷(820)+TX、唑蚜威(别名)+TX、敌百虫(824)+TX、三氯甲基对硫磷-3(别名)[CCN]+TX、壤虫磷(1452)+TX、三氯丙氧磷(1455)+TX、杀铃脲(835)+TX、混杀威(840)+TX、烯虫硫酯(1459)+TX、蚜灭多(847)+TX、甲烯氟虫腈(vaniliprole)[CCN]+TX、藜芦定(别名)(725)+TX、藜芦碱(别名)(725)+TX、XMC(853)+TX、灭杀威(854)+TX、YI-5302(化合物代码)+TX、ζ-氯氰菊酯(205)+TX、灭除威(zetamethrin)(别名)+TX、磷化锌(640)+TX、地可磷(zolaprofos)(1469)和ZXI 8901(开发代码)(858)+TX、氰虫酰胺[736994-63-19+TX、氯虫苯甲酰胺[500008-45-7]+TX、腈吡螨酯[560121-52-0]+TX、丁氟螨酯[400882-07-7]+TX、新喹唑啉(pyrifluquinazon)[337458-27-2]+TX、乙基多杀菌素[187166-40-1+187166-15-0]+TX、螺虫乙酯[203313-25-1]+TX、砜虫啶[946578-00-3]+TX、丁烯氟虫腈[704886-18-0]+TX、氯氟醚菊酯[915288-13-0]+TX、四氟醚菊酯[84937-88-2]+TX、三氟苯嘧啶(triflumezopyrim)(披露于WO 2012/092115)+TX、氟醚嘧啶(fluxametamide)(WO 2007/026965)+TX、ε-甲氧苄氟菊酯[240494-71-7]+TX、ε-氟氯氰菊酯(epsilon-momfluorothrin)[1065124-65-3]+TX、三氟咪啶酰胺(fluazaindolizine)[1254304-22-7]+TX、右旋反式氯丙炔菊酯(chloroprallethrin)[399572-87-3]+TX、氟美酰胺(fluxametamide)[928783-29-3]+TX、氯氟氰虫酰胺(cyhalodiamide)[1262605-53-7]+TX、替氧杂芬(tioxazafen)[330459-31-9]+TX、溴虫氟苯双酰胺(broflanilide)[1207727-04-5]+TX、丁烯氟虫腈[704886-18-0]+TX、环溴虫酰胺[1031756-98-5]+TX、氟氰虫酰胺[1229654-66-3]+TX、戊吡虫胍(描述于WO 2010/060231)+TX、环氧虫啶(描述于WO2005/077934)+TX,
杀软体动物剂,该杀软体动物剂选自由以下组成的物质组:二(三丁基锡)氧化物(IUPAC名称)(913)+TX、溴乙酰胺[CCN]+TX、砷酸钙[CCN]+TX、除线威(cloethocarb)(999)+TX、乙酰亚砷酸铜[CCN]+TX、硫酸铜(172)+TX、三苯锡(347)+TX、磷酸铁(IUPAC名称)(352)+TX、四聚乙醛(518)+TX、灭虫威(530)+TX、氯硝柳胺(576)+TX、氯硝柳胺乙醇胺盐(576)+TX、五氯酚(623)+TX、五氯苯氧化钠(623)+TX、噻螨威(tazimcarb)(1412)+TX、硫双威(799)+TX、三丁基氧化锡(913)+TX、杀螺吗啉(trifenmorph)(1454)+TX、混杀威(trimethacarb)(840)+TX、乙酸三苯基锡(IUPAC名称)(347)和三苯基氢氧化锡(IUPAC名称)(347)+TX、皮瑞普(pyriprole)[394730-71-3]+TX,
一种杀线虫剂,该杀线虫剂选自由以下物质组成的组:AKD-3088(化合物代码)+TX、1,2-二溴-3-氯丙烷(IUPAC/化学文摘名称)(1045)+TX、1,2-二氯丙烷(IUPAC/化学文摘名称)(1062)+TX、1,2-二氯丙烷与1,3-二氯丙烯(IUPAC名称)(1063)+TX、1,3-二氯丙烯(233)+TX、3,4-二氯四氢噻吩1,1-二氧化物(IUPAC/化学文摘名称)(1065)+TX、3-(4-氯苯基)-5-甲基罗丹宁(IUPAC名称)(980)+TX、5-甲基-6-硫代-1,3,5-噻二嗪烷-3-基乙酸(IUPAC名称)(1286)+TX、6-异戊烯基氨基嘌呤(别名)(210)+TX、阿维菌素(1)+TX、乙酰虫腈[CCN]+TX、棉铃威(15)+TX、涕灭威(aldicarb)(16)+TX、涕灭砜威(863)+TX、AZ 60541(化合物代码)+TX、苯氯噻唑(benclothiaz)[CCN]+TX、苯菌灵(62)+TX、丁基哒螨灵(别名)+TX、硫线磷(109)+TX、虫螨威(carbofuran)(118)+TX、二硫化碳(945)+TX、丁硫克百威(119)+TX、三氯硝基甲(141)+TX、毒死蜱(145)+TX、除线威(999)+TX、细胞分裂素(别名)(210)+TX、棉隆(216)+TX、DBCP(1045)+TX、DCIP(218)+TX、除线特(diamidafos)(1044)+TX、除线磷(1051)+TX、二克磷(dicliphos)(别名)+TX、乐果(262)+TX、多拉菌素(别名)[CCN]+TX、埃玛菌素(291)+TX、埃玛菌素苯甲酸盐(291)+TX、依立诺克丁(别名)[CCN]+TX、灭线磷(312)+TX、二溴化乙烯(316)+TX、克线磷(326)+TX、吡螨胺(fenpyrad)(别名)+TX、丰索磷(1158)+TX、噻唑膦(408)+TX、丁硫环磷(1196)+TX、糠醛(别名)[CCN]+TX、GY-81(开发代码)(423)+TX、速杀硫磷[CCN]+TX、碘甲烷(IUPAC名称)(542)+TX、艾沙米多福(isamidofos)(1230)+TX、氯唑磷(1231)+TX、伊佛霉素(别名)[CCN]+TX、激动素(别名)(210)+TX、甲基减蚜磷(1258)+TX、威百亩(519)+TX、威百亩钾盐(别名)(519)+TX、威百亩钠盐(519)+TX、甲基溴(537)+TX、甲基异硫氰酸酯(543)+TX、米尔贝肟(别名)[CCN]+TX、莫昔克丁(别名)[CCN]+TX、疣孢漆斑菌(Myrothecium verrucaria)组合物(别名)(565)+TX、NC-184(化合物代码)+TX、草氨酰(602)+TX、甲拌磷(636)+TX、磷胺(639)+TX、磷虫威[CCN]+TX、克线丹(别名)+TX、司拉克丁(别名)[CCN]+TX、多杀菌素(737)+TX、叔丁威(别名)+TX、特丁磷(773)+TX、四氯噻吩(IUPAC/化学文摘名称)(1422)+TX、thiafenox(别名)+TX、硫磷嗪(1434)+TX、三唑磷(820)+TX、唑蚜威(别名)+TX、二甲苯酚[CCN]+TX、YI-5302(化合物代码)和玉米素(别名)(210)+TX、氟噻虫砜(fluensulfone)[318290-98-1]+TX,
硝化作用抑制剂,该硝化作用抑制剂选自由以下组成的物质组:乙基黄原酸钾[CCN]以及氯啶(nitrapyrin)(580)+TX,
一种植物激活剂,该植物激活剂选自由以下物质组成的组:阿拉酸式苯(6)+TX、噻二唑素-S-甲基(6)+TX、噻菌灵(658)和大虎杖(Reynoutria sachalinensis)提取物(720)+TX,
一种杀鼠剂,该杀鼠剂选自由以下物质组成的组:2-异戊酰茚满-1,3-二酮(IUPAC名称)(1246)+TX、4-(喹喔啉-2-基氨基)苯磺酰胺(IUPAC名称)(748)+TX、α-氯代醇[CCN]+TX、磷化铝(640)+TX、安妥(880)+TX、三氧化二砷(882)+TX、碳酸钡(891)+TX、双鼠脲(912)+TX、溴鼠隆(89)+TX、溴敌隆(91)+TX、溴鼠胺(92)+TX、氰化钙(444)+TX、氮醛糖(127)+TX、氯鼠酮(140)+TX、胆钙化醇(别名)(850)+TX、氯灭鼠灵(1004)+TX、克灭鼠(1005)+TX、杀鼠萘(175)+TX、杀鼠嘧啶(1009)+TX、鼠得克(246)+TX、噻鼠灵(249)+TX、敌鼠钠(273)+TX、钙化醇(301)+TX、氟鼠灵(357)+TX、氟乙酰胺(379)+TX、氟鼠啶(1183)+TX、盐酸氟鼠啶(1183)+TX、γ-HCH(430)+TX、HCH(430)+TX、氢氰酸(444)+TX、碘甲烷(IUPAC名称)(542)+TX、林旦(430)+TX、磷化镁(IUPAC名称)(640)+TX、甲基溴(537)+TX、鼠特灵(1318)+TX、毒鼠磷(1336)+TX、磷化氢(IUPAC名称)(640)+TX、磷[CCN]+TX、杀鼠酮(1341)+TX、亚砷酸钾[CCN]+TX、灭鼠优(1371)+TX、海葱糖苷(1390)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟乙酸钠(735)+TX、士的宁(745)+TX、硫酸铊[CCN]+TX、杀鼠灵(851)和磷化锌(640)+TX,
一种增效剂,该增效剂选自由以下物质组成的组:2-(2-丁氧基乙氧基)乙基胡椒基酯(IUPAC名称)(934)+TX、5-(1,3-苯并二氧杂环戊烯-5-基)-3-己基环己-2-烯酮(IUPAC名称)(903)+TX、法呢醇与橙花叔醇(324)+TX、MB-599(开发代码)(498)+TX、MGK264(开发代码)(296)+TX、增效醚(piperonyl butoxide)(649)+TX、增效醛(1343)+TX、增效酯(propylisomer)(1358)+TX、S421(开发代码)(724)+TX、增效散(1393)+TX、芝麻酚林(sesasmolin)(1394)和亚砜(1406)+TX,
