CN115210218A - 杀有害生物活性的环胺化合物 - Google Patents
杀有害生物活性的环胺化合物 Download PDFInfo
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- CN115210218A CN115210218A CN202180018936.5A CN202180018936A CN115210218A CN 115210218 A CN115210218 A CN 115210218A CN 202180018936 A CN202180018936 A CN 202180018936A CN 115210218 A CN115210218 A CN 115210218A
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Classifications
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- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/44—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom three- or four-membered rings
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- A—HUMAN NECESSITIES
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- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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- 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
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Abstract
具有式(I)的化合物,其中取代基是如权利要求1中所定义的,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、特别是杀昆虫或杀螨活性的环胺化合物(优选氮杂环丁烷基、哌啶基和哌嗪基芳基羰基化合物)(优选具有杀螨活性)、其制备方法、包含那些化合物的组合物、以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 2015032280、CN 106316931、WO 2017195703、WO 2019039429、WO 2019082808、JP 2019077618和JP 2019085371描述了某些哌啶基和哌嗪基吡啶基羰基化合物用于控制损害植物的有害生物的用途。
现在已经发现新颖的杀有害生物活性的氮杂环丁烷基、哌啶基和哌嗪基芳基羰基化合物。
因此,本发明在第一方面涉及具有式(I)的化合物
其中
R1是CN、C(=S)NH2或C1-C6-卤代烷基;
R2是H、OH、卤素、C1-C6-烷氧基或C1-C6-卤代烷氧基;
R3是H、卤素、氰基、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-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基、或C1-C6-卤代烷氧基;
R4是H、卤素、氰基、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-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基、或C1-C6-卤代烷氧基;
R5是苯基、被1至3个取代基R6取代的苯基、杂芳基(其是5或6元单环的或9或10元二环的)、被1至3个取代基R7取代的杂芳基(其是5或6元单环的或9或10元二环的);
Q是由式IIa表示的环胺或由式IIb表示的环胺,
其中箭头指示与羰基的连接;
p1是0、1或2并且指示亚甲基数;
p2是0、1或2并且指示亚甲基数;
q1是1或2并且指示亚甲基数;
q2是1或2并且指示亚甲基数;
X是氢、羟基、C1-C6-烷氧基、氰基或卤素;
Y是氰基、C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷基硫烷基-C1-C6-烷基、C1-C6-烷基亚磺酰基-C1-C6-烷基、C1-C6-烷基磺酰基-C1-C6-烷基、C3-C6-烯基硫烷基-C1-C6-烷基、C3-C6-烯基亚磺酰基-C1-C6-烷基、C3-C6-烯基磺酰基-C1-C6-烷基、C3-C6-炔基硫烷基-C1-C6-烷基、C3-C6-炔基亚磺酰基-C1-C6-烷基、C3-C6-炔基磺酰基-C1-C6-烷基、C1-C6-烷氧基羰基、C1-C6-烷氧基羰基氨基、RaRbNC(O)、RcC(O)NRd、ReSO2NRf、RgO-N=CRh、4至6元非芳香族杂环环体系——其中一个或两个碳独立地被氮、氧、硫或磺酰基替代、苯基、被1至3个取代基R8取代的苯基、5或6元单环杂芳基、或被1至3个取代基R9取代的5或6元单环杂芳基;或者
X和Y一起形成到氮的双键,其被基团RmO取代;
A是氰基、C1-C6-氰基烷基、C2-C6-氰基烯基、C3-C6-氰基环烷基、C1-C6-卤代烷基、C2-C6-卤代烯基、C3-C6-卤代环烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷氧基羰基、C2-C6-烯氧基羰基、C2-C6-炔氧基羰基、C1-C6-烷基硫烷基-C1-C6-烷基、C1-C6-烷基亚磺酰基-C1-C6-烷基、C1-C6-烷基磺酰基-C1-C6-烷基、RiSO2、RjRkNSO2、苯基、被1至3个取代基R10取代的苯基、杂芳基(其是5或6元单环的或9或10元二环的)、或被1至3个取代基R11取代的杂芳基(其是5或6元单环的或9或10元二环的);
Ra和Rb独立地选自氢、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-C6-环烷基和C3-C6-卤代环烷基以及C1-C6-烷基磺酰基;
Rc和Rd独立地选自氢、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-C6-环烷基和C3-C6-卤代环烷基;
Rf是氢、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-C6-环烷基或C3-C6-卤代环烷基;
Re和Ri独立地选自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-C6-环烷基和C3-C6-卤代环烷基;
Rg和Rh独立地选自氢、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-C6-环烷基和C3-C6-卤代环烷基;
Rj和Rk独立地选自氢、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-C6-环烷基和C3-C6-卤代环烷基;
Rm是氢、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-C6-环烷基或C3-C6-卤代环烷基;并且
R6、R7、R8、R9、R10、R11独立地选自卤素、氰基、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-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷基磺酰基和C1-C6-卤代烷基硫烷基;
或该具有式I的化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N-氧化物。
具有至少一个碱性中心的具有式(I)的化合物可以例如与以下形成例如酸加成盐: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、三乙胺或二甲基丙基胺,或单、二或三羟基低级烷基胺,例如单乙醇胺、二乙醇胺或三乙醇胺)形成盐。
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、处于氧化形式(如N-氧化物)或处于盐的形式(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。
如本文所用,术语“C1-Cn-烷基”是指具有1至n个碳原子、经由任一碳原子附接的饱和直链或支链烃基,例如以下基团中的任一种:甲基、乙基、正丙基、正丁基、正戊基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、正己基、正戊基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、或1-乙基-2-甲基丙基。
如本文所用,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。
如本文所用,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,
如本文所用,术语“C3-Cn-环烷基”是指3元-n元环烷基,如环丙烷、环丁烷、环戊烷和环己烷。
如本文所用,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(如上提及的),该饱和烷基经由氧原子附接,即,例如以下基团中的任一种: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。如本文所用,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一个或多个相同或不同的卤代原子替代-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。
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。
如本文所用,术语“C1-Cn-卤代烷基”是指具有1至n个碳原子、经由任一碳原子附接的直链或支链饱和烷基(如上提及的),其中这些基团中的一些或全部氢原子可以被氟、氯、溴和/或碘替代,即,例如以下中的任一种:氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟甲基、氯二氟甲基、2-氟乙基、2-氯乙基、2-溴乙基、2-碘乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基、2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、2,2,3,3,3-五氟丙基、七氟丙基、1-(氟甲基)-2-氟乙基、1-(氯甲基)-2-氯乙基、1-(溴甲基)-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基或九氟丁基。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。类似地,如本文所用,术语“C2-Cn-卤代烯基”或“C2-Cn-卤代炔基”分别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-烯基或C2-Cn-炔基部分。类似地,如本文所用,术语“C3-Cn-卤代环烷基”是指被一个或多个可以相同或不同的卤素原子取代的C3-Cn-环烷基。
如本文所用,术语“C1-Cn-氰基烷基”是指具有1至n个碳原子的C1-Cn-烷基(如上提及的),其中该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。类似地,术语“C1-Cn-氰基烯基”或“C1-Cn-氰基炔基”分别是指取代的C2-Cn-烯基或C1-Cn-炔基部分,其中相应部分中的氢原子之一被氰基替代。
如本文所用,术语“C1-Cn-烷基硫烷基-C1-Cn-烷基”是指烷基,其中碳原子之一被硫原子替代。
如本文所用,术语“C1-Cn-烷基亚磺酰基-C1-Cn-烷基”是指烷基,其中碳原子之一被S(=O)基团替代。
如本文所用,术语“C1-Cn-烷基磺酰基-C1-Cn-烷基”是指烷基,其中碳原子之一被S(=O)2基团替代。
如本文所用,术语“4至6元非芳香族杂环环体系——其中一个或两个碳被氮、氧、硫或磺酰基替代”是指环状基团,其中环中的一个或两个碳原子独立地被氮、氧、硫或磺酰基替代,并且环经由碳或氮原子附接至化合物的剩余部分。实例是氮杂环丁烷基、氧杂环丁烷基、硫杂环丁烷基、吡咯烷基、四氢呋喃基、2-氧代吡咯烷基、2-氧代四氢呋喃基、1,1-二氧代-1,2-噻唑烷基、1,3-二氧戊环基、1,3-二硫戊环基、2-氧代噁唑烷基、哌啶基、四氢吡喃基、2-氧代哌啶基、1,1-二氧代噻嗪基、2-氧代四氢吡喃基、1,3-二氧戊环基、1,3-二噻烷基、2-氧代-1,3-噁嗪烷基。
如本文所用,术语“苯基-C1-Cn-烷基”是指被苯基环取代的烷基。如果苯基-C1-Cn-烷基上有取代,则取代在苯基环上。
如本文所用,术语“C1-Cn-烷氧基-C1-Cn-烷基”是指被C1-Cn-烷氧基取代的烷基。实例是甲氧基甲基、甲氧基乙基、乙氧基甲基和丙氧基甲基。
如本文所用,术语“C1-Cn-烷氧基羰基”是指连接至羰基(C=O)基团的C1-Cn-烷氧基,通过该羰基,C1-Cn-烷氧基羰基附接至化合物的剩余部分。实例是甲氧基羰基、乙氧基羰基、异丙氧基羰基和叔丁氧基羰基。
如本文所用,术语“C1-C6-烷氧基羰基氨基”是指连接至氨基(NH)基团的C1-Cn-烷氧基羰基,通过该氨基,C1-Cn-烷氧基羰基氨基附接至化合物的剩余部分。实例为
如本文所用,术语“C2-Cn-烯氧基羰基”是指用氧原子连接至羰基(C=O)基团的C2-Cn-烯基,并且其中与化合物的剩余部分的附接是通过羰基的碳原子。实例是乙烯基氧基羰基和烯丙基氧基羰基。
如本文所用,术语“C2-Cn-炔氧基羰基”是指用氧原子连接至羰基(C=O)基团的C2-Cn-炔基,并且其中与化合物的剩余部分的附接是通过羰基的碳原子。实例是炔丙基氧基羰基(2-丙-2-炔氧基羰基)和2-戊-3-炔氧基羰基,
取代基RgO-N=CRh具有下面的通式
如本文所用,术语“5或6元单环杂芳基”是指5或6元芳香族环,使1至3个碳原子独立地被氮、硫、或氧替代。实例是吡啶基、哒嗪基、嘧啶基、吡嗪基、吡咯基、吡唑基、咪唑基、三唑基(例如,1,2,4-三唑基)、呋喃基、噻吩基、噁唑基、异噁唑基、噁二唑基、噻唑基、异噻唑基以及噻二唑基。实例是下面的方案A中所示的杂芳基J-1至J-35。优选的杂芳基是J-1、J-16、J-18或J-20。
如本文所用,术语“9或10元二环杂芳基”是指9或10元芳香族环,其由两个环构成、使1至3个碳原子独立地被氮、硫、或氧(这些杂原子可以在一个环中或分布在两个环中)替代。实例是嘌呤基、喹啉基、噌啉基、喹喔啉基、吲哚基、吲唑基、苯并咪唑基、苯并噻吩基以及苯并噻唑基。
方案A:杂芳基J-1至J-35
如本文所用,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,使得减少对植物或对植物衍生产品的损害。
如本文所用,术语“有害生物”是指在农业、园艺、林业、植物来源的产品(如果实、谷物和木材)的储存中存在的昆虫和软体动物;以及那些与人造结构的损坏相关的有害生物。术语有害生物涵盖有害生物生命周期的所有阶段。
如本文所用,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希望的效果。
如本文例如在式IV-aa和IV-ba中使用的交错线表示与化合物的剩余部分的连接/附接点。
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品的类型;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;以及其他相关情况。
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,R1是
A.CN、C(=S)NH2或C1-C3-卤代烷基;或者
B.CN、C(=S)NH2、二氟甲基或三氟甲基;或者
C.CN。
在本发明的每个方面的实施例中,R2是
A.氢、卤素、C1-C6-烷氧基或C1-C6-卤代烷氧基;或者
B.氢、卤素、C1-C3-烷氧基或C1-C3-卤代烷氧基;或者
C.氢、氟、氯、甲氧基、二氟甲氧基、或三氟甲氧基;或者
D.氢。
在本发明的每个方面的实施例中,R3是
A.氢、OH、卤素、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基或C1-C6-卤代烷氧基;或者
B.氢、卤素、C1-C6-烷基、或C1-C6-卤代烷基、C1-C6-烷氧基或C1-C6-卤代烷氧基;或者
C.氢、卤素、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基或C1-C3-卤代烷氧基;或者
D.氢、氯、氟、甲基、乙基、甲氧基、乙氧基、二氟甲基、三氟甲基、或五氟乙基;或者
E.氢、甲基、乙基、甲氧基、乙氧基、二氟甲基、三氟甲基、或五氟乙基;或者
F.甲基、甲氧基、乙氧基、二氟甲基或三氟甲基。
在本发明的每个方面的实施例中,R4是
A.氢、氰基、卤素、C1-C3-烷基、C1-C3-卤代烷基、C3-C3-环烷基、C3-C3-卤代环烷基、C1-C3-烷氧基或C1-C3-卤代烷氧基;或者
B.氢、氰基、或卤素;或者
C.氢、氰基、氟或氯;或者
D.氢或氰基。
在本发明的每个方面的实施例中,R5是
A.苯基、被1至3个取代基R6取代的苯基、5或6元单环杂芳基或被1至3个取代基R7取代的5或6元单环杂芳基;或者
B.苯基或被1至3个取代基R6取代的苯基;或者
C.被1至3个取代基R6取代的苯基。
在本发明的每个方面的实施例中,Q是
A.由式IIa表示的环胺,其中p1和p2二者都是0或1;X是氢、羟基、C1-C3-烷氧基、氰基、或卤素;并且Y是氰基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷基硫烷基-C1-C6-烷基、C1-C6-烷基亚磺酰基-C1-C6-烷基、C1-C6-烷基磺酰基-C1-C6-烷基、C3-C6-烯基硫烷基-C1-C6-烷基、C3-C6-烯基亚磺酰基-C1-C6-烷基、C3-C6-烯基磺酰基-C1-C6-烷基、C3-C6-炔基硫烷基-C1-C6-烷基、C3-C6-炔基亚磺酰基-C1-C6-烷基、C3-C6-炔基磺酰基-C1-C6-烷基、C1-C6-烷氧基羰基、C1-C6-烷氧基羰基氨基、RaRbNC(O)、ReSO2NRf、RgO-N=CRh、4至6元非芳香族杂环环体系——其中一个或两个碳独立地被氮或磺酰基替代、苯基、被1至3个取代基R8取代的苯基、5或6元单环杂芳基、或被1至3个取代基R9取代的5或6元单环杂芳基;或X和Y一起形成到氮的双键,其被基团RmO取代;或者
B.由式IIa表示的环胺,其中p1和p2二者都是0或1;X是氢或羟基;Y是C1-C3-烷基硫烷基-C1-C3-烷基、C1-C3-烷基亚磺酰基-C1-C3-烷基、C1-C3-烷基磺酰基-C1-C3-烷基、C3-C4-烯基硫烷基-C1-C3-烷基、C3-C4-烯基亚磺酰基-C1-C3-烷基、C3-C4-烯基磺酰基-C1-C3-烷基、C3-C4-炔基硫烷基-C1-C3-烷基、C3-C4-炔基亚磺酰基-C1-C3-烷基、C3-C4-炔基磺酰基-C1-C3-烷基、RaRbNC(O)、ReSO2NRf、RgO-N=CRh、4至6元非芳香族杂环环体系——其中一个或两个碳独立地被氮或磺酰基替代、5或6元单环杂芳基、或被1至3个取代基R9取代的5或6元单环杂芳基;或X和Y一起形成到氮的双键,其被基团RmO取代;或者
C.由式IIa表示的环胺,其中p1和p2二者都是0或1;X是氢或羟基;Y是C1-C3-烷基硫烷基-C1-C3-烷基、C1-C3-烷基亚磺酰基-C1-C3-烷基、C1-C3-烷基磺酰基-C1-C3-烷基、C3-C4-烯基硫烷基-C1-C3-烷基、C3-C4-烯基亚磺酰基-C1-C3-烷基、C3-C4-烯基磺酰基-C1-C3-烷基、C3-C4-炔基硫烷基-C1-C3-烷基、C3-C4-炔基亚磺酰基-C1-C3-烷基、C3-C4-炔基磺酰基-C1-C3-烷基、RaRbNC(O)、ReSO2NRf、RgO-N=CRh、4至6元非芳香族杂环环体系——其中一个或两个碳独立地被氮或磺酰基替代、5或6元单环杂芳基、或被1至3个取代基R9取代的选自J-1至J-35的5或6元单环杂芳基;或X和Y一起形成到氮的双键,其被基团RmO取代;或者
D.由式IIa表示的环胺,其中p1和p2二者都是0或1;X是氢或羟基;Y是C1-C3-烷基硫烷基-甲基、C1-C3-烷基亚磺酰基-甲基、C1-C3-烷基磺酰基-甲基、C3-C4-烯基硫烷基-甲基、C3-C4-烯基亚磺酰基-甲基、C3-C4-烯基磺酰基-甲基、C3-C4-炔基硫烷基-甲基、C3-C4-炔基亚磺酰基-甲基、C3-C4-炔基磺酰基-甲基、甲磺酰胺基、乙磺酰胺基、1,1-二氧代-1,2-噻唑烷-2-基、1,2,4-噁二唑-3-基、2-吡啶基、取代的2-吡啶基或取代的1,2,4-噁二唑-3-基,其中每一个的取代基是1至3个独立地选自氯和甲基的取代基;或X和Y一起形成到氮的双键,其被甲氧基或乙氧基取代;或者
E.由式IIa表示的环胺,其中p1和p2二者各自是1;X是氢;Y是C1-C3-烷基硫烷基-甲基、C1-C3-烷基亚磺酰基-甲基、C1-C3-烷基磺酰基-甲基、C3-C4-烯基硫烷基-甲基、C3-C4-烯基亚磺酰基-甲基、C3-C4-烯基磺酰基-甲基、C3-C4-炔基硫烷基-甲基、C3-C4-炔基亚磺酰基-甲基、C3-C4-炔基磺酰基-甲基、甲磺酰胺基、乙磺酰胺基、1,1-二氧代-1,2-噻唑烷-2-基、1,2,4-噁二唑-3-基、2-吡啶基、取代的2-吡啶基或取代的1,2,4-噁二唑-3-基,其中每一个的取代基是1至3个独立地选自氯和甲基的取代基;或X和Y一起形成到氮的双键,其被甲氧基或乙氧基取代;或者
F.由式IIb表示的环胺;其中q1和q2都是1;并且A是氰基、C1-C6-氰基烷基、C2-C6-氰基烯基、C3-C6-氰基环烷基、C1-C6-卤代烷基、C2-C6-卤代烯基、C3-C6-卤代环烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷氧基羰基、C2-C6-烯氧基羰基、C2-C6-炔氧基羰基、C1-C6-烷基硫烷基-C1-C6-烷基、C1-C6-烷基亚磺酰基-C1-C6-烷基、RiSO2、RjRkNSO2、苯基、被1至3个取代基R10取代的苯基、杂芳基(其是5或6元单环的或9或10元二环的)、或被1至3个取代基R11取代的杂芳基(其是5或6元单环的或9或10元二环的);
G.由式IIb表示的环胺;其中q1和q2都是1;并且A是氰基、C1-C3-氰基烷基、C2-C4-氰基烯基、C3-C4-氰基环烷基、C1-C3-卤代烷基、C2-C3-卤代烯基、C3-C4-卤代环烷基、C1-C3-烷氧基-C1-C3-烷基、C1-C3-烷氧基羰基、C2-C4-烯氧基羰基、C2-C4-炔氧基羰基、C1-C3-烷基硫烷基-C1-C3-烷基、C1-C3-烷基亚磺酰基-C1-C3-烷基、RiSO2、RjRkNSO2、苯基、被1至3个取代基R10取代的苯基、杂芳基(其是5或6元单环的或9或10元二环的)、或被1至3个取代基R11取代的杂芳基(其是5或6元单环的或9或10元二环的);
H.由式IIb表示的环胺;其中q1和q2都是1;并且A是氰基、C1-C3-氰基烷基、C1-C3-卤代烷基、C2-C3-卤代烯基、C1-C3-烷氧基-C1-C3-烷基、C1-C3-烷氧基羰基、C1-C3-烷基硫烷基-C1-C3-烷基、C1-C3-烷基亚磺酰基-C1-C3-烷基、RiSO2、或被1至3个取代基R11取代的5或6元单环杂芳基;
I.由式IIb表示的环胺;其中q1和q2都是1;并且A是氰基、C1-C3-氰基烷基、C1-C3-卤代烷基、C2-C3-卤代烯基、C1-C3-烷氧基-C1-C3-烷基、C1-C3-烷氧基羰基、C1-C3-烷基硫烷基-C1-C3-烷基、C1-C3-烷基亚磺酰基-C1-C3-烷基、RiSO2、或被1至3个独立地选自氟和氯的取代基取代的6元单环杂芳基,或
J.由式IIb表示的环胺;其中q1和q2都是1;并且A是氰基、氰基甲基、氰基乙基、2,2,2-三氟乙基、乙烯氧基羰基、丁氧基羰基、甲基硫烷基甲基、乙基硫烷基乙基、甲基硫烷基乙基(即CH3SCH2CH2)、乙基亚磺酰基乙基、乙基亚磺酰基甲基、乙基磺酰基乙基、乙基磺酰基甲基、甲基磺酰基甲基、4-氯-苯基、或被1至3个独立地选自氟、氯、三氟甲基和二氟甲基的取代基取代的吡啶基;或者
K.由式IIb表示的环胺;其中q1和q2都是1;并且A是氰基、氰基甲基、氰基乙基、CH3SCH2CH2、或被1至3个独立地选自氟、氯、三氟甲基和二氟甲基的取代基取代的吡啶基。
在本发明的每个方面的实施例中,X是
A.氢、羟基、C1-C3-烷氧基、氰基或卤素;或者
B.氢、羟基、或C1-C3-烷氧基;或者
C.氢、或羟基;或者
D.氢。
在本发明的每个方面的实施例中,Ra和Rb独立地选自
A.氢、C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基和C3-C4-卤代环烷基以及C1-C3-烷基磺酰基;或者
B.氢、C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基和C3-C4-卤代环烷基以及C1-C3-烷基磺酰基;或者
C.氢、C1-C3-烷基、C1-C3-卤代烷基、或C1-C3-烷基磺酰基;或者
D.氢、C1-C3-烷基、或C1-C3-烷基磺酰基;或者
E.氢、甲基、乙基、甲基磺酰基、或乙基磺酰基。
在本发明的每个方面的实施例中,Rc和Rd独立地选自
A.C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基和C3-C4-卤代环烷基;或者
B.C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基和C3-C4-卤代环烷基;或者
C.C1-C3-烷基、C1-C3-卤代烷基和C3-C4-卤代环烷基;或者
D.C1-C3-烷基和C1-C3-卤代烷基;或者
E.甲基、乙基、二氟甲基和三氟甲基。
在本发明的每个方面的实施例中,Rf是
A.氢、C1-C3-烷基、或C3-C4-环烷基;或者
B.氢或C1-C3-烷基;或者
C.氢、甲基和乙基。
在本发明的每个方面的实施例中,Re是
A.C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基或C3-C4-卤代环烷基;或者
B.C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基或C3-C4-卤代环烷基;或者
C.C1-C3-烷基或C1-C3-卤代烷基;或者
D.甲基、乙基、二氟甲基或三氟甲基。
在本发明的每个方面的实施例中,Ri是
A.C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基或C3-C4-卤代环烷基;或者
B.C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基或C3-C4-卤代环烷基;或者
C.C1-C3-烷基或C1-C3-卤代烷基;或者
D.甲基、乙基、二氟甲基或三氟甲基。
在本发明的每个方面的实施例中,Rg和Rh独立地选自
A.C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基和C3-C4-卤代环烷基;或者
B.C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基和C3-C4-卤代环烷基;或者
C.C1-C3-烷基、C1-C3-卤代烷基和C3-C4-卤代环烷基;或者
D.C1-C3-烷基和C1-C3-卤代烷基;或者
E.甲基、乙基、二氟甲基和三氟甲基;或者
F.甲基和乙基。
在本发明的每个方面的实施例中,Rj和Rk独立地选自
A.C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基和C3-C4-卤代环烷基;或者
B.C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基和C3-C4-卤代环烷基;或者
C.C1-C3-烷基、C1-C3-卤代烷基和C3-C4-卤代环烷基;或者
D.C1-C3-烷基和C1-C3-卤代烷基;或者
E.甲基、乙基、二氟甲基和三氟甲基;或者
F.甲基和乙基。
在本发明的每个方面的实施例中,Rm是
A.C1-C4-烷基;或者
B.甲基、乙基、或丙基;或者
C.甲基或乙基;
在本发明的每个方面的实施例中,R6选自
A.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
B.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
C.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
D.氟、氯、甲基、乙基、异丙基、三氟甲基、二氟甲基、三氟甲氧基、二氟甲氧基、三氟甲基硫烷基和甲基磺酰基。
在本发明的每个方面的实施例中,R7选自
A.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
B.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
