CN112262140A - 具有含亚砜亚胺取代基的杀有害生物活性杂环衍生物 - Google Patents
具有含亚砜亚胺取代基的杀有害生物活性杂环衍生物 Download PDFInfo
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- CN112262140A CN112262140A CN201980038081.5A CN201980038081A CN112262140A CN 112262140 A CN112262140 A CN 112262140A CN 201980038081 A CN201980038081 A CN 201980038081A CN 112262140 A CN112262140 A CN 112262140A
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Abstract
披露了具有式(I)的化合物,其中取代基是如权利要求1中所定义的。此外,本发明涉及包含具有式(I)的化合物的农用化学组合物、涉及这些组合物的制备、并且涉及所述化合物或组合物在农业或园艺中用于对抗、预防或控制动物有害生物的用途,所述动物有害生物包括节肢动物并且特别是昆虫、线虫、软体动物或蜱螨目的代表。
Description
本发明涉及包含亚砜亚胺(sulfoximine)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。
具有含硫取代基的杀有害生物活性杂双环取代的环丙基衍生物是已知的并且描述于文献,例如,WO 2018/077565、WO 2018/070502、WO 2017/146226、WO 2017/089190、WO2017/084879、WO 2016/121997、WO 2016/104746、WO 2016/096584、WO 2016/046071、WO2016/071214、WO 2016/039441、WO 2016/026848、WO 2016/023954、WO 2014/142292和WO2016/020286中。杀有害生物活性杂环亚砜亚胺衍生物先前已经描述于文献,例如,WO2015/071180中。
现在已经出人意料地发现某些新颖的双环含亚砜亚胺取代的环丙基衍生物作为杀有害生物剂具有有利的特性。
因此本发明提供了具有式I的化合物,
其中
A是CH或N
R1是C1-C4烷基
R2是氢、氰基、-C(O)R7、-C(O)OR8、C1-C6烷基或-CONR9R10、SO2R11
其中
R7是氢、C1-C6烷基或C1-C6卤代烷基,且R8是C1-C6烷基或C1-C6卤代烷基;
R9、R10彼此独立地是氢或C1-C6烷基;
R11是C1-C6烷基;
R3是氢、C1-C3烷基、C1-C3卤代烷基、氰基、-CO2H、-CO2NH2、C1-C4烷氧基羰基、C1-C4烷基氨基羰基、C1-C4二烷基氨基羰基
n是0或1;
Q是选自由以下组成的组的基团:式Q1、Q2、Q3、Q4和Q5
其中箭头指示与掺入了基团A的环的附接点;
并且其中
R4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;
X1是O或NR5;
R5是C1-C4烷基;
R6是C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、或C3-C6环烷基;
G1和G2彼此独立地是N或CH;
或具有式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、互变异构体或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形成例如酸加成盐:强无机酸(例如矿物酸,例如高氯酸、硫酸、硝酸、硝酸类酸(nitrose acid)、磷酸或氢卤酸),强有机羧酸(例如未取代的或例如被卤素取代的C1-C4烷羧酸,例如乙酸,例如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,例如羟基羧酸,例如抗坏血酸、乳酸、苹果酸、酒石酸或柠檬酸,或例如苯甲酸),或有机磺酸(例如未取代的或例如被卤素取代的C1-C4烷磺酸或芳基磺酸,例如甲烷磺酸或对甲苯磺酸)。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(例如吗啉,哌啶,吡咯烷,单、二或三低级烷基胺,例如乙胺、二乙胺、三乙胺或二甲基丙基胺,或单、二或三羟基低级烷基胺,例如单乙醇胺、二乙醇胺或三乙醇胺)形成盐。
如本文所用,术语“C1-Cn烷基”是指具有1至n个碳原子的经由这些碳原子中任一个附接的饱和直链或支链烃基,例如以下基团中的任一种: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、及其分支异构体。例如,还可以提及以下基团中任一种:1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、正己基、正戊基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、或1-乙基-2-甲基丙基。如下文所述,卤代烷基、卤代烷基硫烷基、卤代烷基亚磺酰基、卤代烷基磺酰基、烷氧基和卤代烷氧基衍生自烷基基团。
卤素通常是氟、氯、溴或碘。相应地,这还适用于结合其他含义的卤素,例如卤代烷基。
如本文所用,术语“C1-Cn卤代烷基”是指具有1至n个碳原子的直链或支链饱和C1-Cn烷基(如上提及的),其中这些基团中的一些或全部氢原子可以被氟、氯、溴和/或碘替代,即,例如以下中的任一种:氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟甲基、氯二氟甲基、2-氟乙基、2-氯乙基、2-溴乙基、2-碘乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基、2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、2,2,3,3,3-五氟丙基、七氟丙基、1-(氟甲基)-2-氟乙基、1-(氯甲基)-2-氯乙基、1-(溴甲基)-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基、九氟丁基、1,1-二氟-2,2,2-三氯乙基和2,2,3,3-四氟乙基;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。
如本文所用,术语“C1-Cn烷氧基”是指具有1至n个碳原子的、经由氧原子附接的直链或支链饱和C1-Cn烷基(如上提及的),即,例如以下基团中的任一种: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、叔丁氧基、1-甲基丙氧基、2-甲基丙氧基和1,1-二甲基乙氧基以及还有异构体戊氧基和己氧基;优选地是甲氧基和乙氧基。
如本文所用,术语“C1-Cn卤代烷氧基”是指具有1至n个碳原子的、经由氧原子附接(类似于C1-Cn烷氧基)的直链或支链饱和C1-Cn卤代烷基(如上提及的)。
如本文所用,术语“C1-Cn烷基硫烷基”是指具有1至n个碳原子的直链或支链饱和烷基(如上所述),其通过硫原子连接,即例如甲硫基、乙硫基、正丙硫基、1-甲基乙硫基、丁硫基、1-甲基丙硫基、2-甲基丙硫基或1,1-二甲基乙硫基中的任何一种。
如本文所用,术语“C1-Cn卤代烷基硫烷基”是指如上所述的C1-Cn烷基硫烷基,其部分或完全被氟、氯、溴和/或碘取代,即例如氟甲硫基、二氟甲硫基、三氟甲硫基、氯二氟甲硫基、溴二氟甲硫基、2-氟乙硫基、2-氯乙硫基、2-溴乙硫基、2-碘乙硫基、2,2-二氟乙硫基、2,2,2-三氟乙硫基、2,2,2-三氯乙硫基、2-氯-2-氟乙硫基、2-氯-2,2-二氟乙硫基、2,2-二氯-2-氟乙硫基、五氟乙硫基、2-氟丙硫基、3-氟丙硫基、2-氯丙硫基、3-氯丙硫基、2-溴丙硫基、3-溴丙硫基、2,2-二氟丙硫基、2,3-二氟丙硫基、2,3-二氯丙硫基、3,3,3-三氟丙硫基、3,3,3-三氯丙硫基、2,2,3,3,3-五氟丙硫基、七氟丙硫基、1-(氟甲基)-2-氟乙硫基、1-(氯甲基)-2-氯乙硫基、1-(溴甲基)-2-溴乙硫基、4-氟丁硫基、4-氯丁硫基或4-溴丁硫基中的任何一种。
类似的考虑适用于术语“C1-Cn卤代烷基亚磺酰基”和“C1-Cn卤代烷基磺酰基”,其是指C1-Cn卤代烷基硫烷基(如上提及的),但是其中硫处于不同的氧化态,例如分别为亚砜-S(O)C1-Cn卤代烷基或砜-S(O)2C1-Cn卤代烷基。因此,例如基团,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。
如本文使用的术语“C3-C6环烷基”是指3-6元环烷基,如环丙烷、环丁烷、环丙烷、环戊烷和环己烷。
术语“C1-Cn烷氧基羰基”是指具有1至n个碳原子、经由羰基基团附接的直链或支链饱和C1-Cn烷氧基(如上提及的)。
术语“C1-Cn烷基氨基羰基”是指具有1至n个碳原子、经由氨基羰基基团的氮原子附接的直链或支链饱和C1-Cn烷基(如上提及的)。
术语“C1-Cn二烷基氨基羰基”是指具有1至n个碳原子(相同或不同个数)、经由氨基羰基基团的氮原子附接的两个直链或支链饱和C1-Cn烷基(如上提及的)。
末端单键(自由基)在给定分子结构的背景下代表甲基或在可变基团定义的背景下代表附接点。
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。
如下所述,提供了根据本发明的实施例。
实施例1提供了如上所定义的具有式I的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物。
实施例2提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
A是CH或N;
R1是乙基、丙基或异丙基;
R2是氢、氰基、C1-C3烷基、C1-C3烷基羰基、C1-C3烷氧基羰基、C1-C3卤代烷基羰基;
R3是氢、C1-C3卤代烷基、氰基、-CO2H、-CO2NH2、C1-C4二烷基氨基羰基;并且
n是1。
实施例3提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
A是CH或N;
R1是乙基;
R2是氢;
R3是氢、C1-C2卤代烷基、氰基、-CO2NH2、C1-C2二烷基氨基羰基;并且
n是1。
实施例4提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
A是CH或N;
R1是乙基;
R2是氢;
R3是氢、氰基或CO2NH2;并且
n是1。
实施例5提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
A是CH或N;
R1是乙基;
R2是氢;
R3是氢或氰基;并且
n是1。
实施例6提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
Q是选自Q1、Q2、Q4和Q5的基团
其中箭头指示与掺入了基团A的环的附接点;
并且其中
R4是C1-C2卤代烷基、C1-C2卤代烷基硫烷基、C1-C2卤代烷基亚磺酰基或C1-C2卤代烷基磺酰基;
X1是氧或NCH3;
R6是C1-C2烷基、C1-C2卤代烷基、C1-C2烷氧基或环丙基;并且
G1和G2彼此独立地是N或CH。
实施例7提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
是选自Q1、Q2和Q5的基团
其中箭头指示与掺入了基团A的环的附接点;
并且其中
R4是C1-C2氟烷基、三氟甲基硫烷基、三氟甲基亚磺酰基、三氟甲基磺酰基、二氟甲基硫烷基、二氟甲基亚磺酰基、或二氟甲基磺酰基;
X1是NCH3;
R6是甲基、乙基、2,2,2-三氟乙基、甲氧基或环丙基;并且
G1和G2彼此独立地是N或CH。
实施例8提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
Q是选自Q1和Q5的基团
其中箭头指示与掺入了基团A的环的附接点;
并且其中
R4是三氟甲基、五氟乙基、三氟甲基硫烷基、三氟甲基亚磺酰基或三氟甲基磺酰基;
X1是NCH3;
R6是乙基、甲氧基或环丙基;并且
G1是N且G2是CH,或G1是CH且G2是N,或G1和G2是N,或G1和G2是CH。
实施例9提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
Q是基团Q1
其中箭头指示与掺入了基团A的环的附接点;
并且其中
R4是三氟甲基;
X1是NCH3;并且
G1是N且G2是CH,G1是CH且G2是N,或者G1和G2是N。
实施例10提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
A是CH或N;
R1是乙基、丙基或异丙基;
R2是氢、氰基、C1-C3烷基、C1-C3烷基羰基、C1-C3烷氧基羰基、C1-C3卤代烷基羰基;
R3是氢、C1-C3卤代烷基、氰基、CO2H、CO2NH2、C1-C4二烷基氨基羰基;
n是1;
Q是选自Q1、Q2、Q4和Q5的基团
其中箭头指示与掺入了基团A的环的附接点;
并且其中
R4是C1-C2卤代烷基、C1-C2卤代烷基硫烷基、C1-C2卤代烷基亚磺酰基或C1-C2卤代烷基磺酰基;
X1是氧或NCH3;
R6是C1-C2烷基、C1-C2卤代烷基、C1-C2烷氧基或环丙基;并且
G1和G2彼此独立地是N或CH。
实施例11提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
A是CH或N;
R1是乙基;
R2是氢;
R3是氢、C1-C2卤代烷基、氰基、CO2NH2、C1-C2二烷基氨基羰基;
n是1;
Q是选自Q1、Q2和Q5的基团
其中箭头指示与掺入了基团A的环的附接点;
并且其中
R4是C1-C2氟烷基、三氟甲基硫烷基、三氟甲基亚磺酰基、三氟甲基磺酰基、二氟甲基硫烷基、二氟甲基亚磺酰基、或二氟甲基磺酰基;
X1是NCH3;
R6是甲基、乙基、2,2,2-三氟乙基、甲氧基或环丙基;并且
G1和G2彼此独立地是N或CH。
实施例12提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
A是CH或N;
R1是乙基;
R2是氢;
R3是氢、氰基或CO2NH2;
n是1;
Q是选自Q1和Q5的基团
其中箭头指示与掺入了基团A的环的附接点;
并且其中
R4是三氟甲基、五氟乙基、三氟甲基硫烷基、三氟甲基亚磺酰基或三氟甲基磺酰基;
X1是NCH3;
R6是乙基、甲氧基或环丙基;并且
G1是N且G2是CH,或G1是CH且G2是N,或G1和G2是N,或G1和G2是CH。
实施例13提供了根据实施例1所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
A是CH或N;
R1是乙基;
R2是氢;
R3是氢或氰基;
n是1;
Q是基团Q1
其中箭头指示与掺入了基团A的环的附接点;
并且其中
R4是三氟甲基;
X1是NCH3;并且
G1是N且G2是CH,G1是CH且G2是N,或者G1和G2是N。
实施例14提供了根据实施例1、2、3、4或5所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
Q是选自Q1-1、Q1-2、Q1-3、Q1-4和Q1-5的基团
其中箭头指示与掺入了基团A的环的附接点;并且
R4是三氟甲基、三氟甲基硫烷基或三氟甲基磺酰基。
实施例15提供了根据实施例14所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物:
其中Q是选自Q1-2、Q1-3、Q1-4和Q1-5的基团。
实施例16提供了根据实施例1、2、3、4或5所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
Q是选自Q5的基团
其中箭头指示与掺入了基团A的环的附接点;
R4是三氟甲基、三氟甲基硫烷基或三氟甲基磺酰基;并且
R6是OCH3、CH2CH3或环丙基。
实施例17提供了根据实施例1、2、3、4或5所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
Q是基团Q2
其中箭头指示与掺入了基团A的环的附接点;
R4是三氟甲基、三氟甲基硫烷基或三氟甲基磺酰基;并且
G2是N或CH。
实施例18提供了根据实施例1、2、3、4或5所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
Q是Q3;并且
R4是三氟甲基、三氟甲基硫烷基或三氟甲基磺酰基。
实施例19提供了根据实施例1、2、3、4或5所述的化合物或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,其中:
Q是Q4
其中箭头指示与掺入了基团A的环的附接点;
R4是三氟甲基、三氟甲基硫烷基或三氟甲基磺酰基;并且
G1是N且G2是CH,G1是CH且G2是N,G1和G2是CH,或G1和G2是N;优选地,G1是CH且G2是N。
在另一方面,本发明提供了一种组合物,其包含杀昆虫、杀螨、杀线虫或杀软体动物有效量的如前述实施例1-19中任一项所定义的具有式(I)的化合物、或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,以及任选地,助剂或稀释剂。
在另一方面,本发明提供了一种对抗并控制昆虫、螨、线虫或软体动物的方法,所述方法包括向有害生物、有害生物的场所或易受有害生物攻击的植物施用杀昆虫、杀螨、杀线虫或杀软体动物有效量的如前述实施例1-19中任一项所定义的具有式(I)的化合物、或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,或如以上所定义的组合物。
在又另一方面,本发明提供一种用于保护植物繁殖材料免受昆虫、螨、线虫或软体动物攻击的方法,该方法包括用如上文所定义的组合物处理所述繁殖材料或所述繁殖材料所种植的场所。
根据本发明的用于制备具有化学式(I)的化合物的工艺原则上通过本领域普通技术人员已知的方法来进行。具有式I的化合物的亚组(其中n是0,即硫亚胺Ia,其中R1、R2、R3、A和Q是如以上所定义的)可以通过在亚胺化(imination)反应条件下使对应的具有式II的硫化物(其中R1、R2、R3、A和Q是如以上所定义的)发生反应来制备(步骤A,方案1)。具有式I的化合物的具体亚组(其中n是1,被定义为亚砜亚胺I,其中R1、R2、R3、A和Q是如上所定义的)可以通过氧化具有式Ia的硫亚胺化合物(其中R1、R2、R3、A和Q是如上所定义的)来获得(步骤B)。
方案1
相反地,这两个步骤的顺序可以颠倒,由此具有式I的亚砜亚胺化合物(其中R1、R2、R3、A和Q是如以上所定义的)可以在适当的亚胺化反应条件下由具有式III的亚砜(其中R1、R2、R3、A和Q是如以上所定义的)制备(步骤A’)。
获得具有式I的化合物的典型制备方法和反应条件(无论是针对硫亚胺Ia(步骤A)还是亚砜亚胺I(步骤A’))可以在以下文献中找到,例如H.Okamura,C.Bolm,Org.Lett.[有机快报],2004,6,1305-1307;H.Okamura,C.Bolm,Chem.Lett.[化学快报],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。典型的亚胺化试剂/条件可以定义为NaN3/H2SO4、O-均三甲苯磺酰基-羟胺(MSH)或金属催化的方法[见O.G.Mancheno,C.Bolm,Chem.Eur.J.[欧洲化学杂志],2007,13,6674-6681],如R2-N3/FeCl2、R2-NH2/Fe(acac)3/PhI=O、PhI=N-R2/Fe(OTf)2、PhI=N-R2/CuOTf、PhI=N-R2/Cu(OTf)2、PhI=N-R2/CuPF6、PhI(OAc)2/R2-NH2/MgO/Rh2(OAc)4或氧杂吖丙啶(oxaziridine)(例如3-(4-氰基-苯基)-氧杂吖丙啶-2-甲酸叔丁酯)。
特别令人感兴趣的是具有式II的硫化物和/或具有式III的亚砜的无金属亚胺化方法,以制备具有式Ia的硫亚胺(步骤A)和/或具有式I的亚砜亚胺(步骤A’)。此类亚胺化反应涉及R2-NH2和氧化剂,例如PhI(OAc)2/R2-NH2,其描述于G.Y.Cho,C.Bolm,TetrahedronLett.[四面体通讯],2005,46,8007-8008;或N-溴代琥珀酰亚胺(NBS)/R2-NH2和碱(如叔丁醇钠或叔丁醇钾),其描述于C.Bolm等人,Synthesis[合成]2010,第17期,2922-2925。也可以替代性地使用氧化剂例如N-碘代琥珀酰亚胺(NIS)或碘,如例如在O.G.Mancheno,C.Bolm,Org.Lett.[有机快报]2007,9,3809-3811中所描述的。在WO2008/106006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。
对于硫亚胺Ia到亚砜亚胺I(步骤B)的转化,可以涉及经典氧化试剂,例如KMnO4、NaMnO4、mCPBA、NaIO4/RuO2、NaIO4/RuCl3、H2O2、过硫酸氢钾制剂(oxone)。具体而言,使用钌盐与碱金属高碘酸盐结合和可替代地使用碱金属高锰酸盐描述于WO 2008/097235和WO2008/106006中。
用于合成这样的分别具有式Ia、I的硫亚胺和/或亚砜亚胺化合物的详细制备条件还给出于例如WO 2006/061200或WO 2007/080131中。
可替代地,具有式I的亚砜亚胺化合物的亚组,其中R2是氢且n是1,并且其中R1、R3、A和Q如式I中所定义,
方案1a
可以通过使具有式II的硫化物(其中R1、R3、A和Q如式I中所定义)与合适的氮源(如氨、氨基甲酸铵或乙酸铵(优选氨基甲酸铵)),在高价碘试剂(如二乙酰氧基碘苯)存在下,在溶剂(如甲苯、乙腈或甲醇)中,在0和100℃之间的温度下(优选在室温附近)反应(方案1a),类似于例如在Chem.Commun.[化学通讯]53,348-351;2017(和其中引用的参考文献)中找到的描述来制备。
具有式Ib的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1且R2是CN)可以通过在溶剂(如二氯甲烷)中用三氟乙酸酐处理而被转化为具有式Ic的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1且R2是C(O)CF3),如例如O.G.Mancheno,C.Bolm,Org.Lett.[有机快报]2007,9,3809-3811中所描述的。具有式Ic的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1且R2是C(O)CF3)可以通过在极性质子溶剂(如甲醇或乙醇)中用碱(如碳酸钠或碳酸钾)处理而被转化为具有式I的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1且R2是氢),如例如H.Okamura,C.Bolm,Org.Lett.[有机快报]2004,6,1305-1307中所描述的。具有式Id的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1,其中R2是C(O)NH2)可以通过在有机溶剂(如乙腈)中用强酸(如浓硫酸)处理由具有式Ib的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1,其中R2是CN)制备,如例如WO 09/111309中所描述的。方案2中概括了该化学过程。
方案2
具有式Ie的化合物(其中R1、R3、A和Q是如以上所定义的,并且其中n是1且R2是C1-C6烷基)可以通过在-20℃与150℃之间、优选0℃与80℃之间的温度下,在惰性溶剂中优选地在合适的碱(如碱金属碳酸盐例如碳酸钠或碳酸钾、或碱金属氢化物如氢化钠、或碱金属氢氧化物如氢氧化钠和氢氧化钾)的存在下用具有式LG-R2的烷基化剂(其中LG是离去基团,如卤素(尤其是溴或碘))、磺酸酯OSO2R12(尤其是甲磺酸酯或甲苯磺酸酯)(其中R12是C1-C6烷基、C1-C6卤代烷基或任选地被硝基或C1-C3烷基取代的苯基)、或硫酸酯(如硫酸二甲酯)处理由具有式I的化合物(其中R1、R3、A和Q是如以上所定义的,并且其中n是1并且其中R2是氢)制备。待使用的溶剂的实例包括醚,如四氢呋喃、乙二醇二甲醚(1,2-二甲氧基乙烷)、叔丁基甲基醚和1,4-二噁烷;芳香烃,如甲苯和二甲苯;腈,如乙腈;或极性非质子溶剂,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮或二甲亚砜。
具有式If的化合物(其中R1、R3、A和Q是如以上所定义的,并且其中n是1且R2是C(O)R7并且R7是C1-C6烷基或C1-C6卤代烷基)可以通过在0℃与50℃之间的温度下,在惰性溶剂中,任选地在酰化催化剂(如4-二甲基氨基吡啶(DMAP))的存在下,优选地在碱(如三乙胺、二异丙基乙胺或吡啶)的存在下用具有式LG1-C(O)R7的试剂或具有式R7C(O)-O-C(O)R7的酸酐试剂(其中R7是如以上所定义的并且LG1是离去基团,如卤素(尤其是氯))处理由具有式I的化合物(其中R1、R3、A和Q是如以上所定义的,并且其中n是1且R2是氢)制备。待使用的溶剂的实例包括醚,例如四氢呋喃、乙二醇二甲醚、叔丁基甲基醚和1,4-二噁烷;芳香烃,例如甲苯和二甲苯;卤代烃,如二氯甲烷和氯仿;腈,例如乙腈;或极性非质子溶剂,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮或二甲亚砜。该反应可以在过量的碱的存在下进行,该碱然后还可以充当溶剂或稀释剂。
具有式Ig的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1,其中R2是C(O)OR8并且R8是C1-C6烷基、C1-C6卤代烷基)可以通过在0℃与50℃之间的温度下,在惰性溶剂中,任选地在酰化催化剂(如4-二甲基氨基吡啶(DMAP))的存在下,优选地在碱(如三乙胺、二异丙基乙胺或吡啶)的存在下用具有式LG2-C(O)OR8的试剂(其中R8是如上所定义的并且LG2是离去基团,如卤素(尤其是氯))处理由具有式I的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1且R2是氢)制备。待使用的溶剂的实例包括醚,例如四氢呋喃、乙二醇二甲醚、叔丁基甲基醚和1,4-二噁烷;芳香烃,例如甲苯和二甲苯;卤代烃,如二氯甲烷和氯仿;腈,例如乙腈;或极性非质子溶剂,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮或二甲亚砜。该反应可以在过量的碱的存在下进行,该碱然后还可以充当溶剂或稀释剂。
具有式Ih的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1,并且其中R2是CONR9R10并且R9、R10彼此独立地是氢或C1-C6烷基)可以通过在0℃与50℃之间的温度下,在惰性溶剂中,任选地在酰化催化剂(如4-二甲基氨基吡啶(DMAP))的存在下,优选地在碱(如三乙胺、二异丙基乙胺或吡啶)的存在下用具有式LG3-C(O)NR9R10的试剂(其中R9和R10是如上所定义的并且LG3是离去基团,如卤素(尤其是氯))处理由具有式I的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1,并且其中R2是氢)制备。待使用的溶剂的实例包括醚,例如四氢呋喃、乙二醇二甲醚、叔丁基甲基醚和1,4-二噁烷;芳香烃,例如甲苯和二甲苯;卤代烃,如二氯甲烷和氯仿;腈,例如乙腈;或极性非质子溶剂,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮或二甲亚砜。该反应可以在过量的碱的存在下进行,该碱然后还可以充当溶剂或稀释剂。
具有式Ii的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1,并且其中R2是SO2R11并且R11是C1-C6烷基)可以通过在0℃与50℃之间的温度下,在惰性溶剂中,任选地在酰化催化剂(如4-二甲基-氨基吡啶(DMAP))的存在下,优选地在碱(如三乙胺、二异丙基乙胺或吡啶)的存在下用具有式LG4-SO2R11的试剂(其中R11是如上所定义的并且LG4是离去基团,如卤素(尤其是氯))处理由具有式I的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1,并且其中R2是氢)制备。待使用的溶剂的实例包括醚,例如四氢呋喃、乙二醇二甲醚、叔丁基甲基醚和1,4-二噁烷;芳香烃,例如甲苯和二甲苯;卤代烃,如二氯甲烷和氯仿;腈,例如乙腈;或极性非质子溶剂,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮或二甲亚砜。该反应可以在过量的碱的存在下进行,该碱然后还可以充当溶剂或稀释剂。具有式Ij的化合物(其中R1、R2、R3和Q是如上所定义的并且其中n是1,其中R2是C(O)R7并且R7是氢)可以通过在0℃与180℃之间的温度下,任选地在酸活化剂(如对甲苯磺酸)的存在下,任选地在惰性有机溶剂的存在下,用原甲酸三烷基酯(如原甲酸三甲酯)处理由具有式I的化合物(其中R1、R3、A和Q是如上所定义的并且其中n是1且R2是氢)制备。该反应可以在过量的原甲酸三烷基酯的存在下进行,该酯然后还可以充当溶剂或稀释剂。这样一种方法示于例如WO 2006/037945中。以上所述的转化在方案3中说明。
方案3
在一些情况下,具有式II的化合物(其中R3是氢)是已知的,例如:
2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-5-(三氟甲氧基)-1,3-苯并噁唑,CAS[2128705-99-5],WO 2017146226;2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-5-(二氟甲基硫烷基)-1,3-苯并噁唑,CAS[2128706-06-7],WO 2017146226;2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-5-(二氟甲氧基)-1,3-苯并噁唑,CAS[2128706-01-2],WO 2017146226;5-环丙基-2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-4-酮,CAS[2098699-63-7],WO 2017089190;5-环丙基-2-(4-环丙基-2-乙基硫烷基-苯基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-4-酮,CAS[2098699-80-8],WO 2017089190;2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-5-(1,1,2,2,2-五氟乙基)-1,3-苯并噁唑,CAS[1975147-97-7],WO 2016121997;2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-5-(三氟甲基硫烷基)-1,3-苯并噁唑,CAS[1975147-94-4],WO 2017146226;2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-1-甲基-5-(三氟甲基)苯并咪唑,CAS[1975147-91-1],WO 2016121997;2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-6-(三氟甲基)噁唑并[5,4-b]吡啶,CAS[1975147-87-5],WO 2016121997;2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-3-甲基-6-(1,1,2,2,2-五氟乙基)咪唑并[4,5-b]吡啶,CAS[1975147-85-3],WO 2016121997;6-(5-环丙基-3-乙基硫烷基-2-吡啶基)-7-甲基-3-(2,2,2-三氟乙氧基)咪唑并[4,5-c]哒嗪,CAS[1957168-99-8],WO 2016104746;2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶,CAS[1951416-89-9],WO 2016096584;2-(4-环丙基-2-乙基硫烷基-苯基)-7-(三氟甲基)咪唑并[1,2-c]嘧啶,CAS[1923785-41-4],WO 2016071214;2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-7-(三氟甲基)咪唑并[1,2-c]嘧啶,CAS[1923784-36-4],WO 2016071214;2-(4-环丙基-2-乙基硫烷基-苯基)-5-乙基-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-4-酮,CAS[1879051-89-4],WO 2016023954;2-(4-环丙基-2-乙基硫烷基-苯基)-3,5-二甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-4-酮,CAS[1879051-88-3],WO 2016023954。
具有式II的化合物(其中R3是H),即具有式IIa的化合物
通常可以通过使具有式IV的化合物(其中A、Q和R1是如在以上式I中所定义的)与具有式V的化合物反应来制备,如在方案4中所示:
方案4
