CN113574053A - 杀有害生物活性的唑-酰胺化合物 - Google Patents
杀有害生物活性的唑-酰胺化合物 Download PDFInfo
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- CN113574053A CN113574053A CN202080014859.1A CN202080014859A CN113574053A CN 113574053 A CN113574053 A CN 113574053A CN 202080014859 A CN202080014859 A CN 202080014859A CN 113574053 A CN113574053 A CN 113574053A
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/02—Acaricides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/04—Insecticides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Abstract
具有式(I)的化合物,其中取代基如权利要求1中所定义,以及那些化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N‑氧化物可以用作杀昆虫剂。
Description
本发明涉及杀有害生物活性(特别是杀昆虫活性)的唑-酰胺化合物、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。
WO 2017192385描述了用于控制动物(如哺乳动物和非哺乳动物)体外寄生虫的某些杂芳基-1,2,4-三唑和杂芳基-四唑化合物。
现在已经发现了新颖的杀有害生物活性的唑吖嗪化合物。
因此,本发明在第一方面涉及具有式I的化合物
其中:
A1是N或CH;
R1是氢、C1-C6烷基、C1-C6氰基烷基、氨基羰基C1-C6烷基、羟基羰基C1-C6烷基、C1-C6硝基烷基、三甲基硅烷C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基;C3-C4环烷基C1-C2烷基-,其中所述C3-C4环烷基任选地被1或2个卤素原子取代;氧杂环丁烷-3-基-CH2-;或任选地被卤素或C1-C6卤代烷基取代的苄基;
R2是苯基、吡啶、嘧啶、吡嗪或哒嗪,其中所述苯基、吡啶、嘧啶、吡嗪或哒嗪任选地被一至三个取代基取代,其前提是所述一个或多个取代基不在与C=O附接的碳相邻的任一碳上,并且各取代基独立地选自:C1-C3烷基、C1-C3卤代烷基、C1-C3硫代卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、NO2、SF5、CN、CONH2、COOH和C(S)NH2;
R3是C1-C3烷基或C1-C3卤代烷基;
R4是C1-C6卤代烷基;C2-C6卤代烯基、C2-C6卤代炔基、C3-C4卤代环烷基、C3-C6环烷基C1-C4卤代烷基;
R5是H、C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基、C1-C3烷氧基、C1-C3烷氧基羰基、或二(C1-C3烷氧基)次甲基;或该具有式I的化合物的立体异构体、对映异构体、互变异构体和N-氧化物,或其农用化学上可接受的盐。
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(如矿物酸,例如高氯酸、硫酸、硝酸、亚硝酸、磷酸或氢卤酸),强有机羧酸(如未取代的或例如被卤素取代的C1-C4链烷羧酸,例如乙酸,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,如羟基羧酸,例如抗坏血酸、乳酸、苹果酸、酒石酸或柠檬酸,或如苯甲酸),或有机磺酸(如未取代的或例如被卤素取代的C1-C4链烷磺酸或芳基磺酸,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,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(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。
在每种情况下,根据本发明的具有式I的化合物是处于游离形式、被氧化的形式如N-氧化物、或盐的形式(例如农艺学上可用的盐的形式)。
N-氧化物是叔胺的氧化形式或含氮杂芳香族化合物的氧化形式。例如在A.Albini和S.Pietra的书“Heterocyclic N-oxides[杂环N-氧化物]”,CRC Press[CRC出版社],BocaRaton[波卡拉顿]1991中描述了它们。
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。
如本文使用的术语“C1-Cn烷基”是指具有1至n个碳原子的通过任何碳原子附接的饱和直链或支链烃基,例如甲基、乙基、正丙基、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-甲基丙基中的任何一个基团。
如本文使用的术语“C1-Cn卤代烷基”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直链或支链饱和烷基(如上所述),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-溴丁基或九氟丁基。相应地,术语“C1-C2氟烷基”将是指带有1、2、3、4或5个氟原子的C1-C2烷基,例如以下中的任一种:二氟甲基、三氟甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、1,1,2,2-四氟乙基或五氟乙基。
如本文使用的术语“C1-Cn烷氧基”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),其通过氧原子附接,即例如甲氧基、乙氧基、正丙氧基、1-甲基乙氧基、正丁氧基、1-甲基丙氧基、2-甲基丙氧基或1,1-二甲基乙氧基中的任何一种。如本文使用的术语“卤代C1-Cn烷氧基”是指C1-Cn烷氧基,其中烷基上的一个或多个氢原子被相同或不同的卤素原子替代-实例包括三氟甲氧基、2-氟乙氧基、3-氟丙氧基、3,3,3-三氟丙氧基,4-氯丁氧基。
如本文使用的术语“C1-Cn氰基烷基”是指具有1至n个碳原子的直链或支链饱和C1-Cn烷基(如上所述),其中这些基团中的氢原子之一被氰基替代:例如,氰基甲基、2-氰基乙基、2-氰基丙基、3-氰基丙基、1-(氰基甲基)-2-乙基、1-(甲基)-2-氰基乙基、4-氰基丁基等。
如本文所用,术语“C3-Cn环烷基”是指3至n元环烷基,如环丙烷、环丁烷、环戊烷和环己烷。
如本文使用的术语“C3-C4环烷基-C1-C2烷基-”是指具有亚甲基或亚乙基的3或4元环烷基,该亚甲基或亚乙基与分子的其余部分连接。在这种情况下,C3-C4环烷基-C1-C2烷基-基团经取代,该一个或多个取代基在环烷基上。
如本文使用的术语“氨基羰基C1-Cn烷基”是指烷基,其中基团中的氢原子之一被CONH2基团替代。
如本文使用的术语“羟基羰基C1-Cn烷基”是指烷基,其中基团中的氢原子之一被COOH基团替代。
如本文使用的术语“C1-Cn硝基烷基”是指烷基,其中基团中的氢原子之一被NO2基团替代。
如本文使用的术语“C1-Cn卤代烷硫基”是指通过硫原子连接的C1-C3卤代烷基部分。
如本文使用的术语“三甲基硅烷C1-Cn烷基”是指烷基,其中基团中的氢原子之一被-Si(CH3)3基团替代。
如本文所用,术语“C2-Cn烯基”是指具有从两个至n个碳原子和一个或两个双键的直链或支链烯基链,例如乙烯基、丙-1-烯基、丁-2-烯基。
如本文使用的术语“C2-Cn卤代烯基”是指被一个或多个可以相同或不同的卤素原子取代的C2-Cn烯基部分。
如本文使用的术语“C2-Cn炔基”是指具有从两个至n个碳原子和一个三键的直链或支链炔基链,例如乙炔基、丙-2-炔基、丁-3-炔基,
如本文使用的术语“C2-Cn卤代炔基”是指被一个或多个可以相同或不同的卤素原子取代的C2-Cn炔基部分。
卤素通常是氟、氯、溴或碘。这也相应地适用于与其他含义组合的卤素,如卤代烷基
R2和R4的吡啶、嘧啶、吡嗪和哒嗪基团(未取代的或取代的)各自通过各环上的碳原子与化合物的其余部分连接。
如本文使用的,术语“控制”是指减少有害生物的数量、消除有害生物和/或预防进一步的有害生物损害,这样使得减少对植物或对植物衍生产物的损害。
如本文使用的交错线(例如在K1和J1中)表示与化合物其余部分的连接/附接点。
如本文使用的,术语“有害生物”是指在农业、园艺、林业、植物源产物(如果实、谷物和木材)的储存中发现的昆虫和软体动物;以及那些与人造结构的损害有关的有害生物。术语有害生物涵盖了该有害生物生命周期的所有阶段。
如本文使用的,术语“有效量”是指化合物或其盐的量,该量在单次或多次施用时提供了希望的效果。
有效量由本领域技术人员通过使用已知技术和通过观察在类似情况下获得的结果来容易地确定。在确定有效量时,考虑了许多因素,包括但不限于:要施用的植物或衍生产物的类型;要控制的有害生物及其生命周期;所施用的特定化合物;施用类型;和其他相关情况。
如本领域的普通技术人员将理解,具有式I的化合物含有立体中心,该立体中心在以下结构中用星号指示:
其中R1、R2、R3、R4和A1是如第一方面中所定义。
本发明考虑了外消旋体和单独的对映异构体两者。具有优选立体化学的化合物在下面列出。
本发明的特别优选的化合物是具有式I’a的化合物:
其中R1、R2、R3、R4和A1是如第一方面中所定义的,和具有式(I’a)的化合物的立体异构体、对映异构体、互变异构体和N-氧化物,及其农用化学上可接受的盐。
如本文所用,术语“任选地取代的”意指所提及的基团是未取代的或者被指定取代基取代,例如“C3-C4环烷基任选地被1或2个卤原子取代”意指C3-C4环烷基、被1个卤原子取代的C3-C4环烷基和被2个卤原子取代的C3-C4环烷基。
提供了根据本发明的实施例,如下面列出的。
在本发明的每个方面的实施例中,A1是
A.A1是N;或者
B.A1是CH。
在本发明的每个方面的实施例中,R1是
A.氢;任选地被一个取代基取代的C1-C6烷基,该取代基选自:CN、CONH2、COOH、NO2和-Si(CH3)3;C1-C6卤代烷基;C2-C6烯基;C2-C6炔基;C2-C6卤代炔基;C3-C4环烷基-C1-C2烷基-,其中该C3-C4环烷基-任选地被1或2个卤素原子取代;氧杂环丁烷-3-基-CH2-;或任选地被卤素或C1-C3卤代烷基取代的苄基;或者
B.氢;C1-C6卤代烷基;任选地被CN或Si(CH3)3取代的C1-C6烷基;C3-C6炔基;C3-C4环烷基-C1-C2烷基,其中该C3-C4环烷基任选地被1或2个卤素原子取代;氧杂环丁烷-3-基-CH2-;或任选地被卤素取代的苄基;或者
C.氢、C1-C6烷基、C3-C4环烷基C1-C2烷基-(其中该C3-C4环烷基任选地被1或2个卤素原子取代)、或氧杂环丁烷-3-基-CH2-;或者
D.氢、C1-C6烷基、或C3-C4环烷基C1-C2烷基-;或者
E.氢;C1-C6卤代烷基;任选地被CN或Si(CH3)3取代的C1-C6烷基;C3-C6炔基;或C3-C4环烷基-C1-C2烷基,其中该C3-C4环烷基任选地被1或2个卤素原子取代;或者
F.氢;C1-C6卤代烷基;C1-C6烷基;C3-C6炔基;或C3-C4环烷基-C1-C2烷基,其中该C3-C4环烷基任选地被1或2个卤素原子取代;或者
G.环丙基-CH2-、正丙基、CH≡CCH2-、CF3CH2CH2-、FCH2CH2-、FCH2CH2CH2-、2,2-二氟环丙基-CH2-、2,2-二氯环丙基-CH2-、氢、CH3、(CH3)3SiCH2-、CH3CH2-、或CNCH2-;或者
H.环丙基-CH2-、正丙基、CH≡CCH2-、CF3CH2CH2-、FCH2CH2-、FCH2CH2CH2-、2,2-二氟环丙基-CH2-或2,2-二氯环丙基-CH2-;或者
I.环丙基-CH2-、正丙基、CH≡CCH2-、CF3CH2CH2-、FCH2CH2-、FCH2CH2CH2-、2,2-二氟环丙基-CH2-、氢、CH3、(CH3)3SiCH2-、或CH3CH2-;或者
J.环丙基-CH2-、正丙基、CH≡CCH2-、CF3CH2CH2-、FCH2CH2-、FCH2CH2CH2-、或2,2-二氟环丙基-CH2-;或者
K.环丙基-CH2-、正丙基、CH≡CCH2-、CF3CH2CH2-、FCH2CH2-、或FCH2CH2CH2-;或者
L.环丙基-CH2-、CH≡CCH2-、氢或CH3;或者
M.CH≡CCH2-或环丙基-CH2-;或者
N.环丙基-CH2-;或者
O.环丙基-CH2-、氢或CH3;或者
P.氢。
在本发明的每个方面的实施例中,R2是
A.苯基、吡啶、嘧啶、吡嗪或哒嗪,其中该苯基、吡啶、嘧啶、吡嗪或哒嗪任选地被一至三个取代基取代,其前提是该一个或多个取代基不在与-C(O)-基团键合的碳毗邻的任一碳上,该一至三个取代基各自独立地选自:C1-C3烷基、C1-C3卤代烷基、C1-C3硫代卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤基、NO2、SF5、CN、CONH2、COOH和C(S)NH2;或者
B.苯基、吡啶、嘧啶、吡嗪或哒嗪,其中该苯基、吡啶、嘧啶、吡嗪或哒嗪任选地被一至两个取代基取代,其前提是该一个或多个取代基不在与C=O附接的碳毗邻的任一碳上,并且取代基各自独立地选自:C1-C3烷基、C1-C3卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素或CN;或者
C.被一个或两个取代基取代的苯基、3-吡啶或4-吡啶,该一个或两个取代基独立地选自:C1-C3卤代烷基、C1-C3卤代烷氧基、卤素、CN或C(S)NH2,其前提是该一个或多个取代基不在与-C(O)-基团键合的碳毗邻的任一碳上;或者
D.被一个或两个取代基取代的苯基、3-吡啶或4-吡啶,该一个或两个取代基独立地选自:C1-C3卤代烷基、C1-C3卤代烷氧基、卤素、或CN,其前提是该一个或多个取代基不在与-C(O)-基团键合的碳毗邻的任一碳上;或者
E.被一个或两个取代基取代的苯基或3-吡啶,该一个或两个取代基独立地选自:C1-C3卤代烷基、C1-C3卤代烷氧基、卤素、或CN,其前提是该一个或多个取代基不在与-C(O)-基团键合的碳毗邻的任一碳上;或者
F.3,5-双(三氟甲基)苯基、3,5-二氯苯基、3-三氟甲氧基苯基、3-氯-5-三氟甲基苯基、3-氰基苯基、3-氯-5-三氟甲氧基苯基、5-三氟甲基吡啶-3-基、3-溴-5-三氟甲基苯基、3-氰基-5-三氟甲基苯基或2,6-双(三氟甲基)吡啶-4-基;或者
G.3,5-双(三氟甲基)苯基、3,5-二氯苯基、3-三氟甲氧基苯基、3-氯-5-三氟甲基苯基、3-氰基苯基、3-氯-5-三氟甲氧基苯基、5-三氟甲基吡啶-3-基、3-溴-5-三氟甲基苯基或3-氰基-5-三氟甲基-苯基;或者
H.3,5-双(三氟甲基)苯基、3,5-二氯苯基、3-三氟甲氧基苯基、3-氯-5-三氟甲基苯基、3-氰基苯基、3-氯-5-三氟甲氧基苯基或5-三氟甲基吡啶-3-基;或者
I.是3,5-双(三氟甲基)苯基、3-氯-5-三氟甲基苯基、3-氰基苯基-3-氯-5-三氟甲氧基苯基、5-三氟甲基吡啶-3-基或3-氰基-5-三氟甲基苯基;或者
J.3,5-双(三氟甲基)苯基、3-氯-5-三氟甲基苯基、3-氯-5-三氟甲氧基苯基或5-三氟甲基吡啶-3-基;或者
K.3,5-双(三氟甲基)苯基;或者
L.K1至K21中之一;或者
M.K1、K2、K3、K5、K6、K7、K11、K13或K15中之一;或者
N.K1、K2、K5、K6、K7、K11、K13或K15;或者
O.K1、K3、K5、K6、K11、K13或K15中之一;或者
P.K1、K5、K6、K11、K13或K15中之一;或者
Q.K1、K3、或K11中之一;或者
R.K1、或K11中之一;或者
S.K1、K5、K6、K11、K12、K13、K15、K16、K18、K19、K20、或K21中之一;或者
T.K1、K5、K6、K11、K13、K15、K19、或K20中之一;或者
U.K1、K6、K11、K15、K19、或K20中之一;或者
V.K1、K15、或K20中之一;或者
W.K1。
在本发明的每个方面的实施例中,R3是
A.C1-C3烷基或C1-C3卤代烷基;或者
B.C1-C3烷基;或者
C.甲基。
在本发明的每个方面的实施例中,R4是
A.C1-C6卤代烷基;C2-C6卤代烯基、或C2-C6卤代炔基、或C3-C4卤代环烷基;或者
B.C1-C4卤代烷基;C2-C4卤代烯基、或C2-C4卤代炔基;或者
C.C1-C4氟烷基;C2-C4氟烯基、或C2-C4氟炔基;或者
D.三氟甲氧基、二氟甲氧基、2,2,2-三氟乙氧基、2,2-二氟乙氧基、或3,3,3-三氟丙-1-烯氧基;或者
E.三氟甲氧基或二氟甲氧基;或者
F.三氟甲氧基。
在实施例中,含有R4取代基的环基团选自J1至J10。
优选地,该环基团选自J1至J4;更优选地,J1或J2。
在本发明的每个方面的实施例中,R5是
A.氢、卤素、CN、C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基、C1-C3烷氧基、或C1-C3卤代烷氧基;或者
B.氢、卤素、C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基、C1-C3烷氧基、或C1-C3卤代烷氧基;或者
C.氢、C1-C3烷基、C1-C3卤代烷基、C1-C3卤代烷氧基、C1-C3烷氧基、或C3-C4环烷基;或者
D.氢、C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基;或者
E.氢、卤素、C1-C3卤代烷基、或C1-C3烷氧基;或者
F.氢、C1-C3卤代烷基、或C1-C3烷氧基;或者
G.C1-C3卤代烷基、或C1-C3烷氧基;或者
H.氢、甲基、CH2CF3、或环丙基;或者
I.甲基、CH2CF3、或环丙基;或者
J.氢、甲基或(CH2CH2O)2CH-;或者
K.甲基或(CH2CH2O)2CH-;或者
L.氢或甲基;或者
M.氢;或者
N.甲基。
因此,本发明提供了具有如上定义的以所有组合/每个排列的取代基R1、R2、R3、R4、R5、以及A1的具有式I的化合物。因此,可获得例如具有式I的化合物,其中A1为第一方面(即A1是N或CH);R1是实施例D(即氢、C1-C6烷基、或C3-C4环烷基C1-C2烷基-);R2是实施例H(即,3,5-双(三氟甲基)苯基、3,5-二氯苯基、3-三氟甲氧基苯基、3-氯-5-三氟甲基苯基、3-氰基苯基、3-氯-5-三氟甲氧基苯基或5-三氟甲基吡啶-3-基);R3是实施例C(即,甲基);并且R4是实施例B(即C1-C4卤代烷基;C2-C4卤代烯基、或C2-C4卤代炔基);并且R5是实施例L(即氢或甲基)。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、C1-C6烷基、C3-C4环烷基C1-C2烷基;作为R2的K1、K5、K6、K11、K12、K13、K15、K16、K18、K19、K20、或K21中之一;作为R3的甲基;作为R5的氢、C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基;以及作为A1是N或CH;以及作为R4的C1-C4卤代烷基;C2-C4卤代烯基、或C2-C4卤代炔基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、甲基、环丙基CH2;作为R2的K1、K5、K6、K11、K12、K13、K15、K16、K18、K19、K20、或K21中之一;作为R3的甲基;作为R5的氢、C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基;以及作为A1是N或CH;以及作为R4的C1-C4卤代烷基;C2-C4卤代烯基、或C2-C4卤代炔基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、甲基、或环丙基CH2;作为R2的K1、K5、K6、K11、K12、K13、K15、K16、K18、K19、K20、或K21中之一;作为R3的甲基;作为R5的氢、甲基、CH2CF3、或环丙基;以及作为A1是N或CH;以及作为R4的C1-C4卤代烷基;C2-C4卤代烯基、或C2-C4卤代炔基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、甲基、或环丙基CH2;作为R2的K1、K5、K6、K11、K13、K15、K19、或K20中之一;作为R3的甲基;作为R5的氢、甲基、CH2CF3、或环丙基;以及作为A1是N或CH;以及作为R4的C1-C4卤代烷基;C2-C4卤代烯基、或C2-C4卤代炔基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、甲基、或环丙基CH2;作为R2的K1、K6、K11、K15、K19、或K20中之一;作为R3的甲基;作为R5的氢、甲基、CH2CF3、或环丙基;以及作为A1是N或CH;以及作为R4的C1-C4卤代烷基;C2-C4卤代烯基、或C2-C4卤代炔基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、甲基、或环丙基CH2;作为R2的K1、K15、或K20中之一;作为R3的甲基;作为R5的氢、甲基、CH2CF3、或环丙基;以及作为A1是N或CH;以及作为R4的C1-C4卤代烷基;C2-C4卤代烯基、或C2-C4卤代炔基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、甲基、或环丙基CH2;作为R2的K1、K6、K11、K15、K19、或K20中之一;作为R3的甲基;作为R5的氢、甲基、CH2CF3、或环丙基;以及作为A1是N或CH;以及作为R4的三氟甲氧基、二氟甲氧基、2,2,2-三氟乙氧基、2,2-二氟乙氧基、或3,3,3-三氟丙-1-烯氧基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、甲基、或环丙基CH2;作为R2的K1、K15、或K20中之一;作为R3的甲基;作为R5的氢、甲基、CH2CF3、或环丙基;以及作为A1是N或CH;以及作为R4的三氟甲氧基、二氟甲氧基、2,2,2-三氟乙氧基、2,2-二氟乙氧基、或3,3,3-三氟丙-1-烯氧基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、C1-C6烷基、C3-C4环烷基C1-C2烷基;作为R2的K1、K2、K5、K6、K7、K11、K12、K13、K15、K16、K18、K19、K20、或K21中之一;作为R3的甲基;作为R5的氢、C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基;以及作为A1是N或CH;以及作为R4的C1-C4卤代烷基、C2-C4卤代烯基、或C2-C4卤代炔基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、C1-C6烷基、C3-C4环烷基C1-C2烷基;作为R2的K1、K5、K6、K11、K12、K13、K15、K16、K18、K19、K20、或K21中之一;作为R3的甲基;作为R5的氢、C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基;以及作为A1是N或CH;以及作为R4的C1-C4卤代烷基、C2-C4卤代烯基、或C2-C4卤代炔基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、C1-C6烷基、C3-C4环烷基C1-C2烷基;作为R2的K1、K5、K6、K11、K12、K13、K15、K16、K18、K19、K20、或K21中之一;作为R3的甲基;作为R5的氢、C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基;以及作为A1是N或CH;以及作为R4的C2-C4卤代烯基、或C2-C4卤代炔基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的C1-C6烷基、C3-C4环烷基C1-C2烷基;作为R2的K1、K5、K6、K11、K12、K13、K15、K16、K18、K19、K20、或K21中之一;作为R3的甲基;作为R5的氢、C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基;以及作为A1是N或CH;以及作为R4的C1-C4卤代烷基;C2-C4卤代烯基、或C2-C4卤代炔基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的甲基、或环丙基CH2;作为R2的K1、K5、K6、K11、K12、K13、K15、K16、K18、K19、K20、或K21中之一;作为R3的甲基;作为R5的氢、甲基、CH2CF3、或环丙基;以及作为A1是N或CH;以及作为R4的三氟甲氧基、二氟甲氧基、2,2,2-三氟乙氧基、2,2-二氟乙氧基、或3,3,3-三氟丙-1-烯氧基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、C1-C6烷基、C3-C4环烷基C1-C2烷基;作为R2的K1、K3、K5、K6、K11、K12、K13、K15、K16、K18、K19、K20、或K21中之一;作为R3的甲基;作为R5的C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基;以及作为A1是N或CH;以及作为R4的C1-C4卤代烷基;C2-C4卤代烯基、或C2-C4卤代炔基。
在本发明每个方面的实施例中,具有式I的化合物具有作为R1的氢、甲基、或环丙基CH2;作为R2的K1、K3、K5、K6、K11、K12、K13、K15、K16、K18、K19、K20、或K21中之一;作为R3的甲基;作为R5的甲基、CH2CF3、或环丙基;以及作为A1是N或CH;以及作为R4的三氟甲氧基、二氟甲氧基、2,2,2-三氟乙氧基、2,2-二氟乙氧基、或3,3,3-三氟丙-1-烯氧基。
在第二方面,本发明使得包含如在第一方面中所定义的具有式I的化合物、一种或多种助剂和稀释剂、以及任选地一种或多种其他活性成分的组合物可供使用。
在第三方面,本发明使得对抗和控制昆虫、螨、线虫或软体动物的方法可供使用,该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在第一方面中所定义的化合物或如在第二方面中所定义的组合物。
在第四方面,本发明使得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可供使用,该方法包括用有效量的如在第一方面中所定义的具有式I的化合物或如在第二方面中所定义的组合物处理该繁殖材料或该繁殖材料所种植的场地。
在第五方面,本发明使得植物繁殖材料(如种子)可供使用,该植物繁殖材料包含如在第一方面中所定义的具有式I的化合物或如在第二方面中所定义的组合物,或用如在第一方面中所定义的具有式I的化合物或如在第二方面中所定义的组合物进行处理,或将如在第一方面中所定义的具有式I的化合物或如在第二方面中所定义的组合物粘附到其上。
在本发明的每个方面的实施例中,具有式I的化合物具有R2如3,5-二氯苯基;R3如甲基;R1如氢;R4如选自5-(二氟甲氧基)嘧啶-2-基、5-(三氟甲氧基)嘧啶-2-基、5-(二氟甲氧基)吡啶-2-基、5-(三氟甲氧基)吡啶-2-基、5-(三氟甲氧基)吡啶-2-基、5-(2,2,2-三氟乙氧基)吡啶-2-基、5-(五氟乙氧基)吡啶-2-基、以及5-(4,4,4-三氟丁氧基)吡啶-2-基;以及R5如氢被排除在本发明之外。
在另一方面,本发明提供了控制有需要的动物体内或体表的寄生虫的方法,该方法包括给予有效量的第一方面的化合物。本发明进一步提供了控制有需要的动物的体外寄生虫的方法,该方法包括给予有效量的如在第一方面中定义的具有式I的化合物。本发明进一步提供了用于预防和/或治疗由体外寄生虫传播的疾病的方法,该方法包括对有需要的动物给予有效量的如在第一方面中所定义的具有式I的化合物。
本领域技术人员可以按照已知方法制备具有式I的化合物。更具体地,具有式I和I’a的化合物及其中间体可以如以下在方案和实例中描述的制备。为了清楚起见,某些立体中心没有指明,并且不旨在以任何方式限制这些方案的传授内容。
根据本发明的用于制备具有式I的化合物的方法通过本领域的技术人员已知的方法进行。具有式I的化合物
可以通过以下项的反应制备:具有式II的胺
其中R1、R3、R4、R5、以及A1是如式I中所描述,与具有式III的羧酸衍生物的反应制备
其中R2如上式I所述。该化学过程在方案1中更详细地描述。
方案1:
在方案1中,通过本领域技术人员已知并描述于例如Tetrahedron[四面体],61(46),10827-10852,2005中的方法将具有式III的化合物(其中R2是如式I中所描述)活化为具有式IIIa的化合物。例如其中X0是卤素的化合物是通过在催化量的DMF的存在下,在惰性溶剂如二氯甲烷或THF中,在20℃至100℃之间的温度(优选25℃)下用例如草酰氯或亚硫酰氯处理具有式III的化合物形成的。任选地在碱(例如三乙胺或吡啶)的存在下,用具有式II的化合物(其中R1、R3、R4、R5和A1如以上所定义)处理IIIa,生成具有式I的化合物。可替代地,可以通过在惰性溶剂(例如吡啶、DMF、乙腈、CH2Cl2或THF)中,任选地在碱(例如三乙胺)的存在下,在30℃-180℃之间的温度下,用二环己基碳二亚胺(DCC)、1-乙基-3-(3-二甲基氨基丙基)碳二亚胺(EDC)或1-[双(二甲基氨基)亚甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓-3-氧化物六氟磷酸盐(HATU)处理具有式III的化合物以给出被活化的物种IIIa(其中X0分别是X01、X02和X03)来制备具有式I的化合物。最后,具有式III的酸也可以通过与偶联剂(如丙烷膦酸酐())反应被活化,以提供具有式IIIa的化合物,其中X0是X04,如例如在Synthesis[合成]2013,45,1569中描述的。与具有式II的胺的进一步反应提供了具有式I的化合物。
具有式IIa的化合物(其中R1、R3、R4、R5和A1如以上所定义)可以由本领域技术人员制备。此种合成的典型实例在方案2中示出。
方案2.