C.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
D.卤素、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
E.卤素、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
F.卤素、C1-C3-烷基和C1-C3-卤代烷基以及C1-C3-卤代烷氧基;或者
G.氟、氯、甲基、乙基、异丙基、三氟甲基、二氟甲基、三氟甲氧基和二氟甲氧基。
在本发明的每个方面的实施例中,R8选自
A.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
B.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
C.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
D.卤素、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
E.卤素、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
F.卤素、C1-C3-烷基、C1-C3-卤代烷基和C1-C3-卤代烷氧基;或者
G.氟、氯、甲基、乙基、异丙基、三氟甲基、二氟甲基、三氟甲氧基和二氟甲氧基。
在本发明的每个方面的实施例中,R9选自
A.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
B.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
C.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
D.卤素、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
E.卤素、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
F.卤素、C1-C3-烷基、C1-C3-卤代烷基和C1-C3-卤代烷氧基;或者
G.氟、氯、甲基、乙基、异丙基、三氟甲基、二氟甲基、三氟甲氧基和二氟甲氧基;或者
H.氟、氯、甲基和乙基
在本发明的每个方面的实施例中,R10选自
A.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
B.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
C.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
D.卤素、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
E.卤素、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
F.卤素、C1-C3-烷基、C1-C3-卤代烷基和C1-C3-卤代烷氧基;或者
G.氟、氯、甲基、乙基、异丙基、三氟甲基、二氟甲基、三氟甲氧基和二氟甲氧基
在本发明的每个方面的实施例中,R11选自
A.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C2-C4-烯基、C2-C4-卤代烯基、C2-C4-炔基、C2-C4-卤代炔基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
B.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基;或者
C.卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C3-C4-环烷基、C3-C4-卤代环烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
D.卤素、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
E.卤素、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基和C1-C3-卤代烷氧基;或者
F.卤素、C1-C3-烷基、C1-C3-卤代烷基和C1-C3-卤代烷氧基;或者
G.氟、氯、甲基、乙基、异丙基、三氟甲基、二氟甲基、三氟甲氧基和二氟甲氧基;或者
H.氟、氯、甲基、乙基。
因此,本发明使得可获得具有式(I)的化合物,该化合物具有如上定义的取代基Q、R1、R2、R3、R4和R5(呈所有组合/每种排列)。因此,使得可获得例如具有式(I)的化合物,其中Q是实施例K(即Q是由式IIb表示的环胺;其中q1和q2都是1;并且A是氰基、氰基甲基、氰基乙基、CH3SCH2CH2、或被1至3个独立地选自氟、氯、三氟甲基和二氟甲基的取代基取代的吡啶基);R1是第一方面(即R1是CN、C(=S)NH2或C1-C6-卤代烷基);R2是实施例D(即R2是氢);R3是实施例A(即R3是氢、OH、卤素、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基、或C1-C6-卤代烷氧基);R4是实施例B(即R4是氢、氰基、或卤素);并且R5是实施例B(即R5是苯基、或被1至3个取代基R6取代的苯基;其中R6是实施例C(即R6是卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基、或C1-C3-卤代烷基硫烷基))。
具有式I的化合物可以由式Ia和Ib表示
其中式Ia中的取代基X、Y、R1、R2、R3、R4和R5是如对于式I所定义的;并且式Ib中的取代基A、R1、R2、R3、R4和R5是如对于式I所定义的。
在本发明的每个方面的实施例中,具有式(Ia)的化合物具有氢、羟基、C1-C6-烷氧基、氰基或卤素作为X;以下作为Y:氰基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷基硫烷基-C1-C6-烷基、C1-C6-烷基亚磺酰基-C1-C6-烷基、C1-C6-烷基磺酰基-C1-C6-烷基、C3-C6-烯基硫烷基-C1-C6-烷基、C3-C6-烯基亚磺酰基-C1-C6-烷基、C3-C6-烯基磺酰基-C1-C6-烷基、C3-C6-炔基硫烷基-C1-C6-烷基、C3-C6-炔基亚磺酰基-C1-C6-烷基、C3-C6-炔基磺酰基-C1-C6-烷基、C1-C6-烷氧基羰基、C1-C6-烷氧基羰基氨基、RaRbNC(O)、ReSO2NRf、RgO-N=CRh、4至6元非芳香族杂环环体系——其中一个或两个碳独立地被氮或磺酰基替代、苯基、被1至3个取代基R8取代的苯基、5或6元单环杂芳基、或被1至3个取代基R9取代的5或6元单环杂芳基;或X和Y一起形成到氮的双键,其被基团RmO取代;CN、C(=S)NH2或C1-C3-卤代烷基作为R1;氢、卤素、C1-C6-烷氧基、或C1-C6-卤代烷氧基作为R2;氢、OH、卤素、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基、或C1-C6-卤代烷氧基作为R3;氢、氰基、卤素、C1-C3-烷基、C1-C3-卤代烷基、C3-C3-环烷基、C3-C3-卤代环烷基、C1-C3-烷氧基、或C1-C3-卤代烷氧基作为R4;以及苯基、被1至3个取代基R6取代的苯基、5或6元单环杂芳基、或被1至3个取代基R7取代的5或6元单环杂芳基作为R5;其中Ra、Rb、Re、Rf、Rg、Rh、Rm、R6、R7、R8、R9是如第一方面中所定义的。
在本发明的每个方面的实施例中,具有式(Ib)的化合物具有以下作为A:氰基、C1-C3-氰基烷基、C2-C4-氰基烯基、C3-C4-氰基环烷基、C1-C3-卤代烷基、C2-C3-卤代烯基、C3-C4-卤代环烷基、C1-C3-烷氧基-C1-C3-烷基、C1-C3-烷氧基羰基、C2-C4-烯氧基羰基、C2-C4-炔氧基羰基、C1-C3-烷基硫烷基-C1-C3-烷基、C1-C3-烷基亚磺酰基-C1-C3-烷基、RiSO2、RjRkNSO2、苯基、被1至3个取代基R10取代的苯基、杂芳基(其是5或6元单环的或9或10元二环的)、或被1至3个取代基R11取代的杂芳基(其是5或6元单环的或9或10元二环的);CN、C(=S)NH2或C1-C3-卤代烷基作为R1;氢、卤素、C1-C6-烷氧基或C1-C6-卤代烷氧基作为R2;氢、OH、卤素、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基或C1-C6-卤代烷氧基作为R3;氢、氰基、卤素、C1-C3-烷基、C1-C3-卤代烷基、C3-C3-环烷基、C3-C3-卤代环烷基、C1-C3-烷氧基、或C1-C3-卤代烷氧基作为R4;以及苯基、被1至3个取代基R6取代的苯基、5或6元单环杂芳基、或被1至3个取代基R7取代的5或6元单环杂芳基作为R5;其中Ri、Rj、Rk、R6、R7、R10、R11是如第一方面中所定义的。
在本发明的每个方面的实施例中,具有式(Ia)的化合物具有氢作为X;以下作为Y:C1-C3-烷基硫烷基-甲基、C1-C3-烷基亚磺酰基-甲基、C1-C3-烷基磺酰基-甲基、C3-C4-烯基硫烷基-甲基、C3-C4-烯基亚磺酰基-甲基、C3-C4-烯基磺酰基-甲基、C3-C4-炔基硫烷基-甲基、C3-C4-炔基亚磺酰基-甲基、C3-C4-炔基磺酰基-甲基、甲磺酰胺基、乙磺酰胺基、1,1-二氧代-1,2-噻唑烷-2-基、1,2,4-噁二唑-3-基、2-吡啶基、取代的2-吡啶基或取代的1,2,4-噁二唑-3-基,其中每一个的取代基是1至3个独立地选自氯和甲基的取代基;或X和Y一起形成到氮的双键,其被甲氧基或乙氧基取代;CN作为R1;氢作为R2;甲基、甲氧基、乙氧基、二氟甲基、或三氟甲基作为R3;氢或氰基作为R4;被1至3个取代基R6取代的苯基作为R5;其中R6是氟、氯、甲基、乙基、异丙基、三氟甲基、二氟甲基、三氟甲氧基、二氟甲氧基、三氟甲基硫烷基、或甲基磺酰基。
在本发明的每个方面的实施例中,具有式(Ib)的化合物具有以下作为A:氰基、氰基甲基、氰基乙基、CH3SCH2CH2、或被1至3个独立地选自氟、氯、三氟甲基和二氟甲基的取代基取代的吡啶基;CN作为R1;氢作为R2;甲基、甲氧基、乙氧基、二氟甲基或三氟甲基作为R3;氢或氰基作为R4;被1至3个取代基R6取代的苯基作为R5;其中R6是氟、氯、甲基、乙基、异丙基、三氟甲基、二氟甲基、三氟甲氧基、二氟甲氧基、三氟甲基硫烷基、或甲基磺酰基。
在第二方面,本发明使得可获得一种组合物,该组合物包含如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。
在第三方面,本发明使得可获得一种对抗和控制昆虫、螨、线虫或软体动物的方法,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第一方面中所定义的化合物或如第二方面中所定义的组合物。
在第四方面,本发明使得可获得一种用于保护植物繁殖材料免受昆虫、螨、线虫或软体动物的攻击的方法,该方法包括用有效量的如第一方面中所定义的具有式(I)的化合物或如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,本发明使得可获得一种植物繁殖材料,如种子,该植物繁殖材料包含如第一方面中所定义的具有式(I)的化合物或如第二方面中所定义的组合物,或用该化合物或该组合物处理,或其上附着有该化合物或该组合物。
在另一方面,本发明提供了一种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一种控制有需要的动物的体表寄生虫的方法,该方法包括给予有效量的如第一方面中所定义的具有式(I)的化合物。本发明进一步提供了一种用于预防和/或治疗由体表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第一方面中所定义的具有式(I)的化合物。
具有式(I)的化合物可以由本领域技术人员按照已知的方法来制备。更具体地,具有式I的化合物和中间体因此可以如下面在方案和实例中所述制备。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技术人员已知的方法进行。
具有式(I)的化合物是新的并且可以通过以下方式制备:根据方案1,使用已知的酰胺偶联试剂如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)和碱例如胡宁氏碱(Hünig’s base)在合适的溶剂例如二甲基甲酰胺(DMF)或二甲基乙酰胺(DMA)中使酸III(其中R1、R2、R3、R4和R5是如先前定义的)与胺IV-a或IV-b(其中X、Y、A、p1、p2、q1和q2是如先前定义的)进行反应。哌啶IV-a或哌嗪IV-b是可商购的、从文献中已知或可以由本领域技术人员制备。
方案1:
可替代地,具有式(I)的化合物可以通过以下方式制备:根据方案2,在碱(例如三乙胺或吡啶)和合适的溶剂(例如二氯甲烷(DCM)、四氢呋喃(THF)或甲苯)的存在下使酰氯V(其中R1、R2、R3、R4和R5是如先前定义的)与胺IV-a或IV-b(其中X、Y、A、p1、p2、q1和q2是如先前定义的)进行反应。
方案2:
酰氯V(其中R1、R2、R3、R4和R5是如先前定义的)可以根据方案3通过在催化量的DMF存在下在惰性溶剂如DCM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由相应的酸III(其中R1、R2、R3、R4和R5是如先前定义的)制备。
方案3:
酸III(其中R1、R2、R3、R4和R5是如先前定义的)可以根据方案4通过以下方式制备:在碱性条件下例如使用无机碱如氢氧化锂、氢氧化钠、氢氧化钾或碳酸钾在水、甲醇、乙醇或THF中水解相应的酯VI(其中R1、R2、R3、R4和R5是如先前定义的并且R12=C1-C6-烷基)。
方案4:
酯VI(其中R1、R2、R3、R4和R5是如先前定义的)可以通过化合物VII(其中R1、R2、R3、R4是如先前定义的并且LG1是离去基团,例如碘、溴、氯或磺酸酯如三氟甲磺酸酯)与硼酸VIII或锡烷试剂IX的钯催化的交叉偶联反应制备。钯催化的交叉偶联反应是本领域技术人员已知的。这些反应可以在与这些条件相容的各种有机或水性溶剂中,以从低于0℃至溶剂体系的沸点的温度和各种钯催化剂例如四(三苯基膦)钯(0)或乙酸钯(II)和三苯基膦进行。
方案5:
根据下表1至20的具有式(I)的化合物可以根据以上所述的方法制备。随后的实例旨在说明本发明并且示出优选的具有式(I)的化合物(以具有式(I-a)的化合物的形式)。
下面的表M之后的表1至20中的每一个包括864种具有式(I-a)的化合物,其中R1、R3和R6具有在表M的每一行中给出的值,并且Y和X具有相关表1至20中给出的值。
因此,化合物1.1对应于具有式(I-a)的化合物,其中R1、R3和R6是如表M的第1行中所定义的并且其中Y和X是如表1中所定义的;化合物14.14对应于具有式(I-a)的化合物,其中R1、R3和R6是如表M的第14行中所定义的并且其中Y和X是如表14中所定义的;等等。
表M:
表1:此表披露了864种具有式(I-a)的化合物1.1至1.864,其中Y是5-甲基-1,2,4-噁二唑-3-基,X是氢并且R1、R3和R6是如表M中所定义的。例如,化合物编号1.1具有以下结构:
表2:此表披露了864种具有式(I-a)的化合物2.1至2.864,其中Y是1-甲基-1,2,4-三唑-3-基,X是氢并且R1、R3和R6是如表M中所定义的。
表3:此表披露了864种具有式(I-a)的化合物3.1至3.864,其中Y是3,5-二氯吡啶-2-基,X是氢并且R1、R3和R6是如表M中所定义的。
表4:此表披露了864种具有式(I-a)的化合物4.1至4.864,其中Y是3-氯-5-(三氟甲基)吡啶-2-基,X是氢并且R1、R3和R6是如表M中所定义的。
表5:此表披露了864种具有式(I-a)的化合物5.1至5.864,其中Y是苯基,X是氢并且R1、R3和R6是如表M中所定义的。
表6:此表披露了864种具有式(I-a)的化合物6.1至6.864,其中Y是苯基,X是羟基并且R1、R3和R6是如表M中所定义的。
表7:此表披露了864种具有式(I-a)的化合物7.1至7.864,其中Y是4-氯-苯基-1-基,X是氢并且R1、R3和R6是如表M中所定义的。
表8:此表披露了864种具有式(I-a)的化合物8.1至8.864,其中Y是4-氯-苯基-1-基,X是羟基并且R1、R3和R6是如表M中所定义的。
表9:此表披露了864种具有式(I-a)的化合物9.1至9.864,其中Y是甲基硫烷基甲基,X是氢并且R1、R3和R6是如表M中所定义的。
表10:此表披露了864种具有式(I-a)的化合物10.1至10.864,其中Y是甲基亚磺酰基甲基,X是氢并且R1、R3和R6是如表M中所定义的。
表11:此表披露了84种具有式(I-a)的化合物11.1至11.864,其中Y是甲基磺酰基甲基,X是氢并且R1、R3和R6是如表M中所定义的。
表12:此表披露了864种具有式(I-a)的化合物12.1至12.864,其中Y是乙基硫烷基甲基,X是氢并且R1、R3和R6是如表M中所定义的。
表13:此表披露了864种具有式(I-a)的化合物13.1至13.864,其中Y是乙基亚磺酰基甲基,X是氢并且R1、R3和R6是如表M中所定义的。
表14:此表披露了864种具有式(I-a)的化合物14.1至14.864,其中Y是乙基磺酰基甲基,X是氢并且R1、R3和R6是如表M中所定义的。
表15:此表披露了864种具有式(I-a)的化合物15.1至15.864,其中Y是1,1-二氧代-1,2-噻唑烷-2-基,X是氢并且R1、R3和R6是如表M中所定义的。
表16:此表披露了864种具有式(I-a)的化合物16.1至16.864,其中Y是(E)-甲氧基亚氨基甲基,X是氢并且R1、R3和R6是如表M中所定义的。
表17:此表披露了864种具有式(I-a)的化合物17.1至17.864,其中Y是(E)-乙氧基亚氨基甲基,X是氢并且R1、R3和R6是如表M中所定义的。
表18:此表披露了864种具有式(I-a)的化合物18.1至18.864,其中Y是N,N-二甲基-甲酰胺,X是氢并且R1、R3和R6是如表M中所定义的。
表19:此表披露了864种具有式(I-a)的化合物19.1至19.864,其中Y是甲磺酰胺基,X是氢并且R1、R3和R6是如表M中所定义的。
表20:此表披露了864种具有式(I-a)的化合物20.1至20.864,其中Y是氰基,X是氢并且R1、R3和R6是如表M中所定义的。
本发明的化合物的具体实例由式(I-b)示于下表21至35:
其中R1、R3和R6是如上在表M中所定义的。
下面的表21至35中的每一个包括864种具有式(I-b)的化合物,其中R1、R3和R6具有在表M的每一行中给出的值,并且A具有相关表21至35中给出的值。因此,化合物21.1对应于具有式(I-b)的化合物,其中R1、R3和R6是如表M的第1行中所定义的并且其中A是如表21中所定义的;化合物30.14对应于具有式(I-b)的化合物,其中R1、R3和R6是如表M的第14行中所定义的并且其中A是如表30中所定义的;等等。
表21:此表披露了864种具有式(I-b)的化合物21.1至21.864,其中A是3,5-二氯吡啶-2-基,并且R1、R3和R6是如表M中所定义的。例如,化合物编号1.1具有以下结构:
表22:此表披露了864种具有式(I-b)的化合物22.1至22.864,其中A是3-氯-5-(三氟甲基)吡啶-2-基,并且R1、R3和R6是如表M中所定义的。
表23:此表披露了864种具有式(I-b)的化合物23.1至23.864,其中A是3-氯-吡啶-2-基,并且R1、R3和R6是如表M中所定义的。
表24:此表披露了864种具有式(I-b)的化合物24.1至24 864,其中A是氰基,并且R1、R3和R6是如表M中所定义的。
表25:此表披露了864种具有式(I-b)的化合物25.1至25.864,其中A是氰基甲基并且R1、R3和R6是如表M中所定义的。
表26:此表披露了864种具有式(I-b)的化合物26.1至6.864,其中A是氰基乙基,并且R1、R3和R6是如表M中所定义的。
表27:此表披露了864种具有式(I-b)的化合物27.1至27.864,其中A是2,2,2-三氟乙基,并且R1、R3和R6是如表M中所定义的。
表28:此表披露了864种具有式(I-b)的化合物28.1至28.864,其中A是乙烯氧基羰基,并且R1、R3和R6是如表M中所定义的。
表29:此表披露了864种具有式(I-b)的化合物29.1至29.864,其中A是叔丁氧基羰基并且R1、R3和R6是如表M中所定义的。
表30:此表披露了864种具有式(I-b)的化合物30.1至30.864,其中A是4-氟-苯基,并且R1、R3和R6是如表M中所定义的。
表31:此表披露了84种具有式(I-b)的化合物31.1至31.864,其中A是4-氯-苯基,并且R1、R3和R6是如表M中所定义的。
表32:此表披露了864种具有式(I-b)的化合物32.1至32.864,其中A是2,4-二氯-苯基,并且R1、R3和R6是如表M中所定义的。
表33:此表披露了864种具有式(I-b)的化合物33.1至33.864,其中A是乙基硫烷基乙基,并且R1、R3和R6是如表M中所定义的。
表34:此表披露了864种具有式(I-b)的化合物34.1至34.864,其中A是乙基亚磺酰基乙基,并且R1、R3和R6是如表M中所定义的。
表35:此表披露了864种具有式(I-b)的化合物35.1至35.864,其中A是乙基磺酰基乙基,并且R1、R3和R6是如表M中所定义的。
还使得可获得具有式III、V、VI的某些中间体化合物,其中的一些是新颖的。
因此,本文中使得可获得:
具有式III-a的化合物
其中R1、R3和R6是在表M的每一行中所定义的并且R4是氢或R1、R3和R6是在表M的每一行中所定义的并且R4是氰基;
V-a的化合物
其中R1、R3和R6是在表M的每一行中所定义的并且R4是氢或R1、R3和R6是在表M的每一行中所定义的并且R4是氰基;
VI-a的化合物
其中R1、R3和R6是在表M的每一行中所定义的,R4是氢并且R12选自甲基、乙基、丙基、异丙基、丁基、异丁基和叔丁基。或R1、R3和R6是在表M的每一行中所定义的,R4是氰基并且R12选自甲基、乙基、丙基、异丙基、丁基、异丁基和叔丁基;
具有式IV-aa的化合物
其中X和Y是如在表1至20中任一个中所定义的;以及
具有式IV-ba的化合物
其中A是如在表21至35中任一个中所定义的。
在另一方面,因此,本发明使得可获得具有式III、V和VI的化合物,其中在每种情况下,R1、R2、R3、R4和R5是如在第一方面中对于式I所定义的,并且对于式VI,R12是C1-C6-烷基。此外,对于式I说明的R1、R2、R3、R4和R5的相应实施例也适用于具有式III、V和VI的化合物。对于式VI,R12优选地是甲基、乙基或丙基;更优选甲基。
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。根据本发明的活性成分作用于所有或个别发育阶段的通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)。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现出来,即,立即或仅在过去一些时间之后(例如在蜕皮期间)发生对有害生物的破坏;或间接显现出来,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.)、柑桔皱叶刺节蜱(Phyllocoptruta oleivora)、植食螨属物种(Phytonemus spp)、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(Rhizoglyphusspp.)、疥螨属物种(Sarcoptes spp.)、狭跗线螨属物种(Steneotarsonemus spp)、跗线螨属物种(Tarsonemus spp.)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(Drosophila melanogaster)、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)、Aleurodes物种、土黄缘蝽(Amblypelta nitida)、海虾盾缘蝽(Bathycoelia thalassina)、土长蝽属物种、臭虫属物种、Clavigrallatomentosicollis、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(Scaptocoriscastanea)、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、南美玉米苗斑螟(Elasmopalpus lignosellus)、甘薯杆螟、粉斑螟属物种、叶小卷蛾属物种(Epinotia spp)、盐泽灯蛾(Estigmene acrea)、Etiellazinckinella、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、Feltiajaculiferia、小食心虫属物种(Grapholita spp.)、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(Malacosoma spp.)、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(Rachiplusianu)、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)。
在另一方面中,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.)。
本发明的化合物还具有针对软体动物的活性。其实例包括例如福寿螺科;蛞蝓科(Arion)(黑蛞蝓(A.ater)、环状蛞蝓(A.circumscriptus)、棕阿勇蛞蝓(A.hortensis)、红蛞蝓(A.rufus));巴蜗牛科(Bradybaenidae)(灌木巴蜗牛(Bradybaena fruticum));葱蜗牛属(Cepaea)(花园葱蜗牛(C.hortensis)、森林葱蜗牛(C.Nemoralis));奥克洛迪纳(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));由木非来(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);黑力扣迪斯克(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,适合的目标作物是谷物,如小麦、大麦、黑麦、燕麦、稻、玉米或高梁;甜菜,如糖用甜菜或饲料甜菜;水果,例如梨果、核果或无核小果,如苹果、梨、李子、桃、杏、樱桃或浆果,例如草莓、覆盆子或黑莓;豆科作物,如菜豆、小扁豆、豌豆或大豆;油料作物,如油菜、芥菜、罂粟、橄榄、向日葵、椰子、蓖麻、可可豆或落花生;瓜类作物,如南瓜、黄瓜或甜瓜;纤维植物,如棉花、亚麻、大麻或黄麻;柑橘类水果,如橙子、柠檬、葡萄柚或橘子;蔬菜,如菠菜、莴苣、芦笋、卷心菜、胡萝卜、洋葱、番茄、马铃薯或灯笼椒;樟科,如鳄梨、肉桂或樟脑;以及还有烟草、坚果、咖啡、茄子、甘蔗、荼、胡椒、葡萄藤、蛇麻草、车前草科以及乳胶植物。
在具体实施例中,具有式(I)的化合物控制选自蔬菜(尤其是番茄和葫芦)、柑橘、仁果、核果、坚果、棉花、热带作物、鳄梨、观赏植物、菜豆、大豆、草莓和葡萄的作物、树木和植物中的螨、锈螨和叶螨。
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)、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(Betavulgarus)、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、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(African violet)、秋海棠属、大丽花属、大丁草属、绣球属、马鞭草属、蔷薇属、伽蓝菜属、一品红属、紫菀属、矢车菊属、金鸡菊属、翠雀属、美国薄荷属、草夹竹桃属、黄雏菊属、景天属、碧冬茄属、堇菜属、凤仙花属、老鹳草属、菊属、毛茛属、倒挂金钟属、鼠尾草属、绣球花属、迷迭香、鼠尾草、圣约翰草(St.Johnswort)、薄荷(mint)、甜椒(sweet pepper)、番茄和黄瓜(cucumber)。