动物驱避剂,该动物驱避剂选自由以下组成的物质组:蒽醌(32)+TX、氯醛糖(127)+TX、环烷酸铜[CCN]+TX、王铜(171)+TX、二嗪磷(227)+TX、二环戊二烯(化学名称)(1069)+TX、双胍盐(guazatine)(422)+TX、双胍醋酸盐(422)+TX、灭虫威(530)+TX、吡啶-4-胺(IUPAC名称)(23)+TX、塞仑(804)+TX、混杀威(trimethacarb)(840)+TX、环烷酸锌[CCN]和福美锌(856)+TX,
一种杀病毒剂,该杀病毒剂选自由以下物质组成的组:衣马宁(别名)[CCN]和利巴韦林(别名)[CCN]+TX,
创伤保护剂,该创伤保护剂选自由以下组成的物质组:氧化汞(512)+TX、辛噻酮(octhilinone)(590)和甲基硫茵灵(802)+TX,
以及生物活性化合物,这些化合物选自由以下物质组成的组:阿扎康唑(60207-31-0]+TX、联苯三唑醇[70585-36-3]+TX、糠菌唑[116255-48-2]+TX、环丙唑醇[94361-06-5]+TX、苯醚甲环唑[119446-68-3]+TX、烯唑醇[83657-24-3]+TX、氟环唑[106325-08-0]+TX、腈苯唑[114369-43-6]+TX、氟喹唑[136426-54-5]+TX、氟硅唑[85509-19-9]+TX、粉唑醇[76674-21-0]+TX、己唑醇[79983-71-4]+TX、抑霉唑[35554-44-0]+TX、亚胺唑[86598-92-7]+TX、种菌唑[125225-28-7]+TX、叶菌唑[125116-23-6]+TX、腈菌唑[88671-89-0]+TX、稻瘟酯[101903-30-4]+TX、戊菌唑[66246-88-6]+TX、丙硫菌唑[178928-70-6]+TX、啶斑肟[88283-41-4]+TX、咪鲜胺[67747-09-5]+TX、丙环唑[60207-90-1]+TX、硅氟唑[149508-90-7]+TX、戊唑醇[107534-96-3]+TX、四氟醚唑[112281-77-3]+TX、三唑酮[43121-43-3]+TX、唑菌醇[55219-65-3]+TX、氟菌唑[99387-89-0]+TX、灭菌唑[131983-72-7]+TX、嘧啶醇[12771-68-5]+TX、氯苯嘧啶醇[60168-88-9]+TX、氟苯嘧啶醇[63284-71-9]+TX、乙嘧酚磺酸酯[41483-43-6]+TX、二甲嘧酚[5221-53-4]+TX、乙嘧酚[23947-60-6]+TX、吗菌灵[1593-77-7]+TX、苯锈啶[67306-00-7]+TX、丁苯吗啉[67564-91-4]+TX、螺环菌胺[118134-30-8]+TX、克啉菌[81412-43-3]+TX、嘧菌环胺[121552-61-2]+TX、嘧菌胺[110235-47-7]+TX、嘧霉胺[53112-28-0]+TX、拌种咯[74738-17-3]+TX、咯菌腈[131341-86-1]+TX、苯霜灵[71626-11-4]+TX、呋霜灵[57646-30-7]+TX、甲霜灵[57837-19-1]+TX、R-甲霜灵[70630-17-0]+TX、甲呋酰胺[58810-48-3]+TX、噁霜灵[77732-09-3]+TX、苯菌灵[17804-35-2]+TX、多菌灵[10605-21-7]+TX、咪菌威[62732-91-6]+TX、呋喃基苯并咪唑[3878-19-1]+TX、噻苯咪唑[148-79-8]+TX、乙菌利[84332-86-5]+TX、菌核利[24201-58-9]+TX、异菌脲[36734-19-7]+TX、甲菌利(myclozoline)[54864-61-8]+TX、腐霉利[32809-16-8]+TX、乙烯菌核利[50471-44-8]+TX、啶酰菌胺[188425-85-6]+TX、萎锈灵[5234-68-4]+TX、甲呋酰胺[24691-80-3]+TX、氟酰胺[66332-96-5]+TX、灭锈胺[55814-41-0]+TX、氧化萎锈灵[5259-88-1]+TX、吡噻菌胺[183675-82-3]+TX、噻呋酰胺[130000-40-7]+TX、双胍盐[108173-90-6]+TX、多果定[2439-10-3][112-65-2](游离碱)+TX、双胍辛胺[13516-27-3]+TX、腈嘧菌酯[131860-33-8]+TX、醚菌胺[149961-52-4]+TX、烯肟菌酯{格拉斯哥英国农作物保护委员会国际会议(Proc.BCPC,Int.Congr.,Glasgow,2003,1,93)}+TX、氟嘧菌酯[361377-29-9]+TX、醚菌酯(kresoxim-methyl)[143390-89-0]+TX、苯氧菌胺[133408-50-1]+TX、肟菌酯[141517-21-7]+TX、肟醚菌胺[248593-16-0]+TX、啶氧菌酯[117428-22-5]+TX、唑菌胺酯[175013-18-0]+TX、福美铁[14484-64-1]+TX、代森锰锌[8018-01-7]+TX、代森锰[12427-38-2]+TX、代森联[9006-42-2]+TX、甲基代森锌[12071-83-9]+TX、福美双[137-26-8]+TX、代森锌[12122-67-7]+TX、福美锌[137-30-4]+TX、敌菌丹[2425-06-1]+TX、克菌丹[133-06-2]+TX、抑菌灵[1085-98-9]+TX、唑呋草[41205-21-4]+TX、灭菌丹[133-07-3]+TX、对甲抑菌灵[731-27-1]+TX、波尔多混合剂[8011-63-0]+TX、氢氧化铜(copperhydroxid)[20427-59-2]+TX、王铜(copperoxychlorid)[1332-40-7]+TX、硫酸铜(coppersulfat)[7758-98-7]+TX、氧化铜(copperoxid)[1317-39-1]+TX、代森锰铜[53988-93-5]+TX、喹啉酮[10380-28-6]+TX、敌螨普[131-72-6]+TX、酞菌酯(nitrothal-isopropyl)[10552-74-6]+TX、克瘟散[17109-49-8]+TX、异稻瘟净(iprobenphos)[26087-47-8]+TX、稻瘟灵[50512-35-1]+TX、氯瘟磷[36519-00-3]+TX、定菌磷[13457-18-6]+TX、甲基立枯磷[57018-04-9]+TX、阿拉酸式苯-S-甲基[135158-54-2]+TX、敌菌灵[101-05-3]+TX、苯噻菌胺(benthiavalicarb)[413615-35-7]+TX、杀稻瘟菌素-S[2079-00-7]+TX、灭螨猛[2439-01-2]+TX、地茂散[2675-77-6]+TX、百菌清[1897-45-6]+TX、环氟菌胺[180409-60-3]+TX、霜脲氰[57966-95-7]+TX、二氯萘醌[117-80-6]+TX、双氯氰菌胺[139920-32-4]+TX、哒菌酮[62865-36-5]+TX、氯硝胺[99-30-9]+TX、乙霉威[87130-20-9]+TX、烯酰吗啉[110488-70-5]+TX、SYP-LI90(氟吗啉)[211867-47-9]+TX、二噻农[3347-22-6]+TX、噻唑菌胺[162650-77-3]+TX、土菌灵[2593-15-9]+TX、噁唑酮菌[131807-57-3]+TX、咪唑菌酮[161326-34-7]+TX、稻瘟酰胺[115852-48-7]+TX、三苯锡[668-34-8]+TX、嘧菌腙[89269-64-7]+TX、氟啶胺[79622-59-6]+TX、氟吡菌胺[239110-15-7]+TX、磺菌胺[106917-52-6]+TX、环酰菌胺[126833-17-8]+TX、三乙膦酸铝[39148-24-8]+TX、噁霉灵[10004-44-1]+TX、丙森锌[140923-17-7]+TX、IKF-916(氰霜唑)[120116-88-3]+TX、春日霉素[6980-18-3]+TX、磺菌威[66952-49-6]+TX、苯菌酮[220899-03-6]+TX、戊菌隆[66063-05-6]+TX、四氯苯酞[27355-22-2]+TX、多氧霉素[11113-80-7]+TX、噻菌灵[27605-76-1]+TX、霜霉威[25606-41-1]+TX、丙氧喹啉[189278-12-4]+TX、咯喹酮[57369-32-1]+TX、喹氧灵[124495-18-7]+TX、五氯硝基苯[82-68-8]+TX、硫[7704-34-9]+TX、噻酰菌胺[223580-51-6]+TX、咪唑嗪[72459-58-6]+TX、三环唑[41814-78-2]+TX、嗪胺灵[26644-46-2]+TX、井冈霉素[37248-47-8]+TX、苯酰菌胺(RH7281)[156052-68-5]+TX、双炔酰菌胺[374726-62-2]+TX、吡唑萘菌胺[881685-58-1]+TX、氟唑环菌胺[874967-67-6]+TX、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(9-二氯亚甲基-1,2,3,4-四氢-1,4-桥亚甲基-萘-5-基)-酰胺(披露于WO 