更具体地,可以通过使具有式IIa的化合物与具有式V的化合物(其中Xb1可以是卤素(优先地是氯、溴或碘),并且Yb1可以是硼衍生的官能团,如例如B(OH)2或B(ORb1)2,其中Rb1可以是C1-C6烷基基团或这两个基团ORb1可以与硼原子一起形成五元或六元环(如例如频哪醇硼酸酯))进行反应来制备具有式IIa的化合物(如在方案4中描述的)(铃木(Suzuki)交叉偶联,参见例如Tetrahedron Letters[四面体快报],43(39),6987-6990;2002)。在式IIa中,A、R1和Q是如在式I中所描述的。该反应可以通过钯基催化剂,例如四(三苯基膦)钯(0)、双(三苯基膦)二氯化钯(II)、氯(2-二环己基膦基2',4',6'-三异丙基-1,1'-联苯基)[2-(2'-氨基-1,1'-联苯基)]钯(II)(XPhos环钯配合物)、(1,1’双(二苯基膦基)-二茂铁)二氯化钯-二氯甲烷(1:1复合物)或乙酸钯加膦配体(例如像,三苯基膦或三环己基膦),在碱(像碳酸钠、磷酸三钾或氟化铯)的存在下,在溶剂(如甲苯、1,2-二甲氧基乙烷DME、四氢呋喃或二噁烷)或溶剂混合物(像例如,1,2-二甲氧基乙烷(或二噁烷、甲苯、或四氢呋喃)和水的混合物)中,优选地在惰性气氛下进行催化。反应温度的范围可以优选地是从环境温度到反应混合物的沸点,或者可替代地,可以在微波辐射下进行加热。
可替代地,可以使具有式IV的化合物(其中Xb1可以是卤素(优先地是氯、溴或碘))与具有式V的化合物(其中Yb1是卤化镁基团,如-MgBr(库马达(Kumada)交叉偶联))任选地在添加剂(如卤化锌)的存在下进行反应(Journal of Organic Chemistry[有机化学杂志],75(19),6677-6680;2010)。该反应可以通过钯基催化剂进行催化,或可以涉及镍基催化剂,如1,3-双(二苯基膦基)丙烷镍二氯化物(dppp)NiCl2。
还已知的是具有式IV的化合物与具有式V的化合物(其中Yb1是卤化锌基团,如-ZnBr(根岸(Negishi)交叉偶联))之间的反应,如例如在以下文献中说明的:SyntheticCommunications[合成通讯],28(2),225-232;1998。该反应可以通过钯基催化剂,例如像(1,1'双(二苯基膦基)-二茂铁)二氯化钯Pd(dppf)Cl2或双(三苯基膦)二氯化钯(II),任选地在膦添加剂(例如像2-二环己基-膦基-2',6'-二甲氧基-联苯基S-PHOS)的存在下,在溶剂(像例如1,2-二甲氧基乙烷、二噁烷、甲苯、或四氢呋喃)中,优选地在惰性气氛下进行催化。反应温度可以优先地范围从环境温度到反应混合物的沸点。
在一些情况下,具有式II的化合物(其中R3是氰基)是已知的,例如:
1-[5-乙基硫烷基-6-[5-甲氧基-3-甲基-4-氧代-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]环丙烷甲腈,CAS[2225113-68-6],WO 2018/077565;1-[3-乙基硫烷基-4-[5-甲氧基-3-甲基-4-氧代-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]苯基]环丙烷甲腈,CAS[CAS[2225113-73-3],WO 2018/077565;1-[4-[5-环丙基-3-甲基-4-氧代-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-乙基硫烷基-苯基]环丙烷甲腈,CAS[2098699-74-0],WO 2017/089190;1-[6-[5-环丙基-3-甲基-4-氧代-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-5-乙基硫烷基-3-吡啶基]环丙烷甲腈,CAS[2098699-59-1],WO 2017/089190;1-[5-乙基硫烷基-6-[5-(三氟甲基硫烷基)-1,3-苯并噁唑-2-基]-3-吡啶基]环丙烷甲腈,CAS[1975148-53-8],WO 2016/121997;1-[3-乙基硫烷基-4-[7-(三氟甲基)咪唑并[1,2-c]嘧啶-2-基]苯基]环丙烷甲腈,CAS[1923785-47-0],WO 2016/071214;1-[5-乙基硫烷基-6-[7-(三氟甲基)咪唑并[1,2-c]嘧啶-2-基]-3-吡啶基]环丙烷甲腈,CAS[1923784-42-2],WO2016/071214。
其他具有式II的化合物(其中R3是氰基且R1、A和Q是如在式I中所定义的),即具有式IIb的化合物
可以如方案5中所示制备:
方案5
如在方案5中示出的,在氟化锌(II)和钯(0)催化剂(如三(二亚苄基丙酮)二钯(0)-氯仿加合物(Pd2(dba)3)、配体(例如Xantphos)的存在下,在惰性溶剂(如DMF)中,在100-160℃之间的温度下,任选地在微波加热下,用三甲基硅烷基-乙腈TMSCN处理具有式IV的化合物(其中R1、Q和A如在式I中定义的,并且其中Xb1优选地是卤素(甚至更优选地是氯、溴或碘),产生具有式VI的化合物。这样的化学过程已在文献中描述,例如,在Org.Lett.[有机化学通讯],16(24),6314-6317;2014中。可以在碱(如氢化钠、K2CO3、或Cs2CO3)的存在下,在惰性溶剂(如DMF、丙酮、或乙腈)中,用具有式VII的化合物(其中Xb1是如上所定义的)处理具有式IV的化合物,以给出具有式IIb的化合物。可替代地,具有式IIb的化合物可以通过用Pd2(dba)3、配体(如BINAP)、强碱(如LiHMDS)在惰性溶剂(如THF)中,在40℃-70℃的温度下,用具有式VIII的化合物处理而直接从具有式IV的化合物制备。这样的化学过程已经描述于例如J.Am.Chem.Soc.[美国化学会志],127(45),15824-15832;2005中。
具有式IIb的化合物的另一种方法涉及使具有式IV的化合物(其中A、R1和Q如在式I下所描述的,并且其中Xb1是卤素(优选地是氯、溴、碘))与4-异噁唑硼酸或4-异噁唑硼酸频哪醇酯(具有式IX的化合物)在氟化钾(KF)和钯催化剂(如双(三苯基膦)钯(II)二氯化物(Pd(PPh3)2Cl2))存在下,在惰性溶剂(如二甲基亚砜DMSO)中、任选地在与水的混合物中,在40℃-150℃之间的温度下,任选地在微波加热下进行反应产生具有式IX的化合物(其中Q、R1和A如在式I下所描述的)。使具有式IX的化合物与水性氟化钾KF(浓度在0.5与3M之间、优选1M)在惰性溶剂(如二甲基亚砜DMSO或甲醇)中,在20℃-150℃之间的温度下,任选地在微波加热下进行反应产生具有式VI的化合物(其中A、R1和Q如在式I下所描述的)。具有式V的化合物转化成具有式IIb的化合物如上文所述。这样的化学过程已经描述在以下文献中:例如J Am Chem Soc[美国化学会志]2011,133,6948-6951。
具有式IIb的化合物可以进一步用于制备具有式II的化合物(方案6),其中R3进一步被官能化。实际上,在本领域技术人员已知的酸性或碱性条件下,可以将具有式IIb的化合物(其中,A、R1、X1和R2如以上式I中所定义)部分水解为具有式IIc的化合物,或完全水解成具有式IId的化合物。任选地在HF的存在下,用试剂(如SF4或Fluolead(4-叔-丁基-2,6-二甲基苯基三氟化硫)处理具有式IIc的化合物产生具有式IIe的化合物(如在例如OrganicLetters[有机快报],16,6314-6317;2014中所描述的)。
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(IId)的化合物(其中R1、Q和A如式I中所定义)活化以形成活化物质(IIf),其中Q、R1和A如式I中所定义,并且其中X0是卤素,优选氯。例如,化合物(IIf)(其中X0是卤素、优选氯)是通过在20℃至100℃之间(优选25℃)的温度下,在惰性溶剂(如二氯甲烷CH2Cl2或四氢呋喃THF)中,在催化量的N,N-二甲基甲酰胺DMF的存在下,用例如草酰氯(COCl)2或亚硫酰氯SOCl2处理(IId)而形成的。可替代地,在50℃-180℃之间的温度下,任选地在碱(如三乙胺)的存在下,在惰性溶剂(如吡啶或四氢呋喃THF)中,用例如1-乙基-3-(3-二甲基氨基丙基)碳二亚胺EDC或二环己基碳二亚胺DCC处理具有式(IId)的化合物将产生活化物质(XII)(其中X0分别是X01或X02);此类具有式Iif的活化的中间体可以与亲核试剂(例如具有式HNR101R012的胺,其中R101和R102是氢或C1-C6烷基,或HOR103,其中R103是C1-C6烷基)任选地在碱(例如三乙胺、吡啶或DMAP)的存在下,在惰性溶剂(例如CH2Cl2、THF或乙腈)中进行反应,以分别给出具有式Iig的化合物和具有式Iih的化合物。此类反应是本领域技术人员熟知的。氰基环丙基的后转化在方案6中说明。
方案6
具有式II的化合物(其中Q为Q1,定义具有式II-Q1的化合物,
其中R1、R3、R4、X1、G1和G2如在式I中所定义)可以如在方案7中所示的进行制备。
方案7
如在方案7中所示,具有式II-Q1的化合物可以通过使具有式(XIV)的化合物(其中R1、R3、R4、A、X1、G1和G2如在式I中所定义)环化而制备,例如通过在乙酸或三氟乙酸(优选地当X1是NR5时,其中R5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。也可以在25℃-180℃(优选100℃-170℃)之间的温度下,在惰性溶剂(如N-甲基吡咯烷酮、甲苯或二甲苯)中,在酸催化剂(例如甲磺酸或对甲苯磺酸p-TsOH)的存在下实现具有式(XIV)的化合物的环化。此类方法先前已经描述于例如WO 2016096584中。可替代地,可以在20℃-50℃之间的温度下,在惰性溶剂(如四氢呋喃THF)中,使用三苯基膦、二异丙基偶氮二甲酸酯(或二乙基偶氮二甲酸酯)将具有式(XIV)的化合物转化成具有式II-Q1的化合物(优选地当X1是O时)。先前已经针对这些转化描述了此类光延反应条件(参见WO 2009/131237和WO 2016/121997)。
具有式(XIV)的化合物(其中R1、R3、R4、A、X1、G1和G2如式I所定义)可以经由通过以下进行的酰化制备;
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(其中R1、R3和A如式I中所定义)活化,以形成活化物质(XII),其中R1、R3和A如式I中所定义,并且其中X0是卤素,优选氯。例如,化合物(XII)(其中X0是卤素,优选氯)是通过在20℃至100℃之间(优选25℃)的温度下,在惰性溶剂(如二氯甲烷CH2Cl2或四氢呋喃THF)中,在催化量的N,N-二甲基甲酰胺DMF的存在下,用例如草酰氯(COCl)2或亚硫酰氯SOCl2处理(XIII)而形成的。可替代地,在50℃-180℃之间的温度下,任选地在碱(如三乙胺)的存在下,在惰性溶剂(如吡啶或四氢呋喃THF)中,用例如1-乙基-3-(3-二甲基氨基丙基)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X0分别是X01或X02);随后
ii)在0℃与50℃之间的温度下,在惰性溶剂(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,在碱(如三乙胺、N,N-二异丙基乙胺或吡啶)的存在下,用具有式(XI)的化合物(其中X1、G1、G2和R4是如在式I中所定义的)处理活化物质(XII)以形成具有式(XIV)的化合物。具有式XIII的化合物(其中R3是H,即化合物,其中是R1是乙基,R3是H且A是N或CH)是已知的并且描述于WO 2017146226、或WO2016121997(对于5-环丙基-3-乙基硫烷基-吡啶-2-甲酸)、CAS[1975148-58-3]、和WO2016023954(对于4-环丙基-2-乙基硫烷基-苯甲酸)、CAS[1879052-58-0]中。具有式XIII的化合物(其中R3是氰基,R1是乙基且A是CH(4-(1-氰基环丙基)-2-乙基硫烷基-苯甲酸,CAS[2225113-79-9]))和具有式XIII的化合物(其中R3是氰基,R1是乙基且A是N(5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-甲酸,CAS[2225113-77-7]))是已知的并且描述于WO 2018/077565中。
具有式(XI)的化合物(其中X1、G1、G2和R2如式I中所定义)先前已在例如WO 2012/086848、WO 2015/000715和WO 2016/116338中描述。
具有式II的化合物,其中Q为Q2,定义具有式II-Q2的化合物,
其中R1、R3、R4、A和G2如在式I中所定义,
方案8
可通过以下方式制备(方案8):使具有式(XVI)的化合物(其中R1、R3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(XVI)的化合物(其中G2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于例如WO 2012/49280或WO 2003/031587中。具有式(XV)的化合物(其中G2和R2如式I中所定义)或者是已知化合物,可商购获得,或者可通过本领域技术人员已知的已知方法制备。
具有式(XVI)的化合物(其中R1、R3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9
可以通过通常在溶剂(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℃和150℃之间(优选在室温和120℃之间)的温度下,任选地在微波加热条件下,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、Br2/乙酸、PhNMe3 +Br3 -)处理具有式(XVIII)的化合物(其中R1、R3和A如式I中所定义)制备(方案9)。此类方法先前已经描述于例如WO 2016/071214中。
具有式(XVIII)的化合物(其中R1、R3和A如式I中所定义)可以通过使具有式(XVII)的化合物(其中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)),在上文已描述的条件下(参见方案5,化合物IV转化为IIb)进行反应来制备。
具有式(XVII)的化合物(其中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),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(例如在WO 2016/071214)中描述的已知方法制备。
可替代地,具有式II的化合物(其中Q为Q5),定义具有式II-Q5的化合物(其中R1、R3、R4、R6和A如在式I中所定义),
方案9a:
可以通过在上文已描述的条件(参见方案7,将化合物(XIV)转化为II-Q1)下环化具有式(XXa)的化合物(其中R1、R3、R4、R5、R6和A如式I中所定义)或具有相同的取代基定义的具有式(XXb)的区域异构体,或其任何比例的混合物来制备(方案9a)。
具有式(XXa)的化合物(其中R1、R3、R4、R5、R6和A如式I中所定义),或具有相同取代基定义的具有式(XXb)的区域异构体,或其任何比例的混合物可以通过在上文已经描述的条件(参见方案7,将化合物(XII)和(XIII)转化为化合物(XIV))下,用具有式(XIX)的化合物(其中R4、R5和R6如式I中所定义)处理上述活化物质(XII)来制备。
具有式(XIX)的化合物(其中R4、R5和R6如式I中所定义)先前已在例如WO 2016/023954、WO 2016/142326、WO 2017/133994和WO 2018077565中描述。
可替代地,具有式II的化合物(其中Q为Q3),定义具有式II-Q3的化合物(其中R1、R4、R3和A如在式I中所定义),
方案10
可以通过在惰性溶剂(例如乙醇、甲苯或乙腈)中,任选地在合适的碱(例如碳酸钠、碳酸钾或碳酸铯(或碳酸氢钠或碳酸氢钾))或氧化镁存在下,在80和150℃之间的温度下,任选地在微波加热条件下,使上述具有式(XVI)的化合物(其中R1、R3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))与具有式(XXI)的化合物(其中R4如式I中所定义)缩合来制备(方案10)。此类方法先前已经描述于例如WO 2011/074658中。具有式(XXI)的化合物(其中R4是如式I中所定义的)或者是已知的化合物、可商购的或可通过本领域技术人员已知的已知方法制备(参见例如WO 2011/074658和WO 2010/083145)。
具有式II的化合物,其中Q为Q4,定义具有式II-Q4的化合物,
其中R1、R3、R4、G1、G2和A如在式I中所定义,
方案11
也可以在促进N2排出的热解条件下,经由具有式(XXV)的化合物(其中R1、R4、R7、R8、A、G1、G2和R2如在式I中所定义)的叠氮基亚胺的N-N键形成反应来制备(方案11)。可替代地,该反应可以在金属催化剂(例如Cu(I)催化剂,如CuI,CuBr,CuCl或CuCN)的存在下,或更普遍地与过渡金属与配体例如四甲基乙二胺、2,2'-联吡啶或1,10-菲咯啉组合进行。合适的溶剂可包括在室温与200℃之间、优选在100℃至160℃之间的温度下,任选在微波加热条件下,使用甲苯、氯苯或二甲苯。这类还原环化反应条件描述于例如Organic Letters[有机快报],2011,第13卷,第13期,3542-3545和US2017/0260183中,
可通过通常在室温和200℃之间(优选40和160℃之间)的温度下加热,任选地在微波加热条件下,在合适的溶剂(可以包括例如甲苯或二甲苯)中的具有式(XXIII)的化合物(其中R1、R3和A如式I中所定义)和具有式(XXIV)的化合物(其中G1、G2和R4如式I中所定义)之间的反应制备具有式(XXV)的化合物(其中R1、R3、R4、G1、G2和A如式I中所定义)。具有式(XXV)的化合物的形成可需要通过共沸蒸馏或用干燥剂(例如像TiCl4或分子筛)来除去水。具有式(XXV)的席夫碱的这种形成是本领域技术人员已知的,并且描述于例如WO 2017/134066中。在文献中报道了具有式XXIV的化合物(参见在WO 2018/052136中报道的CAS 2211908-96-0)。
具有式XXIII化合物可以通过使具有式XXII的化合物在酸(例如HCl、H2SO4、H3PO4、HNO3、TFA)的存在下反应来制备。此类N连接的氨基甲酸酯的脱保护反应是本领域技术人员所熟知的,并且描述于例如RSC Advances[英国皇家化学学会期刊],5(5),3200-3205;2015中。
具有式XXII的化合物可以通过在合适的碱存在下,并且存在或不存在路易斯酸和溶剂下,在50℃与200℃之间的温度下,使具有式XIII的化合物与有机叠氮化物或氨衍生物(例如NH4OH、NH3、NH2Boc)反应来制备。有机叠氮化物的实例包括TMSN3、叠氮化钠、二苯基磷酰基叠氮化物或甲苯磺酰基叠氮化物并且合适的溶剂可以是t-BuOH、甲苯、二甲苯、THF或乙腈。合适的路易斯酸的实例可以包括Zn(OTf)2。此类将羧酸转化为胺的反应是以名称库尔修斯(Curtius)反应被本领域技术人员所熟知的,并报道于Org.Lett.[有机快报],2005,7,4107-4110;Journal of Medicinal Chemistry[药物化学杂志],49(12),3614-3627;2006。
可替代地,具有式II-Q4的化合物(其中R1、R3、R4、G1、G2和A是如式I所定义的)可以通过使具有式(XXVI)的化合物(其中R4、G1、G2是如式I所定义的,并且其中LG是离去基团(例如像氯、溴或碘(优选氯或溴),或芳基-、烷基-或卤代烷基磺酸酯(如三氟甲磺酸酯))与具有式(XXVII)的化合物(其中G1、G2和R4是如式I所定义的),在碱(例如像碳酸铯、碳酸钠、碳酸钾或碳酸锂,或氢化钠)的存在下,任选地在金属催化剂(如碘化铜(I)或钯催化剂)的存在下,有或没有添加剂(如L-脯氨酸、N,N’-二甲基乙二胺或基于磷的配体)情况下,在惰性溶剂(如乙腈、N,N-二甲基甲酰胺、N-甲基-2-吡咯烷酮或二甲亚砜)中,在室温与200℃之间的温度下,任选地在微波加热条件下反应来制备。此类芳香族亲核取代反应条件描述于,例如WO 2017/134066中。具有式XXVII的化合物可以通过桑德迈尔(Sandmeyer)反应(即用NaNO2或tBu-ONO在惰性溶剂(例如t-BuOH或水)中将化合物XXIII重氮化,随后添加无机卤化物(例如CuBr2、CuCl,或KI))来获得。此类桑德迈尔反应在文献(参见例如Synthesis[合成],2007,2534-2538,Org.Lett.[有机快报],2008,10,3961-3964)和其中引用的参考文献中是熟知的。
这些反应物可以在碱的存在下进行反应。适合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、游离的或N-烷基化的饱和或不饱和的环烷基胺、碱性杂环、氢氧化铵以及碳环胺。可以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、二异丙氨基锂、双(三甲基硅烷基)酰胺钾、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-二甲胺、N,N-二乙苯胺、吡啶、4-(N,N-二甲基氨基)吡啶、奎宁环、N-甲基吗啉、苄基三甲基铵氢氧化物以及1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)。
这些反应物可以按照原样彼此进行反应,即:不添加溶剂或稀释剂。然而,在大多数情况下,加入惰性溶剂或稀释剂或这些的混合物是有利的。如果该反应在碱的存在下进行,那么这些过量使用的碱(如三乙胺、吡啶、N-甲基吗啉或N,N-二乙苯胺)还可以充当溶剂或稀释剂。
所述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根据本发明的其他取代基来替代。
具有式I的化合物的盐能以本身已知的方式来制备。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适合的离子交换剂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适合的离子交换剂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(例如通过用适合的碱性化合物或用适合的离子交换剂试剂进行处理)以及与碱的盐(例如通过用适合的酸或用适合的离子交换剂试剂进行处理)。
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,例如转化成其他酸加成盐,例如通过在适合的溶剂中用酸的适合的金属盐(如钠、钡或银的盐,例如用乙酸银)来处理无机酸的盐(如盐酸盐),在该溶剂中,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,具有成盐特性的这些具有式I的化合物能以游离形式或盐的形式获得。
取决于分子中存在的不对称碳原子的数目、绝对和相对构型和/或取决于分子中存在的非芳香族双键的构型,具有式I的化合物和适当时其互变异构体(在每种情况下呈游离形式或呈盐形式)可以以可能的异构体之一的形式或作为这些的混合物存在,例如以纯异构体的形式,如对映体和/或非对映体,或作为异构体混合物,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;本发明涉及纯异构体以及还有所有可能的异构体混合物,并且在上文和下文中在每种情况下都应如此理解,即使立体化学细节未在每种情况下明确提及。
呈游离形式或呈盐形式的具有式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/或色谱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色谱法,例如在乙酰纤维素上的高效液相色谱法(HPLC);借助于适合的微生物,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,其中仅一个对映异构体被络合;或通过转化成非对映异构体的盐,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,从该非对映异构体可以通过适合的试剂(例如碱性试剂)的作用使所希望的对映异构体变成游离的。
纯的非对映异构体或对映异构体能根据本发明来获得,不仅是通过分离适合的异构体混合物,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用具有适合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,例如从J.Med.Chem.[药物化学杂志],32(12),2561-73,1989或WO 2000/15615中是已知的。
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(在每种情况下呈游离形式或呈盐形式)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。
以下根据下表Y-1至Y-8、X-1至X-8、U-1至U-2和V-1至V-6的具有式I的化合物可以根据上述方法制备。以下实例旨在说明本发明并且示出优选的具有式I的化合物。
表Y-1至Y-8是指具有以下式的化合物
表Z:R3和R4的取代基定义:
索引 | R<sub>4</sub> | R3 |
1 | CF<sub>3</sub> | CN |
2 | SCF<sub>3</sub> | CN |
3 | SO<sub>2</sub>CF<sub>3</sub> | CN |
4 | CF<sub>3</sub> | H |
5 | SCF<sub>3</sub> | H |
6 | SO<sub>2</sub>CF<sub>3</sub> | H |
7 | CF<sub>3</sub> | CONH<sub>2</sub> |
8 | SCF<sub>3</sub> | CONH<sub>2</sub> |
表Y-1提供了8种具有式IaY的化合物Y-1.001至Y-1.008,其中A是CH,G1是CH,G2是CH,并且R3、R4如在表Z中所定义。
例如,化合物Y-1.001具有以下结构;
表Y-2提供了8种具有式IaY的化合物Y-2.001至Y-2.008,其中A是CH,G1是CH,G2是N,并且R3、R4如在表Z中所定义。
例如,化合物Y-2.001具有以下结构;
表Y-3提供了8种具有式IaY的化合物Y-3.001至Y-3.008,其中A是CH,G1是N,G2是CH,并且R3、R4如在表Z中所定义。
例如,化合物Y-3.001具有以下结构;
表Y-4提供了8种具有式IaY的化合物Y-4.001至Y-4.008,其中A是CH,G1是N,G2是N,并且R3、R4如在表Z中所定义。
例如,化合物Y-4.001具有以下结构;
表Y-5提供了8种具有式IaY的化合物Y-5.001至Y-5.008,其中A是N,G1是CH,G2是CH,并且R3、R4如在表Z中所定义。
例如,化合物Y-5.001具有以下结构;
表Y-6提供了8种具有式IaY的化合物Y-6.001至Y-6.008,其中A是N,G1是CH,G2是N,并且R3、R4如在表Z中所定义。
例如,化合物Y-6.001具有以下结构;
表Y-7提供了8种具有式IaY的化合物Y-7.001至Y-7.008,其中A是N,G1是N,G2是CH,并且R3、R4如在表Z中所定义。
例如,化合物Y-7.001具有以下结构;
表Y-8提供了8种具有式IaY的化合物Y-8.001至Y-8.008,其中A是N,G1是N,G2是N,并且R3、R4如在表Z中所定义。
例如,化合物Y-8.001具有以下结构;
表X-1至X-8是指具有以下式的化合物
表X-1提供了8种具有式Iax的化合物X-1.001至X-1.008,其中A是CH,G1是CH,G2是CH,并且R3、R4如在表Z中所定义。
例如,化合物X-1.001具有以下结构;
表X-2提供了8种具有式Iax的化合物X-2.001至X-2.008,其中A是CH,G1是CH,G2是N,并且R3、R4如在表Z中所定义。
表X-3提供了8种具有式Iax的化合物X-3.001至X-3.008,其中A是CH,G1是N,G2是CH,并且R3、R4如在表Z中所定义。
表X-4提供了8种具有式Iax的化合物X-4.001至X-4.008,其中A是CH,G1是N,G2是N,并且R3、R4如在表Z中所定义。
表X-5提供了8种具有式Iax的化合物X-5.001至X-5.008,其中A是N,G1是CH,G2是CH,并且R3、R4如在表Z中所定义。
表X-6提供了8种具有式Ib的化合物X-6.001至X-6.008,其中A是N,G1是CH,G2是N,并且R3、R4如在表Z中所定义。
表X-7提供了8种具有式Ib的化合物X-7.001至X-7.008,其中A是N,G1是N,G2是CH,并且R3、R4如在表Z中所定义。
表X-8提供了8种具有式Ib的化合物X-8.001至X-8.008,其中A是N,G1是N,G2是N,并且R3、R4如在表Z中所定义。
下表V-1至V-6说明了具体的具有式I的本发明的化合物(其中R2是H,且n是1)。
表V-1提供了9种具有式I的化合物V-1.001至V-1.009,其中是A是CH,R3是CN,并且Q如在表W中所定义。
表W:Q的取代基定义:
例如化合物V-1.002具有以下结构:
表V-2提供了9种具有式I的化合物V-2.001至V-2.009,其中A是N,R3是CN,并且Q如在表W中所定义。
例如化合物V-2.005具有以下结构:
表V-3提供了9种具有式I的化合物V-3.001至V-3.009,其中A是CH,R3是H,并且Q如在表W中所定义。
例如化合物V-3.008具有以下结构:
表V-4提供了9种具有式I的化合物V-4.001至V-4.009,其中A是N,R3是H,并且Q如在表W中所定义。
例如化合物V-4.001具有以下结构:
表V-5提供了9种具有式I的化合物V-5.001至V-5.009,其中A是CH,R3是CONH2,并且Q如在表W中所定义。
例如化合物V-5.007具有以下结构:
表V-6提供了9种具有式I的化合物V-6.001至V-6.009,其中A是N,R3是CONH2,并且Q如在表W中所定义。
例如化合物V-6.006具有以下结构:
表U-1至U-2是指具有以下式的化合物
表U-1提供了8种具有式IaU的化合物U-1.001至U-1.008,其中A是CH,并且R3、R4如在表Z中所定义。
例如,化合物U-1.001具有以下结构;
表U-2提供了8种具有式IaU的化合物U-2.001至U-2.008,其中A是N,并且R3、R4如在表Z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性动物有害生物(如昆虫、软体动物、线虫或蜱螨目的代表)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、杀软体动物、杀线虫或杀螨活性可以本身直接显示,即立即或者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;或间接显示,例如降低产卵和/或孵化率,至少50%至60%的对应于破坏率(死亡率)的良好活性。
根据本发明的具有式(I)的化合物可以具有任何数量的益处,尤其包括对于保护植物抵抗昆虫的有利水平的生物活性或对于用作农用化学品活性成分的优越特性(例如,更高的生物活性、有利的活性谱、增加的安全性、改进的物理-化学特性、或增加的生物可降解性或环境特征曲线)。具体而言,已经出人意料地发现某些具有式(I)的化合物相对于非靶标生物体,例如非靶标节肢动物,特别是传粉者(如蜜蜂、独居蜂和熊蜂)显示出有利的安全性。最特别地,相对于意大利蜂(Apis mellifera)。
在此方面,本发明的具有式(I)的某些化合物与已知的化合物的区别可以在于在低施用率下更大的效力,这可以由本领域技术人员使用与生物学实例中概述的那些类似的或改编自生物学实例中概述的那些的实验程序,使用更低的施用率(如果必要的话)例如,50ppm、12.5ppm、6ppm、3ppm、1.5ppm、0.8ppm或0.2ppm来证实。
此外,已经出人意料地发现,具有式(I)的化合物示出了用于作物保护应用的有利的物理化学特性,特别是降低的熔点、降低的亲油性和增加的水溶性。已经发现这种特性对于植物吸收和全身分布是有利的,参见例如A.Buchholz,S.Trapp,有害生物管理学(PestManag Sci)2016;72:929-939)以控制下面列出的某些有害生物种类。
上述动物有害生物的实例是:
来自蜱螨目,例如
下毛瘿螨属物种(Acalitus spp.)、针刺瘿螨属物种(Aculus spp)、窄瘿螨属物种(Acaricalus spp.)、瘤瘿螨属物种(Aceria spp.)、粗脚粉螨(Acarus siro)、钝眼蜱属物种(Amblyomma spp.)、锐缘蜱属物种(Argas spp.)、牛蜱属物种(Boophilus spp.)、短须螨属物种(Brevipalpus spp.)、苔螨属物种(Bryobia spp)、上三脊瘿螨属物种(Calipitrimerus spp.)、皮螨属物种(Chorioptes spp.)、鸡皮刺螨(Dermanyssusgallinae)、表皮螨属物种(Dermatophagoides spp)、始叶螨属物种(Eotetranychus spp)、瘿螨属物种(Eriophyes spp.)、半跗线螨属物种(Hemitarsonemus spp)、璃眼蜱属物种(Hyalomma spp.)、硬蜱属物种(Ixodes spp.)、小爪螨属物种(Olygonychus spp)、钝缘蜱属物种(Ornithodoros spp.)、侧多食跗线螨(Polyphagotarsone latus)、全爪螨属物种(Panonychus spp.)、桔芸锈螨(Phyllocoptruta oleivora)、植食螨属物种(Phytonemusspp.)、多食跗线螨属物种(Polyphagotarsonemus spp)、痒螨属物种(Psoroptes spp.)、扇头蜱属物种(Rhipicephalus spp.)、根螨属物种(Rhizoglyphus spp.)、疥螨属物种(Sarcoptes spp.)、狭跗线螨属物种(Steneotarsonemus spp)、跗线螨属物种(Tarsonemusspp.)以及叶螨属物种(Tetranychus spp.);