根据本发明的活性成分尤其适合用于控制棉花、蔬菜、玉米、水稻以及大豆作物上的扁豆蚜、黄瓜条叶甲、烟芽夜蛾、桃蚜、小菜蛾以及海灰翅夜蛾。根据本发明的活性成分另外尤其适合用于控制甘蓝夜蛾(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)的化合物特别适合用于控制螨、叶螨和锈螨,例如,蜂盾螨属物种;武氏蜂盾螨;粗脚粉螨;粉螨属物种;柑橘瘤瘿螨;桔刺皮节蜱;刺皮节蜱属物种;斯氏针刺瘿螨;针刺瘿螨属物种;伪钝绥螨;短须螨属物种;紫红短须螨;苜蓿苔螨;果苔螨;嗜木螨属物种;布氏姬螯螨;姬螯螨属物种;亚斯格姬螯螨;牛皮痒螨;皮螨属物种;胞螨属物种;牛蠕形螨;Demodex caballi;犬蠕形螨;山羊蠕形螨;马蠕形螨;绵羊蠕形螨;蠕形螨属物种;猪蠕形螨;鸡皮刺螨;皮刺螨属物种;始叶螨属物种;魏始叶螨(Eotetranychus willamettei);梨上瘿螨;茶藨瘿螨;瘿螨属物种;葡萄瘿螨;真叶螨属物种;红足土螨(Halotydeusdestructor);半跗线螨属物种;鸟疥螨属物种;鸡雏螨属物种;牦螨属物种;肉螨属物种;Neoschongastia xerothermobia;秋收恙螨;Neotrombicula desaleri;猫耳螨;耳螨属物种;咖啡小爪螨;冬青小爪螨(Oligonychus ilicis);小爪螨属物种;禽螯螨属物种;囊禽刺螨;禽刺螨属物种;林禽刺螨;耳痒螨;耳痒螨属物种;桔全爪螨;全爪螨属物种;苹果全爪螨;柑桔皱叶刺节蜱;皱叶刺节蜱属物种;小植绥螨属物种;犬拟肺刺螨(Pneumonyssoidescaninum);侧多食跗线螨;多食跗线螨属物种;绵羊疮螨;疮螨属物种;兔痒螨;马痒螨;绵羊痒螨;痒螨属物种;翅螨属物种;刺利螨属物种;根螨属物种;牛疥螨;狗疥螨;山羊疥螨;马疥螨;绵羊疥螨;岩羚羊疥螨(Sarcoptes rupicaprae);疥螨属物种;猪疥螨;斯氏狭跗线螨;狭跗线螨属物种;胸刺螨属物种;跗线螨属物种;朱砂叶螨;神泽氏叶螨;叶螨属物种;二点叶螨;红恙螨;恙螨属物种;西方盲走螨;食酪螨属物种;雅氏瓦螨;瓦螨属物种;番茄刺皮瘿螨(Vasates lycopersici);以及苹果寻螨(Zetzellia mali)。
在实施例中,具有式(I)的化合物尤其适合用于控制以下中的一种或多种:柑橘瘤瘿螨;番茄针刺瘿螨(Aculus lycopersici);皮氏针刺瘿螨;斯氏针刺瘿螨;紫红短须螨;短须螨属物种;果苔螨;鹅耳枥始叶螨;始叶螨属物种;梨上瘿螨;Eriophyes piri;瘿螨属物种;葡萄瘿螨;非洲真叶螨;东方真叶螨;草地小爪螨;桔全爪螨;苹果全爪螨;葡萄锈螨;柑桔皱叶刺节蜱;侧多食跗线螨;朱砂叶螨;神泽氏叶螨;叶螨属物种;以及二点叶螨。
在另一个实施例中,具有式(I)的化合物更尤其适合用于控制以下中的一种或多种:柑橘瘤瘿螨;皮氏针刺瘿螨;紫红短须螨;短须螨属物种;Eriophyes piri;葡萄瘿螨;非洲真叶螨;东方真叶螨;草地小爪螨;苹果全爪螨;葡萄锈螨;柑桔皱叶刺节蜱;侧多食跗线螨;朱砂叶螨;神泽氏叶螨;叶螨属物种;以及二点叶螨。
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,例如来自蜡样芽孢杆菌或日本金龟子芽孢杆菌的杀昆虫蛋白;或者来自苏云金芽孢杆菌的杀昆虫蛋白,如δ-内毒素,例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C,或者营养期杀昆虫蛋白(Vip),例如Vip1、Vip2、Vip3或Vip3A;或细菌定植线虫的杀昆虫蛋白,例如光杆状菌属物种(Photorhabdus spp.)或致病杆菌属物种(Xenorhabdus spp.),如发光杆菌(Photorhabdus luminescens)、嗜线虫致病杆菌(Xenorhabdus nematophilus);由动物产生的毒素,如蝎毒素、蛛毒素、蜂毒素和其他昆虫特异性神经毒素;由真菌产生的毒素,如链霉菌毒素,植物凝集素类(lectin),如豌豆凝集素、大麦凝集素或雪花莲凝集素;凝集素(agglutinin);蛋白酶抑制剂,如胰蛋白酶抑制剂、丝蛋白酶抑制剂、马铃薯糖蛋白、胱抑素、木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),如蓖麻毒素、玉蜀黍-RIP、相思豆毒素、丝瓜籽毒蛋白、皂草毒素蛋白或异株泻根毒蛋白;类固醇代谢酶,如3-羟基类固醇氧化酶、蜕化类固醇-UDP-糖基-转移酶、胆固醇氧化酶、蜕化素抑制剂、HMG-COA-还原酶、离子通道阻断剂如钠通道或钙通道阻断剂、保幼激素酯酶、利尿激素受体、芪合酶、联苄合酶、几丁质酶和葡聚糖酶。
在本发明的背景下,δ-内毒素(例如Cry1Ab、Cry1Ac、Cry1F、Cry1Fa2、Cry2Ab、Cry3A、Cry3Bb1或Cry9C)或营养期杀昆虫蛋白(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替代。在这种氨基酸替代中,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于例如以上提及的公开物中。CryI型脱氧核糖核酸及其制备例如从WO 95/34656、EP-A-0 367474、EP-A-0 401 979和WO 90/13651中已知。
包含在转基因植物中的毒素使得植物对有害昆虫有耐受性。此类昆虫可以存在于任何昆虫分类群,但尤其常见于甲虫(鞘翅目)、双翅昆虫(双翅目)和蛾(鳞翅目)。
包含一种或多种编码杀昆虫剂抗性并且表达一种或多种毒素的基因的转基因植物是已知的并且其中一些是可商购的。此类植物的实例是:YieldGard(玉米品种,表达Cry1Ab毒素);YieldGard Rootworm(玉米品种,表达Cry3Bb1毒素);YieldGard Plus(玉米品种,表达Cry1Ab和Cry3Bb1毒素);Starlink(玉米品种,表达Cry9C毒素);Herculex I(玉米品种,表达Cry1Fa2毒素和获得对除草剂草铵膦铵的耐受性的酶膦丝菌素N-乙酰基转移酶(PAT));NuCOTN 33B(棉花品种,表达Cry1Ac毒素);Bollgard I(棉花品种,表达Cry1Ac毒素);Bollgard II(棉花品种,表达Cry1Ac和Cry2Ab毒素);VipCot(棉花品种,表达Vip3A和Cry1Ab毒素);NewLeaf(马铃薯品种,表达Cry3A毒素);NatureGard、AgrisureGT Advantage(GA21耐草甘膦性状)、AgrisureCB Advantage(Bt11玉米螟(CB)性状)以及Protecta。
此类转基因作物的另外的实例是:
1.Bt11玉米,来自先正达种子公司(Syngenta Seeds SAS),霍比特路(Chemin del'Hobit)27,F-31 790圣苏维尔(St.Sauveur),法国,登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达截短的Cry1Ab毒素,使其能抵抗欧洲玉米螟(玉米螟和粉茎螟)的攻击。Bt11玉米还转基因表达PAT酶以获得对除草剂草铵膦铵盐的耐受性。
2.Bt176玉米,来自先正达种子公司,霍比特路27,F-31 790圣苏维尔,法国,登记号C/FR/96/05/10。遗传修饰的玉蜀黍,通过转基因表达Cry1Ab毒素,使其能抵抗欧洲玉米螟(玉米螟和粉茎螟)的攻击。Bt176玉米还转基因表达酶PAT以获得对除草剂草铵膦的耐受性。
3.MIR604玉米,来自先正达种子公司,霍比特路27,F-31 790圣苏维尔,法国,登记号C/FR/96/05/10。通过转基因表达经修饰的Cry3A毒素使其具有昆虫抗性的玉米。此毒素是通过插入组织蛋白酶-G-蛋白酶识别序列而经修饰的Cry3A055。此类转基因玉米植物的制备描述于WO 03/018810中。
4.MON 863玉米,来自孟山都欧洲公司(Monsanto Europe S.A.)270-272特弗伦大道(Avenue de Tervuren),B-1150布鲁塞尔,比利时,登记号C/DE/02/9。MON 863表达Cry3Bb1毒素,并且对某些鞘翅目昆虫有抗性。
5.IPC 531棉花,来自孟山都欧洲公司270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/ES/96/02。
6.1507玉米,来自先锋海外公司(Pioneer Overseas Corporation),特德斯科大道(Avenue Tedesco),7B-1160布鲁塞尔,比利时,登记号C/NL/00/10。遗传修饰的玉米,表达蛋白质Cry1F以获得对某些鳞翅目昆虫的抗性,并且表达PAT蛋白质以获得对除草剂草铵膦的耐受性。
7.NK603×MON 810玉米,来自孟山都欧洲公司270-272特弗伦大道,B-1150布鲁塞尔,比利时,登记号C/GB/02/M3/03。通过将遗传修饰的品种NK603和MON 810杂交,由常规育种的杂交玉米品种构成。NK603×MON 810玉米转基因表达由土壤杆菌属物种(Agrobacterium sp.)菌株CP4获得的蛋白CP4 EPSPS(使其耐受除草剂Roundup(含有草甘膦))以及还有由苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensissubsp.kurstaki)获得的Cry1Ab毒素(使其耐受某些鳞翅目昆虫,包括欧洲玉米螟)。
抗昆虫的植物的转基因作物还描述于BATS(生物安全与可持续发展中心(Zentrumfür Biosicherheit und Nachhaltigkeit),BATS中心(Zentrum BATS),克拉斯崔舍(Clarastrasse)13,4058巴塞尔(Basel),瑞士)报告2003(http://bats.ch)中。
术语“作物”应理解为还包括已经通过使用重组DNA技术而被这样转化使其能够合成具有选择性作用的抗病原物质的作物植物,这些抗病原物质是例如像所谓的“病程相关蛋白”(PRP,参见例如EP-A-0 392 225)。此类抗病原物质和能够合成此类抗病原物质的转基因植物的实例例如从EP-A-0 392 225、WO 95/33818和EP-A-0 353191中已知。生产此类转基因植物的方法通常是本领域技术人员已知的并且描述于例如以上提及的公开物中。
作物也可以经修饰以增强对真菌(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)具有增强的抗性的那些作物。
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、霜或光辐射具有增强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质或多肽因子(所谓的“植物疾病抗性基因”,如WO 03/000906中所述)。
根据本发明的组合物的另外的使用领域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,用于控制动物的体表寄生虫。本发明进一步提供了第一方面的化合物,用于预防和/或治疗由体表寄生虫传播的疾病。
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表寄生虫的药物的用途。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/或治疗由体表寄生虫传播的疾病的药物的用途。
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表寄生虫中的用途。
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。“体表寄生虫”是生活在宿主动物体表的寄生虫。体表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);以及钝缘蜱属(Ornithodoros)。螨包括但不限于以下属的成员:皮螨属(Chorioptes),例如牛皮痒螨(Chorioptes bovis);痒螨属(Psoroptes),例如绵羊痒螨(Psoroptes ovis);姬螯螨属(Cheyletiella);皮刺螨属(Dermanyssus);例如鸡皮刺螨(Dermanyssus gallinae);禽刺螨属(Ortnithonyssus);蠕形螨属(Demodex),例如犬蠕形螨(Demodex canis);疥螨属(Sarcoptes),例如人疥螨(Sarcoptes scabiei);以及疮螨属(Psorergates)。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(Ctenocephalides felis)和犬栉头蚤(Ctenocephatides canis)。双翅目的成员包括但不限于蝇属物种(Musca spp.);肤蝇,例如马蝇(Gasterophilusintestinalis)和羊狂蝇(Oestrus ovis);螫蝇(biting flies);虻,例如麻虻属物种(Haematopota spp.)和Tabunus物种;黑角蝇属(haematobia),例如扰血蝇(haematobiairritans);螫蝇属(Stomoxys);绿蝇属(Lucilia);蠓;以及蚊。毛虱目类的成员包括但不限于吸血虱和嚼虱(chewing lice),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”是指本发明的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;所选定的给药方案;伴随药物的使用;以及其他相关情况。
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。适合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众所周知的。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 Proceduresfor Pharmaceutical New Chemical Entities[制药新化学实体的盐选择和最优化程序]”,Organic Process Research and Development[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 ofPharmaceutical Sciences[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众所周知的技术和条件,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(如蚊科和其他疾病载体)的方法;同样参见http://www.who.int/malaria/vector_control/irs/en/)。在一个实施例中,用于控制有害生物的方法包括通过涂刷、轧制、喷雾、涂布或浸渍,向目标有害生物、它们的场所或表面或基底施用本发明的组合物。通过举例,通过本发明的方法考虑到了表面(如墙、天花板或地板表面)的IRS(室内残留喷雾)施用。在另一个实施例中,考虑到了将此类组合物施用于如下基底,如无纺或织物材料,该材料处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中)。
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残留的杀有害生物活性。此种施用可以通过涂刷、轧制、喷雾、涂布或浸渍本发明的杀有害生物组合物来进行。通过举例,通过本发明的方法考虑到了表面(如墙、天花板或地板表面)的IRS施用,以便于在该表面上提供有效的残留的杀有害生物活性。在另一个实施例中,考虑了施用此类组合物以用于在基底上的有害生物的残留控制,该基底是如处于网织品、被覆物、被褥、窗帘以及帐篷的形式(或可以用于在这些物品的制造中)的织物材料。
有待处理的基底(包括无纺物、织物或网织品)可以由天然纤维,如棉花、拉菲亚树叶纤维、黄麻、亚麻、剑麻、粗麻布或羊毛,或者合成纤维,如聚酰胺、聚酯、聚丙烯、聚丙烯腈等等制成。聚酯是特别适合的。纺织品处理的方法是已知的,例如WO 2008/151984、WO2003/034823、US 5631072、WO 2005/64072、WO 2006/128870、EP 1724392、WO 2005113886或WO 2007/090739。
根据本发明的组合物的另外的使用领域是针对所有观赏树木连同所有种类的果树和坚果树的树木注射/树干处理领域。
在树木注射/树干处理领域中,根据本发明的化合物尤其适合于对抗来自如上提及的鳞翅目和来自鞘翅目的蛀木昆虫,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摄食草坪草的根部的昆虫有害生物,包括蛴螬(如圆头犀金龟属物种(Cyclocephala spp.)(例如标记的金龟子、C.lurida)、Rhizotrogus属物种(例如欧洲金龟子,欧洲切根鳃金龟(R.majalis))、黄栌属物种(Cotinus spp.)(例如绿六月甲虫(Green June beetle)、绿六月花金龟(C.nitida))、弧丽金龟属物种(Popilliaspp.)(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(Ataenius)物种(例如草坪草黑金龟(Black turfgrassataenius)、黑绒金龟(A.spretulus))、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(M.castanea))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取食草坪草叶子的草坪草中的昆虫有害生物,这些昆虫有害生物包括麦小蝽(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有效地对抗体表寄生虫如硬蜱、软蜱、疥螨、秋螨、蝇(叮咬和舔舐)、寄生性蝇幼虫,虱、发虱、鸟虱和跳蚤。
此类寄生虫的实例是:
虱目:血虱属物种、长颚虱属物种(Linognathus spp.)、人虱属物种以及阴虱属物种(Phtirus spp.)、管虱属物种。
食毛目:毛羽虱属物种、短羽虱属物种、鸭虱属物种、牛羽虱属物种、Werneckiella属物种、Lepikentron属物种、畜虱属物种、啮毛虱属物种以及猫羽虱属物种(Felicolaspp.)。
双翅目及长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属物种(Aedes spp.)、疟蚊属物种、库蚊属物种(Culex spp.)、蚋属物种(Simulium spp.)、真蚋属物种(Eusimulium spp.)、白蛉属物种(Phlebotomus spp.)、罗蛉属物种(Lutzomyiaspp.)、库蠓属物种(Culicoides spp.)、斑虻属物种(Chrysops spp.)、驼背虻属物种(Hybomitra spp.)、黄虻属物种(Atylotus spp.)、虻属物种(Tabanus spp.)、麻虻属物种(Haematopota spp.)、Philipomyia属物种、蜂虱蝇属物种(Braula spp.)、家蝇属物种(Musca spp.)、齿股蝇属物种(Hydrotaea spp.)、螫蝇属物种、黑角蝇属物种(Haematobiaspp.)、莫蝇属物种(Morellia spp.)、厕蝇属物种(Fannia spp.)、舌蝇属物种(Glossinaspp.)、丽蝇属物种(Calliphora spp.)、绿蝇属物种(Lucilia spp.)、金蝇属物种(Chrysomyia spp.)、污蝇属物种(Wohlfahrtia spp.)、麻蝇属物种(Sarcophaga spp.)、狂蝇属物种(Oestrus spp.)、皮蝇属物种(Hypoderma spp.)、胃蝇属物种(Gasterophilusspp.)、虱蝇属物种(Hippobosca spp.)、羊虱蝇属物种(Lipoptena spp.)和蜱蝇属物种(Melophagus spp.)。
蚤目(Siphonapterida),例如蚤属物种(Pulex spp.)、栉头蚤属物种、客蚤属物种(Xenopsylla spp.)、角叶蚤属物种。
异翅目(Heteropterida),例如臭虫属物种、锥鼻虫属物种、红猎蝽属物种、锥蝽属物种(Panstrongylus spp.)。
蜚蠊目(Blattarida),例如东方蜚蠊(Blatta orientalis)、美洲大蠊(Periplaneta americana)、德国小蠊(Blattelagermanica)以及夏柏拉蟑螂属物种(Supella spp.)。
蜱螨(Acaria)亚纲(螨科(Acarida))和后气门目(Meta-stigmata)和中气门目(Meso-stigmata),例如锐缘蜱属物种(Argas spp.)、钝缘蜱属物种(Ornithodorus spp.)、耳蜱属物种(Otobius spp.)、硬蜱属物种(Ixodes spp.)、钝眼蜱属物种(Amblyommaspp.)、牛蜱属物种(Boophilus spp.)、革蜱属物种(Dermacentor spp.)、血蜱属物种(Haemophysalis spp.)、璃眼蜱属物种(Hyalomma spp.)、扇头蜱属物种(Rhipicephalusspp.)、皮刺螨属物种(Dermanyssus spp.)、刺利螨属物种(Raillietia spp.)、肺刺螨属物种(Pneumonyssus spp.)、胸刺螨属物种(Sternostoma spp.)和瓦螨属物种(Varroaspp.)。
轴螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨目(Acaridida)(无气门亚目(Astigmata)),例如蜂盾螨属物种(Acarapis spp.)、姬螯螨属物种(Cheyletiellaspp.)、禽螯螨属物种(Ornithocheyletia spp.)、肉螨属物种(Myobia spp.)、疮螨属物种(Psorergates spp.)、蠕形螨属物种(Demodex spp.)、恙螨属物种(Trombicula spp.)、牦螨属物种(Listrophorus spp.)、粉螨属物种(Acarus spp.)、食酪螨属物种(Tyrophagusspp.)、嗜木螨属物种(Caloglyphus spp.)、颈下螨属物种(Hypodectes spp.)、翅螨属物种(Pterolichus spp.)、痒螨属物种(Psoroptes spp.)、皮螨属物种(Chorioptes spp.)、耳痒螨属物种(Otodectes spp.)、疥螨属物种(Sarcoptes spp.)、耳螨属物种(Notoedresspp.)、鸟疥螨属物种(Knemidocoptes spp.)、胞螨属物种(Cytodites spp.)以及鸡雏螨属物种(Laminosioptes spp.)。
根据本发明的组合物还适用于保护在如木材、纺织品、塑料、粘合剂、胶、漆料、纸张和卡片、皮革、地板和建筑等情况下的材料免受昆虫侵染。
根据本发明的组合物可以用于,例如,对抗以下有害生物:甲虫,如北美家天牛(Hylotrupes bajulus)、长毛天牛(Chlorophorus pilosis)、家具窃蠹(Anobiumpunctatum)、红毛窃蠹(Xestobium rufovillosum)、梳角细脉窃蠹(Ptilinuspecticornis)、Dendrobium pertinex、松芽枝窃蠹(Ernobius mollis)、Priobium carpini、褐粉蠹(Lyctus brunneus)、非洲粉蠹(Lyctus africanus)、南方粉蠹(Lyctus planicollis)、栎粉蠹(Lyctus linearis)、柔毛粉蠹(Lyctus pubescens)、胸粉蠹(Trogoxylon aequale)、鳞毛粉蠹(Minthesrugicollis)、材小蠹属物种(Xyleborusspec.)、条木小蠹属物种(Tryptodendron spec.)、咖啡黑长蠹(Apate monachus)、槲长蠹(Bostrychus capucins)、棕异翅长蠹(Heterobostrychus brunneus)、双棘长蠢属物种(Sinoxylon spec.)以及竹长蠹(Dinoderus minutus),以及还有膜翅类,如蓝黑树蜂(Sirex juvencus)、大树蜂(Urocerus gigas)、泰加大树蜂(Urocerus gigas taignus)和Urocerus augur;白蚁类,如欧洲木白蚁(Kalotermes flavicollis)、麻头堆砂白蚁(Cryptotermes brevis)、印巴结构木异白蚁(Heterotermes indicola)、黄胸散白蚁(Reticulitermes flavipes)、桑特散白蚁(Reticulitermes santonensis)、欧洲散白蚁(Reticulitermes lucifugus)、达尔文澳白蚁(Mastotermes darwiniensis)、内华达古白蚁(Zootermopsis nevadensis)和家白蚁(Coptotermes formosanus);以及蛀虫,如衣鱼(Lepisma saccharina)。具有式I和I'a的化合物或其盐尤其适合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1至35和表P1至P8中定义的化合物中的一种化合物”)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合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1至35和表P1至P8中定义的化合物中的一种化合物”)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合用于控制以下项中的一种或多种: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1至35和表P1至P8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,来自表1至35和表P1至P8的一种化合物适合用于控制棉花、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,来自表1至35和表P1至P8的一种化合物适合用于控制甘蓝夜蛾(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许多益处,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目标生物体(如鱼、鸟和蜂))、改进的物理-化学特性、或增加的生物可降解性)。特别地,已经出人意料地发现某些具有式(I)的化合物相对于非目标节肢动物,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,相对于意大利蜂(Apis mellifera)。
根据本发明的化合物可以按未经修饰的形式用作杀有害生物剂,但它们通常以多种方式使用配制辅助剂(如载体、溶剂以及表面活性物质)被配制成组合物。这些配制品可以处于不同的实体形式,例如,处于以下形式:撒粉剂、凝胶、可湿性粉剂、水可分散性颗粒剂、水可分散性片剂、泡腾压缩片剂、可乳化的浓缩物、微可乳化浓缩物、水包油乳剂、可流动油、水性分散体、油性分散体、悬乳剂、胶囊悬浮液、可乳化的颗粒剂、可溶性液体、水可溶性浓缩物(以水或水混溶性有机溶剂作为载体)、浸渍的聚合物膜或处于已知的其他形式,例如从Manual on Development and Use of FAO and WHO Specifications forPesticides[关于杀有害生物剂的FAO和WHO标准的发展和使用的手册],联合国,第1版,二次修订(2010)中已知的。此类配制品可以直接使用或者可以使用前稀释再使用。可以用例如水、液体肥料、微量营养素、生物有机体、油或溶剂来进行稀释。
可以通过例如将活性成分与配制辅助剂混合来制备这些配制品以便获得处于精细分散固体、颗粒、溶液、分散体或乳剂形式的组合物。这些活性成分还可以与其他辅助剂(如精细分散固体、矿物油、植物或动物来源的油、改性的植物或动物来源的油、有机溶剂、水、表面活性物质或其组合)一起配制。
这些活性成分还可以被包含于非常精细的微胶囊中。微胶囊在多孔载体中含有活性成分。这使得活性成分能够以受控的量释放(例如,缓慢释放)到环境中。微胶囊通常具有从0.1至500微米的直径。它们包含的活性成分的量按重量计是胶囊重量的约从25%至95%。这些活性成分可以处于整体性的固体的形式、处于固体或液体分散体中的精细颗粒的形式或处于适合溶液的形式。包囊的膜可以包含例如天然的或合成的橡胶、纤维素、苯乙烯/丁二烯共聚物、聚丙烯腈、聚丙烯酸酯、聚酯、聚酰胺、聚脲、聚氨酯或化学改性的聚合物以及淀粉黄原酸酯、或本领域的技术人员已知的其他聚合物。可替代地,可以形成非常精细的微胶囊,其中活性成分在基础物质的固体基质中是以精细分散颗粒的形式被包含的,但这些微胶囊本身未经包裹。
适合用于制备根据本发明的组合物的配制辅助剂本身是已知的。作为液体载体可以使用:水、甲苯、二甲苯、石油醚、植物油、丙酮、甲基乙基酮、环己酮、酸酐、乙腈、乙酰苯、乙酸戊酯、2-丁酮、碳酸丁烯酯、氯苯、环己烷、环己醇、乙酸烷基酯、二丙酮醇、1,2-二氯丙烷、二乙醇胺、对-二乙基苯、二甘醇、松脂酸二乙二醇酯、二甘醇丁基醚、二甘醇乙基醚、二甘醇甲醚、N,N-二甲基甲酰胺、二甲基亚砜、1,4-二噁烷、二丙二醇、二丙二醇甲基醚、双丙甘醇二苯甲酸酯、二丙二醇、烷基吡咯烷酮、乙酸乙酯、2-乙基己醇、碳酸乙烯酯、1,1,1-三氯乙烷、2-庚酮、α-蒎烯、d-苧烯、乳酸乙酯、乙二醇、乙二醇丁基醚、乙二醇甲基醚、γ-丁内酯、丙三醇、乙酸甘油酯、二乙酸甘油酯、三乙酸甘油酯、十六烷、己二醇、乙酸异戊基酯、乙酸异冰片基酯、异辛烷、异佛尔酮、异丙苯、肉豆蔻酸异丙酯、乳酸、月桂胺、异亚丙基丙酮、甲氧基丙醇、甲基异戊基酮、甲基异丁基酮、月桂酸甲酯、辛酸甲酯、油酸甲酯、二氯甲烷、间二甲苯、正己烷、正辛胺、十八烷酸、辛胺乙酸酯、油酸、油烯基胺、邻二甲苯、苯酚、聚乙二醇、丙酸、乳酸丙酯、碳酸亚丙酯、丙二醇、丙二醇甲基醚、对-二甲苯、甲苯、磷酸三乙酯、三乙二醇、二甲苯磺酸、石蜡、矿物油、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、丙二醇甲基醚、二乙二醇甲基醚、甲醇、乙醇、异丙醇以及更高分子量的醇,例如戊醇、四氢呋喃醇、己醇、辛醇、乙二醇、丙二醇、甘油、N-甲基-2-吡咯烷酮等。