2007/048556)+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(披露于WO 2006/087343)+TX、[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-[(环丙基羰基)氧基]-1,3,4,4a,5,6,6a,12,12a,12b-十氢-6,12-二羟基-4,6a,12b-三甲基-11-氧代-9-(3-吡啶基)-2H,11H萘并[2,1-b]吡喃并[3,4-e]吡喃-4-基]环丙烷甲酸甲酯[915972-17-7]+TX、1,3,5-三甲基-N-(2-甲基-1-氧丙基)-N-[3-(2-甲基丙基)-4-[2,2,2-三氟-1-甲氧基-1-(三氟甲基)乙基]苯基]-1H-吡唑-4-甲酰胺[926914-55-8]+TX;兰蔻三酮(lancotrione)[1486617-21-3]、氯氟吡啶酯[943832-81-3]、艾分氟康唑(ipfentrifluconazole)[1417782-08-1]、氯氟醚菌唑(mefentrifluconazole)[1417782-03-6]、quinofumelin[861647-84-9]、右旋反式氯丙炔菊酯(chloroprallethrin)[399572-87-3]、氯氟氰虫酰胺(cyhalodiamide)[1262605-53-7]、三氟咪啶酰胺(fluazaindolizine)[1254304-22-7]、fluxametamide[928783-29-3]、ε-甲氧苄氟菊酯[240494-71-7]、ε-氟氯氰菊酯(epsilon-momfluorothrin)[1065124-65-3]、氟唑菌酰羟胺[1228284-64-7]、κ-毕芬宁(kappa-bifenthrin)[439680-76-9]、溴虫氟苯双酰胺(broflanilide)[1207727-04-5]、敌克美施(dicloromezotiaz)[1263629-39-5]、敌派美创(dipymetitrone)[16114-35-5]、吡唑嘧啶(pyraziflumid)[942515-63-1]、κ-七氟菊酯(kappa-tefluthrin)[391634-71-2]、制定杀(fenpicoxamid)[517875-34-2]、氟茚唑菌胺(fluindapyr)[1383809-87-7]、α-溴敌隆(alpha-bromadiolone)[28772-56-7]、flupyrimin[1689566-03-7]、benzpyrimoxan[1449021-97-9]、acynonapyr[1332838-17-1]、inpyrfluxam[1352994-67-2]、isoflucypram[1255734-28-1]、tyclopyrazoflor[1477919-27-9]、spiropidion[1229023-00-0]和pyrapropoyne[1803108-03-3];并且
微生物,包括:洛菲不动杆菌(Acinetobacter lwoffii)+TX、枝顶孢菌(Acremonium alternatum)+TX+TX、枝顶孢头孢霉(Acremonium cephalosporium)+TX+TX、Acremonium diospyri+TX、Acremonium obclavatum+TX、粒体病毒(Adoxophyes oranagranulovirus)(AdoxGV)+TX、放射形土壤杆菌(Agrobacterium radiobacter)菌株K84/>+TX、互隔交链孢霉(Alternaria alternate)+TX、决明子链格孢霉(Alternaria cassia)+TX、Alternaria destruens/>+TX、白粉寄生孢(Ampelomyces quisqualis)/>+TX、黄曲霉(Aspergillus flavus)AF36/>+TX、黄曲霉NRRL 21882/>+TX、曲霉菌属(Aspergillus spp.)+TX、出芽短梗霉菌(Aureobasidium pullulans)+TX、固氮螺菌属(Azospirillum)+TX、(+TX、TAZO/>)+TX、固氮菌属(Azotobacter)+TX、Azotobacter chroocuccum+TX、Azotobacter cysts(Bionatural Blooming/>)+TX、解淀粉芽孢杆菌+TX、蜡样芽孢杆菌+TX、Bacillus chitinosporus菌株CM-1+TX、原生祛病芽孢杆菌(Bacillus chitinosporus)菌株AQ746+TX、地衣芽孢杆菌菌株HB-2(BiostartTM )+TX、地衣芽孢杆菌菌株3086(/>+TX、Green/>)+TX、环状芽孢杆菌+TX、坚强芽孢杆菌(/>+TX、/>+TX、/>)+TX、坚强芽孢杆菌菌株I-1582+TX、浸麻芽孢杆菌+TX、Bacillus marismortui+TX、巨大芽孢杆菌+TX、蕈状芽孢杆菌菌株AQ726+TX、乳头状芽孢杆菌(Bacillus papillae)(MilkySpore/>)+TX、短小芽孢杆菌物种+TX、短小芽孢杆菌菌株GB34(Yield/>)+TX、短小芽孢杆菌菌株AQ717+TX、短小芽孢杆菌菌株QST 2808(/>+TX、Ballad)+TX、Bacillus spahericus/>+TX、芽孢杆菌属+TX、芽孢杆菌属菌株AQ175+TX、芽孢杆菌属菌株AQ177+TX、芽孢杆菌属菌株AQ178+TX、枯草芽孢杆菌菌株QST713(/>+TX、/>+TX、/>)+TX、枯草芽孢杆菌菌株QST 714+TX、枯草芽孢杆菌菌株AQ153+TX、枯草芽孢杆菌菌株AQ743+TX、枯草芽孢杆菌菌株QST3002+TX、枯草芽孢杆菌菌株QST3004+TX、枯草芽孢杆菌解淀粉变种菌株FZB24(+TX、/>)+TX、苏云金芽孢杆菌Cry 2Ae+TX、苏云金芽孢杆菌Cry1Ab+TX、苏云金芽孢杆菌鲇泽亚种(aizawai)GC 91/>+TX、苏云金芽孢杆菌以色列亚种(/>+TX、/>+TX、/>)+TX、苏云金芽孢杆菌戈氏亚种(kurstaki)(/>+TX、/>+TX、/>+TX、/>+TX、Scutella/>+TX、Turilav/>+TX、/>+TX、Dipel/>+TX、/>+TX、/>)+TX、苏云金芽孢杆菌戈氏亚种BMP 123/>+TX、苏云金芽孢杆菌戈氏亚种HD-1(Bioprotec-CAF//>)+TX、苏云金芽孢杆菌菌株BD#32+TX、苏云金芽孢杆菌菌株AQ52+TX、苏云金芽孢杆菌鲇泽变种(/>+TX、/>)+TX、细菌物种(/>+TX、/>+TX、/>)+TX、Clavipactermichiganensis的噬菌体/>+TX、/>+TX、球孢白僵菌(/>+TX、Brocaril/>)+TX、球孢白僵菌GHA(Mycotrol/>+TX、Mycotrol/>+TX、)+TX、布氏白僵菌(/>+TX、Schweizer/>+TX、/>)+TX、白僵菌属+TX、灰霉病菌(Botrytis cineria)+TX、慢生型大豆根瘤菌/>+TX、短芽孢杆菌(Brevibacillus brevis)+TX、苏云金芽孢杆菌拟步行甲亚种(tenebrionis)/>+TX、BtBooster+TX、洋葱伯克霍尔德菌(Burkholderiacepacia)(/>+TX、/>+TX、Blue/>)+TX、伯克霍尔德菌(Burkholderia gladii)+TX、唐菖蒲伯克霍尔德菌(Burkholderia gladioli)+TX、伯克氏菌属+TX、加拿大蓟真菌(CBH Canadian/>)+TX、乳酪假丝酵母(Candidabutyri)+TX、无名假丝酵母(Candida famata)+TX、果实念珠菌(Candida fructus)+TX、光滑念珠菌(Candida glabrata)+TX、吉利蒙念珠菌(Candida guilliermondii)+TX、口津假丝酵母(Candida melibiosica)+TX、假丝酵母(Candida oleophila)菌株O+TX、近平滑假丝酵母菌(Candida parapsilosis)+TX、菌膜假丝酵母(Candida pelliculosa)+TX、铁红假丝酵母(Candida pulcherrima)+TX、Candida reukaufii+TX、Candida saitoana(/>+TX、/>)+TX、清酒假丝酵母(Candida sake)+TX、假丝酵母物种+TX、纤细假丝酵母(Candida tenius)+TX、戴氏西地西菌(Cedecea dravisae)+TX、产黄纤维单胞菌(Cellulomonas flavigena)+TX、螺卷毛壳菌(Chaetomium cochliodes)/>+TX、球毛壳菌(Chaetomium globosum)/>+TX、色素细菌(Chromobacteriumsubtsugae)菌株PRAA4-1T/>+TX、芽枝状枝孢菌(Cladosporiumcladosporioides)+TX、尖孢枝孢菌(Cladosporium oxysporum)+TX、Cladosporiumchlorocephalum+TX、枝孢属(Cladosporium spp.)