例如,具有式II的化合物可以通过在合适的溶剂(可以包括例如,乙腈或二噁烷)中,在合适的碱(如碳酸钠、碳酸钾或碳酸铯(或碳酸氢钠或碳酸氢钾))的存在下,在室温与200℃之间、优选在40℃至反应混合物的沸点之间的温度加热下(任选地在微波加热条件下)具有式VI的化合物(其中R3、R4、R5和A1是如在式I中所定义的)与具有式VIII的化合物(其中R1是在式I中定义的)之间的反应来制备。
具有式VI的化合物(其中R3、R4、R5和A1如以上所定义)可通过在合适的溶剂(其可包括例如乙酸和1,4-二噁烷的混合物)中,通常在室温与200℃之间、优选40℃至反应混合物的沸点之间的温度加热(任选地在微波加热条件下)下具有式V的化合物(其中R3如式I中所定义)与具有式VII的化合物(其中R4和A1在式I中定义)之间的反应制备。此类方法先前已经描述于例如Tetrahedron[四面体]2017,73,750中。
具有式V的化合物(其中R3如以上所定义)可以通过在合适的溶剂(其可包括例如二氯甲烷)中,通常在室温与200℃之间、优选20℃至反应混合物的沸点之间的温度加热下具有式IV的化合物(其中R2如式I中定义)与N,N-二甲基甲酰胺二甲基缩醛(DMF-DMA)之间的反应制备。此类方法先前已经描述于例如Tetrahedron[四面体]2017,73,750中。
具有式IIa的化合物(其中R5如式I中所定义)可以如方案3中所示出的制备;
方案3.
如方案3中所示出的,具有式IIa的化合物可以通过在合适的溶剂(可以包括例如,乙腈或二噁烷)中,在合适的碱(如碳酸钠、碳酸钾或碳酸铯(或碳酸氢钠或碳酸氢钾))的存在下,在室温与200℃之间、优选在40℃至反应混合物的沸点之间的温度加热下(任选地在微波加热条件下)具有式VIa的化合物(其中R3、R4、R5和A1是如在式I中所定义的)与具有式VIII的化合物(其中R1是在式I中定义的)之间的反应来制备。
具有式VIa的化合物(其中R3、R4、R5和A1如以上所定义)可以通过在合适的溶剂(其可以包括例如乙酸和1,4-二噁烷的混合物)中,通常在室温与200℃之间、优选40℃至反应混合物的沸点之间的温度加热(任选地在微波加热条件下)下具有式XI的化合物(其中R3和R5如式I中所定义)与具有式VII的化合物(其中R4和A1在式I中定义)之间的反应制备。此类方法先前已经描述于例如Tetrahedron[四面体]2017,73,750中。
具有式XI的化合物(其中R3和R5如以上所定义)可以通过在合适的溶剂(其可以包括例如DMF)中,在合适的碱(例如DIPEA)存在下,在室温与200℃之间、优选20℃至反应混合物的沸点之间的温度加热下具有式IX的化合物(其中R3是如式I中所定义)与具有式X的化合物(其中R5是如式I中所定义)之间的反应制备。这种方法先前已经描述于,例如Journalof Organic Chemistry[有机化学杂志],2011,76,1177中。
具有式Ia的化合物(其中R1、R2、R3、R4和A1如以上所定义)可以进一步由本领域技术人员如方案4中所示出的制备。
方案4.
例如具有式I的化合物(其中R1、R2、R3、R4和A1是如以上所定义)可以通过在合适的溶剂(其可以包括例如乙酸和1,4-二噁烷的混合物)中,通常在室温与200℃之间、优选40℃至反应混合物的沸点之间的温度加热下(任选地在微波加热条件下)具有式XIV的化合物(其中R1、R2和R3是如以上所定义)与具有式VII的化合物(其中R4和A1如式I中所定义)之间的反应制备。此类方法先前已经描述于例如Tetrahedron[四面体]2017,73,750中。
具有式XIV的化合物(其中R1、R2和R3如以上所定义)可以通过在合适的溶剂(其可以包括例如,二氯甲烷)中,通常在室温与200℃之间、优选在40℃至反应混合物的沸点之间的温度加热下具有式XIII的化合物(其中R1、R2和R3如以上所定义)与N,N-二甲基甲酰胺二甲基缩醛(DMF-DMA)之间的反应来制备。此类方法先前已经描述于,例如Tetrahedron[四面体]2017,73,750和US2016296501,制备7,第29页中。
具有式XIII的化合物(其中R1、R2和R3如上定义)可以通过在合适的惰性溶剂(其可以包括例如吡啶、DMF、乙腈、CH2Cl2或THF),任选地在碱(例如三乙胺或吡啶)的存在下,通常在室温与200℃之间的温度加热下具有式XII的化合物(其中R1和R3如上定义)与具有式IIIa的化合物(其中R2和X0是如方案1中定义)之间的反应制备。
具有式XII的化合物(其中R1和R3如上定义)可以通过在合适的溶剂(其可以包括例如乙腈或二噁烷)中,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))存在下,通常在室温与200℃之间、优选40℃至反应混合物的沸点之间的温度加热下(任选地在微波加热条件下)具有式IV的化合物(其中R3是如式I中定义)与具有式VIII的化合物(其中R1是式I中定义)之间的反应制备。
具有式VII的肼(其中A1如以上所定义且R4如以上所定义)可商购获得或者可以根据众所周知的方法或如方案5中所示制备。因此,具有式XV的化合物(其中A1是N或CH,并且Xa1是离去基团(如Cl、Br、F、I、OSO2CF3、或OSO2CH3)可以用碱(例如碳酸铯或碳酸钾)在溶剂如乙腈或DMF中,在20℃-80℃之间的温度下,用具有式XIV的化合物烷基化(其中Xa2是离去基团如Cl、Br、F、I、OSO2CF3、或OSO2CH3),以得到具有式XIII的化合物(其中R4、A1和Xa1如先前所定义)。此类反应是本领域技术人员熟知的并且已例如报道于以下文献中:参见例如Med.Chem.Letts.[药物化学快报],2017,8(5),第543-548页和Bio.Med.Chem.Letts.[生物与药学化学快报],2017,27(11),2420-2423。具有式XIII的化合物可以在合适的溶剂例如乙醇、二噁烷水溶液中在温度20℃-80℃下用肼处理以得到具有式VII的化合物,其中R4和A1如先前所描述。类似的反应先前已在例如J.Med.Chem.[药物化学杂志],2018,61(1),207-223,以及Bio.Med.Chem.Letts.[生物与药学化学快报],2017,27(21),4858-4866中描述过。具有式XIIIa的化合物(其中R4是CHF2)可以由具有式XII的化合物通过在碱(如KOH、碳酸钾等)的存在下,在惰性溶剂中,在20℃-80℃之间的温度下,用二氟卡宾源(例如ClCF2CO2Na或CF2SO2OCHF2)处理而制备。此类程序已例如描述于以下文献中:J.Fluor.Chem.[氟化学杂志]2017,203,155,以及US2013/0225552,第128页,以及Org.Process Res.Dev.[有机过程研究与发展],2011,15,721。
方案5:
具有式I的化合物(其中R1、R2、R3、R4、以及A1如以上所定义)也可以如方案6中所示的方法制备。
方案6.
具有式I的化合物(其中R1、R2、R3、R4和A1如先前所定义)可以由具有式XX的化合物通过在碱(如氢化钠、K2CO3、或Cs2CO3)的存在下,在惰性溶剂(如THF、DMF、或乙腈)中,用具有通式XXI的烷基化试剂(其中Xa4优选地是Cl、Br、F、I、OSO2CF3、或OSO2CH3)处理而制备,以得到具有式I的化合物。此类烷基化反应是本领域技术人员众所周知的。
具有式XX的化合物也可以通过具有式XVI的化合物的宫浦(Miyura)硼酸化、随后具有式XIX的中间体的氧化而获得。具有式XIX的中间体(其中A1、R1、R2、以及R3如式I下所定义并且BL2代表硼酸衍生物,优选地4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)可以通过在钯催化的反应中用双频哪醇二硼烷(BPin)2处理具有式XVII的化合物(其中Xa1是Cl、Br、I、或OTf,并且X1、R1和R2如式I下所定义)而获得。该反应可以在质子惰性溶剂中,在作为该类型反应的常用催化剂的碱(优选弱碱如乙酸钾KOAc和Pd(dppf)Cl2)存在下进行。该反应的温度优选地在0℃和反应混合物的沸点之间。可以通过用氧化剂(优选过氧化氢或其脲络合物)处理,将获得的具有式XIX的中间体转化为具有式XX的化合物。具有式XVII的化合物也可以通过在25℃-100℃之间的温度下,在质子惰性溶剂(例如乙腈或DMF)中,在碱(例如碳酸钾或碳酸铯)的存在下,任选地在钯催化剂(例如RockPhos-G3-5氨基联苯基)]甲磺酸钯(II))的存在下与(E)-苯甲醛肟的反应而转化为具有式XX的化合物。此类反应在文献中是熟知的并且已经描述于例如Ang.Che.Int.Ed[德国应用化学国际版].56,(16)4478–4482,2017中。如此获得的具有式XX的化合物通过本领域技术人员众所周知的以及以上所描述的方法烷基化而转化为具有式I的化合物。
具有式I的化合物,特别是其中R4是CF3的那些,即具有式Ic的化合物的进一步合成描述于方案7中:
方案7
根据方案7,可以在惰性溶剂(如乙腈、光氧化还原催化剂如三(2,2′-联吡啶)六氟磷酸钌(II))中,在蓝光LED光(15W)的照射下,在以下项的存在下在室温下处理具有式XXII的化合物(如本文或WO 2017192385中所描述的制备):1-(三氟甲氧基)吡啶-4-甲腈;1,1,1-三氟-N(三氟甲基磺酰基)甲磺酰胺。此类反应已经描述于文献中(参见Ang.Chem.[德国应用化学],2018,57(42),13784-13789)。
具有式III的化合物是已知的,例如3-(二氟甲基)-5-(三氟甲基)苯甲酸
CAS:[2248290-21-1],3-溴-5-(三氟甲基)苯甲酸CAS:[328-67-6],3-碘-5-(三氟甲基)苯甲酸,CAS:[28186-62-1]可商购的,或者可以由本领域技术人员制备。例如还参见WO 2013/171712、WO2012/117000、WO 2017/192385。一些具有式III的化合物是新颖的,并且已经尤其制备以使得能够制备具有式I的化合物。此类化合物的合成示出于方案8中:
方案8
如方案8中所示,可以用二吡啶铜试剂(bpy)CuSCF3(其中bpy是二吡啶基)在惰性溶剂如乙腈或DMF中在室温与120℃之间的温度下任选地在微波加热下处理具有式XXIII的化合物(其中Z01是卤素,优选地溴或碘,A2是氮或甲烷,且Ra是C1-C4烷基)以得到具有式XXIV的化合物(其中A2和Ra如先前所定义)。此种化学过程是已知的并且已经描述于文献例如Angew.Chem.Int.Ed.[应用化学国际版]2013,52,1548-1552中。用于这种转化的优选试剂是(bpy)CuSCF3(CAS[1413732-47-4])。具有式XXIV的化合物通过酯水解转化为具有式IIIb的化合物,例如与碱(例如氢氧化锂、氢氧化钾或氢氧化钠)在水中任选地在水混溶性溶剂(如THF、丙酮、二噁烷等)的存在下的反应。此类反应是本领域技术人员熟知的。具有式XXVI的化合物(其中R6是C1-C3烷基、或C1-C3卤代烷基,并且Ra是C1-C4烷基)可以通过以下方式制备:使具有式XXV的化合物与具有式XXVII的化合物(其中Xa5是Cl、Br、F、I、OSO2CF3、或OSO2CH3)在碱(如氢化钠、K2CO3、或Cs2CO3)的存在下在惰性溶剂(如THF、DMF、或乙腈)中进行反应以得到具有式XXVI的化合物。通过用原位产生的二氟卡宾处理(类似于方案5中对于制备XVIIa所述的程序)制备具有式XXVI的化合物(其中R6是CHF2)。具有式XXVI的化合物的水解以得到具有式IIIc的化合物,如上所述。
取决于程序或反应条件,反应物可在碱存在下反应。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、二异丙基氨基锂、双(三甲基甲硅烷基)氨基钾、氢化钙、三乙胺、二异丙基乙胺、三亚乙基二胺、环己胺、N-环己基-N,N-二甲胺、N,N-二乙基苯胺、吡啶、4-(N,N-二甲基氨基)吡啶、奎宁环、N-甲基吗啉、苄基三甲基氢氧化铵以及1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)。
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,添加惰性溶剂或稀释剂或这些的混合物是有利的。如果反应在碱的存在下进行,那么过量使用的碱(如三乙胺、吡啶、N-甲基吗啉或N,N-二乙基苯胺)还可以充当溶剂或稀释剂。
反应有利地在从约-80℃至约+140℃、优选地从约-30℃至约+100℃的温度范围内,在许多情况下在环境温度与约+80℃之间的范围内进行。
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(如钠盐、钡盐或银盐,例如用乙酸银)来处理无机酸的盐(如盐酸盐),在该溶剂中,所形成的无机盐(例如氯化银)是不溶的并且因此从反应混合物中沉淀出。
取决于程序或反应条件,具有成盐特性的具有式I的化合物可以呈游离形式或呈盐形式获得。
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在此意义上理解,即使当立体化学细节未在每种情况下明确提及时。
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(它们可以取决于已选择的起始材料和程序获得)能够在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;通过形成包合化合物,例如使用手性冠醚,其中仅一种对映异构体被络合;或通过转化成非对映异构的盐,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,从这些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可以根据本发明获得,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。
如果各个组分具有不同的生物活性,有利的是在每种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。
在适当情况下,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。
根据下表A-1至A-120的具有式I的化合物可以根据上述方法制备。随后的这些实例旨在说明本发明并且展示优选的具有式I的化合物(以具有式Ia的化合物的形式)。
表A-1提供了具有式Ia的12种化合物A-1.001至A-1.012,其中R1是H,R5是H、R4a是[5-(三氟甲氧基)嘧啶-2-基]并且R2是如表Z中所定义的。例如A-1.012是
表Z:R2的取代基定义:
表A-2提供了具有式Ia的12种化合物A-2.001至A-2.012,其中R1是H,R5是H,R4a是[5-(三氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-3提供了具有式Ia的12种化合物A-3.001至A-3.012,其中R1是H,R5是H,R4a是[5-(二氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-4提供了具有式Ia的12种化合物A-4.001至A-4.012,其中R1是H,R5是H,R4a是[5-(二氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-5提供了具有式Ia的12种化合物A-5.001至A-5.012,其中R1是H,R5是H,R4a是[5-(2,2,2-三氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-6提供了具有式Ia的12种化合物A-6.001至A-6.012,其中R1是H,R5是H,R4a是[5-(2,2,2-三氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-7提供了具有式Ia的12种化合物A-7.001至A-7.012,其中R1是H,R5是H,R4a是[5-(2,2-二氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-8提供了具有式Ia的12种化合物A-8.001至A-8.012,其中R1是H,R5是H,R4a是[5-(2,2-二氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-9提供了具有式Ia的12种化合物A-9.001至A-9.012,其中R1是H,R5是H,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]嘧啶-2-基]并且R2如表Z中所定义。
表A-10提供了具有式Ia的12种化合物A-10.001至A-10.012,其中R1是H,R5是H,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]-2-吡啶基]并且R2如表Z中所定义。
表A-11提供了具有式Ia的12种化合物A-11.001至A-11.012,其中R1是H,R5是CH3,R4a是[5-(三氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-12提供了具有式Ia的12种化合物A-12.001至A-12.012,其中R1是H,R5是CH3,R4a是[5-(三氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-13提供了具有式Ia的12种化合物A-13.001至A-13.012,其中R1是H,R5是CH3,R4a是[5-(二氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-14提供了具有式Ia的12种化合物A-14.001至A-14.012,其中R1是H,R5是CH3,R4a是[5-(二氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-15提供了具有式Ia的12种化合物A-15.001至A-15.012,其中R1是H,R5是CH3,R4a是[5-(2,2,2-三氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-16提供了具有式Ia的12种化合物A-16.001至A-16.012,其中R1是H,R5是CH3,R4a是[5-(2,2,2-三氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-17提供了具有式Ia的12种化合物A-17.001至A-17.012,其中R1是H,R5是CH3,R4a是[5-(2,2-二氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-18提供了具有式Ia的12种化合物A-18.001至A-18.012,其中R1是H,R5是CH3,R4a是[5-(2,2-二氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-19提供了具有式Ia的12种化合物A-19.001至A-19.012,其中R1是H,R5是CH3,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]嘧啶-2-基]并且R2如表Z中所定义。
表A-20提供了具有式Ia的12种化合物A-20.001至A-20.012,其中R1是H,R5是CH3,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]-2-吡啶基]并且R2如表Z中所定义。
表A-21提供了具有式Ia的12种化合物A-21.001至A-21.012,其中R1是H,R5是环丙基(Cyp),R4a是[5-(三氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-22提供了具有式Ia的12种化合物A-22.001至A-22.012,其中R1是H,R5是Cyp,R4a是[5-(三氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-23提供了具有式Ia的12种化合物A-23.001至A-23.012,其中R1是H,R5是Cyp,R4a是[5-(二氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-24提供了具有式Ia的12种化合物A-24.001至A-24.012,其中R1是H,R5是Cyp,R4a是[5-(二氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-25提供了具有式Ia的12种化合物A-25.001至A-25.012,其中R1是H,R5是Cyp,R4a是[5-(2,2,2-三氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-26提供了具有式Ia的12种化合物A-26.001至A-26.012,其中R1是H,R5是Cyp,R4a是[5-(2,2,2-三氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-27提供了具有式Ia的12种化合物A-27.001至A-27.012,其中R1是H,R5是Cyp,R4a是[5-(2,2-二氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-28提供了具有式Ia的12种化合物A-28.001至A-28.012,其中R1是H,R5是Cyp,R4a是[5-(2,2-二氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-29提供了具有式Ia的12种化合物A-29.001至A-29.012,其中R1是H,R5是Cyp,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]嘧啶-2-基]并且R2如表Z中所定义。
表A-30提供了具有式Ia的12种化合物A-30.001至A-30.012,其中R1是H,R5是Cyp,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]-2-吡啶基]并且R2如表Z中所定义。
表A-31提供了具有式Ia的12种化合物A-31.001至A-31.012,其中R1是H,R5是CH2CF3,R4a是[5-(三氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-32提供了具有式Ia的12种化合物A-32.001至A-32.012,其中R1是H,R5是CH2CF3,R4a是[5-(三氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-33提供了具有式Ia的12种化合物A-33.001至A-33.012,其中R1是H,R5是CH2CF3,R4a是[5-(二氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-34提供了具有式Ia的12种化合物A-34.001至A-34.012,其中R1是H,R5是CH2CF3,R4a是[5-(二氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-35提供了具有式Ia的12种化合物A-35.001至A-35.012,其中R1是H,R5是CH2CF3,R4a是[5-(2,2,2-三氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-36提供了具有式Ia的12种化合物A-36.001至A-36.012,其中R1是H,R5是CH2CF3,R4a是[5-(2,2,2-三氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-37提供了具有式Ia的12种化合物A-37.001至A-37.012,其中R1是H,R5是CH2CF3,R4a是[5-(2,2-二氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-38提供了具有式Ia的12种化合物A-38.001至A-38.012,其中R1是H,R5是CH2CF3,R4a是[5-(2,2-二氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-39提供了具有式Ia的12种化合物A-39.001至A-39.012,其中R1是H,R5是CH2CF3,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]嘧啶-2-基]并且R2如表Z中所定义。
表A-40提供了具有式Ia的12种化合物A-40.001至A-40.012,其中R1是H,R5是CH2CF3,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]-2-吡啶基]并且R2如表Z中所定义。
表A-41提供了具有式Ia的12种化合物A-41.001至A-41.012,其中R1是CH3,R5是H,R4a是[5-(三氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-42提供了具有式Ia的12种化合物A-42.001至A-42.012,其中R1是CH3,R5是H,R4a是[5-(三氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-43提供了具有式Ia的12种化合物A-43.001至A-43.012,其中R1是CH3,R5是H,R4a是[5-(二氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-44提供了具有式Ia的12种化合物A-44.001至A-44.012,其中R1是CH3,R5是H,R4a是[5-(二氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-45提供了具有式Ia的12种化合物A-45.001至A-45.012,其中R1是CH3,R5是H,R4a是[5-(2,2,2-三氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-46提供了具有式Ia的12种化合物A-46.001至A-46.012,其中R1是CH3,R5是H,R4a是[5-(2,2,2-三氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-47提供了具有式Ia的12种化合物A-47.001至A-47.012,其中R1是CH3,R5是H,R4a是[5-(2,2-二氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-48提供了具有式Ia的12种化合物A-48.001至A-48.012,其中R1是CH3,R5是H,R4a是[5-(2,2-二氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-49提供了具有式Ia的12种化合物A-49.001至A-49.012,其中R1是CH3,R5是H,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]嘧啶-2-基]并且R2如表Z中所定义。
表A-50提供了具有式Ia的12种化合物A-50.001至A-50.012,其中R1是CH3,R5是H,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]-2-吡啶基]并且R2如表Z中所定义。