适合的固体载体是例如滑石、二氧化钛、叶蜡石黏土、硅石、凹凸棒石黏土、硅藻土、石灰石、碳酸钙、膨润土、钙蒙脱土、棉籽壳、小麦粉、大豆粉、浮石、木粉、经研磨的胡桃壳、木质素和类似的物质。
许多表面活性物质可以有利地用在固体和液体配制品两者中,尤其是在使用前可被载体稀释的那些配制品中。表面活性物质可以是阴离子的、阳离子的、非离子的或聚合的并且它们可以用作乳化剂、湿润剂或悬浮剂或用于其他目的。典型的表面活性物质包括例如烷基硫酸酯的盐,如十二烷基硫酸二乙醇铵;烷基芳基磺酸酯的盐,如十二烷基苯磺酸钙;烷基酚/氧化烯加成产物,如乙氧基化壬基苯酚;醇/氧化烯加成产物,如乙氧基化十三烷醇;皂,如硬脂酸钠;烷基萘磺酸酯的盐,如二丁基萘磺酸钠;磺基琥珀酸二烷基酯的盐,如二(2-乙基己基)磺基琥珀酸钠;山梨糖醇酯,如山梨糖醇油酸酯;季铵,如氯化十二烷基三甲基铵;脂肪酸的聚乙二醇酯,如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;以及磷酸单烷基酯和二烷基酯的盐;以及还有另外的物质,例如描述于:McCutcheon'sDetergents and Emulsifiers Annual[麦卡琴清洁剂和乳化剂年鉴],MC出版公司(MCPublishing Corp.),里奇伍德,新泽西州(Ridgewood New Jersey)(1981)。
可以用于杀有害生物配制品的另外的辅助剂包括结晶抑制剂、粘度改性剂、悬浮剂、染料、抗氧化剂、发泡剂、光吸收剂、混合助剂、消泡剂、络合剂、中和或改变pH的物质和缓冲液、腐蚀抑制剂、香料、湿润剂、吸收增强剂、微量营养素、增塑剂、助流剂、润滑剂、分散剂、增稠剂、防冻剂、杀微生物剂、以及液体和固体肥料。
根据本发明的组合物可以包括添加剂,该添加剂包括植物或动物来源的油、矿物油、此类油的烷基酯或此类油与油衍生物的混合物。在根据本发明的组合物中的油添加剂的量通常是基于待施用的混合物从0.01%至10%。例如,可以在喷雾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雾罐中。优选的油添加剂包括矿物油或植物来源的油,例如菜籽油、橄榄油或葵花籽油;乳化的植物油;植物来源的油的烷基酯,例如甲基衍生物;或动物来源的油,如鱼油或牛脂。优选的油添加剂包括C8-C22脂肪酸的烷基酯,尤其是C12-C18脂肪酸的甲基衍生物,例如月桂酸、棕榈酸以及油酸的甲酯(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[除草剂辅助剂纲要],第10版,南伊利诺伊大学,2010中已知。
本发明组合物总体上包含按重量计从0.1%至99%,尤其是按重量计从0.1%至95%的本发明的化合物以及按重量计从1%至99.9%的配制辅助剂,该配制辅助剂优选地包括按重量计从0至25%的表面活性物质。而商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、以及受施用方法支配的其他因素如施用时间以及目标作物。一般来讲,可以将化合物以从1至2000l/ha、尤其是从10至1000l/ha的比率施用。
优选的配制品可以具有以下组成(重量%):
可乳化的浓缩物:
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了(但不限制)本发明。
<u>可湿性粉剂</u> | a) | b) | c) |
活性成分 | 25% | 50% | 75% |
木质素磺酸钠 | 5% | 5% | - |
月桂基硫酸钠 | 3% | - | 5% |
二异丁基萘磺酸钠 | - | 6% | 10% |
苯酚聚乙二醇醚(7-8mol的环氧乙烷) | - | 2% | - |
高度分散的硅酸 | 5% | 10% | 10% |
高岭土 | 62% | 27% | - |
将该组合与这些辅助剂充分混合并且将混合物在适合的研磨机中充分研磨,从而获得了可以用水稀释而给出所希望的浓度的悬浮液的可湿性粉剂。
将该组合与这些辅助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>可乳化的浓缩物</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% |
蓖麻油聚乙二醇醚(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从这种浓缩物获得。
<u>尘粉剂</u> | a) | b) | c) |
活性成分 | 5% | 6% | 4% |
滑石 | 95% | - | - |
高岭土 | - | 94% | - |
矿物填料 | - | - | 96% |
通过将该组合与载体混合并且将混合物在适合的研磨机中研磨而获得即用型尘粉剂。此类粉剂还可以用于种子的干拌种。
<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% |
将该组合与这些辅助剂混合并且研磨,并且将混合物用水湿润。
将混合物挤出并且然后在空气流中干燥。
将该精细研磨的组合在混合器中均匀地施用于用聚乙二醇湿润的高岭土中。以此方式获得无尘的包衣的颗粒剂。
悬浮液浓缩物
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(处于在水中75%的乳液的形式) | 1% |
水 | 32% |
将该精细研磨的组合与这些辅助剂紧密地混合,得到悬浮液浓缩物,从该悬浮液浓缩物可以通过用水稀释获得具有任何所希望的稀释度的悬浮液。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷雾、浇灌或浸渍进行保护。
种子处理用的可流动性浓缩物
活性成分 | 40% |
丙二醇 | 5% |
共聚物丁醇PO/EO | 2% |
三苯乙烯酚,具有10-20摩尔EO | 2% |
1,2-苯并异噻唑啉-3-酮(处于在水中20%的溶液形式) | 0.5% |
单偶氮-颜料钙盐 | 5% |
硅油(处于在水中75%的乳液的形式) | 0.2% |
水 | 45.3% |
将该精细研磨的组合与这些辅助剂紧密地混合,得到悬浮液浓缩物,从该悬浮液浓缩物可以通过用水稀释获得具有任何所希望的稀释度的悬浮液。使用此类稀释物,可以对活的植物连同植物繁殖材料进行处理并且对其针对微生物侵染通过喷雾、浇灌或浸渍进行保护。
缓释的胶囊悬浮液
将28份的组合与2份的芳香族溶剂以及7份的甲苯二异氰酸酯/多亚甲基-多苯基异氰酸酯-混合物(8:1)进行混合。将此混合物在1.2份的聚乙烯醇、0.05份的消泡剂以及51.6份的水的混合物中进行乳化直至达到所希望的粒度。向此乳液中添加在5.3份的水中的2.8份的1,6-己二胺混合物。将混合物搅拌直至聚合反应完成。将获得的胶囊悬浮液通过添加0.25份的增稠剂以及3份的分散剂进行稳定。胶囊悬浮液配制品含有28%的活性成分。介质胶囊的直径是8-15微米。将所得配制品作为适合用于此目的的装置中的水性悬浮液施用到种子上。
配制品类型包括乳液浓缩物(EC)、悬浮液浓缩物(SC)、悬乳液(SE)、胶囊悬浮液(CS)、水可分散性颗粒剂(WG)、可乳化的颗粒剂(EG)、乳剂、油包水型乳液(EO)、水包油型乳液(EW)、微乳液(ME)、油分散体(OD)、油悬剂(OF)、油溶性液剂(OL)、可溶性浓缩物(SL)、超低容量悬浮液(SU)、超低容量液剂(UL)、母药(TK)、可分散性浓缩物(DC)、可湿性粉剂(WP)、可溶性颗粒剂(SG)或与农业上可接受的辅助剂组合的任何技术上可行的配制品。
制备实例:
LCMS方法:
方法1:
光谱记录在来自沃特斯公司(Waters)的ZQ质谱仪(单四极杆质谱仪)上;
仪器参数:离子化方法:电喷射极性:正(负)离子;毛细管(kV)3.00,锥孔(V)30.00,萃取器(V)2.00,气体温度(℃)350,干燥气体流量(mL/min)9.8,等离子体气压力(Neb press)45psig,质量范围:90至1000Da。
LC:来自安捷伦公司(Agilent)的HP 1100 HPLC:溶剂脱气装置,四元泵(ZCQ)/二元泵(ZDQ),经加热的柱室以及二极管阵列检测器。柱:porpshell 120 C18,2.7μm粒度,120埃,4.6×50mm;温度:30℃。DAD波长范围(nm):190至400溶剂梯度:A=水+0.1%HCOOH。B=乙腈+0.08%HCOOH。
时间(min) | A% | B% | 流量(ml/min) |
0.00 | 85.0 | 15.0 | 0.6 |
4.00 | 5.00 | 95.00 | 0.6 |
10.00 | 5.00 | 95.00 | 0.6 |
方法2:
光谱记录在来自沃特斯公司的ACQUITY质谱仪(SQD或SQDII单四极杆质谱仪)上,其装备有电喷射源(极性:正离子或负离子,毛细管:3.0kV,锥孔:30V,萃取器:3.00V,源温度:150℃,去溶剂化温度:400℃,锥孔气体流量:60L/hr,去溶剂化气体流量:700L/hr,质量范围:140至800Da)和来自沃特斯公司的ACQUITY UPLC,其具有溶剂脱气装置、二元泵、经加热的柱室以及二极管阵列检测器。柱:Waters UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃,DAD波长范围(nm):210至400,溶剂梯度:A=水/甲醇9:1+0.1%甲酸,B=乙腈+0.1%甲酸,梯度:0%-100%B,在2.5min内;流量(ml/min)0.75。
方法3:
光谱记录在来自沃特斯公司的质谱仪(SQD、SQDII单四极杆质谱仪)上,其装备有电喷射源(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)和来自沃特斯公司的Acquity UPLC:二元泵、经加热的柱室、二极管阵列检测器和ELSD检测器。柱:Waters UPLC HSS T3,1.8μm,30×2.1mm,温度:60℃,DAD波长范围(nm):210至500,溶剂梯度:A=水+5%MeOH+0.05%HCOOH,B=乙腈+0.05%HCOOH;梯度:10%-100%B,在1.2min内;流量(ml/min)0.85。
下面的实验描述中使用了以下缩写:s=单峰,d=二重峰,t=三重峰,q=四重峰,m=多重峰,RT=保留时间,min=分钟。
实例P1:5-[4-(5-甲基-1,2,4-噁二唑-3-基)哌啶-1-羰基]-4-(三氟甲基)-2-[4-
(三氟甲基)苯基]苯甲腈(化合物P1.1):
步骤1:4-羟基-5-碘-2-(三氟甲基)苯甲酸甲酯
将4-羟基-2-(三氟甲基)苯甲酸甲酯(10.5g,47.7mmol)、碘(18.0g,70.9mmol)和碳酸钾(13.2g,95.5mmol)添加到THF(150mL)中。将反应混合物在回流下加热16小时。然后添加硫代硫酸钠溶液。将混合物用乙酸乙酯萃取,并且将有机相用盐水洗涤三次。蒸发溶剂并将残余物通过色谱法(石油醚:乙酸乙酯=5:1)纯化以得到白色固体(6.90g,41.8%)。DMSO-d6中的1H-NMR[ppm]:11.75(s,1H),8.23(s,1H),7.23(s,1H),3.81(s,3H)。LC-MS(方法1):RT=4.34min;[M-H]-=344.9。
步骤2:5-氰基-4-羟基-2-(三氟甲基)苯甲酸甲酯
将4-羟基-5-碘-2-甲基-苯甲酸甲酯(2.50g,8.56mmol)和氰化铜(I)(1.94g,21.7mmol)在1-甲基吡咯烷-2-酮(20mL)中在110℃下搅拌12小时。将混合物倒入水中并用乙酸乙酯(50mL)萃取,经Na2SO4干燥,过滤并在真空下浓缩。将粗产物通过硅胶柱色谱法(乙酸乙酯/石油醚=1/5)纯化以得到白色固体(1.30g,73.4%)。DMSO-d6中的1H-NMR[ppm]:12.75(bs,1H),8.23(s,1H),7.40(s,1H),3.83(s,3H)。LC-MS(方法1):RT=3.88min;[M-H]-=244。
步骤3:5-氰基-2-(三氟甲基)-4-(三氟甲基磺酰氧基)苯甲酸甲酯
向反应容器中添加5-氰基-4-羟基-2-(三氟甲基)苯甲酸甲酯(1.00g,4.08mmol)、二氯甲烷(20mL)和吡啶(0.968g,12.2mmol),将反应混合物冷却至0℃并三氟甲磺酸酐(2.88g,10.2mmol)。使反应混合物温热至室温,在室温下搅拌30分钟,冷却至0℃。添加二氯甲烷(30mL)和水(50mL)。收集有机相,经Na2SO4干燥,在减压下浓缩,并进行硅胶色谱法纯化(乙酸乙酯/石油醚=1:10)以得到无色油状物(1.38g,90.0%)。DMSO-d6中的1H-NMR[ppm]:8.70(s,1H),8.46(s,1H),3.92(s,3H)。
步骤4:5-氰基-2-(三氟甲基)-4-[4-(三氟甲基)苯基]苯甲酸甲酯
将5-氰基-2-(三氟甲基)-4-(三氟甲基磺酰氧基)苯甲酸甲酯(1.75g,4.64mmol)、[4-(三氟甲基)苯基]硼酸(1.76g,9.28mmol)、四(三苯基膦)-钯(0)(0.536g,0.464mmol)、碳酸钾(1.6g,11.6mmol)在1,4-二噁烷(30.0mL)中的混合物在110℃下在氮气氛下搅拌16小时。将反应混合物倒入水中并用乙酸乙酯萃取三次。将合并的有机层经Na2SO4干燥,过滤并在真空下浓缩。将粗产物通过硅胶柱色谱法纯化以得到白色固体(1.50g,86.6%)。DMSO-d6中的1H-NMR[ppm]:8.53(s,1H),8.17(s,1H),7.90-8.10(m,4H),3.93(s,3H)。
步骤5:5-氰基-2-(三氟甲基)-4-[4-(三氟甲基)苯基]苯甲酸酯
向5-氰基-2-(三氟甲基)-4-[4-(三氟甲基)苯基]苯甲酸甲酯(2.00g,5.36mmol)在甲醇(10mL)和水(5mL)中的溶液中逐滴添加水(5mL)中的氢氧化钠(0.643g,16.1mmol)。5分钟后添加四氢呋喃(10mL)。将混合物在室温下搅拌2小时。将反应混合物倒入盐酸水溶液中并用乙酸乙酯(50mL)萃取,经Na2SO4干燥,过滤并在真空下浓缩以得到白色固体(1.40g,72.7%)。DMSO-d6中的1H-NMR[ppm]:8.46(s,1H),8.11(s,1H),7.90-8.10(m,4H)。将此材料用于下一步骤。
步骤6:5-[4-(5-甲基-1,2,4-噁二唑-3-基)哌啶-1-羰基]-4-(三氟甲基)-2-[4-(三氟甲基)苯基]苯甲腈(化合物P1.1)
向5-氰基-2-(三氟甲基)-4-[4-(三氟甲基)苯基]苯甲酸(200mg,0.557mmol)在二氯甲烷(10.0mL)中的溶液中添加5-甲基-3-(4-哌啶基)-1,2,4-噁二唑的盐酸盐(126mg,0.618mmol,1.11eq)(如日本曹达株式会社(Nippon Soda)专利申请WO 2017195703中所述合成)。随后添加HATU(234mg,0.615mmol,1.11eq)和二异丙基-乙基-胺(216mg,1.68mmol,3.01eq)。将反应混合物在室温下搅拌21小时并且然后倒入NaHCO3水溶液中。将混合物用乙酸乙酯萃取三次。将水层用2N盐酸酸化并用乙酸乙酯萃取三次。将合并的有机层用盐水洗涤,经Na2SO4干燥,过滤并在减压下浓缩。将残余物通过色谱法(乙酸乙酯/石油醚=1:2)纯化以得到205mg(产率:72%)的呈白色固体的5-[4-(5-甲基-1,2,4-噁二唑-3-基)哌啶-1-羰基]-4-(三氟甲基)-2-[4-(三氟甲基)苯基]苯甲腈。CDCl3中的1H-NMR[ppm]:7.85(d,2H),7.82-7.74(m,2H),7.70(d,2H),4.64(s,1H),3.49(d,1H),3.31-3.02(m,3H),2.59(d,3H),2.19(d,1H),2.06-1.79(m,3H),7.74-7.88(m,4H),7.70(d,2H),4.60(t,1H),3.50(t,1H),3.02-3.40(m,3H),2.57(d,3H),2.10-2.25(m,1H),1.79-2.06(m,3H)。LC-MS(方法1):RT=4.80min;[M+H]+=509。
实例P2:5-[4-(3,5-二氯-2-吡啶基)哌嗪-1-羰基]-4-(三氟甲基)-2-[4-(三氟甲
基)苯基]苯甲腈(化合物P2.1):
向5-氰基-2-(三氟甲基)-4-[4-(三氟甲基)苯基]苯甲酸(158mg,0.44mmol)在DMF(5mL)中的溶液中添加4-(3,5-二氯-2-吡啶基)哌嗪(108mg,0.463mmol)、HATU(201mg,0.528mmol)和二异丙基乙胺(227mg,1.76mmol)。将反应混合物在室温下搅拌16小时。然后将混合物倒入水中并用乙酸乙酯萃取三次。将合并的有机层用水洗涤两次并用盐水洗涤一次,经Na2SO4干燥并除去溶剂。将粗产物通过硅胶色谱法(乙酸乙酯/石油醚=1:1)纯化以得到呈白色固体的产物(187mg,74%)。CDCl3中的1H-NMR[ppm]:8.16(s,1H),7.88(s,1H),7.76-7.85(m,3H),7.71(d,2H),7.70(s,1H),3.85-4.10(m,2H),3.25-3.53(m,6H)。LC-MS(方法1):RT=5.51min;[M+H]+=574。
实例P3:5-[4-(3,5-二氯-2-吡啶基)哌嗪-1-羰基]-4-(三氟甲基)-2-[4-(三氟甲
基)苯基]硫代苯甲酰胺(化合物P8.1):
向5-[4-(3,5-二氯-2-吡啶基)哌嗪-1-羰基]-4-(三氟甲基)-2-[4-(三氟甲基)苯基]苯甲腈(0.134g,0.234mmol)在DMF(2.3mL)中的溶液中添加二氯化镁(0.062g,0.304mmol,1.3eq)。将混合物在室温下搅拌1小时。然后添加硫氢化钠(0.05g,0.888mmol,3.8eq)并在室温下继续搅拌1小时。将反应混合物用饱和NHCl4水溶液处理并且然后用乙酸乙酯萃取三次。将有机相经Na2SO4干燥并在减压下除去溶剂。将残余物通过色谱法纯化以得到呈白色泡沫的所希望的产物(130mg,91%)。CDCl3中的1H-NMR[ppm]:8.18(s,1H),7.62-7.80(m,7H),7.01(bs,1H),6.97(bs,1H),3.85-4.10(m,2H),3.25-3.60(m,6H)。LC-MS(方法2):RT=1.25min;[M+H]+=607。
实例P4:5-[4-(3,5-二氯-2-吡啶基)哌嗪-1-羰基]-4-乙氧基-2-[4-(三氟甲基)-
苯基]-苯甲腈(化合物P2.5):
步骤1:4-氨基-5-氰基-2-羟基-苯甲酸乙酯
在4℃下向乙醇钠(1.1eq.)在乙醇(20%w/w)中的溶液中缓慢添加丙二腈(1.32g,20mmol,1eq)并将混合物搅拌15分钟。然后在冰冷却下添加(2E)-2-(乙氧基亚甲基)-3-氧代-丁酸乙酯(3.72g,20mmol)在乙醇(50mL)中的溶液。将反应混合物加热至回流持续1小时。在冷却后,将反应混合物用乙酸乙酯和水稀释。分离各相并将水相用乙酸乙酯萃取三次。将合并的有机层用水洗涤两次并用盐水洗涤一次,经Na2SO4干燥并除去溶剂。获得了2.45g(59%产率)的呈白色固体的4-氨基-5-氰基-2-羟基-苯甲酸乙酯。DMSO中的1H NMR[ppm]:10.98(s,1H),7.89(s,1H),6.79(s,2H),6.20(s,1H),4.28(q,2H),1.30(t,3H)。LC-MS(方法1):RT=3.98min;[M+H]+=207。
步骤2:5-氰基-2-羟基-4-碘-苯甲酸乙酯
在0℃下向三氟化硼二乙醚(568mg,4mmol)在THF(5mL)中的溶液中添加4-氨基-5-氰基-2-羟基-苯甲酸乙酯(412mg,4mmol)在THF(5mL)中的溶液。然后将混合物冷却至-10℃,添加亚硝酸叔丁酯(268mg,2.6mmol)并将反应混合物在-10℃搅拌0.5小时。然后添加在丙酮(10mL)中的碘化钠(390mg,2.6mmol)并将混合物在室温下搅拌1.5小时。将反应混合物用乙酸乙酯和水稀释。分离各相,并将水相用乙酸乙酯萃取三次。将合并的有机层用水洗涤两次并用盐水洗涤一次,经Na2SO4干燥并除去溶剂。将粗产物通过硅胶色谱法(乙酸乙酯/石油醚=1:2)纯化以提供呈白色固体的产物(599mg,94.5%)。DMSO-d6中的1H NMR[ppm]:11.36(s,1H),8.07(s,1H),7.63(s,1H),4.32(q,2H),1.32(t,3H)。LC-MS(方法1):RT=4.76min;[M+H]+=318。
步骤3:5-氰基-2-乙氧基-4-碘-苯甲酸乙酯
向5-氰基-2-羟基-4-碘-苯甲酸乙酯(1.17g,3.7mmol)在丙酮(50mL)中的溶液中添加碘乙烷(867mg,5.56mmol)和碳酸钾(767mg,5.56mmol)。将混合物搅拌并加热至回流,持续5小时。在冷却后,将反应混合物用乙酸乙酯和水稀释。分离各相并将水相用乙酸乙酯萃取三次。将合并的有机层用水洗涤两次并用盐水洗涤一次,经Na2SO4干燥并除去溶剂。将粗产物通过硅胶色谱法(乙酸乙酯/石油醚=1:5)纯化以提供呈白色固体的产物(372mg,29%)。CDCl3中的1H NMR[ppm]:7.99(s,1H),7.45(s,1H),4.35(q,2H),4.16(q,2H),1.49(t,3H),1.38(t,3H)。LC-MS(方法1):RT=4.683min;[M+H]+=346。
步骤4:5-氰基-2-乙氧基-6-[4-(三氟甲基)苯基]吡啶-3-甲酸乙酯
将5-氰基-2-乙氧基-6-碘-吡啶-3-甲酸乙酯(370mg,1.07mmol)、1-[4-(三氟甲基)苯基]硼酸(408mg,2.14mmol)、Pd(PPh3)4(247mg,0.21mmol)和碳酸钾(443mg,3.21mmol)在1,4-二噁烷(20.0mL)中的混合物在氮气下在90℃下搅拌16小时。然后将混合物倒入水中并用乙酸乙酯萃取三次。将合并的有机层用水洗涤两次并用盐水洗涤一次,经Na2SO4干燥并除去溶剂。将粗产物通过硅胶色谱法(乙酸乙酯/石油醚=1:5)纯化以得到呈白色固体的产物(380mg,97.5%)。CDCl3中的1H NMR[ppm]:8.22(s,1H),7.77(d,2H),7.68(d,2H),7.01(s,1H),4.40(q,2H),4.22(q,2H),1.52(t,3H),1.41(t,3H)。LC-MS(方法1):RT=3.615min;[M+H]+=364。
步骤5:5-氰基-2-乙氧基-4-[4-(三氟甲基)苯基]苯甲酸
将5-氰基-2-乙氧基-4-[4-(三氟甲基)苯基]苯甲酸乙酯(1.3g,3.58mmol)溶解在四氢呋喃(10mL)中并且添加溶解在水(2mL)中的氢氧化钾(429mg,10.7mmol,3.0eq.)。将反应混合物在室温下搅拌16小时。然后将反应混合物用乙酸乙酯和2N盐酸稀释。将混合物用乙酸乙酯萃取三次。将合并的有机层用水洗涤两次并用盐水洗涤一次,经Na2SO4干燥并除去溶剂以得到呈白色固体的粗产物(1.2g,100%),将其直接用于下一步骤。
步骤6:5-[4-(3,5-二氯-2-吡啶基)哌嗪-1-羰基]-4-乙氧基-2-[4-(三氟甲基)-苯基]-苯甲腈(化合物P2.5):
向5-氰基-2-乙氧基-4-[4-(三氟甲基)苯基]苯甲酸(121mg,0.36mmol)在DMF(5mL)中的溶液中添加1-(3,5-二氯-2-吡啶基)哌嗪(99mg,0.43mmol)、HATU(163mg,0.43mmol)和二异丙基乙胺(139mg,1.08mmol)。将反应混合物在室温下搅拌16小时。然后将混合物倒入水中并用乙酸乙酯萃取三次。将合并的有机层用水洗涤两次并用盐水洗涤一次,经Na2SO4干燥并除去溶剂。将粗产物通过硅胶色谱法(乙酸乙酯/石油醚=1/1)纯化以得到呈白色固体的产物(140mg,71%)。CDCl3中的1H NMR[ppm]:8.16(d,1H),7.74(d,2H),7.71(s,1H),7.64-7.68(m,3H),6.97(s,1H),4.15-4.25(m,2H),3.80-4.20(m,2H),1.48(t,3H)。LC-MS(方法1):RT=5.627min;[M+H]+=550。
实例P5:4-乙氧基-5-[4-(乙基硫烷基甲基)哌啶-1-羰基]-2-[4-(三氟甲基)苯
基]-苯甲腈(化合物P1.46):
向5-氰基-2-乙氧基-4-[4-(三氟甲基)苯基]苯甲酸(140mg,0.42mmol)在DMF(5mL)中的溶液中添加4-(乙基硫烷基甲基)哌啶盐酸盐(117mg,0.598mmol)、HATU(190mg,0.5mmol)和二异丙基乙胺(163mg,1.62mmol)。将反应混合物在室温下搅拌16小时。然后将混合物倒入水中并用乙酸乙酯萃取三次。将合并的有机层用水洗涤两次并用盐水洗涤一次,经Na2SO4干燥并除去溶剂。将粗产物通过硅胶色谱法(乙酸乙酯/石油醚=1:1)纯化以得到呈白色固体的产物(127mg,64%)。CDCl3中的1H NMR[ppm]:7.76(d,2H),7.60-7.70(m,3H),6.94(d,1H),4.78(t,1H),4.09-4.25(m,2H),3.49(d,1H),2.90-3.10(m,1H),2.79(q,1H),2.42-2.59(m,4H),1.90-2.05(m,1H),1.69-1.85(m,2H),1.40-1.51(m,3H),1.20-1.30(m,5H)。LC-MS(方法1):RT=5.32min;[M+H]+=477。
实例P6:4-乙氧基-5-[4-(乙基硫烷基甲基)哌啶-1-羰基]-2-[4-(三氟甲基)苯
基]-苯甲腈(化合物P3.7):
步骤1:3-(乙酰基硫烷基甲基)氮杂环丁烷-1-甲酸叔丁酯
在室温下向在丙酮(10.0mL)中的3-(溴甲基)-氮杂环丁烷-1-甲酸叔丁酯(0.500g,2.00mmol)中添加乙酰基硫烷基钠(85.0%,0.462g,4.00mmol)并将混合物在室温下搅拌16小时。然后将混合物倒入稀盐酸中并用乙酸乙酯萃取三次。将合并的有机层经Na2SO4干燥,过滤并在真空下浓缩。将粗产物通过硅胶柱色谱法(石油醚/乙酸乙酯=20:1)纯化以提供315mg(产率:64%)的3-(乙酰基硫烷基甲基)-氮杂环丁烷-1-甲酸叔丁酯。CDCl3中的1H NMR[ppm]:3.98(t,2H),3.56(dd,2H),3.09(d,2H),2.62-2.78(m,1H),2.34(s,3H),1.42(d,9H)。LC-MS(方法1):RT=4.25min;[M+Na]+=268。
步骤2:3-(硫烷基甲基)氮杂环丁烷-1-甲酸叔丁酯
向在甲醇(10.0mL)中的3-(乙酰基硫烷基甲基)氮杂环丁烷-1-甲酸叔丁酯(1.00g,4.08mmol)中添加硼氢化钠(0.308g,8.15mmol)并在室温下搅拌16小时。然后将混合物倒入稀盐酸中并用乙酸乙酯萃取三次。将合并的有机层经Na2SO4干燥,过滤并在真空下浓缩。将粗产物通过硅胶柱色谱法(石油醚/乙酸乙酯=20:1)纯化以提供528mg(产率:64%)的3-(硫烷基甲基)氮杂环丁烷-1-甲酸叔丁酯。CDCl3中的1H NMR[ppm]:4.02(t,2H),3.60(dd,2H),2.73(t,2H),2.61-2.65(m,1H),1.43(s,9H),1.30(t,1H)。LC-MS(方法1):RT=4.11min;[M+Na]+=226。
步骤3:3-(丙基硫烷基甲基)氮杂环丁烷-1-甲酸叔丁酯
向在丙酮(10.0mL)中的3-(硫烷基甲基)氮杂环丁烷-1-甲酸叔丁酯(500mg,2.46mmol)和K2CO3(1.02g,7.38mmol)中添加1-碘丙烷(0.627g,3.69mmol)并将反应混合物在室温下搅拌16小时。然后将混合物倒入稀盐酸中并用乙酸乙酯萃取三次。将合并的有机层经Na2SO4干燥,过滤并在真空下浓缩。将粗产物通过硅胶柱色谱法(石油醚/乙酸乙酯=20:1)纯化以提供331mg(产率:52%)的3-(丙基硫烷基甲基)氮杂环丁烷-1-甲酸叔丁酯。CDCl3中的1H NMR[ppm]:4.02(t,2H),3.60(dd,2H),2.60-2.75(m,3H),2.47(t,2H),1.54-1.63(m,2H),1.43(s,9H),0.98(t,3H)。
步骤4:3-(丙基硫烷基甲基)氮杂环丁烷的三氟乙酸盐
将在二氯甲烷(15.0mL)中的3-(丙基硫烷基甲基)氮杂环丁烷-1-甲酸叔丁酯(500mg,2.04mmol)和2,2,2-三氟乙酸(0.929g,8.15mmol)在室温下搅拌16小时。将反应混合物在真空下浓缩并用于下一步骤。DMSO-d6中的1H NMR[ppm]:4.17(s,2H),3.90(s,2H),3.13(t,1H),2.78(d,2H),2.48(t,2H),1.64-1.52(m,2H),0.98(t,3H)。
步骤5:5-[3-(丙基硫烷基甲基)氮杂环丁烷-1-羰基]-4-(三氟甲基)-2-[4-(三氟甲基)-苯基]苯甲腈
向5-氰基-2-(三氟甲基)-4-[4-(三氟甲基)苯基]苯甲酸(150mg,0.418mmol)在DMF(5mL)中的溶液中添加3-(丙基硫烷基甲基)氮杂环丁烷的三氟乙酸盐(162mg,0.626mmol,1.5eq)。随后添加HATU(238mg,0.626mmol,1.5eq.)和二异丙基乙胺(162mg,1.25mmol,3.00eq.)。将反应混合物在室温下搅拌16小时并且然后倒入NaHCO3水溶液中。将混合物用乙酸乙酯萃取三次。将水层用2N盐酸酸化并用乙酸乙酯萃取三次。将合并的有机层用盐水洗涤,经Na2SO4干燥,过滤并在减压下浓缩。将残余物通过色谱法(石油醚/乙酸乙酯=1:1)纯化以提供121mg(产率:60%)的呈无色胶状物获得的5-[3-(丙基硫烷基甲基)氮杂环丁烷-1-羰基]-4-(三氟甲基)-2-[4-(三氟甲基)苯基]-苯甲腈。CDCl3中的1H-NMR[ppm]:7.85(s,1H),7.77-7.83(m,3H),7.69(d,2H),4.33(t,1H),4.05(t,1H),3.92(dd,1H),3.66(dd,1H),2.65-2.99(m,3H),2.40-2.60(m,2H),1.55-1-70(m,2H),0.98(t,3H)。LC-MS(方法1):RT=5.38min;[M+H]+=487。