来自虱目,例如
血虱属物种(Haematopinus spp.)、长颚虱属物种(Linognathus spp.)、人虱属物种(Pediculus spp.)、瘿绵蚜属物种(Pemphigus spp.)以及根瘤蚜属物种(Phylloxeraspp.);
来自鞘翅目,例如
叩甲属物种(Agriotes spp.)、欧洲鳃角金龟(Amphimallon majale)、东方异丽金龟(Anomala orientalis)、花象属物种(Anthonomus spp.)、蜉金龟属物种(Aphodiusspp)、玉米拟花萤(Astylus atromaculatus)、金龟属物种(Ataenius spp)、甜菜隐食甲(Atomaria linearis)、甜菜胫跳甲(Chaetocnema tibialis)、萤叶甲属物种(Cerotomaspp)、宽胸叩头虫属物种(Conoderus spp)、根颈象属物种(Cosmopolites spp.)、绿花金龟(Cotinis nitida)、象虫属物种(Curculio spp.)、圆头犀金龟属物种(Cyclocephalaspp)、皮蠹属物种(Dermestes spp.)、根萤叶甲属物种(Diabrotica spp.)、阿根廷兜虫(Diloboderus abderus)、食植瓢虫属物种(Epilachna spp.)、Eremnus属物种、黑异爪蔗金龟(Heteronychus arator)、咖啡果小蠹(Hypothenemus hampei)、Lagria vilosa、马铃薯甲虫(Leptinotarsa decemlineata)、稻水象属物种(Lissorhoptrus spp.)、Liogenys属物种、Maecolaspis属物种、栗色绒金龟(Maladera castanea)、美洲叶甲属物种(Megascelisspp)、油菜花露尾甲(Melighetes aeneus)、鳃金龟属物种(Melolontha spp.)、Myochrousarmatus、锯谷盗属物种(Orycaephilus spp.)、耳喙象属物种(Otiorhynchus spp.)、鳃角金龟属物种(Phyllophaga spp.)、斑象属物种(Phlyctinus spp.)、弧丽金龟属物种(Popillia spp.)、蚤跳甲属物种(Psylliodes spp.)、Rhyssomatus aubtilis、劫根蠹属物种(Rhizopertha spp.)、金龟子科(Scarabeidae)、米象属物种(Sitophilus spp.)、麦蛾属物种(Sitotroga spp.)、伪切根虫属物种(Somaticus spp.)、尖隐喙象属物种、大豆茎象(Sternechus subsignatus)、拟步行虫属物种(Tenebrio spp.)、拟谷盗属物种(Triboliumspp.)以及斑皮蠹属物种(Trogoderma spp.);
来自双翅目,例如
伊蚊属物种(Aedes spp.)、疟蚊属物种(Anopheles spp)、高粱芒蚊(Antherigonasoccata.)、橄榄果实蝇(Bactrocea oleae)、花园毛蚊(Bibio hortulanus)、迟眼蕈蚊属物种(Bradysia spp.)、红头丽蝇(Calliphora erythrocephala)、小条实蝇属物种(Ceratitis spp.)、金蝇属物种(Chrysomyia spp.)、库蚊属物种(Culex spp.)、黄蝇属物种(Cuterebra spp.)、寡鬃实蝇属物种(Dacus spp.)、地种蝇属物种(Delia spp)、黑腹果蝇(Drosophilamelanogaster)、厕蝇属物种(Fannia spp.)、胃蝇属物种(Gastrophilusspp.)、Geomyza tripunctata、舌蝇属物种(Glossina spp.)、皮蝇属物种(Hypodermaspp.)、虱蝇属物种(Hyppobosca spp.)、斑潜蝇属物种(Liriomyza spp.)、绿蝇属物种(Lucilia spp.)、黑潜蝇属物种(Melanagromyza spp.)、家蝇属物种(Musca spp.)、狂蝇属物种(Oestrus spp.)、瘿蚊属物种(Orseolia spp.)、瑞典麦秆蝇(Oscinella frit)、藜泉蝇(Pegomyia hyoscyami)、草种蝇属物种(Phorbia spp.)、绕实蝇属物种(Rhagoletisspp)、Rivelia quadrifasciata、Scatella属物种、尖眼蕈蚊属物种(Sciara spp.)、螫蝇属物种(Stomoxys spp.)、虻属物种(Tabanus spp.)、绦虫属物种(Tannia spp.)以及大蚊属物种(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(Euschistus spp.)、六斑菜蝽(Eurydema pulchrum)、扁盾蝽属、茶翅蝽、具凹巨股长蝽(Horcias nobilellus)、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);
豌豆无网长管蚜(Acyrthosium pisum)、Adalges属物种、Agalliana ensigera、塔尔吉隆脉木虱、粉虱属物种(Aleurodicus spp.)、刺粉虱属物种(Aleurocanthus spp.)、甘蔗穴粉虱、软毛粉虱(Aleurothrixus floccosus)、甘蓝粉虱(Aleyrodes brassicae)、棉叶蝉(Amarasca biguttula)、檬果长突叶蝉、肾圆盾蚧属物种、蚜科、蚜属物种、圆盾蚧属物种(Aspidiotus spp.)、茄沟无网蚜、马铃薯/番茄木虱(Bactericera cockerelli)、小粉虱属物种、短尾蚜属物种(Brachycaudus spp.)、甘蓝蚜、喀木虱属物种、双尾蚜(Cavariellaaegopodii Scop.)、蜡蚧属物种、黑褐圆盾蚧、橙褐圆盾蚧、大叶蝉属物种、大白叶蝉(Cofana spectra)、隐瘤蚜属物种、叶蝉属物种、褐软蚧、玉米黄翅叶蝉、裸粉虱属物种、柑橘木虱、麦双尾蚜、西圆尾蚜属物种、小绿叶蝉属物种、苹果绵蚜、葡萄斑叶蝉属物种、Gascardia属物种、赤桉木虱(Glycaspis brimblecombei)、菜缢管蚜(Hyadaphispseudobrassicae)、大尾蚜属物种(Hyalopterus spp.)、超瘤蚜种(Hyperomyzuspallidus)、檬果绿叶蝉(Idioscopus clypealis)、非洲叶蝉、灰飞虱属物种、水土坚蚧、蛎盾蚧属物种、萝卜蚜(Lopaphis erysimi)、Lyogenys maidis、长管蚜属物种、沫蝉属物种、蛾蜡蝉科(Metcalfa pruinosa)、麦无网蚜、麦蜡蝉、瘤蚜属物种、新声蚜属物种(Neotoxoptera sp)、黑尾叶蝉属物种、褐飞虱属物种(Nilaparvata spp.)、梨大绿蚜、Odonaspis ruthae、甘蔗棉蚜、杨梅缘粉虱、考氏木虱、片盾蚧属物种、瘿绵蚜属物种、玉米蜡蝉、扁角飞虱属物种、忽布疣蚜、根瘤蚜属物种(Phylloxera spp)、动性球菌属物种、桑白盾蚧属物种、粉蚧属物种、棉跳盲蝽(Pseudatomoscelis seriatus)、木虱属物种、棉蚧(Pulvinaria aethiopica)、齿盾蚧属物种、Quesada gigas、电光叶蝉(Reciliadorsalis)、缢管蚜属物种、黑盔蚧属物种、带叶蝉属物种、二叉蚜属物种、麦蚜属物种(Sitobion spp.)、白背飞虱、三角苜蓿跳虫(Spissistilus festinus)、条斑飞虱(Tarophagus Proserpina)、声蚜属物种、粉虱属物种、Tridiscus sporoboli、葵粉蚧属物种(Trionymus spp.)、非洲木虱、矢尖蚧、火焰斑叶蝉、Zyginidia scutellaris;
来自膜翅目,例如
顶切叶蚁属(Acromyrmex)、三节叶蜂属物种(Arge spp.)、切叶蚁属物种(Attaspp.)、茎叶蜂属物种(Cephus spp.)、松叶蜂属物种(Diprion spp.)、锯角叶蜂科(Diprionidae)、松叶蜂(Gilpinia polytoma)、实叶蜂属物种(Hoplocampa spp.)、毛蚁属物种(Lasius spp.)、小黄家蚁(Monomorium pharaonis)、新松叶蜂属物种(Neodiprionspp.)、农蚁属物种(Pogonomyrmex spp)、红火蚁、水蚁属物种(Solenopsis spp.)以及胡蜂属物种(Vespa spp.);
来自等翅目,例如
家白蚁属物种(Coptotermes spp)、白蚁(Corniternes cumulans)、楹白蚁属物种(Incisitermes spp)、大白蚁属物种(Macrotermes spp)、澳白蚁属物种(Mastotermesspp)、小白蚁属物种(Microtermes spp)、散白蚁属物种(Reticulitermes spp.);热带火蚁(Solenopsis geminate)
来自鳞翅目(Lepidoptera),例如,
长翅卷蛾属物种、褐带卷蛾属物种、透翅蛾属物种、地夜蛾属物种、棉叶虫、Amylois属物种、黎豆夜蛾、黄卷蛾属物种、银蛾属物种(Argyresthia spp.)、带卷蛾属物种、丫纹夜蛾属物种、棉潜蛾、玉米楷夜蛾、粉斑螟蛾、桃蛀果蛾、禾草螟属物种、色卷蛾属物种、越蔓桔草螟(Chrysoteuchia topiaria)、葡萄果蠹蛾、卷叶螟属物种、云卷蛾属物种、纹卷蛾属物种、鞘蛾属物种、篱笆豆粉蝶(Colias lesbia)、小造桥夜蛾(Cosmophila flava)、草螟属物种、大菜螟、苹果异形小卷蛾、黄杨木蛾、小卷蛾属物种、黄杨绢野螟、杆草螟属物种、苏丹棉铃虫、钻夜蛾属物种、甘薯杆螟、粉斑螟属物种、叶小卷蛾属物种(Epinotiaspp.)、盐泽灯蛾(Estigmene acrea)、Etiella zinckinella、花小卷蛾属物种、环针单纹卷蛾、黄毒蛾属物种、切根虫属物种、Feltia jaculiferia、小食心虫属物种(Grapholitaspp.)、云雾广翅小卷蛾、实夜蛾属物种、菜螟、切叶野螟属物种(Herpetogramma spp.)、美国白蛾、番茄蠹蛾、Lasmopalpus lignosellus、旋纹潜叶蛾、潜叶细蛾属物种、葡萄花翅小卷蛾、Loxostege bifidalis、毒蛾属物种、潜蛾属物种、幕枯叶蛾属物种(Malacosomaspp.)、甘蓝夜蛾、烟草天蛾、光腹夜蛾属物种(Mythimna spp.)、夜蛾属物种、秋尺蛾属物种、Orniodes indica、欧洲玉米螟、超小卷蛾属物种、褐卷蛾属物种、小眼夜蛾、蛀茎夜蛾、红铃麦蛾、咖啡潜叶蛾、一星黏虫、马铃薯麦蛾、菜粉蝶、粉蝶属物种、小菜蛾、小白巢蛾属物种、尺叶蛾属物种、薄荷灰夜蛾(Rachiplusia nu)、西方豆地香(Richia albicosta)、白禾螟属物种(Scirpophaga spp.)、蛀茎夜蛾属物种、长须卷蛾属物种、灰翅夜蛾属物种、棉大卷叶螟、兴透翅蛾属物种、异舟蛾属物种、卷蛾属物种、粉纹夜蛾、番茄斑潜蝇、以及巢蛾属物种;
来自食毛目(Mallophaga),例如,
畜虱属物种(Damalinea spp.)和啮毛虱属物种(Trichodectes spp.);
来自直翅目(Orthoptera),例如,
蠊属物种(Blatta spp.)、小蠊属物种(Blattella spp.)、蝼蛄属物种(Gryllotalpa spp.)、马德拉蜚蠊(Leucophaea maderae)、飞蝗属物种(Locusta spp.)、北痣蟋蟀(Neocurtilla hexadactyla)、大蠊属物种(Periplaneta spp.)、痣蟋蟀属物种(Scapteriscus spp.)、以及沙漠蝗属物种(Schistocerca spp.);
来自啮虫目(Psocoptera),例如,
虱啮属物种(Liposcelis spp.);
来自蚤目(Siphonaptera),例如,
角叶蚤属物种(Ceratophyllus spp.)、栉头蚤属物种(Ctenocephalides spp.)以及开皇客蚤(Xenopsylla cheopis);
来自缨翅目(Thysanoptera),例如,
Calliothrips phaseoli、花蓟马属物种(Frankliniella spp.)、阳蓟马属物种(Heliothrips spp)、褐带蓟马属物种(Hercinothrips spp.)、单亲蓟马属物种(Parthenothrips spp.)、非洲桔硬蓟马(Scirtothrips aurantii)、大豆蓟马(Sericothrips variabilis)、带蓟马属物种(Taeniothrips spp.)、蓟马属物种(Thripsspp);
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、即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;果实,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;柑橘类果实,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:藿香蓟属物种、假面花属物种(Alonsoa spp.)、银莲花属物种、南非葵(Anisodontea capsenisis)、春黄菊属物种、金鱼草属物种、紫菀属物种、秋海棠属物种(例如丽格海棠、四季秋海棠、球根秋海棠(B.tubéreux))、叶子花属物种、雁河菊属物种(Brachycome spp.)、芸苔属物种(观赏植物)、蒲包草属物种、辣椒、长春花、美人蕉属物种、矢车菊属物种、菊属物种、瓜叶菊属物种(银叶菊(C.maritime))、金鸡菊属物种、红景天(Crassula coccinea)、火红萼距花(Cupheaignea)、大丽花属物种、翠雀属物种、荷包牡丹、彩虹菊属物种(Dorotheantus spp.)、洋桔梗、连翘属物种、倒挂金钟属物种、老鹳草属鼠麹草属(Geranium gnaphalium)、大丁草属物种、千日红、天芥菜属物种、向日葵属物种、木槿属物种、绣球花属物种、绣球属物种、嫣红蔓、凤仙花属物种(非洲凤仙花)、血苋属物种(Iresines spp.)、伽蓝菜属物种、马缨丹、三月花葵、狮耳花、百合属物种、松叶菊属物种、沟酸浆属物种、美国薄荷属物种、龙面花属物种、万寿菊属物种、石竹属物种(康乃馨)、美人蕉属物种、酢浆草属物种、雏菊属物种、天竺葵属物种(盾叶天竺葵、马蹄纹天竺葵)、堇菜属物种(三色堇)、碧冬茄属物种、草夹竹桃属物种、香茶菜属物种(Plecthranthus spp.)、一品红属物种、爬山虎属物种(五叶爬山虎、爬山虎)、报春花属物种、毛茛属物种、杜鹃花属物种、蔷薇属物种(玫瑰)、黄雏菊属物种、非洲堇属物种、鼠尾草属物种、紫扇花(Scaevola aemola)、蛾蝶花(Schizanthuswisetonensis)、景天属物种、茄属物种、苏非尼亚矮牵牛属物种(Surfinia spp.)、万寿菊属物种、烟草属物种、马鞭草属物种、百日草属物种以及其他花坛植物。
例如,本发明可以用于任何以下蔬菜物种:葱属物种(大蒜、洋葱、A.oschaninii、韭葱、火葱、大葱)、茴香芹、旱芹(Apium graveolus)、芦笋、甜菜、芸苔属物种(甘蓝、大白菜、芜菁)、辣椒、鹰嘴豆、苦苣、菊苣属物种(菊苣、苦苣)、西瓜(Citrillus lanatus)、黄瓜属物种(黄瓜、甜瓜)、南瓜属物种(西葫芦、印度南瓜)、菜蓟属物种(Cyanara spp.)(朝鲜蓟、刺苞菜蓟)、野胡萝卜、茴香、金丝桃属物种、莴苣、番茄属物种(番茄、圣女果番茄)、薄荷属物种、罗勒、香芹、菜豆属物种(菜豆、荷包豆)、豌豆、萝卜、食用大黄、迷迭香属物种、鼠尾草属物种、黑婆罗门参(Scorzonera hispanica)、茄子、菠菜、新缬草属物种(莴苣缬草、V.eriocarpa)以及蚕豆。
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(Leptinotarsa)(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(Leptinotarsa)(优选地在马铃薯上)以及二化螟(优选地在水稻上)。
在另一方面中,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,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,如亚粒线虫属物种(Subanguina spp.)、根结线虫属物种(Hypsoperine spp.)、大刺环线虫属物种(Macroposthonia spp.)、矮化线虫属物种(Melinius spp.)、刻点胞囊属物种(Punctodera spp.)、以及五沟线虫属物种(Quinisulcius spp.)。
本发明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(Bradybaena fruticum));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,所述毒素是如已知例如来自于产毒素细菌,尤其是芽孢杆菌属的那些细菌。
可由此类转基因植物表达的毒素包括例如杀昆虫蛋白,例如来自蜡样芽孢杆菌或日本金龟子芽孢杆菌的杀昆虫蛋白;或者来自苏云金芽孢杆菌的杀昆虫蛋白,如δ-内毒素,例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或者营养期杀昆虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A;或细菌定植线虫的杀昆虫蛋白,例如光杆状菌属物种(Photorhabdus spp.)或致病杆菌属物种(Xenorhabdus spp.),诸如发光杆菌(Photorhabdus luminescens)、嗜线虫致病杆菌(Xenorhabdus nematophilus);由动物产生的毒素,诸如蝎毒素、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(agglutinin);蛋白酶抑制剂,诸如胰蛋白酶抑制剂、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),诸如蓖麻毒素、玉蜀黍-RIP、相思豆毒素、丝瓜籽毒蛋白、皂草毒素蛋白或异株泻根毒蛋白;类固醇代谢酶,如3-羟基类固醇氧化酶、蜕化类固醇-UDP-糖基-转移酶、胆固醇氧化酶、蜕化素抑制剂、HMG-COA-还原酶、离子通道阻断剂诸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 2002/15701)。截短的毒素,例如截短的Cry1Ab是已知的。在经修饰的毒素的情况下,天然存在的毒素的一个或多个氨基酸被置换。在这种氨基酸置换中,优选将非天然存在的蛋白酶识别序列插入毒素中,例如像在Cry3A055的情况下,一种组织蛋白酶-G-识别序列被插入Cry3A毒素中(参见WO 2003/018810)。
此类毒素或能够合成此类毒素的转基因植物的实例披露于例如EP-A-0 374 753、WO 1993/07278、WO 1995/34656、EP-A-0 427 529、EP-A-451 878以及WO 2003/052073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 1990/13651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。此类植物的实例是:(玉米品种,表达Cry1Ab毒素);YieldGard (玉米品种,表达Cry3Bb1毒素);YieldGard(玉米品种,表达Cry1Ab和Cry3Bb1毒素);(玉米品种,表达Cry9C毒素);Herculex(玉米品种,表达Cry1Fa2毒素和获得对除草剂草铵膦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)、CB Advantage(Bt11玉米螟(CB)性状)以及
此类转基因作物的另外的实例是:
1.Bt11玉米,来自先正达种子公司(Syngenta Seeds SAS),霍比特路(Chemin del'Hobit)27,F-31 790圣苏维尔(St.Sauveur),法国,登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达截短的Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt11玉米还转基因表达PAT酶以获得对除草剂草铵膦铵盐的耐受性。
2.Bt176玉米,来自先正达种子公司,霍比特路27,F-31 790圣苏维尔,法国,登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达Cry1Ab毒素,使之能抵抗欧洲玉米螟(玉米螟和粉茎螟)的侵袭。Bt176玉米还转基因表达酶PAT以获得对除草剂草铵膦铵盐的耐受性。
3.MIR604玉米,来自先正达种子公司,霍比特路27,F-31 790圣苏维尔,法国,登记号C/FR/96/05/10。通过转基因表达经修饰的Cry3A毒素使之具有昆虫抗性的玉米。此毒素是通过插入组织蛋白酶-G-蛋白酶识别序列而经修饰的Cry3A055。此类转基因玉米植物的制备描述于WO 2003/018810中。
4.MON 863玉米,来自孟山都欧洲公司(Monsanto Europe S.A.),270-272特弗伦大道(Avenue de Tervuren),B-1150布鲁塞尔,比利时,登记号C/DE/02/9。MON 863表达Cry3Bb1毒素,并且对某些鞘翅目昆虫有抗性。
5.IPC 531棉花,来自孟山都欧洲公司,270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/ES/96/02。
6.1507玉米,来自先锋海外公司(Pioneer Overseas Corporation),特德斯科大道(Avenue Tedesco),7B-1160布鲁塞尔,比利时,登记号C/NL/00/10。遗传修饰的玉米,表达蛋白质Cry1F以获得对某些鳞翅目昆虫的抗性,并且表达PAT蛋白质以获得对除草剂草丁膦铵的耐受性。
7.NK603×MON 810玉米,来自孟山都欧洲公司270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/GB/02/M3/03。通过将遗传修饰的品种NK603和MON 810杂交,由常规育种的杂交玉米品种构成。NK603×MON 810玉米转基因地表达由土壤杆菌属菌株CP4获得的蛋白质CP4 EPSPS,使之耐除草剂(含有草甘膦),以及还有由苏云金芽孢杆菌库尔斯塔克亚种获得的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)13,4058巴塞尔(Basel),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)。此类抗病原物质和能够合成此类抗病原物质的转基因植物的实例例如从EP-A-0 392 225、WO 1995/33818和EP-A-0 353 191是已知的。生产此类转基因植物的方法对于本领域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,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 1995/33818)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 2003/000906中所描述的)。
根据本发明的组合物的其他使用范围是保护所储存的物品和储存室以及保护原材料,如木材、纺织品、地板或建筑物,以及还在卫生领域中,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的侵害。
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底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(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,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底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底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(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,考虑了施用此类组合物以用于在基底上的有害生物的残留控制,所述基底是如处于网织品、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。
有待处理的基底(包括无纺物、织物或网织品)可以由天然纤维,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,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、WO2005/113886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,根据本发明的化合物尤其适合于对抗来自如上提及的鳞翅目和来自鞘翅目的钻木昆虫,尤其是对抗下表A和B中列出的钻木虫:
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。
本发明还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。
特别地,本发明可用于控制用草坪草的根部喂养的昆虫有害生物,所述昆虫有害生物包括蛴螬(如圆头犀金龟属物种(Cyclocephala spp.)(例如标记的金龟子、C.lurida)、Rhizotrogus属物种(例如欧洲金龟子,欧洲切根鳃金龟(R.majalis))、黄栌属物种(Cotinus spp.)(例如绿六月甲虫(Green June beetle)、绿六月花金龟(C.nitida))、弧丽金龟属物种(Popillia spp.)(例如日本甲虫、日本弧丽金龟(P.japonica))、鳃角金龟属物种(Phyllophaga spp.)(例如五月/六月甲虫)、金龟属物种(例如草坪草黑金龟(Blackturfgrass ataenius)、黑绒金龟)、绒毛金龟属物种(Maladera spp.)(例如亚洲花园甲虫(Asiatic garden beetle)、栗色绒金龟)以及Tomarus属物种)、地面珍珠(硕蚧属物种(Margarodes spp.))、蝼蛄(褐黄色的、南方的、以及短翅的;痣蟋蟀属物种(Scapteriscusspp.)、非洲蝼蛄(Gryllotalpa africana))以及大蚊幼虫(leatherjackets)(欧洲大蚊(European crane fly)、大蚊属物种(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),和常见粘虫一星黏虫(Pseudaletia unipuncta))、切根虫,象鼻虫(尖隐喙象属物种(Sphenophorusspp.),诸如S.venatus verstitus和牧草长喙象(S.parvulus))以及草地螟(如草螟属物种(Crambus spp.)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有效地对抗外寄生虫如硬蜱、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:血虱属物种、长颚虱属物种(Linognathus spp.)、人虱属物种以及阴虱属物种(Phtirus spp.)、管虱属物种。
食毛目:毛羽虱属物种、短羽虱属物种、鸭虱属物种、牛羽虱属物种、Werneckiella属物种、Lepikentron属物种、畜虱属物种、啮毛虱属物种以及猫羽虱属物种(Felicolaspp.)。
双翅目及长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属物种(Aedes spp.)、疟蚊属物种、库蚊属物种(Culex spp.)、蚋属物种(Simulium spp.)、真蚋属物种(Eusimulium spp.)、白蛉属物种(Phlebotomus spp.)、罗蛉属物种(Lutzomyiaspp.)、库蠓属物种(Culicoides spp.)、斑虻属物种(Chrysops spp.)、驼背虻属物种(Hybomitra spp.)、黄虻属物种(Atylotus spp.)、虻属物种(Tabanus spp.)、麻虻属物种(Haematopota spp.)、Philipomyia属物种、蜂虱蝇属物种(Braula spp.)、家蝇属物种(Musca spp.)、齿股蝇属物种(Hydrotaea spp.)、螫蝇属物种、黑角蝇属物种(Haematobiaspp.)、莫蝇属物种(Morellia spp.)、厕蝇属物种(Fannia spp.)、舌蝇属物种(Glossinaspp.)、丽蝇属物种(Calliphora spp.)、绿蝇属物种(Lucilia spp.)、金蝇属物种(Chrysomyia spp.)、污蝇属物种(Wohlfahrtia spp.)、麻蝇属物种(Sarcophaga spp.)、狂蝇属物种(Oestrus spp.)、皮蝇属物种(Hypoderma spp.)、胃蝇属物种(Gasterophilusspp.)、虱蝇属物种(Hippobosca spp.)、羊虱蝇属物种(Lipoptena spp.)和蜱蝇属物种(Melophagus spp.)。
蚤目(Siphonapterida),例如蚤属物种(Pulex spp.)、栉头蚤属物种、客蚤属物种(Xenopsylla spp.)、角叶蚤属物种。
异翅目(Heteropterida),例如臭虫属物种、锥鼻虫属物种、红猎蝽属物种、锥蝽属物种(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)以及夏柏拉蟑螂属物种(Supella spp.)。
蜱螨(Acaria)亚纲(螨科(Acarida))和后气门目(Meta-stigmata)和中气门目(Meso-stigmata),例如锐缘蜱属物种(Argas spp.)、钝缘蜱属物种(Ornithodorus spp.)、耳蜱属物种(Otobius spp.)、硬蜱属物种(Ixodes spp.)、钝眼蜱属物种(Amblyommaspp.)、牛蜱属物种(Boophilus spp.)、革蜱属物种(Dermacentor spp.)、血蜱属物种(Haemophysalis spp.)、璃眼蜱属物种(Hyalomma spp.)、扇头蜱属物种(Rhipicephalusspp.)、皮刺螨属物种(Dermanyssus spp.)、刺利螨属物种(Raillietia spp.)、肺刺螨属物种(Pneumonyssus spp.)、胸刺螨属物种(Sternostoma spp.)和瓦螨属物种(Varroaspp.)。
轴螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨目(Acaridida)(无气门亚目(Astigmata)),例如蜂盾螨属物种(Acarapis spp.)、姬螯螨属物种(Cheyletiellaspp.)、禽螯螨属物种(Ornithocheyletia spp.)、肉螨属物种(Myobia spp.)、疮螨属物种(Psorergates spp.)、蠕形螨属物种(Demodex spp.)、恙螨属物种(Trombicula spp.)、牦螨属物种(Listrophorus spp.)、粉螨属物种(Acarus spp.)、食酪螨属物种(Tyrophagusspp.)、嗜木螨属物种(Caloglyphus spp.)、颈下螨属物种(Hypodectes spp.)、翅螨属物种(Pterolichus spp.)、痒螨属物种(Psoroptes spp.)、皮螨属物种(Chorioptes spp.)、耳痒螨属物种(Otodectes spp.)、疥螨属物种(Sarcoptes spp.)、耳螨属物种(Notoedresspp.)、鸟疥螨属物种(Knemidocoptes spp.)、胞螨属物种(Cytodites spp.)以及鸡雏螨属物种(Laminosioptes spp.)。
根据本发明的组合物还适用于保护在如木材、纺织品、塑料、粘合剂、胶、漆料、纸张和卡片、皮革、地板和建筑等情况下的材料免受昆虫侵染。