+TX、极细枝孢霉(Cladosporiumtenuissimum)+TX、粉红粘帚霉(Clonostachys rosea)/>+TX、尖孢炭疽菌(Colletotrichum acutatum)+TX、盾壳霉(Coniothyrium minitans)(Cotans/>)+TX、盾壳霉属(Coniothyrium spp.)+TX、浅白隐球酵母(Cryptococcus albidus)+TX、土生隐球菌(Cryptococcus humicola)+TX、Cryptococcusinfirmo-miniatus+TX、罗伦隐球酵母(Cryptococcus laurentii)+TX、苹果异形小卷蛾颗粒体病毒(Cryptophlebia leucotreta granulovirus)/>+TX、贪铜菌(Cupriavidus campinensis)+TX、苹果蠢蛾颗粒体病毒(Cydia pomonella granulovirus) +TX、苹果蠢蛾颗粒体病毒(/>+TX、Madex/>+TX、Madex Max/)+TX、Cylindrobasidium laeve/>+TX、帚梗柱孢属(Cylindrocladium)+TX、汉逊德巴利酵母(Debaryomyces hansenii)+TX、Drechslerahawaiinensis+TX、阴沟肠杆菌(Enterobacter cloacae)+TX、肠杆菌科(Enterobacteriaceae)+TX、Entomophtora virulenta/>+TX、附球菌(Epicoccum nigrum)+TX、黑附球菌(Epicoccum purpurascens)+TX、附球菌属(Epicoccum spp.)+TX、Filobasidiumfloriforme+TX、锐顶镰刀菌(Fusarium acuminatum)+TX、厚垣镰孢霉(Fusariumchlamydosporum)+TX、尖孢镰刀菌(Fusarium oxysporum)(/>/Biofox/>)+TX、层生镰刀菌(Fusarium proliferatum)+TX、镰刀菌属(Fusarium spp.)+TX、溶磷白地霉(Galactomyces geotrichum)+TX、链孢粘帚霉(Gliocladium catenulatum)(/>+TX、/>)+TX、粉红胶枝霉(Gliocladium roseum)+TX、粘帚霉属(Gliocladiumspp.)/>+TX、绿色粘帚霉(Gliocladium virens)/>+TX、颗粒体病毒/>+TX、嗜盐盐芽孢杆菌(Halobacillus halophilus)+TX、岸喜盐芽孢杆菌(Halobacillus litoralis)+TX、特氏盐芽孢杆菌(Halobacillus trueperi)+TX、盐单胞菌属(Halomonas spp.)+TX、Halomonas subglaciescola+TX、嗜盐弧菌(Halovibriovariabilis)+TX、葡萄有孢汉逊酵母(Hanseniaspora uvarum)+TX、棉铃虫核型多角体病毒(Helicoverpa armigera nucleopolyhedrovirus)/>+TX、玉米穗虫(Helicoverpa zea)核型多角体病毒/>+TX、异黄酮-芒柄花黄素/>+TX、柠檬形克勒克酵母(Kloeckera apiculata)+TX、克勒克酵母属(Kloeckera spp.)+TX、大链壶菌(Lagenidium giganteum)/>+TX、Lecanicillium longisporum+TX、Lecanicillium muscarium/>+TX、舞毒蛾(LymantriaDispar)核型多角体病毒/>+TX、嗜盐海球菌(Marinococcus halophilus)+TX、格氏梅拉菌(Meira geulakonigii)+TX、绿僵菌(Metarhizium anisopliae)/>+TX、黑僵菌(Metarhizium anisopliae)(Destruxin/>)+TX、Metschnikowiafruticola/>+TX、美极梅奇酵母菌(Metschnikowia pulcherrima)+TX、双胞镰孢(Microdochium dimerum)/>+TX、青蓝小单孢菌(Micromonosporacoerulea)+TX、小球壳孢(Microsphaeropsis ochracea)+TX、Muscodor albus 620+TX、红斑粘帚菌(Muscodor roseus)菌株A3-5+TX、菌根属(Mycorrhizaespp.)(/>+TX、Root/>)+TX、疣孢漆斑菌(Myrotheciumverrucaria)菌株AARC-0255/>+TX、BROS/>+TX、长喙壳菌(Ophiostomapiliferum)菌株D97/>+TX、粉拟青霉(Paecilomyces farinosus)+TX、玫烟色拟青霉(Paecilomyces fumosoroseus)(/>+TX、/>)+TX、拟青霉(Paecilomyces linacinus)(Biostat/>)+TX、淡紫色拟青霉(Paecilomyceslilacinus)菌株251(MeloCon/>)+TX、多粘类芽孢杆菌(Paenibacillus polymyxa)+TX、成团泛菌(Pantoea agglomerans)(BlightBan/>)+TX、泛菌属(Pantoea spp.)+TX、巴斯德氏芽菌属(Pasteuria spp.)/>+TX、拟斯扎瓦巴氏杆菌(Pasteurianishizawae)+TX、黄灰青霉(Penicillium aurantiogriseum)+TX、Penicillium billai(+TX、/>)+TX、短密青霉(Penicillium brevicompactum)+TX、常现青霉(Penicillium frequentans)+TX、灰黄青霉(Penicillium griseofulvum)+TX、产紫青霉(Penicillium purpurogenum)+TX、青霉菌属(Penicillium spp.)+TX、鲜绿青霉(Penicillium viridicatum)+TX、大伏革菌(Phlebiopsis gigantean)/>+TX、溶磷菌/>+TX、隐地疫霉(Phytophthora cryptogea)+TX、棕榈疫霉(Phytophthora palmivora)/>+TX、异常毕赤酵母(Pichia anomala)+TX、Pichia guilermondii+TX、璞膜毕赤酵母(Pichia membranaefaciens)+TX、指甲毕赤酵母(Pichia onychis)+TX、树干毕赤酵母(Pichia stipites)+TX、绿脓假单胞菌(Pseudomonasaeruginosa)+TX、Pseudomonas aureofasciens(Spot-Less/>)+TX、洋葱假单胞菌(Pseudomonas cepacia)+TX、绿针假单胞菌(Pseudomonas chlororaphis)+TX、起皱假单胞菌(Pseudomonas corrugate)+TX、荧光假单胞菌(Pseudomonas fluorescens)菌株A506(BlightBan/>)+TX、恶臭假单胞菌(Pseudomonas putida)+TX、Pseudomonas reactans+TX、假单胞菌属(Pseudomonas spp.)+TX、丁香假单胞菌(Pseudomonas syringae)/>+TX、绿黄假单胞菌(Pseudomonas viridiflava)+TX、荧光假单胞菌/>+TX、Pseudozymaflocculosa菌株PF-A22UL(Sporodex/>)+TX、Puccinia canaliculata+TX、Pucciniathlaspeos(Wood/>)+TX、Pythium paroecandrum+TX、寡雄腐霉(Pythiumoligandrum)(/>+TX、/>)+TX、Pythium periplocum+TX、水生拉恩菌(Rhanella aquatilis)+TX、拉恩氏菌属(Rhanella spp.)+TX、根瘤菌(Rhizobia)(/>+TX、/>)+TX、丝核菌(Rhizoctonia)+TX、球状红球菌(Rhodococcusgloberulus)菌株AQ719+TX、Rhodosporidium diobovatum+TX、圆红冬孢酵母菌(Rhodosporidium toruloides)+TX、蔷薇色酵母属(Rhodotorula spp.)+TX、粘红酵母(Rhodotorula glutinis)+TX、禾本红酵母(Rhodotorula graminis)+TX、胶红酵母(Rhodotorula mucilagnosa)+TX、深红酵母(Rhodotorula rubra)+TX、酿酒酵母(Saccharomyces cerevisiae)+TX、Salinococcus roseus+TX、小核盘菌(Sclerotiniaminor)+TX、小核盘菌/>+TX、小柱孢属(Scytalidium spp.)