步骤6:5-[3-(丙基亚磺酰基甲基)氮杂环丁烷-1-羰基]-4-(三氟甲基)-2-[4-(三氟甲基)苯基]-苯甲腈(化合物P3.7)
向在二氯甲烷(20mL)中的5-[3-(丙基硫烷基甲基)-氮杂环丁烷-1-羰基]-4-(三氟甲基)-2-[4-(三氟甲基)苯基]苯甲腈(120mg,0.247mmol)中添加3-氯-过苯甲酸(0.034g,0.197mmol,0.8eq)并在室温下搅拌2小时。然后将混合物倒入水中的NaHCO3和Na2SO3的饱和溶液中并用乙酸乙酯萃取三次。将合并的有机层经Na2SO4干燥,过滤并在真空下浓缩。将粗产物通过硅胶柱色谱法(乙酸乙酯/石油醚=1:2)纯化以得到41mg(产率:33%)的呈无色胶状物的5-[3-(丙基亚磺酰基甲基)氮杂环丁烷-1-羰基]-4-(三氟甲基)-2-[4-(三氟甲基)苯基]苯甲腈。DMSO-d6中的1H-NMR[ppm]:8.32(s,1H),8.09(s,1H),7.88-7.96(m,4H),4.24(t,1H),4.05-4.15(m,1H),3.68-3.97(m,1H),3.82(dd,1H),2.96-3.20(m,3H),2.60-2.75(m,2H),1.53-1.71(m,2H),0.98(t,3H)。LC-MS(方法1):RT=4.36min;[M+H]+=503。
实例P7:4-甲基-5-[4-(5-甲基-1,2,4-噁二唑-3-基)哌嗪-1-羰基]-2-[4-(三氟
甲基)苯基]苯-1,3-二甲腈(化合物P6.1):
步骤1:4-氨基-3,5-二氰基-2-甲基-苯甲酸乙酯
将乙酰乙酸乙酯(1.3mL,0.01mmol)在甲醇中的溶液冷却至0℃,然后用甲醛水溶液(1mL)处理。将反应混合物搅拌3小时并且然后在搅拌下在1小时的时间内逐渐添加丙二腈(1.2g,0.2mmol)在甲醇(30mL)中的溶液,之后向混合物中添加在甲醇(20mL)中的吗啉溶液(0.8mL,0.1mmol)。将此混合物用冰冷却3小时,然后使其在室温下静置48小时。过滤出固体并用少量的甲醇洗涤以得到目标化合物(1.8g,78%)。CDCl3中的1H-NMR[ppm]:8.02(s,1H),7.17(s,2H),4.26(q,2H),2.65(s,3H),1.35(t,3H)。MS(ESI)[M+H]+=230.0。
步骤2:3,5-二氰基-4-碘-2-甲基-苯甲酸乙酯
将4-氨基-3,5-二氰基-2-甲基-苯甲酸乙酯(1.90g,8.3mmol)悬浮在H2SO4(40mL,50%)中,冷却至-5℃并搅拌1小时。缓慢添加亚硝酸钠(0.86g,12.5mmol)在水(5mL)中的溶液,并将混合物在0℃下搅拌30分钟。然后将黄色浆液缓慢添加到冰冷却的碘化钾(13.8g,83mmol)在水(230mL)中的溶液中。然后移除冰浴,并将起泡沫的悬浮液在室温下搅拌2小时。添加二氯甲烷(100mL),然后添加饱和Na2S2O3溶液。分离有机层,并将水层用二氯甲烷萃取。将合并的二氯甲烷层经Na2SO4干燥,蒸发溶剂以产生3,5-二氰基-4-碘-2-甲基-苯甲酸乙酯。(0.8g,28%)。CDCl3中的1H-NMR[ppm]:8.27(s,1H),4.20(q,2H),2.50(s,3H),1.42(t,3H)。MS(ESI)[M+H]+=341.1。
步骤3:3,5-二氰基-2-甲基-4-[4-(三氟甲基)苯基]苯甲酸乙酯
将3,5-二氰基-4-碘-2-甲基-苯甲酸乙酯(0.74g,2.18mmol)、[4-(三氟甲基)苯基]硼酸(0.62g,3.26mmol)、碳酸钠(0.46g,4.33mmol)和四(三苯基膦)钯(0)(0.25g,0.218mmol)在甲苯(20mL)/水(6mL)中的混合物在80℃下搅拌过夜。将反应混合物冷却至室温并用乙酸乙酯萃取。分离有机层,用盐水(20mL)洗涤,经硫酸镁干燥并在真空中浓缩。通过柱色谱法(乙酸乙酯/石油醚=2:1)纯化得到目标化合物(0.7g,90%)。CDCl3中的1H-NMR[ppm]:8.45(s,1H),7.84(d,2H),7.64(d,2H),4.46(q,2H),2.97(s,3H),1.45(t,3H)。MS(ESI)[M+H]+=359.3。
步骤4:3,5-二氰基-2-甲基-4-[4-(三氟甲基)苯基]苯甲酸
添加3,5-二氰基-2-甲基-4-[4-(三氟甲基)苯基]苯甲酸乙酯(0.56g,1.56mmol)在甲醇(10mL)中的溶液、氢氧化钠(75mg,1.88mmol)。将混合物在室温下搅拌2小时。然后通过添加盐酸将pH调整到2-3并将混合物用乙酸乙酯萃取。分离有机层,用盐水洗涤,经硫酸镁干燥并在真空中浓缩以得到产物(0.5g,97%)。DMSO-d6中的1H-NMR[ppm]:8.57(s,1H),8.02(d,2H),7.87(d,2H),2.83(s,3H)。MS(ESI)[M+H]+=331.3。
步骤5:4-甲基-5-[4-(5-甲基-1,2,4-噁二唑-3-基)哌嗪-1-羰基]-2-[4-(三氟甲基)-苯基]苯-1,3-二甲腈(化合物P6.1)
将3,5-二氰基-2-甲基-4-[4-(三氟甲基)苯基]苯甲酸(250mg,0.757mmol)、5-甲基-3-(4-哌啶基)-1,2,4-噁二唑(127mg,0.757mmol)(如日本曹达株式会社专利申请WO2017195703中所述合成)、二异丙基乙胺(294mg,2.27mmol)和HATU(431mg,1.14mol)在二氯甲烷(10mL)中的混合物在室温下搅拌4小时。将混合物倒入水(50mL)中并将混合物用乙酸乙酯(每次50mL)萃取三次,将合并的有机相经Na2SO4干燥并浓缩。将材料通过色谱法(乙酸乙酯/石油醚=1:2)纯化以得到呈固体的标题化合物(230mg,63%)。CDCl3中的1H-NMR[ppm]:7.84(d,2H),7.76,7.79(2s,1H),7.63(d,2H),4.63(t,1H),3.53(d,1H),3.10-3.30(m,3H),2.64,2.59(2s,3H),2.58(s,3H),1.75-2.25(m,4H)。MS(ESI)[M+H]+=480.2。
如在以上实例中所描述的或类似的方法制备表P1、P2、P3、P4、P5、P6、P7和P8中的化合物。
表P1:具有式(I-c)的化合物
可以如在以上实例中所描述的或类似的方法制备表P1中的化合物。下面的表中使用了以下缩写:RT=保留时间,min=分钟,m.p.=熔点或熔距。
表P1:
表P2:具有式(I-d)的化合物
可以如在以上实例中所描述的或类似的方法制备表P2中的化合物。下面的表中使用了以下缩写:RT=保留时间,min=分钟,m.p.=熔点。
表P2:
表P3:具有式(I-e)的化合物
可以如在以上实例中所描述的或类似的方法制备表P3中的化合物。下面的表中使用了以下缩写:RT=保留时间,min=分钟;m.p.熔点。
表P3:
表P4:具有式(I-e)的化合物
可以如在以上实例中所描述的或类似的方法制备表P2中的化合物。下面的表中使用了以下缩写:RT=保留时间,min=分钟,m.p.=熔点。
表P4:
表P5:具有式(I-g)的化合物
可以如在以上实例中所描述的或类似的方法制备表P5中的化合物。下面的表中使用了以下缩写:RT=保留时间,min=分钟;m.p.=熔点。
表P5
表P6:具有式(I-h)的化合物
可以如在以上实例中所描述的或类似的方法制备表P6中的化合物。下面的表中使用了以下缩写:RT=保留时间,min=分钟;m.p.=熔点。
表P6
表P7:具有式(I-i)的化合物
可以如在以上实例中所描述的或类似的方法制备表P7中的化合物。下面的表中使用了以下缩写:RT=保留时间,min=分钟;m.p.=熔点。
表P7
表P8:具有式(I-j)的化合物
可以如在以上实例中所描述的或类似的方法制备表P8中的化合物。下面的表中使用了以下缩写:RT=保留时间,min=分钟;m.p.=熔点。
表P8
表U1中的中间体是新的并且可用于合成一些具有通用结构I的化合物。它们可以如在以上实例中所描述的或类似的方法制备。下面的表中使用了以下缩写:s=单峰,d=二重峰,t=三重峰,q=四重峰,m=多重峰。
表U1:
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,适合添加的活性成分是例如以下类别的活性成分的代表:有机磷化合物、硝基苯酚衍生物、硫脲、保幼激素、甲脒、二苯甲酮衍生物、脲类、吡咯衍生物、氨基甲酸酯、拟除虫菊酯、氯化烃、酰基脲、吡啶基亚甲基氨基衍生物、大环内酯类、新烟碱以及苏芸金芽孢杆菌制剂。
优选具有式(I)的化合物与活性物质的以下混合物(缩写“TX”意指“选自表1至35和表P1至P8中定义的化合物中的一种化合物”):
辅助剂,其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,其选自阿维菌素+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: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:2246757-58-2(或2249718-27-0)+TX、CAS号:907187-07-9+TX、氯虫苯甲酰胺+TX、氯丹+TX、溴虫腈+TX、氯炔丙菊酯+TX、环虫酰肼+TX、克仑吡林+TX、除线威(Cloethocarb)+TX、噻虫胺+TX、2-氯苯基N-甲基氨基甲酸酯(CPMC)+TX、苯腈磷+TX、溴氰虫酰胺+TX、环溴虫酰胺+TX、Cyclobutrifluram+TX、拟除虫菊酯+TX、环氧虫啶+TX、腈吡螨酯+TX、乙唑螨腈(Cyetpyrafen)+TX、乙唑螨腈+TX、丁氟螨酯+TX、氟氯氰菊酯+TX、氯氟氰虫酰胺(Cyhalodiamide)+TX、三氟氯氰菊酯+TX、氯氰菊酯+TX、苯氰菊酯+TX、Cyproflanilide+TX、灭蝇胺+TX、溴氰菊酯+TX、杀螨隆+TX、氯亚胺硫磷+TX、二溴磷(Dibrom)+TX、Dicloromezotiaz+TX、氟螨嗪+TX、除虫脲+TX、dimpropyridaz+TX、二活菌素+TX、敌螨普+TX、呋虫胺+TX、蔬果磷+TX、埃玛菌素(或埃玛菌素苯甲酸盐)+TX、右旋烯炔菊酯+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、醚菊酯+TX、乙螨唑+TX、伐灭磷+TX、喹螨醚+TX、五氟苯菊酯+TX、杀螟硫磷+TX、仲丁威+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、叶塞灵+TX、氰戊菊酯+TX、氟虫腈+TX、氟麦托醌(Flometoquin)+TX、氟啶虫酰胺+TX、嘧螨酯+TX、Fluazaindolizine+TX、啶蜱脲+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、氟己芬(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+TX、Heptafluthrin+TX、噻螨酮+TX、氟蚁腙+TX、咪唑环磷(Imicyafos)+TX、吡虫啉+TX、炔咪菊酯+TX、茚虫威+TX、碘甲烷+TX、异菌脲+TX、Isocycloseram+TX、异拌磷+TX、伊维菌素+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、自克威+TX、灭螨菌素+TX、Momfluorothrin+TX、灭绦灵+TX、Nicofluprole+TX;烯啶虫胺+TX、硝虫噻嗪+TX、氧乐果+TX、杀线威+TX、Oxazosulfyl+TX、对硫磷-乙基+TX、苄氯菊酯+TX、苯醚菊酯+TX、磷虫威+TX、胡椒基丁醚+TX、抗蚜威+TX、嘧啶磷-乙基+TX、嘧啶磷-甲基+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、胺丙畏+TX、残杀威+TX、丙硫磷+TX、丙苯烃菊酯(Protrifenbute)+TX、吡氟丁酰胺(Pyflubumide)+TX、吡蚜酮+TX、吡唑硫磷+TX、啶吡唑虫胺(Pyrafluprole)+TX、哒螨灵+TX、啶虫丙醚+TX、氟虫吡喹(Pyrifluquinazon)+TX、嘧螨醚+TX、嘧螨胺+TX、吡唑虫啶+TX、蚊蝇醚+TX、苄呋菊脂+TX、Sarolaner+TX、司拉克丁(Selamectin)+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、Spiropidion+TX、螺虫乙酯+TX、砜虫啶+TX、虫酰肼+TX、吡螨胺+TX、丁基嘧啶磷(Tebupirimiphos)+TX、七氟菊酯+TX、双硫磷+TX、四氯虫酰胺+TX、四氯杀螨砜(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、久效威+TX、甲基乙拌磷+TX、杀虫单+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(Triflumezopyrim)+TX、Tyclopyrazoflor+TX、ζ-氯氰菊酯+TX、海藻提取物和衍生自糖酰的发酵产物+TX、海藻提取物和衍生自糖酰的发酵产物(包含脲+TX、氨基酸+TX、钾和钼以及EDTA螯合锰)+TX、海藻提取物和发酵的植物产物+TX、海藻提取物和发酵的植物产物(包含植物激素+TX,维生素+TX,EDTA螯合铜+TX、锌+TX、以及铁+TX)、印楝素+TX、芽孢杆菌属鲇泽(Bacillus aizawai)+TX、蚀几丁质芽孢杆菌(Bacillus chitinosporus)AQ746(NRRL登记号B-21 618)+TX、坚强芽孢杆菌+TX、芽孢杆菌属库尔斯塔克(Bacillus kurstaki)+TX、蕈状芽孢杆菌AQ726(NRRL登记号B-21664)+TX、短小芽孢杆菌(NRRL登记号B-30087)+TX、短小芽孢杆菌AQ717(NRRL登记号B-21662)+TX、芽孢杆菌属物种AQ178(ATCC登记号53522)+TX、芽孢杆菌属物种AQ175(ATCC登记号55608)+TX、芽孢杆菌属物种AQ177(ATCC登记号55609)+TX、未指明的枯草芽孢杆菌+TX、枯草芽孢杆菌AQ153(ATCC登记号55614)+TX、枯草芽孢杆菌AQ30002(NRRL登记号B-50421)+TX、枯草芽孢杆菌AQ30004(NRRL登记号B-50455)+TX、枯草芽孢杆菌AQ713(NRRL登记号B-21661)+TX、枯草芽孢杆菌AQ743(NRRL登记号B-21665)+TX、苏云金芽孢杆菌AQ52(NRRL登记号B-21619)+TX、苏云金芽孢杆菌BD#32(NRRL登记号B-21530)+TX、苏云金芽孢杆菌库尔斯塔克亚种(subspec.kurstaki)BMP 123+TX、球孢白僵菌+TX、D-柠檬烯+TX、颗粒体病毒+TX、康壮素(Harpin)+TX、棉铃虫核型多角体病毒+TX、谷实夜蛾核型多角体病毒+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、绿僵菌属物种+TX、Muscodor albus 620(NRRL登记号30547)+TX、Muscodor roseus A3-5(NRRL登记号30548)+TX、基于印楝树的产品+TX、玫烟色拟青霉+TX、淡紫色拟青霉+TX、拟斯扎瓦巴氏杆菌+TX、穿刺巴氏杆菌+TX、分枝巴氏杆菌+TX、索雷巴氏杆菌(Pasteuriathornei)+TX、巴氏杆菌+TX、对-伞花烃+TX、小菜蛾颗粒体病毒+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、QRD 452(类萜共混物)+TX、QRD460(类萜共混物)+TX、皂树+TX、球状红球菌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(NRRL登记号30232)+TX、链霉菌属物种(NRRL登记号B-30145)+TX、类萜共混物+TX以及轮枝孢属物种;
杀藻剂,其选自由以下组成的物质组:百杀辛(bethoxazin)[CCN]+TX、二辛酸铜(IUPAC名称)(170)+TX、硫酸铜(172)+TX、cybutryne[CCN]+TX、二氯萘醌(dichlone)(1052)+TX、双氯酚(232)+TX、茵多酸(295)+TX、三苯锡(fentin)(347)+TX、熟石灰[CCN]+TX、代森钠(nabam)(566)+TX、灭藻醌(quinoclamine)(714)+TX、醌萍胺(quinonamid)(1379)+TX、西玛津(730)+TX、三苯基乙酸锡(IUPAC名称)(347)和三苯基氢氧化锡(IUPAC名称)(347)+TX;
驱蠕虫剂,其选自由以下组成的物质组:阿维菌素(1)+TX、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(别名)[CCN]+TX、多杀菌素(737)和托布津(1435)+TX;
杀鸟剂,其选自由以下组成的物质组:氯醛糖(127)+TX、异狄氏剂(1122)+TX、倍硫磷(346)+TX、吡啶-4-胺(IUPAC名称)(23)和士的宁(745)+TX;
杀细菌剂,其选自由以下组成的物质组:1-羟基-1H-吡啶-2-硫酮(IUPAC名称)(1222)+TX、4-(喹喔啉-2-基氨基)苯磺酰胺(IUPAC名称)(748)+TX、8-羟基喹啉硫酸盐(446)+TX、溴硝醇(97)+TX、二辛酸铜(IUPAC名称)(170)+TX、氢氧化铜(IUPAC名称)(169)+TX、甲酚[CCN]+TX、双氯酚(232)+TX、双吡硫翁(1105)+TX、多地辛(1112)+TX、敌磺钠(fenaminosulf)(1144)+TX、甲醛(404)+TX、汞加芬(别名)[CCN]+TX、春雷霉素(483)+TX、春雷霉素盐酸盐水合物(483)+TX、双(二甲基二硫代氨基甲酸)镍(IUPAC名称)(1308)+TX、三氯甲基吡啶(nitrapyrin)(580)+TX、辛噻酮(octhilinone)(590)+TX、奥索利酸(606)+TX、土霉素(611)+TX、羟基喹啉硫酸钾(446)+TX、噻菌灵(probenazole)(658)+TX、链霉素(744)+TX、链霉素倍半硫酸盐(744)+TX、叶枯酞(766)+TX、和硫柳汞(别名)[CCN]+TX;
生物试剂,其选自由以下组成的物质组:棉褐带卷蛾GV(别名)(12)+TX、放射形土壤杆菌(别名)(13)+TX、钝绥螨属物种(Amblyseius spp.)(别名)(19)+TX、芹菜夜蛾NPV(别名)(28)+TX、原樱翅缨小蜂(Anagrus atomus)(别名)(29)+TX、短距蚜小蜂(Aphelinusabdominalis)(别名)(33)+TX、棉蚜寄生蜂(Aphidius colemani)(别名)(34)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)(别名)(35)+TX、苜蓿银纹夜蛾NPV(别名)(38)+TX、坚强芽孢杆菌(Bacillus firmus)(别名)(48)+TX、球形芽孢杆菌(Bacillus sphaericus Neide)(学名)(49)+TX、苏云金芽孢杆菌(Bacillus thuringiensis Berliner)(学名)(51)+TX、苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensis subsp.aizawai)(学名)(51)+TX、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensis subsp.israelensis)(学名)(51)+TX、苏云金芽孢杆菌日本亚种(Bacillus thuringiensis subsp.japonensis)(学名)(51)+TX、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subsp.kurstaki)(学名)(51)+TX、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subsp.tenebrionis)(学名)(51)+TX、球孢白僵菌(Beauveria bassiana)(别名)(53)+TX、布氏白僵菌(Beauveriabrongniartii)(别名)(54)+TX、普通草蛉(Chrysoperla carnea)(别名)(151)+TX、孟氏隐唇瓢虫(Cryptolaemus montrouzieri)(别名)(178)+TX、苹果蠹蛾GV(别名)(191)+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)(别名)(212)+TX、豌豆潜叶蝇姬小蜂(Diglyphusisaea)(别名)(254)+TX、丽蚜小蜂(Encarsia formosa)(学名)(293)+TX、桨角蚜小蜂(Eretmocerus eremicus)(别名)(300)+TX、谷实夜蛾NPV(别名)(431)+TX、嗜菌异小杆线虫(Heterorhabditis bacteriophora)和大异小杆线虫(H.megidis)(别名)(433)+TX、斑长足瓢虫(Hippodamia convergens)(别名)(442)+TX、橘粉介壳虫寄生蜂(Leptomastixdactylopii)(别名)(488)+TX、盲蝽(Macrolophus caliginosus)(别名)(491)+TX、甘蓝夜蛾NPV(别名)(494)+TX、黄阔柄跳小蜂(Metaphycus helvolus)(别名)(522)+TX、黄绿绿僵菌(Metarhizium anisopliae var.acridum)(学名)(523)+TX、金龟子绿僵菌小孢变种(Metarhizium anisopliae var.anisopliae)(学名)(523)+TX、欧洲新松叶蜂(Neodiprionsertifer)NPV和红头新松叶蜂(N.lecontei)NPV(别名)(575)+TX、小花蝽属物种(别名)(596)+TX、玫烟色拟青霉(Paecilomyces fumosoroseus)(别名)(613)+TX、智利小植绥螨(Phytoseiulus persimilis)(别名)(644)+TX、甜菜夜蛾核多角体病毒(Spodopteraexiguamulticapsid nuclear polyhedrosis virus)(学名)(741)+TX、毛蚊线虫(Steinernemabibionis)(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(Steinernema scapterisci)(别名)(742)+TX、斯氏线虫属物种(Steinernema spp.)(别名)(742)+TX、赤眼蜂属物种(别名)(826)+TX、西方盲走螨(Typhlodromus occidentalis)(别名)(844)和蜡蚧轮枝菌(Verticillium lecanii)(别名)(848)+TX;
土壤消毒剂,其选自由以下组成的物质组:碘甲烷(IUPAC名称)(542)和溴甲烷(537)+TX;
化学不育剂,其选自由以下组成的物质组:唑磷嗪(apholate)[CCN]+TX、双(氮丙啶)甲氨基膦硫化物(bisazir)(别名)[CCN]+TX、白消安(别名)[CCN]+TX、除虫脲(250)+TX、迪麦替夫(dimatif)(别名)[CCN]+TX、六甲蜜胺(hemel)[CCN]+TX、六甲磷(hempa)[CCN]+TX、甲基涕巴(metepa)[CCN]+TX、甲硫涕巴(methiotepa)[CCN]+TX、甲基唑磷嗪(methylapholate)[CCN]+TX、不孕啶(morzid)[CCN]+TX、氟幼脲(penfluron)(别名)[CCN]+TX、涕巴(tepa)[CCN]+TX、硫代六甲磷(thiohempa)(别名)[CCN]+TX、硫涕巴(别名)[CCN]+TX、曲他胺(别名)[CCN]和尿烷亚胺(别名)[CCN]+TX;
昆虫信息素,其选自由以下组成的物质组:(E)-癸-5-烯-1-基乙酸酯与(E)-癸-5-烯-1-醇(IUPAC名称)(222)+TX、(E)-十三碳-4-烯-1-基乙酸酯(IUPAC名称)(829)+TX、(E)-6-甲基庚-2-烯-4-醇(IUPAC名称)(541)+TX、(E,Z)-十四碳-4,10-二烯-1-基乙酸酯(IUPAC名称)(779)+TX、(Z)-十二碳-7-烯-1-基乙酸酯(IUPAC名称)(285)+TX、(Z)-十六碳-11-烯醛(IUPAC名称)(436)+TX、(Z)-十六碳-11-烯-1-基乙酸酯(IUPAC名称)(437)+TX、(Z)-十六碳-13-烯-11-炔-1-基乙酸酯(IUPAC名称)(438)+TX、(Z)-二十-13-烯-10-酮(IUPAC名称)(448)+TX、(Z)-十四碳-7-烯-1-醛(IUPAC名称)(782)+TX、(Z)-十四碳-9-烯-1-醇(IUPAC名称)(783)+TX、(Z)-十四碳-9-烯-1-基乙酸酯(IUPAC名称)(784)+TX、(7E,9Z)-十二碳-7,9-二烯-1-基乙酸酯(IUPAC名称)(283)+TX、(9Z,11E)-十四碳-9,11-二烯-1-基乙酸酯(IUPAC名称)(780)+TX、(9Z,12E)-十四碳-9,12-二烯-1-基乙酸酯(IUPAC名称)(781)+TX、14-甲基十八碳-1-烯(IUPAC名称)(545)+TX、4-甲基壬-5-醇与4-甲基壬-5-酮(IUPAC名称)(544)+TX、α-多纹素(alpha-multistriatin)(别名)[CCN]+TX、西部松小蠹集合信息素(brevicomin)(别名)[CCN]+TX、十二碳二烯醇(codlelure)(别名)[CCN]+TX、可得蒙(codlemone)(别名)(167)+TX、诱蝇酮(cuelure)(别名)(179)+TX、环氧十九烷(disparlure)(277)+TX、十二碳-8-烯-1-基乙酸酯(IUPAC名称)(286)+TX、十二碳-9-烯-1-基乙酸酯(IUPAC名称)(287)+TX、十二碳-8+TX、10-二烯-1-基乙酸酯(IUPAC名称)(284)+TX、dominicalure(别名)[CCN]+TX、4-甲基辛酸乙酯(IUPAC名称)(317)+TX、丁香酚(别名)[CCN]+TX、南部松小蠹集合信息素(frontalin)(别名)[CCN]+TX、诱虫十六酯(gossyplure)(别名)(420)+TX、诱杀烯混剂(grandlure)(421)+TX、诱杀烯混剂I(别名)(421)+TX、诱杀烯混剂II(别名)(421)+TX、诱杀烯混剂III(别名)(421)+TX、诱杀烯混剂IV(别名)(421)+TX、己诱剂(hexalure)[CCN]+TX、齿小蠹二烯醇(ipsdienol)(别名)[CCN]+TX、小蠢烯醇(ipsenol)(别名)[CCN]+TX、金龟子性诱剂(japonilure)(别名)(481)+TX、三甲基二氧三环壬烷(lineatin)(别名)[CCN]+TX、litlure(别名)[CCN]+TX、粉纹夜蛾性诱剂(looplure)(别名)[CCN]+TX、诱杀酯(medlure)[CCN]+TX、megatomoic acid(别名)[CCN]+TX、诱虫醚(methyl eugenol)(别名)(540)+TX、诱虫烯(muscalure)(563)+TX、十八碳-2,13-二烯-1-基乙酸酯(IUPAC名称)(588)+TX、十八碳-3,13-二烯-1-基乙酸酯(IUPAC名称)(589)+TX、贺康彼(orfralure)(别名)[CCN]+TX、椰蛀犀金龟聚集信息素(oryctalure)(别名)(317)+TX、非乐康(ostramone)(别名)[CCN]+TX、诱虫环(siglure)[CCN]+TX、sordidin(别名)(736)+TX、食菌甲诱醇(sulcatol)(别名)[CCN]+TX、十四碳-11-烯-1-基乙酸酯(IUPAC名称)(785)+TX、地中海实蝇引诱剂(839)+TX、地中海实蝇引诱剂A(别名)(839)+TX、地中海实蝇引诱剂B1(别名)(839)+TX、地中海实蝇引诱剂B2(别名)(839)+TX、地中海实蝇引诱剂C(别名)(839)和trunc-call(别名)[CCN]+TX;
昆虫驱避剂,其选自由以下组成的物质组:2-(辛基硫代)乙醇(IUPAC名称)(591)+TX、避蚊酮(butopyronoxyl)(933)+TX、丁氧基(聚丙二醇)(936)+TX、己二酸二丁酯(IUPAC名称)(1046)+TX、邻苯二甲酸二丁酯(1047)+TX、丁二酸二丁酯(IUPAC名称)(1048)+TX、避蚊胺[CCN]+TX、驱蚊灵(dimethyl carbate)[CCN]+TX、邻苯二甲酸二甲酯[CCN]+TX、乙基己二醇(1137)+TX、己脲[CCN]+TX、甲喹丁(methoquin-butyl)(1276)+TX、甲基新癸酰胺[CCN]+TX、草氨酸盐(oxamate)[CCN]和派卡瑞丁[CCN]+TX;