表A-51提供了具有式Ia的12种化合物A-51.001至A-51.012,其中R1是CH3,R5是CH3,R4a是[5-(三氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-52提供了具有式Ia的12种化合物A-52.001至A-52.012,其中R1是CH3,R5是CH3,R4a是[5-(三氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-53提供了具有式Ia的12种化合物A-53.001至A-53.012,其中R1是CH3,R5是CH3,R4a是[5-(二氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-54提供了具有式Ia的12种化合物A-54.001至A-54.012,其中R1是CH3,R5是CH3,R4a是[5-(二氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-55提供了具有式Ia的12种化合物A-55.001至A-55.012,其中R1是CH3,R5是CH3,R4a是[5-(2,2,2-三氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-56提供了具有式Ia的12种化合物A-56.001至A-56.012,其中R1是CH3,R5是CH3,R4a是[5-(2,2,2-三氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-57提供了具有式Ia的12种化合物A-57.001至A-57.012,其中R1是CH3,R5是CH3,R4a是[5-(2,2-二氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-58提供了具有式Ia的12种化合物A-58.001至A-58.012,其中R1是CH3,R5是CH3,R4a是[5-(2,2-二氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-59提供了具有式Ia的12种化合物A-59.001至A-59.012,其中R1是CH3,R5是CH3,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]嘧啶-2-基]并且R2如表Z中所定义。
表A-60提供了具有式Ia的12种化合物A-60.001至A-60.012,其中R1是CH3,R5是CH3,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]-2-吡啶基]并且R2如表Z中所定义。
表A-61提供了具有式Ia的12种化合物A-61.001至A-61.012,其中R1是CH3,R5是Cyp,R4a是[5-(三氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-62提供了具有式Ia的12种化合物A-62.001至A-62.012,其中R1是CH3,R5是Cyp,R4a是[5-(三氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-63提供了具有式Ia的12种化合物A-63.001至A-63.012,其中R1是CH3,R5是Cyp,R4a是[5-(二氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-64提供了具有式Ia的12种化合物A-64.001至A-64.012,其中R1是CH3,R5是Cyp,R4a是[5-(二氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-65提供了具有式Ia的12种化合物A-65.001至A-65.012,其中R1是CH3,R5是Cyp,R4a是[5-(2,2,2-三氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-66提供了具有式Ia的12种化合物A-66.001至A-66.012,其中R1是CH3,R5是Cyp,R4a是[5-(2,2,2-三氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-67提供了具有式Ia的12种化合物A-67.001至A-67.012,其中R1是CH3,R5是Cyp,R4a是[5-(2,2-二氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-68提供了具有式Ia的12种化合物A-68.001至A-68.012,其中R1是CH3,R5是Cyp,R4a是[5-(2,2-二氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-69提供了具有式Ia的12种化合物A-69.001至A-69.012,其中R1是CH3,R5是Cyp,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]嘧啶-2-基]并且R2如表Z中所定义。
表A-70提供了具有式Ia的12种化合物A-70.001至A-70.012,其中R1是CH3,R5是Cyp,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]-2-吡啶基]并且R2如表Z中所定义。
表A-71提供了具有式Ia的12种化合物A-71.001至A-71.012,其中R1是CH3,R5是CH2CF3,R4a是[5-(三氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-72提供了具有式Ia的12种化合物A-72.001至A-72.012,其中R1是CH3,R5是CH2CF3,R4a是[5-(三氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-73提供了具有式Ia的12种化合物A-73.001至A-73.012,其中R1是CH3,R5是CH2CF3,R4a是[5-(二氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-74提供了具有式Ia的12种化合物A-74.001至A-74.012,其中R1是CH3,R5是CH2CF3,R4a是[5-(二氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-75提供了具有式Ia的12种化合物A-75.001至A-75.012,其中R1是CH3,R5是CH2CF3,R4a是[5-(2,2,2-三氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-76提供了具有式Ia的12种化合物A-76.001至A-76.012,其中R1是CH3,R5是CH2CF3,R4a是[5-(2,2,2-三氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-77提供了具有式Ia的12种化合物A-77.001至A-77.012,其中R1是CH3,R5是CH2CF3,R4a是[5-(2,2-二氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-78提供了具有式Ia的12种化合物A-78.001至A-78.012,其中R1是CH3,R5是CH2CF3,R4a是[5-(2,2-二氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-79提供了具有式Ia的12种化合物A-79.001至A-79.012,其中R1是CH3,R5是CH2CF3,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]嘧啶-2-基]并且R2如表Z中所定义。
表A-80提供了具有式Ia的12种化合物A-80.001至A-80.012,其中R1是CH3,R5是CH2CF3,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]-2-吡啶基]并且R2如表Z中所定义。
表A-81提供了具有式Ia的12种化合物A-81.001至A-81.012,其中R1是CH2Cyp,R5是H,R4a是[5-(三氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-82提供了具有式Ia的12种化合物A-82.001至A-82.012,其中R1是CH2Cyp,R5是H,R4a是[5-(三氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-83提供了具有式Ia的12种化合物A-83.001至A-83.012,其中R1是CH2Cyp,R5是H,R4a是[5-(二氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-84提供了具有式Ia的12种化合物A-84.001至A-84.012,其中R1是CH2Cyp,R5是H,R4a是[5-(二氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-85提供了具有式Ia的12种化合物A-85.001至A-85.012,其中R1是CH2Cyp,R5是H,R4a是[5-(2,2,2-三氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-86提供了具有式Ia的12种化合物A-86.001至A-86.012,其中R1是CH2Cyp,R5是H,R4a是[5-(2,2,2-三氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-87提供了具有式Ia的12种化合物A-87.001至A-87.012,其中R1是CH2Cyp,R5是H,R4a是[5-(2,2-二氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-88提供了具有式Ia的12种化合物A-88.001至A-88.012,其中R1是CH2Cyp,R5是H,R4a是[5-(2,2-二氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-89提供了具有式Ia的12种化合物A-89.001至A-89.012,其中R1是CH2Cyp,R5是H,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]嘧啶-2-基]并且R2如表Z中所定义。
表A-90提供了具有式Ia的12种化合物A-90.001至A-90.012,其中R1是CH2Cyp,R5是H,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]-2-吡啶基]并且R2如表Z中所定义。
表A-91提供了具有式Ia的12种化合物A-91.001至A-91.012,其中R1是CH2Cyp,R5是CH3,R4a是[5-(三氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-92提供了具有式Ia的12种化合物A-92.001至A-92.012,其中R1是CH2Cyp,R5是CH3,R4a是[5-(三氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-93提供了具有式Ia的12种化合物A-93.001至A-93.012,其中R1是CH2Cyp,R5是CH3,R4a是[5-(二氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-94提供了具有式Ia的12种化合物A-94.001至A-94.012,其中R1是CH2Cyp,R5是CH3,R4a是[5-(二氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-95提供了具有式Ia的12种化合物A-95.001至A-95.012,其中R1是CH2Cyp,R5是CH3,R4a是[5-(2,2,2-三氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-96提供了具有式Ia的12种化合物A-96.001至A-96.012,其中R1是CH2Cyp,R5是CH3,R4a是[5-(2,2,2-三氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-97提供了具有式Ia的12种化合物A-97.001至A-97.012,其中R1是CH2Cyp,R5是CH3,R4a是[5-(2,2-二氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-98提供了具有式Ia的12种化合物A-98.001至A-98.012,其中R1是CH2Cyp,R5是CH3,R4a是[5-(2,2-二氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-99提供了具有式Ia的12种化合物A-99.001至A-99.012,其中R1是CH2Cyp,R5是CH3,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]嘧啶-2-基]并且R2如表Z中所定义。
表A-100提供了具有式Ia的12种化合物A-100.001至A-100.012,其中R1是CH2Cyp,R5是CH3,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]-2-吡啶基]并且R2如表Z中所定义。
表A-101提供了具有式Ia的12种化合物A-101.001至A-101.012,其中R1是CH2Cyp,R5是Cyp,R4a是[5-(三氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-102提供了具有式Ia的12种化合物A-102.001至A-102.012,其中R1是CH2Cyp,R5是Cyp,R4a是[5-(三氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-103提供了具有式Ia的12种化合物A-103.001至A-103.012,其中R1是CH2Cyp,R5是Cyp,R4a是[5-(二氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-104提供了具有式Ia的12种化合物A-104.001至A-104.012,其中R1是CH2Cyp,R5是Cyp,R4a是[5-(二氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-105提供了具有式Ia的12种化合物A-105.001至A-105.012,其中R1是CH2Cyp,R5是Cyp,R4a是[5-(2,2,2-三氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-106提供了具有式Ia的12种化合物A-106.001至A-106.012,其中R1是CH2Cyp,R5是Cyp,R4a是[5-(2,2,2-三氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-107提供了具有式Ia的12种化合物A-107.001至A-107.012,其中R1是CH2Cyp,R5是Cyp,R4a是[5-(2,2-二氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-108提供了具有式Ia的12种化合物A-108.001至A-108.012,其中R1是CH2Cyp,R5是Cyp,R4a是[5-(2,2-二氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-109提供了具有式Ia的12种化合物A-109.001至A-109.012,其中R1是CH2Cyp,R5是Cyp,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]嘧啶-2-基]并且R2如表Z中所定义。
表A-110提供了具有式Ia的12种化合物A-110.001至A-110.012,其中R1是CH2Cyp,R5是Cyp,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]-2-吡啶基]并且R2如表Z中所定义。
表A-111提供了具有式Ia的12种化合物A-111.001至A-111.012,其中R1是CH2Cyp,R5是CH2CF3,R4a是[5-(三氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-112提供了具有式Ia的12种化合物A-112.001至A-112.012,其中R1是CH2Cyp,R5是CH2CF3,R4a是[5-(三氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-113提供了具有式Ia的12种化合物A-113.001至A-113.012,其中R1是CH2Cyp,R5是CH2CF3,R4a是[5-(二氟甲氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-114提供了具有式Ia的12种化合物A-114.001至A-114.012,其中R1是CH2Cyp,R5是CH2CF3,R4a是[5-(二氟甲氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-115提供了具有式Ia的12种化合物A-115.001至A-115.012,其中R1是CH2Cyp,R5是CH2CF3,R4a是[5-(2,2,2-三氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-116提供了具有式Ia的12种化合物A-116.001至A-116.012,其中R1是CH2Cyp,R5是CH2CF3,R4a是[5-(2,2,2-三氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-117提供了具有式Ia的12种化合物A-117.001至A-117.012,其中R1是CH2Cyp,R5是CH2CF3,R4a是[5-(2,2-二氟乙氧基)嘧啶-2-基]并且R2如表Z中所定义。
表A-118提供了具有式Ia的12种化合物A-118.001至A-118.012,其中R1是CH2Cyp,R5是CH2CF3,R4a是[5-(2,2-二氟乙氧基)-2-吡啶基]并且R2如表Z中所定义。
表A-119提供了具有式Ia的12种化合物A-119.001至A-119.012,其中R1是CH2Cyp,R5是CH2CF3,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]嘧啶-2-基]并且R2如表Z中所定义。
表A-120提供了具有式Ia的12种化合物A-120.001至A-120.012,其中R1是CH2Cyp,R5是CH2CF3,R4a是[5-[(Z)-3,3,3-三氟丙-1-烯氧基]-2-吡啶基]并且R2如表Z中所定义。
还可获得具有式IIa的胺的某些中间体化合物
具有式IIa的化合物的具体实例是其中(A)R1是CH2Cyp,并且R4a选自J1至J10;(B)R1是甲基,并且R4a选自J1至J10;(C)R1是氢,并且R4a选自J1至J10。
还使得可获得具有式VIb的胺的某些中间体化合物,其中的一些是新颖的。
具有式VIb的化合物的具体实例是其中(A)R3是甲基,并且R4a选自J1至J10,并且R5是甲基;并且(B)R3是甲基,并且R4a选自J1至J10,并且R5是氢。
使得具有式XII和XIV的胺的某些中间体化合物在本文中可获得,其中的一些是新颖的。
具有式XIII和XIV的化合物的具体实例是其中(A)R1是CH2Cyp,R3是甲基,并且R2如表Z中所定义;(B)R1是甲基,R3是甲基,并且R2如表Z中所定义;(C)R1是氢,R3是甲基,并且R2如表Z中所定义。
还可获得具有式XXa的胺的某些中间体化合物
具有式XXa的化合物的具体实例是其中(A)A1是N,R1是CH2Cyp,并且R2如表Z中所定义;(B)A1是N,R1是甲基,并且R2如表Z中所定义;(C)A1是N,R1是氢,并且R2如表Z中所定义;(D)A1是CH,R1是CH2Cyp,并且R2如表Z中所定义;(E)A1是CH,R1是甲基,并且R2如表Z中所定义;并且(F)A1是CH,R1是氢,并且R2如表Z中所定义。
在另一方面,本发明相应地提供了具有式IIa、VIa、XIII、XIV和XXa的化合物,其中在每种情况下,在适用的情况下,A1、R1、R2、R3、R4和R5如在第一方面中对式I所定义。此外,对于式I所示的相应实施例也适用于具有式IIa、VIa、XIII、XIV和XXa的化合物。
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,即使是在低的施用比率下,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的动物有害生物(如昆虫或蜱螨目的代表)的所有的或个别的发育阶段。根据本发明的活性成分的杀昆虫或杀螨活性可以本身直接显示,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。
以上提及的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)、拟缘蝽属物种(Acrosternum spp)、苜蓿盲蝽(Adelphocoris lineolatus)、土黄缘蝽、海虾盾缘蝽(Bathycoelia thalassina)、土长蝽属物种、臭虫属物种、Clavigralla tomentosicollis、盲蝽属物种(Creontiades spp.)、可可瘤盲蝽、Dichelops furcatus、棉红蝽属物种、埃德萨属物种(Edessa spp)、美洲蝽属物种(Euchistus spp.)、六斑菜蝽(Eurydema pulchrum)、扁盾蝽属物种、茶翅蝽、具凹巨股长蝽(Horcias nobilellus)、稻缘蝽属物种、草盲蝽属物种、热带硕蚧属物种、卷心菜斑色蝽(Murgantia histrionic)、新长缘蝽属物种、烟盲蝽(Nesidiocoris tenuis)、绿蝽属物种、拟长蝽(Nysius simulans)、海岛蝽象、皮蝽属物种、壁蝽属物种、红猎蝽属物种、可可褐盲蝽、栗土蝽(Scaptocoris castanea)、黑蝽属物种(Scotinophara spp.)、Thyanta属物种、锥鼻虫属物种、木薯网蝽(Vatiga illudens);
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)。
在另一方面,本发明还可涉及一种控制由植物寄生线虫(内寄生线虫、半内寄生线虫和外寄生线虫)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.)。
本发明的化合物还可以具有针对软体动物的活性。其实例包括例如福寿螺科;蛞蝓科(Arion)(黑蛞蝓(A.ater)、环状蛞蝓(A.circumscriptus)、棕阿勇蛞蝓(A.hortensis)、红蛞蝓(A.rufus));巴蜗牛科(Bradybaenidae)(灌木巴蜗牛(Bradybaenafruticum));葱蜗牛属(Cepaea)(花园葱蜗牛(C.hortensis)、森林葱蜗牛(C.Nemoralis));ochlodina;野蛞蝓属(Deroceras)(野灰蛞蝓(D.agrestis)、D.empiricorum、光滑野蛞蝓(D.laeve)、网纹野蛞蝓(D.reticulatum));圆盘螺属(Discus)(圆形圆盘蜗牛(D.rotundatus));Euomphalia;土蜗属(Galba)(截口土蜗(G.trunculata));小蜗牛属(Helicelia)(伊塔拉小蜗牛(H.itala)、布维小蜗牛(H.obvia));大蜗牛科(Helicidae)(Helicigona arbustorum);Helicodiscus;大蜗牛(Helix)(开口大蜗牛(H.aperta));蛞蝓属(Limax)(利迈科斯蛞蝓(L.cinereoniger)、黄蛞蝓(L.flavus)、边缘蛞蝓(L.marginatus)、大蛞蝓(L.maximus)、柔蛞蝓(L.tenellus));椎实螺属(Lymnaea);Milax(小蛞蝓科)(黑色小蛞蝓(M.gagates)、边缘小蛞蝓(M.marginatus)、硕氏小蛞蝓(M.sowerbyi));钻螺属(Opeas);瓶螺属(Pomacea)(福寿螺(P.canaticulata));瓦娄蜗牛属(Vallonia)和Zanitoides。
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,或者在此类植物的器官,如果实、花、叶、茎、块茎或根上,并且在一些情况下,甚至在随后的时间点形成的植物器官仍保持受保护以抵抗这些有害生物。
特别地,适宜的目标作物是,谷物,如小麦、大麦、黑麦、燕麦、稻、玉米或高梁;甜菜,如糖用甜菜或饲料甜菜;水果,例如仁果、核果或无核小果,如苹果、梨、李子、桃、杏、樱桃或浆果,例如草莓、覆盆子或黑莓;豆科作物,如菜豆、小扁豆、豌豆或大豆;油料作物,如油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻、可可豆或落花生;瓜类作物,如南瓜、黄瓜或甜瓜;纤维植物,如棉花、亚麻、大麻或黄麻;柑橘类水果,如橙子、柠檬、葡萄柚或橘子;蔬菜,如菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、番茄、马铃薯或灯笼椒;樟科,如鳄梨、肉桂或樟脑;以及还有烟草、坚果、咖啡、茄子、甘蔗、荼、胡椒、葡萄藤、蛇麻草、车前草科以及乳胶植物。
本发明的组合物和/或方法还可以用于任何观赏植物和/或蔬菜作物(包括花、灌木、阔叶树和常绿植物)。
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)、杂种蛾蝶花(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、青葱(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(Citrilluslanatus)、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(Cyanaraspp.)(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、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、甜椒、番茄和黄瓜。
根据本发明的活性成分尤其适合于控制棉花、蔬菜、玉米、稻以及大豆作物上的豆蚜、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)。
具有式I的化合物特别适合于控制:
·半翅目的有害生物,例如以下物种中的一种或多种:烟粉虱(Bemisia tabaci)、豆蚜、桃蚜、禾谷缢管蚜(Rhopalosiphum Padi)、褐稻虱(Nilaparvata lugens)、以及英雄美洲蝽(Euschistus heros)(优选在蔬菜、大豆、以及甘蔗上);
·鳞翅目的有害生物,例如以下物种中的一种或多种:海灰翅夜蛾、草地贪夜蛾(Spodoptera frugiperda)、小菜蛾、稻纵卷叶螟(Cnaphalocrocis medinalis)、苹果蠹蛾、大豆尺蠖(Chrysodeixis includes)、二化螟、南美玉米苗斑螟(Elasmopalpuslignosellus)、大豆尺夜蛾(Pseudoplusia includens)、以及番茄斑潜蝇(优选在蔬菜和玉米上);
·缨翅目的有害生物,如蓟马科,例如烟蓟马和西花蓟马中的一种或多种(优选在蔬菜上);以及
·(如鞘翅目的)土壤有害生物,例如物种黄瓜条叶甲、叩甲属物种以及马铃薯甲虫(优选在蔬菜和玉米上)。
术语“作物”应当理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成一种或多种选择性作用毒素的作物植物,这些毒素是如已知例如来自于产毒素细菌,尤其是芽孢杆菌属的那些细菌。