+TX、Scytalidium uredinicola+TX、甜菜夜蛾核型多角体病毒(/>+TX、/>)+TX、粘质沙雷氏菌(Serratia marcescens)+TX、普利茅斯沙雷氏菌(Serratia plymuthica)+TX、沙雷氏菌属(Serratia spp.)+TX、粪生粪壳菌(Sordaria fimicola)+TX、灰翅夜蛾核型多角体病毒/>+TX、红掷孢酵母(Sporobolomyces roseus)+TX、嗜麦芽寡养单胞菌(Stenotrophomonas maltophilia)+TX、不吸水链霉菌(Streptomycesahygroscopicus)+TX、Streptomyces albaduncus+TX、Streptomyces exfoliates+TX、鲜黄链霉菌(Streptomyces galbus)+TX、灰平链霉菌(Streptomyces griseoplanus)+TX、灰绿链霉菌(Streptomyces griseoviridiss)/>+TX、利迪链霉菌(Streptomyceslydicus)/>+TX、利迪链霉菌WYEC-108/>+TX、紫色链霉菌(Streptomyces violaceus)+TX、Tilletiopsis minor+TX、铁艾酵母属(Tilletiopsisspp.)+TX、棘孢木霉(Trichoderma asperellum)(T34/>)+TX、Trichodermagamsii/>+TX、深绿木霉(Trichoderma atroviride)/>+TX、钩状木霉(Trichoderma hamatum)TH 382+TX、哈茨木霉(Trichoderma harzianum rifai)+TX、哈茨木霉T-22(/>+TX、PlantShield/>+TX、/>+TX、/>)+TX、哈茨木霉T-39/>+TX、Trichoderma inhamatum+TX、康氏木霉(Trichoderma koningii)+TX、木霉属(Trichodermaspp.)LC 52/>+TX、木素木霉(Trichoderma lignorum)+TX、长梗木霉(Trichoderma longibrachiatum)+TX、Trichoderma polysporum(Binab/>)+TX、紫杉木霉(Trichoderma taxi)+TX、绿色木霉(Trichoderma virens)+TX、绿色木霉(以前称为绿色粘帚霉GL-21)/>+TX、绿色木霉(Trichoderma viride)+TX、绿色木霉菌株ICC 080/>+TX、芽毛孢子菌(Trichosporon pullulans)+TX、毛孢子菌属(Trichosporon spp.)+TX、单端孢属(Trichothecium spp.)+TX、粉红单端孢霉(Trichothecium roseum)+TX、Typhula phacorrhiza菌株94670+TX、Typhula phacorrhiza菌株94671+TX、黑细极格孢(Ulocladium atrum)+TX、奥德曼细基格孢(Ulocladiumoudemansii)(Botry-/>)+TX、玉蜀黍黑粉菌(Ustilago maydis)+TX、各种细菌和补充微量营养素(Natural/>)+TX、各种真菌(Millennium/>)+TX、厚垣轮枝孢菌(Verticillium chlamydosporium)+TX、蜡蚧轮枝菌(Verticillium lecanii)(+TX、/>)+TX、Vip3Aa20/>+TX、Virgibaclillusmarismortui+TX、野油菜黄单胞菌早熟禾致病变种(Xanthomonas campestris pv.Poae)+TX、伯氏致病杆菌+TX、嗜线虫致病杆菌;并且
松树油+TX、印楝素(Plasma Neem/>+TX、/>+TX、+TX、/>+TX、植物IGR(/>+TX、/>)+TX、芥花油(Lilly Miller/>)+TX、土荆芥(Chenopodium ambrosioides near ambrosioides)+TX、菊花提取物/>+TX、印楝油提取物/>+TX、唇形科(Labiatae)精油/>+TX、丁香-迷迭香-薄荷和百里香油提取物(Gardeninsect/>)+TX、甜菜碱/>+TX、大蒜+TX、柠檬草油/>+TX、印楝油+TX、猫薄荷(Nepeta cataria)(猫薄荷油)+TX、猫薄荷+TX、尼古丁+TX、牛至油+TX、胡麻科(Pedaliaceae)油/>+TX、除虫菊+TX、皂皮树(Quillaja saponaria)/>+TX、大虎杖(Reynoutria sachalinensis)(+TX、/>)+TX、鱼藤酮(Eco/>)+TX、芸香科(Rutaceae)植物提取物/>+TX、大豆油(Ortho/>)+TX、茶树油(Timorex/>)+TX、百里香油+TX、/>MMF+TX、/>+TX、迷迭香-芝麻-胡椒薄荷-百里香和肉桂提取物混合物(EF/>)+TX、丁香-迷迭香和薄荷提取物混合物(EF/>)+TX、丁香-胡椒薄荷-大蒜油和薄荷混合物(Soil/>)+TX、高岭土/>+TX、褐藻的贮存葡聚糖/>并且
信息素,包括:黑头萤火虫信息素(3M Sprayable Blackheaded Fireworm)+TX、苹果蠹蛾信息素(Paramount dispenser-(CM)/Isomate/>)+TX、葡萄小卷叶蛾信息素(3M MEC-GBM Sprayable/>)+TX、卷叶虫信息素(3M MEC-LR Sprayable/>)+TX、家蝇信息素(Muscamone)(Snip7 Fly+TX、Starbar Premium Fly/>)+TX、梨小食心虫信息素(3M oriental fruitmoth sprayable/>)+TX、桃透翅蛾(Peachtree Borer)信息素/>+TX、番茄蠢蛾(Tomato Pinworm)信息素(3M Sprayable/>)+TX、衣透斯特粉末(Entostat powder)(棕榈树提取物)(Exosex/>)+TX、(E+TX,Z+TX,Z)-3+TX,8+TX,11十四碳三烯乙酸酯+TX、(Z+TX,Z+TX,E)-7+TX,11+TX,13-十六三烯醛+TX、(E+TX,Z)-7+TX,9-十二碳二烯-1-醇乙酸酯+TX、2-甲基-1-丁醇+TX、乙酸钙+TX、/>+TX、+TX、/>+TX、薰衣草千里酸酯(Lavandulyl senecioate);并且
大生物(macrobial),包括:短距蚜小蜂(Aphelinus abdominalis)+TX、阿尔蚜茧蜂(Aphidius ervi)+TX、木瓜抑虱跳小蜂(Acerophaguspapaya)+TX、二星瓢虫(Adalia bipunctata)/>+TX、二星瓢虫+TX、二星瓢虫/>+TX、串茧跳小蜂(Ageniaspiscitricola)+TX、巢蛾多胚跳小蜂(Ageniaspis fuscicollis)+TX、安氏钝绥螨(Amblyseiusandersoni)(/>+TX、/>)+TX、加州钝绥螨(Amblyseius californicus)(/>+TX、/>))+TX、胡瓜钝绥螨(Amblyseius cucumeris)(/>+TX、Bugline/>)+TX、伪钝绥螨(Amblyseius fallacis)/>+TX、瑞氏钝绥螨(Amblyseius swirskii)(Bugline+TX、/>)+TX、奥氏钝绥螨(Amblyseius womersleyi)+TX、粉虱细蜂(Amitus hesperidum)+TX、原缕翅缕小蜂(Anagrusatomus)+TX、暗腹长索跳小蜂(Anagyrus fusciventris)+TX、卡玛长索跳小蜂(Anagyruskamali)+TX、Anagyrus loecki+TX、粉蚧长索跳小蜂(Anagyrus pseudococci)/>+TX、红蜡蚧扁角跳小蜂(Anicetus benefices)+TX、象虫金小蜂(Anisopteromaluscalandrae)+TX、林地花蝽(Anthocoris nemoralis)/>+TX、短距蚜小蜂(/>+TX、/>)+TX、短翅蚜小蜂(Aphelinus asychis)+TX、科列马阿布拉小蜂(Aphidius colemani)/>+TX、阿尔蚜茧蜂(Aphidius ervi)/>+TX、烟蚜茧蜂(Aphidius gifuensis)+TX、桃赤蚜蚜茧蜂(Aphidius matricariae)+TX、食蚜癭蚊(Aphidoletes aphidimyza)/>+TX、食蚜癭蚊/>+TX、黄蚜小蜂(Aphytis lingnanensis)+TX、印巴黄蚜小蜂(Aphytismelinus)+TX、蜚卵啮小蜂(Aprostocetus hagenowii)+TX、隐翅虫(Atheta coriaria)+TX、熊蜂属(Bombus spp.)