杀软体动物剂,其选自由以下组成的物质组:二(三丁基锡)氧化物(IUPAC名称)(913)+TX、溴乙酰胺[CCN]+TX、砷酸钙[CCN]+TX、除线威(999)+TX、乙酰亚砷酸铜[CCN]+TX、硫酸铜(172)+TX、三苯锡(347)+TX、磷酸铁(IUPAC名称)(352)+TX、四聚乙醛(518)+TX、灭虫威(530)+TX、氯硝柳胺(576)+TX、氯硝柳胺-乙醇胺(576)+TX、五氯酚(623)+TX、五氯苯氧化钠(623)+TX、噻螨威(tazimcarb)(1412)+TX、硫双威(799)+TX、三丁基氧化锡(913)+TX、蜗螺杀(trifenmorph)(1454)+TX、混杀威(trimethacarb)(840)+TX、三苯基乙酸锡(IUPAC名称)(347)和三苯基氢氧化锡(IUPAC名称)(347)+TX、吡唑虫啶(pyriprole)[394730-71-3]+TX;
杀线虫剂,其选自由以下组成的物质组:AKD-3088(化合物代码)+TX、1,2-二溴-3-氯丙烷(IUPAC/化学文摘名称)(1045)+TX、1,2-二氯丙烷(IUPAC/化学文摘名称)(1062)+TX、1,2-二氯丙烷与1,3-二氯丙烯(IUPAC名称)(1063)+TX、1,3-二氯丙烯(233)+TX、3,4-二氯四氢噻吩1,1-二氧化物(IUPAC/化学文摘名称)(1065)+TX、3-(4-氯苯基)-5-甲基罗丹宁(IUPAC名称)(980)+TX、5-甲基-6-硫代-1,3,5-噻二嗪-3-基乙酸(IUPAC名称)(1286)+TX、6-异戊烯基氨基嘌呤(别名)(210)+TX、阿维菌素(1)+TX、乙酰虫腈[CCN]+TX、棉铃威(15)+TX、涕灭威(aldicarb)(16)+TX、涕灭砜威(863)+TX、AZ 60541(化合物代码)+TX、苯氯噻(benclothiaz)[CCN]+TX、苯菌灵(62)+TX、丁基哒螨灵(别名)+TX、克线丹(109)+TX、克百威(carbofuran)(118)+TX、二硫化碳(945)+TX、丁硫克百威(119)+TX、氯化苦(141)+TX、毒死蜱(145)+TX、除线威(999)+TX、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,其选自由以下组成的物质组:乙基黄原酸钾[CCN]以及氯啶(nitrapyrin)(580)+TX;
植物活化剂,其选自由以下组成的物质组:阿拉酸式苯(acibenzolar)(6)+TX、阿拉酸式苯-S-甲基(6)+TX、噻菌灵(probenazole)(658)和大虎杖(Reynoutriasachalinensis)提取物(别名)(720)+TX;
杀鼠剂,其选自由以下组成的物质组:2-异戊酰茚满-1,3-二酮(IUPAC名称)(1246)+TX、4-(喹喔啉-2-基氨基)苯磺酰胺(IUPAC名称)(748)+TX、α-氯代醇[CCN]+TX、磷化铝(640)+TX、安妥(880)+TX、三氧化二砷(882)+TX、碳酸钡(891)+TX、双鼠脲(912)+TX、溴鼠隆(89)+TX、溴敌隆(包括α-溴敌隆)+TX、溴鼠胺(92)+TX、氰化钙(444)+TX、氯醛糖(127)+TX、氯鼠酮(140)+TX、胆钙化醇(别名)(850)+TX、氯灭鼠灵(1004)+TX、克灭鼠(1005)+TX、杀鼠萘(175)+TX、杀鼠嘧啶(1009)+TX、鼠得克(246)+TX、噻鼠灵(249)+TX、敌鼠(273)+TX、钙化醇(301)+TX、氟鼠灵(357)+TX、氟乙酰胺(379)+TX、氟鼠啶(1183)+TX、氟鼠啶盐酸盐(1183)+TX、γ-HCH(430)+TX、HCH(430)+TX、氰化氢(444)+TX、碘甲烷(IUPAC名称)(542)+TX、林旦(430)+TX、磷化镁(IUPAC名称)(640)+TX、溴甲烷(537)+TX、鼠特灵(1318)+TX、毒鼠磷(1336)+TX、磷化氢(IUPAC名称)(640)+TX、磷[CCN]+TX、杀鼠酮(1341)+TX、亚砷酸钾[CCN]+TX、灭鼠优(1371)+TX、海葱糖苷(1390)+TX、亚砷酸钠[CCN]+TX、氰化钠(444)+TX、氟乙酸钠(735)+TX、士的宁(745)+TX、硫酸铊[CCN]+TX、杀鼠灵(851)以及磷化锌(640)+TX;
增效剂,其选自由以下组成的物质组:2-(2-丁氧基乙氧基)乙基胡椒酸酯(IUPAC名称)(934)+TX、5-(1,3-苯并间二氧杂环戊烯-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、MGK 264(研究代码)(296)+TX、增效醚(piperonyl butoxide)(649)+TX、增效醛(piprotal)(1343)+TX、增效酯(propyl isomer)(1358)+TX、S421(研究代码)(724)+TX、增效散(sesamex)(1393)+TX、芝麻林素(sesasmolin)(1394)和亚砜(1406)+TX;
动物驱避剂,其自由以下组成的物质组:蒽醌(32)+TX、氯醛糖(127)+TX、环烷酸铜[CCN]+TX、王铜(171)+TX、二嗪磷(227)+TX、二环戊二烯(化学名称)(1069)+TX、双胍辛盐(guazatine)(422)+TX、双胍辛乙酸盐(422)+TX、灭虫威(530)+TX、吡啶-4-胺(IUPAC名称)(23)+TX、塞仑(804)+TX、混杀威(trimethacarb)(840)+TX、环烷酸锌[CCN]和福美锌(856)+TX;
杀病毒剂,其选自由以下组成的物质组:衣马宁(别名)[CCN]和利巴韦林(别名)[CCN]+TX;
创伤保护剂,其选自由以下组成的物质组:氧化汞(512)+TX、辛噻酮(octhilinone)(590)和甲基托布津(802)+TX;
生物活性物质,其选自1,1-双(4-氯-苯基)-2-乙氧基乙醇+TX、2,4-二氯苯基苯磺酸酯+TX、2-氟-N-甲基-N-1-萘乙酰胺+TX、4-氯苯基苯基砜+TX、乙酰虫腈+TX、涕灭砜威+TX、赛果+TX、果满磷+TX、胺吸磷+TX、草酸氢胺吸磷+TX、双甲脒+TX、杀螨特+TX、三氧化二砷+TX、偶氮苯+TX、偶氮磷+TX、苯菌灵+TX、苯诺沙磷(benoxa-fos)+TX、苯甲酸苄酯+TX、联苯吡菌胺+TX、溴灭菊酯+TX、溴烯杀+TX、溴硫磷+TX、溴螨酯+TX、噻嗪酮+TX、丁酮威+TX、丁酮砜威+TX、丁基哒螨灵+TX、多硫化钙+TX、八氯莰烯+TX、氯灭杀威+TX、三硫磷+TX、螨蜱胺+TX、灭螨猛+TX、杀螨醚+TX、杀虫脒+TX、杀虫脒盐酸盐+TX、杀螨醇+TX、杀螨酯+TX、敌螨特+TX、乙酯杀螨醇+TX、灭螨脒(chloromebuform)+TX、灭虫脲+TX、丙酯杀螨醇+TX、虫螨磷+TX、瓜菊酯I+TX、瓜菊酯II+TX、瓜菊酯+TX、克罗散泰+TX、蝇毒磷+TX、克罗米通+TX、巴毒磷+TX、硫杂灵+TX、果虫磷+TX、DCPM+TX、DDT+TX、田乐磷+TX、田乐磷-O+TX、田乐磷-S+TX、内吸磷-甲基+TX、内吸磷-O+TX、内吸磷-O-甲基+TX、内吸磷-S+TX、内吸磷-S-甲基+TX、磺吸磷(demeton-S-methylsulfon)+TX、抑菌灵+TX、敌敌畏+TX、dicliphos+TX、除螨灵+TX、甲氟磷+TX、消螨酚(dinex)+TX、消螨酚(dinex-diclexine)+TX、敌螨普-4+TX、敌螨普-6+TX、邻敌螨消+TX、硝戊酯+TX、硝辛酯杀螨剂+TX、硝丁酯+TX、敌杀磷+TX、磺基二苯+TX、戒酒硫+TX、DNOC+TX、苯氧炔螨(dofenapyn)+TX、多拉克汀+TX、因毒磷+TX、依立诺克丁+TX、益硫磷+TX、乙嘧硫磷+TX、抗螨唑+TX、苯丁锡+TX、苯硫威+TX、fenpyrad+TX、唑螨酯+TX、胺苯吡菌酮+TX、除螨酯+TX、氟硝二苯胺(fentrifanil)+TX、氟螨噻+TX、氟螨脲+TX、联氟螨+TX、氟杀螨+TX、FMC 1137+TX、伐虫脒+TX、伐虫脒盐酸盐+TX、胺甲威(formparanate)+TX、γ-HCH+TX、果绿定+TX、苄螨醚+TX、十六烷基环丙烷羧酸酯+TX、水胺硫磷+TX、茉莉菊酯I+TX、茉莉菊酯II+TX、碘硫磷+TX、林丹+TX、丙螨氰+TX、灭蚜磷+TX、二噻磷+TX、甲硫芬+TX、虫螨畏+TX、溴甲烷+TX、速灭威+TX、自克威+TX、米尔贝肟+TX、丙胺氟+TX、久效磷+TX、茂果+TX、莫昔克丁+TX、二溴磷(naled)+TX、4-氯-2-(2-氯-2-甲基-丙基)-5-[(6-碘-3-吡啶基)甲氧基]哒嗪-3-酮+TX、氟蚁灵+TX、尼可霉素+TX、戊氰威+TX、戊氰威1:1氯化锌络合物+TX、氧乐果+TX、亚异砜磷+TX、砜拌磷+TX、pp'-DDT+TX、对硫磷+TX、苄氯菊酯+TX、芬硫磷+TX、伏杀磷+TX、硫环磷+TX、磷胺+TX、氯化松节油(polychloroterpenes)+TX、杀螨素(polynactins)+TX、丙氯诺+TX、蜱虱威+TX、残杀威+TX、乙噻唑磷+TX、发疏磷+TX、除虫菊酯I+TX、除虫菊酯II+TX、除虫菊酯+TX、哒嗪硫磷+TX、嘧硫磷+TX、喹硫磷(quinalphos)+TX、喹硫磷(quintiofos)+TX、R-1492+TX、甘氨硫磷+TX、鱼藤酮+TX、八甲磷+TX、克线丹+TX、司拉克丁+TX、苏硫磷+TX、SSI-121+TX、舒非仑+TX、氟虫胺+TX、硫特普+TX、硫+TX、氟螨嗪+TX、τ-氟胺氰菊酯+TX、TEPP+TX、叔丁威+TX、四氯杀螨砜+TX、杀螨好+TX、thiafenox+TX、抗虫威+TX、久效威+TX、甲基乙拌磷+TX、克杀螨+TX、苏力菌素+TX、威菌磷+TX、苯螨噻+TX、三唑磷+TX、灭蚜唑(triazuron)+TX、三氯丙氧磷+TX、三活菌素+TX、蚜灭多+TX、甲烯氟虫腈(vaniliprole)+TX、百杀辛(bethoxazin)+TX、二辛酸铜+TX、硫酸铜+TX、cybutryne+TX、二氯萘醌+TX、双氯酚+TX、茵多酸+TX、三苯锡+TX、熟石灰+TX、代森钠+TX、灭藻醌+TX、醌萍胺+TX、西玛津+TX、三苯基乙酸锡+TX、三苯基氢氧化锡+TX、育畜磷+TX、哌嗪+TX、托布津+TX、氯醛糖+TX、倍硫磷+TX、吡啶-4-胺+TX、士的宁+TX、1-羟基-1H-吡啶-2-硫酮+TX、4-(喹喔啉-2-基氨基)苯磺酰胺+TX、8-羟基喹啉硫酸盐+TX、溴硝醇+TX、氢氧化铜+TX、甲酚+TX、双吡硫翁+TX、多地辛+TX、敌磺钠+TX、甲醛+TX、汞加芬+TX、春雷霉素+TX、春雷霉素盐酸盐水合物+TX、双(二甲基二硫代氨基甲酸)镍+TX、三氯甲基吡啶+TX、辛噻酮+TX、奥索利酸+TX、土霉素+TX、羟基喹啉硫酸钾+TX、噻菌灵+TX、链霉素+TX、链霉素倍半硫酸盐+TX、叶枯酞+TX、硫柳汞+TX、棉褐带卷蛾GV+TX、放射形土壤杆菌+TX、钝绥螨属物种(Amblyseius spp.)+TX、芹菜夜蛾NPV+TX、原樱翅缨小蜂(Anagrus atomus)+TX、短距蚜小蜂(Aphelinus abdominalis)+TX、棉蚜寄生蜂(Aphidius colemani)+TX、食蚜瘿蚊(Aphidoletes aphidimyza)+TX、苜蓿银纹夜蛾NPV+TX、球形芽孢杆菌(Bacillus sphaericus Neide)+TX、布氏白僵菌(Beauveriabrongniartii)+TX、普通草蛉(Chrysoperla carnea)+TX、孟氏隐唇瓢虫(Cryptolaemusmontrouzieri)+TX、苹果蠹蛾GV+TX、西伯利亚离颚茧蜂(Dacnusa sibirica)+TX、豌豆潜叶蝇姬小蜂(Diglyphus isaea)+TX、丽蚜小蜂(Encarsia formosa)+TX、桨角蚜小蜂(Eretmocerus eremicus)+TX、嗜菌异小杆线虫(Heterorhabditis bacteriophora)和大异小杆线虫(H.megidis)+TX、斑长足瓢虫(Hippodamia convergens)+TX、橘粉介壳虫寄生蜂(Leptomastix dactylopii)+TX、盲蝽(Macrolophus caliginosus)+TX、甘蓝夜蛾NPV+TX、黄阔柄跳小蜂(Metaphycus helvolus)+TX、黄绿绿僵菌(Metarhizium anisopliaevar.acridum)+TX、金龟子绿僵菌小孢变种(Metarhizium anisopliae var.anisopliae)+TX、欧洲新松叶蜂(Neodiprion sertifer)NPV和红头新松叶蜂(N.lecontei)NPV+TX、小花蝽属物种+TX、玫烟色拟青霉(Paecilomyces fumosoroseus)+TX、智利小植绥螨(Phytoseiulus persimilis)+TX、毛蚊线虫(Steinernema bibionis)+TX、小卷蛾斯氏线虫(Steinernema carpocapsae)+TX、夜蛾斯氏线虫+TX、格氏线虫(Steinernema glaseri)+TX、锐比斯氏线虫(Steinernema riobrave)+TX、Steinernema riobravis+TX、蝼蛄斯氏线虫(Steinernema scapterisci)+TX、斯氏线虫属物种(Steinernema spp.)+TX、赤眼蜂属物种+TX、西方盲走螨(Typhlodromus occidentalis)+TX、蜡蚧轮枝菌(Verticilliumlecanii)+TX、唑磷嗪(apholate)+TX、双(氮丙啶)甲氨基膦硫化物(bisazir)+TX、白消安+TX、迪麦替夫(dimatif)+TX、六甲蜜胺(hemel)+TX、六甲磷(hempa)+TX、甲基涕巴(metepa)+TX、甲硫涕巴(methiotepa)+TX、甲基唑磷嗪(methyl apholate)+TX、不孕啶(morzid)+TX、氟幼脲(penfluron)+TX、涕巴(tepa)+TX、硫代六甲磷(thiohempa)+TX、硫涕巴+TX、曲他胺+TX、尿烷亚胺+TX、(E)-癸-5-烯-1-基乙酸酯与(E)-癸-5-烯-1-醇+TX、(E)-十三碳-4-烯-1-基乙酸酯+TX、(E)-6-甲基庚-2-烯-4-醇+TX、(E,Z)-十四碳-4,10-二烯-1-基乙酸酯+TX、(Z)-十二碳-7-烯-1-基乙酸酯+TX、(Z)-十六碳-11-烯醛+TX、(Z)-十六碳-11-烯-1-基乙酸酯+TX、(Z)-十六碳-13-烯-11-炔-1-基乙酸酯+TX、(Z)-二十-13-烯-10-酮+TX、(Z)-十四碳-7-烯-1-醛+TX、(Z)-十四碳-9-烯-1-醇+TX、(Z)-十四碳-9-烯-1-基乙酸酯+TX、(7E,9Z)-十二碳-7,9-二烯-1-基乙酸酯+TX、(9Z,11E)-十四碳-9,11-二烯-1-基乙酸酯+TX、(9Z,12E)-十四碳-9,12-二烯-1-基乙酸酯+TX、14-甲基十八碳-1-烯+TX、4-甲基壬-5-醇与4-甲基壬-5-酮+TX、α-多纹素+TX、西部松小蠹集合信息素+TX、十二碳二烯醇(codlelure)+TX、可得蒙(codlemone)+TX、诱蝇酮(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、丁香酚+TX、南部松小蠹集合信息素(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、己诱剂(hexalure)+TX、齿小蠹二烯醇(ipsdienol)+TX、小蠢烯醇(ipsenol)+TX、金龟子性诱剂(japonilure)+TX、三甲基二氧三环壬烷(lineatin)+TX、litlure+TX、粉纹夜蛾性诱剂(looplure)+TX、诱杀酯(medlure)+TX、megatomoic acid+TX、诱虫醚(methyl eugenol)+TX、诱虫烯(muscalure)+TX、十八碳-2,13-二烯-1-基乙酸酯+TX、十八碳-3,13-二烯-1-基乙酸酯+TX、贺康彼(orfralure)+TX、椰蛀犀金龟聚集信息素(oryctalure)+TX、非乐康(ostramone)+TX、诱虫环(siglure)+TX、sordidin+TX、食菌甲诱醇(sulcatol)+TX、十四碳-11-烯-1-基乙酸酯+TX、地中海实蝇引诱剂(trimedlure)+TX、地中海实蝇引诱剂A+TX、地中海实蝇引诱剂B1+TX、地中海实蝇引诱剂B2+TX、地中海实蝇引诱剂C+TX、trunc-call+TX、2-(辛基硫代)-乙醇+TX、避蚊酮(butopyronoxyl)+TX、丁氧基(聚丙二醇)+TX、己二酸二丁酯+TX、邻苯二甲酸二丁酯+TX、丁二酸二丁酯+TX、避蚊胺+TX、驱蚊灵(dimethyl carbate)+TX、邻苯二甲酸二甲酯+TX、乙基己二醇+TX、己脲(hexamide)+TX、甲喹丁(methoquin-butyl)+TX、甲基新癸酰胺(methylneodecanamide)+TX、草氨酸盐(oxamate)+TX、派卡瑞丁(picaridin)+TX、1-二氯-1-硝基乙烷+TX、1,1-二氯-2,2-二(4-乙基苯基)乙烷+TX、1,2-二氯丙烷与1,3-二氯丙烯+TX、1-溴-2-氯乙烷+TX、2,2,2-三氯-1-(3,4-二氯苯基)乙基乙酸酯+TX、2,2-二氯乙烯基2-乙基亚磺酰基乙基甲基磷酸酯+TX、2-(1,3-二硫戊环-2-基)苯基二甲基氨基甲酸酯+TX、2-(2-丁氧基乙氧基)乙基硫氰酸酯+TX、2-(4,5-二甲基-1,3-二氧戊环-2-基)苯基甲基氨基甲酸酯+TX、2-(4-氯-3,5-二甲苯基氧基)乙醇+TX、2-氯乙烯基二乙基磷酸酯+TX、2-咪唑啉酮+TX、2-异戊酰茚满-1,3-二酮+TX、2-甲基(丙-2-炔基)氨基苯基甲基氨基甲酸酯+TX、2-氰硫基乙基月桂酸酯+TX、3-溴-1-氯丙-1-烯+TX、3-甲基-1-苯基吡唑-5-基二甲基氨基甲酸酯+TX、4-甲基(丙-2-炔基)氨基-3,5-二甲苯基甲基氨基甲酸酯+TX、5,5-二甲基-3-氧代环己-1-烯基二甲基氨基甲酸酯+TX、阿赛硫磷+TX、丙烯腈+TX、艾氏剂+TX、阿洛氨菌素+TX、除害威+TX、α-蜕化素+TX、磷化铝+TX、灭害威+TX、新烟碱+TX、乙基杀扑磷(athidathion)+TX、甲基吡啶磷+TX、苏云金芽孢杆菌δ-内毒素+TX、六氟硅酸钡+TX、多硫化钡+TX、熏菊酯+TX、拜耳22/190+TX、拜耳22408+TX、β-氟氯氰菊酯+TX、β-氯氰菊酯+TX、戊环苄呋菊酯(bioethanomethrin)+TX、生物氯菊酯+TX、双(2-氯乙基)醚+TX、硼砂+TX、溴苯烯磷+TX、溴-DDT+TX、合杀威+TX、畜虫威+TX、特嘧硫磷(butathiofos)+TX、丁酯磷+TX、砷酸钙+TX、氰化钙+TX、二硫化碳+TX、四氯化碳+TX、巴丹盐酸盐+TX、瑟瓦定(cevadine)+TX、冰片丹+TX、氯丹+TX、十氯酮+TX、氯仿+TX、氯化苦+TX、氯腈肟磷+TX、氯吡唑磷(chlorprazophos)+TX、顺式苄呋菊酯(cis-resmethrin)+TX、顺式苄呋菊酯(cismethrin)+TX、氰菊酯(clocythrin)(别名)+TX、乙酰亚砷酸铜+TX、砷酸铜+TX、油酸铜+TX、畜虫磷(coumithoate)+TX、冰晶石+TX、CS 708+TX、苯腈磷+TX、杀螟腈+TX、环虫菊+TX、赛灭磷+TX、d-胺菊酯+TX、DAEP+TX、棉隆+TX、脱甲基克百威(decarbofuran)+TX、除线特(diamidafos)+TX、异氯磷+TX、除线磷+TX、dicresyl+TX、环虫腈+TX、狄氏剂+TX、二乙基5-甲基吡唑-3-基磷酸酯+TX、喘定(dior)+TX、四氟甲醚菊酯+TX、地麦威+TX、苄菊酯+TX、甲基毒虫畏+TX、敌蝇威+TX、丙硝酚+TX、戊硝酚+TX、地乐酚+TX、苯虫醚+TX、蔬果磷+TX、噻喃磷+TX、DSP+TX、脱皮甾酮+TX、EI 1642+TX、EMPC+TX、EPBP+TX、etaphos+TX、乙硫苯威+TX、甲酸乙酯+TX、二溴乙烷+TX、二氯乙烷+TX、环氧乙烷+TX、EXD+TX、皮蝇磷+TX、乙苯威+TX、杀螟硫磷+TX、氧嘧酰胺(fenoxacrim)+TX、吡氯氰菊酯+TX、丰索磷+TX、乙基倍硫磷+TX、氟氯双苯隆(flucofuron)+TX、丁苯硫磷+TX、磷砒酯+TX、丁环硫磷+TX、呋线威+TX、抗虫菊+TX、双胍辛盐+TX、双胍辛乙酸盐+TX、四硫代碳酸钠+TX、苄螨醚(halfenprox)+TX、HCH+TX、HEOD+TX、七氯+TX、速杀硫磷+TX、HHDN+TX、氰化氢+TX、喹啉威+TX、IPSP+TX、氯唑磷+TX、碳氯灵+TX、异艾氏剂+TX、异柳磷+TX、移栽灵+TX、稻瘟灵+TX、恶唑磷+TX、保幼激素I+TX、保幼激素II+TX、保幼激素III+TX、氯戊环+TX、烯虫炔酯+TX、砷酸铅+TX、溴苯磷+TX、啶虫磷+TX、噻唑磷+TX、间异丙苯基甲基氨基甲酸酯+TX、磷化镁+TX、叠氮磷+TX、甲基减蚜磷+TX、灭蚜硫磷+TX、氯化亚汞+TX、甲亚砜磷+TX、威百亩+TX、威百亩钾盐+TX、威百亩钠盐+TX、甲基磺酰氟+TX、丁烯胺磷+TX、甲氧普林+TX、甲醚菊酯+TX、甲氧滴滴涕+TX、异硫氰酸甲酯+TX、甲基氯仿+TX、二氯甲烷+TX、恶虫酮+TX、灭蚁灵+TX、奈肽磷+TX、萘+TX、NC-170+TX、烟碱+TX、硫酸烟碱+TX、硝虫噻嗪+TX、原烟碱+TX、O-5-二氯-4-碘代苯基O-乙基乙基硫代膦酸酯+TX、O,O-二乙基O-4-甲基-2-氧代-2H-苯并吡喃-7-基硫代膦酸酯+TX、O,O-二乙基O-6-甲基-2-丙基嘧啶-4-基硫代膦酸酯+TX、O,O,O',O'-四丙基二硫代焦磷酸酯+TX、油酸+TX、对-二氯苯+TX、甲基对硫磷+TX、五氯苯酚+TX、月桂酸五氯苯酯+TX、PH 60-38+TX、芬硫磷+TX、对氯硫磷+TX、磷化氢+TX、甲基辛硫磷+TX、甲胺嘧磷+TX、多氯二环戊二烯异构体+TX、亚砷酸钾+TX、硫氰酸钾+TX、早熟素I+TX、早熟素II+TX、早熟素III+TX、酰胺嘧啶磷+TX、丙氟菊酯+TX、猛杀威+TX、丙硫磷+TX、吡菌磷+TX、反灭虫菊+TX、苦木提取物(quassia)+TX、喹硫磷-甲基+TX、畜宁磷+TX、碘柳胺+TX、苄呋菊脂+TX、鱼藤酮+TX、噻嗯菊酯+TX、鱼尼汀+TX、利阿诺定+TX、沙巴藜芦(sabadilla)+TX、八甲磷+TX、克线丹+TX、SI-0009+TX、噻丙腈+TX、亚砷酸钠+TX、氰化钠+TX、氟化钠+TX、六氟硅酸钠+TX、五氯苯酚钠+TX、硒酸钠+TX、硫氰酸钠+TX、磺苯醚隆(sulcofuron)+TX、磺苯醚隆钠盐(sulcofuron-sodium)+TX、硫酰氟+TX、硫丙磷+TX、焦油+TX、噻螨威+TX、TDE+TX、丁基嘧啶磷+TX、双硫磷+TX、环戊烯丙菊酯+TX、四氯乙烷+TX、噻氯磷+TX、杀虫环+TX、杀虫环草酸盐+TX、虫线磷+TX、杀虫单+TX、杀虫单钠+TX、四溴菊酯+TX、反氯菊酯+TX、唑蚜威+TX、异皮蝇磷-3(trichlormetaphos-3)+TX、毒壤膦+TX、混杀威+TX、三氟甲氧威(tolprocarb)+TX、氯啶菌酯+TX、烯虫硫酯+TX、藜芦定+TX、藜芦碱+TX、XMC+TX、zetamethrin+TX、磷化锌+TX、唑虫磷+TX和氯氟醚菊酯+TX、四氟醚菊酯+TX、双(三丁基锡)氧化物+TX、溴乙酰胺+TX、磷酸铁+TX、氯硝柳胺-乙醇胺+TX、三丁基氧化锡+TX、吡吗啉+TX、蜗螺杀+TX、1,2-二溴-3-氯丙烷+TX、1,3-二氯丙烯+TX、3,4-二氯四氢噻吩1,1-二氧化物+TX、3-(4-氯苯基)-5-甲基罗丹宁+TX、5-甲基-6-硫代-1,3,5-噻二嗪-3-基乙酸+TX、6-异戊烯基氨基嘌呤+TX、2-氟-N-(3-甲氧基苯基)-9H-嘌呤-6-胺+TX、苯氯噻(benclothiaz)+TX、细胞分裂素+TX、DCIP+TX、糠醛+TX、异酰胺磷(isamidofos)+TX、激动素+TX、疣孢漆斑菌组合物+TX、四氯噻吩+TX、二甲苯酚+TX、玉米素+TX、乙基黄原酸钾+TX、阿拉酸式苯+TX、阿拉酸式苯-S-甲基+TX、大虎杖(Reynoutria sachalinensis)提取物+TX、α-氯代醇+TX、安妥+TX、碳酸钡+TX、双鼠脲+TX、溴鼠隆+TX、溴敌隆+TX、溴鼠胺+TX、氯鼠酮+TX、胆钙化醇+TX、氯杀鼠灵+TX、克灭鼠+TX、杀鼠萘+TX、杀鼠嘧啶+TX、鼠得克+TX、噻鼠灵+TX、敌鼠+TX、钙化醇+TX、氟鼠灵+TX、氟乙酰胺+TX、氟鼠啶+TX、氟鼠啶盐酸盐+TX、鼠特灵+TX、毒鼠磷+TX、磷+TX、杀鼠酮+TX、灭鼠优+TX、海葱糖苷+TX、氟乙酸钠+TX、硫酸铊+TX、杀鼠灵+TX、2-(-2-丁氧基乙氧基)乙基胡椒酸酯+TX、5-(1,3-苯并间二氧杂环戊烯-5-基)-3-己基环己-2-烯酮+TX、具有橙花叔醇的法呢醇+TX、增效炔醚+TX、MGK 264+TX、增效醚+TX、增效醛+TX、增效酯(propyl isomer)+TX、S421+TX、增效散+TX、芝麻林素(sesasmolin)+TX、亚砜+TX、蒽醌+TX、环烷酸铜+TX、王铜+TX、二环戊二烯+TX、塞仑+TX、环烷酸锌+TX、福美锌+TX、衣马宁+TX、利巴韦林+TX、氯吲哚酰肼(chloroinconazide)+TX、氧化汞+TX、甲基托布津+TX、阿扎康唑+TX、联苯三唑醇+TX、糠菌唑+TX、环唑醇+TX、苯醚甲环唑+TX、烯唑醇+TX、氟环唑+TX、腈苯唑+TX、氟喹唑+TX、氟硅唑+TX、粉唑醇+TX、呋吡菌胺+TX、己唑醇+TX、抑霉唑+TX、亚胺唑+TX、种菌唑+TX、叶菌唑+TX、腈菌唑+TX、多效唑+TX、稻瘟酯+TX、戊菌唑+TX、丙硫菌唑+TX、啶斑肟(pyrifenox)+TX、咪鲜胺+TX、丙环唑+TX、啶菌唑+TX、硅氟唑(simeconazole)+TX、戊唑醇+TX、氟醚唑+TX、三唑酮+TX、三唑醇+TX、氟菌唑+TX、灭菌唑+TX、嘧啶醇+TX、氯苯嘧啶醇+TX、氟苯嘧啶醇+TX、乙嘧酚磺酸酯(bupirimate)+TX、甲菌定(dimethirimol)+TX、乙菌定(ethirimol)+TX、十二环吗啉+TX、苯锈啶(fenpropidin)+TX、丁苯吗啉+TX、螺环菌胺+TX、十三吗啉+TX、嘧菌环胺+TX、嘧菌胺+TX、嘧霉胺(pyrimethanil)+TX、拌种咯+TX、咯菌腈+TX、苯霜灵(benalaxyl)+TX、呋霜灵(furalaxyl)+TX、甲霜灵+TX、R-甲霜灵+TX、呋酰胺+TX、恶霜灵(oxadixyl)+TX、多菌灵+TX、咪菌威(debacarb)+TX、麦穗宁+TX、噻苯达唑+TX、乙菌利(chlozolinate)+TX、菌核利(dichlozoline)+TX、甲菌利(myclozoline)+TX、腐霉利(procymidone)+TX、乙烯菌核利(vinclozoline)+TX、啶酰菌胺(boscalid)+TX、萎锈灵+TX、甲呋酰胺+TX、氟酰胺(flutolanil)+TX、灭锈胺+TX、氧化萎锈灵+TX、吡噻菌胺(penthiopyrad)+TX、噻呋酰胺+TX、多果定+TX、双胍辛胺+TX、嘧菌酯+TX、醚菌胺+TX、烯肟菌酯(enestroburin)+TX、烯肟菌胺+TX、氟菌螨酯+TX、氟嘧菌酯+TX、醚菌酯+TX、苯氧菌胺+TX、肟菌酯+TX、肟醚菌胺+TX、啶氧菌酯+TX、唑菌胺酯+TX、唑胺菌酯+TX、唑菌酯+TX、福美铁+TX、代森锰锌+TX、代森锰+TX、代森联+TX、甲基代森锌+TX、代森锌+TX、敌菌丹+TX、克菌丹+TX、唑呋草+TX、灭菌丹+TX、对甲抑菌灵+TX、波尔多混合剂+TX、氧化铜+TX、代森锰铜+TX、喹啉铜+TX、酞菌酯+TX、克瘟散+TX、异稻瘟净+TX、氯瘟磷+TX、甲基立枯磷+TX、敌菌灵+TX、苯噻菌胺+TX、灭瘟素(blasticidin-S)+TX、地茂散(chloroneb)+TX、百菌清+TX、环氟菌胺+TX、霜脲氰+TX、Cyclobutrifluram+TX、双氯氰菌胺(diclocymet)+TX、哒菌酮(diclomezine)+TX、氯硝胺(dicloran)+TX、乙霉威(diethofencarb)+TX、烯酰吗啉+TX、氟吗啉+TX、二噻农(dithianon)+TX、噻唑菌胺(ethaboxam)+TX、土菌灵(etridiazole)+TX、恶唑菌酮+TX、咪唑菌酮(fenamidone)+TX、稻瘟酰胺(fenoxanil)+TX、嘧菌腙(ferimzone)+TX、氟啶胺(fluazinam)+TX、氟吡菌胺(fluopicolide)+TX、磺菌胺(flusulfamide)+TX、氟唑菌酰胺+TX、环酰菌胺+TX、三乙膦酸铝(fosetyl-aluminium)+TX、恶霉灵(hymexazol)+TX、丙森锌+TX、赛座灭(cyazofamid)+TX、磺菌威(methasulfocarb)+TX、苯菌酮+TX、戊菌隆(pencycuron)+TX、苯酞+TX、多氧霉素(polyoxins)+TX、霜霉威(propamocarb)+TX、吡菌苯威+TX、碘喹唑酮(proquinazid)+TX、咯喹酮(pyroquilon)+TX、苯啶菌酮(pyriofenone)+TX、喹氧灵+TX、五氯硝基苯+TX、噻酰菌胺+TX、咪唑嗪(triazoxide)+TX、三环唑+TX、嗪氨灵+TX、有效霉素+TX、缬菌胺+TX、苯酰菌胺(zoxamide)+TX、双炔酰菌胺(mandipropamid)+TX、氟苯醚酰胺(flubeneteram)+TX、吡唑萘菌胺(isopyrazam)+TX、氟唑环菌胺(sedaxane)+TX、苯并烯氟菌唑+TX、氟唑菌酰羟胺+TX、3-二氟甲基-1-甲基-1H-吡唑-4-甲酸(3',4',5'-三氟-联苯-2-基)-酰胺+TX、异氟斯酰胺(isoflucypram)+TX、异噻菌胺+TX、二甲硝胺(dipymetitrone)+TX、6-乙基-5,7-二氧代-吡咯并[4,5][1,4]二噻英并[1,2