可由此类转基因植物表达的毒素包括例如杀昆虫蛋白,例如来自蜡样芽胞杆菌或日本金龟子芽孢杆菌的杀昆虫蛋白;或者来自苏云金芽孢杆菌的杀昆虫蛋白,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;或细菌定殖线虫的杀昆虫蛋白,例如光杆状菌属物种(Photorhabdus spp.)或致病杆菌属物种(Xenorhabdus spp.),如发光杆菌(Photorhabdus luminescens)、嗜线虫致病杆菌(Xenorhabdus nematophilus);由动物产生的毒素,如蝎毒素、蛛毒素、蜂毒素和其他昆虫特异性神经毒素;由真菌产生的毒素,如链霉菌毒素,植物凝集素,如豌豆凝集素、大麦凝集素或雪花莲凝集素;凝集素类;蛋白酶抑制剂,如胰蛋白酶抑制剂、丝蛋白酶抑制剂、马铃薯糖蛋白、胱抑素、木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),如蓖麻毒素、玉米-RIP、相思豆毒素、丝瓜籽毒蛋白、皂草毒素蛋白或异株泻根毒蛋白;类固醇代谢酶,如3-羟基类固醇氧化酶、蜕化类固醇-UDP-糖基-转移酶、胆固醇氧化酶、蜕化素抑制剂、HMG-COA-还原酶、离子通道阻断剂如钠通道或钙通道阻断剂、保幼激素酯酶、利尿激素受体、芪合成酶、联苄合成酶、几丁质酶和葡聚糖酶。
在本发明的上下文中,δ-内毒素(例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C)或营养期杀昆虫蛋白(Vip)(例如Vip1、Vip2、Vip3或Vip3A)应理解为显然还包括混合型毒素、截短的毒素和经修饰的毒素。混合型毒素是通过那些蛋白的不同结构域的新组合重组产生的(参见例如,WO 02/15701)。截短的毒素,例如截短的Cry1Ab是已知的。在经修饰的毒素的情况下,天然存在的毒素的一个或多个氨基酸被置换。在此类氨基酸置换中,优选将非天然存在的蛋白酶识别序列插入毒素中,例如像在Cry3A055的情况下,组织蛋白酶-G-识别序列被插入Cry3A毒素中(参见WO 03/018810)。
此类毒素或能够合成此类毒素的转基因植物的实例披露于例如EP-A-0 374 753、WO 93/07278、WO 95/34656、EP-A-0 427 529、EP-A-451 878以及WO 03/052073中。
用于制备此类转基因植物的方法通常是本领域技术人员已知的并且描述在例如以上提及的公开物中。CryI型脱氧核糖核酸及其制备例如从WO 95/34656、EP-A-0 367474、EP-A-0 401 979和WO 90/13651中已知。
包含在转基因植物中的毒素赋予植物对有害昆虫的耐受性。此类昆虫可以存在于任何昆虫分类群,但尤其常见于甲虫(鞘翅目)、双翅昆虫(双翅目)和蛾(鳞翅目)。
含有一种或多种编码杀昆虫抗性并且表达一种或多种毒素的基因的转基因植物是已知的并且其中一些是可商购的。此类植物的实例是:(玉米品种,表达Cry1Ab毒素);YieldGard(玉米品种,表达Cry3Bb1毒素);YieldGard(玉米品种,表达Cry1Ab和Cry3Bb1毒素);(玉米品种,表达Cry9C毒素);Herculex(玉米品种,表达Cry1Fa2毒素和获得对除草剂草铵膦铵耐受性的酶膦丝菌素N-乙酰基转移酶(PAT));NuCOTN(棉花品种,表达Cry1Ac毒素);Bollgard(棉花品种,表达Cry1Ac毒素);Bollgard(棉花品种,表达Cry1Ac和Cry2Ab毒素);(棉花品种,表达Vip3A和Cry1Ab毒素);(马铃薯品种,表达Cry3A毒素);GT Advantage(GA21耐草甘膦性状)、CB Advantage(Bt11玉米螟(CB)性状)以及
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,被赋予对欧洲玉米螟(玉米螟和粉茎螟)攻击的抗性。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,被赋予对欧洲玉米螟(玉米螟和粉茎螟)攻击的抗性。Bt176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。
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毒素被赋予昆虫抗性的玉米。此毒素是通过插入组织蛋白酶-G-蛋白酶识别序列而修饰的Cry3A055。此类转基因玉米植物的制备描述于WO 03/018810中。
4.MON 863玉米,来自孟山都欧洲公司(Monsanto Europe S.A.),270-272特弗伦大道(Avenue de Tervuren),B-1150布鲁塞尔,比利时,登记号C/DE/02/9。MON 863表达Cry3Bb1毒素,并且对某些鞘翅目昆虫有抗性。
5.IPC 531棉花,来自孟山都欧洲公司,270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/ES/96/02。
6.1507玉米,来自先锋海外公司(Pioneer Overseas Corporation),特德斯科大道(Avenue Tedesco),7B-1160布鲁塞尔,比利时,登记号C/NL/00/10。遗传修饰的玉米,表达蛋白Cry1F以获得对某些鳞翅目昆虫的抗性,并且表达PAT蛋白以获得对除草剂草铵膦铵盐的耐受性。
7.NK603×MON 810玉米,来自孟山都欧洲公司,270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/GB/02/M3/03。通过将遗传修饰的品种NK603和MON 810杂交,由常规育种的杂交玉米品种组成。NK603×MON 810玉米转基因地表达由土壤杆菌属菌株CP4获得的蛋白CP4 EPSPS,这赋予了对除草剂(含有草甘膦)的耐受性,以及还有由苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subsp.kurstaki)获得的Cry1Ab毒素,这产生了对某些鳞翅目昆虫(包括欧洲玉米螟)的耐受性。
抗昆虫的植物的转基因作物还描述于BATS(生物安全与可持续发展中心(Zentrumfür Biosicherheit und Nachhaltigkeit),BATS中心(Zentrum BATS),克拉斯崔舍(Clarastrasse)13,巴塞尔(Basel)4058,瑞士)报告2003(http://bats.ch)中。
术语“作物”应理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成具有选择性作用的抗病原物质的作物植物,这些抗病原物质是例如像所谓的“病程相关蛋白”(PRP,参见例如EP-A-0 392 225)。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 95/33818和EP-A-0 353191中已知。生产此类转基因植物的方法对于本领域的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。
作物还可以经修饰以增加对真菌(例如镰孢霉属、炭疽病或疫霉属)、细菌(例如假单胞菌属)或病毒(例如马铃薯卷叶病毒、番茄斑萎病毒、黄瓜花叶病毒)病原体的抗性。
作物还包括对线虫(如大豆异皮线虫)具有增加的抗性的那些作物。
具有对非生物性胁迫的耐受性的作物包括例如通过NF-YB或本领域中已知的其他蛋白质的表达对干旱、高盐、高温、寒冷、霜或光辐射具有增加的耐受性的那些作物。
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;所谓的“病程相关蛋白”(PRP;参见例如EP-A-0 392 225);由微生物产生的抗病原物质,例如肽抗生素或杂环抗生素(参见例如WO 95/33818)或参与植物病原体防御的蛋白或多肽因子(所谓的“植物疾病抗性基因”,如WO03/000906中所述)。
根据本发明的组合物的其他使用范围是保护所储存的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。
本发明提供了用于疗法的第一方面的化合物。本发明提供了第一方面的化合物,用于控制动物体内或体表的寄生虫。本发明进一步提供了第一方面的化合物,用于控制动物的体外寄生虫。本发明进一步提供了第一方面的化合物,用于预防和/或治疗由体外寄生虫传播的疾病。
本发明提供了第一方面的化合物用于制造用于控制动物体内或体表的寄生虫的药物中的用途。本发明进一步提供了第一方面的化合物用于制造用于控制动物的体外寄生虫的药物中的用途。本发明进一步提供了第一方面的化合物用于制造用于预防和/或治疗由体外寄生虫传播的疾病的药物中的用途。
本发明提供了第一方面的化合物在控制动物体内或体表的寄生虫中的用途。本发明进一步提供了第一方面的化合物在控制动物的体外寄生虫中的用途。
当在动物体内或体表的寄生虫的上下文中使用时,术语“控制”是指减少有害生物或寄生虫的数量,消除有害生物或寄生虫和/或防止进一步的有害生物或寄生虫侵染。
当在动物体内或体表的寄生虫的上下文中使用时,术语“治疗”是指抑制、减缓、停止或逆转现有症状或疾病的进展或严重性。
当在动物体内或体表的寄生虫的上下文中使用时,术语“预防”是指避免在动物中发展症状或疾病。
当在动物体内或体表的寄生虫的上下文中使用时,术语“动物”可能是指哺乳动物和非哺乳动物,如鸟或鱼。在哺乳动物的情况下,它可以是人类或非人类哺乳动物。非人类哺乳动物包括但不限于家畜动物和宠物。家畜动物包括但不限于牛、骆驼、猪、绵羊、山羊和马。宠物包括但不限于狗、猫和兔。
“寄生虫”是生活在宿主动物体内或体表并通过以宿主动物为代价获取营养物而受益的有害生物。“体内寄生虫”是生活在宿主动物体内的寄生虫。“体外寄生虫”是生活在宿主动物体表的寄生虫。体外寄生虫包括但不限于壁虱、昆虫和甲壳类动物(例如海虱)。壁虱(或蜱螨目)亚纲包括蜱和螨。蜱包括但不限于以下属的成员:扇头蜱属(Rhipicaphalus),例如微小扇头蜱(Rhipicaphalus microplus)(微小牛蜱(Boophilusmicroplus))和血红扇头蜱(Rhipicephalus sanguineus);Amblyomrna;革蜱属(Dermacentor);血蜱属(Haemaphysalis);璃眼蜱属(Hyalomma);硬蜱属(Ixodes);角头蜱属(Rhipicentor);牛壁虱属(Margaropus);锐缘蜱属(Argas);耳蜱属(Otobius);和钝缘蜱属(Ornithodoros)。螨包括但不限于以下属的成员:皮螨属,例如牛皮痒螨;痒螨属,例如羊痒螨;姬螯螨属;皮刺螨属;例如鸡皮刺螨;禽刺螨属(Ortnithonyssus);蠕形螨属,例如犬蠕形螨;疥螨属,例如人疥螨;以及疮螨属。昆虫包括但不限于以下目的成员:蚤目、双翅目、毛虱目、鳞翅目、鞘翅目和同翅目。蚤目的成员包括但不限于猫栉头蚤和犬栉头蚤(Ctenocephatides canis)。双翅目的成员包括但不限于蝇属物种;肤蝇,例如马蝇和羊狂蝇;螫蝇(biting flies);虻,例如麻虻属物种和Tabunus物种;黑角蝇属,例如扰血蝇;螫蝇属(Stomoxys);绿蝇属;蠓;以及蚊。毛虱目类的成员包括但不限于吸血虱和嚼虱(chewinglice),例如羊毛虱(Bovicola Ovis)和牛羽虱。
当在动物体内或体表的寄生虫的上下文中使用时,术语“有效量”是指本发明化合物或其盐的量或剂量,其以单剂量或多剂量给予动物时,在动物体内或体表提供了希望的效果。主治诊断专家(作为本领域技术人员)通过使用已知技术和通过观察在类似情况下获得的结果,可以容易地确定有效量。在确定有效量时,主治诊断专家考虑了许多因素,包括但不限于:哺乳动物的种类;其大小、年龄和总体健康状况;要控制的寄生虫和侵染程度;所涉及的特定疾病或病症;疾病或病症的累及程度或严重性;个体反应;给予的特定化合物;给予模式;给予制剂的生物利用度特征;所选择的剂量方案;伴随药物的使用;和其他相关情况。
本发明的化合物可以通过具有希望效果的任何途径给予动物,包括但不限于局部、口服、肠胃外和皮下。局部给予是优选的。适用于局部给予的配制品包括例如溶液、乳液和悬浮液,并且可以采取倾倒、点涂、喷涂、喷雾栏(spray race)或浸渍的形式。在替代方案中,本发明的化合物可以通过耳标或颈圈给予。
本发明的化合物的盐形式包括药学上可接受的盐和兽医学上可接受的盐两者,它们可以不同于农用化学上可接受的盐。药学和兽医学上可接受的盐以及制备它们的常用方法在本领域中是熟知的。参见例如,Gould,P.L.,"Salt selection for basic drugs[基础药物的盐选择]",International Journal of Pharmaceutics[国际药剂学杂志],33:201-217(1986);Bastin,R.J.等人"Salt Selection and Optimization Procedures forPharmaceutical New Chemical Entities[制药新化学实体的盐选择和最优化程序]",Organic Process Research andDevelopment[有机过程研究与开发],4:427-435(2000);以及Berge,S.M.等人,"Pharmaceutical Salts[药用盐]",Journal of PharmaceuticalSciences[药物科学杂志],66:1-19,(1977)。合成领域的技术人员将理解,使用本领域普通技术人员熟知的技术和条件,本发明的化合物容易转化成盐,并且可以作为盐(如盐酸盐)分离。此外,合成领域的技术人员将理解,本发明的化合物容易转化成相应的游离碱,并且可以作为相应的游离碱从相应的盐中分离出来。
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、喷洒、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(室内滞留喷洒)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,如非织物或织物材料,该材料呈网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于这些物品的制造中)。
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。此种施用可以通过涂刷、轧制、喷洒、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对在基底上的有害生物的残留控制,该基底是如呈网织品、被覆物、被褥、窗帘以及帐篷的形式的织物材料(或可以用于这些物品的制造中)。
有待处理的基底(包括非织物、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、WO 2003/034823、US 5631072、WO 2005/64072、WO 2006/128870、EP 1724392、WO 2005113886或WO2007/090739。
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所提及的鳞翅目和来自鞘翅目的蛀木昆虫,尤其是对抗下表A和B中列出的蛀木虫:
表A.具有经济重要性的外来蛀木虫的实例。
表B.具有经济重要性的本地蛀木虫的实例。
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。
具体而言,本发明可以用于控制以草坪草的根部为食的昆虫有害生物,这些昆虫有害生物包括蛴螬(如圆头犀金龟属物种(Cyclocephala spp.)(例如蒙面金龟子、C.lurida)、切根鳃金龟属物种(Rhizotrogus spp.)(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(Ataenius spp.)(例如草坪草黑金龟(Black turfgrass 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(Scapteriscus spp.)、非洲蝼蛄(Gryllotalpa africana))以及大蚊幼虫(leatherjackets)(欧洲大蚊(European crane fly)、大蚊属物种(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(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.),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以草坪草叶子为食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(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,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对外寄生虫如硬蜱、软蜱、疥螨、秋螨、蝇(叮咬和舔舐)、寄生性蝇幼虫,虱、发虱、鸟虱和跳蚤具有活性。
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(Felicola spp.)。
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(Varroa spp.)。
轴螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨目(Acaridida)(无气门亚目(Astigmata)),例如蜂盾螨属物种(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材料如木材、纺织品、塑料、粘合剂、胶、漆料、纸张和卡片、皮革、地板和建筑物的情况下免受昆虫侵染。
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、长毛天牛、家具窃蠹、红毛窃蠹、梳角细脉窃蠹、Dendrobium pertinex、松芽枝窃蠹、Priobiumcarpini、褐粉蠹、非洲粉蠹、南方粉蠹、栎粉蠹、柔毛粉蠹、胸粉蠹、鳞毛粉蠹、材小蠹属物种、条木小蠹属物种、咖啡黑长蠹、槲长蠹、棕异翅长蠹、双棘长蠹属与竹长蠹;以及还有膜翅类,如蓝黑树蜂、大树蜂、泰加大树蜂与Urocerus augur;以及白蚁类,如欧洲木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁、印巴结构木异白蚁、黄胸散白蚁、桑特散白蚁、欧洲散白蚁、达尔文澳白蚁、内华达古白蚁与家白蚁;以及蛀虫,如衣鱼。具有式I和I’a的化合物、或其盐尤其适用于控制选自以下科的一种或多种有害生物:夜蛾科、菜蛾科、叶甲科、蓟马科、蝽科、卷蛾科、飞虱科、蚜科、夜蛾科、草螟科、根结线虫科和异皮线虫科。在每个方面的优选实施例中,化合物TX(其中缩写“TX”意指“选自表A-1至A-120和表P中定义的化合物的一种化合物”)控制选自以下科的一种或多种有害生物:夜蛾科、菜蛾科、叶甲科、蓟马科、蝽科、卷蛾科、飞虱科、蚜科、夜蛾科、草螟科、根结线虫科和异皮线虫科。
具有式I和I’a的化合物或其盐尤其适用于控制选自以下属的一种或多种有害生物:灰翅夜蛾属物种、菜蛾属物种、花蓟马属物种、蓟马属物种、美洲蝽属物种、蠹蛾属(Cydia)物种、褐稻虱属物种、桃蚜属物种、蚜属物种、根萤叶甲属物种、缢管蚜属物种、尺夜蛾属物种和禾草螟属物种。在每个方面的优选实施例中,化合物TX(其中缩写“TX”意指“选自表A-1至A-120和表P中定义的化合物的一种化合物”)控制选自以下属的一种或多种有害生物:灰翅夜蛾属物种、菜蛾属物种、花蓟马属物种、蓟马属物种、美洲蝽属物种、蠹蛾属(Cydia)物种、褐稻虱属物种、桃蚜属物种、蚜属物种、根萤叶甲属物种、缢管蚜属物种、尺夜蛾属物种和禾草螟属物种。
具有式I和I’a的化合物或其盐尤其适用于控制以下项的一种或多种:海灰翅夜蛾、小菜蛾、西花蓟马、烟蓟马、英雄美洲蝽、苹果蠹蛾、褐稻虱、桃蚜、大豆尺蠖、豆蚜、黄瓜条叶甲、禾谷缢管蚜、和二化螟。
在每个方面的优选实施例中,化合物TX(其中缩写“TX”意指“选自表A-1至A-120和表P中定义的化合物中的一种化合物”)控制以下项的一种或多种:海灰翅夜蛾、小菜蛾、西花蓟马、烟蓟马、英雄美洲蝽、苹果蠹蛾、褐稻虱、桃蚜、大豆尺蠖、豆蚜、黄瓜条叶甲、禾谷缢管蚜、和二化螟,如海灰翅夜蛾+TX、小菜蛾+TX;西花蓟马+TX、烟蓟马+TX、英雄美洲蝽+TX、苹果蠹蛾+TX、褐稻虱+TX、桃蚜+TX、大豆尺蠖+TX、豆蚜+TX、黄瓜条叶甲+TX、禾谷缢管蚜+TX、和二化螟+TX。
在每个方面的实施例中,选自表A-1至A-120和表P中定义的化合物中的一种化合物适用于控制棉花、蔬菜、玉米、谷物、水稻和大豆作物上的海灰翅夜蛾、小菜蛾、西花蓟马、烟蓟马、英雄美洲蝽、苹果蠹蛾、褐稻虱、桃蚜、大豆尺蠖、豆蚜、黄瓜条叶甲、禾谷缢管蚜、和二化螟。
在实施例中,选自表A-1至A-120和表P中定义的化合物中的一种化合物适用于控制甘蓝夜蛾(Mamestra)(优选地在蔬菜上)、苹果蠹蛾(优选地在苹果上)、小绿叶蝉(Empoasca)(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)。
根据本发明的化合物可以具有任何数量的益处,尤其包括针对保护植物对抗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(针对地上和地下的非靶标生物体(如鱼、鸟和蜂))、改进的物理-化学特性、或增加的生物可降解性)。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节肢动物,特别是传粉者(如蜜蜂、独居蜂和熊蜂),可以显示出有利的安全性。最特别地,相对于西方蜜蜂。
根据本发明的化合物可以按未经修饰的形式用作杀有害生物剂,但它们通常以多种方式使用配制佐剂(如载体、溶剂以及表面活性物质)被配制成组合物。配制品可以呈不同的实体形式,例如,呈以下形式:撒粉剂、凝胶、可湿性粉剂、水可分散性颗粒剂、水可分散性片剂、泡腾压缩片剂、可乳化浓缩物、微可乳化浓缩物、水包油乳剂、可流动油、水性分散体、油性分散体、悬乳剂、胶囊悬浮液、可乳化颗粒剂、可溶性液体、水溶性浓缩物(以水或水混溶性有机溶剂作为载体)、浸渍的聚合物膜或呈已知的其他形式,例如从Manual onDevelopment and Use of FAO and WHO Specifications for Pesticides[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,第一版,二次修订(2010)中已知的。此类配制品可以直接使用或者在使用前稀释。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。
配制品可以通过例如将活性成分与配制佐剂混合来制备以便获得呈精细分散固体、颗粒剂、溶液、分散体或乳剂形式的组合物。活性成分还可以与其他佐剂(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)一起配制。
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。它们含有的活性成分的量是胶囊重量的按重量计约从25%至95%。活性成分可以呈整体性的固体的形式、呈固体或液体分散体中的精细颗粒的形式或呈适合溶液的形式。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和淀粉黄原酸酯、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,其中活性成分以精细分散颗粒的形式被包含在基础物质的固体基质中,但微胶囊本身未被包裹。
适合于制备根据本发明的组合物的配制佐剂本身是已知的。作为液体载体可以使用:水、甲苯、二甲苯、石油醚、植物油、丙酮、甲基乙基酮、环己酮、酸酐、乙腈、乙酰苯、乙酸戊酯、2-丁酮、碳酸丁烯酯、氯苯、环己烷、环己醇、乙酸烷基酯、二丙酮醇、1,2-二氯丙烷、二乙醇胺、对-二乙基苯、二乙二醇、松香酸二乙二醇酯、二乙二醇丁醚、二乙二醇乙醚、二乙二醇甲醚、N,N-二甲基甲酰胺、二甲基亚砜、1,4-二噁烷、二丙二醇、二丙二醇甲醚、二丙二醇二苯甲酸酯、diproxitol、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、乙二醇丁醚、乙二醇甲醚、γ-丁内酯、甘油、乙酸甘油酯、二乙酸甘油酯、三乙酸甘油酯、十六烷、己二醇、乙酸异戊酯、乙酸异冰片酯、异辛烷、异佛尔酮、异丙苯、肉豆蔻酸异丙酯、乳酸、月桂胺、异亚丙基丙酮、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、油胺、邻二甲苯、苯酚、聚乙二醇、丙酸、乳酸丙酯、碳酸丙烯酯、丙二醇、丙二醇甲醚、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、丙二醇甲醚、二乙二醇甲醚、甲醇、乙醇、异丙醇和更高分子量的醇,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,如月桂基硫酸二乙醇铵;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,如壬基酚乙氧基化物;醇/氧化烯加成产物,如十三烷醇乙氧基化物;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;季胺,如月桂基三甲基氯化铵;脂肪酸的聚乙二醇酯,如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;以及磷酸单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)中。
可以用于杀有害生物配制品的其他佐剂包括结晶抑制剂、粘度调节剂、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含添加剂,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待施用的混合物从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)。许多油衍生物从Compendium of Herbicide Adjuvants[除草剂佐剂纲要],第10版,南伊利诺伊大学(Southern Illinois University),2010已知。
本发明组合物通常包含按重量计从0.1%至99%、尤其是按重量计从0.1%至95%的本发明的化合物和按重量计从1%至99.9%的配制佐剂,该配制佐剂优选地包括按重量计从0%至25%的表面活性物质。而商业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、和受施用方法、施用时间和目标作物支配的其他因素。作为一般性指导,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%):
可乳化浓缩物:
活性成分:1%至95%,优选60%至90%
表面活性剂:1%至30%,优选5%至20%
液体载体:1%至80%,优选1%至35%
尘剂:
活性成分:0.1%至10%,优选0.1%至5%
固体载体:99.9%至90%,优选99.9%至99%
悬浮液浓缩物:
活性成分:5%至75%,优选10%至50%
水:94%至24%,优选88%至30%
表面活性剂:1%至40%,优选2%至30%
可湿性粉剂:
活性成分:0.5%至90%,优选1%至80%
表面活性剂:0.5%至20%,优选1%至15%
固体载体:5%至95%,优选15%至90%
颗粒剂:
活性成分:0.1%至30%,优选0.1%至15%
固体载体:99.5%至70%,优选97%至85%
以下实例进一步说明本发明,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% | - |
将组合与佐剂充分混合并且将混合物在适合的研磨机中充分研磨,从而得到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% |