+TX、欧洲熊蜂(Bombus terrestris)(Natupol/>)+TX、欧洲熊蜂(/>+TX、/>)+TX、Cephalonomiastephanoderis+TX、Chilocorus nigritus+TX、普通草铃(Chrysoperla carnea)+TX、普通草铃/>+TX、Chrysoperla rufilabris+TX、Cirrospilus ingenuus+TX、蛹寄生蜂(Cirrospilus quadristriatus)+TX、白腹啮小蜂(Citrostichus phyllocnistoides)+TX、Closterocerus chamaeleon+TX、Closterocerusspp.+TX、Coccidoxenoides perminutus/>+TX、Coccophagus cowperi+TX、赖食蚧蚜小蜂(Coccophagus lycimnia)+TX、螟黄足盘绒茧蜂(Cotesia flavipes)+TX、菜蛾盘绒茧蜂(Cotesia plutellae)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(+TX、/>)+TX、日本方头甲(Cybocephalus nipponicus)+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)+TX、西伯利亚离颚茧蜂/>+TX、豌豆潜蝇姬小蜂(Diglyphus isaea)/>+TX、小黑瓢虫(Delphastus catalinae)+TX、Delphastus pusillus+TX、Diachasmimorpha krausii+TX、长尾潜蝇茧蜂(Diachasmimorpha longicaudata)+TX、长凹姬蜂(Diaparsis jucunda)+TX、阿里食虱跳小蜂(Diaphorencyrtus aligarhensis)+TX、豌豆潜蝇姬小蜂(Diglyphus isaea)+TX、豌豆潜叶蝇姬小蜂(/>+TX、/>)+TX、西伯利亚离颚茧蜂(/>+TX、/>)+TX、歧脉跳小蜂属(Diversinervus spp.)+TX、盾蚧长缨蚜小蜂(Encarsiacitrina)+TX、丽蚜小蜂(Encarsia formosa)(/>+TX、/>+TX、En-)+TX、浆角蚜小蜂(Eretmocerus eremicus)/>+TX、哥德恩蚜小蜂(Encarsia guadeloupae)+TX、海地恩蚜小蜂(Encarsia haitiensis)+TX、细扁食蚜蝇(Episyrphus balteatus)/>+TX、Eretmoceris siphonini+TX、加州桨角蚜小蜂(Eretmocerus californicus)+TX、浆角蚜小蜂(Eretmocerus eremicus)(/>+TX、Eretline/>)+TX、浆角蚜小蜂/>+TX、海氏桨角蚜小蜂(Eretmocerushayati)+TX、蒙氏桨角蚜小蜂(Eretmocerus mundus)(/>+TX、Eretline/>)+TX、Eretmocerus siphonini+TX、四斑光缘瓢虫(Exochomus quadripustulatus)+TX、食螨癭蚊(Feltiella acarisuga)/>+TX、食螨癭蚊/>+TX、阿里山潜蝇茧蜂(Fopius arisanus)+TX、Fopius ceratitivorus+TX、芒柄花黄素(Formononetin)(Wirless/>)+TX、细腰凶蓟马(Franklinothrips vespiformis)/>+TX、西方静走螨(Galendromus occidentalis)+TX、莱氏棱角肿腿蜂(Goniozus legneri)+TX、麦蛾柔茧蜂(Habrobracon hebetor)+TX、异色瓢虫(Harmonia axyridis)+TX、异小杆线虫属(Heterorhabditis spp.)(Lawn/>)+TX、嗜菌异小杆线虫(Heterorhabditis bacteriophora)(NemaShield/>+TX、/>+TX、/>+TX、/>+TX、/>+TX、/>+TX、/>+TX、/>)+TX、大异小杆线虫(Heterorhabditis megidis)(Nemasys/>+TX、BioNem/>+TX、Exhibitline/>+TX、/>)+TX、集栖瓢虫(Hippodamia convergens)+TX、尖狭下盾螨(Hypoaspis aculeifer)(+TX、/>)+TX、兵下盾螨(Hypoaspis miles)(Hypoline/>+TX、/>)+TX、黑色枝跗瘿蜂(Lbalia leucospoides)+TX、Lecanoideus floccissimus+TX、Lemophagus errabundus+TX、三色刚突跳小蜂(Leptomastidea abnormis)+TX、Leptomastix dactylopii/>+TX、长角跳小蜂(Leptomastix epona)+TX、Lindorus lophanthae+TX、Lipolexis oregmae+TX、叉叶绿蝇(Lucilia caesar)/>+TX、茶足柄瘤蚜茧蜂(Lysiphlebus testaceipes)+TX、暗黑长脊盲蝽(Macrolophus caliginosus)(/>+TX、Macroline/>+TX、)+TX、Mesoseiulus longipes+TX、黄色阔柄跳小蜂(Metaphycus flavus)+TX、Metaphycus lounsburyi+TX、角纹脉褐蛉/>+TX、黄色花翅跳小蜂(Microterys flavus)+TX、Muscidifurax raptorellus和Spalangia cameroni/>+TX、Neodryinus typhlocybae+TX、加州新小绥螨(Neoseiulus californicus)+TX、黄瓜新小绥螨(Neoseiulus cucumeris)/>+TX、虚伪新小绥螨(Neoseiulusfallacis)+TX、Nesideocoris tenuis(/>+TX、/>)+TX、古铜黑蝇(Ophyra aenescens)/>+TX、狡诈花蝽(Orius insidiosus)(/>+TX、)+TX、无毛小花蝽(Orius laevigatus)(/>+TX、/>)+TX、大型小花蝽(Orius majusculus)(Oriline/>)+TX、小黑花椿象(Orius strigicollis)+TX、Pauesia juniperorum+TX、酸酱瓢虫腹柄姬小蜂(Pediobiusfoveolatus)+TX、Phasmarhabditis hermaphrodita/>+TX、Phymastichuscoffea+TX、Phytoseiulus macropilus+TX、智利小植绥螨(Phytoseiulus persimilis)(+TX、Phytoline/>)+TX、斑腹刺益蝽(Podisus maculiventris)+TX、Pseudacteon curvatus+TX、Pseudacteon obtusus+TX、火蚁寄生蚤蝇(Pseudacteon tricuspis)+TX、Pseudaphycus maculipennis+TX、Pseudleptomastixmexicana+TX、具毛嗜木虱跳小蜂(Psyllaephagus pilosus)+TX、同色短背茧蜂(Psyttaliaconcolor)(complex)+TX、胯姬小蜂属(Quadrastichus spp.)+TX、Rhyzobius lophanthae+TX、澳洲瓢虫(Rodolia cardinalis)+TX、Rumina decollate+TX、Semielacher petiolatus+TX、麦长管蚜/>+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)(Nematac+TX、/>+TX、BioNem/>+TX、/>+TX、/>+TX、)+TX、夜蛾斯氏线虫(Steinernema feltiae)(/>+TX、Nemasys/>+TX、BioNem/>+TX、/>+TX、/>+TX、/>+TX、Exhibitline/>+TX、Scia-/>+TX、/>)+TX、锯蜂线虫(Steinernema kraussei)(Nemasys/>+TX、BioNem/>+TX、Exhibitline/>)+TX、里奥布拉夫线虫(Steinernema riobrave)(/>+TX、/>)+TX、蝼蛄斯氏线虫(Steinernema scapterisci)(Nematac/>)+TX、斯氏线虫属(Steinernemaspp.)+TX、Steinernematid spp.(Guardian/>)+TX、深点食螨瓢虫(Stethorus punctillum)/>+TX、亮腹釉小蜂(Tamarixia radiate)+TX、Tetrastichus setifer+TX、Thripobius semiluteus+TX、中华长尾小蜂(Torymussinensis)+TX、甘蓝夜蛾赤眼蜂(Trichogramma brassicae)(Tricholine/>)+TX、甘蓝夜蛾赤眼蜂/>+TX、广赤眼蜂(Trichogramma evanescens)+TX、微小赤眼蜂(Trichogramma minutum)+TX、玉米螟赤眼蜂(Trichogramma ostriniae)+TX、宽脉赤眼蜂(Trichogramma platneri)+TX、短管赤眼蜂(Trichogramma pretiosum)+TX、螟黑点瘤姬蜂(Xanthopimpla stemmator);并且