-c]异噻唑-3-甲腈+TX、2-(二氟甲基)-N-[3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+TX、4-(2,6-二氟苯基)-6-甲基-5-苯基-哒嗪-3-甲腈+TX、(R)-3-(二氟甲基)-1-甲基-N-[1,1,3-三甲基茚满-4-基]吡唑-4-甲酰胺+TX、4-(2-溴-4-氟-苯基)-N-(2-氯-6-氟-苯基)-2,5-二甲基-吡唑-3-胺+TX、4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺+TX、氟茚唑菌胺+TX、甲香菌酯(jiaxiangjunzhi)+TX、利本米昔安(lvbenmixianan)+TX、二氯苯噻唑(dichlobentiazox)+TX、曼德斯宾(mandestrobin)+TX、3-(4,4-二氟-3,4-二氢-3,3-二甲基异喹啉-1-基)喹诺酮+TX、2-[2-氟-6-[(8-氟-2-甲基-3-喹啉基)氧基]苯基]丙-2-醇+TX、噻哌菌灵(oxathiapiprolin)+TX、N-[6-[[[(1-甲基四唑-5-基)-苯基-亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸叔丁酯+TX、pyraziflumid+TX、inpyrfluxam+TX、trolprocarb+TX、氯氟醚菌唑+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-基)氧基-2,5-二甲基-苯基]-N-乙基-N-甲基-甲脒+TX、[2-[3-[2-[1-[2-[3,5-双(二氟甲基)吡唑-1-基]乙酰基]-4-哌啶基]噻唑-4-基]-4,5-二氢异噁唑-5-基]-3-氯-苯基]甲磺酸盐+TX、N-[6-[[(Z)-[(1-甲基四唑-5-基)-苯基-亚甲基]氨基]氧基甲基]-2-吡啶基]氨基甲酸丁-3-炔酯+TX、N-[[5-[4-(2,4-二甲基苯基)三唑-2-基]-2-甲基-苯基]甲基]氨基甲酸甲酯+TX、3-氯-6-甲基-5-苯基-4-(2,4,6-三氟苯基)哒嗪+TX、pyridachlometyl+TX、3-(二氟甲基)-1-甲基-N-[1,1,3-三甲基茚满-4-基]吡唑-4-甲酰胺+TX、1-[2-[[1-(4-氯苯基)吡唑-3-基]氧基甲基]-3-甲基-苯基]-4-甲基-四唑-5-酮+TX、1-甲基-4-[3-甲基-2-[[2-甲基-4-(3,4,5-三甲基吡唑-1-基)苯氧基]甲基]苯基]四唑-5-酮+TX、aminopyrifen+TX、唑嘧菌胺+TX、吲唑磺菌胺+TX、氟唑菌苯胺+TX、(Z,2E)-5-[1-(4-氯苯基)吡唑-3-基]氧基-2-甲氧基亚氨基-N,3-二甲基-戊-3-烯胺+TX、吡啶菌酰胺+TX、苯吡克咪徳(fenpicoxamid)+TX、异丁乙氧喹啉+TX、伊氟芬喹(ipflufenoquin)+TX、奎富马林(quinofumelin)+TX、异丙噻菌胺+TX、N-[2-[2,4-二氯-苯氧基]苯基]-3-(二氟甲基)-1-甲基-吡唑-4-甲酰胺+TX、N-[2-[2-氯-4-(三氟甲基)苯氧基]苯基]-3-(二氟甲基)-1-甲基-吡唑-4-甲酰胺+TX、苯噻菌酯+TX、氰烯菌酯+TX、5-氨基-1,3,4-噻二唑-2-硫醇锌盐(2:1)+TX、氟吡菌酰胺+TX、氟噻唑菌腈+TX、氟醚菌酰胺+TX、吡丙炔(pyrapropoyne)+TX、哌碳唑(picarbutrazox)+TX、2-(二氟甲基)-N-(3-乙基-1,1-二甲基-茚满-4-基)吡啶-3-甲酰胺+TX、2-(二氟甲基)-N-((3R)-1,1,3-三甲基茚满-4-基)吡啶-3-甲酰胺+TX、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苯甲腈+TX、甲基四脯氨酸(metyltetraprole)+TX、2-(二氟甲基)-N-((3R)-1,1,3-三甲基茚满-4-基)吡啶-3-甲酰胺+TX、α-(1,1-二甲基乙基)-α-[4'-(三氟甲氧基)[1,1'-联苯基]-4-基]-5-嘧啶甲醇+TX、氟沙普罗林(fluoxapiprolin)+TX、烯肟菌酯(enoxastrobin)+TX、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苯甲腈+TX、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-硫烷基-1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苯甲腈+TX、4-[[6-[2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-硫代-4H-1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]苯甲腈+TX、抗倒酯+TX、丁香菌酯+TX、中生菌素+TX、噻菌铜+TX、噻唑锌+TX、阿米托林(amectotractin)+TX、异菌脲+TX、N-辛基-N'-[2-(辛基氨基)乙基]乙烷-1,2-二胺+TX;N'-[5-溴-2-甲基-6-[(1S)-1-甲基-2-丙氧基-乙氧基]-3-吡啶基]-N-乙基-N-甲基-甲脒+TX、N'-[5-溴-2-甲基-6-[(1R)-1-甲基-2-丙氧基-乙氧基]-3-吡啶基]-N-乙基-N-甲基-甲脒+TX、N'-[5-溴-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒+TX、N'-[5-氯-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒+TX、N'-[5-溴-2-甲基-6-(1-甲基-2-丙氧基-乙氧基)-3-吡啶基]-N-异丙基-N-甲基-甲脒+TX(这些化合物可以由WO 2015/155075中描述的方法制备);N'-[5-溴-2-甲基-6-(2-丙氧基丙氧基)-3-吡啶基]-N-乙基-N-甲基-甲脒+TX(此种化合物可以由IPCOM000249876D中描述的方法制备);N-异丙基-N’-[5-甲氧基-2-甲基-4-(2,2,2-三氟-1-羟基-1-苯基-乙基)苯基]-N-甲基-甲脒+TX、N’-[4-(1-环丙基-2,2,2-三氟-1-羟基-乙基)-5-甲氧基-2-甲基-苯基]-N-异丙基-N-甲基-甲脒+TX(这些化合物可以由WO 2018/228896中描述的方法制备);N-乙基-N'-[5-甲氧基-2-甲基-4-[(2-三氟甲基)氧杂环丁-2-基]苯基]-N-甲基-甲脒+TX、N-乙基-N'-[5-甲氧基-2-甲基-4-[(2-三氟甲基)四氢呋喃-2-基]苯基]-N-甲基-甲脒+TX(这些化合物可以由WO 2019/110427中描述的方法制备);N-[(1R)-1-苄基-3-氯-1-甲基-丁-3-烯基]-8-氟-喹啉-3-甲酰胺+TX、N-[(1S)-1-苄基-3-氯-1-甲基-丁-3-烯基]-8-氟-喹啉-3-甲酰胺+TX、N-[(1R)-1-苄基-3,3,3-三氟-1-甲基-丙基]-8-氟-喹啉-3-甲酰胺+TX、N-[(1S)-1-苄基-3,3,3-三氟-1-甲基-丙基]-8-氟-喹啉-3-甲酰胺+TX、N-[(1R)-1-苄基-1,3-二甲基-丁基]-7,8-二氟-喹啉-3-甲酰胺+TX、N-[(1S)-1-苄基-1,3-二甲基-丁基]-7,8-二氟-喹啉-3-甲酰胺+TX、8-氟-N-[(1R)-1-[(3-氟苯基)甲基]-1,3-二甲基-丁基]喹啉-3-甲酰胺+TX、8-氟-N-[(1S)-1-[(3-氟苯基)甲基]-1,3-二甲基-丁基]喹啉-3-甲酰胺+TX、N-[(1R)-1-苄基-1,3-二甲基-丁基]-8-氟-喹啉-3-甲酰胺+TX、N-[(1S)-1-苄基-1,3-二甲基-丁基]-8-氟-喹啉-3-甲酰胺+TX、N-((1R)-1-苄基-3-氯-1-甲基-丁-3-烯基)-8-氟-喹啉-3-甲酰胺+TX、N-((1S)-1-苄基-3-氯-1-甲基-丁-3-烯基)-8-氟-喹啉-3-甲酰胺+TX(这些化合物可以由WO 2017/153380中描述的方法制备);1-(6,7-二甲基吡唑并[1,5-a]吡啶-3-基)-4,4,5-三氟-3,3-二甲基-异喹啉+TX、1-(6,7-二甲基吡唑并[1,5-a]吡啶-3-基)-4,4,6-三氟-3,3-二甲基-异喹啉+TX、4,4-二氟-3,3-二甲基-1-(6-甲基吡唑并[1,5-a]吡啶-3-基)异喹啉+TX、4,4-二氟-3,3-二甲基-1-(7-甲基吡唑并[1,5-a]吡啶-3-基)异喹啉+TX、1-(6-氯-7-甲基-吡唑并[1,5-a]吡啶-3-基)-4,4-二氟-3,3-二甲基-异喹啉+TX(这些化合物可以由WO2017/025510中描述的方法制备);1-(4,5-二甲基苯并咪唑-1-基)-4,4,5-三氟-3,3-二甲基-异喹啉+TX、1-(4,5-二甲基苯并咪唑-1-基)-4,4-二氟-3,3-二甲基-异喹啉+TX、6-氯-4,4-二氟-3,3-二甲基-1-(4-甲基苯并咪唑-1-基)异喹啉+TX、4,4-二氟-1-(5-氟-4-甲基-苯并咪唑-1-基)-3,3-二甲基-异喹啉+TX、3-(4,4-二氟-3,3-二甲基-1-异喹啉基)-7,8-二氢-6H-环戊二烯并[e]苯并咪唑+TX(这些化合物可以由WO 2016/156085中描述的方法制备);N-甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]环丙烷甲酰胺+TX、N,2-二甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺+TX、N-乙基-2-甲基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺+TX、1-甲氧基-3-甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲+TX、1,3-二甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲+TX、3-乙基-1-甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲+TX、N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺+TX、4,4-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮+TX、5,5-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮+TX、1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]吡唑-4-甲酸乙酯+TX、N,N-二甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]-1,2,4-三唑-3-胺+TX。此段落中的化合物可以由WO 2017/055473、WO 2017/055469、WO 2017/093348和WO 2017/118689中描述的方法制备;2-[6-(4-氯苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇+TX(此化合物可以由WO 2017/029179中描述的方法制备);2-[6-(4-溴苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇+TX(此化合物可以由WO 2017/029179中描述的方法制备);3-[2-(1-氯环丙基)-3-(2-氟苯基)-2-羟基-丙基]咪唑-4-甲腈+TX(此化合物可以由WO 2016/156290中描述的方法制备);3-[2-(1-氯环丙基)-3-(3-氯-2-氟-苯基)-2-羟基-丙基]咪唑-4-甲腈+TX(此化合物可以由WO 2016/156290中描述的方法制备);2-氨基-6-甲基-吡啶-3-甲酸(4-苯氧基苯基)甲酯+TX(此化合物可以由WO 2014/006945中描述的方法制备);2,6-二甲基-1H,5H-[1,4]二噻英并[2,3-c:5,6-c']二吡咯-1,3,5,7(2H,6H)-四酮+TX(此化合物可以由WO 2011/138281中描述的方法制备);N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]硫代苯甲酰胺+TX;N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺+TX;(Z,2E)-5-[1-(2,4-二氯苯基)吡唑-3-基]氧基-2-甲氧基亚氨基-N,3-二甲基-戊-3-烯胺+TX(此化合物可以由WO2018/153707中描述的方法制备);N’-(2-氯-5-甲基-4-苯氧基-苯基)-N-乙基-N-甲基-甲脒+TX;N’-[2-氯-4-(2-氟苯氧基)-5-甲基-苯基]-N-乙基-N-甲基-甲脒+TX(此化合物可以由WO 2016/202742中描述的方法制备);2-(二氟甲基)-N-[(3S)-3-乙基-1,1-二甲基-茚满-4-基]吡啶-3-甲酰胺+TX(此化合物可以由WO 2014/095675中描述的方法制备);(5-甲基-2-吡啶基)-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲酮+TX、(3-甲基异噁唑-5-基)-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲酮+TX(这些化合物可以由WO 2017/220485中描述的方法制备);2-氧代-N-丙基-2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙酰胺+TX(此化合物可以由WO 2018/065414中描述的方法制备);1-[[5-[5-(三氟甲基)-1,2,4-噁二唑-3-基]-2-噻吩基]甲基]吡唑-4-甲酸乙酯+TX(此化合物可以由WO2018/158365中描述的方法制备);2,2-二氟-N-甲基-2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙酰胺+TX、N-[(E)-甲氧基亚氨基甲基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺+TX、N-[(Z)-甲氧基亚氨基甲基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺+TX、N-[N-甲氧基-C-甲基-碳酰亚胺基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺+TX(这些化合物可以由WO 2018/202428中描述的方法制备);
微生物,其包括:鲁氏不动杆菌+TX、枝顶孢属真菌+TX+TX、顶头孢霉菌+TX+TX、Acremonium diospyri+TX、Acremonium obclavatum+TX、棉褐带卷蛾颗粒体病毒(AdoxGV)(Capex)+TX、放射形土壤杆菌菌株K84(Galltrol-A)+TX、链格孢菌+TX、决明链格孢+TX、损毁链格孢(Alternaria destruens)(Smolder)+TX、白粉寄生孢(AQ10)+TX、黄曲霉AF36(AF36)+TX、黄曲霉NRRL 21882(Aflaguard)+TX、曲霉属物种+TX、出芽短梗霉菌+TX、固氮螺菌+TX、(MicroAZ+TX、TAZO B)+TX、固氮菌+TX、褐球固氮菌(Azotobacterchroocuccum)(Azotomeal)+TX、固氮菌囊孢(Bionatural Blooming Blossoms)+TX、解淀粉芽孢杆菌+TX、蜡样芽孢杆菌+TX、蚀几丁质芽孢杆菌菌株(Bacillus chitinosporusstrain)CM-1+TX、蚀几丁质芽孢杆菌菌株(Bacillus chitinosporus strain)AQ746+TX、地衣芽孢杆菌菌株HB-2(BiostartTMRhizoboost)+TX、地衣芽孢杆菌菌株3086(EcoGuard+TX、Green Releaf)+TX、环状芽孢杆菌+TX、坚强芽孢杆菌(BioSafe+TX、BioNem-WP+TX、VOTiVO)+TX、坚强芽孢杆菌菌株I-1582+TX、浸麻芽孢杆菌+TX、死海芽孢杆菌(Bacillus marismortui)+TX、巨大芽孢杆菌+TX、蕈状芽孢杆菌菌株AQ726+TX、乳突芽孢杆菌(Milky Spore Powder)+TX、短小芽孢杆菌属物种+TX、短小芽孢杆菌菌株GB34(YieldShield)+TX、短小芽孢杆菌菌株AQ717+TX、短小芽孢杆菌菌株QST 2808(Sonata+TX、Ballad Plus)+TX、球形芽孢杆菌(Bacillus spahericus)(VectoLex)+TX、芽孢杆菌属物种+TX、芽孢杆菌属菌株AQ175+TX、芽孢杆菌属菌株AQ177+TX、芽孢杆菌属菌株AQ178+TX、枯草芽孢杆菌菌株QST 713(CEASE+TX、Serenade+TX、Rhapsody)+TX、枯草芽孢杆菌菌株QST 714(JAZZ)+TX、枯草芽孢杆菌菌株AQ153+TX、枯草芽孢杆菌菌株AQ743+TX、枯草芽孢杆菌菌株QST3002+TX、枯草芽孢杆菌菌株QST3004+TX、解淀粉枯草芽孢杆菌变种菌株FZB24(Taegro+TX、Rhizopro)+TX、苏云金芽孢杆菌Cry 2Ae+TX、苏云金芽孢杆菌Cry1Ab+TX、苏云金芽孢杆菌鲇泽(Bacillus thuringiensis aizawai)GC 91(Agree)+TX、苏云金芽孢杆菌以色列(Bacillus thuringiensis israelensis)(BMP123+TX、Aquabac+TX、VectoBac)+TX、苏云金芽孢杆菌库尔斯塔克(Bacillus thuringiensiskurstaki)(Javelin+TX、Deliver+TX、CryMax+TX、Bonide+TX、Scutella WP+TX、Turilav WP+TX、Astuto+TX、Dipel WP+TX、Biobit+TX、Foray)+TX、苏云金芽孢杆菌库尔斯塔克BMP 123(Baritone)+TX、苏云金芽孢杆菌库尔斯塔克HD-1(Bioprotec-CAF/3P)+TX、苏云金芽孢杆菌菌株BD#32+TX、苏云金芽孢杆菌菌株AQ52+TX、苏云金芽孢杆菌鲇泽变种(Bacillus thuringiensis var.aizawai)(XenTari+TX、DiPel)+TX、细菌属物种(bacteria spp.)(GROWMEND+TX、GROWSWEET+TX、Shootup)+TX、Clavipacter michiganensis噬菌体(AgriPhage)+TX、Bakflor+TX、球孢白僵菌(Beauveria bassiana)(Beaugenic+TX、Brocaril WP)+TX、球孢白僵菌GHA(MycotrolES+TX、Mycotrol O+TX、BotaniGuard)+TX、布氏白僵菌(Beauveria brongniartii)(Engerlingspilz+TX、Schweizer Beauveria+TX、Melocont)+TX、白僵菌属物种(Beauveria spp.)+TX、灰葡萄孢菌(Botrytis cineria)+TX、大豆慢生型根瘤菌(Bradyrhizobium japonicum)(TerraMax)+TX、短短小芽孢杆菌(Brevibacillusbrevis)+TX、苏云金芽孢杆菌拟步行甲(Bacillus thuringiensis tenebrionis)(Novodor)+TX、BtBooster+TX、洋葱伯克霍尔德菌(Burkholderia cepacia)(Deny+TX、Intercept+TX、Blue Circle)+TX、伯克霍尔德菌(Burkholderia gladii)+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 Bioherbicide)+TX、乳酪假丝酵母(Candida butyri)+TX、无名假丝酵母(Candida famata)+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-Coat+TX、Biocure)+TX、清酒假丝酵母(Candidasake)+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-Cide)+TX、球毛壳菌(Chaetomium globosum)(Nova-Cide)+TX、铁杉紫色杆菌(Chromobacterium subtsugae)菌株PRAA4-1T(Grandevo)+TX、枝状枝孢菌(Cladosporium cladosporioides)+TX、尖孢枝孢(Cladosporiumoxysporum)+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)(EndoFine)+TX、尖孢炭疽菌(Colletotrichum acutatum)+TX、盾壳霉(Coniothyrium minitans)(Cotans WG)+TX、盾壳霉属物种(Coniothyrium spp.)+TX、浅白隐球酵母(Cryptococcus albidus)(YIELDPLUS)+TX、土生隐球菌(Cryptococcushumicola)+TX、隐球酵母属infirmo-miniatus+TX、罗伦隐球酵母(Cryptococcuslaurentii)+TX、苹果异形小卷蛾颗粒体病毒(Cryptophlebia leucotreta granulovirus)(Cryptex)+TX、Cupriavidus campinensis+TX、苹果蠹蛾颗粒体病毒(Cydia pomonellagranulovirus)(CYD-X)+TX、苹果蠹蛾颗粒体病毒(Madex+TX、Madex Plus+TX、MadexMax/Carpovirusine)+TX、Cylindrobasidium laeve(Stumpout)+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)(Vektor)+TX、附球菌(Epicoccum nigrum)+TX、黑附球菌(Epicoccum purpurascens)+TX、附球菌属物种+TX、Filobasidium floriforme+TX、锐顶镰孢菌+TX、厚孢镰刀菌+TX、尖孢镰刀菌(Fusaclean/Biofox C)+TX、层出镰刀菌+TX、镰刀菌属物种+TX、白地霉(Galactomyces geotrichum)+TX、链孢粘帚霉(Gliocladium catenulatum)(Primastop+TX、Prestop)+TX、粉红粘帚霉(Gliocladium roseum)+TX、粘帚霉属物种(SoilGard)+TX、绿粘帚霉(Soilgard)+TX、颗粒体病毒(Granupom)+TX、嗜盐盐芽孢杆菌(Halobacillus halophilus)+TX、岸喜盐芽孢杆菌(Halobacillus litoralis)+TX、特氏盐芽孢杆菌(Halobacillus trueperi)+TX、盐单胞菌属物种+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+TX、棉铃虫核型多角体病毒(Helicovex)+TX、谷实夜蛾核型多角体病毒(Gemstar)+TX、异黄酮-芒柄花黄素(Myconate)+TX、柠檬克勒克酵母+TX、克勒克酵母属物种+TX、大链壶菌(Lagenidiumgiganteum)(Laginex)+TX、长孢蜡蚧菌(Lecanicillium longisporum)(Vertiblast)+TX、蝇蚧疥霉(Lecanicillium muscarium)(Vertikil)+TX、舞毒蛾核型多角体病毒(Disparvirus)+TX、嗜盐海球菌+TX、格氏梅拉菌(Meira geulakonigii)+TX、绿僵菌(Met52)+TX、绿僵菌(Destruxin WP)+TX、Metschnikowia fruticola(Shemer)+TX、美极梅奇酵母(Metschnikowia pulcherrima)+TX、Microdochium dimerum(Antibot)+TX、天蓝色小单孢菌(Micromonospora coerulea)+TX、Microsphaeropsis ochracea+TX、恶臭白色真菌(Muscodor albus)620(Muscudor)+TX、Muscodor roseus菌株A3-5+TX、菌根属物种(Mycorrhizae spp.)(AMykor+TX、Root Maximizer)+TX、疣孢漆斑菌菌株AARC-0255(DiTera)+TX、BROS PLUS+TX、Ophiostoma piliferum菌株D97(Sylvanex)+TX、粉质拟青霉(Paecilomyces farinosus)+TX、玫烟色拟青霉(PFR-97+TX、PreFeRal)+TX、淡紫拟青霉(Paecilomyces lilacinus)(Biostat WP)+TX、淡紫拟青霉菌株251(MeloConWG)+TX、多粘类芽孢杆菌+TX、成团泛菌(BlightBan C9-1)+TX、泛菌属物种+TX、巴斯德氏芽菌属物种(Econem)+TX、拟斯扎瓦巴氏杆菌(Pasteuria nishizawae)+TX、黄灰青霉+TX、拜赖青霉(Penicillium billai)(Jumpstart+TX、TagTeam)+TX、短密青霉+TX、常现青霉+TX、灰黄青霉+TX、产紫青霉+TX、青霉菌属物种+TX、纯绿色肯霉+TX、大伏革菌(Phlebiopsis gigantean)(Rotstop)+TX、解磷细菌(Phosphomeal)+TX、隐地疫霉+TX、棕榈疫霉(Devine)+TX、异常毕赤酵母+TX、季也蒙毕赤酵母(Pichia guilermondii)+TX、膜醭毕赤氏酵母+TX、指甲毕赤酵母+TX、树干毕赤酵母+TX、铜绿假单胞菌+TX、致金色假单胞菌(Pseudomonas aureofasciens)(Spot-Less Biofungicide)+TX、洋葱假单胞菌+TX、绿针假单胞菌(AtEze)+TX、皱褶假单胞菌(Pseudomonas corrugate)+TX、荧光假单胞菌菌株A506(BlightBan A506)+TX、恶臭假单胞菌+TX、Pseudomonas reactans+TX、假单胞菌属物种+TX、丁香假单胞菌(Bio-Save)+TX、绿黄假单胞菌+TX、荧光假单胞菌(Zequanox)+TX、Pseudozyma flocculosa菌株PF-A22 UL(Sporodex L)+TX、纵沟柄锈菌(Puccinia canaliculata)+TX、Puccinia thlaspeos(Wood Warrior)+TX、侧雄腐霉菌(Pythium oligandrum)+TX、寡雄腐霉(Polygandron+TX、Polyversum)+TX、缠器腐霉+TX、水生拉恩菌(Rhanella aquatilis)+TX、拉恩菌属物种(Rhanella spp.)+TX、根瘤菌(Rhizobia)(Dormal+TX、Vault)+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(SARRITOR)+TX、柱顶孢霉属物种(Scytalidium spp.)+TX、Scytalidium uredinicola+TX、甜菜夜蛾核型多角体病毒(Spodoptera exigua nuclear polyhedrosis virus)(Spod-X+TX、Spexit)+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 littoralis nucleopolyhedrovirus)(Littovir)+TX、红掷孢酵母(Sporobolomyces roseus)+TX、嗜麦芽寡养单胞菌(Stenotrophomonasmaltophilia)+TX、不吸水链霉菌(Streptomyces ahygroscopicus)+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)(Mycostop)+TX、利迪链霉菌(Streptomyceslydicus)(Actinovate)+TX、利迪链霉菌WYEC-108(ActinoGrow)+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 Biocontrol)+TX、盖姆斯木霉(Trichoderma gamsii)(Tenet)+TX、深绿木霉(Trichoderma atroviride)(Plantmate)+TX、钩状木霉(Trichoderma hamatum)TH 382+TX、哈茨木霉(Trichodermaharzianum rifai)(Mycostar)+TX、哈茨木霉(Trichoderma harzianum)T-22(Trianum-P+TX、PlantShield HC+TX、RootShield+TX、Trianum-G)+TX、哈茨木霉(Trichodermaharzianum)T-39(Trichodex)+TX、非钩木霉(Trichoderma inhamatum)+TX、康宁木霉(Trichoderma koningii)+TX、木霉属物种(Trichoderma spp.)LC 52(Sentinel)+TX、木素木霉(Trichoderma lignorum)+TX、长柄木霉(Trichoderma longibrachiatum)+TX、多孢木霉(Trichoderma polysporum)(Binab T)+TX、紫杉木霉(Trichoderma taxi)+TX、绿色木霉(Trichoderma virens)+TX、绿色木霉(原来称为绿色粘帚霉(Gliocladium virens)GL-21)(SoilGuard)+TX、绿色木霉(Trichoderma viride)+TX、绿色木霉菌株ICC 080(Remedier)+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、Typhula phacorrhiza菌株94671+TX、黑细基格孢(Ulocladium atrum)+TX、奥德曼细基格孢(Ulocladiumoudemansii)(Botry-Zen)+TX、玉蜀黍黑粉菌(Ustilago maydis)+TX、各种细菌和补充微量营养素(Natural II)+TX、各种真菌(Millennium Microbes)+TX、厚垣轮枝孢菌(Verticillium chlamydosporium)+TX、蜡蚧轮枝菌(Verticillium lecanii)(Mycotal+TX、Vertalec)+TX、Vip3Aa20(VIPtera)+TX、死海枝芽孢杆菌(Virgibaclillusmarismortui)+TX、野油菜黄单胞菌pv.Poae(Camperico)+TX、伯氏致病杆菌+TX、嗜线虫致病杆菌;