将组合与佐剂充分混合并且将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。
<u>可乳化浓缩物</u> | |
活性成分 | 10% |
辛基酚聚乙二醇醚(4-5mol的环氧乙烷) | 3% |
十二烷基苯磺酸钙 | 3% |
蓖麻油聚二醇醚(35mol的环氧乙烷) | 4% |
环己酮 | 30% |
二甲苯混合物 | 50% |
在植物保护中可以使用的具有任何所要求的稀释度的乳液可以通过用水稀释由这种浓缩物获得。
<u>尘剂</u> | a) | b) | c) |
活性成分 | 5% | 6% | 4% |
滑石 | 95% | - | - |
高岭土 | - | 94% | - |
矿物填料 | - | - | 96% |
通过将组合与载体混合并且将混合物在适合的研磨机中研磨获得立即可用的尘剂。此类粉剂还可以用于种子的干拌种。
<u>挤出机颗粒剂</u> | |
活性成分 | 15% |
木质素磺酸钠 | 2% |
羧甲基纤维素 | 1% |
高岭土 | 82% |
将组合与佐剂混合并且研磨,并且将混合物用水湿润。将混合物挤出并且然后在空气流中干燥。
<u>包衣颗粒剂</u> | |
活性成分 | 8% |
聚乙二醇(分子量200) | 3% |
高岭土 | 89% |
将精细研磨的组合在混合器中均匀地施用于用聚乙二醇湿润的高岭土中。以此方式获得无尘的包衣颗粒剂。
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% |
硅油(呈在水中75%乳液的形式) | 1% |
水 | 32% |
将精细研磨的组合与佐剂密切混合,从而给出悬浮液浓缩物,可以通过用水稀释由该悬浮液浓缩物获得任何所希望稀释度的悬浮液。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且通过喷洒、倾倒或浸渍保护免受微生物的侵染。
种子处理用的可流动浓缩物
将精细研磨的组合与佐剂密切混合,从而给出悬浮液浓缩物,可以通过用水稀释由该悬浮液浓缩物获得任何所希望稀释度的悬浮液。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且通过喷洒、倾倒或浸渍保护免受微生物的侵染。
缓释的胶囊悬浮液
将28份的组合与2份的芳香族溶剂和7份的甲苯二异氰酸酯/多亚甲基-多苯基异氰酸酯-混合物(8:1)进行混合。将此混合物在1.2份的聚乙烯醇、0.05份的消泡剂和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份水中的2.8份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份的增稠剂和3份的分散剂进行稳定。胶囊悬浮液配制品含有28%的活性成分。中等胶囊的直径是8-15微米。将所得配制品在适用于此目的的装置中作为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)、可乳化颗粒剂(EG)、油包水型乳液(EO)、水包油型乳液(EW)、微乳液(ME)、油分散体(OD)、油悬剂(OF)、油溶性液剂(OL)、可溶性浓缩物(SL)、超低容量悬浮剂(SU)、超低容量液剂(UL)、母药(TK)、可分散性浓缩物(DC)、可湿性粉剂(WP)、可溶性颗粒剂(SG)或与农业上可接受的佐剂组合的任何技术上可行的配制品。
制备实例:
“Mp”意指以℃计的熔点。自由基表示甲基基团。在Brucker 400MHz光谱仪上记录1H NMR测量值,化学位移相对于TMS标准物以ppm给出。光谱在如指定的氘代溶剂中测量。使用以下LCMS方法中的任一种来表征化合物。每种化合物获得的特征性LCMS值是保留时间(“Rt”,以分钟记录)和测得的分子离子(M+H)+。
LC-MS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,所述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,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650l/h;质量范围:100Da至900Da)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,30x2.1mm,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,所述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,萃取器:2.00V,源温度:150℃,去溶剂化温度:350℃,锥孔气体流量:50l/h,去溶剂化气体流量:650l/h;质量范围:100Da至900Da)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,30x2.1mm,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。
实例1:N-[1-[2-[5-(三氟甲氧基)嘧啶-2-基]-1,2,4-三唑-3-基]乙基]-3,5-双
(三氟甲基)苯甲酰胺(化合物P1)的合成
在干燥的小瓶中,在氩气下,将如WO 2017192385中所描述的制备的N-[1-(2-嘧啶-2-基-1,2,4-三唑-3-基)乙基]-3,5-双(三氟甲基)苯甲酰胺(0.5478g,1.273mmol)、1-(三氟甲氧基)吡啶-4-甲腈;1,1,1-三氟-N-(三氟甲基磺酰基)甲磺酰胺(0.2g,0.4244mmol)和三(2,2′-联吡啶)六氟磷酸钌(II)(0.01824g,0.02122mmol)溶解在乙腈(12mL)中。在蓝色LED光(15W)的照射下,在室温下搅拌亮红色溶液。通过LC-MS和TLC监测反应。2小时之后,蒸发溶剂,并将粗产物通过硅胶色谱然后反相色谱纯化以得到N-[1-[2-[5-(三氟甲氧基)嘧啶-2-基]-1,2,4-三唑-3-基]乙基]-3,5-双(三氟甲基)苯甲酰胺。
1H NMR(400MHz,氯仿)δppm 1.76(d,J=6.60Hz,3H)6.37-6.48(m,1H)7.44-7.50(m,1H)8.05(s,1H)8.11(s,1H)8.28(s,2H)8.82-8.93(m,2H)。
LC-MS(方法1):515(M+H),Rt:1.06min。
实例2:N-[1-[2-[5-(2,2,2-三氟乙氧基)-2-吡啶基]-1,2,4-三唑-3-基]乙基]-
3,5-双(三氟甲基)苯甲酰胺(化合物P8)的合成
步骤1:N-[2-[(E)-二甲基氨基亚甲基氨基]-1-甲基-2-氧代-乙基]-3,5-双(三氟
甲基)苯甲酰胺的制备
在氩气下将N-(2-氨基-1-甲基-2-氧代-乙基)-3,5-双(三氟甲基)苯甲酰胺(WO2017192385中所描述的制备,14.67g,44.70mmol)吸收至二氯甲烷(90mL)中以得到淡黄色悬浮液。逐滴添加N,N-二甲基甲酰胺二甲基缩醛(9.48mL,67.05mmol)。将所得混合物在室温下搅拌18小时,并且然后使溶剂蒸发以得到N-[2-[(E)-二甲基氨基亚甲基氨基]-1-甲基-2-氧代-乙基]-3,5-双(三氟甲基)苯甲酰胺作为粗品,其无需进一步纯化即用于下一步骤。
LC-MS(方法1):384[M+H],RT:0.79min
步骤2:N-[1-[2-(5-溴-2-吡啶基)-1,2,4-三唑-3-基]乙基]-3,5-双(三氟甲基)
苯甲酰胺的制备
在氩气下将N-[2-[(E)-二甲基氨基亚甲基氨基]-1-甲基-2-氧代-乙基]-3,5-双(三氟甲基)苯甲酰胺(8.565g,22.35mmol)溶解在1,4-二噁烷(45mL)和乙酸(45mL)中。将5-溴-2-肼基吡啶(CAS:77992-44-0,5.198g,26.81mmol)分几份添加并将所得混合物在50℃下搅拌3小时。在60℃下在真空下使溶剂蒸发。将所得残余物用饱和NaHCO3水溶液和乙酸乙酯稀释。将水相用乙酸乙酯洗涤两次。将有机层合并,用水洗涤一次,用盐水洗涤一次,经无水硫代硫酸钠干燥,过滤并在60℃下在真空下浓缩。通过硅胶色谱法纯化粗品以得到N-[1-[2-(5-溴-2-吡啶基)-1,2,4-三唑-3-基]乙基]-3,5-双(三氟甲基)苯甲酰胺。
1H NMR(400MHz,CDCl3)δppm 1.74(d,J=6.60Hz,3H)6.34-6.44(m,1H)7.80(brd,J=8.07Hz,1H)7.92(d,J=8.44Hz,1H)8.01(s,1H)8.03(s,1H)8.07(dd,J=8.62,2.38Hz,1H)8.30(s,2H)8.64-8.68(m,1H)
LC-MS(方法1):510[M+H],RT:1.13min
步骤3:N-[1-[2-(5-羟基-2-吡啶基)-1,2,4-三唑-3-基]乙基]-3,5-双(三氟甲
基)苯甲酰胺的制备
在氩气下,将N-[1-[2-(5-溴-2-吡啶基)-1,2,4-三唑-3-基]乙基]-3,5-双(三氟甲基)苯甲酰胺(0.250g,0.492mmol),苯甲醛肟(0.0791g,0.0712mL,0.640mmol)和碳酸铯(0.356g,1.08mmol)溶解在N,N-二甲基甲酰胺(0.984mL)中。将所得悬浮液用氩气脱气5分钟。然后添加RockPhos Pd G3(0.0124g,0.0300)。将所得深棕色悬浮液在80℃下搅拌3天。在室温下冷却之后,添加二氯甲烷和水。将该双相悬浮液经过硅藻土过滤,并分离滤液的两个所得相。将水相用二氯甲烷洗涤一次。将经合并的有机层合并起来,用饱和NH4Cl水溶液洗涤一次,经无水Na2SO4干燥,过滤并在60℃下在真空下蒸发。通过硅胶色谱法纯化粗品以得到N-[1-[2-(5-羟基-2-吡啶基)-1,2,4-三唑-3-基]乙基]-3,5-双(三氟甲基)苯甲酰胺。
1H NMR(400MHz,DMSO)δppm 1.62(d,J=6.97Hz,3H)3.34(s,4H)5.86(t,J=6.97Hz,1H)7.40(dd,J=8.80,2.93Hz,1H)7.62(d,J=8.80Hz,1H)8.03(d,J=2.93Hz,1H)8.08(s,1H)8.31(s,1H)8.40(s,2H)9.49(d,J=7.34Hz,1H)10.39(s,1H)
LC-MS(方法1):528[M+H],Rt:1.13min
步骤4:N-[1-[2-[5-(2,2,2-三氟乙氧基)-2-吡啶基]-1,2,4-三唑-3-基]乙基]-
3,5-双(三氟甲基)苯甲酰胺的制备
在氩气下,将碳酸铯(0.056g,0.17mmol)随后2,2,2-三氟乙基三氟甲磺酸盐(0.016mL,0.11mmol)添加至N-[1-[2-(5-羟基-2-吡啶基)-1,2,4-三唑-3-基]乙基]-3,5-双(三氟甲基)苯甲酰胺(0.038g,0.085mmol)在乙腈(0.85mL)中的悬浮液。将所得混合物在室温下搅拌1小时,并且然后倒入水中。将水层用乙酸乙酯萃取两次。将有机层合并,用盐水洗涤一次,经无水硫酸钠干燥,过滤并在60℃下在真空下蒸发。通过硅胶色谱法纯化粗品以得到N-[1-[2-[5-(2,2,2-三氟乙氧基)-2-吡啶基]-1,2,4-三唑-3-基]乙基]-3,5-双(三氟甲基)苯甲酰胺。
1H NMR(400MHz,氯仿)δppm 1.72(d,J=6.60Hz,3H)4.51(q,J=8.07Hz,2H)6.25-6.41(m,1H)7.55(dd,J=9.17,2.93Hz,1H)7.87-7.94(m,1H)7.96(d,J=8.80Hz,1H)7.99(s,1H)8.03(s,1H)8.24-8.37(m,3H)
LC-MS(方法1):528[M+H],Rt:1.13min
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、吡咯衍生物、氨基甲酸酯、拟除虫菊酯、氯化烃、酰基脲、吡啶基亚甲基氨基衍生物、大环内酯、新烟碱以及苏芸金芽孢杆菌制剂。
优选具有式I的化合物与活性成分的下列混合物(其中缩写“TX”表示“选自表A-1至A-120和表P中定义的化合物中的一种化合物”):
佐剂,该佐剂选自由以下组成的物质组:石油(别名)(628)+TX,
昆虫控制活性物质,该昆虫控制活性物质选自阿维菌素+TX、灭螨醌+TX、啶虫脒+TX、乙酰虫腈+TX、氟丙菊酯+TX、Acynonapyr+TX、双丙环虫酯+TX、阿福拉纳+TX、棉铃威+TX、丙烯除虫菊酯+TX、α-氯氰菊酯+TX、甲体氯氰菊酯+TX、磺胺螨酯+TX、灭害威+TX、三唑锡+TX、杀虫磺+TX、苯螨特+TX、Benzpyrimoxan+TX、β-氟氯氰菊酯+TX、β-氯氰菊酯+TX、联苯肼酯+TX、联苯菊酯+TX、乐杀螨+TX、生物烯丙菊酯+TX、生物烯丙菊酯S)-环戊基异构体+TX、生物苄呋菊酯+TX、双三氟虫脲+TX、溴虫氟苯双酰胺(Broflanilide)+TX、溴氟菊酯+TX、溴硫磷-乙基+TX、噻嗪酮+TX、丁酮威+TX、硫线磷+TX、西维因+TX、丁硫克百威+TX、巴丹+TX,CAS号:1472050-04-6+TX、CAS号:1632218-00-8+TX、CAS号:1808115-49-2+TX、CAS号:2032403-97-5+TX、CAS号:2044701-44-0+TX、CAS号:2128706-05-6+TX、CAS号:2249718-27-0+TX、氯虫苯甲酰胺+TX、氯丹+TX、虫螨腈+TX、右旋反式氯丙炔菊酯+TX、环虫酰肼+TX、克仑吡林+TX、地虫威+TX、噻虫胺+TX、N-甲基氨基甲酸2-氯苯基酯(CPMC)+TX、苯腈膦+TX、溴氰虫酰胺+TX、环溴虫酰胺+TX、Cyclobutrifluram+TX、乙腈菊酯+TX、环氧虫啶+TX、环氧虫啶+TX、腈吡螨酯+TX、乙唑螨腈(或Etpyrafen)+TX、丁氟螨酯+TX、氟氯氰菊酯+TX、氯氟氰虫酰胺+TX、三氟氯氰菊酯+TX、氯氰菊酯+TX、苯氰菊酯+TX、环丙氨嗪+TX、溴氰菊酯+TX、丁醚脲+TX、氯亚胺硫磷+TX、二溴磷+TX、Dicloromezotiaz+TX、氟螨四嗪+TX、二氟脲+TX、嗪虫唑酰胺+TX、二活菌素+TX、敌螨普+TX、呋虫胺+TX、蔬果磷+TX、埃玛菌素+TX、烯炔菊酯+TX、ε-momfluorothrin+TX、ε-甲氧苄氟菊酯+TX、高氰戊菊酯+TX、乙硫磷+TX、乙虫腈+TX、依芬普司+TX、乙螨唑+TX、伐灭磷+TX、喹螨醚+TX、五氟苯菊酯+TX、杀螟硫磷+TX、杀螟硫磷+TX、苯硫威+TX、苯氧威+TX、甲氰菊酯+TX、唑螨酯(Fenpyroxymate)+TX、丰索磷+TX、倍硫磷+TX、三苯基乙酸锡+TX、氰戊菊酯+TX、氟虫腈+TX、Flometoquin+TX、氟啶虫酰胺+TX、嘧螨酯+TX、三氟咪啶酰胺(Fluazaindolizine)+TX、氟佐隆+TX、氟虫双酰胺+TX、氟螨噻+TX、Flucitrinate+TX、氟螨脲+TX、氟氰戊菊酯+TX、氟噻虫砜+TX、嘧虫胺+TX、三氟醚菊酯+TX、丁烯氟虫腈+TX、Fluhexafon+TX、氟氯苯菊酯+TX、氟吡菌酰胺+TX、Flupentiofenox+TX、氟吡呋喃酮+TX、Flupyrimin+TX、氟雷拉纳(Fluralaner)+TX、氟胺氰菊酯+TX、Fluxametamide+TX、噻唑膦+TX、γ-三氟氯氰菊酯+TX、GossyplureTM+TX、戊吡虫胍+TX、氯虫酰肼+TX、氯虫酰肼+TX、苄螨醚(Halofenprox)+TX、七氟甲醚菊酯(Heptafluthrin)+TX、噻螨酮+TX、氟蚁腙+TX、Imicyafos+TX、吡虫啉+TX、炔咪菊酯+TX、茚虫威+TX、碘甲烷+TX、异菌脲+TX、异噁唑虫酰胺(Isocycloseram)+TX、异拌磷+TX、伊佛霉素+TX、κ-联苯菊酯+TX、κ-七氟菊酯+TX、λ-三氟氯氰菊酯+TX、雷皮菌素+TX、氯芬奴隆+TX、氰氟虫腙+TX、四聚乙醛+TX、威百亩+TX、灭多虫+TX、甲氧虫酰肼+TX、甲氧苄氟菊酯+TX、速灭威+TX、兹克威+TX、弥拜菌素+TX、Momfluorothrin+TX、氯硝柳胺+TX、烯啶虫胺+TX、硝乙脲噻唑+TX、氧化乐果+TX、草氨酰+TX、Oxazosufyl+TX、乙基对硫磷+TX、苄氯菊酯+TX、苯醚菊酯+TX、磷虫威+TX、胡椒基丁醚(Piperonylbutoxide)+TX、抗蚜威+TX、乙基虫螨磷+TX、多角体病毒+TX、炔丙菊酯+TX、丙溴磷+TX、丙溴磷+TX、丙氟菊酯+TX、克螨特+TX、烯虫磷+TX、残杀威+TX、丙硫磷+TX、丙苯烃菊酯(Protrifenbute)+TX、Pyflubumide+TX、吡蚜酮+TX、吡唑硫磷+TX、Pyrafluprole+TX、哒螨灵+TX、啶虫丙醚+TX、氟虫吡喹(Pyrifluquinazon)+TX、嘧螨醚+TX、Pyrimostrobin+TX、吡啶氟虫腈(Pyriprole)+TX、吡丙醚+TX、苄呋菊脂+TX、沙罗拉纳(Sarolaner)+TX、西拉菌素+TX、氟硅菊酯+TX、乙基多杀菌素+TX、多杀菌素+TX、螺螨酯+TX、螺甲螨酯+TX、甲氧哌啶乙酯(Spiropidion)+TX、螺虫乙酯+TX、氟啶虫胺腈+TX、虫酰肼+TX、吡螨胺+TX、提布嘧啶磷(Tebupirimiphos)+TX、七氟菊酯+TX、硫甲双磷+TX、Tetrachloraniliprole+TX、三氯杀螨砜(Tetradiphon)+TX、胺菊酯+TX、四氟醚菊酯+TX、杀螨素+TX、氟氰虫酰胺+TX、θ-氯氰菊酯+TX、噻虫啉+TX、噻虫嗪+TX、杀虫环+TX、硫双威+TX、己酮肟威+TX、甲基乙拌磷+TX、Thiosultap+TX、Tioxazafen+TX、唑虫酰胺+TX、毒杀芬+TX、四溴菊酯+TX、四氟苯菊酯+TX、唑蚜威+TX、三唑磷+TX、敌百虫+TX、毒壤磷+TX、敌百虫+TX、三氟苯嘧啶+TX、Tyclopyrazoflor+TX、ζ-氯氰菊酯+TX、海藻提取物和衍生自甘糖酰的发酵产物+TX、海藻提取物和衍生自包含脲的糖酰的发酵产物+TX、氨基酸+TX、钾、钼和EDTA螯合的锰+TX、海藻提取物和发酵的植物产品+Tx、海藻提取物和包含植物激素的发酵的植物产品+TX、维生素+TX、EDTA-螯合的铜+Tx、锌+TX、以及铁+TX、印楝素+TX、芽孢杆菌aizawai(Bacillusaizawai)+TX、角质孢子芽孢杆菌(Bacillus chitinosporus)AQ746(NRRL登记号B-21 618)+TX、坚强芽孢杆菌(Bacillus firmus)+TX、芽孢杆菌kurstaki(Bacillus kurstaki)+TX、蕈状芽孢杆菌(Bacillus mycoides)AQ726(NRRL登记号B-21664)+TX、短小芽胞杆菌(Bacillus pumilus)(NRRL登记号B-30087)+TX、短小芽胞杆菌(Bacillus pumilus)AQ717(NRRL登记号B-21662)+TX、芽孢杆菌属(Bacillus sp.)AQ178(ATCC登记号53522)+TX、芽孢杆菌属(Bacillus sp.)AQ175(ATCC登记号55608)+TX、芽孢杆菌物种(Bacillus sp.)AQ177(ATCC登记号55609)+TX、未指定的枯草芽孢杆菌(Bacillus subtilis unspecified)+TX、枯草芽孢杆菌(Bacillus subtilis)AQ153(ATCC登记号55614)+TX、枯草芽孢杆菌(Bacillus subtilis)AQ30002(NRRL登记号B-50421)+TX、枯草芽孢杆菌(Bacillussubtilis)AQ30004(NRRL登记号B-50455)+TX、枯草芽孢杆菌(Bacillus subtilis)AQ713(NRRL登记号B-21661)+TX、枯草芽孢杆菌(Bacillus subtilis)AQ743(NRRL登记号B-21665)+TX、苏云金芽孢杆菌(Bacillus thuringiensis)AQ52(NRRL登记号B-21619)+TX、苏云金芽孢杆菌(Bacillus thuringiensis)BD#32(NRRL登记号B-21530)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subspec.kurstaki)BMP 123+TX、球孢白僵菌(Beauveria bassiana)+TX、D-柠檬烯+TX、颗粒体病毒(Granulovirus)+TX、超敏蛋白(Harpin)+TX、棉铃虫核型多角体病毒+TX、美洲棉铃虫(Helicoverpa zea)核型多角体病毒+TX、烟芽夜蛾核型多角体病毒+TX、澳洲棉铃虫核型多角体病毒+TX、绿僵菌物种(Metarhizium spp.)+TX、Muscodor albus 620(NRRL登记号30547)+TX、Muscodor roseusA3-5(NRRL登记号30548)+TX、印楝树基产品+TX、玫烟色拟青霉(Paecilomycesfumosoroseus)+TX、淡紫色拟青霉(Paecilomyces lilacinus)+TX、拟斯扎瓦巴斯德杆菌(Pasteuria nishizawae)+TX、穿刺巴斯德杆菌(Pasteuria penetrans)+TX、分支巴斯德杆菌(Pasteuria ramosa)+TX、Pasteuria thornei+TX、杀虫剂巴氏杆菌(Pasteuria usgae)+TX、对伞花烃+TX、小菜蛾颗粒体病毒(Plutella xylostella Granulosis virus)+TX、小菜蛾核型多角体病毒+TX、多角体病毒+TX、除虫菊+TX、QRD 420(类萜共混物)+TX、QRD452(类萜共混物)+TX、QRD 460(类萜共混物)+TX、皂树(Quillaja saponaria)+TX、球状红球菌(Rhodococcus globerulus)AQ719(NRRL登记号B-21663)+TX、草地贪夜蛾核型多角体病毒+TX、鲜黄链霉菌(Streptomyces galbus)(NRRL登记号30232)+TX、链霉菌物种(Streptomyces sp.)(NRRL登记号B-30145)+TX、类萜共混物+TX、以及轮枝菌物种(Verticillium spp.),
杀藻剂,该杀藻剂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,该驱蠕虫剂选自由以下组成的物质组:阿巴美丁(1)+TX、克芦磷酯(1011)+TX、Cyclobutrifluram+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,该杀鸟剂选自由以下组成的物质组:氯醛糖(127)+TX、异狄氏剂(1122)+TX、倍硫磷(346)+TX、吡啶-4-胺(IUPAC名称)(23)和士的宁(745)+TX,
杀细菌剂,该杀细菌剂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,该生物试剂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(Aphelinus abdominalis)(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(Bacillussphaericus Neide)(学名)(49)+TX、苏云金芽孢杆菌(Bacillus thuringiensisBerliner)(学名)(51)+TX、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensissubsp.aizawai)(学名)(51)+TX、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensissubsp.israelensis)(学名)(51)+TX、苏云金芽孢杆菌日本亚种(Bacillus thuringiensissubsp.japonensis)(学名)(51)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillusthuringiensis 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(Beauveriabassiana)(别名)(53)+TX、布氏白僵菌(Beauveria brongniartii)(别名)(54)+TX、普通草蛉(Chrysoperla carnea)(别名)(151)+TX、孟氏隐唇瓢虫(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(Diglyphus isaea)(别名)(254)+TX、丽蚜小蜂(Encarsiaformosa)(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(Leptomastix dactylopii)(别名)(488)+TX、盲蝽(Macrolophuscaliginosus)(别名)(491)+TX、甘蓝夜蛾NPV(别名)(494)+TX、黄阔柄跳小蜂(Metaphycushelvolus)(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(Neodiprion sertifer)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(Paecilomycesfumosoroseus)(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(Spodoptera exigua multicapsid nuclear polyhedrosisvirus)(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、Steinernema riobravis(别名)(742)+TX、蝼蛄斯氏线虫(Steinernemascapterisci)(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(Verticillium lecanii)(别名)(848)+TX,
土壤消毒剂,该土壤消毒剂选自由以下组成的物质组:碘甲烷(IUPAC名称)(542)和溴甲烷(537)+TX,
化学不育剂,该化学不育剂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(methyl apholate)[CCN]+TX、不孕啶(morzid)[CCN]+TX、氟幼脲(penfluron)(别名)[CCN]+TX、涕巴(tepa)[CCN]+TX、硫代六甲磷(thiohempa)(别名)[CCN]+TX、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,该昆虫信息素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,该昆虫驱避剂选自由以下组成的物质组:2-(辛基硫代)乙醇(IUPAC名称)(591)+TX、避蚊酮(butopyronoxyl)(933)+TX、丁氧基(聚丙二醇)(936)+TX、己二酸二丁酯(IUPAC名称)(1046)+TX、邻苯二甲酸二丁酯(1047)+TX、丁二酸二丁酯(IUPAC名称)(1048)+TX、避蚊胺[CCN]+TX、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,
杀软体动物剂,该杀软体动物剂选自由以下组成的物质组:二(三丁基锡)氧化物(IUPAC名称)(913)+TX、溴乙酰胺[CCN]+TX、砷酸钙[CCN]+TX、除线威(cloethocarb)(999)+TX、乙酰亚砷酸铜[CCN]+TX、硫酸铜(172)+TX、三苯锡(347)+TX、磷酸铁(IUPAC名称)(352)+TX、四聚乙醛(518)+TX、灭虫威(530)+TX、氯硝柳胺(576)+TX、氯硝柳胺-乙醇胺(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、Cyclobutrifluram+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(Myrotheciumverrucaria)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,该硝化抑制剂选自由以下组成的物质组:乙基黄原酸钾[CCN]以及氯啶(nitrapyrin)(580)+TX,