其他生物制剂,包括:脱落酸+TX、+TX、紫韧革菌(Chondrostereumpurpureum)(Chontrol/>)+TX、胶孢炭疽菌(Colletotrichum gloeosporioides)+TX、辛酸铜/>+TX、三角洲陷阱(Delta trap)(Trapline/>)+TX、梨火疫病菌(Erwinia amylovora)(Harpin)(/>+TX、Ni-HIBIT Gold/>)+TX、磷酸铁/>+TX、漏斗陷阱(Funnel trap)/>+TX、+TX、Grower's/>+TX、高油菜素内酯(Homo-brassonolide)+TX、磷酸铁(Lilly Miller Worry Free Ferramol Slug&Snail/>)+TX、MCP冰雹陷阱(MCP hailtrap)(Trapline/>)+TX、象甲和寄生蜂(Microctonus hyperodae)+TX、大豆红褐坏死病菌(Mycoleptodiscus terrestris)/>+TX、/>+TX、/>+TX、/>+TX、信息素陷阱(Pheromone trap)(Thripline/>)+TX、碳酸氢钾+TX、脂肪酸钾盐/>+TX、硅酸钾溶液/>+TX、碘化钾+硫氰酸钾/>+TX、/>+TX、蜘蛛毒液+TX、蝗虫小孢子虫(Nosema locustae)(Semaspore Organic Grasshopper/>)+TX、粘滞陷阱(Sticky trap)(Trapline/>+TX、Rebell/>)+TX和陷阱(Takitrapline y+)+TX。
在活性成分之后的括号中的参考,例如[3878-19-1]是指化学文摘登记号。上文描述的混合配伍物是已知的。当活性成分包括在“The Pesticide Manual”[杀虫剂手册][ThePesticide Manual-A World Compendium[杀虫剂手册-世界纲要];第十三版;编者C.D.S.TomLin;英国农作物保护委员会]中时,它们按照上文对于特定化合物在圆括号内给出的条目编号描述于该手册中;例如,化合物“阿维菌素”按照条目编号(1)描述。当上文对特定化合物添加“[CCN]”时,所考虑的化合物包括在“Compendium of Pesticide CommonNames”[杀虫剂通用名纲要]中,该纲要可在互联网上获得[A.Wood;Compendium of Pesticide Common Names[杀虫剂通用名纲要],1995-2004];例如化合物“乙酰虫腈”在互联网地址http://www.alanwood.net/pesticides/acetoprole.html下进行了描述。
多数活性成分通过上文中所谓的“通用名”来表示,在不同的情形中使用相应的“ISO通用名”或其它“通用名”。若其名称不是“通用名”,则所使用的名称种类以特定化合物的圆括号中所给出的名称来代替;在这种情况下,使用IUPAC名称、IUPAC/化学文摘名称、“化学名称”、“传统名称”、“化合物名称”或“开发代码”,或者如果既没有使用这些名称之一也没有使用“通用名”,则使用“别名”。“CAS登记号”意指化学文摘登记号。
选自表1至表9和表P的具有式I的化合物与上述活性成分的活性成分混合物包含选自表1至表9和表P的化合物和如上所述的活性成分,它们优选地处于从100:1至1:6000,特别是从50:1至1:50的混合比,更特别是处于从20:1至1:20的比率,甚至更特别是从10:1至1:10,非常特别是从5:1至1:5,特别优选的从2:1至1:2的比率,同样优选的是从4:1至2:1的比率,尤其是1:1、或5:1、或5:2、或5:3、或5:4、或4:1、或4:2、或4:3、或3:1、或3:2、或2:1、或1:5、或2:5、或3:5、或4:5、或1:4、或2:4、或3:4、或1:3、或2:3、或1:2、或1:600、或1:300、或1:150、或1:35、或2:35、或4:35、或1:75、或2:75、或4:75、或1:6000、或1:3000、或1:1500、或1:350、或2:350、或4:350、或1:750、或2:750、或4:750的比率。那些混合比率是按重量计的。
如上所述的混合物可以被用于控制有害生物的方法中,该方法包括将含如上文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。
包含选自表1至表9和表P的具有式I的化合物和一种或多种如上所述的活性成分的混合物可以例如如下施用:以单一的“掺水即用”的形式,以组合式喷雾混合物(该混合物由这些单一活性成分组分的单独配制品构成,例如“桶混剂”),以及当以顺序方式(即,一个在另一个适度短的时间段之后,如几小时或几天)施用时组合使用这些单一活性成分。施用选自表1至表9和表P的具有式I的化合物和如上所述的活性成分的顺序对于实施本发明不是本质性的。
根据本发明的组合物还可以包含其他固体或液体助剂,例如稳定剂,例如未环氧化的或环氧化的植物油(例如环氧化的椰子油、菜籽油或大豆油),消泡剂(例如硅酮油),防腐剂,粘度调节剂,粘合剂和/或增粘剂,肥料或其他用于获得特定效果的活性成分,例如杀细菌剂、杀真菌剂、杀线虫剂、植物活化剂、杀软体动物剂或除草剂。
根据本发明的组合物是以本身已知的方式,在不存在助剂的情况下,例如通过研磨、筛选和/或压缩固体活性成分;和在至少一种助剂的存在下,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。
这些组合物的施用方法,即控制上述类型的有害生物的方法,如喷雾、雾化、撒粉、刷涂、包衣、撒播或浇灌-它们被选择以适于普遍情况的预期目的-以及这些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。每公项的施用量总体上是每公项1g到2000g活性成分,尤其是10g/ha到1000g/ha,优选地是10g/ha到600g/ha。
在作物保护领域中,优选的施用方法是施用至这些植物的叶(叶施药),可能的是选择施用的频率和比率以符合所讨论的有害生物的侵染风险。可替代地,该活性成分可以通过根系统(内吸作用)到达植物,这是通过用一种液体组合物将这些植物的所在地浸透或者通过将固体形式的活性成分引入植物的所在地(例如引入土壤,例如以颗粒(土施)的形式)来实现的。在水稻作物的情况下,这样的颗粒剂可以被计量地加入淹水的稻田中。
本发明的这些化合物及其组合物还适合于植物繁殖材料的保护(例如种子,像果实、块茎或籽粒,或者苗圃植物),以对抗上述类型的有害生物。可以用该化合物在种植前对该繁殖材料进行处理,例如可以在播种前对种子进行处理。可替代地,该化合物可以施用至种子籽粒(包衣),这是通过将籽粒浸渍入液体组合物中或通过包衣固体组合物层实现的。还可能在该繁殖材料被种植在施用处时施用这些组合物,例如在条播期间将这些组合物施入种子犁沟。这些用于植物繁殖材料的处理方法和因此处理的植物繁殖材料是本发明另外的主题。典型的处理比率将取决于有待控制的植物以及有害生物/真菌,通常在每100kg种子1克至200克之间,优选在每100kg种子5克至150克之间,诸如在每100kg种子10克至100克之间。
术语种子包括所有种类的种子以及植物繁殖体,包括但并不限于真正的种子、种子块、吸盘、谷粒、鳞球茎、果实、块茎、谷物、根茎、插条、切割枝条以及类似物并且在优选实施例中是指真正的种子。
本发明还包括用具有式I的化合物包衣或处理的种子或含有具有式I的化合物的种子。尽管成分的较多或较少的部分可以渗透到该种子材料中,这取决于施用的方法,术语“包衣或处理和/或含有”通常表示在施用的时候,在大多数情况下,该活性成分在该种子的表面。当所述种子产品被(再)种植时,它可以吸收活性成分。在实施例中,本发明使得其上粘附有具有式(I)的化合物的植物繁殖材料可得。此外,由此可得包括用具有式(I)的化合物处理过的植物繁殖材料的组合物。
种子处理包括本领域中已知的所有适合的种子处理技术,如拌种、种子包衣、种子撒粉、浸种以及种子造粒。可以通过任何已知的方法实现具有式(I)的化合物的种子处理施用,如在种子播种之前或播种/种植过程中喷雾或通过撒粉。
生物学实例:
实例B1:针对小菜蛾(Plutella xylostella)(菜蛾)的活性
通过用移液管移液用从10’000ppm DMSO储备溶液制备的水性测试溶液处理具有人工饲料的24孔微量滴定板。在干燥之后,用L2期幼虫对各板进行侵染(10至15只/孔)。侵染5天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。
以下化合物在200ppm的施用率下在两个类别(死亡率或生长抑制)中的至少一个中产生至少80%的效果:P1、P2、P3、P4、P5、P6、P7、P8、P9、P11、P12、P13、P14、P15、P16、P19、P22和P23。
实例B2:针对桃蚜(Myzus persicae)(绿桃蚜)的活性
将向日葵叶圆片置于24孔微量滴定板中的琼脂上并用从10'000ppm DMSO储备溶液制备的水性测试溶液进行喷雾。在干燥之后,将这些叶圆片用混合年龄的蚜虫群体进行侵染。侵染6天之后,针对死亡率对这些样品进行评估。