根据本发明的组合物可用于,例如,对抗以下有害生物:甲虫,如北美家天牛(Hylotrupes bajulus)、长毛天牛(Chlorophorus pilosis)、家具窃蠹(Anobiumpunctatum)、红毛窃蠹(Xestobium rufovillosum)、梳角细脉窃蠹(Ptilinuspecticornis)、Dendrobium pertinex、松芽枝窃蠹(Ernobius mollis)、Priobium carpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(Lyctus africanus)、南方粉蠹(Lyctus planicollis)、栎粉蠹(Lyctus linearis)、柔毛粉蠹(Lyctus pubescens)、胸粉蠹(Trogoxylon aequale)、鳞毛粉蠹(Minthesrugicollis)、材小蠹属物种(Xyleborusspec.)、条木小蠹属物种(Tryptodendron spec.)、咖啡黑长蠹(Apate monachus)、槲长蠹(Bostrychus capucins)、棕异翅长蠹(Heterobostrychus brunneus)、双棘长蠢属物种(Sinoxylon spec.)以及竹长蠹(Dinoderus minutus),以及还有膜翅类,如蓝黑树蜂(Sirex juvencus)、大树蜂(Urocerus gigas)、泰加大树蜂(Urocerus gigas taignus)和Urocerus augu,以及白蚁类,如欧洲木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁(Cryptotermes brevis)、印巴结构木异白蚁(Heterotermes indicola)、黄胸散白蚁(Reticulitermes flavipes)、桑特散白蚁(Reticulitermes santonensis)、欧洲散白蚁(Reticulitermes lucifugus)、达尔文澳白蚁(Mastotermes darwiniensis)、内华达古白蚁(Zootermopsis nevadensis)与家白蚁(Coptotermes formosanus),以及蛀虫,如衣鱼(Lepisma saccharina)。
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辅助剂(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、泡腾球粒剂、可乳化的浓缩物、微可乳化浓缩物、水包油乳液、可流动油、水性分散体、油性分散体、悬乳液、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Manual on Development and Use of FAO and WHO Specifications forPesticides[关于杀有害生物剂的FAO和WHO标准的发展和使用的手册],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。可以用例如水、液体肥料、微量营养素、生物有机体、油或溶剂来进行稀释。
可以通过例如将活性成分与配制辅助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辅助剂(如精细分散固体、矿物油、植物或动物来源的油、改性的植物或动物来源的油、有机溶剂、水、表面活性物质或其组合)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释放(例如,缓慢释放)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适合溶液的形式。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组合物的配制辅助剂本身是已知的。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、经研磨的胡桃壳、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;磺基琥珀酸二烷基酯的盐,如二(2-乙基己基)磺基琥珀酸钠;山梨糖醇酯,如山梨糖醇油酸酯;季铵,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;以及磷酸单烷基酯和二烷基酯的盐;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另外的辅助剂包括结晶抑制剂、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的物质和缓冲液、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、以及液体和固体肥料。
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。在根据本发明的组合物中的油添加剂的量通常是基于有待施用的混合物的从0.01%至10%。例如,可以在喷洒混合物已经制备之后将油添加剂以所希望的浓度添加到喷洒罐中。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、棕榈酸以及油酸的甲基酯(分别为月桂酸甲酯、棕榈酸甲酯和油酸甲酯)。许多油衍生物获知于Compendium of Herbicide Adjuvants[除草剂辅助剂纲要],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%的配制辅助剂,该配制辅助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1至2000l/ha、尤其是从10至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%
撒粉剂:
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。
<u>可湿性粉剂</u> | 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% | - |
将该组合与这些辅助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。
<u>干种子处理用的粉剂</u> | 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% |
将该组合与辅助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。
<u>撒粉剂</u> | 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撒粉剂。此类粉剂还可以用于种子的干拌种。
<u>挤出机颗粒</u> | |
活性成分 | 15% |
木质素磺酸钠 | 2% |
羧甲基纤维素 | 1% |
高岭土 | 82% |
将该组合与这些辅助剂混合并且研磨,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。
<u>包衣的颗粒</u> | |
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。以此方式获得非撒粉的包衣的颗粒。
悬浮液浓缩物
活性成分 | 40% |
丙二醇 | 10% |
壬基酚聚乙二醇醚(15mol的环氧乙烷) | 6% |
木质素磺酸钠 | 10% |
羧甲基纤维素 | 1% |
硅酮油(处于在水中75%的乳液的形式) | 1% |
水 | 32% |
将精细地研磨的组合与辅助剂紧密地混合,给出悬浮液浓缩物,从该悬浮液浓缩物可以通过用水稀释获得任何所希望的稀释度的悬浮液。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷雾、浇灌或浸渍进行保护。
种子处理用的可流动性浓缩物
活性成分 | 40% |
丙二醇 | 5% |
共聚物丁醇PO/EO | 2% |
三苯乙烯酚,具有10-20摩尔EO | 2% |
1,2-苯并异噻唑啉-3-酮(处于在水中20%的溶液形式) | 0.5% |
单偶氮-颜料钙盐 | 5% |
硅酮油(处于在水中75%的乳液的形式) | 0.2% |
水 | 45.3% |
将精细地研磨的组合与辅助剂紧密地混合,给出悬浮液浓缩物,从该悬浮液浓缩物可以通过用水稀释获得任何所希望的稀释度的悬浮液。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷雾、浇灌或浸渍进行保护。
缓释的胶囊悬浮液
将28份的组合与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。向此乳液中添加在5.3份的水中的2.8份的1,6-己二胺混合物。将混合物搅拌直至聚合反应完成。将获得的胶囊悬浮液通过添加0.25份的增稠剂以及3份的分散剂进行稳定。该胶囊悬浮液配制品包含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)、可乳化的颗粒剂(EG)、乳剂、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辅助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。1H NMR测量值在Brucker 400MHz光谱仪上记录,化学位移相对于TMS标准品以ppm给出。光谱在如指定的氘代溶剂中测量。用以下LCMS方法中的任一种来表征这些化合物。对于每种化合物获得的特征LCMS值是保留时间(“Rt”以分钟计记录)和测量的分子离子(M+H)+或(M-H)-。
LCMS和GCMS方法:
方法1:
在来自沃特斯公司(Waters)的质谱仪(SQD,SQDII单四极杆质谱仪)上光谱记录,该质谱仪配备有电喷射源(极性:正离子和负离子,毛细管:3.00kV,锥孔范围:30V,提取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650l/h;质量范围:100Da至900Da)以及来自沃特斯公司的Acquity UPLC:二元泵、经加热的柱室、二极管阵列检测器和ELSD检测器。柱:Waters UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:10%-100%B,在1.2min内;流量(ml/min)0.85
方法2:
在来自沃特斯公司(Waters)的质谱仪(SQD,SQDII单四极杆质谱仪)上光谱记录,该质谱仪配备有电喷射源(极性:正和负离子,毛细管:3.00kV,锥孔范围:30V,提取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650l/h,质量范围:100Da至900Da)和来自沃特斯公司的Acquity UPLC:二元泵、经加热的柱室、二极管阵列检测器和ELSD检测器。柱:Waters UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:10%-100%B,在2.7min内;流量(ml/min)0.85
方法3:
在来自沃特斯公司(Waters)的质谱仪(SQD,SQDII或ZQ单四极杆质谱仪)上光谱记录,该质谱仪配备有电喷射源(极性:正和负离子,毛细管:3.00kV,锥孔范围:30V,提取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650l/h,质量范围:100Da至900Da)和来自沃特斯公司的Acquity UPLC:二元泵、经加热的柱室、二极管阵列检测器和ELSD检测器。柱:Waters UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:0%-10%B,在2.5min内;流量(ml/min)0.85
方法4:
在来自沃特斯公司(Waters)的质谱仪(SQD,SQDII单四极杆质谱仪)上光谱记录,该质谱仪配备有电喷射源(极性:正和负离子,毛细管:3.00kV,锥孔范围:30V,提取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650l/h,质量范围:100Da至900Da)和来自沃特斯公司的Acquity UPLC:二元泵、经加热的柱室、二极管阵列检测器和ELSD检测器。柱:Waters UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:40%-100%B,在1.2min内;流量(ml/min)0.85
方法5:
在来自沃特斯公司的配备有电喷雾源(极性:正和负极性转变,毛细管:3.00kV,锥孔电压:41.00V,源温度:150℃,去溶剂化气体流量:1000L/Hr,去溶剂化温度:500℃,锥孔气体流量:50L/hr,质量范围:110Da-800 Da,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 T3 C18,长度30mm,直径2.1mm,粒度1.8μm。柱烘箱温度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;0.7min-1.3min 0%A,100%B;1.4-1.6min 90%A,10%B。流速0.6mL/min。
实例H1:1-[5-(乙基磺酰亚胺基)-6-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-
6-基]-3-吡啶基]环丙烷甲腈的制备(表P,实例P10)
步骤1:5-(1-氰基-2-乙氧基-2-氧代-乙基)-3-乙基硫烷基-吡啶-2-甲酸甲酯的
制备
将如专利WO 2017/089190中所述而制备的5-溴-3-乙基硫烷基-吡啶-2-甲酸甲酯(32g,115.88mmol)溶于二甲基亚砜(350mL)。然后在室温下连续添加2-氰基乙酸乙酯(18.5mL,173.82mmol)、碳酸钾(40.442g,289.70mmol)和四丁基溴化铵(3.81g,11.588mmol)。将所得悬浮液在90℃下搅拌一夜,然后冷却至室温。添加水和乙酸乙酯,将所得混合物在0℃冷却,缓慢添加盐酸(2M),使反应酸化至pH 4-5。用乙酸乙酯萃取水层三次。将合并的有机层经硫酸钠干燥,过滤并真空浓缩。将所得的粗产物在80℃下在乙醇(250ml)中加热1小时。将所得的溶液冷却至0℃,搅拌1小时并过滤。用冷乙醇洗涤沉淀物,得到5-(1-氰基-2-乙氧基-2-氧代-乙基)-3-乙基硫烷基-吡啶-2-甲酸甲酯。
LCMS(方法1):309(M+H)+;保留时间:0.85min。
1H NMR(400MHz,氯仿-D)δppm 1.33(t,J=7.15Hz,3H)1.45(t,J=7.34Hz,3H)2.98-3.05(m,2H)4.04(s,3H)4.28-4.35(m,2H)4.84(s,1H)7.83(d,J=1.83Hz,1H)8.49(d,J=1.83Hz,1H)。
步骤2:5-(氰基甲基)-3-乙基硫烷基-吡啶-2-甲酸甲酯的制备
将5-(1-氰基-2-乙氧基-2-氧代-乙基)-3-乙基硫烷基-吡啶-2-甲酸甲酯(7.3g,24mmol)溶于二甲基亚砜(70mL)。在室温下向其中依次加入NaCl(14g,240mmol)和水(35mL)。将所得的悬浮液在125℃下搅拌3小时。将反应混合物冷却至室温,用50mL的水和100mL的乙酸乙酯进行稀释。用乙酸乙酯萃取水层三次。将有机层合并,经硫酸钠干燥并真空浓缩。将粗产物在硅胶上纯化,得到5-(氰基甲基)-3-乙基硫烷基-吡啶-2-甲酸甲酯。
LCMS(方法1):237(M+H)+;保留时间:0.72min。
1H NMR(400MHz,氯仿-D)δppm 1.45(t,J=7.52Hz,3H)3.01(q,J=7.34Hz,2H)3.87(s,2H)4.04(s,3H)7.72(d,J=1.83Hz,1H)8.35-8.41(m,1H)。
步骤3:5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-甲酸甲酯的制备
将5-(氰基甲基)-3-乙基硫烷基-吡啶-2-甲酸甲酯(5g,21.16mmol)溶解于乙腈(170mL),并在室温下用碳酸铯(20.7g,63.48mmol)和1,2-二溴乙烷(2.19mL,25.39mmol)处理。将所得的混合物在80℃下搅拌3h 30小时,然后在室温下搅拌过夜。将反应混合物用水和乙酸乙酯稀释。将水性层用乙酸乙酯萃取3次。将合并的有机层用盐水洗涤,经硫酸钠干燥,过滤并真空浓缩,以得到粗产物,将该粗产物通过色谱法纯化,以得到5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-甲酸甲酯。
LCMS(方法1):263(M+H)+;保留时间:0.85min。
1H NMR(400MHz,氯仿-D)δppm 1.45(t,J=7.34Hz,3H)1.54-1.62(m,2H)1.89-1.96(m,2H)3.01(q,J=7.34Hz,2H)4.02(s,3H)7.74(d,J=2.20Hz,1H)8.17(d,J=1.83Hz,1H)。
步骤4:5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-甲酸的制备
将5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-甲酸甲酯(2.63g,10.0mmol)溶解于四氢呋喃(50mL)和水(15mL)。然后添加氢氧化锂(0.375g,15.0mmol)并将反应在室温下搅拌一夜。此时间之后,添加另一部分氢氧化锂(0.160g,7.0mmol)并将反应在室温下再搅拌2小时。将该反应混合物真空浓缩并且将该残余物溶解在二氯甲烷中。添加1M HCl水溶液,将水层(pH 1)用二氯甲烷萃取3次。将合并的有机层经硫酸钠干燥,过滤并真空浓缩,以得到5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-甲酸。
LCMS(方法1):249(M+H)+;保留时间:0.67min。
1H NMR(400MHz,DMSO-d溶剂)δppm 1.26(t,J=7.34Hz,3H)1.70-1.78(m,2H)1.83-1.92(m,2H)3.03(q,J=7.34Hz,2H)7.63(d,J=2.20Hz,1H)8.37(d,J=1.83Hz,1H)13.16-13.40(m,1H)。
步骤5.
5-(1-氰基环丙基)-3-乙基硫烷基-N-[3-(甲基氨基)-6-(三氟甲基)哒
嗪-4-基]吡啶-2-甲酰胺的制备
将5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-甲酸(200mg,0.8055mmol)溶解于二氯甲烷(10mL),并添加N,N-二甲基甲酰胺(10.0μL)。在此悬浮液中,经注射器逐滴添加草酰二氯(0.118mL,1.369mmol)。将所得淡黄色悬浮液在室温下搅拌。1.5h后,将反应混合物真空浓缩,以得到5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-羰基氯。将新鲜的5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-羰基氯(250mg,0.9370mmol)溶解于四氢呋喃(12mL),并逐滴添加N,N-二乙基乙胺(0.27mL,1.933mmol),然后在0℃下添加在四氢呋喃(12mL)中的N3-甲基-6-(三氟甲基)哒嗪-3,4-二胺(651mg,3.222mmol)。将所得混合物在室温下搅拌12小时。然后将反应混合物倒入水(20ml)中,用二氯甲烷(3x20ml)萃取。将合并的萃取物用盐水(30ml)洗涤,用硫酸钠干燥,过滤并真空浓缩。将粗产物通过硅胶色谱法纯化,以得到N-[4-氨基-6-(三氟甲基)哒嗪-3-基]-5-(1-氰基环丙基)-3-乙基硫烷基-N-甲基-吡啶-2-甲酰胺
LCMS(方法2):保留时间:1.04min,423(M+H)+。
步骤6:1-[5-乙基硫烷基-6-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]-
3-吡啶基]环丙烷甲腈的制备
将5-(1-氰基环丙基)-3-乙基硫烷基-N-[3-(甲基氨基)-6-(三氟甲基)哒嗪-4-基]吡啶-2-甲酰胺(240mg,0.5682mmol)和冰乙酸(3mL)混合并在回流下搅拌一夜,并且然后冷却至室温。将乙酸在减压下去除,并且将获得的残余物溶解于乙酸乙酯,并用水性碳酸氢盐溶液碱化。将水层用乙酸乙酯(3x20ml)萃取,并将合并的有机层用硫酸钠干燥,过滤并真空浓缩。将粗产物通过硅胶色谱法纯化,以提供1-[5-乙基硫烷基-6-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]-3-吡啶基]环丙烷甲腈。
LCMS(方法2):保留时间:1.05min,(M+H)+405。
1H NMR(400MHz,氯仿-d)d ppm 1.34-1.46(m,1H)1.38(s,2H)1.62-1.66(m,2H)1.89-2.02(m,2H)2.97-3.10(m,2H)4.26(s,3H)7.76-7.84(m,1H)8.22-8.27(m,1H)8.34-8.41(m,1H)。
步骤7:1-[5-(乙基磺酰亚胺基)-6-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-
6-基]-3-吡啶基]环丙烷甲腈的制备(表P,实例P10)
将1-[5-乙基硫烷基-6-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]-3-吡啶基]环丙烷甲腈(120mg,0.2967mmol)溶解于甲醇(6mL)。然后在室温下添加氨基甲酸铵(46mg,0.5935mmol)和(二乙酰氧基碘)苯(243mg,0.7418mmol)。获得的悬浮液在几分钟后变成溶液,并在室温下搅拌2小时。将反应混合物用水(20ml)淬灭并用二氯甲烷(3x20ml)萃取。将合并的有机层用盐水(30ml)洗涤,用无水硫酸钠干燥,过滤并真空浓缩。将残余物通过硅胶色谱法使用甲醇和二氯甲烷纯化,以得到1-[5-(乙基磺酰亚胺基)-6-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]-3-吡啶基]环丙烷甲腈。
LCMS(方法2):保留时间:0.85min,436.36(M+H)+。
1H NMR(400MHz,氯仿-d)d ppm 1.14-1.32(m,3H)1.25-1.32(m,2H)1.37-1.44(m,3H)1.67-1.77(m,2H)2.03-2.12(m,1H)2.06-2.10(m,1H)2.11(br dd,J=3.48,2.38Hz,1H)2.68-2.84(m,1H)3.71-3.81(m,1H)3.84-3.94(m,1H)4.00-4.14(m,3H)8.18(s,1H)8.36(d,J=2.20Hz,1H)9.04(d,J=2.20Hz,1H)
实例H2.
1-[5-(乙基磺酰亚胺基)-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡
啶-2-基]-3-吡啶基]环丙烷甲腈的制备(实例P6,表P)
步骤1:5-(1-氰基环丙基)-3-乙基硫烷基-N-[2-(甲基氨基)-5-(三氟甲基)-3-吡
啶基]吡啶-2-甲酰胺的制备
将5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-甲酸(2.4g,9.7mmol)溶解于二氯甲烷(100mL)。添加N,N-二甲基甲酰胺(10.0μL),然后通过注射器滴加乙二酰氯(1mL,12mmol)。将所得淡黄色悬浮液在室温下搅拌1小时,然后将溶剂真空浓缩。将所得的固体溶解于四氢呋喃(30ml),并在0℃下添加到N2-甲基-5-(三氟甲基)吡啶-2,3-二胺(1.8g,9.7mmol)和N,N-二乙基乙胺(3.3mL,23mmol)在四氢呋喃(75mL)中的溶液中。将所得混合物在0℃下搅拌30’,然后在室温下搅拌2小时。将反应混合物用NH4Cl饱和溶液处理,并用乙酸乙酯稀释。将水性层用乙酸乙酯萃取3次。将合并的有机层用盐水洗涤,经Na2SO4干燥,过滤并真空浓缩,以得到呈粗品的5-(1-氰基环丙基)-3-乙基硫烷基-N-[2-(甲基氨基)-5-(三氟甲基)-3-吡啶基]吡啶-2-甲酰胺,其不经进一步纯化即用于下一步。
LCMS(方法1):422(M+H)+;保留时间:1.03min。
1H NMR(400MHz,氯仿-d)δppm 1.48(t,J=7.34Hz,3H)1.58-1.63(m,2H)1.93-1.99(m,2H)3.01(q,J=7.34Hz,2H)3.09(d,J=4.77Hz,3H)5.02(br d,J=4.03Hz,1H)7.71(d,J=2.20Hz,1H)7.94(d,J=2.20Hz,1H)8.16(d,J=2.20Hz,1H)8.36(d,J=0.73Hz,1H)9.53-9.60(m,1H)。
步骤2:1-[5-乙基硫烷基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶-2-基]-
3-吡啶基]环丙烷甲腈的制备
将5-(1-氰基环丙基)-3-乙基硫烷基-N-[2-(甲基氨基)-5-(三氟甲基)-3-吡啶基]吡啶-2-甲酰胺(4.2g,10mmol)溶解于乙酸(100mL),并且将所得的溶液在110℃下搅拌18小时。将乙酸在真空中去除,并将粗产物通过硅胶色谱法纯化,以得到1-[5-乙基硫烷基-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶-2-基]-3-吡啶基]环丙烷甲腈,Mp142-144℃。
LCMS(方法1):404(M+H)+;保留时间:1.07min。
1H NMR(400MHz,氯仿-d)δppm 1.40(t,J=7.34Hz,3H)1.59-1.64(m,2H)1.90-1.97(m,2H)3.03(q,J=7.46Hz,2H)4.07(s,3H)7.77(d,J=2.20Hz,1H)8.35(d,J=2.20Hz,1H)8.42(d,J=1.47Hz,1H)8.73-8.78(m,1H)。
步骤3:1-[5-(乙基磺酰亚胺基)-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶-
2-基]-3-吡啶基]环丙烷甲腈的制备(实例P6,表P)
亚砜亚胺的形成类似于实例H1,步骤7。
LCMS(方法1):435(M+H)+;保留时间:0.87min。
1H NMR(400MHz,氯仿)δppm 1.44(t,J=7.34Hz,3H)1.75-1.80(m,2H)2.02-2.08(m,2H)3.94(s,3H)3.94-4.26(m,2H)8.33(d,J=1.47Hz,1H)8.39(d,J=2.20Hz,1H)8.79(d,J=1.47Hz,1H)9.06-9.09(m,1H)。
实例H3:1-[5-(乙基磺酰亚胺基)-6-[5-甲氧基-3-甲基-4-氧代-6-(三氟甲基)咪
唑并[4,5-c]吡啶-2-基]-3-吡啶基]环丙烷甲腈的制备(实例P8,表P)
步骤1:N-[4-溴-6-(二氟甲基)-1-甲氧基-2-氧代-3-吡啶基]-2,2,2-三氟-N-甲
基-乙酰胺的制备
在室温下,向4-溴-1-甲氧基-3-(甲基氨基)-6-(三氟甲基)吡啶-2-酮(5.0g,16.61mmol)在二氯甲烷(100mL)中的溶液中加入三氟乙酸酐(7.09mL,49.82mmol)。将反应混合物在室温下搅拌30分钟,并且然后真空浓缩。加入水(100mL),然后加入饱和碳酸钾水溶液(50mL),并且水层用乙酸乙酯(100mL)萃取。将有机层用盐水(100mL)洗涤,经硫酸钠干燥,过滤,并且真空浓缩。将粗产物在硅胶上纯化,以得到纯的N-[4-溴-6-(二氟甲基)-1-甲氧基-2-氧代-3-吡啶基]-2,2,2-三氟-N-甲基-乙酰胺。
该物质用于下一步骤而无需进一步纯化。
LCMS(方法5):397/399(M+H+),保留时间:0.96min。1H NMR(400MHz,CDCl3)δppm3.27(s,3H),4.16(s,3H),6.84(s,1H)。
步骤2:N-[4-叠氮基-1-甲氧基-2-氧代-6-(三氟甲基)-3-吡啶基]-2,2,2-三氟-
N-甲基-乙酰胺的制备
在室温下向N-[4-溴-1-甲氧基-2-氧代-6-(三氟甲基)-3-吡啶基]-2,2,2-三氟-N-甲基-乙酰胺(11.8g,29.7mmol)在N,N-二甲基甲酰胺(110mL)中的溶液中加入叠氮化钠(2.9g,44.6mmol)。在室温下搅拌反应混合物过夜。分别重复上述反应,然后将合并的反应混合物用冷水(500mL)稀释,并用乙酸乙酯(3x150mL)萃取。将合并的有机层用水(100mL)和盐水洗涤、经硫酸钠干燥,过滤并在低于40℃下真空浓缩,以得到N-[4-叠氮基-1-甲氧基-2-氧代-6-(三氟甲基)-3-吡啶基]-2,2,2-三氟-N-甲基-乙酰胺。该物质用于下一步骤而无需进一步纯化。
LCMS(方法5):360(M+H)+,保留时间:0.90min。1H NMR(400MHz,CDCl3)δppm 3.23(s,3H),4.15(s,3H),6.40(s,1H)。
步骤3:4-叠氮基-1-甲氧基-3-(甲基氨基)-6-(三氟甲基)吡啶-2-酮的制备
向N-[4-叠氮基-1-甲氧基-2-氧代-6-(三氟甲基)-3-吡啶基]-2,2,2-三氟-N-甲基-乙酰胺(4.6g,13.0mmol)在甲醇(100mL)中的溶液中加入碳酸钾(4.7g,33.0mmol)。将反应混合物在室温下搅拌过夜,然后用水(150mL)稀释。将水层用乙酸乙酯(2x75mL)萃取,合并的有机层用盐水(150mL)洗涤,经硫酸钠干燥,过滤并真空浓缩。将粗产物在硅胶(环己烷中40%乙酸乙酯)上纯化,以得到4-叠氮基-1-甲氧基-3-(甲基氨基)-6-(三氟甲基)吡啶-2-酮(2.2g,8.4mmol)。
LCMS(方法E):264(M+H)+,保留时间0.94min。1H NMR(400MHz,CDCl3)δppm 3.18(s,3H),4.11(s,3H),6.46(s,1H)。
步骤4:4-氨基-1-甲氧基-3-(甲基氨基)-6-(三氟甲基)吡啶-2-酮的制备
在室温下,向4-叠氮基-1-甲氧基-3-(甲基氨基)-6-(三氟甲基)吡啶-2-酮(1.7g,6.5mmol)在四氢呋喃(50mL)和(5mL)中溶液中添加三苯基膦(5.1g,19mmol),并且将所得混合物在室温下搅拌2小时。加入2M盐酸水溶液(9mL,18mmol,2mol/L)并在室温下继续搅拌过夜。将反应混合物浓缩并使用饱和碳酸钾水溶液(20mL)淬灭。将水层用乙酸乙酯(2x75 mL)萃取,合并的有机层用盐水(100mL)洗涤,经硫酸钠干燥,过滤并真空浓缩。将残余物在硅胶(环己烷中50%-60%乙酸乙酯)上纯化,以得到4-氨基-1-甲氧基-3-(甲基氨基)-6-(三氟甲基)吡啶-2-酮。
LCMS(方法5):238(M+H)+,保留时间:0.18min。1H NMR(400MHz,d6-DMSO)δppm 2.60(s,3H),3.98(s,3H),5.75(s,2H),6.42(s,1H)。
步骤5:5-(1-氰基环丙基)-3-乙基硫烷基-N-[1-甲氧基-3-(甲基氨基)-2-氧代-
6-(三氟甲基)-4-吡啶基]吡啶-2-甲酰胺和N-[4-氨基-1-甲氧基-2-氧代-6-(三氟甲基)-
3-吡啶基]-5-(1-氰基环丙基)-3-乙基硫烷基-N-甲基-吡啶-2-甲酰胺(异构体混合物)的
制备
向5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-甲酸(400mg,1.61mmol)在二氯甲烷(16mL)中的悬浮液中加入催化量的N,N-二甲基甲酰胺(2滴)并且滴加草酰氯(3.22mmol,0.287mL)。将反应在室温下搅拌6小时并且在真空中除去溶剂,以得到5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-碳酰氯。
将以上5-(1-氰基环丙基)-3-乙基硫烷基-吡啶-2-碳酰氯(428mg,1.60mmol)在干燥四氢呋喃(20mL)中的溶液缓慢加入4-氨基-1-甲氧基-3-(甲基氨基)-6-(三氟甲基)吡啶-2-酮(456.6mg,1.92mmol)和三乙胺(0.678mL,4.81mmol)在四氢呋喃(9.6mL)中的混合物中。将反应混合物在室温下搅拌2小时,然后用水淬灭并用二氯甲烷(100ml)萃取。将合并的有机层用水和盐水洗涤、用无水硫酸钠干燥并真空浓缩,以得到所希望的5-(1-氰基环丙基)-3-乙基硫烷基-N-[1-甲氧基-3-(甲基氨基)-2-氧代-6-(三氟甲基)-4-吡啶基]吡啶-2-甲酰胺和N-[4-氨基-1-甲氧基-2-氧代-6-(三氟甲基)-3-吡啶基]-5-(1-氰基环丙基)-3-乙基硫烷基-N-甲基-吡啶-2-甲酰胺的异构体混合物(750mg,1.60mmol)。该物质用于下一步骤而无需进一步纯化。
LCMS(方法5):468(M+H)+,保留时间:0.86min。
步骤6:1-[5-乙基硫烷基-6-[5-甲氧基-3-甲基-4-氧代-6-(三氟甲基)咪唑并[4,
5-c]吡啶-2-基]-3-吡啶基]环丙烷甲腈的制备