植物活化剂,该植物活化剂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,该杀鼠剂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,该增效剂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(649)+TX、增效醛(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,该动物驱避剂选自由以下组成的物质组:蒽醌(32)+TX、氯醛糖(127)+TX、环烷酸铜[CCN]+TX、王铜(171)+TX、二嗪磷(227)+TX、二环戊二烯(化学名称)(1069)+TX、双胍辛盐(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(840)+TX、环烷酸锌[CCN]和福美锌(856)+TX,
杀病毒剂,该杀病毒剂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,该创伤保护剂选自由以下组成的物质组:氧化汞(512)+TX、辛噻酮(590)和甲基托布津(802)+TX,
生物活性物质,该生物活性物质选自1,1-双(4-氯苯基)-2-乙氧基乙醇+TX、2,4-二氯苯基苯磺酸盐+TX、2-氟-N-甲基-N-1-萘乙酰胺+TX、4-氯苯基苯基砜+TX、乙酰虫腈+TX、氧涕灭威+TX、赛果+TX、果满磷+TX、胺吸磷+TX、胺吸磷草酸氢盐+TX、双甲脒+TX、杀螨特+TX、氧化砷+TX、偶氮苯+TX、偶氮磷盐+TX、苯菌灵+TX、苯噁磷(benoxafos)+TX、苯甲酸苄酯+TX、联苯吡菌胺+TX、溴灭菊酯+TX、溴烯杀+TX、溴硫磷+TX、溴螨酯+TX、噻嗪酮+TX、丁酮威+TX、丁酮砜威+TX、丁基哒螨灵+TX、多硫化钙+TX、毒杀芬+TX、氯灭杀威+TX、卡波硫磷+TX、螨蜱胺+TX、灭螨猛+TX、氯杀螨+TX、杀虫脒+TX、杀虫脒盐酸化物+TX、杀螨醇+TX、杀螨酯+TX、敌螨特+TX、乙酯杀螨醇+TX、灭螨脒(chloromebuform)+TX、灭虫隆(chloromethiuron)+TX、丙酯杀螨醇(chloropropylate)+TX、虫螨磷+TX、瓜菊酯I+TX、瓜菊酯II+TX、瓜菊酯+TX、克罗散泰+TX、蝇毒磷+TX、克罗米通+TX、克罗氧磷+TX、硫杂灵+TX、果虫磷+TX、DCPM+TX、DDT+TX、田乐磷+TX、田乐磷-O+TX、田乐磷-S+TX、甲基内吸磷+TX、内吸磷-O+TX、内吸磷-O-甲基+TX、内吸磷-S+TX、内吸磷-S-甲基+TX、内吸磷-S-甲基砜+TX、苯氟磺胺+TX、敌敌畏+TX、dicliphos+TX、除螨灵+TX、甲氟磷+TX、消螨酚+TX、dinex-diclexine+TX、敌螨普-4+TX、敌螨普-6+TX、邻敌螨消+TX、硝戊酯(dinopenton)+TX、硝辛酯(dinosulfon)+TX、硝丁酯(dinoterbon)+TX、敌噁磷+TX、二苯基砜+TX、双硫仑+TX、DNOC+TX、苯氧炔螨(dofenapyn)+TX、多拉菌素+TX、因毒磷+TX、依普菌素+TX、益果(ethoate-methyl)+TX、乙嘧硫磷+TX、抗螨唑+TX、苯丁锡(fenbutatin oxide)+TX、苯硫威+TX、吡螨胺(fenpyrad)+TX、唑螨酯+TX、胺苯吡菌酮(fenpyrazamine)+TX、芬螨酯+TX、氟硝二苯胺(fentrifanil)+TX、氟螨噻+TX、氟螨脲+TX、联氟螨+TX、氟杀螨+TX、FMC 1137+TX、伐虫脒+TX、伐虫脒盐酸化物+TX、胺甲威(formparanate)+TX、γ-HCH+TX、果绿啶+TX、苄螨醚+TX、环丙烷甲酸十六烷基酯+TX、水胺硫磷+TX、茉莉菊素I+TX、茉莉菊素II+TX、碘硫磷+TX、林丹+TX、丙螨氰+TX、灭蚜磷+TX、地安磷+TX、甲硫芬+TX、虫螨畏+TX、甲基溴+TX、速灭威+TX、兹克威+TX、米尔贝肟(milbemycinoxime)+TX、丙胺氟磷+TX、久效磷+TX、茂果+TX、莫西菌素+TX、二溴磷+TX、4-氯-2-(2-氯-2-甲基-丙基)-5-[(6-碘-3-吡啶基)甲氧基]哒嗪-3-酮+TX、氟蚁灵+TX、尼可霉素+TX、腈叉威(nitrilacarb)+TX、腈叉威1:1氯化锌配合物+TX、氧化乐果+TX、异亚砜磷(oxydeprofos)+TX、砜拌磷+TX、pp'-DDT+TX、对硫磷+TX、苄氯菊酯+TX、芬硫磷+TX、伏杀硫磷+TX、硫环磷+TX、磷胺+TX、聚氯萜烯(polychloroterpenes)+TX、浏阳霉素(polynactins)+TX、氯丙醇+TX、蜱虱威+TX、残杀威+TX、乙噻唑磷+TX、发果(prothoate)+TX、除虫菊酯I+TX、除虫菊酯II+TX、除虫菊酯+TX、哒嗪硫磷+TX、嘧硫磷(pyrimitate)+TX、喹硫磷+TX、喹硫磷+TX、R-1492+TX、甘氨硫磷+TX、鱼藤酮+TX、八甲磷+TX、克线丹(sebufos)+TX、西拉菌素+TX、苏果(sophamide)+TX、SSI-121+TX、舒非仑+TX、氟虫胺+TX、治螟磷+TX、硫+TX、氟螨嗪+TX、τ-氟胺氰菊酯+TX、TEPP+TX、terbam+TX、四氯杀螨砜+TX、杀螨好+TX、thiafenox+TX、抗虫威+TX、久效威+TX、甲基乙拌磷+TX、克杀螨+TX、苏云金素(thuringiensin)+TX、威菌磷+TX、苯螨噻+TX、三唑磷+TX、triazuron+TX、trifenofos+TX、三活菌素+TX、蚜灭磷+TX、vaniliprole+TX、bethoxazin+TX、二辛酸铜+TX、硫酸铜+TX、cybutryne+TX、二氯萘醌+TX、二氯芬+TX、茵多酸+TX、三苯锡(fentin)+TX、熟石灰+TX、代森钠+TX、灭藻醌+TX、quinonamid+TX、西玛嗪+TX、三苯基乙酸锡+TX、三苯基氢氧化锡+TX、育畜磷+TX、哌嗪+TX、甲基硫菌灵+TX、氯醛糖+TX、倍硫磷+TX、吡啶-4-胺+TX、毒鼠碱+TX、1-羟基-1H-吡啶-2-硫酮+TX、4-(喹喔啉-2-基氨基)苯磺酰胺+TX、8-羟基喹啉硫酸盐+TX、布罗波尔+TX、氢氧化铜+TX、甲酚+TX、双硫氧吡啶+TX、多地辛+TX、地克松+TX、甲醛+TX、萘磺汞+TX、春雷霉素+TX、盐酸春雷霉素水合物+TX、双(二甲基二硫代氨基甲酸)镍+TX、三氯甲基吡啶+TX、辛噻酮+TX、噁喹酸+TX、氧四环素+TX、羟基喹啉硫酸钾+TX、噻菌灵+TX、链霉素+TX、链霉素倍半硫酸盐+TX、叶枯酞+TX、硫柳汞钠+TX、棉褐带卷蛾GV+TX、放射形土壤杆菌(Agrobacterium radiobacter)+TX、钝绥螨物种(Amblyseius spp.)+TX、芹菜夜蛾NPV+TX、原缨翅缨小蜂(Anagrus atomus)+TX、短距蚜小蜂(Aphelinus abdominalis)+TX、阿布拉小蜂(Aphidius colemani)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)+TX、苜蓿银纹夜蛾NPV+TX、球形芽孢杆菌(Bacillussphaericus Neide)+TX、布氏白僵菌(Beauveria brongniartii)+TX、普通草蛉(Chrysoperla carnea)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)+TX、苹果小卷蛾GV+TX、西伯利亚离颚茧蜂+TX、潜蝇姬小蜂+TX、丽蚜小蜂+TX、浆角蚜小蜂+TX、嗜菌异小杆线虫和大异小杆线虫(H.megidis)+TX、斑长足瓢虫+TX、桔粉介壳虫寄生蜂(Leptomastixdactylopii)+TX、白粉虱采用盲蝽+TX、甘蓝夜蛾NPV+TX、Metaphycus helvolus+TX、金龟子绿僵菌(Metarhizium anisopliae var.acridum)+TX、金龟子绿僵菌(Metarhiziumanisopliae var.acridum)+TX、松黄叶蜂NPV和红头松树叶蜂NPV+TX、小花蝽物种(Oriusspp.)+TX、玫烟色拟青霉+TX、智利小植绥螨+TX、斯氏线虫(Steinernema bibionis)+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)+TX、夜蛾斯氏线虫(Steinernema feltiae)+TX、格氏斯氏线虫(Steinernema glaseri)+TX、里约布拉维斯氏线虫(Steinernemariobrave)+TX、里约布拉维斯氏线虫(Steinernema riobravis)+TX、蝼蛄斯氏线虫(Steinernema scapterisci)+TX、斯氏线虫物种(Steinernema spp.)+TX、赤眼蜂物种(Trichogramma spp.)+TX、西方盲走螨(Typhlodromus occidentalis)+TX、蜡蚧轮枝菌(Verticillium lecanii)+TX、唑磷嗪+TX、bisazir+TX、白消安+TX、dimatif+TX、六甲嘧胺+TX、六甲磷+TX、甲基涕巴+TX、甲硫涕巴+TX、甲基唑磷嗪+TX、morzid+TX、氟幼脲+TX、涕巴+TX、thiohempa+TX、噻替哌+TX、曲他胺+TX、乌瑞替派+TX、(E)-癸-5-烯-1-基乙酸酯与(E)-癸-5-烯-1-醇+TX、(E)-乙酸十三碳-4-烯-1-基乙酸酯+TX、(E)-6-甲基庚-2-烯-4-醇+TX、(E,Z)-十四碳-4,10-二烯-1-基乙酸酯+TX、(Z)-十二碳-7-烯-1-基乙酸酯+TX、(Z)-十六碳-11-烯醛+TX、(Z)-十六碳-11-烯-1-基乙酸酯+TX、(Z)-十六碳-13-烯-11-炔-1-基乙酸酯+TX、(Z)-二十碳-13-烯-10-酮+TX、(Z)-十四碳-7-烯-1-醛+TX、(Z)-十四碳-9-烯-1-醇+TX、(Z)-十四碳-9-烯-1-基乙酸酯+TX、(7E,9Z)-十二碳-7,9-二烯-1-基乙酸酯+TX、(9Z,11E)-十四碳-9,11-二烯-1-基乙酸酯+TX、(9Z,12E)-十四碳-9,12-二烯-1-基乙酸酯+TX、14-甲基十八碳-1-烯+TX、4-甲基壬-5-醇与4-甲基壬-5-酮+TX、α-multistriatin+TX、小蠹性信息素+TX、codlelure+TX、十二碳二烯醇(codlemone)+TX、cuelure+TX、环氧十九烷+TX、十二碳-8-烯-1-基乙酸酯+TX、十二碳-9-烯-1-基乙酸酯+TX、十二碳-8+TX、10-二烯-1-基乙酸酯+TX、dominicalure+TX、4-甲基辛酸乙酯+TX、丁子香酚+TX、弗兰特林(frontalin)+TX、诱杀烯混剂(grandlure)+TX、诱杀烯混剂I+TX、诱杀烯混剂II+TX、诱杀烯混剂III+TX、诱杀烯混剂IV+TX、红蛉诱烯+TX、齿小蠹二烯醇+TX、齿小蠹烯醇+TX、japonilure+TX、三甲基二氧三环壬烷(lineatin)+TX、litlure+TX、粉纹夜蛾性诱剂+TX、诱杀酯+TX、美加特酸(megatomoic acid)+TX、甲基丁子香酚+TX、诱虫烯+TX、十八碳-2,13-二烯-1-基乙酸酯+TX、十八碳-3,13-二烯-1-基乙酸酯+TX、orfralure+TX、oryctalure+TX、ostramone+TX、诱虫环+TX、sordidin+TX、食菌甲诱醇+TX、十四碳-11-烯-1-基乙酸酯+TX、地中海实蝇引诱剂+TX、地中海实蝇引诱剂A+TX、地中海实蝇引诱剂B1+TX、地中海实蝇引诱剂B2+TX、地中海实蝇引诱剂C+TX、trunc-call+TX、2-(辛基硫基)乙醇+TX、避蚊酮+Tx、丁氧基(聚丙二醇)+TX、己二酸二丁酯+TX、邻苯二甲酸二丁酯+TX、琥珀酸二丁酯+TX、避蚊胺+TX、碳酸二甲酯+TX、邻苯二甲酸二甲酯+TX、乙基己二醇+TX、己酰胺+TX、甲基喹-丁基+TX、甲基新癸酰胺+TX、草氨酸酯+TX、派卡瑞丁+TX、1-二氯-1-硝基乙烷+TX、1,1-二氯-2,2-双(4-乙基苯基)乙烷+TX、1,2-二氯丙烷与1,3-二氯丙烯+TX、1-溴-2-氯乙烷+TX、2,2,2-三氯-1-(3,4-二氯苯基)乙酸乙酯+TX、2,2-二氯乙烯基2-乙基亚磺酰基乙基甲基磷酸酯+TX、2-(1,3-二硫戊环-2-基)苯基二甲基氨基甲酸酯+TX、2-(2-丁氧基乙氧基)硫氰酸乙酯+TX、2-(4,5-二甲基-1,3-二氧戊环-2-基)甲基氨基甲酸苯基酯+TX、2-(4-氯-3,5-二甲苯基氧基)乙醇+TX、2-氯乙烯基二乙基磷酸酯+TX、2-咪唑烷酮+TX、2-异茂酰基茚满-1,3-二酮+TX、2-甲基(丙-2-炔基)氨基苯基甲基氨基甲酸酯+TX、2-硫氰酸基乙基月桂酸酯+TX、3-溴-1-氯丙-1-烯+TX、3-甲基-1-苯基吡唑-5-基二甲基氨基甲酸酯+TX、4-甲基(丙-2-炔基)氨基-3,5-二甲苯基甲基氨基甲酸酯+TX、5,5-二甲基-3-氧代环己-1-烯基二甲基氨基甲酸酯+TX、家蝇磷+TX、丙烯腈+TX、阿耳德林+TX、阿洛氨菌素+TX、除害威+TX、α-蜕皮激素+TX、磷化铝+TX、灭害威+TX、新烟碱+TX、athidathion+TX、甲基吡啶磷+TX、苏云金芽孢杆菌δ内毒素(Bacillusthuringiensis delta endotoxins)+TX、六氟硅酸钡+TX、多硫化钡+TX、熏虫菊+TX、拜耳22/190+TX、拜耳22408+TX、β-氟氯氰菊酯+TX、β-氯氰菊酯+TX、bioethanomethrin+TX、生物氯菊酯+TX、双(2-氯乙基)醚+TX、硼砂+TX、溴苯烯磷+TX、溴-DDT+TX、合杀威+TX、畜虫威+TX、butathiofos+TX、丁酯膦+TX、砷酸钙+TX、氰化钙+TX、二硫化碳+TX、四氯化碳+TX、杀螟丹盐酸盐+TX、瑟瓦定+TX、冰片丹+TX、氯丹+TX、十氯酮+TX、氯仿+TX、氯化苦+TX、氯辛硫磷+TX、chlorprazophos+TX、顺式-灭虫菊+TX、顺式苄呋菊酯+TX、clocythrin+TX、乙酰亚砷酸铜+TX、砷酸铜+TX、油酸铜+TX、畜虫磷+TX、冰晶石+TX、CS 708+TX、苯腈膦+TX、杀螟腈+TX、环菊酯+TX、畜蜱磷+TX、右旋胺菊酯+TX、DAEP+TX、棉隆+TX、decarbofuran+TX、diamidafos+TX、异氯硫磷+TX、除线磷+TX、dicresyl+TX、环虫腈+TX、狄氏剂+TX、5-甲基吡唑-3-基磷酸二乙酯+TX、dilor+TX、四氟甲醚菊酯+TX、地麦威+TX、苄菌酯+TX、甲基毒虫畏+TX、敌蝇威+TX、丙硝酚+TX、戊硝酚+TX、地乐酚+TX、苯虫醚+TX、蔬果磷+TX、dithicrofos+TX、DSP+TX、脱皮甾酮+TX、EI 1642+TX、EMPC+TX、EPBP+TX、etaphos+TX、杀虫丹+TX、甲酸乙酯+TX、二溴乙烷+TX、二氯乙烷+TX、环氧乙烷+TX、EXD+TX、皮蝇磷+TX、双乙威(fenethacarb)+TX、杀螟松+TX、fenoxacrim+TX、吡氯氰菊酯+TX、线虫磷+TX、乙基倍硫磷+TX、flucofuron+TX、丁苯硫磷+TX、福司吡酯+TX、丁硫环磷+TX、呋线威+TX、抗虫菊+TX、双胍盐+TX、双胍盐乙酸盐+TX、硫代碳酸钠+TX、苄螨醚+TX、HCH+TX、HEOD+TX、七氯(heptachlor)+TX、速杀硫磷+TX、HHDN+TX、氰化氢+TX、hyquincarb+TX、IPSP+TX、氯唑磷+TX、碳氯灵+TX、异艾氏剂+TX、异柳磷+TX、isolane+TX、稻瘟灵+TX、异噁唑磷+TX、保幼激素I+TX、保幼激素II+TX、保幼激素III+TX、氯戊环+TX、烯虫炔酯+TX、砷酸铅+TX、溴苯磷+TX、lirimfos+TX、噻唑磷+TX、m-甲基氨基甲酸枯烯酯+TX、磷化镁+TX、叠氮磷+TX、四甲磷+TX、灭蚜硫磷+TX、氯化亚汞+TX、mesulfenfos+TX、威百亩+TX、威百亩-钾+TX、威百亩-钠+TX、甲磺酰氟+TX、methocrotophos+TX、甲氧普林+TX、甲醚菊酯+TX、甲氧滴滴涕+TX、异硫氰酸甲酯+TX、三氯乙烷+TX、二氯甲烷+TX、噁虫酮+TX、灭蚁灵+TX、萘肽磷+TX、萘+TX、NC-170+TX、尼古丁+TX、硫酸尼古丁+TX、噻虫醛+TX、降烟碱+TX、O-5-二氯-4-碘苯基O-乙基硫代膦酸酯+TX、O,O-二乙基O-4-甲基-2-氧代-2H-色满-7-基硫代磷酸酯+TX、O,O-二乙基O-6-甲基-2-丙基嘧啶-4-基硫代磷酸酯+TX、O,O,O',O'-四丙基二硫代焦磷酸+TX、油酸+TX、对二氯苯+TX、甲基对硫磷+TX、五氯苯酚+TX、月桂酸五氯苯酯+TX、PH 60-38+TX、芬硫磷+TX、对氯硫磷+TX、膦+TX、甲基辛硫磷+TX、pirimetaphos+TX、聚氯二环戊二烯异构体+TX、亚砷酸钾+TX、硫氰酸钾+TX、早熟素I+TX、早熟素II+TX、早熟素III+TX、primidophos+TX、丙氟菊酯+TX、猛杀威+TX、丙硫磷+TX、定菌磷+TX、pyresmethrin+TX、苦木+TX、甲基喹硫磷+TX、quinothion+TX、雷复尼特+TX、灭虫菊+TX、鱼藤酮+TX、噻嗯菊酯+TX、鱼尼汀+TX、利阿诺定+TX、沙巴藜芦)+TX、八甲磷+TX、克线丹+TX、SI-0009+TX、蛾蝇腈+TX、亚砷酸钠+TX、氰化钠+TX、氟化钠+TX、六氟硅酸钠+TX、五氯酚钠+TX、硒酸钠+TX、硫氰酸钠+TX、磺隆(sulcofuron)+TX、磺隆-s钠+TX、磺酰氟+TX、硫丙磷+TX、焦油+TX、噻螨威+TX、TDE+TX、丁基嘧啶磷+TX、硫甲双磷+TX、环戊烯丙菊酯+TX、四氯乙烷+TX、thicrofos+TX、杀虫环+TX、杀虫环草酸氢盐+TX、虫线磷+TX、thiosultap+TX、thiosultap-钠+TX、四溴菊酯+TX、transpermethrin+TX、唑蚜威+TX、trichlormetaphos-3+TX、毒壤膦+TX、混杀威+TX、tolprocarb+TX、氯啶菌酯+TX、烯虫硫酯+TX、藜芦定+TX、藜芦碱+TX、XMC+TX、zetamethrin+TX、磷化锌+TX、zolaprofos+Tx、以及氯氟醚菊酯+TX、四氟醚菊酯+TX、双(三丁基锡)氧化物+TX、溴乙酰胺+TX、磷酸铁+TX、氯硝柳胺+TX、三丁基锡氧化物+TX、吡吗啉+TX、杀螺吗啉+TX、1,2-二溴-3-氯丙烷+TX、1,3-二氯丙烯+TX、3,4-二氯四氢噻吩1,1-二氧化物+TX、3-(4-氯苯基)-5-甲基罗丹宁+TX、5-甲基-6-硫代-1,3,5-噻二嗪烷-3-基乙酸+TX、6-异戊烯基氨基嘌呤+TX、苄氯噻唑+TX、细胞分裂素(cytokinins)+TX、DCIP+TX、糠醛+TX、isamidofos+TX、凯因庭+TX、疣孢漆斑菌组合物(Myrothecium verrucariacomposition)+TX、四氯噻吩+TX、二甲苯酚+TX、玉米素+TX、乙基黄原酸钾+TX、活化酯(acibenzolar)+TX、活化酯-S-甲基+TX、大虎杖(Reynoutria sachalinensis)提取物+TX、α-氯代醇+TX、安妥+TX、碳酸钡+TX、双鼠脲+TX、溴鼠灵+TX、溴敌隆+TX、溴鼠胺+TX、氯鼠酮+TX、胆钙化醇(cholecalciferol)+TX、氯杀鼠灵+TX、克灭鼠+TX、杀鼠醚+TX、杀鼠嘧啶+TX、鼠得克(difenacoum)+TX、噻鼠灵+TX、敌鼠+TX、钙化醇(ergocalciferol)+TX、氟鼠灵+TX、氟乙酰胺+TX、氟鼠啶+TX、盐酸氟鼠啶+TX、鼠特灵+TX、毒鼠磷+TX、磷+TX、杀鼠酮+TX、pyrinuron+TX、海葱葡苷(scilliroside)+TX、氟乙酸钠+TX、硫酸铊+TX、华法林+TX、胡椒酸2-(2-丁氧基乙氧基)乙酯+TX、5-(1,3-苯并间二氧杂环戊烯-5-基)-3-己基环己-2-烯酮+TX、法尼醇与橙花叔醇+TX、增效炔醚(verbutin)+TX、MGK 264+TX、增效醚(piperonylbutoxide)+TX、增效醛+TX、增效酯(propyl isomer)+TX、S421+TX、增效菊+TX、芝麻酚林(sesasmolin)+TX、亚砜+TX、蒽醌+TX、环烷酸铜+TX、氯氧化铜+TX、双环戊二烯+TX、福美双+TX、环烷酸锌+TX、福美锌+TX、衣马宁(imanin)+TX、利巴韦林+TX、氧化汞+TX、甲基硫菌灵+TX、阿扎康唑+TX、联苯三唑醇+TX、糠菌唑+TX、环丙唑醇+TX、苯醚甲环唑+TX、烯唑醇+TX、氟环唑+TX、腈苯唑+TX、氟喹唑+TX、氟硅唑+TX、粉唑醇+TX、呋吡菌胺+TX、己唑醇+TX、抑霉唑+TX、亚胺唑+TX、种菌唑+TX、叶菌唑+TX、腈菌唑+TX、多效唑(paclobutrazole)+TX、戊菌唑+TX、戊菌唑+TX、丙硫菌唑+TX、啶斑肟+TX、咪鲜胺(prochloraz)+TX、丙环唑+TX、啶菌噁唑+TX、硅氟唑+TX、戊唑醇+TX、氟醚唑+TX、三唑酮+TX、三唑醇+TX、氟菌唑+TX、灭菌唑+TX、嘧啶醇+TX、氯苯嘧啶醇+TX、氟苯嘧啶醇+TX、磺酸丁嘧啶+TX、二甲嘧酚+TX、乙嘧酚+TX、吗菌灵+TX、苯锈啶+TX、丁苯吗啉+TX、螺环菌胺+TX、克啉菌+TX、嘧菌环胺+TX、嘧菌胺+TX、嘧霉胺+TX、拌种咯(fenpiclonil)+TX、咯菌腈+TX、苯霜灵(benalaxyl)+TX、furalaxyl+TX、甲霜灵+TX、R-甲霜灵+TX、ofurace+TX、噁霜灵+TX、多菌灵+TX、咪菌威(debacarb)+TX、麦穗宁+TX、噻菌灵+TX、乙菌利+TX、菌核利+TX、甲菌利(myclozoline)+TX、腐霉利+TX、乙烯菌核利+TX、啶酰菌胺+TX、萎锈灵+TX、甲呋酰胺+TX、氟酰胺+TX、灭锈胺+TX、氧化萎锈灵+TX、吡噻菌胺+TX、噻呋酰胺+TX、多果定+TX、双胍辛胺+TX、嘧菌酯+TX、醚菌胺+TX、烯肟菌酯+TX、烯肟菌胺+TX、氟菌螨酯+TX、氟嘧菌酯+TX、甲氧胺菌灵+TX、苯氧菌胺+TX、肟菌酯+TX、肟醚菌胺+TX、啶氧菌酯+TX、唑菌胺酯+TX、唑胺菌酯+TX、唑菌酯+TX、福美铁+TX、代森锰锌(mancozeb)+TX、代森锰(maneb)+TX、代森联+TX、甲基代森锌+TX、代森锌+TX、敌菌丹+TX、克菌丹+TX、唑呋草+TX、灭菌丹+TX、对甲抑菌灵+TX、波尔多混合剂+TX、氧化铜+TX、代森猛铜(mancopper)+TX、喹啉铜+TX、酞菌酯(nitrothal-isopropyl)+TX、克瘟散+TX、iprobenphos+TX、phosdiphen+TX、甲基立枯磷+TX、防霉灵+TX、苯噻菌胺(benthiavalicarb)+TX、灰瘟素-S+TX、地茂散+TX、百菌清+TX、环氟菌胺+TX、霜脲氰+TX、Cyclobutrifluram+TX、双氯氰菌胺+TX、哒菌酮+TX、氯硝胺+TX、乙霉威+TX、达灭芬+TX、氟吗啉+TX、二噻农+TX、噻唑菌胺+TX、土菌灵+TX、噁唑菌酮+TX、咪唑菌酮+TX、氰菌胺+TX、嘧菌腙+TX、氟啶胺+TX、flubeneteram+TX;氟吡菌胺+TX、磺菌胺+TX、氟唑菌酰胺+TX、环酰菌胺+TX、三乙膦酸铝+TX、噁霉灵+TX、丙森锌+TX、氰霜唑+TX、磺菌威+TX、苯菌酮+TX、戊菌隆+TX、苯酞+TX、多抗霉素+TX、霜霉威+TX、吡菌苯威+TX、丙氧喹啉+TX、咯喹酮+TX、pyriofenone+TX、喹氧灵+TX、喹硫磷+TX、噻酰菌胺+TX、咪唑嗪+TX、三环唑+TX、嗪氨灵+TX、有效霉素+TX、缬菌胺+TX、苯酰菌胺+TX、双炔酰菌胺+TX、吡唑萘菌胺+TX、氟唑环菌胺+TX、苯并烯氟菌唑+TX、氟唑菌酰羟胺+TX、3-二氟甲基-1-甲基-1H-吡唑-4-羧酸(3',4',5'-三氟-联苯-2-基)-酰胺+TX、isoflucypram+TX、异噻菌胺(isotianil)+TX、dipymetitrone+TX、6-乙基-5,7-二氧代-吡咯并[4,5][1,4]二噻吩并[1,2-c]异噻唑-3-甲腈+TX、2-(二氟甲基)-N-[3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+TX、4-(2,6-二氟苯基)-6-甲基-5-苯基-哒嗪-3-甲腈+TX、(R)-3-(二氟甲基)-1-甲基-N-[1,1,3-三甲基茚满-4-基]吡唑-4-甲酰胺+TX、4-(2-溴-4-氟-苯基)-N-(2-氯-6-氟-苯基)-2,5-二甲基-吡唑-3-胺+TX、4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺+TX、fluindapyr+TX、甲香菌酯(甲香菌酯(jiaxiangjunzhi))+TX、lvbenmixianan+TX、dichlobentiazox+TX、mandestrobin+TX、3-(4,4-二氟-3,4-二氢-3,3-二甲基异喹啉-1-基)喹诺酮+TX、2-[2-氟-6-[(8-氟-2-甲基-3-喹啉基)氧基]苯基]丙-2-醇+TX、氟噻唑吡乙酮(oxathiapiprolin)+TX、N-[6-[[[(1-甲基四唑-5-基)-苯基-亚甲基]氨基]氧甲基]-2-吡啶基]氨基甲酸叔丁酯+TX、联苯吡嗪菌胺(pyraziflumid)+TX、inpyrfluxam+TX、trolprocarb+TX、氯氟醚菌唑(mefentrifluconazole)+TX、ipfentrifluconazole+TX、2-(二氟甲基)-N-[(3R)-3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+TX、N'-(2,5-二甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒+TX、N'-[4-(4,5-二氯噻唑-2-yl)氧基-2,5-二甲基-苯基]-N-乙基-N-甲基-甲脒+TX、[2-[3-[2-[1-[2-[3,5-双(二氟甲基)吡唑-1-基]乙酰基]-4-哌啶基]噻唑-4-基]-4,5-二氢异噁唑-5-yl]-3-氯-苯基]甲磺酸酯+TX、N-[6-[[(Z)-[(1-甲基四唑-5-基)-苯基-亚甲基]氨基]氧甲基]-2-吡啶基]氨基甲酸丁-3-炔酯+TX、N-[[5-[4-(2,4-二甲基苯基)三唑-2-基]-2-甲基-苯基]甲基]氨基甲酸甲酯+TX、3-氯-6-甲基-5-苯基-4-(2,4,6-三氟苯基)哒嗪+TX、pyridachlometyl+TX、3-(二氟甲基)-1-甲基-N-[1,1,3-三甲基色满-4-基]吡唑-4-甲酰胺+TX、1-[2-[[1-(4-氯苯基)吡唑-3-基]氧甲基]-3-甲基-苯基]-4-甲基-四唑-5-酮+TX、1-甲基-4-[3-甲基-2-[[2-甲基-4-(3,4,5-三甲基吡唑-1-基)苯氧基]甲基]苯基]四唑-5-酮+TX、aminopyrifen+TX、唑嘧菌胺+TX、安美速+TX、氟唑菌苯胺+TX、(Z,2E)-5-[1-(4-氯苯基)吡唑-3-基]氧基-2-甲氧基亚胺基-N,3-二甲基-戊-3-烯酰胺+TX、吡啶菌酰胺(florylpicoxamid)+TX、fenpicoxamid+TX、tebufloquin+TX、ipflufenoquin+TX、quinofumelin+TX、异丙噻菌胺+TX、N-[2-[2,4-二氯-苯氧基]苯基]-3-(二氟甲基)-1-甲基-吡唑-4-甲酰胺+TX、N-[2-[2-氯-4-(三氟甲基)苯氧基]苯基]-3-(二氟甲基)-1-甲基-吡唑-4-甲酰胺+TX、苯噻菌酯+TX、氰烯菌酯+TX、5-氨基-1,3,4-噻二唑-2-硫醇锌盐(2:1)+TX、氟吡菌酰胺+TX、flutianil+TX、fluopimomide+TX、pyrapropoyne+TX、picarbutrazox+TX、2-(二氟甲基)-N-(3-乙基-1,1-二甲基-茚满-4-基)吡啶-3-甲酰胺+TX、2-(二氟甲基)-N-((3R)-1,1,3-三甲基茚满-4-基)吡啶-3-甲酰胺+TX、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苄腈+TX、metyltetraprole+TX、2-(二氟甲基)-N-((3R)-1,1,3-三甲基茚满-4-基)吡啶-3-甲酰胺+TX、α-(1,1-二甲基乙基)-α-[4'-(三氟甲氧基)[1,1'-联苯]-4-基]-5-嘧啶甲醇+TX、fluoxapiprolin+TX、enoxastrobin+TX、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苄腈+TX、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-磺酰基-1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苄腈+TX、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-硫代-4H-1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苄腈+TX、抗倒酯+TX、丁香菌酯+TX、中生菌素+TX、噻菌铜+TX、噻唑锌+TX、amectotractin+TX、异菌脲+TX、(N-甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]环丙基甲酰胺的混合物+TX、N,2-二甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]丙基]甲基]丙酰胺+TX、N-乙基-2-甲基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺+TX、1-甲氧基-3-甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲+TX、1,3-二甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲+TX、3-乙基-1-甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲+TX、N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺+TX、4,4-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮+TX、5,5-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮+TX、1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]吡唑-4-甲酸乙酯+TX、以及N,N-二甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]-1,2,4-三唑-3-胺+TX)(其中混合物中的化合物除了TX之外可以由WO 