以下化合物在200ppm的施用率下导致至少80%的死亡率:P1、P2、P3、P4、P5、P6、P7、P8、P9、P11、P12、P13、P14、P15、P16、P17、P18、P19、P20、P22和P23。
实例B3:针对桃蚜(Myzus persicae)(绿桃蚜)的活性
将用混合年龄的蚜虫种群侵染的豌豆幼苗的根直接置于从10'000DMSO储备溶液制备的水性测试溶液中。在将幼苗置于测试溶液中后6天,针对死亡率评估样品。
以下化合物在24ppm的测试率下导致至少80%的死亡率:P1、P2、P5、P6、P7、P8、P9、P11、P13、P14、P16、P19、P20、P21、P22和P23。
实例B4:针对西花蓟马(Frankliniella occidentalis)(西方花蓟马)的活性
将向日葵叶圆片置于24孔微量滴定板中的琼脂上并且用从10’000DMSO储备溶液制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用混合年龄的花蓟马种群进行侵染。侵染7天之后,针对死亡率对这些样品进行评估。
以下化合物在200ppm的施用率下导致至少80%的死亡率:P1、P2、P3、P5、P6、P7、P8、P9、P11、P12、P13、P16、P19、P20和P22。
实例B5:针对烟粉虱(Bemisia tabaci)(棉粉虱)的活性
将棉花叶圆片置于24孔微量滴定板中的琼脂上并且用从10'000ppm DMSO储备溶液制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用成年粉虱进行侵染。孵育6天之后,针对死亡率对这些样品进行检查。
以下化合物在200ppm的施用率下导致至少80%的死亡率:P1、P2、P3、P4、P5、P6、P7、P8、P9、P11、P12、P13、P14、P16、P19、P21、P22和P23。
实例B6:针对英雄美洲蝽(Euschistus heros)(新热带褐臭蝽)的活性
用从10'000ppm DMSO储备溶液制备的水性测试溶液对24孔微量滴定板中的琼脂上的大豆叶喷雾。在干燥后,用N-2若虫侵染叶子。侵染5天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。
以下化合物在200ppm的施用率下在两个类别(死亡率或生长抑制)中的至少一个中产生至少80%的效果:P1、P2、P3、P4、P5、P6、P7、P8、P9、P11、P12、P13、P14、P15、P16、P17、P18、P19、P20、P21、P22和P23。
实例B7:针对黄瓜条叶甲(Diabrotica balteata)(玉米根虫)的活性
将24孔微量滴定板中的置于琼脂层上的玉米芽通过喷雾用从10’000ppm DMSO储备溶液制备的水性测试溶液进行处理。在干燥之后,用L2期幼虫对各板进行侵染(6至10只/孔)。侵染4天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。
以下化合物在200ppm的施用率下在两个类别(死亡率或生长抑制)中的至少一个中产生至少80%的效果:P2、P3、P4、P7、P8、P9、P11、P12、P15、P16、P17、P18、P19和P20。
实例B7:针对灰翅夜蛾(Spodoptera littoralis)(埃及棉叶虫)的活性
将棉花叶圆片置于24孔微量滴定板中的琼脂上并用从10'000ppm DMSO储备溶液制备的水性测试溶液进行喷雾。在干燥后,将叶圆片用五只L1幼虫进行侵染。与侵染后3天的未处理样品相比,针对死亡率、拒食作用和生长抑制评估样品。当类别死亡率、拒食作用和生长抑制中的至少一个高于未处理的样品时,实现测试样品对灰翅夜蛾的控制。
以下化合物在200ppm的施用率下导致至少80%的控制:P1、P2、P3、P4、P5、P7、P8、P9、P11、P12、P13、P16和P22。
实例B7:针对灰翅夜蛾(Spodoptera littoralis)(埃及棉叶虫)的活性
将测试化合物用移液管从10’000ppm DMSO储备溶液施用到24孔板中并且与琼脂进行混合。将莴苣种子置于琼脂上并且用另一块也包含琼脂的平板封闭该多孔板。7天之后,根吸收了化合物并且莴苣生长进入了盖平板。然后,将这些莴苣叶切到盖平板中。将夜蛾属卵吸移穿过潮湿凝胶印记纸上的塑料模板及其所封闭的盖平板。侵染6天之后,相比于未处理样品,针对死亡率、拒食效果以及生长抑制对这些样品进行评估。
以下化合物在12.5ppm的测试率下在三个类别(死亡率、拒食或生长抑制)中的至少一个中产生至少80%的效果:P3和P7。
实例B7:针对二斑叶螨(Tetranychusurticae)(二点叶螨)的活性
将24孔微量滴定板中的琼脂上的豆叶圆片用从10’000ppmDMSO储备溶液制备的水性测试溶液进行喷雾。在干燥之后,将叶圆片用混合年龄的螨种群进行侵染。侵染8天之后,针对混合种群(流动平台)的死亡率对这些样品进行评估。
以下化合物在200ppm的施用率下导致至少80%的死亡率:P2、P3、P4、P7、P11和P23。
实例B7:针对烟蓟马(Thripstabaci)(洋葱蓟马)的活性
将向日葵叶圆片置于24孔微量滴定板中的琼脂上并用从10'000ppm DMSO储备溶液制备的水性测试溶液进行喷雾。在干燥后,将叶圆片用混合年龄的蓟马种群侵染。侵染6天之后,针对死亡率对这些样品进行评估。
以下化合物在200ppm施用率下导致至少80%的死亡率:P2和P9。
Claims (3)
1.一种用于制备具有式(XI-A)的化合物
或其盐的方法,其中Rf是C1-C6卤代烷基,所述方法包括
a.使具有式14的化合物
其中Y1独立地是氯、甲氧基或乙氧基;
与具有式15的化合物
其中Rf是C1-C6卤代烷基;并且
Y2是甲氧基或乙氧基;
在碱存在下进行反应,以产生具有式16的化合物
或其盐;或其互变异构体和E/Z同分异构体;
其中Rf是C1-C6卤代烷基;并且
Y1独立地是氯、甲氧基或乙氧基;并且
b.使具有式16的化合物
或其盐;或其互变异构体和E/Z同分异构体;
其中Rf是C1-C6卤代烷基;并且
Y1独立地是氯、甲氧基或乙氧基;
与氨或其盐进行反应,以产生具有式17的化合物
或其互变异构体和E/Z同分异构体;
其中Rf是C1-C6卤代烷基;并且
Y1独立地是氯、甲氧基或乙氧基;并且
c.使具有式17的化合物
或其互变异构体和E/Z同分异构体;
其中Rf是C1-C6卤代烷基;并且
Y1独立地是氯、甲氧基或乙氧基;
与铵盐在酸存在下进行反应,以产生具有式10的化合物
或其盐;
其中Rf是C1-C6卤代烷基;并且
d.使具有式10的化合物
或其盐;
其中Rf是C1-C6卤代烷基;
与卤化剂进行反应,以产生具有式11的化合物
或其盐;
其中Rf是C1-C6卤代烷基;并且
Hal是卤素;并且
e.使具有式11的化合物
或其盐;
其中Rf是C1-C6卤代烷基;并且
Hal是卤素;
与甲胺或其盐进行反应,以产生具有式(XI-A)的化合物
或其盐;
其中Rf是C1-C6卤代烷基。
2.一种用于制备具有式10的化合物或其盐的方法,所述方法包括:
b1.使具有式16的化合物
或其盐;或其互变异构体和E/Z同分异构体;
其中Rf是C1-C6卤代烷基;并且
Y1独立地是氯、甲氧基或乙氧基;
与氨或其盐进行反应,以产生反应混合物;并且
b2使所述混合物直接与铵盐在酸存在下进行反应,以产生具有式10的化合物
或其盐;
其中Rf是C1-C6卤代烷基。
3.一种具有式17的化合物
或其互变异构体和E/Z同分异构体;
其中Rf是C1-C6卤代烷基;并且
Y1独立地是氯、甲氧基或乙氧基。
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BR112021012991A2 (pt) | 2018-12-31 | 2021-09-14 | Syngenta Crop Protection Ag | Derivados heterocíclicos pesticidamente ativos com substituintes contendo enxofre |
WO2021053110A1 (en) | 2019-09-20 | 2021-03-25 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur and sulfoximine containing substituents |
CN111223532B (zh) * | 2019-11-14 | 2023-06-20 | 腾讯科技(深圳)有限公司 | 确定目标化合物的反应物的方法、设备、装置、介质 |
EP4259627A1 (en) * | 2020-12-14 | 2023-10-18 | Basf Se | Sulfoximine pesticides |
TW202304919A (zh) | 2021-03-31 | 2023-02-01 | 印度商皮埃企業有限公司 | 稠合雜環化合物及其作為害蟲控制劑之用途 |
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US20190322675A1 (en) | 2019-10-24 |
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