将以上5-(1-氰基环丙基)-3-乙基硫烷基-N-[1-甲氧基-3-(甲基氨基)-2-氧代-6-(三氟甲基)-4-吡啶基]吡啶-2-甲酰胺和N-[4-氨基-1-甲氧基-2-氧代-6-(三氟甲基)-3-吡啶基]-5-(1-氰基环丙基)-3-乙基硫烷基-N-甲基-吡啶-2-甲酰胺的异构体混合物(750mg,1.60mmol)在乙酸(4.8mL)中的溶液加热至100℃持续48小时。在冷却至室温后,将该反应混合物在真空中浓缩。将残余物倒入水中,并用乙酸乙酯(3x100mL)萃取,将合并的有机层用盐水洗涤,经硫酸钠干燥并真空浓缩。通过硅胶色谱法(在环己烷中40%乙酸乙酯)纯化粗产物以得到呈固体的所需产物1-[5-乙基硫烷基-6-[5-甲氧基-3-甲基-4-氧代-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]环丙烷甲腈(350mg)。LCMS(方法E):450(M+H)+,保留时间1.03min。1H NMR(400MHz,CDCl3)δppm 1.37(t,3H),1.59(m,2H),1.93(m,2H),3.01(q,2H),4.20(s,3H),4.21(s,3H),7.25(s,1H),7.76(d,J=2.0Hz,1H),8.32(d,J=2.0Hz,1H)。
步骤7:1-[5-(乙基磺酰亚胺基)-6-[5-甲氧基-3-甲基-4-氧代-6-(三氟甲基)咪 唑并[4,5-c]吡啶-2-基]-3-吡啶基]环丙烷甲腈的制备(实例P8,表P)
亚砜亚胺的形成类似于实例H1,步骤7。
LCMS(方法5):481(M+H)+;保留时间:0.85min。
1H NMR(400MHz,DMSO-d6)δppm 1.14(t,J=7.40Hz,3H)1.83-1.94(m,2H)1.97-2.06(m,2H)3.44-3.66(m,2H)3.86(s,3H)4.12(s,3H)4.56(s,1H)7.41(s,1H)8.38(d,J=2.20Hz,1H)8.90(d,J=2.20Hz,1H)。
实例H4. 1-[3-(乙基磺酰亚胺基)-4-[3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-
c]吡啶-2-基]苯基]环丙烷甲腈的制备(实例P9,表P)
步骤1:N-[4-氨基-6-(三氟甲基硫烷基)-3-吡啶基]-4-溴-2-乙基硫烷基-N-甲
基-苯甲酰胺的制备
在氩气下,将4-溴-2-乙基硫烷基-苯甲酸(如专利WO 2016/120182中所述制备,(1.96g,7.51mmol))悬浮于二氯甲烷(30mL),并添加2滴DMF,逐滴添加草酰二氯(1.24g,0.851mL,9.76mmol),并且观察到气体逸出。将混合物在室温下搅拌4小时,并且然后真空浓缩,以给出作为第一步骤产物的4-溴-2-乙基硫烷基-苯甲酰氯。在氩气下,将新鲜制备的粗4-溴-2-乙基硫烷基-苯甲酰氯(2.07g,7.39mmol)溶解于四氢呋喃(20mL),并添加如专利WO2016/169886中所述而制备的N3-甲基-6-(三氟甲基硫烷基)吡啶-3,4-二胺(1.50g,6.72mmol)。将所得混合物在室温下搅拌一夜,然后在70℃下搅拌8小时。在室温下冷却后添加碳酸氢钠和水。将水性层用乙酸乙酯萃取2次。将合并的有机层经硫酸钠干燥,过滤并真空浓缩,以得到含有N-[4-氨基-6-(三氟甲基硫烷基)-3-吡啶基]-4-溴-2-乙基硫烷基-N-甲基-苯甲酰胺的混合物。
LCMS(方法1):450(M+H)+;保留时间:1.14min。
步骤2:2-(4-溴-2-乙基硫烷基-苯基)-3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-
c]吡啶的制备
将N-[4-氨基-6-(三氟甲基硫烷基)-3-吡啶基]-4-溴-2-乙基硫烷基-N-甲基-苯甲酰胺(3.4g,5.1mmol)溶解于乙酸(51mL)中。将所得溶液在120℃下搅拌一夜,并且然后在室温下冷却。将乙酸在减压下去除,并将粗品通过硅胶色谱法纯化。
将获得的混合物溶解于乙酸乙酯,用碳酸氢盐洗涤,经硫酸钠干燥,过滤并真空浓缩,以得到2-(4-溴-2-乙基硫烷基-苯基)-3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c]吡啶。
LCMS(方法1):450(M+H)+;保留时间:1.14min。
1H NMR(400MHz,氯仿)δppm 1.29(t,J=7.34Hz,3H)2.92(q,J=7.34Hz,2H)3.79(s,3H)7.32(d,J=8.07Hz,1H)7.50(dd,J=8.07,1.83Hz,1H)7.61(d,J=1.83Hz,1H)8.15-8.17(m,1H)8.90(d,J=1.10Hz,1H)。
步骤3:4-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c]吡啶-
2-基]苯基]异噁唑的制备
在氩气下,在微波小瓶中添加DMSO(1.11mL)和水(0.53mL),并将溶液用氩气吹扫5min。然后添加2-(4-溴-2-乙基硫烷基-苯基)-3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c]吡啶(0.2g,0.446mmol)、4-异噁唑硼酸频哪醇酯(0.104g,0.535mmol)和氟化钾(0.077g,1.33mmol)。添加二氯钯;三苯基磷烷(0.0031g,0.0044mmol),并将所得混合物用氩气吹扫5min,在90℃下在微波系统中搅拌40min,在室温下冷却并且然后倒入冰水中。将水层用二氯甲烷萃取3次。然后将乳状水层过滤并将获得的固体溶解于二氯甲烷,并添加至有机层。将合并的有机层经硫酸钠干燥,过滤并真空浓缩。将获得的油状物用水洗涤。将在水中形成的沉淀物过滤,然后再次溶解于二氯甲烷,并将溶剂真空浓缩,以得到4-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c]吡啶-2-基]苯基]异噁唑,将其按原样用于下一步骤。
LCMS(方法1):437(M+H)+;保留时间:0.95min。
步骤4:2-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c]吡啶-
2-基]苯基]乙腈的制备
将4-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c]吡啶-2-基]苯基]异噁唑(236mg,0.3785mmol,70质量%)溶解于甲醇(2mL)和水(1.14mL),并添加氟化钾(1.14mL,1.135mmol)。将该反应混合物在90℃下搅拌3小时。将深红色反应混合物(悬浮液)过滤,用二氯甲烷洗涤并真空浓缩。将粗品通过硅胶色谱法柱纯化,以得到2-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c]吡啶-2-基]苯基]乙腈。
LCMS(方法1):409(M+H)+;保留时间:0.98min。
1H NMR(400MHz,氯仿)δppm 1.29(t,J=7.34Hz,4H)2.93(q,J=7.34Hz,2H)3.80(s,3H)3.89(s,2H)7.34(dd,J=7.89,1.65Hz,1H)7.47-7.48(m,1H)7.48-7.51(m,1H)8.16-8.18(m,1H)8.92(d,J=0.73Hz,1H)。
步骤5:1-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c]吡啶-
2-基]苯基]环丙烷甲腈的制备
将1-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c]吡啶-2-基]苯基]环丙烷甲腈(0.108g,0.2644mmol)溶解于乙腈(1.322mL)。然后添加碳酸二铯(0.2584g,0.7931mmol)和1,2-二溴乙烷(0.1490g,0.0683mL,0.7931mmol)。将反应混合物在微波系统下在100℃搅拌2小时。将反应混合物在真空中浓缩。将残余物溶解于乙酸乙酯并用水和盐水洗涤几次。将有机层经硫酸钠干燥,过滤并真空浓缩。将粗产物经硅胶色谱法纯化,以得到1-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c]吡啶-2-基]苯基]环丙烷甲腈。
LCMS(方法1):435(M+H)+;保留时间:1.04min。
1H NMR(400MHz,氯仿)δppm 1.28(t,J=7.34Hz,4H)1.55(br d,J=2.20Hz,2H)1.86-1.91(m,2H)2.93(q,J=7.58Hz,2H)3.79(s,3H)7.17(dd,J=7.89,2.02Hz,1H)7.44-7.47(m,1H)7.52(d,J=1.83Hz,1H)8.16(d,J=0.73Hz,1H)8.91(d,J=0.73Hz,1H)。
步骤6:1-[3-(乙基磺酰亚胺基)-4-[3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c] 吡啶-2-基]苯基]环丙烷甲腈的合成(实例P9,表P)
如实例H1,步骤7中所述进行亚砜亚胺形成。
LCMS(方法1):466(M+H)+;保留时间:0.86min。
实例H5:1-[3-(乙基磺酰亚胺基)-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-
2-基]苯基]环丙烷甲腈的合成(实例P13,表P)
步骤1:1-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]苯
基]环丙烷甲腈的制备
在氩气气氛、在室温下,向2-(4-溴-2-乙基硫烷基-苯基)-3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶(如专利WO 2016/030229中所述制备)(0.5g,1.201mmol)、Pd2dba3(0.056g,0.060mmol)和BINAP(0.077g,0.120mmol)在四氢呋喃(1.2mL)中的混合物添加环丙烷甲腈(0.090g,1.32mmol)和环丙基甲基醚(1.20mL)。将混合物在-25℃冷却并
在-25℃、在氩气气氛下,逐滴添加双(三甲基甲硅烷基)酰胺锂(1.3mL,1.321mmol)。将混合物在80℃下搅拌2小时。在室温下冷却后,将混合物经用乙酸乙酯洗涤过的硅藻土垫进行过滤。将滤液用水洗涤。将水层分离,并且用乙酸乙酯萃取两次。将有机层合并,经无水硫酸钠干燥,过滤并在真空中浓缩。将粗产物通过硅胶色谱法纯化,以得到1-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]苯基]环丙烷甲腈。
LCMS(方法1):403(M+H)+;保留时间:1.00min。
1H NMR(400MHz,氯仿)δppm 1.27(t,J=7.34Hz,3H)1.52-1.57(m,2H)1.86-1.91(m,2H)2.91(q,J=7.46Hz,2H)3.82(s,3H)7.18(dd,J=8.07,1.83Hz,1H)7.46(d,J=8.07Hz,1H)7.52(d,J=1.83Hz,1H)8.14(d,J=0.73Hz,1H)8.95(s,1H)。
步骤2:1-[3-(乙基磺酰亚胺基)-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-
2-基]苯基]环丙烷甲腈的合成(实例P13,表P)
使用步骤7,实例H1所述的标准程序来制备所希望的产物。
LCMS(方法1):434(M+H)+;保留时间:0.83min。
1H NMR(400MHz,氯仿)δppm 1.28(t,J=7.34Hz,3H)1.63-1.68(m,2H)1.96-2.01(m,2H)3.42-3.62(m,2H)3.75(s,3H)7.56(d,J=8.07Hz,1H)7.89(dd,J=7.89,2.02Hz,1H)8.05(d,J=1.83Hz,1H)8.10(d,J=0.73Hz,1H)8.93-8.96(m,1H)。
实例H5:1-[3-(乙基磺酰亚胺基)-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶-
2-基]苯基]环丙烷甲腈的合成(实例P15,表P)
步骤1:2-乙基硫烷基-4-异噁唑-4-基-苯甲酸甲酯的合成
向氩气下的4-溴-2-乙基硫烷基-苯甲酸甲酯(WO 2016/023954)(250mg,0.91mmol)在二甲亚砜(8mL)中的溶液中加入水(4mL)、4-异噁唑硼酸频哪醇酯(213mg,1.09mmol)和氟化钾(158mg,2.73mmol)。将浓的反应混合物用氩气吹扫5分钟,然后加入双(三苯基膦)二氯化钯(II)(6.4mg,0.009mol)。将小瓶密封,并且将混合物在微波中在90℃下搅拌40分钟。将反应混合物倒入冰水中,并将所得淡黄色悬浮液过滤并用冷水洗涤。将该固体溶解于二氯甲烷中,溶液经硫酸钠干燥并在真空下减少到干燥,以得到呈淡黄色固体的2-乙基硫烷基-4-异噁唑-4-基-苯甲酸甲酯。该物质用于下一步骤而无需进一步纯化。
LCMS(方法1):262(M-H)-,保留时间0.88min。
步骤2:4-(氰基甲基)-2-乙基硫烷基-苯甲酸甲酯的合成
向2-乙基硫烷基-4-异噁唑-4-基-苯甲酸甲酯(760mg,2.89mmol)在甲醇(15mL)中的溶液中加入在水中的1M氟化钾溶液(8.66mL,8.66mmol)。将反应混合物在回流下搅拌3小时。冷却后,将悬浮液过滤,并且将滤液真空浓缩。通过Combiflash在硅胶上纯化残余物,以得到呈胶状物的4-(氰基-甲基)-2-乙基硫烷基-苯甲酸甲酯。
LCMS(方法5):236(M+H)+,保留时间:0.90min。
1H NMR(400MHz,CDCl3)δppm 1.42(t,3H),2.99(q,2H),3.80(s,2H),3.93(s,3H),7.10(dd,1H),7.28(d,1H),7.99(d,1H)。
步骤3:4-(1-氰基环丙基)-2-乙基硫烷基-苯甲酸甲酯的合成
向4-(氰基-甲基)-2-乙基硫烷基-苯甲酸甲酯(300mg,1.275mmol)在乙腈(15mL)中的溶液中加入碳酸铯(1.24g,3.825mmol)和1,2-二溴乙烷(719mg,3.825mmol)。将反应混合物在回流下搅拌90分钟。冷却后,将悬浮液过滤,并且将滤液真空浓缩。通过Combiflash在硅胶上纯化残余物,以得到呈油状物的4-(氰基-甲基)-2-乙基硫烷基-苯甲酸甲酯。
LCMS(方法1):262(M+H)+,保留时间:0.98min。1H NMR(400MHz,CDCl3)δppm 1.43(t,3H),1.48(m,2H),1.82(m,2H),3.01(q,2H),3.92(s,3H),6.88(dd,1H),7.35(d,1H),7.94(d,1H)。
步骤4:4-(1-氰基环丙基)-2-乙基硫烷基-苯甲酸的合成
在0℃-5℃下,向4-(1-氰基环丙基)-2-乙基硫烷基-苯甲酸甲酯(198mg,0.758mmol)在四氢呋喃(9mL)和水(3mL)的混合物中的溶液中加入氢氧化锂(1.5eq.,1.137mmol)并且将反应混合物在室温下搅拌过夜。将溶液真空浓缩,将残余物用叔丁基甲基醚(10mL)稀释,并用1M盐酸水溶液(10mL)酸化。将有机层分离,将水层用用叔丁基甲基醚萃取,将合并的有机层用水和盐水洗涤,经硫酸钠干燥,过滤并真空浓缩,以得到呈固体的4-(1-氰基环丙基)-2-乙基硫烷基-苯甲酸。该物质用于下一步骤而无需进一步纯化。
LCMS(方法5):246(M-H)-,保留时间0.83min。1H NMR(400MHz,CDCl3)δppm 1.44(t,3H),1.51(m,2H),1.85(m,2H),3.03(q,2H),6.90(dd,1H),7.41(d,1H),8.10(d,1H)。
步骤5 1-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶-2-基]苯
基]环丙烷甲腈的制备
将4-(1-氰基环丙基)-2-乙基硫烷基-苯甲酸(1.7g,6.9mmol)溶解于硝基苯(14mL),并添加N2-甲基-5-(三氟甲基)吡啶-2,3-二胺(WO2017/043342)(1.6g,1.2当量),随后在室温下缓慢添加磷酰氯(1.6mL,17mmol)。将所得溶液在120℃下加热7小时,通过TLC和LC-MS监测。将反应物质用30%氢氧化钠溶液淬灭,并添加水(100mL)。将水层用乙酸乙酯(3x100ml)萃取。将合并的有机层经硫酸钠干燥,过滤并在真空中浓缩。将粗产物通过色谱法纯化,以得到1-[3-乙基硫烷基-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶-2-基]苯基]环丙烷甲腈。
LCMS(方法2):403(M+H)+;保留时间:1.18min。
1H NMR(400MHz,氯仿-d)d ppm 1.26(t,J=7.34Hz,3H)1.44-1.61(m,2H)1.80-1.92(m,2H)2.91(q,J=7.42Hz,2H)3.78(s,3H)7.16(dd,J=8.01,1.77Hz,1H)7.44(d,J=7.60Hz,1H)7.50(s,1H)8.33(s,1H)8.72(s,1H)。
步骤6:1-[3-(乙基磺酰亚胺基)-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶-
2-基]苯基]环丙烷甲腈的制备(实例P15,表P)
使用实例H1,步骤7所述的标准程序来制备所希望的产物。
LCMS(方法1):434(M+H)+;保留时间:0.88min。
1H NMR(400MHz,氯仿)δppm 1.28(t,J=7.34Hz,4H)1.63-1.68(m,2H)1.96-2.01(m,2H)3.41-3.62(m,2H)3.75(s,3H)7.56(d,J=8.07Hz,1H)7.89(dd,J=7.89,2.02Hz,1H)8.05(d,J=1.83Hz,1H)8.10(d,J=0.73Hz,1H)8.94-8.97(m,1H)。
实例H6:[5-环丙基-2-[7-(三氟甲基)咪唑并[1,2-b]哒嗪-2-基]-3-吡啶基]-乙
基-亚氨基-氧代-λ6-硫烷的合成(实例P16,表P)。
步骤1.
2-溴-1-(5-溴-3-乙基硫烷基-2-吡啶基)乙酮的制备
将1-(5-溴-3-乙基硫烷基-2-吡啶基)乙酮(在WO 2016/071214中所述进行制备)(1g,3.8439mmol)的样品悬浮于乙腈(3mL)和氯仿(3mL)。添加二溴铜(1.7171g,7.6879mmol),并将反应混合物加热至70℃并搅拌22小时,这个时间之后,LC-MS显示反应完成。将反应混合物通过硅藻土并用二氯甲烷进行过滤。将滤液真空浓缩并将获得的残余物通过硅胶色谱法纯化,以得到2-溴-1-(5-溴-3-乙基硫烷基-2-吡啶基)乙酮。
LCMS(方法1):保留时间:1.10min;339/341(M+H)+。
1H NMR(400MHz,DMSO)δppm 1.28(t,J=7.34Hz,3H)3.06(q,J=7.34Hz,2H)4.93(s,2H)8.11(d,J=1.83Hz,1H)8.58-8.60(m,1H)。
步骤2:2-(5-溴-3-乙基硫烷基-2-吡啶基)-7-(三氟甲基)咪唑并[1,2-b]哒嗪的
制备
在配备回流冷凝器的三颈烧瓶中,将2-溴-1-(5-溴-3-乙基硫烷基-2-吡啶基)乙酮(0.50g,1.5mmol)和5-(三氟甲基)哒嗪-3-胺(CAS[1211591-88-6])(0.27g,1.5mmol)悬浮于乙腈(11mL)中,并添加氧化镁(0.12g,2.9mmol)。将所得混合物加热至90℃并搅拌过夜。过滤反应混合物,并且真空浓缩滤液。将所得固体溶解于乙酸乙酯并用NaHCO3饱和溶液洗涤一次。将有机层用盐水预干燥,经硫酸钠干燥,过滤并真空浓缩。将粗产物通过硅胶色谱法纯化,以得到2-(5-溴-3-乙基硫烷基-2-吡啶基)-7-(三氟甲基)咪唑并[1,2-b]哒嗪。
LCMS(方法1):保留时间:1.15min;403/405(M+H)+。
1H NMR(400MHz,氯仿)δppm 1.44(t,J=7.34Hz,3H)3.04(q,J=7.34Hz,2H)7.82(d,J=1.83Hz,1H)8.33-8.39(m,1H)8.57(dd,J=3.85,2.02Hz,2H)8.81-8.86(m,1H)。
步骤3:2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-7-(三氟甲基)咪唑并[1,2-b]哒
嗪的制备
在100ml-3颈烧瓶中放入甲苯(14mL)和水(0.69mL),并用氩气冲洗5min。在氩气下,添加2-(5-溴-3-乙基硫烷基-2-吡啶基)-7-(三氟甲基)咪唑并[1,2-b]哒嗪(0.30g,0.74mmol)、环丙基硼酸(0.087g,0.97mmol)、磷酸三钾(0.58g,2.6mmol)、三环己基磷烷(0.022g,0.074mmol)和乙酸钯(II)(0.0084g,0.050eq,0.037mmol)。将棕色反应混合物加热达至110℃并搅拌一夜。然后将混合物在室温下冷却并添加水和乙酸乙酯。将所得混合物经硅藻土过滤,并将硅藻土饼通过乙酸乙酯洗涤。将有机层分离,用硫酸钠干燥,过滤并且在真空下浓缩。将粗品通过硅胶色谱法纯化,以得到2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-7-(三氟甲基)咪唑并[1,2-b]哒嗪。
LCMS(方法1):保留时间:1.08min;365(M+H)+。
1H NMR(400MHz,氯仿)δppm 0.81-0.86(m,2H)1.09-1.16(m,2H)1.39(t,J=7.34Hz,3H)1.94-2.03(m,1H)3.00(q,J=7.34Hz,2H)7.36-7.39(m,1H)8.33(d,J=1.83Hz,1H)8.33(s,1H)8.54(d,J=2.20Hz,1H)8.83-8.86(m,1H)。
步骤4:[5-环丙基-2-[7-(三氟甲基)咪唑并[1,2-b]哒嗪-2-基]-3-吡啶基]-乙
基-亚氨基-氧代-λ6-硫烷的制备((实例P16,表P))
将2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-7-(三氟甲基)咪唑并[1,2-b]哒嗪(0.07g,0.1921mmol)悬浮于甲醇(0.5763mL)中,并在室温下添加PhI(OAc)2(0.1894g,0.5763mmol)和氨基甲酸铵(0.03826g,0.4802mmol)。将反应在室温下搅拌并在45min后,用冰水和硫代硫酸钠淬灭。将水层用乙酸乙酯萃取两次。将有机层合并,用盐水洗涤,经无水硫酸钠干燥,过滤并浓缩。将粗产物通过硅胶色谱法纯化,以得到[5-环丙基-2-[7-(三氟甲基)咪唑并[1,2-b]哒嗪-2-基]-3-吡啶基]-乙基-亚氨基-氧代-λ6-硫烷。
LCMS(方法1):保留时间:0.87min;396(M+H)+。
1H NMR(400MHz,氯仿)δppm 0.89-0.95(m,2H)1.18-1.25(m,2H)1.36(t,J=7.52Hz,3H)2.08(tt,J=8.44,5.14Hz,1H)3.21-3.37(br s,1H)3.71-3.98(m,2H)8.19(d,J=2.20Hz,1H)8.26-8.29(m,1H)8.58(d,J=2.20Hz,1H)8.64(d,J=2.20Hz,1H)8.71-8.74(m,1H)。
实例H7:[5-环丙基-2-[6-(三氟甲基)吡唑并[4,3-c]吡啶-2-基]-3-吡啶基]-乙
基-亚氨基-氧代-λ6-硫烷的合成(实例P7,表P)
步骤1:2,5-二溴-3-乙基硫烷基-吡啶的制备
将二乙基二硫化物(7.76g,63.5mmol,2.00当量)和亚硝酸叔丁酯(4.91g,47.6mmol,1.50当量)在DCE(60mL)和DCM(40mL)中的溶液加热至40℃。慢慢地经90min向该混合物缓慢添加2,5-二溴吡啶-3-胺(8.00g,31.7mmol,1.00当量)在二氯乙烷(200mL)中的溶液,并将反应混合物在40℃下再搅拌1h。反应完成后,将反应物质冷却,用水(100mL)稀释,并用二氯甲烷(2x100mL)萃取。将有机层分离,将合并的有机层经硫酸钠干燥,过滤并真空浓缩。将粗产物通过柱色谱法(硅胶,5%-15%乙酸乙酯/环己烷)纯化,以得到2,5-二溴-3-乙基硫烷基-吡啶。
LCMS(方法4):296(M+H)+,保留时间:1.16min。
1H NMR(400MHz,CDCl3)δ/ppm:1.32(t,3H),2.98(m,2H),7.52(s,1H)8.19(s,1H)。
步骤2:(5-溴-3-乙基硫烷基-2-吡啶基)肼的制备
向2,5-二溴-3-乙基硫烷基-吡啶(1g,3.3669mmol)在1,4-二噁烷(10.34g)中的溶液中添加肼一水合物(1.0113g,20.201mmol),并将所得混合物在120℃下搅拌10小时。反应完成后,将混合物用水(30ml)稀释并用乙酸乙酯萃取。将合并的有机层用水(20ml)洗涤,用硫酸钠干燥,过滤并真空浓缩,以得到(5-溴-3-乙基硫烷基-2-吡啶基)肼。
LCMS:250(M+H)+,保留时间0.6min。
1H NMR(400MHz,氯仿-d)d ppm 1.26(t,3H)2.81(q,2H)3.10(br 2H)6.67(br s,1H)7.65(d,1H)8.15(d,1H)。
步骤3:4-[2-(5-溴-3-乙基硫烷基-2-吡啶基)肼基]-6-(三氟甲基)吡啶-3-甲酸
的制备
将4-氯-6-(三氟甲基)吡啶-3-甲酸(CAS[1060810-66-3])(20g,88.672mmol)、(5-溴-3-乙基硫烷基-2-吡啶基)肼(33.005g,133.01mmol)和戊-1-醇(120mL)混合,并将混合物在110℃下搅拌15小时。反应完成后,将混合物真空浓缩以去除所有戊醇。将获得的残余物与甲苯共蒸发。将粗产物用水(100ml)、盐水(100ml)稀释,并用乙酸乙酯(3x200ml)萃取。将合并的有机层经硫酸钠干燥,过滤并在真空中浓缩。将获得的固体用环己烷研磨,以得到4-[2-(5-溴-3-乙基硫烷基-2-吡啶基)肼基]-6-(三氟甲基)吡啶-3-甲酸。
LCMS(方法5):保留时间1.50min,439(M+2)+。
1H NMR(400MHz,DMSO-d6)d ppm 1.26(t,3H)3.05(q,2H)7.16(s,1H)7.89(d,1H)8.11(d,1H)8.77(s,1H)8.88(s,1H)9.83(s,1H)13.38-14.36(m,1H)。
步骤4:2-(5-溴-3-乙基硫烷基-2-吡啶基)-3-氯-6-(三氟甲基)吡唑并[4,3-c]吡
啶的制备
将4-[2-(5-溴-3-乙基硫烷基-2-吡啶基)肼基]-6-(三氟甲基)吡啶-3-甲酸(22.87mmol,10g)溶解于磷酰氯(100mL),并将所得混合物在110℃下加热。将获得的澄清溶液在110℃下回流50min。反应完成后,将混合物浓缩(在减压下蒸馏掉磷酰氯),并将反应物用二氯甲烷(110ml)稀释,倒入冰水(200mL)中。将水层用二氯甲烷(2x100ml)萃取。将合并的有机层用水(200ml)洗涤,经硫酸钠干燥,过滤,并真空浓缩。将粗产物通过硅胶色谱法纯化,以得到2-(5-溴-3-乙基硫烷基-2-吡啶基)-3-氯-6-(三氟甲基)吡唑并[4,3-c]吡啶。
LCMS:437(M+H)+,保留时间1.21min。
1H NMR(400MHz,氯仿-d)d ppm 1.34(m,3H)2.85(m,2H)7.92(S,2H)8.02(m,1H)8.60(m,1H)9.32(m,1H)。
步骤5:2-(5-溴-3-乙基硫烷基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶的
制备
将2-(5-溴-3-乙基硫烷基-2-吡啶基)-3-氯-6-(三氟甲基)吡唑并[4,3-c]吡啶(0.2mmol,0.1g)溶解于乙酸(2mL),并将锌(0.5mmol,0.03g)缓慢添加至混合物。将反应物质在55℃下搅拌40min。通过LCMS和TLC监测该反应。完成后,将反应混合物倒入水(30ml)中,并且将所得溶液用乙酸乙酯(20mlx3)萃取。将合并的有机层用水性饱和氯化钠溶液(30ml)洗涤,经无水硫酸钠干燥,过滤并真空浓缩。将残余物经受硅胶柱色谱法,以得到2-(5-溴-3-乙基硫烷基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶。
H NMR(400MHz,氯仿-d)d ppm 1.29(m,4H)2.95(m,2H)7.85(m,1H)8.35(m,1H)8.38(d,1H)8.95(m,1H)9.44(m,1H)。
LCMS:保留时间1.6min,403(M+H)+。
步骤6:2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡
啶的制备
在微波小瓶中,在甲苯(2mL)和水(1mL)中添加2-(5-溴-3-乙基硫烷基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶(0.1g,0.2mmol)、环丙基硼酸(0.03g,0.3mmol)、磷酸三钾(0.2g,0.9mmol)、三环己基磷烷(0.007g,0.02mmol)。将反应物质用氮气吹扫30min。然后向其中添加乙酸钯(II)(0.003g,0.01mmol),并将反应混合物在150℃在微波下搅拌4小时。然后在室温下将反应混合物用乙酸乙酯(20mL)稀释,并用水(20mL)洗涤。将有机层用水(20ml)洗涤,经硫酸钠干燥有机层,过滤并真空浓缩。将化合物通过硅胶色谱法分离,以得到2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-6-(三氟甲基)吡唑并[4,3-c]吡啶。
LCMS:365(M+H)+,保留时间1.12min。
1H NMR(400MHz,氯仿-d)d ppm 0.86(m,2H)1.13(br,2H)1.23(m,4H)2.90(q,2H)7.47(d,1H)8.13(m,2H)8.94(s,1H)9.40(m,1H)。
步骤7:[5-环丙基-2-[6-(三氟甲基)吡唑并[4,3-c]吡啶-2-基]-3-吡啶基]-乙
基-亚氨基-氧代-λ6-硫烷的合成(实例P7,表P)
使用实例H1,步骤7所述的标准方法来制备所希望的产物。
LCMS(方法5):保留时间0.94min,396(M+H)+。
1H NMR(400MHz,氯仿-d)d ppm 1.25(m,4H)1.44(m,3H)2.16(m,1H)3.87(m,2H)8.06(s,1H)8.29(d,1H)8.56(d,1H)8.87(d,1H)9.40(s,1H)。
实例H8:[5-环丙基-2-[5-(三氟甲基硫烷基)-1,3-苯并噁唑-2-基]-3-吡啶基]-
乙基-亚氨基-氧代-λ6-硫烷的合成(实例P18,表P)
使用实例H1,步骤7所述的标准方法从2-(5-环丙基-3-乙基硫烷基-2-吡啶基)-5-(三氟甲基硫烷基)-1,3-苯并噁唑(从WO 19/009307得知)开始来制备所希望的产物。
LCMS(方法5):428(M+H)+,保留时间:1.03min。
可以与上述方法类似地制备本发明的另外的化合物。表P中列出了为进一步说明本发明而制备的化合物。
通过添加其他杀昆虫、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出人意料的优点,这些优点还可以在更宽的意义上描述为协同活性。例如,植物的更好的耐受性、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,在研磨或者混合期间,在它们的储存期间或它们的使用期间)的更好的行为。
在这里,适当添加的活性成分是例如以下类别的活性成分的代表:有机磷化合物、硝基苯酚衍生物、硫脲、保幼激素、甲脒、二苯甲酮衍生物、脲类、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、大环内酯类、新烟碱以及苏芸金芽孢杆菌制剂。
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”意指“选自下组的一种化合物,所述组由描述于表Y-1至Y-8、X-1至X-8、U-1至U-2和V-1至V-6和表P中的本发明的化合物组成”):
辅助剂,其选自由以下组成的物质组:石油(别名)(628)+TX;