2017/055473、WO2017/055469、WO 2017/093348和WO 2017/118689中所描述的方法制备)、2-[6-(4-氯苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇+TX(该化合物可以由WO2017/029179中所描述的方法制备)、2-[6-(4-溴苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇+TX(该化合物可以由WO 2017/029179中所描述的方法制备)、3-[2-(1-氯环丙基)-3-(2-氟苯基)-2-羟基-丙基]咪唑-4-甲腈+TX(该化合物可以由WO2016/156290中所描述的方法制备)、3-[2-(1-氯环丙基)-3-(3-氯-2-氟-苯基)-2-羟基-丙基]咪唑-4-甲腈+TX(该化合物可以由WO2016/156290中所描述的方法制备)、2-氨基-6-甲基-吡啶-3-甲酸(4-苯氧基苯基)甲酯+TX(该化合物可以由WO 2014/006945中所描述的方法制备)、2,6-二甲基-1H,5H-[1,4]二噻吩并[2,3-c:5,6-c']二吡咯-1,3,5,7(2H,6H)-四酮+TX(该化合物可以由WO 2011/138281中所描述的方法制备)、N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]硫代苯甲酰胺+TX、N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺+TX、
(Z,2E)-5-[1-(2,4-二氯苯基)吡唑-3-基]氧基-2-甲氧基亚氨基-N,3-二甲基-戊-3-烯胺+TX(该化合物可以由WO 2018/153707中描述的方法制备)、N'-(2-氯-5-甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒+TX、N'-[2-氯-4-(2-氟苯氧基)-5-甲基-苯基]-N-乙基-N-甲基-甲脒+TX(该化合物可以由WO 2016/202742中描述的方法制备)、以及2-(二氟甲基)-N-[(3S)-3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+TX(该化合物可以由WO2014/095675中描述的方法制备),
微生物,包括:鲁氏不动杆菌(Acinetobacter lwoffii)+TX、支顶孢菌(Acremonium alternatum)+TX+TX、顶头孢霉(Acremonium cephalosporium)+TX+TX、柿萎凋病菌(Acremonium diospyri)+TX、Acremonium obclavatum+TX、棉褐带卷蛾颗粒体病毒(Adoxophyes orana granulovirus)(AdoxGV)+TX、放射形土壤杆菌(Agrobacterium radiobacter)菌株K84+TX、链格孢菌(Alternariaalternate)+TX、决明链格孢菌(Alternaria cassia)+TX、损毁链格孢菌(Alternariadestruens)+TX、白粉寄生孢(Ampelomyces quisqualis)+TX、黄曲霉菌(Aspergillus flavus)AF36+TX、黄曲霉菌(Aspergillusflavus)NRRL 21882+TX、曲霉菌物种(Aspergillus spp.)+TX、出芽短梗霉菌(Aureobasidium pullulans)+TX、固氮螺菌(Azospirillum)+TX、(+TX、TAZO)+TX、固氮菌(Azotobacter)+TX、Azotobacter chroocuccum+TX、囊肿固氮菌(Azotobacter cysts)(Bionatural Blooming)+TX、解淀粉芽孢杆菌(Bacillus amyloliquefaciens)+TX、蜡样芽胞杆菌(Bacillus cereus)+TX、角质孢子芽孢杆菌(Bacillus chitinosporus)菌株CM-1+TX、角质孢子芽孢杆菌(Bacilluschitinosporus)菌株AQ746+TX、地衣芽孢杆菌(Bacillus licheniformis)菌株HB-2(BiostartTM )+TX、地衣芽孢杆菌(Bacillus licheniformis)菌株3086(+TX、Green)+TX、环状芽胞杆菌(Bacillus circulans)+TX、坚强芽孢杆菌(Bacillus firmus)(+TX、BioNem-+TX、)+TX、坚强芽孢杆菌(Bacillus firmus)菌株I-1582+TX、浸麻芽孢杆菌(Bacillus macerans)+TX、死海芽孢杆菌(Bacillus marismortui)+TX、巨大芽孢杆菌(Bacillus megaterium)+TX、蕈状芽孢杆菌(Bacillus mycoides)菌株AQ726+TX、乳突芽孢杆菌(Bacillus papillae)(Milky Spore)+TX、短小芽胞杆菌物种(Bacillus pumilus spp.)+TX、短小芽胞杆菌(Bacillus pumilus)菌株GB34(Yield)+TX、短小芽胞杆菌(Bacilluspumilus)菌株AQ717+TX、短小芽胞杆菌(Bacillus pumilus)菌株QST 2808(+TX、Ballad)+TX、Bacillus spahericus+TX、芽胞杆菌物种(Bacillus spp.)+TX、芽胞杆菌物种(Bacillus spp.strain)菌株AQ175+TX、芽胞杆菌物种(Bacillus spp.)菌株AQ177+TX、芽胞杆菌物种(Bacillus spp.)菌株AQ178+TX、枯草芽孢杆菌(Bacillus subtilis)菌株QST 713(+TX、+TX、)+TX、枯草芽孢杆菌(Bacillus subtilis)菌株QST 714+TX、枯草芽孢杆菌(Bacillus subtilis)菌株AQ153+TX、枯草芽孢杆菌(Bacillus subtilis)菌株AQ743+TX、枯草芽孢杆菌(Bacillus subtilis)菌株QST3002+TX、枯草芽孢杆菌(Bacillus subtilis)菌株QST3004+TX、解淀粉枯草芽孢杆菌变种(Bacillus subtilisvar.amyloliquefaciens)菌株FZB24(+TX,)+TX、苏云金芽胞杆菌(Bacillus thuringiensis)Cry 2Ae+TX、苏云金芽胞杆菌(Bacillus thuringiensis)Cry1Ab+TX、苏云金芽胞杆菌鲇泽亚种(Bacillus thuringiensis aizawai)GC 91+TX、苏云金芽胞杆菌以色列亚种(Bacillus thuringiensis israelensis)(+TX、+TX、)+TX、苏云金芽胞杆菌库尔斯塔克亚种(Bacillus thuringiensis kurstaki)(+TX、+TX、+TX、+TX、Scutella+TX、Turilav+TX、+TX、Dipel+TX、+TX、)+TX、苏云金芽胞杆菌库尔斯塔克亚种(Bacillusthuringiensis kurstaki)BMP 123+TX、苏云金芽胞杆菌库尔斯塔克亚种(Bacillus thuringiensis kurstaki)HD-1(Bioprotec-)+TX、苏云金芽胞杆菌(Bacillus thuringiensis)菌株BD#32+TX、苏云金芽胞杆菌(Bacillus thuringiensis)菌株AQ52+TX、苏云金芽胞杆菌鲇泽亚种(Bacillus thuringiensis aizawai)(+TX、)+TX、细菌物种(bacteria spp.)(+TX、+TX、)+TX、Clavipacter michiganensis噬菌体+TX、+TX、白僵菌(Beauveria bassiana)(+TX、Brocaril)+TX、白僵菌(Beauveria bassiana)GHA(Mycotrol+TX、Mycotrol+TX、)+TX、布氏白僵菌(Beauveria brongniartii)(+TX、Schweizer+TX、)+TX、白僵菌物种(Beauveria spp.)+TX、灰霉孢菌(Botrytis cineria)+TX、慢生型大豆根瘤菌(Bradyrhizobium japonicum)+TX、短短芽孢杆菌(Brevibacillusbrevis)+TX、苏云金芽胞杆菌拟步行甲亚种(Bacillus thuringiensis tenebrionis)+TX、BtBooster+TX、洋葱伯克霍尔德菌(Burkholderia cepacia)(+TX、+TX、Blue)+TX、伯克霍尔德菌(Burkholderiagladii)+TX、唐菖蒲伯克霍尔德菌(Burkholderia gladioli)+TX、伯克霍尔德菌属物种(Burkholderia spp.)+TX、加拿大蓟真菌(Canadian thistle fungus)(CBH Canadian)+TX、乳酪假丝酵母(Candida butyri)+TX、无名假丝酵母(Candidafamata)+TX、Candida fructus+TX、光滑念珠菌(Candida glabrata)+TX、吉利蒙念珠菌(Candida guilliermondii)+TX、口津假丝酵母(Candida melibiosica)+TX、橄榄假丝酵母(Candida oleophila)菌株O+TX、近平滑假丝酵母(Candida parapsilosis)+TX、菌膜假丝酵母(Candida pelliculosa)+TX、铁红假丝酵母(Candida pulcherrima)+TX、瑞氏假丝酵母(Candida reukaufii)+TX、齐藤假丝酵母(Candida saitoana)(Bio-+TX、)+TX、清酒假丝酵母(Candida sake)+TX、假丝酵母属物种(Candida spp.)+TX、纤细假丝酵母(Candida tenius)+TX、戴氏西地西菌(Cedecea dravisae)+TX、产黄纤维单胞菌(Cellulomonas flavigena)+TX、螺卷毛壳(Chaetomium cochliodes)(Nova-)+TX、球毛壳菌(Chaetomium globosum)(Nova-)+TX、铁杉紫色杆菌(Chromobacterium subtsugae)菌株PRAA4-1T+TX、枝状枝孢菌(Cladosporium cladosporioides)+TX、尖孢枝孢(Cladosporium oxysporum)+TX、绿头枝孢(Cladosporium chlorocephalum)+TX、枝孢属物种(Cladosporium spp.)+TX、极细枝孢霉(Cladosporium tenuissimum)+TX、粉红粘帚霉(Clonostachys rosea)+TX、尖孢炭疽菌(Colletotrichum acutatum)+TX、盾壳霉(Coniothyrium minitans)(Cotans)+TX、盾壳霉属物种(Coniothyrium spp.)+TX、浅白隐球酵母(Cryptococcus albidus)+TX、土生隐球菌(Cryptococcus humicola)+TX、隐球酵母属(Cryptococcus infirmo-miniatus)+TX、罗伦隐球酵母(Cryptococcus laurentii)+TX、苹果异形小卷蛾颗粒体病毒(Cryptophlebialeucotreta granulovirus)+TX、Cupriavidus campinensis+TX、苹果蠹蛾颗粒体病毒(Cydia pomonella granulovirus)(CYD-)+TX、苹果蠹蛾颗粒体病毒(Cydia pomonella granulovirus)(+TX、Madex+TX、Madex)+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(Enterobacter cloacae)+TX、肠杆菌科(Enterobacteriaceae)+TX、毒力虫霉(Entomophtora virulenta)+TX、附球菌(Epicoccum nigrum)+TX、黑附球菌(Epicoccum purpurascens)+TX、附球孢属物种(Epicoccum spp.)+TX、Filobasidium floriforme+TX、锐顶镰孢菌(Fusariumacuminatum)+TX、厚孢镰刀菌(Fusarium chlamydosporum)+TX、尖孢镰刀菌(Fusariumoxysporum)+TX、层出镰刀菌(Fusarium proliferatum)+TX、镰刀菌属物种(Fusarium spp.)+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(Gliocladium spp.)+TX、绿粘帚霉(Gliocladium virens)+TX、颗粒体病毒(Granulovirus)+TX、Halobacillus halophilus+TX、Halobacillus litoralis+TX、嗜盐盐芽孢杆菌(Halobacillus trueperi)+TX、盐单胞菌属物种(Halomonas spp.)+TX、冰下盐单胞菌(Halomonas subglaciescola)+TX、多变盐弧菌(Halovibrio variabilis)+TX、葡萄汁有孢汉逊酵母(Hanseniaspora uvarum)+TX、棉铃虫核型多角体病毒(Helicoverpaarmigera nucleopolyhedrovirus)+TX、谷实夜蛾核型多角体病毒(Helicoverpa zea nuclear polyhedrosis virus)+TX、异黄酮-芒柄花黄素(Isoflavone-formononetin)+TX、柠檬克勒克酵母(Kloeckeraapiculata)+TX、克勒克酵母属物种(Kloeckera spp.)+TX、大链壶菌(Lagenidiumgiganteum)+TX、长孢蜡蚧菌(Lecanicillium longisporum)+TX、蝇蚧疥霉(Lecanicillium muscarium)+TX、舞毒蛾核型多角体病毒(Lymantria Dispar nucleopolyhedrosis virus)+TX、嗜盐海球菌(Marinococcus halophilus)+TX、格氏梅拉菌(Meira geulakonigii)+TX、绿僵菌(Metarhizium anisopliae)+TX、绿僵菌(Metarhizium anisopliae)(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(Myrothecium verrucaria)菌株AARC-0255+TX、BROS+TX、Ophiostoma piliferum菌株D97+TX、粉质拟青霉(Paecilomycesfarinosus)+TX、玫烟色拟青霉(Paecilomyces fumosoroseus)(PFR-+TX、)+TX、淡紫拟青霉(Paecilomyces linacinus)(Biostat)+TX、淡紫拟青霉(Paecilomyces lilacinus)菌株251(MeloCon)+TX、多粘类芽孢杆菌(Paenibacillus polymyxa)+TX、成团泛菌(Pantoea agglomerans)(BlightBan)+TX、泛菌属物种(Pantoea spp.)+TX、巴斯德氏芽菌属物种(Pasteuria spp.)+TX、拟斯扎瓦巴氏杆菌(Pasteuria nishizawae)+TX、黄灰青霉(Penicillium aurantiogriseum)+TX、拜赖青霉(Penicillium billai)(+TX、Tag)+TX、短密青霉(Penicillium brevicompactum)+TX、常现青霉(Penicillium frequentans)+TX、灰黄青霉(Penicillium griseofulvum)+TX、产紫青霉(Penicillium purpurogenum)+TX、青霉菌属物种(Penicillium spp.)+TX、纯绿色肯霉(Penicillium viridicatum)+TX、大伏革菌(Phlebiopsis gigantean)+TX、解磷细菌(phosphate solubilizing bacteria)+TX、隐地疫霉(Phytophthora cryptogea)+TX、棕榈疫霉(Phytophthora palmivora)+TX、异常毕赤酵母(Pichia anomala)+TX、季也蒙毕赤酵母(Pichia guilermondii)+TX、膜醭毕赤氏酵母(Pichia membranaefaciens)+TX、指甲毕赤酵母(Pichia onychis)+TX、树干毕赤酵母(Pichia stipites)+TX、铜绿假单胞菌(Pseudomonas aeruginosa)+TX、致金色假单胞菌(Pseudomonas aureofasciens)(Spot-Less)+TX、洋葱假单胞菌(Pseudomonas cepacia)+TX、绿针假单胞菌(Pseudomonas chlororaphis)+TX、皱褶假单胞菌(Pseudomonas corrugate)+TX、荧光假单胞菌(Pseudomonasfluorescens)菌株A506(BlightBan)+TX、恶臭假单胞菌(Pseudomonas putida)+TX、Pseudomonas reactans+TX、假单胞菌属物种(Pseudomonas spp.)+TX、丁香假单胞菌(Pseudomonas syringae)(Bio-)+TX、绿黄假单胞菌(Pseudomonas viridiflava)+TX、Pseudomons fluorescens+TX、Pseudozyma flocculosa菌株PF-A22UL(Sporodex)+TX、纵沟柄锈菌(Puccinia canaliculata)+TX、Puccinia thlaspeos(Wood)+TX、侧雄腐霉菌(Pythium paroecandrum)+TX、寡雄腐霉(Pythiumoligandrum)(+TX、)+TX、缠器腐霉(Pythiumperiplocum)+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(Sclerotiniaminor)+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)(Spod-+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(Streptomyces lydicus)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(Trichodermaatroviride)+TX、钩状木霉(Trichoderma hamatum)TH 382+TX、哈茨木霉(Trichoderma harzianum rifai)+TX、哈茨木霉(Trichodermaharzianum)T-22(Trianum-+TX、PlantShield+TX、+TX、Trianum-)+TX、哈茨木霉(Trichoderma harzianum)T-39+TX、非钩木霉(Trichoderma inhamatum)+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(Trichoderma longibrachiatum)+TX、多孢木霉(Trichoderma polysporum)(Binab)+TX、紫杉木霉(Trichoderma taxi)+TX、绿色木霉(Trichoderma virens)+TX、绿色木霉(Trichoderma virens)(原来称为绿色粘帚霉(Gliocladium virens)GL-21)+TX、绿色木霉(Trichoderma viride)+TX、绿色木霉(Trichodermaviride)菌株ICC080+TX、茁芽丝孢酵母(Trichosporon pullulans)+TX、毛孢子菌属物种(Trichosporon spp.)+TX、单端孢属物种(Trichothecium spp.)+TX、粉红单端孢(Trichothecium roseum)+TX、Typhula phacorrhiza菌株94670+TX、Typhulaphacorrhiza菌株94671+TX、黑细基格孢(Ulocladium atrum)+TX、奥德曼细基格孢(Ulocladium oudemansii)(Botry-)+TX、玉蜀黍黑粉菌(Ustilago maydis)+TX、各种细菌和补充微量营养素(Natural)+TX、各种真菌(Millennium)+TX、厚垣轮枝孢菌(Verticillium chlamydosporium)+TX、蜡蚧轮枝菌(Verticilliumlecanii)(+TX、)+TX、Vip3Aa20+TX、死海枝芽孢杆菌(Virgibaclillus marismortui)+TX、Xanthomonas野油菜黄单胞菌pv.(campestrispv.)Poae+TX、伯氏致病杆菌+TX、嗜线虫致病杆菌;
植物提取物,包括:松树油+TX、印楝素(Plasma Neem+TX、+TX、+TX、Molt-+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(Moss)+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
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 C-)+TX、葡萄小卷叶蛾信息素(3MMEC-GBM Sprayable)+TX、卷叶虫信息素(3MMEC–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(Isomate-)+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、Check-+TX、薰衣草千里酸酯(Lavandulyl senecioate);