杀螨剂,其选自由以下组成的物质组: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酯(IUPAC/化学文摘名)(1059)+TX、2-氟-N-甲基-N-1-萘乙酰胺(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、赛硫磷(870)+TX、磺胺螨酯[CCN]+TX、氨基硫代盐(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、益棉磷(44)+TX、保棉磷(azinphos-methyl)(45)+TX、偶氮苯(IUPAC名称)(888)+TX、三唑锡(azacyclotin)(46)+TX、偶氮磷(azothoate)(889)+TX、苯菌灵(62)+TX、苯诺沙磷(benoxafos)(别名)[CCN]+TX、苯螨特(benzoximate)(71)+TX、苯甲酸苄酯(IUPAC名称)[CCN]+TX、联苯肼酯(74)+TX、氟氯菊酯(76)+TX、乐杀螨(907)+TX、溴灭菊酯(别名)+TX、溴烯杀(bromocyclene)(918)+TX、溴硫磷(920)+TX、乙基溴硫磷(921)+TX、溴螨酯(bromopropylate)(94)+TX、噻嗪酮(99)+TX、丁酮威(103)+TX、丁酮砜威(104)+TX、丁基哒螨灵(butylpyridaben)(别名)+TX、石硫合剂(calcium polysulfide)(IUPAC名称)(111)+TX、毒杀芬(campheechlor)(941)+TX、氯灭杀威(carbanolate)(943)+TX、甲萘威(115)+TX、克百威(carbofuran)(118)+TX、卡波硫磷(947)+TX、CGA 50'439(研究代码)(125)+TX、灭螨猛(chinomethionat)(126)+TX、杀螨醚(chlorbenside)(959)+TX、杀虫脒(964)+TX、杀虫脒盐酸盐(964)+TX、溴虫腈(130)+TX、敌螨(968)+TX、杀螨酯(chlorfenson)(970)+TX、敌螨特(chlorfensulfide)(971)+TX、氯芬磷(131)+TX、乙酯杀螨醇(chlorobenzilate)(975)+TX、伊托明(chloromebuform)(977)+TX、灭虫脲(chloromethiuron)(978)+TX、丙酯杀螨醇(chloropropylate)(983)+TX、毒死蜱(145)+TX、甲基毒死蜱(146)+TX、虫螨磷(chlorthiophos)(994)+TX、瓜菊酯(cinerin)I(696)+TX、瓜菊酯II(696)+TX、瓜叶菊素(cinerins)(696)+TX、四螨嗪(158)+TX、氯氰碘柳胺(别名)[CCN]+TX、库马磷(174)+TX、克罗米通(别名)[CCN]+TX、巴毒磷(crotoxyphos)(1010)+TX、硫杂灵(1013)+TX、果虫磷(cyanthoate)(1020)+TX、丁氟螨酯(CAS登记号:400882-07-7)+TX、三氯氟氰菊酯(196)+TX、三环锡(199)+TX、氯氰菊酯(201)+TX、DCPM(1032)+TX、DDT(219)+TX、田乐磷(demephion)(1037)+TX、田乐磷-O(1037)+TX、田乐磷-S(1037)+TX、内吸磷(demeton)(1038)+TX、甲基内吸磷(224)+TX、内吸磷-O(1038)+TX、甲基内吸磷-O(224)+TX、内吸磷-S(1038)+TX、甲基内吸磷-S(224)+TX、内吸磷-S-甲基磺隆(demeton-S-methylsulfon)(1039)+TX、杀螨隆(226)+TX、dimpropyridaz+TX、氯亚胺硫磷(dialifos)(1042)+TX、二嗪磷(227)+TX、苯氟磺胺(230)+TX、敌敌畏(236)+TX、甲氟磷(dicliphos)(别名)+TX、开乐散(242)+TX、百治磷(243)+TX、遍地克(1071)+TX、甲氟磷(dimefox)(1081)+TX、乐果(262)+TX、二甲杀螨霉素(dinacti)(别名)(653)+TX、消螨酚(dinex)(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、消螨通(dinobuton)(269)+TX、敌螨普(dinocap)(270)+TX、敌螨普-4[CCN]+TX、敌螨普-6[CCN]+TX、二硝酯(1090)+TX、硝戊酯(dinopenton)(1092)+TX、硝辛酯(dinosulfon)(1097)+TX、硝丁酯(dinoterbon)(1098)+TX、敌恶磷(1102)+TX、二苯砜(IUPAC名称)(1103)+TX、双硫仑(别名)[CCN]+TX、乙拌磷(278)+TX、DNOC(282)+TX、苯氧炔螨(dofenapyn)(1113)+TX、多拉克汀(别名)[CCN]+TX、硫丹(294)+TX、因毒磷(endothion)(1121)+TX、EPN(297)+TX、依立诺克丁(别名)[CCN]+TX、乙硫磷(309)+TX、益硫磷(ethoate-methyl)(1134)+TX、乙螨唑(etoxazole)(320)+TX、乙嘧硫磷(etrimfos)(1142)+TX、抗螨唑(fenazaflor)(1147)+TX、喹螨醚(328)+TX、苯丁锡(fenbutatin oxide)(330)+TX、苯硫威(fenothiocarb)(337)+TX、甲氰菊酯(342)+TX、吡螨胺(fenpyrad)(别名)+TX、唑螨酯(fenpyroximate)(345)+TX、芬螨酯(fenson)(1157)+TX、氟硝二苯胺(fentrifanil)(1161)+TX、氰戊菊酯(349)+TX、氟虫腈(354)+TX、嘧螨酯(fluacrypyrim)(360)+TX、啶蜱脲(1166)+TX、氟螨噻(flubenzimine)(1167)+TX、氟螨脲(366)+TX、氟氰戊菊酯(flucythrinate)(367)+TX、联氟螨(fluenetil)(1169)+TX、氟虫脲(370)+TX、氟氯苯菊酯(flumethrin)(372)+TX、氟杀螨(fluorbenside)(1174)+TX、氟胺氰菊酯(fluvalinate)(1184)+TX、FMC 1137(研究代码)(1185)+TX、伐虫脒(405)+TX、伐虫脒盐酸盐(405)+TX、安硫磷(formothion)(1192)+TX、胺甲威(formparanate)(1193)+TX、γ-HCH(430)+TX、果绿定(glyodin)(1205)+TX、苄螨醚(halfenprox)(424)+TX、庚烯醚(heptenophos)(432)+TX、十六烷基环丙烷羧酸酯(IUPAC/化学文摘名)(1216)+TX、噻螨酮(441)+TX、碘甲烷(IUPAC名称)(542)+TX、水胺硫磷(isocarbophos)(别名)(473)+TX、异丙基O-(甲氧基氨基硫代磷酰基)水杨酸酯(IUPAC名称)(473)+TX、伊维菌素(别名)[CCN]+TX、茉莉菊酯(jasmolin)I(696)+TX、茉莉菊酯II(696)+TX、碘硫磷(jodfenphos)(1248)+TX、林旦(430)+TX、氯芬奴隆(490)+TX、马拉硫磷(492)+TX、丙螨氰(malonoben)(1254)+TX、灭蚜磷(mecarbam)(502)+TX、二噻磷(mephosfolan)(1261)+TX、甲硫芬(别名)[CCN]+TX、虫螨畏(methacrifos)(1266)+TX、甲胺磷(527)+TX、杀扑磷(529)+TX、灭虫威(530)+TX、灭多虫(531)+TX、溴甲烷(537)+TX、速灭威(metolcarb)(550)+TX、速灭磷(556)+TX、自克威(mexacarbate)(1290)+TX、灭螨菌素(557)+TX、米尔贝肟(milbemycin oxime)(别名)[CCN]+TX、丙胺氟(mipafox)(1293)+TX、久效磷(561)+TX、茂果(morphothion)(1300)+TX、莫昔克丁(别名)[CCN]+TX、二溴磷(naled)(567)+TX、NC-184(化合物代码)+TX、NC-512(化合物代码)+TX、氟蚁灵(nifluridide)(1309)+TX、尼可霉素(别名)[CCN]+TX、戊氰威(nitrilacarb)(1313)+TX、戊氰威(nitrilacarb)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、氧乐果(omethoate)(594)+TX、杀线威(602)+TX、亚异砜磷(oxydeprofos)(1324)+TX、砜拌磷(oxydisulfoton)(1325)+TX、pp’-DDT(219)+TX、对硫磷(615)+TX、苄氯菊酯(626)+TX、石油油料(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(phosfolan)(1338)+TX、亚胺硫磷(638)+TX、磷胺(639)+TX、辛硫磷(642)+TX、甲基嘧啶磷(652)+TX、氯化松节油(polychloroterpenes)(传统名称)(1347)+TX、杀螨素(polynactins)(别名)(653)+TX、丙氯诺(1350)+TX、丙溴磷(662)+TX、蜱虱威(promacyl)(1354)+TX、克螨特(671)+TX、胺丙畏(propetamphos)(673)+TX、残杀威(678)+TX、乙噻唑磷(prothidathion)(1360)+TX、发硫磷(prothoate)(1362)+TX、除虫菊酯I(696)+TX、除虫菊酯II(696)+TX、除虫菊酯(pyrethrins)(696)+TX、哒螨灵(699)+TX、哒嗪硫磷(pyridaphenthion)(701)+TX、嘧螨醚(pyrimidifen)(706)+TX、嘧硫磷(1370)+TX、喹硫磷(quinalphos)(711)+TX、喹硫磷(quintiofos)(1381)+TX、R-1492(研究代码)(1382)+TX、RA-17(研究代码)(1383)+TX、鱼藤酮(722)+TX、八甲磷(schradan)(1389)+TX、克线丹(sebufos)(别名)+TX、司拉克丁(selamectin)(别名)[CCN]+TX、SI-0009(化合物代码)+TX、苏硫磷(sophamide)(1402)+TX、螺螨酯(738)+TX、螺甲螨酯(739)+TX、SSI-121(研究代码)(1404)+TX、舒非仑(别名)[CCN]+TX、氟虫胺(sulfluramid)(750)+TX、硫特普(sulfotep)(753)+TX、硫(754)+TX、SZI-121(研究代码)(757)+TX、τ-氟胺氰菊酯(398)+TX、吡螨胺(763)+TX、TEPP(1417)+TX、叔丁威(terbam)(别名)+TX、司替罗磷(777)+TX、四氯杀螨砜(tetradifon)(786)+TX、杀螨素(tetranactin)(别名)(653)+TX、杀螨好(tetrasul)(1425)+TX、thiafenox(别名)+TX、抗虫威(thiocarboxime)(1431)+TX、久效威(thiofanox)(800)+TX、甲基乙拌磷(thiometon)(801)+TX、克杀螨(1436)+TX、苏力菌素(thuringiensin)(别名)[CCN]+TX、威菌磷(triamiphos)(1441)+TX、苯螨噻(triarathene)(1443)+TX、三唑磷(820)+TX、灭蚜唑(triazuron)(别名)+TX、敌百虫(824)+TX、三氯丙氧磷(trifenofos)(1455)+TX、三活菌素(trinactin)(别名)(653)+TX、蚜灭多(847)+TX、甲烯氟虫腈(vaniliprole)[CCN]和YI-5302(化合物代码)+TX,
杀藻剂,其选自由以下组成的物质组:百杀辛(bethoxazin)[CCN]+TX、二辛酸铜(IUPAC名称)(170)+TX、硫酸铜(172)+TX、cybutryne[CCN]+TX、二氯萘醌(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、三苯基乙酸锡(IUPAC名称)(347)和三苯基氢氧化锡(IUPAC名称)(347)+TX,
驱蠕虫剂,其选自由以下组成的物质组:阿维菌素(1)+TX、育畜磷(1011)+TX、多拉克汀(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、哌嗪[CCN]+TX、司拉克丁(selamectin)(别名)[CCN]+TX、多杀菌素(737)和托布津(thiophanate)(1435)+TX,
杀鸟剂,其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,
杀细菌剂,其选自由以下组成的物质组: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、双吡硫翁(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)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、噻菌灵(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,
生物试剂,其选自由以下组成的物质组:棉褐带卷蛾GV(别名)(12)+TX、放射形土壤杆菌(别名)(13)+TX、钝绥螨属物种(Amblyseius spp.)(别名)(19)+TX、芹菜夜蛾NPV(别名)(28)+TX、原樱翅缨小蜂(Anagrus atomus)(别名)(29)+TX、短距蚜小蜂(Aphelinusabdominalis)(别名)(33)+TX、棉蚜寄生蜂(Aphidius colemani)(别名)(34)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)(别名)(35)+TX、苜蓿银纹夜蛾NPV(别名)(38)+TX、坚强芽孢杆菌(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(Beauveriabrongniartii)(别名)(54)+TX、普通草蛉(Chrysoperla carnea)(别名)(151)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(别名)(178)+TX、苹果蠹蛾GV(别名)(191)+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)(别名)(212)+TX、豌豆潜叶蝇姬小蜂(Diglyphusisaea)(别名)(254)+TX、丽蚜小蜂(Encarsia formosa)(学名)(293)+TX、桨角蚜小蜂(Eretmocerus eremicus)(别名)(300)+TX、谷实夜蛾NPV(别名)(431)+TX、嗜菌异小杆线虫(Heterorhabditis bacteriophora)和大异小杆线虫(H.megidis)(别名)(433)+TX、斑长足瓢虫(Hippodamia convergens)(别名)(442)+TX、橘粉介壳虫寄生蜂(Leptomastixdactylopii)(别名)(488)+TX、盲蝽(Macrolophus caliginosus)(别名)(491)+TX、甘蓝夜蛾NPV(别名)(494)+TX、黄阔柄跳小蜂(Metaphycus helvolus)(别名)(522)+TX、黄绿绿僵菌(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、欧洲新松叶蜂(Neodiprionsertifer)NPV和红头新松叶蜂(N.lecontei)NPV(别名)(575)+TX、小花蝽属物种(别名)(596)+TX、玫烟色拟青霉(Paecilomyces fumosoroseus)(别名)(613)+TX、智利小植绥螨(Phytoseiulus persimilis)(别名)(644)+TX、甜菜夜蛾核多角体病毒(Spodopteraexigua multicapsid nuclear polyhedrosis virus)(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(别名)(742)+TX、格氏线虫(Steinernema glaseri)(别名)(742)+TX、锐比斯氏线虫(Steinernema riobrave)(别名)(742)+TX、Steinernemariobravis(别名)(742)+TX、蝼蛄斯氏线虫(Steinernema scapterisci)(别名)(742)+TX、斯氏线虫属物种(Steinernema spp.)(别名)(742)+TX、赤眼蜂属物种(别名)(826)+TX、西方盲走螨(Typhlodromus occidentalis)(别名)(844)和蜡蚧轮枝菌(Verticilliumlecanii)(别名)(848)+TX,
土壤消毒剂,其选自由以下组成的物质组:碘甲烷(IUPAC名称)(542)和溴甲烷(537)+TX,
化学不育剂,其选自由以下组成的物质组: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、甲基唑磷嗪(methylapholate)[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、硫涕巴(别名)[CCN]+TX、曲他胺(别名)[CCN]和尿烷亚胺(别名)[CCN]+TX,
昆虫信息素,其选自由以下组成的物质组:(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-甲基十八碳-1-烯(IUPAC名称)(545)+TX、4-甲基壬-5-醇与4-甲基壬-5-酮(IUPAC名称)(544)+TX、α-多纹素(alpha-multistriatin)(别名)[CCN]+TX、西部松小蠹集合信息素(brevicomin)(别名)[CCN]+TX、十二碳二烯醇(codlelure)(别名)[CCN]+TX、可得蒙(codlemone)(别名)(167)+TX、诱蝇酮(cuelure)(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、dominicalure(别名)[CCN]+TX、4-甲基辛酸乙酯(IUPAC名称)(317)+TX、丁香酚(别名)[CCN]+TX、南部松小蠹集合信息素(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(hexalure)[CCN]+TX、齿小蠹二烯醇(ipsdienol)(别名)[CCN]+TX、小蠢烯醇(ipsenol)(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、litlure(别名)[CCN]+TX、粉纹夜蛾性诱剂(looplure)(别名)[CCN]+TX、诱杀酯(medlure)[CCN]+TX、megatomoic acid(别名)[CCN]+TX、诱虫醚(methyl eugenol)(别名)(540)+TX、诱虫烯(muscalure)(563)+TX、十八碳-2,13-二烯-1-基乙酸酯(IUPAC名称)(588)+TX、十八碳-3,13-二烯-1-基乙酸酯(IUPAC名称)(589)+TX、贺康彼(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(siglure)[CCN]+TX、sordidin(别名)(736)+TX、食菌甲诱醇(sulcatol)(别名)[CCN]+TX、十四碳-11-烯-1-基乙酸酯(IUPAC名称)(785)+TX、地中海实蝇引诱剂(839)+TX、地中海实蝇引诱剂A(别名)(839)+TX、地中海实蝇引诱剂B1(别名)(839)+TX、地中海实蝇引诱剂B2(别名)(839)+TX、地中海实蝇引诱剂C(别名)(839)和trunc-call(别名)[CCN]+TX,
昆虫驱避剂,其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、驱蚊灵(dimethyl carbate)[CCN]+TX、邻苯二甲酸二甲酯[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、草氨酸盐(oxamate)[CCN]和派卡瑞丁[CCN]+TX,
杀昆虫剂,其选自由以下组成的物质组:1-二氯-1-硝基乙烷(IUPAC/化学文摘名称)(1058)+TX、1,1-二氯-2,2-二(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、带有1,3-二氯丙烯的1,2-二氯丙烷(IUPAC名称)(1063)+TX、1-溴-2-氯乙烷(IUPAC/化学文摘名称)(916)+TX、乙酸2,2,2-三氯-1-(3,4-二氯苯基)乙基酯(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酯(IUPAC名称)(1066)+TX、二甲基氨基甲酸2-(1,3-二硫杂环戊烷-2-基)苯基酯(IUPAC/化学文摘名称)(1109)+TX、硫氰酸2-(2-丁氧基乙氧基)乙基酯(IUPAC/化学文摘名称)(935)+TX、甲基氨基甲酸2-(4,5-二甲基-1,3-二氧环戊烷-2-基)苯基酯(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-咪唑啉酮(IUPAC名称)(1225)+TX、2-异戊酰基茚满-1,3-二酮(IUPAC名称)(1246)+TX、甲基氨基甲酸2-甲基(丙-2-炔基)氨基苯基酯(IUPAC名称)(1284)+TX、月桂酸2-硫氰基乙基酯(IUPAC名称)(1433)+TX、3-溴-1-氯丙-1-烯(IUPAC名称)(917)+TX、二甲基氨基甲酸3-甲基-1-苯基吡唑-5-基酯(IUPAC名称)(1283)+TX、甲基氨基甲酸4-甲基(丙-2-炔基)氨基-3,5-二甲苯基酯(IUPAC名称)(1285)+TX、二甲基氨基甲酸5,5-二甲基-3-氧代环己-1-烯基酯(IUPAC名称)(1085)+TX、阿维菌素(1)+TX、乙酰甲胺磷(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、氯甲桥萘(864)+TX、烯丙菊酯(17)+TX、阿洛氨菌素(别名)[CCN]+TX、除害威(866)+TX、α-氯氰菊酯(202)+TX、α-蜕皮激素(别名)[CCN]+TX、磷化铝(640)+TX、赛硫磷(870)+TX、硫代酰胺(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、甲基吡啶磷(42)+TX、谷硫磷-乙基(44)+TX、谷硫磷-甲基(45)+TX、偶氮磷(889)+TX、苏云金芽孢杆菌δ内毒素类(别名)(52)+TX、六氟硅酸钡(别名)[CCN]+TX、多硫化钡(IUPAC/化学文摘名称)(892)+TX、熏菊酯[CCN]+TX、Bayer 22/190(研究代码)(893)+TX、Bayer22408(研究代码)(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、生物烯丙菊酯(78)+TX、生物烯丙菊酯S-环戊烯基异构体(别名)(79)+TX、戊环苄呋菊酯(bioethanomethrin)[CCN]+TX、生物氯菊酯(908)+TX、除虫菊酯(80)+TX、二(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、溴杀烯(918)+TX、溴-DDT(别名)[CCN]+TX、溴硫磷(920)+TX、溴硫磷-乙基(921)+TX、合杀威(924)+TX、噻嗪酮(99)+TX、畜虫威(926)+TX、脱甲基丁嘧啶磷(butathiofos)(927)+TX、丁酮威(103)+TX、丁酯膦(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、甲萘威(115)+TX、克百威(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、藜芦碱(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、氟啶脲(132)+TX、氯甲磷(136)+TX、氯仿[CCN]+TX、氯化苦(141)+TX、氯腈肟磷(989)+TX、灭虫吡啶(chlorprazophos)(990)+TX、毒死蜱(145)+TX、毒死蜱-甲基(146)+TX、虫螨磷(994)+TX、环虫酰肼(150)+TX、灰菊素I(696)+TX、灰菊素II(696)+TX、灰菊素类(696)+TX、顺式苄呋菊酯(cis-resmethrin)(替代名称)+TX、顺式苄呋菊酯(cismethrin)(80)+TX、功夫菊酯(替代名称)+TX、除线威(999)+TX、氯氰碘柳胺(替代名称)[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(替代名称)[CCN]+TX、巴毒磷(1010)+TX、克芦磷酯(1011)+TX、冰晶石(替代名称)(177)+TX、CS708(研究代码)(1012)+TX、苯腈膦(1019)+TX、杀螟睛(184)+TX、果虫磷(1020)+TX、环虫菊酯[CCN]+TX、乙氰菊酯(188)+TX、氟氯氰菊酯(193)+TX、三氯氟氰菊酯(196)+TX、氯氰菊酯(201)+TX、苯氰菊酯(206)+TX、环丙马秦(209)+TX、畜蜱磷(替代名称)[CCN]+TX、d-柠檬烯(替代名称)[CCN]+TX、d-四甲菊酯(替代名称)(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、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、二胺磷(1044)+TX、二嗪磷(227)+TX、异氯磷(1050)+TX、除线磷(1051)+TX、敌敌畏(236)+TX、迪克力弗斯(dicliphos)(替代名称)+TX、迪克莱赛尔(dicresyl)(替代名称)[CCN]+TX、百治磷(243)+TX、地昔尼尔(244)+TX、狄氏刑(1070)+TX、二乙基5-甲基吡唑-3-基磷酸酯(IUPAC名称)(1076)+TX、除虫脲(250)+TX、二羟丙茶碱(dilor)(替代名称)[CCN]+TX、四氟甲醚菊酯[CCN]+TX、甲氟磷(1081)+TX、地麦威(1085)+TX、乐果(262)+TX、苄菊酯(1083)+TX、甲基毒虫畏(265)+TX、敌蝇威(1086)+TX、消螨酚(1089)+TX、消螨酚(dinex-diclexine)(1089)+TX、丙硝酚(1093)+TX、戊硝酚(1094)+TX、达诺杀(1095)+TX、呋虫胺(271)+TX、苯虫醚(1099)+TX、蔬果磷(1100)+TX、二氧威(1101)+TX、敌恶磷(1102)+TX、乙拌磷(278)+TX、苯噻乙双硫磷(dithicrofos)(1108)+TX、DNOC(282)+TX、多拉克汀(替代名称)[CCN]+TX、DSP(1115)+TX、蜕皮激素(替代名称)[CCN]+TX、EI1642(研究代码)(1118)+TX、甲氧基阿维菌素(291)+TX、甲氧基阿维菌素苯甲酸盐(291)+TX、EMPC(1120)+TX、烯炔菊酯(292)+TX、硫丹(294)+TX、因毒磷(1121)+TX、异狄氏剂(1122)+TX、EPBP(1123)+TX、EPN(297)+TX、保幼醚(1124)+TX、依立诺克丁(替代名称)[CCN]+TX、高氰戊菊酯(302)+TX、牛津郡丙硫磷(etaphos)(替代名称)[CCN]+TX、乙硫苯威(308)+TX、乙硫磷(309)+TX、乙虫腈(310)+TX、益硫磷-甲基(1134)+TX、灭线磷(312)+TX、甲酸乙酯(IUPAC名称)[CCN]+TX、乙基-DDD(别名)(1056)+TX、二溴化乙烯(316)+TX、二氯化乙烯(化学名称)(1136)+TX、环氧乙烷[CCN]+TX、醚菊酯(319)+TX、乙嘧硫磷(1142)+TX、EXD(1143)+TX、氨磺磷(323)+TX、苯线磷(326)+TX、抗螨唑(1147)+TX、皮蝇磷(1148)+TX、苯硫威(1149)+TX、芬氟司林(1150)+TX、杀螟硫磷(335)+TX、丁苯威(336)+TX、嘧酰虫胺(fenoxacrim)(1153)+TX、苯氧威(340)+TX、吡氯氰菊酯(1155)+TX、甲氰菊酯(342)+TX、吡螨胺(fenpyrad)(别名)+TX、丰索磷(1158)+TX、倍硫磷(346)+TX、倍硫磷-乙基[CCN]+TX、氰戊菊酯(349)+TX、氟虫腈(354)+TX、氟啶虫酰胺(358)+TX、氟虫酰胺(CAS登记号:272451-65-7)+TX、氟氯双苯隆(1168)+TX、氟螨脲(366)+TX、氟氰戊菊酯(367)+TX、联氟螨(1169)+TX、嘧虫胺[CCN]+TX、氟虫脲(370)+TX、三氟醚菊酯(1171)+TX、氟氯苯菊酯(372)+TX、氯胺氰菊酯(1184)+TX、FMC 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60-38(研究代码)(1328)+TX、芬硫磷(1330)+TX、苯醚菊酯(630)+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、对氯硫磷(1339)+TX、磷胺(639)+TX、磷化氢(IUPAC名称)(640)+TX、辛硫磷(642)+TX、辛硫磷-甲基(1340)+TX、甲胺嘧磷(pirimetaphos)(1344)+TX、抗蚜威(651)+TX、乙基嘧啶磷(1345)+TX、甲基嘧啶磷(652)+TX、聚氯二环戊二烯异构体类(IUPAC名称)(1346)+TX、氯化松节油(polychloroterpenes)(传统名称)(1347)+TX、亚砷酸钾[CCN]+TX、硫氰酸钾[CCN]+TX、丙炔菊酯(655)+TX、早熟素I(别名)[CCN]+TX、早熟素II(别名)[CCN]+TX、早熟素III(别名)[CCN]+TX、乙酰嘧啶磷(primidophos)(1349)+TX、丙溴磷(662)+TX、丙氟菊酯[CCN]+TX、蜱虱威(1354)+TX、猛杀威(1355)+TX、丙虫磷(1356)+TX、胺丙畏(673)+TX、残杀威(678)+TX、乙噻唑磷(1360)+TX、丙硫磷(686)+TX、发硫磷(1362)+TX、丙苯烃菊酯(protrifenbute)[CCN]+TX、吡蚜酮(688)+TX、吡唑硫磷(689)+TX、定菌磷(693)+TX、苄呋菊酯(pyresmethrin)(1367)+TX、除虫菊酯I(696)+TX、除虫菊酯II(696)+TX、除虫菊酯类(696)+TX、哒螨灵(699)+TX、啶虫丙醚(700)+TX、哒嗪硫磷(701)+TX、嘧螨醚(706)+TX、嘧硫磷(1370)+TX、吡丙醚(708)+TX、苦木提取物(quassia)(别名)[CCN]+TX、喹硫磷(quinalphos)(711)+TX、喹硫磷-甲基(1376)+TX、畜宁磷(1380)+TX、喹硫磷(quintiofos)(1381)+TX、R-1492(研究代码)(1382)+TX、雷复尼特(别名)[CCN]+TX、苄呋菊酯(719)+TX、鱼藤酮(722)+TX、RU 15525(研究代码)(723)+TX、RU 25475(研究代码)(1386)+TX、尼亚那(ryania)(别名)(1387)+TX、利阿诺定(传统名称)(1387)+TX、沙巴藜芦(别名)(725)+TX、八甲磷(1389)+TX、硫线磷(别名)+TX、塞拉菌素(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、SN72129(研究代码)(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(CCN)+TX、萨尔科福隆(sulcofuron)(746)+TX、萨尔科福隆钠(sulcofuron-sodium)(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(terbam)(别名)+TX、特丁硫磷(773)+TX、四氯乙烷[CCN]+TX、杀虫畏(777)+TX、四甲菊酯(787)+TX、θ氯氰菊酯(204)+TX、噻虫啉(791)+TX、塞芬诺克斯(thiafenox)(别名)+TX、噻虫嗪(792)+TX、苯噻硫磷(thicrofos)(1428)+TX、克虫威(1431)+TX、杀虫环(798)+TX、杀虫环草酸氢盐(798)+TX、硫双威(799)+TX、久效威(800)+TX、甲基乙拌磷(801)+TX、虫线磷(1434)+TX、杀虫单(thiosultap)(803)+TX、杀虫双(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、反式苄氯菊酯(transpermethrin)(1440)+TX、威菌磷(1441)+TX、唑蚜威(818)+TX、三唑磷(820)+TX、唑呀威(别名)+TX、敌百虫(824)+TX、三氯偏磷酸-3(trichlormetaphos-3)(别名)[CCN]+TX、毒壤膦(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、蚜灭磷(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、泽塔米林(zetamethrin)(别名)+TX、磷化锌(640)+TX、丙硫恶唑磷(zolaprofos)(1469)以及ZXI8901(研究代码)(858)+TX、氰虫酰胺[736994-63-19]+TX、氯虫酰胺[500008-45-7]+TX、唑螨氰(cyenopyrafen)[560121-52-0]+TX、丁氟螨酯[400882-07-7]+TX、氟虫吡喹(pyrifluquinazon)[337458-27-2]+TX、乙基多杀菌素(spinetoram)[187166-40-1+187166-15-0]+TX、螺虫乙酯[203313-25-1]+TX、砜虫啶(sulfoxaflor)[946578-00-3]+TX、丁虫腈(flufiprole)[704886-18-0]+TX、氯氟醚菊酯[915288-13-0]+TX、四氟醚菊酯(tetramethylfluthrin)[84937-88-2]+TX、三氟苯嘧啶(triflumezopyrim)(披露于WO2012/092115中)+TX,氟噁唑酰胺(fluxametamide)(WO 2007/026965)+TX、ε-甲氧苄氟菊酯[240494-71-7]+TX、ε-momfluorothrin[1065124-65-3]+TX、fluazaindolizine[1254304-22-7]+TX、氯碱丙炔菊酯[399572-87-3]+TX、fluxametamide[928783-29-3]+TX、氯氟氰虫酰胺(cyhalodiamide)[1262605-53-7]+TX、tioxazafen[330459-31-9]+TX、broflanilide[1207727-04-5]+TX、丁烯氟虫腈(flufiprole)[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中)+TX、环氧虫啶(描述于WO 2005/077934中)+TX、Spiropidion+TX、Afidopyropen+TX、flupyrimin+TX、Momfluorothrin+TX、κ-联苯菊酯+TX、κ-七氟菊酯+TX、Dichloromezotiaz+TX、Tetrachloraniliprole+TX、benzpyrimoxan+TX;