宏生物剂(Macrobial),包括:短距蚜小蜂(Aphelinus abdominalis)+TX、阿尔蚜茧蜂(Aphidius ervi)(Aphelinus-)+TX、Acerophagus papaya+TX、二星瓢虫(Adalia bipunctata)(Adalia-)+TX、二星瓢虫(Adalia bipunctata)+TX、二星瓢虫(Adalia bipunctata)+TX、串茧跳小蜂(Ageniaspis citricola)+TX、巢蛾多胚跳小蜂(Ageniaspis fuscicollis)+TX、安德森钝绥螨(Amblyseius andersoni)(+TX、Andersoni-)+TX、加州钝绥螨(Amblyseius californicus)(+TX、)+TX、黄瓜钝绥螨(Amblyseius cucumeris)(+TX、Bugline)+TX、伪钝绥螨(Amblyseius fallacis)+TX、斯氏钝绥螨(Amblyseius swirskii)(Bugline+TX、Swirskii-)+TX、奥氏钝绥螨(Amblyseius womersleyi)+TX、粉虱细蜂(Amitus hesperidum)+TX、原樱翅缨小蜂(Anagrusatomus)+TX、暗腹长索跳小蜂(Anagyrus fusciventris)+TX、卡玛长索跳小蜂(Anagyruskamali)+TX、Anagyrus loecki+TX、粉蚧长索跳小蜂(Anagyrus pseudococci)+TX、红蜡蚧扁角跳小蜂(Anicetus benefices)+TX、金小蜂(Anisopteromalus calandrae)+TX、林地花蝽(Anthocoris nemoralis)(Anthocoris-)+TX、短距蚜小蜂(Aphelinus abdominalis)(+TX、)+TX、短翅蚜小蜂(Aphelinus asychis)+TX、棉蚜寄生蜂(Aphidius colemani)+TX、阿尔蚜茧蜂(Aphidius ervi)+TX、烟蚜茧蜂(Aphidius gifuensis)+TX、桃赤蚜蚜茧蜂(Aphidius matricariae)(Aphipar-)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)+TX、食蚜瘿蚊(Aphidoletesaphidimyza)+TX、岭南黄蚜小蜂(Aphytis lingnanensis)+TX、印巴黄蚜小蜂(Aphytis melinus)+TX、哈氏长尾啮小蜂(Aprostocetus hagenowii)+TX、蚁形隐翅甲(Atheta coriaria)+TX、熊蜂属物种(Bombus spp.)+TX、欧洲熊蜂(Bombus terrestris)(Natupol)+TX、欧洲熊蜂(Bombus terrestris)(+TX、)+TX、Cephalonomia stephanoderis+TX、黑背唇瓢虫(Chilocorus nigritus)+TX、普通草蛉(Chrysoperla carnea)+TX、普通草蛉(Chrysoperla carnea)+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 spp.+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(Cotesia flavipes)+TX、菜蛾绒茧蜂(Cotesiaplutellae)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(+TX、)+TX、日本方头甲(Cybocephalus nipponicus)+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)+TX、小黑瓢虫(Delphastus catalinae)+TX、Delphastus pusillus+TX、Diachasmimorpha krausii+TX、长尾潜蝇茧蜂(Diachasmimorpha longicaudata)+TX、Diaparsis jucunda+TX、阿里食虱跳小蜂(Diaphorencyrtus aligarhensis)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)(+TX、)+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)(+TX、)+TX、歧脉跳小蜂属物种(Diversinervus spp.)+TX、盾蚧长缨蚜小蜂(Encarsia citrina)+TX、丽蚜小蜂(Encarsiaformosa)(Encarsia+TX、+TX、En-)+TX、浆角蚜小蜂(Eretmocerus eremicus)+TX、哥德恩蚜小蜂(Encarsia guadeloupae)+TX、海地恩蚜小蜂(Encarsia haitiensis)+TX、细扁食蚜蝇(Episyrphus balteatus)+TX、Eretmoceris siphonini+TX、加州浆角蚜小蜂(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(Eretmocerus hayati)+TX、蒙氏桨角蚜小蜂(Eretmocerus mundus)(+TX、Eretline)+TX、Eretmocerus siphonini+TX、四斑光缘瓢虫(Exochomusquadripustulatus)+TX、食螨瘿蚊(Feltiella acarisuga)+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(Franklinothrips vespiformis)+TX、西方静走螨(Galendromusoccidentalis)+TX、莱氏棱角肿腿蜂(Goniozus legneri)+TX、麦蛾柔茧蜂(Habrobraconhebetor)+TX、异色瓢虫(Harmonia axyridis)+TX、异小杆线虫属物种(Heterorhabditis spp.)(Lawn)+TX、嗜菌异小杆线虫(Heterorhabditisbacteriophora)(NemaShield+TX、+TX、Terranem-+TX、+TX、+TX、B-+TX、+TX、)+TX、大异小杆线虫(Heterorhabditis megidis)(Nemasys+TX、BioNem+TX、Exhibitline+TX、Larvanem-)+TX、斑长足瓢虫(Hippodamiaconvergens)+TX、尖狭下盾螨(Hypoaspis aculeifer)(Aculeifer-+TX、Entomite-)+TX、兵下盾螨(Hypoaspis miles)(Hypoline+TX、Entomite-)+TX、黑色枝跗瘿蜂(Lbalia leucospoides)+TX、Lecanoideus floccissimus+TX、Lemophagus errabundus+TX、三色丽突跳小蜂(Leptomastidea abnormis)+TX、橘粉介壳虫寄生蜂(Leptomastix dactylopii)+TX、长角跳小蜂(Leptomastixepona)+TX、Lindorus lophanthae+TX、Lipolexis oregmae+TX、叉叶绿蝇(Luciliacaesar)+TX、茶足柄瘤蚜茧蜂(Lysiphlebus testaceipes)+TX、盲蝽(Macrolophus caliginosus)(Mirical-+TX、Macroline+TX、)+TX、Mesoseiulus longipes+TX、黄色阔柄跳小蜂(Metaphycus flavus)+TX、Metaphycuslounsburyi+TX、角纹脉褐蛉(Micromus angulatus)+TX、黄色花翅跳小蜂(Microterys flavus)+TX、Muscidifurax raptorellus和Spalangia cameroni+TX、Neodryinus typhlocybae+TX、加州新小绥螨(Neoseiuluscalifornicus)+TX、黄瓜新小绥螨(Neoseiulus cucumeris)+TX、伪新小绥螨(Neoseiulus fallacis)+TX、Nesideocoris tenuis(+TX、)+TX、古铜黑蝇(Ophyra aenescens)+TX、狡小花蝽(Oriusinsidiosus)(Thripor-+TX、Oriline)+TX、无毛小花蝽(Orius laevigatus)(Thripor-+TX、Oriline)+TX、大臀小花蝽(Orius majusculus)(Oriline)+TX、小黑花椿象(Orius strigicollis)(Thripor-)+TX、Pauesia juniperorum+TX、瓢虫柄腹姬小蜂(Pediobius foveolatus)+TX、Phasmarhabditis hermaphrodita+TX、Phymastichus coffea+TX、粗毛小植绥螨(Phytoseiulusmacropilus)+TX、智利小植绥螨(Phytoseiulus persimilis)(+TX、Phytoline)+TX、斑腹刺益蝽(Podisus maculiventris)+TX、寄生性蚤蝇(Pseudacteon)curvatus+TX、寄生性蚤蝇(Pseudacteon)obtusus+TX、寄生性蚤蝇(Pseudacteon)tricuspis+TX、Pseudaphycus maculipennis+TX、Pseudleptomastixmexicana+TX、具毛嗜木虱跳小蜂(Psyllaephagus pilosus)+TX、同色短背茧蜂(Psyttaliaconcolor)(复合体)+TX、胯姬小蜂属物种(Quadrastichus spp.)+TX、Rhyzobiuslophanthae+TX、澳洲瓢虫(Rodolia cardinalis)+TX、Rumina decollate+TX、Semielacherpetiolatus+TX、麦长管蚜(Sitobion avenae)+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)(Nematac+TX、+TX、BioNem+TX、+TX、+TX、)+TX、夜蛾斯氏线虫(Steinernema feltiae)(+TX、Nemasys+TX、BioNem+TX、Steinernema-+TX、+TX、+TX、Exhibitline+TX、Scia-+TX、)+TX、锯蜂线虫(Steinernema kraussei)(Nemasys+TX、BioNem+TX、Exhibitline)+TX、锐比斯氏线虫(Steinernemariobrave)(+TX、)+TX、蝼蛄斯氏线虫(Steinernemascapterisci)(Nematac)+TX、斯氏线虫属物种(Steinernema spp.)+TX、斯氏科物种(Steinernematid spp.)(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)(Tricho-)+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、紫韧革菌(Chondrostereumpurpureum)(Chontrol)+TX、胶孢炭疽菌(Colletotrichum gloeosporioides)+TX、辛酸铜+TX、三角形捕捉物(Delta trap)(Trapline)+TX、梨火疫病菌(Erwinia amylovora)(Harpin)(+TX、Ni-HIBIT Gold)+TX、磷酸铁+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(MCPhail trap)(Trapline)+TX、象甲和寄生蜂(Microctonus hyperodae)+TX、大豆红褐坏死病菌(Mycoleptodiscus terrestris)(Des-)+TX、+TX、+TX、+TX、信息素捕捉物(Pheromone trap)(Thripline)+TX、碳酸氢钾+TX、脂肪酸钾盐+TX、硅酸钾溶液(Sil-)+TX、碘化钾+硫氰酸钾+TX、SuffOil-+TX、蜘蛛毒液+TX、蝗虫小孢子虫(Nosemalocustae)(Semaspore Organic Grasshopper)+TX、粘滞捕捉物(Stickytrap)(Trapline+TX、Rebell)+TX和捕捉物(Takitrapline y+)+TX。
在活性成分之后的括号中的参考号,例如[3878-19-1]是指化学文摘登记号。上文描述的混合配伍物是已知的。在活性成分包括在“The Pesticide Manual[杀有害生物剂手册]”[The Pesticide Manual-AWorld Compendium[杀有害生物剂手册-全球概览];第13版;编辑:C.D.S.TomLin;The British Crop Protection Coimcil[英国农作物保护委员会]]中的情况下,它们在其中以上文对于特定化合物的圆括号中所给出的条目编号来描述;例如化合物“阿维菌素”以条目编号(1)来描述。在“[CCN]”在上文添加到特定化合物的情况下,所讨论的化合物包括在“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 PesticideCommon 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。
上述活性成分中的大多数上文中通过所谓的“通用名”来提及,在个别的情形中使用相关的“ISO通用名”或另一“通用名”。若名称不是“通用名”,则所使用的名称种类以特定化合物的圆括号中所给出的名称来代替;在这种情况下,使用IUPAC名称、IUPAC/化学文摘名、“化学名称”、“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A-1至表A-120和表P中所定义的化合物的具有式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A-1至表A-120和表P中所定义的一种化合物的化合物和如上所述的活性成分,它们优选地处于从100:1至1:6000,特别是从50:1至1:50的混合比,更特别是处于从20:1至1:20的比率,甚至更特别是从10:1至1:10,非常特别是从5:1至1:5,特别优选的从2:1至1:2的比率,同样优选的是从4:1至2:1的比率,尤其是1:1、或5:1、或5:2、或5:3、或5:4、或4:1、或4:2、或4:3、或3:1、或3:2、或2:1、或1:5、或2:5、或3:5、或4:5、或1:4、或2:4、或3:4、或1:3、或2:3、或1:2、或1:600、或1:300、或1:150、或1:35、或2:35、或4:35、或1:75、或2:75、或4:75、或1:6000、或1:3000、或1:1500、或1:350、或2:350、或4:350、或1:750、或2:750、或4:750的比率。那些混合比率是按重量计的。
如以上所述的混合物可以被用于控制有害生物的方法中,该方法包括将包含如以上所述的混合物的组合物施用于有害生物或其环境中,通过手术或疗法用于处理人或动物体的方法以及在人或动物体上实施的诊断方法除外。
包含选自表A-1至A-120和表P中定义的化合物的具有式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(所述混合物由这些单一活性成分组分的单独配制品构成,例如“桶混剂”),以及当以顺序方式(即,一个在另一个适度短的时间段之后,如几小时或几天)施用时组合使用这些单一活性成分。具有式I的化合物与如以上描述的活性成分的施用的顺序对于实施本发明并不是关键的。
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、植物激活剂、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。
组合物的施用方法,即控制上述类型的有害生物的方法,如喷洒、雾化、撒粉、刷涂、拌种、撒播或浇灌(它们被选择以适于普遍情况的预期目的)以及组合物用于控制上述类型的有害生物的用途是本发明的其他主题。典型的浓度比率是在0.1与1000ppm之间,优选在0.1与500ppm之间的活性成分。每公顷的施用比率通常是每公顷1至2000g活性成分、特别是10至1000g/ha、优选地是10至600g/ha。
在作物保护领域中,优选的施用方法是施用至植物的叶(叶施用),可以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,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植物的场所浸透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,例如以颗粒剂的形式(土施))来实现的。在水稻作物的情况下,此类颗粒剂可以被计量加入淹水的稻田中。
本发明的具有式I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。可以用化合物在种植前对繁殖材料进行处理,例如可以在播种前对种子进行处理。可替代地,化合物可以施用至种子籽粒(包衣),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。还可以在繁殖材料被种植在施用场所时施用组合物,例如在条播期间将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该化合物的种子。尽管成分的较多或较少的部分可以渗透到种子材料中,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,活性成分在种子的表面上。当所述种子产品被(再)种植时,它可以吸收活性成分。在实施例中,本发明使得其上粘附有具有式I的化合物的植物繁殖材料可得。此外,由此可得包含用具有式I的化合物处理过的植物繁殖材料的组合物。
种子处理包括本领域中已知的所有适合的种子处理技术,如拌种、种子包衣、种子撒粉、浸种以及种子造粒。可以通过任何已知的方法进行具有式I的化合物的种子处理施用,如在种子播种之前或播种/种植过程中对种子喷雾或撒粉。
本发明中的披露内容使得可获得本文所披露的实施例的每一种组合。
应当指出的是,本文中关于具有式I的化合物的披露内容关于具有式I*、I’a中每一种以及表A-1至A-120的化合物同样适用。
本发明的化合物可以凭借在低施用率下的更大功效和/或不同有害生物控制而区别于其他类似化合物,这可以由本领域技术人员使用实验程序,使用较低的浓度(如果需要),例如10ppm、5ppm、2ppm、1ppm或0.2ppm;或较低施用比率,如300、200或100mg AI/m2来证实。通过增加的安全性(针对地上和地下的非靶标生物体(如鱼、鸟和蜂)、改进的物理-化学特性或增加的生物可降解性)可以观察到更大的效力。
生物学实例
以下实例用来说明本发明。本发明的某些化合物与已知化合物的区别可以在于在低施用率下更大的疗效,这可以由本领域的普通技术人员使用在实例中概述的实验程序来证实。
实例B1:烟粉虱(棉花粉虱):摄食/接触活性
将棉花叶圆片置于24孔微量滴定板中的琼脂上并且用由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。孵育之后6天,针对死亡率对这些样品进行检查。
实例B2:黄瓜条叶甲(玉米根虫)
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由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)。侵染之后4天,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施用比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%控制的效果:
P3、P4、P5、P6、P7、P8、P9、P11。
实例B3:英雄美洲蝽(新热带区褐蝽象)
将24孔微量滴定板中的琼脂上的大豆叶片用由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。侵染之后5天,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施用比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%控制的效果:
P3、P5、P6。
实例B4:西花蓟马(西方花蓟马):摄食/接触活性
将向日葵叶圆片置于24孔微量滴定板中的琼脂上并且用由10'000DMSO储备溶液制备的水性测试溶液进行喷洒。在干燥之后,将叶圆片用混合年龄的花蓟马种群进行侵染。侵染之后7天,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:
实例B5:小菜蛾(Plutella xylostella)(小菜蛾(Diamond back moth))
将具有人工饲料的24孔微量滴定板用由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。侵染之后8天,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施用比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%控制的效果:
P3、P4、P5、P6、P7、P8、P9、P10、P11、P12。
实例B6:桃蚜(绿色桃蚜虫):摄食/接触活性
将向日葵叶圆片置于24孔微量滴定板中的琼脂上并且用由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,将叶圆片用混合年龄的蚜虫种群进行侵染。侵染之后6天,针对死亡率对这些样品进行评估。
实例B7:桃蚜(绿桃蚜)。内吸活性
将被混合年龄的蚜虫种群侵染的豌豆幼苗的根部直接放在由10'000DMSO储备溶液制备的水性测试溶液中。将幼苗放在测试溶液中之后6天,针对死亡率对这些样品进行评估。
实例B8:桃蚜(绿桃蚜)。内在活性
将从10'000ppm DMSO储备溶液制备的测试化合物通过移液管施用到24孔微量滴定板中并与蔗糖溶液混合。用拉伸的石蜡膜(Parafilm)封闭板。将具有24个孔的塑料模板放置在板上,并将侵染的豌豆幼苗直接放置在石蜡膜上。用凝胶吸印纸和另一个塑料模板封闭侵染的板,然后倒置。侵染之后5天,针对死亡率对这些样品进行评估。
以下化合物在12ppm测试比率下产生至少80%的死亡率:
P3、P12。
实例B9:小菜蛾(Plutella xylostella)(小菜蛾(Diamond back moth))
将具有人工饲料的24孔微量滴定板用由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)。侵染之后5天,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。
实例B10:海灰翅夜蛾(Spodoptera littoralis)(埃及棉叶虫)
将棉花叶圆片置于24孔微量滴定板中的琼脂上并且用由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。侵染之后3天,相比于未处理样品,针对死亡率、拒食作用以及生长抑制对这些样品进行评估。当这些类别(死亡率、拒食作用和生长抑制)中的至少一个高于未处理样品时,实现测试样品对海灰翅夜蛾的控制。
以下化合物在200ppm的施用率下产生三个类别(死亡率、拒食或生长抑制)中至少一个的至少80%控制:
P3、P4、P5、P6、P7、P8、P9、P11、P12。
实例B11:二点叶螨(二斑叶螨):摄食/接触活性
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雾。在干燥之后,将叶圆片用混合年龄的螨种群进行侵染。侵染之后8天,针对混合种群(流动平台)的死亡率对这些样品进行评估。
以下化合物在200ppm施用比率下产生至少80%的死亡率:
P6。
实例B12:烟蓟马(Thrips tabaci)(洋葱蓟马)摄食/接触活性
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雾。在干燥之后,将叶圆片用混合年龄的蓟马种群进行侵染。侵染之后6天,针对死亡率对这些样品进行评估。
实例B13:小菜蛾(Plutella xylostella)(小菜蛾(Diamondback Moth)):
通过液体处理机器人用从10’000ppm DMSO储备溶液制备的水性测试溶液处理含有人工饲料的96孔微量滴定板。干燥后,卵(每孔约30个)被侵染到悬挂在饲料上方的网状盖子上。这些卵孵化并且L1幼虫向下移动到该饲料。侵染之后9天,针对死亡率对这些样品进行评估。
以下化合物在500ppm施用率下给出至少80%死亡率的效果:
P6、P10、P11。
实例14:二化螟(Chilo suppressalis)(水稻二化螟(Striped ricestemborer)):
将具有人工饲料的24孔微量滴定板用由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(6-8只/孔)。侵染之后6天,相比于未处理样品,针对死亡率、拒食作用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,实现测试样品对二化螟的控制。
以下化合物在200ppm的施用率下产生三个类别(死亡率、拒食或生长抑制)中至少一个的至少80%控制:
P3、P4、P5、P6、P8、P9、P10、P11、P12。
Claims (15)
1.一种具有式I的化合物
其中:
A1是N或CH;
R1是氢、C1-C6烷基、C1-C6氰基烷基、氨基羰基C1-C6烷基、羟基羰基C1-C6烷基、C1-C6硝基烷基、三甲基硅烷C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基;C3-C4环烷基C1-C2烷基-,其中所述C3-C4环烷基任选地被1或2个卤素原子取代;氧杂环丁烷-3-基-CH2-;或任选地被卤素或C1-C6卤代烷基取代的苄基;
R2是苯基、吡啶、嘧啶、吡嗪或哒嗪,其中所述苯基、吡啶、嘧啶、吡嗪或哒嗪任选地被一至三个取代基取代,其前提是所述一个或多个取代基不在与C=O附接的碳相邻的任一碳上,并且各取代基独立地选自:C1-C3烷基、C1-C3卤代烷基、C1-C3硫代卤代烷基、C1-C3烷氧基、C1-C3卤代烷氧基、卤素、NO2、SF5、CN、CONH2、COOH和C(S)NH2;
R3是C1-C3烷基或C1-C3卤代烷基;
R4是C2-C6卤代烯基、C2-C6卤代炔基、C3-C4卤代环烷基、或C3-C6环烷基C1-C4卤代烷基;
R5是H、C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基、C1-C3烷氧基、C1-C3烷氧基羰基、或二(C1-C3烷氧基)次甲基;或者所述具有式I的化合物的立体异构体、对映异构体、互变异构体和N-氧化物,或其农用化学上可接受的盐。
2.如权利要求1所述的具有式I的化合物,其中,A1是N或CH;R1是氢、C1-C6烷基、C1-C6氰基烷基、氨基羰基C1-C6烷基、羟基羰基C1-C6烷基、C1-C6硝基烷基、三甲基硅烷C1-C6烷基、C1-C6卤代烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基;C3-C4环烷基C1-C2烷基-,其中所述C3-C4环烷基任选地被1或2个卤素原子取代;氧杂环丁烷-3-基-CH2-;或任选地被卤素或C1-C6卤代烷基取代的苄基;R2是K1、K2、K4至K21;R3是C1-C3烷基或C1-C3卤代烷基;R4是C1-C6卤代烷基、C2-C6卤代烯基、C2-C6卤代炔基、C3-C4卤代环烷基、或C3-C6环烷基C1-C4卤代烷基;R5是H、C1-C3烷基、C1-C3卤代烷基、C3-C4环烷基、C1-C3烷氧基、C1-C3烷氧基羰基、或二(C1-C3烷氧基)次甲基;或者所述具有式I的化合物的立体异构体、对映异构体、互变异构体和N-氧化物,或其农用化学上可接受的盐;
3.根据权利要求1或权利要求2所述的化合物,其中,R1是氢、环丙基-CH2-、氢或CH3。
4.根据权利要求1至3中任一项所述的化合物,其中,R3是C1-C3烷基。
5.根据权利要求1至4中任一项所述的化合物,其中,R4选自C2-C4氟烯基、或C2-C4氟炔基。
6.根据权利要求1至5中任一项所述的化合物,其中,R4选自3,3,3-三氟丙-1-烯氧基。
7.根据权利要求2、3和4中任一项所述的化合物,其中,其中R4选择C1-C4氟烷基。
8.根据权利要求2、3、4和7中任一项所述的化合物,其中,其中R2是K1、K5、K6、K11、K12、K13、K15、K16、K18、K19、K20、或K21。
9.一种组合物,其包含如权利要求1至8中任一项所定义的化合物、一种或多种助剂和稀释剂、以及任选地一种或多种其他活性成分。
10.一种对抗并控制昆虫、螨、线虫或软体动物的方法,其包括将杀昆虫、杀螨、杀线虫或杀软体动物有效量的如权利要求1至8中任一项所定义的化合物或如权利要求9所定义的组合物施用到有害生物、有害生物的场所、或易受有害生物攻击的植物上。
11.一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,其包括用有效量的如权利要求1至8中任一项所定义的化合物或如权利要求9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地。
12.一种植物繁殖材料,如种子,其包含如权利要求1至8中任一项所定义的化合物或如权利要求9所定义的组合物,或将其用如权利要求1至8中任一项所定义的化合物或如权利要求9所定义的组合物进行处理,或将如权利要求1至8中任一项所定义的化合物或如权利要求9所定义的组合物粘附到其上。
13.一种控制有需要的动物体内或体表的寄生虫的方法,其包括给予有效量的如权利要求1至8中任一项所定义的化合物或如权利要求9所定义的组合物。
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EP3696175A1 (en) | 2020-08-19 |
US20220110325A1 (en) | 2022-04-14 |
WO2020169445A1 (en) | 2020-08-27 |
EP3927694A1 (en) | 2021-12-29 |
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