杀软体动物剂,其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(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(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、蜗螺杀(trifenmorph)(1454)+TX、混杀威(trimethacarb)(840)+TX、三苯基乙酸锡(IUPAC名称)(347)和三苯基氢氧化锡(IUPAC名称)(347)+TX、吡唑虫啶(pyriprole)[394730-71-3]+TX,
杀线虫剂,其选自由以下组成的物质组: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-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(benclothiaz)[CCN]+TX、苯菌灵(62)+TX、丁基哒螨灵(别名)+TX、克线丹(109)+TX、克百威(carbofuran)(118)+TX、二硫化碳(945)+TX、丁硫克百威(119)+TX、氯化苦(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、多拉克汀(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、灭线磷(312)+TX、二溴乙烷(316)+TX、苯线磷(326)+TX、fenpyrad(别名)+TX、丰索磷(1158)+TX、噻唑磷(408)+TX、丁硫环磷(1196)+TX、糠醛(别名)[CCN]+TX、GY-81(研究代码)(423)+TX、速杀硫磷[CCN]+TX、碘甲烷(IUPAC名称)(542)+TX、异酰胺磷(isamidofos)(1230)+TX、氯唑磷(1231)+TX、伊维菌素(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、溴甲烷(537)+TX、异硫氰酸甲酯(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、杀线威(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、虫线磷(1434)+TX、三唑磷(820)+TX、唑蚜威(triazuron)(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、氟吡菌酰胺+TX,
硝化抑制剂,其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,
植物活化剂,其选自由以下组成的物质组:阿拉酸式苯(acibenzolar)(6)+TX、阿拉酸式苯-S-甲基(6)+TX、噻菌灵(probenazole)(658)和大虎杖(Reynoutriasachalinensis)提取物(别名)(720)+TX,
杀鼠剂,其选自由以下组成的物质组: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、氯醛糖(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(273)+TX、钙化醇(301)+TX、氟鼠灵(357)+TX、氟乙酰胺(379)+TX、氟鼠啶(1183)+TX、氟鼠啶盐酸盐(1183)+TX、γ-HCH(430)+TX、HCH(430)+TX、氰化氢(444)+TX、碘甲烷(IUPAC名称)(542)+TX、林旦(430)+TX、磷化镁(IUPAC名称)(640)+TX、溴甲烷(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)以及磷化锌(640)+TX,
增效剂,其选自由以下组成的物质组:2-(2-丁氧基乙氧基)乙基胡椒酸酯(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、具有橙花叔醇的法呢醇(别名)(324)+TX、MB-599(研究代码)(498)+TX、MGK264(研究代码)(296)+TX、增效醚(piperonyl butoxide)(649)+TX、增效醛(piprotal)(1343)+TX、增效酯(propyl isomer)(1358)+TX、S421(研究代码)(724)+TX、增效散(sesamex)(1393)+TX、芝麻林素(sesasmolin)(1394)和亚砜(1406)+TX,
动物驱避剂,其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、双胍辛盐(guazatine)(422)+TX、双胍辛乙酸盐(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,
杀病毒剂,其选自由以下组成的物质组:衣马宁(别名)[CCN]和利巴韦林(别名)[CCN]+TX,
创伤保护剂,其选自由以下组成的物质组:氧化汞(512)+TX、辛噻酮(octhilinone)(590)和甲基托布津(802)+TX,
以及生物活性化合物,其选自由以下组成的物质组: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(pyrifenox)[88283-41-4]+TX、丙氯灵[67747-09-5]+TX、丙环唑[60207-90-1]+TX、硅氟唑(simeconazole)[149508-90-7]+TX、戊唑醇[107534-96-3]+TX、氟醚唑[112281-77-3]+TX、三唑酮[43121-43-3]+TX、三唑酮[55219-65-3]+TX、氟菌唑[99387-89-0]+TX、灭菌唑[131983-72-7]+TX、三环苯嘧醇[12771-68-5]+TX、氯苯嘧啶醇[60168-88-9]+TX、氟氯苯嘧啶醇[63284-71-9]+TX、乙嘧酚磺酸酯(bupirimate)[41483-43-6]+TX、甲菌定(dimethirimol)[5221-53-4]+TX、乙菌定(ethirimol)[23947-60-6]+TX、十二环吗啉[1593-77-7]+TX、苯锈啶(fenpropidine)[67306-00-7]+TX、丁苯吗啉[67564-91-4]+TX、螺环菌胺[118134-30-8]+TX、十三吗啉[81412-43-3]+TX、嘧菌环胺[121552-61-2]+TX、嘧菌胺[110235-47-7]+TX、嘧霉胺(pyrimethanil)[53112-28-0]+TX、拌种咯[74738-17-3]+TX、咯菌腈(fludioxonil)[131341-86-1]+TX、苯霜灵(benalaxyl)[71626-11-4]+TX、呋霜灵(furalaxyl)[57646-30-7]+TX、甲霜灵[57837-19-1]+TX、R甲霜灵[70630-17-0]+TX、呋酰胺[58810-48-3]+TX、噁霜灵(Oxadixyl)[77732-09-3]+TX、苯菌灵[17804-35-2]+TX、多菌灵[10605-21-7]+TX、咪菌威(debacarb)[62732-91-6]+TX、麦穗宁[3878-19-1]+TX、噻苯达唑[148-79-8]+TX、乙菌利(chlozolinate)[84332-86-5]+TX、菌核利(dichlozoline)[24201-58-9]+TX、异菌脲(Iprodione)[36734-19-7]+TX、myclozoline[54864-61-8]+TX、腐霉利(procymidone)[32809-16-8]+TX、乙烯菌核利(vinclozoline)[50471-44-8]+TX、啶酰菌胺(boscalid)[188425-85-6]+TX、萎锈灵[5234-68-4]+TX、甲呋酰苯胺[24691-80-3]+TX、氟酰胺(Flutolanil)[66332-96-5]+TX、灭锈胺[55814-41-0]+TX、氧化萎锈灵[5259-88-1]+TX、吡噻菌胺(penthiopyrad)[183675-82-3]+TX、噻呋菌胺[130000-40-7]+TX、双胍盐[108173-90-6]+TX、多果定(dodine)[2439-10-3][112-65-2](游离键)+TX、双胍辛胺(iminoctadine)[13516-27-3]+TX、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[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(propineb)[12071-83-9]+TX、塞仑[137-26-8]+TX、代森锌[12122-67-7]+TX、福美锌[137-30-4]+TX、敌菌丹(captafol)[2425-06-1]+TX、克菌丹[133-06-2]+TX、抑菌灵[1085-98-9]+TX、唑呋草(fluoroimide)[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、氯化铜(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(mancopper)[53988-93-5]+TX、喹啉铜(oxine-copper)[10380-28-6]+TX、敌螨普(dinocap)[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(isoprothiolane)[50512-35-1]+TX、氯瘟磷(phosdiphen)[36519-00-3]+TX、吡菌磷(pyrazophos)[13457-18-6]+TX、甲基立枯磷(tolclofos-methyl)[57018-04-9]+TX、阿拉酸式苯-S-甲基(acibenzolar-S-methyl)[135158-54-2]+TX、敌菌灵[101-05-3]+TX、苯噻菌胺[413615-35-7]+TX、灭瘟素(blasticidin)-S[2079-00-7]+TX、灭螨猛(chinomethionat)[2439-01-2]+TX、地茂散(chloroneb)[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(dichlone)[117-80-6]+TX、双氯氰菌胺(diclocymet)[139920-32-4]+TX、哒菌酮(diclomezine)[62865-36-5]+TX、氯硝胺(dicloran)[99-30-9]+TX、乙霉威(diethofencarb)[87130-20-9]+TX、烯酰吗啉[110488-70-5]+TX、SYP-LI90(氟吗啉)[211867-47-9]+TX、二噻农(dithianon)[3347-22-6]+TX、噻唑菌胺(ethaboxam)[162650-77-3]+TX、土菌灵(etridiazole)[2593-15-9]+TX、恶唑菌酮[131807-57-3]+TX、咪唑菌酮(fenamidone)[161326-34-7]+TX、稻瘟酰胺(Fenoxanil)[115852-48-7]+TX、三苯锡(fentin)[668-34-8]+TX、嘧菌腙(ferimzone)[89269-64-7]+TX、氟啶胺(fluazinam)[79622-59-6]+TX、氟吡菌胺(fluopicolide)[239110-15-7]+TX、磺菌胺(flusulfamide)[106917-52-6]+TX、环酰菌胺[126833-17-8]+TX、三乙膦酸铝(fosetyl-aluminium)[39148-24-8]+TX、恶霉灵(hymexazol)[10004-44-1]+TX、丙森锌[140923-17-7]+TX、IKF-916(赛座灭(Cyazofamid))[120116-88-3]+TX、春雷霉素(kasugamycin)[6980-18-3]+TX、磺菌威(methasulfocarb)[66952-49-6]+TX、苯菌酮[220899-03-6]+TX、戊菌隆(pencycuron)[66063-05-6]+TX、苯酞[27355-22-2]+TX、多氧霉素(polyoxins)[11113-80-7]+TX、噻菌灵(probenazole)[27605-76-1]+TX、霜霉威(propamocarb)[25606-41-1]+TX、碘喹唑酮(proquinazid)[189278-12-4]+TX、咯喹酮(pyroquilon)[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(triazoxide)[72459-58-6]+TX、三环唑[41814-78-2]+TX、嗪氨灵[26644-46-2]+TX、有效霉素[37248-47-8]+TX、苯酰菌胺(zoxamide)(RH7281)[156052-68-5]+TX、双炔酰菌胺(mandipropamid)[374726-62-2]+TX、吡唑萘菌胺(isopyrazam)[881685-58-1]+TX、氟唑环菌胺(sedaxane)[874967-67-6]+TX、3-二氟甲基-1-甲基-1H-吡唑-4-羧酸(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中)+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中)+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]甲基-环丙甲酸酯[915972-17-7]+TX以及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、lancotrione[1486617-21-3]+TX、氯氟吡啶酯[943832-81-3]+TX、ipfentrifluconazole[1417782-08-1]+TX、mefentrifluconazole[1417782-03-6]+TX、quinofumelin[861647-84-9]+TX、右旋反式氯丙炔菊酯[399572-87-3]+TX、氯氟氰虫酰胺[1262605-53-7]+TX、三氟咪啶酰胺[1254304-22-7]+TX、fluxametamide[928783-29-3]+TX、ε-甲氧苄氟菊酯[240494-71-7]+TX、ε-momfluorothrin[1065124-65-3]+TX、氟唑菌酰羟胺(pydiflumetofen)[1228284-64-7]+TX、κ-联苯菊酯[439680-76-9]+TX、broflanilide[1207727-04-5]+TX、dicloromezotiaz[1263629-39-5]+TX、dipymetitrone[16114-35-5]+TX、pyraziflumid[942515-63-1]+TX和κ-七氟菊酯[391634-71-2]+TX、fenpicoxamid[517875-34-2]+TX;氟苯吡咯烷酮+TX、benzpyrimoxan[1449021-97-9]+TX;isocycloseram+TX、rescalure[64309-03-1]+TX;aminopyrifen[1531626-08-0]+TX;以及
微生物,其包括:鲁氏不动杆菌+TX、支顶孢属突起菌+TX+TX、支顶孢属头孢+TX+TX、支顶孢属柿(Acremonium diospyri)+TX、支顶孢属倒棍棒状的+TX、苹卷蛾颗粒体病毒属(AdoxGV)+TX、放射形土壤杆菌菌株K84+TX、交链格孢菌+TX、链格孢决明子+TX、链格孢属性(Alternaria destruens)+TX、白粉寄生孢+TX、黄曲霉AF36+TX、黄曲霉NRRL 21882+TX、曲霉属+TX、出芽短梗霉菌+TX、固氮螺菌属+TX、(+TX、TAZO)+TX、固氮菌属+TX、固氮菌属chroocuccum+TX、固氮菌属囊肿(BionaturalBlooming)+TX、解淀粉芽孢杆菌+TX、蜡样芽孢杆菌+TX、芽孢杆菌属菌株(Bacillus chitinosporus strain)CM-1+TX、芽孢杆菌属菌株(Bacillus chitinosporusstrain 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、B环状芽孢杆菌+TX、坚硬芽孢杆菌(+TX、+TX、)+TX、坚硬芽孢杆菌菌株I-1582+TX、巨大芽孢杆菌+TX、巨大芽孢杆菌+TX、巨大芽孢杆菌+TX、蕈状芽孢杆菌菌株AQ726+TX、乳头状瘤芽孢杆菌(Milky Spore)+TX、短小芽孢杆菌属+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、球形芽孢杆菌(Bacillus spahericus)+TX、芽孢杆菌+TX、芽孢杆菌菌株AQ175+TX、芽孢杆菌菌株AQ177+TX、芽孢杆菌菌株AQ178+TX、枯草芽孢杆菌属菌株QST 713(+TX、+TX、)+TX、枯草芽孢杆菌属菌株QST 714+TX、枯草芽孢杆菌属菌株AQ153+TX、枯草芽孢杆菌属菌株AQ743+TX、枯草芽孢杆菌属菌株QST3002+TX、枯草芽孢杆菌属菌株QST3004+TX、枯草芽孢杆菌属变种解淀粉芽孢杆菌菌株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(Bacillus thuringiensis aizawai)GC 91+TX、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensis israelensis)(+TX、+TX、)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensiskurstaki)(+TX、+TX、+TX、+TX、Scutella+TX、Turilav+TX、+TX、Dipel+TX、+TX、)+TX、苏云金芽孢杆菌库尔斯塔克亚种BMP 123+TX、苏云金芽孢杆菌库尔斯塔克亚种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、细菌属(+TX、+TX、)+TX、密执安棍状杆菌(Clavipacter michiganensis)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、灰葡萄孢霉+TX、大豆慢生型根瘤菌+TX、短短小芽孢杆菌+TX、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis tenebrionis)+TX、BtBooster+TX、洋葱伯克霍尔德菌(+TX、+TX、Blue)+TX、伯克霍尔德菌(Burkholderia gladii)+TX、唐菖蒲伯克霍尔德菌+TX、伯克霍尔德菌属+TX、加拿大蓟真菌(CBH Canadian)+TX、奶酪假丝酵母+TX、无名假丝酵母+TX、Candidafructus+TX、光滑念珠菌+TX、吉利蒙念珠菌(Candida guilliermondii)+TX、口津假丝酵母+TX、橄榄假丝酵母菌株O+TX、近平滑假丝酵母+TX、菌膜假丝酵母+TX、铁红假丝酵母+TX、拉考夫假丝酵母(Candida reukaufii)+TX、齐藤假丝酵母(Candida saitoana)(+TX、)+TX、清酒假丝酵母+TX、假丝酵母属+TX、纤细假丝酵母+TX、戴氏西地西菌(Cedecea dravisae)+TX、产黄纤维单胞菌+TX、螺卷毛壳+TX、球毛壳菌+TX、铁杉紫色杆菌(Chromobacteriumsubtsugae)菌株PRAA4-1T+TX、枝状枝孢菌+TX、尖孢枝孢+TX、Cladosporium chlorocephalum+TX、枝孢属+TX、极细枝孢霉+TX、粉红粘帚霉+TX、尖孢炭疽菌(Colletotrichum acutatum)+TX、盾壳霉(Cotans)+TX、盾壳霉属+TX、浅白隐球酵母+TX、土生隐球菌+TX、Cryptococcusinfirmo-miniatus+TX、罗伦隐球酵母+TX、苹果异形小卷蛾颗粒体病毒+TX、坎平贪铜菌(Cupriavidus campinensis)+TX、苹果蠹蛾颗粒体病毒+TX、苹果蠹蛾颗粒体病毒(+TX、Madex+TX、Madex Max/)+TX、Cylindrobasidium laeve+TX、枝双孢霉属(Cylindrocladium)+TX、汉逊德巴利酵母(Debaryomyces hansenii)+TX、Drechslerahawaiinensis+TX、阴沟肠杆菌(Enterobactercloacae)+TX、肠杆菌科(Enterobacteriaceae)+TX、毒力虫霉(Entomophtora virulenta)+TX、附球菌(Epicoccumnigrum)+TX、黑附球菌(Epicoccum purpurascens)+TX、附球孢属物种+TX、Filobasidium floriforme+TX、锐顶镰孢菌+TX、厚孢镰刀菌+TX、尖孢镰刀菌(/Biofox)+TX、层出镰刀菌+TX、镰刀菌属物种+TX、白地霉(Galactomyces geotrichum)+TX、链孢粘帚霉(Gliocladium catenulatum)(+TX、)+TX、粉红粘帚霉(Gliocladium roseum)+TX、粘帚霉属物种+TX、绿粘帚霉+TX、颗粒体病毒+TX、嗜盐盐芽孢杆菌(Halobacillus halophilus)+TX、岸喜盐芽孢杆菌(Halobacilluslitoralis)+TX、特氏盐芽孢杆菌(Halobacillus trueperi)+TX、盐单胞菌属物种+TX、冰下盐单胞菌(Halomonas subglaciescola)+TX、多变盐弧菌(Halovibriovariabilis)+TX、葡萄汁有孢汉逊酵母+TX、棉铃虫核型多角体病毒+TX、谷实夜蛾核型多角体病毒+TX、异黄酮-芒柄花黄素+TX、柠檬克勒克酵母+TX、克勒克酵母属物种+TX、大链壶菌(Lagenidium giganteum)+TX、长孢蜡蚧菌(Lecanicillium longisporum)+TX、蝇蚧疥霉(Lecanicilliummuscarium)+TX、舞毒蛾核型多角体病毒+TX、嗜盐海球菌+TX、格氏梅拉菌(Meira geulakonigii)+TX、绿僵菌+TX、绿僵菌(Destruxin)+TX、Metschnikowia fruticola+TX、美极梅奇酵母(Metschnikowia pulcherrima)+TX、Microdochium dimerum+TX、天蓝色小单孢菌(Micromonospora coerulea)+TX、Microsphaeropsis ochracea+TX、恶臭白色真菌(Muscodor albus)620+TX、Muscodor roseus菌株A3-5+TX、菌根属物种(Mycorrhizae spp.)(+TX、Root)+TX、疣孢漆斑菌菌株AARC-0255+TX、BROS+TX、Ophiostoma piliferum菌株D97+TX、粉质拟青霉(Paecilomyces farinosus)+TX、玫烟色拟青霉(+TX、)+TX、淡紫拟青霉(Paecilomyces lilacinus)(Biostat)+TX、淡紫拟青霉菌株251(MeloCon)+TX、多粘类芽孢杆菌+TX、成团泛菌(BlightBan)+TX、泛菌属物种+TX、巴斯德氏芽菌属物种+TX、拟斯扎瓦巴氏杆菌(Pasteuria nishizawae)+TX、黄灰青霉+TX、拜赖青霉(Penicilliumbillai)(+TX、)+TX、短密青霉+TX、常现青霉+TX、灰黄青霉+TX、产紫青霉+TX、青霉菌属物种+TX、纯绿色肯霉+TX、大伏革菌(Phlebiopsis gigantean)+TX、解磷细菌+TX、隐地疫霉+TX、棕榈疫霉+TX、异常毕赤酵母+TX、季也蒙毕赤酵母(Pichia guilermondii)+TX、膜醭毕赤氏酵母+TX、指甲毕赤酵母+TX、树干毕赤酵母+TX、铜绿假单胞菌+TX、致金色假单胞菌(Pseudomonas aureofasciens)(Spot-Less)+TX、洋葱假单胞菌+TX、绿针假单胞菌+TX、皱褶假单胞菌(Pseudomonas corrugate)+TX、荧光假单胞菌菌株A506(BlightBan)+TX、恶臭假单胞菌+TX、Pseudomonas reactans+TX、假单胞菌属物种+TX、丁香假单胞菌+TX、绿黄假单胞菌+TX、荧光假单胞菌+TX、Pseudozyma flocculosa菌株PF-A22 UL(Sporodex)+TX、纵沟柄锈菌(Puccinia canaliculata)+TX、Puccinia thlaspeos(Wood)+TX、侧雄腐霉菌(Pythium oligandrum)+TX、寡雄腐霉(+TX、)+TX、缠器腐霉+TX、水生拉恩菌(Rhanella aquatilis)+TX、拉恩菌属物种(Rhanella spp.)+TX、根瘤菌(Rhizobia)(+TX、)+TX、丝核菌(Rhizoctonia)+TX、球状红球菌(Rhodococcus globerulus)菌株AQ719+TX、双倒卵形红冬孢酵母菌(Rhodosporidiumdiobovatum)+TX、圆红冬孢酵母菌(Rhodosporidium toruloides)+TX、红酵母属物种(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、玫瑰色盐水球菌(Salinococcus roseus)+TX、小核盘菌(Sclerotinia minor)+TX、小核盘菌+TX、柱顶孢霉属物种(Scytalidium spp.)+TX、Scytalidiumuredinicola+TX、甜菜夜蛾核型多角体病毒(Spodoptera exigua nuclear polyhedrosisvirus)(+TX、)+TX、粘质沙雷氏菌(Serratia marcescens)+TX、普城沙雷菌(Serratia plymuthica)+TX、沙雷氏菌属物种(Serratia spp.)+TX、粪生粪壳菌(Sordaria fimicola)+TX、海灰翅夜蛾核型多角体病毒(Spodoptera littoralisnucleopolyhedrovirus)+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、白丘链霉菌(Streptomyces albaduncus)+TX、脱叶链霉菌(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 griseoviridis)+TX、利迪链霉菌(Streptomyces lydicus)+TX、利迪链霉菌WYEC-108+TX、紫色链霉菌(Streptomyces violaceus)+TX、小铁艾酵母(Tilletiopsis minor)+TX、铁艾酵母属物种(Tilletiopsis spp.)+TX、棘孢木霉(Trichoderma asperellum)(T34)+TX、盖姆斯木霉(Trichoderma gamsii)+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(Trichoderma harzianum)T-22(+TX、PlantShield+TX、+TX、)+TX、哈茨木霉(Trichoderma harzianum)T-39+TX、非钩木霉(Trichodermainhamatum)+TX、康宁木霉(Trichoderma koningii)+TX、木霉属物种(Trichoderma spp.)LC 52+TX、木素木霉(Trichoderma lignorum)+TX、长柄木霉(Trichodermalongibrachiatum)+TX、多孢木霉(Trichoderma polysporum) +TX、紫杉木霉(Trichoderma taxi)+TX、绿色木霉(Trichoderma virens)+TX、绿色木霉(原来称为绿色粘帚霉(Gliocladium virens)GL-21)+TX、绿色木霉(Trichodermaviride)+TX、绿色木霉菌株ICC 080+TX、茁芽丝孢酵母(Trichosporonpullulans)+TX、毛孢子菌属物种(Trichosporon spp.)+TX、单端孢属物种(Trichotheciumspp.)+TX、粉红单端孢(Trichothecium roseum)+TX、Typhula phacorrhiza菌株94670+TX、Typhula phacorrhiza菌株94671+TX、黑细基格孢(Ulocladium atrum)+TX、奥德曼细基格孢(Ulocladium oudemansii)+TX、玉蜀黍黑粉菌(Ustilago maydis)+TX、各种细菌和补充微量营养素+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、死海枝芽孢杆菌(Virgibaclillus marismortui)+TX、野油菜黄单胞菌pv.Poae+TX、伯氏致病杆菌+TX、嗜线虫致病杆菌;以及
植物提取物,包括: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(Chenopodiumambrosioides 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-胡椒薄荷和百里香油提取物(Garden insect)+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、Nepeta catarina+TX、烟碱+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-迷迭香和胡椒薄荷提取物混合物(EF)+TX、丁香-胡椒薄荷-大蒜油和薄荷混合物(Soil)+TX、高岭土+TX、褐藻的贮存葡聚糖以及
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)(Snip7Fly+TX、Starbar Premium Fly)+TX、梨小食心虫信息素(3M oriental fruit mothsprayable)+TX、桃透翅蛾(Peachtree Borer)信息素+TX、番茄蛲虫(Tomato Pinworm)信息素(3M Sprayable)+TX、衣透斯特粉末(Entostat powder)(来自棕榈树的提取物)(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-基乙酸酯+TX、2-甲基-1-丁醇+TX、乙酸钙+TX、+TX、+TX、+TX、薰衣草千里酸酯(Lavandulyl senecioate);以及
宏生物剂(Macrobial),包括:短距蚜小蜂+TX、阿尔蚜茧蜂(Aphidius ervi)+TX、Acerophagus papaya+TX、二星瓢虫+TX、二星瓢虫+TX、二星瓢虫+TX、串茧跳小蜂(Ageniaspis citricola)+TX、巢蛾多胚跳小蜂+TX、安德森钝绥螨(Amblyseius andersoni)(+TX、)+TX、加州钝绥螨(Amblyseius californicus)(+TX、)+TX、黄瓜钝绥螨(+TX、Bugline)+TX、伪钝绥螨+TX、斯氏钝绥螨(Bugline+TX、)+TX、奥氏钝绥螨+TX、粉虱细蜂(Amitus hesperidum)+TX、原樱翅缨小蜂(Anagrus atomus)+TX、暗腹长索跳小蜂(Anagyrus fusciventris)+TX、卡玛长索跳小蜂(Anagyrus kamali)+TX、Anagyrusloecki+TX、粉蚧长索跳小蜂(Anagyrus pseudococci)+TX、红蜡蚧扁角跳小蜂(Anicetus benefices)+TX、金小蜂(Anisopteromalus calandrae)+TX、林地花蝽(Anthocoris nemoralis)+TX、短距蚜小蜂(+TX、)+TX、短翅蚜小蜂(Aphelinus asychis)+TX、棉蚜寄生蜂(Aphidiuscolemani)+TX、阿尔蚜茧蜂+TX、烟蚜茧蜂+TX、桃赤蚜蚜茧蜂+TX、食蚜瘿蚊+TX、食蚜瘿蚊+TX、岭南黄蚜小蜂+TX、印巴黄蚜小蜂+TX、哈氏长尾啮小蜂(Aprostocetus hagenowii)+TX、蚁形隐翅甲(Atheta coriaria)+TX、熊蜂属物种+TX、欧洲熊蜂(Natupol)+TX、欧洲熊蜂(+TX、)+TX、Cephalonomiastephanoderis+TX、黑背唇瓢虫(Chilocorus nigritus)+TX、普通草蛉(Chrysoperlacarnea)+TX、普通草蛉+TX、红通草蛉(Chrysoperlarufilabris)+TX、Cirrospilus ingenuus+TX、四带瑟姬小蜂(Cirrospilusquadristriatus)+TX、白星橘啮小蜂(Citrostichus phyllocnistoides)+TX、Closterocerus chamaeleon+TX、Closterocerus属物种+TX、Coccidoxenoides perminutus+TX、泊蚜小蜂(Coccophagus cowperi)+TX、赖食蚧蚜小蜂(Coccophaguslycimnia)+TX、螟黄足盘绒茧蜂+TX、菜蛾绒茧蜂+TX、孟氏隐唇瓢虫(+TX、)+TX、日本方头甲+TX、西伯利亚离颚茧蜂+TX、西伯利亚离颚茧蜂+TX、豌豆潜叶蝇姬小蜂+TX、小黑瓢虫(Delphastuscatalinae)+TX、Delphastus pusillus+TX、Diachasmimorpha krausii+TX、长尾潜蝇茧蜂+TX、Diaparsis jucunda+TX、阿里食虱跳小蜂(Diaphorencyrtusaligarhensis)+TX、豌豆潜叶蝇姬小蜂+TX、豌豆潜叶蝇姬小蜂(+TX、)+TX、西伯利亚离颚茧蜂(+TX、)+TX、歧脉跳小蜂属物种+TX、盾蚧长缨蚜小蜂+TX、丽蚜小蜂(Encarsia+TX、+TX、)+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+TX、Eretmoceris siphonini+TX、加州浆角蚜小蜂(Eretmoceruscalifornicus)+TX、浆角蚜小蜂(Eretmocerus eremicus)(+TX、Eretline)+TX、浆角蚜小蜂(Eretmocerus eremicus)+TX、海氏桨角蚜小蜂+TX、蒙氏桨角蚜小蜂(Eretmocerus mundus)(+TX、Eretline)+TX、Eretmocerussiphonini+TX、四斑光缘瓢虫(Exochomus quadripustulatus)+TX、食螨瘿蚊(Feltiellaacarisuga)+TX、食螨瘿蚊(Feltiella acarisuga)+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(Franklinothripsvespiformis)+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、NemAttack+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(Lbalialeucospoides)+TX、Lecanoideus floccissimus+TX、Lemophagus errabundus+TX、三色丽突跳小蜂(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(Lysiphlebustestaceipes)+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(Micromusangulatus)+TX、黄色花翅跳小蜂(Microterys flavus)+TX、Muscidifurax raptorellus和Spalangia cameroni+TX、Neodryinustyphlocybae+TX、加州新小绥螨(Neoseiulus californicus)+TX、瓜钝绥螨(Neoseiuluscucumeris)+TX、虚伪新小绥螨(Neoseiulus fallacis)+TX、Nesideocoris tenuis(+TX、)+TX、古铜黑蝇(Ophyraaenescens)+TX、狡小花蝽(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(Oriusstrigicollis)+TX、Pauesia juniperorum+TX、酸酱瓢虫腹柄姬小蜂(Pediobius foveolatus)+TX、Phasmarhabditis hermaphrodita+TX、Phymastichus coffea+TX、Phytoseiulus macropilus+TX、智利小植绥螨(Phytoseiuluspersimilis)(+TX、Phytoline)+TX、斑腹刺益蝽(Podisus maculiventris)+TX、Pseudacteon curvatus+TX、Pseudacteon obtusus+TX、Pseudacteontricuspis+TX、Pseudaphycus maculipennis+TX、Pseudleptomastix mexicana+TX、具毛嗜木虱跳小蜂(Psyllaephagus pilosus)+TX、同色短背茧蜂(Psyttalia concolor)(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(Sitobion avenae)+TX、小卷蛾斯氏线虫(Steinernemacarpocapsae)(Nematac+TX、+TX、BioNem+TX、+TX、+TX、)+TX、夜蛾斯氏线虫(+TX、Nemasys+TX、BioNem+TX、+TX、+TX、+TX、Exhibitline+TX、+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(Steinernema spp.)+TX、Steinernematid属(Guardian)+TX、深点食螨瓢虫(Stethoruspunctillum)+TX、亮腹釉小蜂(Tamarixia radiate)+TX、Tetrastichussetifer+TX、Thripobius semiluteus+TX、中华长尾小蜂(Torymus sinensis)+TX、甘蓝夜蛾赤眼蜂(Trichogramma brassicae)(Tricholine)+TX、甘蓝夜蛾赤眼蜂(Trichogramma brassicae)+TX、广赤眼蜂(Trichogrammaevanescens)+TX、微小赤眼蜂(Trichogramma minutum)+TX、玉米螟赤眼蜂(Trichogrammaostriniae)+TX、宽脉赤眼蜂(Trichogramma platneri)+TX、短管赤眼蜂(Trichogrammapretiosum)+TX、螟黑点瘤姬蜂(Xanthopimpla stemmator);以及
其他生物制剂,包括:脱落酸+TX、+TX、银叶菌(Chondrostereumpurpureum)(Chontrol)+TX、盘长孢状刺盘孢+TX、辛酸铜+TX、δ捕捉物(Delta trap)(Trapline)+TX、解淀粉欧文氏菌(Harpin)(+TX、Ni-HIBIT Gold)+TX、磷酸高铁+TX、漏斗捕捉物(Funnel trap)(Trapline)+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冰雹捕捉物(hail trap)(Trapline)+TX、寄生性昆虫南美食甲茧蜂(Microctonus hyperodae)+TX、Mycoleptodiscus terrestris+TX、+TX、+TX、+TX、信息素罗网(Thripline)+TX、碳酸氢钾+TX、脂肪酸的钾盐+TX、硅酸钾溶液+TX、碘化钾+硫氰酸钾+TX、+TX、蜘蛛毒+TX、蝗虫微孢子虫(Semaspore Organic Grasshopper)+TX、粘捕捉物(Trapline+TX、Rebell)+TX以及捕捉物(Takitrapline y+)+TX;
或选自以下的生物活性化合物或试剂:溴氟菊酯+TX、氟螨嗪(Diflovidazine)+TX、Flometoquin+TX、Fluhexafon+TX、小菜蛾颗粒体病毒+TX、苹果蠹蛾颗粒体病毒+TX、新烟磷(Imicyafos)+TX、烟芽夜蛾核多角体病毒+TX、Heliothis punctigera核多角体病毒+TX、玉米穗夜蛾核多角体病毒+TX、草地贪夜蛾核多角体病毒+TX、小菜蛾核多角体病毒+TX、对伞花烃+TX、Pyflubumide+TX、Pyrafluprole+TX、QRD 420+TX、QRD 452+TX、QRD 460+TX、萜类混合物+TX、萜类+TX、氟氰虫酰胺(Tetraniliprole)+TX和α-萜品烯+TX;
或由代码+TX提及的活性物质,如代码AE 1887196(BSC-BX60309)+TX、代码NNI-0745GR+TX、代码IKI-3106+TX、代码JT-L001+TX、代码ZNQ-08056+TX、代码IPPA152201+TX、代码HNPC-A9908(CAS:[660411-21-2])+TX、代码HNPC-A2005(CAS:[860028-12-2])+TX、代码JS118+TX、代码ZJ0967+TX、代码ZJ2242+TX、代码JS7119(CAS:[929545-74-4])+TX、代码SN-1172+TX、代码HNPC-A9835+TX、代码HNPC-A9955+TX、代码HNPC-A3061+TX、代码Chuanhua89-1+TX、代码IPP-10+TX、代码ZJ3265+TX、代码JS9117+TX、代码ZJ3757+TX、代码ZJ4042+TX、代码ZJ4014+TX、代码ITM-121+TX、代码DPX-RAB55(DKI-2301)+TX、代码NA-89+TX、代码MIE-1209+TX、代码MCI-8007+TX、代码BCS-CL73507+TX、代码S-1871+TX、代码DPX-RDS63+TX、代码AKD-1193+TX;
或选自以下的其他生物活性化合物或试剂:Quinofumelin+TX、mefentrifluconazol+TX、fenpicoxamid+TX、fluindapyr+TX、inpyrfluxam+TX或indiflumetpyr+TX、isoflucypram+TX、pyrapropoyne+TX、florylpicoxamid+TX、metyltetraprole+TX、ipflufenoquin+TX、pyridachlometyl+TX或chlopyridiflu+TX、四氯虫酰胺(tetrachlorantraniliprole)+TX、tetrachloraniliprole+TX、Tetflupyrolimet+TX、Triflufenpyrrolidone+TX、Tyclopyrazoflor+TX、flupyrimin+TX或pyrifluramide+TX、benzpyrimoxan+TX、beflubutamid-M+TX、Benzosufyl+TX或oxazosulfyl+TX、乙唑螨腈(etpyrafen)+TX、acynonapyr+TX或pyrinonafen+TX、氧代三酮(oxotrione)+TX、bixlozone+TX或clofendizone+TX或dicloroxizone+TX、cyclopyranil+TX或pyrazocyclonil+TX或cyclopyrazonil+TX、α-溴敌隆+TX、Oxathiapiprolin+TX、Fluopyram+TX,Penflufen+TX、Fluoxopyrosad+TX、fluoxapiprolin+TX和Flupyradifurone+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[杀有害生物剂手册]”[The Pesticide Manual-AWorld Compendium[杀有害生物剂手册-全球概览];第13版;编辑:C.D.S.TomLin;The British Crop Protection Coimcil[英国农作物保护委员会]]中,它们在其中以上文对于特定化合物的圆括号中所给出的条目编号来描述;例如化合物“阿维菌素”以条目编号(1)来描述。在“[CCN]”在上文添加到特定化合物的情况下,所述的化合物包括在“Compendium of Pesticide Common Names[杀有害生物剂通用名纲要]”中,其可以在互联网[A.Wood;Compendium of Pesticide Common Names,Copyright1995-2004]上获得;例如,化合物“乙酰虫腈”描述于互联网地址http://www.alanwood.net/pesticides/acetoprole.html。
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”。若名称不是“通用名”,则所使用的名称种类以特定化合物的圆括号中所给出的名称来代替;在这种情况下,使用IUPAC名称、IUPAC/化学文摘名、“化学名称”、“传统名称”、“化合物名称”或“研究代码”,或若既不使用那些名称之一也不使用“通用名”,则使用“别名”。“CAS登记号”意指化学文摘登记号。
选自表Y-1至Y-8、X-1至X-8、U-1至U-2和V-1至V-6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Y-1至Y-8、X-1至X-8、U-1至U-2和V-1至V-6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,尤其是从50:1至1:50的混合比,更尤其是处于从20:1至1:20的比率,甚至更尤其是从10:1至1:10,非常尤其是从5:1和1:5,特别优选的从2:1至1:2的比率,并且同样优选的是从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,所述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Y-1至Y-8、X-1至X-8、U-1至U-2和V-1至V-6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(所述混合物由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Y-1至Y-8、X-1至X-8、U-1至U-2和V-1至V-6和表P的具有式I的化合物和如上文所述的活性成分的顺序对于实施本发明并不是至关重要的。
根据本发明的组合物还可以包含其他固体或液体助剂,如稳定剂,例如未环氧化的或环氧化的植物油(例如环氧化的椰子油、菜籽油或大豆油),消泡剂(例如硅酮油),防腐剂,粘度调节剂,粘合剂和/或增粘剂,肥料或其他用于获得特定效果的活性成分,例如杀细菌剂、杀真菌剂、杀线虫剂、植物活化剂、杀软体动物剂或除草剂。
根据本发明的组合物是以本身已知的方式,在不存在助剂的情况下,例如通过研磨、筛选和/或压缩固体活性成分;和在至少一种助剂的存在下,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至2000g活性成分、尤其是10g/ha至1000g/ha、优选地是10g/ha至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(叶施用),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,所述活性成分可以通过根系统(内吸作用)到达植物,这是通过用液体组合物将这些植物的场所浸湿或者通过将呈固体形式的活性成分引入植物的场所(例如引入土壤,例如以颗粒的形式(土施))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。
本发明的化合物及其组合物还适合于植物繁殖材料(例如种子,像果实、块茎或籽粒,或者苗圃植物)的保护,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,所述化合物可以施用至种子籽粒(涂覆),这是通过将籽粒浸渍入液体组合物中或通过施用固体组合物层实现的。还可能在该繁殖材料被种植在施用场地时施用这些组合物,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如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,并且通常在每100kg种子1克至200克之间、优选在每100kg种子5克至150克之间,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意指真正的种子。
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所述种子材料中,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,所述活性成分在所述种子的表面。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供使用。此外,由此使得包括用具有式(I)的化合物处理过的植物繁殖材料的组合物可供使用。
种子处理包括本领域中已知的所有适合的种子处理技术,如种子包衣、种子涂覆、种子撒粉、浸种以及种子造粒。可以通过任何已知的方法进行具有式(I)的化合物的种子处理施用,如在种子播种之前或播种/种植过程中对种子进行喷雾或通过撒粉。
生物实例
实例B1:对烟粉虱(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洒。在干燥之后将叶圆片用成年粉虱进行侵染。孵育6天之后,针对死亡率对所述样品进行检查。
以下化合物在200ppm施用比率下产生至少80%的死亡率:
P3、P4、P6、P8、P10、P13、P14和P15。
实例B2:对黄瓜条叶活性甲(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洒用从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施用率下给出了两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:
P3、P4、P5、P7、P8、P10、P11、P12、P13、P14、和P16。
实例B3:对英雄美洲蝽(Euschistus heros)(新热带褐臭蝽)的活性
将24孔微量滴定板中的琼脂上的大豆叶片用从10’000ppm DMSO储备溶液制备的水性测试溶液进行喷洒。在干燥之后,用N2期若虫对叶片进行侵染。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施用率下给出了两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:
P3、P4、P8、P9、P10、P13、P14和P15。
实例B4:对桃蚜(绿色桃蚜虫)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10’000ppm DMSO储备溶液制备的水性测试溶液进行喷洒。干燥之后,用混合年龄的蚜虫种群对叶圆片进行侵染。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施用比率下产生至少80%的死亡率:
P3、P4、P5、P6、P7、P8、P9、P10、P11、P12、P13、P14、P15、P16、和P17。
实例B5:对桃蚜(绿色桃蚜虫)的活性。
将受到混合年龄的蚜虫种群侵染的豌豆幼苗的根部直接放在从10'000DMSO储备溶液制备的水性测试溶液中。将幼苗放置在测试溶液中6天之后,针对死亡率对所述样品进行评估。
以下化合物在24ppm测试比率下产生至少80%的死亡率:
P3、P4、P5、P6、P7、P8、P9、P10、P11、P12、P13、P14、P15、P16、和P17。
实例B6:对小菜蛾(Plutellaxylostella)(小菜蛾(Diamond back moth))的活性
将具有人工饲料的24孔微量滴定板用从10’000ppm DMSO储备溶液制备的水性测试溶液通过移液进行处理。在干燥之后,用L2期幼虫对板进行侵染(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施用率下给出了两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:
P3、P4、P5、P6、P7、P8、P11、P12、P14、和P15。
实例B7:对海灰翅夜蛾(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且用从10’000ppm DMSO储备溶液制备的水性测试溶液进行喷洒。在干燥之后,将叶圆片用五只L1期幼虫进行侵染。侵染3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。当这些类别(死亡率、拒食效果和生长抑制)中的至少一个高于未处理的样品时,实现测试样品对海灰翅夜蛾的控制。
以下化合物在200ppm施用率下产生至少80%的控制:
P3、P4、P5、P7、P8、P11、P12、P14、P15、和P16。
实例B8:对褐飞虱(Nilaparvatalugens)(褐稻飞虱(Brown plant hopper))的活性
用稀释的测试溶液在喷洒室中对水稻植物进行处理。在干燥之后,用约20只N3期若虫对植物进行侵染。处理后7天,针对死亡率和生长调节对样品进行评估。
P6、P10、P11、P12、P13、和P15
实例B9:对褐飞虱(Nilaparvatalugens)(褐稻飞虱(Brown plant hopper))的活性
将在营养液中培养的稻植物用经稀释的测试溶液处理成营养培养系统。在施用1天之后,用约20只N3期若虫对植物进行侵染。在侵染7天之后,针对死亡率和生长调节对样品进行评估。
P6、P10、P11、P12、P13、和P15
实例B10:对二斑叶螨(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10’000ppm DMSO储备溶液制备的水性测试溶液进行喷洒。干燥之后,将叶圆片用混合年龄的螨种群进行侵染。在侵染之后8天后,针对混合种群(活动阶段)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:
P3.
实例B11:对小菜蛾(Plutellaxylostella)(小菜蛾(Diamond back moth))的活性
将具有人工饲料的24孔微量滴定板用从10’000ppm DMSO储备溶液制备的水性测试溶液通过移液进行处理。在干燥之后,将菜蛾属卵吸移穿过塑料模板到凝胶印迹纸上并且用其封闭板。侵染8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施用率下给出了两个类别(死亡率或生长抑制)中至少一个的至少80%的效果:
P16、P17、P18、和P19。
实例B12:对甜菜胞囊线虫(Heterodera schachtii)的活性96孔板中的幼虫迁移率体外特性
用TECAN机器人从10'000ppm DMSO储备溶液制备测试溶液,以获得20μL的500ppm、100ppm、50ppm、25ppm、12.5ppm和6.25ppm。对于每个浓度生产三个复制品。向每个孔中加入80μL含有100至150个新收获的甜菜胞囊线虫第二阶段幼虫的线虫溶液。将板盖上并在室温下在黑暗中储存并孵育48小时。使用成像工具测量经处理的孔中暴露的幼体的迁移率,并与12个未处理复制品的平均值进行比较。
以下化合物在100ppm下48h后实现至少60%的控制:
P10、P15。
Claims (20)
1.一种具有式(I)的化合物
其中
A是CH或N
R1是C1-C4烷基
R2是氢、氰基、-C(O)R7、-C(O)OR8、C1-C6烷基或-CONR9R10、SO2R11
其中
R7是氢、C1-C6烷基或C1-C6卤代烷基,且R8是C1-C6烷基或C1-C6卤代烷基;
R9、R10彼此独立地是氢或C1-C6烷基;
R11是C1-C6烷基;
R3是氢、C1-C3烷基、C1-C3卤代烷基、氰基、-CO2H、-CO2NH2、C1-C4烷氧基羰基、C1-C4烷基氨基羰基、C1-C4二烷基氨基羰基
n是0或1;
Q是选自由以下组成的组的基团:式Q1、Q2、Q3、Q4和Q5
其中箭头指示与掺入了基团A的环的附接点;
并且其中
R4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;
X1是O或NR5;
R5是C1-C4烷基;
R6是C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、或C3-C6环烷基;
G1和G2彼此独立地是N或CH;
或具有式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、互变异构体或N-氧化物。
2.根据权利要求1所述的化合物,其中:
A是CH或N;
R1是乙基、丙基或异丙基;
R2是氢、氰基、C1-C3烷基、C1-C3烷基羰基、C1-C3烷氧基羰基、C1-C3卤代烷基羰基;
R3是氢、C1-C3卤代烷基、氰基、-CO2H、-CO2NH2、C1-C4二烷基氨基羰基;并且
n是1。
3.根据权利要求1所述的化合物,其中:
A是CH或N;
R1是乙基;
R2是氢;
R3是氢、C1-C2卤代烷基、氰基、-CO2NH2、C1-C2二烷基氨基羰基;并且
n是1。
4.根据权利要求1所述的化合物,其中:
A是CH或N;
R1是乙基;
R2是氢;
R3是氢、氰基或CO2NH2;并且
n是1。
5.根据权利要求1所述的化合物,其中:
A是CH或N;
R1是乙基;
R2是氢;
R3是氢或氰基;并且
n是1。
10.根据权利要求1所述的化合物,其中:
A是CH或N;
R1是乙基、丙基或异丙基;
R2是氢、氰基、C1-C3烷基、C1-C3烷基羰基、C1-C3烷氧基羰基、C1-C3卤代烷基羰基;
R3是氢、C1-C3卤代烷基、氰基、CO2H、CO2NH2、C1-C4二烷基氨基羰基;
n是1;
Q是选自Q1、Q2、Q4和Q5的基团
其中箭头指示与掺入了基团A的环的附接点;
并且其中
R4是C1-C2卤代烷基、C1-C2卤代烷基硫烷基、C1-C2卤代烷基亚磺酰基或C1-C2卤代烷基磺酰基;
X1是氧或NCH3;
R6是C1-C2烷基、C1-C2卤代烷基、C1-C2烷氧基或环丙基;并且
G1和G2彼此独立地是N或CH。
17.根据权利要求1所述的具有式(I)的化合物,其选自由以下组成的组:
1-[5-(乙基磺酰亚胺基)-6-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]-3-吡啶基]环丙烷甲酰胺(化合物P1);
1-[3-(乙基磺酰亚胺基)-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶-2-基]苯基]环丙烷甲酰胺(化合物P2);
[5-环丙基-2-[3-甲基-6-(三氟甲基磺酰基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]-乙基-亚氨基-氧代-λ6-硫烷(化合物P3);
[5-环丙基-2-[3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]-乙基-亚氨基-氧代-λ6-硫烷(化合物P4);
[5-环丙基-2-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]-乙基-亚氨基-氧代-λ6-硫烷(化合物P5);
1-[5-(乙基磺酰亚胺基)-6-[3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶-2-基]-3-吡啶基]环丙烷甲腈(化合物P6);
[5-环丙基-2-[6-(三氟甲基)吡唑并[4,3-c]吡啶-2-基]-3-吡啶基]-乙基-亚氨基-氧代-λ6-硫烷(化合物P7);
1-[5-(乙基磺酰亚胺基)-6-[5-甲氧基-3-甲基-4-氧代-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-3-吡啶基]环丙烷甲腈(化合物P8);
1-[3-(乙基磺酰亚胺基)-4-[3-甲基-6-(三氟甲基硫烷基)咪唑并[4,5-c]吡啶-2-基]苯基]环丙烷甲腈(化合物P9);
1-[5-(乙基磺酰亚胺基)-6-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]-3-吡啶基]环丙烷甲腈(化合物P10);
[5-环丙基-2-[7-甲基-3-(三氟甲基)咪唑并[4,5-c]哒嗪-6-基]-3-吡啶基]-乙基-亚氨基-氧代-λ6-硫烷(化合物P11);
[5-环丙基-2-[3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶-2-基]-3-吡啶基]-乙基-亚氨基-氧代-λ6-硫烷(化合物P12);
1-[3-(乙基磺酰亚胺基)-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]苯基]环丙烷甲腈(化合物P13);
1-[6-[5-乙基-3-甲基-4-氧代-6-(三氟甲基)咪唑并[4,5-c]吡啶-2-基]-5-(乙基磺酰亚胺基)-3-吡啶基]环丙烷甲腈(化合物P14);
1-[3-(乙基磺酰亚胺基)-4-[3-甲基-6-(三氟甲基)咪唑并[4,5-b]吡啶-2-基]苯基]环丙烷甲腈(化合物P15);
[5-环丙基-2-[7-(三氟甲基)咪唑并[1,2-b]哒嗪-2-基]-3-吡啶基]-乙基-亚氨基-氧代-λ6-硫烷(化合物P16);
1-[5-(乙基磺酰亚胺基)-6-[6-(三氟甲基)吡唑并[4,3-c]吡啶-2-基]-3-吡啶基]环丙烷甲腈(化合物P17);
[5-环丙基-2-[5-(三氟甲基硫烷基)-1,3-苯并噁唑-2-基]-3-吡啶基]-乙基-亚氨基-氧代-λ6-硫烷(化合物P18);以及
[5-环丙基-2-[5-(三氟甲基磺酰基)-1,3-苯并噁唑-2-基]-3-吡啶基]-乙基-亚氨基-氧代-λ6-硫烷(化合物P19)。
18.一种组合物,其包含杀昆虫、杀螨、杀线虫、或杀软体动物有效量的如权利要求1-17中任一项所定义的具有式(I)的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,以及任选地,助剂或稀释剂。
19.一种对抗并控制昆虫、螨、线虫或软体动物的方法,所述方法包括向有害生物、有害生物的场所、或易受有害生物攻击的植物施用杀昆虫、杀螨、杀线虫或杀软体动物有效量的如权利要求1-17中任一项所定义的具有式(I)的化合物,或其农用化学上可接受的盐、立体异构体、对映异构体、互变异构体或N-氧化物,或如权利要求18所定义的组合物。
20.一种用于保护植物繁殖材料免受昆虫、螨、线虫或软体动物攻击的方法,所述方法包括用根据权利要求17所述的组合物处理所述繁殖材料或所述繁殖材料所种植的场所。
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WO2022013417A1 (en) | 2020-07-17 | 2022-01-20 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
WO2022017975A1 (en) | 2020-07-18 | 2022-01-27 | Syngenta Crop Protection Ag | Pesticidally active heterocyclic derivatives with sulfur containing substituents |
CN115996921A (zh) | 2020-08-26 | 2023-04-21 | 先正达农作物保护股份公司 | 具有含硫取代基的2,2-二氟-1,3-苯并间二氧杂环戊烯衍生物的制备方法 |
CN116234811A (zh) | 2020-09-02 | 2023-06-06 | 先正达农作物保护股份公司 | 具有含硫取代基的杀有害生物活性的杂环衍生物 |
TW202229238A (zh) * | 2020-10-09 | 2022-08-01 | 瑞士商先正達農作物保護公司 | 用於製備5-(1-氰基環丙基)-吡啶-2-甲酸、酯、醯胺和腈之方法 |
BR112023025278A2 (pt) | 2021-06-02 | 2024-02-27 | Syngenta Crop Protection Ag | Derivados heterocíclicos com substituintes contendo sulfoximina ativos em termos pesticidas |
WO2023194496A1 (en) * | 2022-04-07 | 2023-10-12 | Syngenta Crop Protection Ag | Process for the preparation of diversely substituted cyanocyclopropyl - heteroarenes or arenes |
WO2024121335A1 (en) | 2022-12-07 | 2024-06-13 | Syngenta Crop Protection Ag | Synthesis of sulfoximine compounds having a stereogenic sulfur atom |
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MA52751A (fr) | 2021-04-14 |
CA3102190A1 (en) | 2019-12-12 |
UA127662C2 (uk) | 2023-11-22 |
BR112020024791A2 (pt) | 2021-03-02 |
EP3802542A1 (en) | 2021-04-14 |
CN112262140B (zh) | 2024-05-28 |
EP4342297A2 (en) | 2024-03-27 |
CO2020015278A2 (es) | 2020-12-21 |
US20230150944A1 (en) | 2023-05-18 |
KR20210018868A (ko) | 2021-02-18 |
MX2020013188A (es) | 2021-02-26 |
JP2021527065A (ja) | 2021-10-11 |
WO2019234158A1 (en) | 2019-12-12 |
EP4342297A3 (en) | 2024-05-15 |
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