植物提取物,其包括:松树油(Retenol)+TX、印楝素(Plasma Neem Oil+TX、AzaGuard+TX、MeemAzal+TX、Molt-X+TX、植物IGR(Neemazad+TX、Neemix)+TX、芥花油(Lilly Miller Vegol)+TX、土荆芥(Chenopodium ambrosioides nearambrosioides)(Requiem)+TX、菊花提取物(Crisant)+TX、印楝油提取物(Trilogy)+TX、唇形科(Labiatae)精油(Botania)+TX、丁香-迷迭香-胡椒薄荷和百里香油提取物(Garden insect killer)+TX、甜菜碱(Greenstim)+TX、大蒜+TX、柠檬草油(GreenMatch)+TX、印楝油+TX、猫薄荷(Nepeta cataria)(猫薄荷油)+TX、Nepetacatarina+TX、烟碱+TX、牛至油(MossBuster)+TX、胡麻科(Pedaliaceae)油(Nematon)+TX、除虫菊+TX、皂皮树(Quillaja saponaria)(NemaQ)+TX、大虎杖(Reynoutriasachalinensis)(Regalia+TX、Sakalia)+TX、鱼藤酮(Eco Roten)+TX、芸香科(Rutaceae)植物提取物(Soleo)+TX、大豆油(Ortho ecosense)+TX、茶树油(TimorexGold)+TX、百里香油+TX、AGNIQUEMMF+TX、BugOil+TX、迷迭香-芝麻-胡椒薄荷-百里香和肉桂提取物混合物(EF 300)+TX、丁香-迷迭香和胡椒薄荷提取物混合物(EF 400)+TX、丁香-胡椒薄荷-大蒜油和薄荷混合物(Soil Shot)+TX、高岭土(Screen)+TX、褐藻的贮存葡聚糖(Laminarin);
信息素,其包括:黑头萤火虫信息素(3M Sprayable Blackheaded FirewormPheromone)+TX、苹果蠹蛾信息素(Paramount dispenser-(CM)/Isomate C-Plus)+TX、葡萄小卷叶蛾信息素(3M MEC-GBM Sprayable Pheromone)+TX、卷叶虫信息素(3M MEC–LR Sprayable Pheromone)+TX、家蝇信息素(Muscamone)(Snip7 Fly Bait+TX、Starbar Premium Fly Bait)+TX、梨小食心虫信息素(3M oriental fruit mothsprayable pheromone)+TX、桃透翅蛾(Peachtree Borer)信息素(Isomate-P)+TX、番茄蛲虫(Tomato Pinworm)信息素(3M Sprayable pheromone)+TX、衣透斯特粉末(Entostat powder)(来自棕榈树的提取物)(Exosex CM)+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、Scenturion+TX、Biolure+TX、Check-Mate+TX、薰衣草千里酸酯(Lavandulyl senecioate);
宏生物剂(Macrobial),其包括:短距蚜小蜂+TX、阿尔蚜茧蜂(Aphidius ervi)(Aphelinus-System)+TX、Acerophagus papaya+TX、二星瓢虫(Adalia-System)+TX、二星瓢虫(Adaline)+TX、二星瓢虫(Aphidalia)+TX、串茧跳小蜂(Ageniaspiscitricola)+TX、巢蛾多胚跳小蜂+TX、安德森钝绥螨(Amblyseius andersoni)(Anderline+TX andersoni-System)+TX、加州钝绥螨(Amblyseius californicus)(Amblyline+TX、Spical)+TX、黄瓜钝绥螨(Thripex+TX、Bugline cucumeris)+TX、伪钝绥螨(Fallacis)+TX、斯氏钝绥螨(Bugline swirskii+TX、Swirskii-Mite)+TX、奥氏钝绥螨(WomerMite)+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)(Citripar)+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-System)+TX、短距蚜小蜂(Apheline+TX、Aphiline)+TX、短翅蚜小蜂(Aphelinus asychis)+TX、棉蚜寄生蜂(Aphidiuscolemani)(Aphipar)+TX、阿尔蚜茧蜂(Ervipar)+TX、烟蚜茧蜂+TX、桃赤蚜蚜茧蜂(Aphipar-M)+TX、食蚜瘿蚊(Aphidend)+TX、食蚜瘿蚊(Aphidoline)+TX、岭南黄蚜小蜂+TX、印巴黄蚜小蜂+TX、哈氏长尾啮小蜂(Aprostocetus hagenowii)+TX、蚁形隐翅甲(Atheta coriaria)(Staphyline)+TX、熊蜂属物种+TX、欧洲熊蜂(Natupol Beehive)+TX、欧洲熊蜂(Beeline+TX、Tripol)+TX、Cephalonomia stephanoderis+TX、黑背唇瓢虫(Chilocorus nigritus)+TX、普通草蛉(Chrysoperla carnea)(Chrysoline)+TX、普通草蛉(Chrysopa)+TX、红通草蛉(Chrysoperla rufilabris)+TX、Cirrospilus ingenuus+TX、四带瑟姬小蜂(Cirrospilus quadristriatus)+TX、白星橘啮小蜂(Citrostichusphyllocnistoides)+TX、Closterocerus chamaeleon+TX、Closterocerus属物种+TX、Coccidoxenoides perminutus(Planopar)+TX、泊蚜小蜂(Coccophagus cowperi)+TX、赖食蚧蚜小蜂(Coccophagus lycimnia)+TX、螟黄足盘绒茧蜂+TX、菜蛾绒茧蜂+TX、孟氏隐唇瓢虫(Cryptobug+TX、Cryptoline)+TX、日本方头甲+TX、西伯利亚离颚茧蜂+TX、西伯利亚离颚茧蜂(Minusa)+TX、豌豆潜叶蝇姬小蜂(Diminex)+TX、小黑瓢虫(Delphastuscatalinae)(Delphastus)+TX、Delphastus pusillus+TX、Diachasmimorpha krausii+TX、长尾潜蝇茧蜂+TX、Diaparsis jucunda+TX、阿里食虱跳小蜂(Diaphorencyrtusaligarhensis)+TX、豌豆潜叶蝇姬小蜂+TX、豌豆潜叶蝇姬小蜂(Miglyphus+TX、Digline)+TX、西伯利亚离颚茧蜂(DacDigline+TX、Minex)+TX、歧脉跳小蜂属物种+TX、盾蚧长缨蚜小蜂+TX、丽蚜小蜂(Encarsia max+TX、Encarline+TX、En-Strip)+TX、浆角蚜小蜂(Eretmocerus eremicus)(Enermix)+TX、哥德恩蚜小蜂(Encarsia guadeloupae)+TX、海地恩蚜小蜂(Encarsia haitiensis)+TX、细扁食蚜蝇(Syrphidend)+TX、Eretmocerissiphonini+TX、加州浆角蚜小蜂(Eretmocerus californicus)+TX、浆角蚜小蜂(Eretmocerus eremicus)(Ercal+TX、Eretline e)+TX、浆角蚜小蜂(Eretmoceruseremicus)(Bemimix)+TX、海氏桨角蚜小蜂+TX、蒙氏桨角蚜小蜂(Bemipar+TX、Eretline m)+TX、Eretmocerus siphonini+TX、四斑光缘瓢虫(Exochomusquadripustulatus)+TX、食螨瘿蚊(Feltiella acarisuga)(Spidend)+TX、食螨瘿蚊(Feltiline)+TX、阿里山潜蝇茧蜂+TX、Fopius ceratitivorus+TX、芒柄花黄素(WirlessBeehome)+TX、细腰凶蓟马(Vespop)+TX、西方静走螨(Galendromus occidentalis)+TX、莱氏棱角肿腿蜂(Goniozus legneri)+TX、麦蛾柔茧蜂+TX、异色瓢虫(HarmoBeetle)+TX、异小杆线虫属物种(Lawn Patrol)+TX、嗜菌异小杆线虫(NemaShield HB+TX、Nemaseek+TX、Terranem-Nam+TX、Terranem+TX、Larvanem+TX、B-Green+TX、NemAttack+TX、Nematop)+TX、大异小杆线虫(Heterorhabditis megidis)(Nemasys H+TX、BioNem H+TX、Exhibitline hm+TX、Larvanem-M)+TX、斑长足瓢虫(Hippodamiaconvergens)+TX、尖狭下盾螨(Hypoaspis aculeifer)(Aculeifer-System+TX、Entomite-A)+TX、兵下盾螨(Hypoaspis miles)(Hypoline m+TX、Entomite-M)+TX、黑色枝跗瘿蜂+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)(Leptopar)+TX、长角跳小蜂(Leptomastix epona)+TX、Lindorus lophanthae+TX、Lipolexis oregmae+TX、叉叶绿蝇(Natufly)+TX、茶足柄瘤蚜茧蜂+TX、盲蝽(Macrolophus caliginosus)(Mirical-N+TX、Macroline c+TX、Mirical)+TX、Mesoseiulus longipes+TX、黄色阔柄跳小蜂(Metaphycus flavus)+TX、Metaphycuslounsburyi+TX、角纹脉褐蛉(Milacewing)+TX、黄色花翅跳小蜂(Microterys flavus)+TX、Muscidifurax raptorellus和Spalangia cameroni(Biopar)+TX、Neodryinustyphlocybae+TX、加州新小绥螨+TX、黄瓜新小绥螨(THRYPEX)+TX、伪新小绥螨(Neoseiulus fallacis)+TX、Nesideocoris tenuis(NesidioBug+TX、Nesibug)+TX、古铜黑蝇(Biofly)+TX、狡小花蝽(Orius insidiosus)(Thripor-I+TX、Oriline i)+TX、无毛小花蝽(Orius laevigatus)(Thripor-L+TX、Oriline l)+TX、大臀小花蝽(Orius majusculus)(Orilinem)+TX、小黑花椿象(Thripor-S)+TX、Pauesiajuniperorum+TX、瓢虫柄腹姬小蜂(Pediobius foveolatus)+TX、Phasmarhabditishermaphrodita(Nemaslug)+TX、Phymastichus coffea+TX、粗毛小植绥螨(Phytoseiulusmacropilus)+TX、智利小植绥螨(Spidex+TX、Phytoline p)+TX、斑腹刺益蝽(Podisus)+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)(复合物)+TX、胯姬小蜂属物种(Quadrastichus spp.)+TX、Rhyzobiuslophanthae+TX、澳洲瓢虫+TX、Rumina decollate+TX、Semielacher petiolatus+TX、麦长管蚜(Ervibank)+TX、小卷蛾斯氏线虫(Nematac C+TX、Millenium+TX、BioNem C+TX、NemAttack+TX、Nemastar+TX、Capsanem)+TX、夜蛾斯氏线虫(NemaShield+TX、Nemasys F+TX、BioNem F+TX、Steinernema-System+TX、NemAttack+TX、Nemaplus+TX、Exhibitline sf+TX、Scia-rid+TX、Entonem)+TX、锯蜂线虫(Steinernemakraussei)(Nemasys L+TX、BioNem L+TX、Exhibitline srb)+TX、锐比斯氏线虫(Steinernema riobrave)(BioVector+TX、BioVektor)+TX、蝼蛄斯氏线虫(Steinernema scapterisci)(Nematac S)+TX、斯氏线虫属物种+TX、斯氏科(Steinernematid)属物种(Guardian Nematodes)+TX、深点食螨瓢虫(Stethorus)+TX、亮腹釉小蜂+TX、Tetrastichus setifer+TX、Thripobius semiluteus+TX、中华长尾小蜂(Torymus sinensis)+TX、甘蓝夜蛾赤眼蜂(Tricholine b)+TX、甘蓝夜蛾赤眼蜂(Tricho-Strip)+TX、广赤眼蜂+TX、微小赤眼蜂+TX、玉米螟赤眼蜂+TX、宽脉赤眼蜂(Trichogramma platneri)+TX、短管赤眼蜂+TX、螟黑点瘤姬蜂(Xanthopimplastemmator);
其他生物制剂,其包括:脱落酸+TX、bioSea+TX、银叶菌(Chondrostereumpurpureum)(Chontrol Paste)+TX、盘长孢状刺盘孢(Collego)+TX、辛酸铜(Cueva)+TX、δ捕捉物(Delta trap)(Trapline d)+TX、解淀粉欧文氏菌(Harpin)(ProAct+TX、Ni-HIBIT Gold CST)+TX、磷酸高铁(Ferramol)+TX、漏斗捕捉物(Funnel trap)(Trapline y)+TX、Gallex+TX、Grower's Secret+TX、高油菜素内酯(Homo-brassonolide)+TX、磷酸铁(Lilly Miller Worry Free Ferramol Slug&Snail Bait)+TX、MCP冰雹捕捉物(hail trap)(Trapline f)+TX、寄生性昆虫南美食甲茧蜂(Microctonus hyperodae)+TX、Mycoleptodiscus terrestris(Des-X)+TX、BioGain+TX、Aminomite+TX、Zenox+TX、信息素罗网(Thripline ams)+TX、碳酸氢钾(MilStop)+TX、脂肪酸的钾盐(Sanova)+TX、硅酸钾溶液(Sil-Matrix)+TX、碘化钾+硫氰酸钾(Enzicur)+TX、SuffOil-X+TX、蜘蛛毒+TX、蝗虫微孢子虫(Semaspore OrganicGrasshopper Control)+TX、粘捕捉物(Trapline YF+TX、Rebell Amarillo)+TX以及捕捉物(Takitrapline y+b)+TX;以及
安全剂,如解草嗪+TX、解草酯(包括解草酯-甲基)+TX、环丙磺酰胺+TX、二氯丙烯胺+TX、解草唑(包括解草唑-乙基)+TX、解草啶+TX、氟草肟+TX、解草噁唑+TX、双苯噁唑酸(包括双苯噁唑酸-乙基)+TX、吡唑解草酯(mefenpyr)(包括吡唑解草酯-二乙基)+TX、metcamifen+TX和解草腈+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 Pesticide Common Names,Copyright1995-2004]上获得;例如,化合物“乙酰虫腈”描述于互联网地址http:// www.alanwood.net/pesticides/acetoprole.html。
多数上述活性成分在上文中通过所谓的“通用名”来提及,在个别情形中使用相应的“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”、“惯用名”、“化合物名称”或“开发代码”,或若既不使用那些名称之一也不使用“通用名”,则使用“别名”。“CAS登记号”意指化学文摘登记号。
选自表1至35和表P1至P8中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1至35和表P1至P8中定义的一种化合物的化合物和如上所述的活性成分,优选地是处于从100:1至1:6000的混合比率,尤其是从50:1至1:50,更尤其是处于从20:1至1:20的比率,甚至更尤其从10:1至1:10,非常尤其是从5:1和1:5,尤其优选的是从2:1至1:2的比率,并且从4:1至2:1的比率同样是优选的,尤其是处于1:1、或5:1、或5:2、或5:3、或5:4、或4:1、或4:2、或4:3、或3:1、或3:2、或2:1、或1:5、或2:5、或3:5、或4:5、或1:4、或2:4、或3:4、或1:3、或2:3、或1:2、或1:600、或1:300、或1:150、或1:35、或2:35、或4:35、或1:75、或2:75、或4:75、或1:6000、或1:3000、或1:1500、或1:350、或2:350、或4:350、或1:750、或2:750、或4:750的比率。那些混合比率是按重量计的。
如上所述的混合物可以被用于控制有害生物的方法中,该方法包括将包含如上所述的混合物的组合物施用于有害生物或其环境中,通过手术或疗法用于处理人或动物体的方法以及在人或动物体上实施的诊断方法除外。
包含选自表1至35和表P1至P8中定义的化合物的具有式(I)的化合物以及一种或多种如上所述的活性成分的混合物可以例如以单一的“掺水即用”的形式施用,以组合的喷雾混合物(该混合物由单一活性成分组分的单独配制品构成)(如“桶混制剂”)施用,并且当以顺序的方式(即,在适当短的时间如几小时或几天内一个接一个地)施用时组合使用这些单一活性成分来施用。施用具有式(I)的化合物与如上所述的活性成分的顺序对于实施本发明并不是至关重要的。
根据本发明的组合物还可以包含另外的固体或液体助剂,如稳定剂,例如未环氧化的或环氧化的植物油(例如环氧化的椰子油、菜籽油或大豆油),消泡剂(例如硅油),防腐剂,粘度调节剂,粘合剂和/或增粘剂,肥料或其他用于获得特定效果的活性成分,例如杀细菌剂、杀真菌剂、杀线虫剂、植物活化剂、杀软体动物剂或除草剂。
根据本发明的组合物是以本身已知的方式,在不存在助剂的情况下,例如通过研磨、筛选和/或压缩固体活性成分;和在至少一种助剂的存在下,例如通过紧密混合活性成分与一种或多种助剂和/或将活性成分与一种或多种助剂一起研磨来制备。用于制备组合物的这些方法和用于制备这些组合物的化合物I的用途也是本发明的主题。
这些组合物的施用方法,即控制上述类型的有害生物的方法,如喷雾、雾化、撒粉、刷涂、包衣、撒播或浇灌-它们被选择以适于普遍情况的预期目的-以及这些组合物用于控制上述类型的有害生物的用途是本发明的其他主题。典型的浓度比是在0.1与1000ppm之间、优选在0.1与500ppm之间的活性成分。每公项的施用比率总体上是每公项1g至2000g活性成分、特别是10g/ha至1000g/ha、优选地是10g/ha至600g/ha。
在作物保护领域中,优选的施用方法是施用至植物的叶(叶施用),可能的是选择施用的频率和比率以符合所讨论的有害生物的侵染风险。可替代地,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地加入淹水的稻田中。
本发明的具有式(I)的化合物及其组合物还适合用于保护植物繁殖材料(例如种子,如果实、块茎或籽粒,或者苗圃植物),以对抗上述类型的有害生物。可以用该化合物在种植前对繁殖材料进行处理,例如可以在播种前对种子进行处理。可替代地,该化合物可以施用至种子籽粒(包衣),这是通过将籽粒浸渍入液体组合物中或通过施用固体组合物层实现的。还可能在繁殖材料被种植在施用场地时施用这些组合物,例如在条播期间将这些组合物施入种子犁沟。这些用于植物繁殖材料的处理方法和如此处理的植物繁殖材料是本发明另外的主题。典型的处理比率将取决于待控制的植物和有害生物/真菌,并且通常是在1至200克/100kg的种子之间、优选地在5至150克/100kg的种子之间,如在10至100克/100kg的种子之间。
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。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,尽管成分的或多或少部分可以渗透到种子材料中,这取决于施用的方法。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,本发明使得可获得其上附着有具有式I的化合物的植物繁殖材料。此外,由此使得可获得包含用具有式I的化合物处理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。
本发明的化合物可以凭借在低施用比率下的更大功效和/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(如果必要的话),例如10ppm、5ppm、2ppm、1ppm或0.2ppm;或较低施用比率,如每m2300mg、200mg或100mg AI来证实。通过增加的安全性(针对地上和地下的非目标生物体(如鱼、鸟和蜂)、改进的物理-化学特性或增加的生物可降解性)可以观察到更大的功效。
在本发明的每个方面以及实施例中,“基本上由……组成”以及其变形是“包含”以及其变形的优选实施例,并且“由……组成”以及其变形是“基本上由……组成”以及其变形的优选实施例。
本申请的披露内容使得可获得在本文中披露的实施例的每种组合。
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Ia、Ib中每一种以及表1至35的化合物同样适用。
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可以凭借在低施用比率下的更大功效而区别于已知的化合物,这可以由本领域技术人员使用在实例中概述的实验程序,使用较低的施用比率(如果必要的话),例如50ppm、24ppm、12.5ppm、6ppm、3ppm、1.5ppm、0.8ppm或0.2ppm来证实。
实例B1:黄瓜条叶甲(Diabrotica balteata)(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雾用从10'000ppm DMSO储备溶液制备的水性测试溶液进行处理。在干燥之后,用L2期幼虫对板进行侵染(6至10只/孔)。侵染4天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。
以下化合物在200ppm施用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:
P1.2、P2.1、P2.2、P2.5、P2-17、P3.4、P7.1、P8.1
实例B2:英雄美洲蝽(Euschistus heros)(新热带褐蝽)
将24孔微量滴定板中的琼脂上的大豆叶片用从10'000ppm DMSO储备溶液制备的水性测试溶液进行喷雾。在干燥之后,用N2期若虫对叶片进行侵染。侵染5天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。
以下化合物在200ppm施用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:
P2.1、P8.1
实例B3:小菜蛾(Plutella xylostella)(小菜蛾(Diamond back moth))
将具有人工饲料的24孔微量滴定板通过移液用从10'000ppm DMSO储备溶液制备的水性测试溶液进行处理。在干燥之后,将菜蛾属卵吸移穿过塑料模板到凝胶印迹纸上并且用其封闭板。侵染8天之后,相比于未处理样品,针对死亡率和生长抑制对这些样品进行评估。
以下化合物在200ppm施用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:P1.2、P1.15、P1.51、P2.1、P2.2、P2.5、P2.10、P2.15、P2.16、P5.1、P5.2、P5.3、P7.1、P8.1
实例B4:桃蚜(绿色桃蚜虫)。内在活性
通过移液管将从10'000ppm DMSO储备溶液制备的测试化合物施用到24孔微量滴定板中并且与蔗糖溶液混合。用拉伸的石蜡膜(Parafilm)封闭板。将具有24个孔的塑料模板置于板上,并将侵染的豌豆幼苗直接置于石蜡膜上。用凝胶印迹纸和另一塑料模板封闭受侵染的板,并且然后倒置。侵染5天之后,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:
P1.3、P1.4、P1.22、P1.26
实例B5:二点叶螨(Tetranychus urticae)(二斑叶螨(Two-spotted spider mite)):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8天之后,针对混合种群(活动阶段)的死亡率对这些样品进行评估。
以下化合物在200ppm施用比率下产生至少80%的死亡率:
P1.1、P1.2、P1.3、P1.4、P1.5、P1.6、P1.7、P1.8、P1.10、P1.11、P1.12、P1.13、P1.14、P1.15、P1.16、P1.17、P1.18、P1.19、P1.20、P1.21、P1.22、P1.23、P1.24、P1.25、P1.26、P1.27、P1.28、P1.29、P1.30、P1.31、P1.33、P1.34、P1.35、P1.36、P1.37、P1.39、P1.40、P1.41、P1.42、P1.43、P1.44、P1.45、P1.46、P1.49、P1.50、P1.52、P2.1、P2.2、P2.3、P2.4、P2.5、P2.6、P2.7、P2.8、P2.9、P2.10、P2.11、P2.12、P2.13、P2.17、P3.1、P3.2、P3.3、P3.4、P3.5、P3.6、P3.7、P3.8、P3.9、P4.1、P4.2、P5.2、P6.1、P7.1、P8.1。
Claims (14)
1.一种具有式(I)的化合物
其中
R1是CN、C(=S)NH2或C1-C6-卤代烷基;
R2是H、OH、卤素、C1-C6-烷氧基或C1-C6-卤代烷氧基;
R3是H、卤素、氰基、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-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基、或C1-C6-卤代烷氧基;
R4是H、卤素、氰基、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-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基、或C1-C6-卤代烷氧基;
R5是苯基、被1至3个取代基R6取代的苯基、杂芳基(其是5或6元单环的或9或10元二环的)、被1至3个取代基R7取代的杂芳基(其是5或6元单环的或9或10元二环的);
Q是由式IIa表示的环胺或由式IIb表示的环胺,
其中箭头指示与羰基的连接;
p1是0、1或2并且指示亚甲基数;
p2是0、1或2并且指示亚甲基数;
q1是1或2并且指示亚甲基数;
q2是1或2并且指示亚甲基数;
X是氢、羟基、C1-C6-烷氧基、氰基或卤素;
Y是氰基、C1-C6-烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷基硫烷基-C1-C6-烷基、C1-C6-烷基亚磺酰基-C1-C6-烷基、C1-C6-烷基磺酰基-C1-C6-烷基、C3-C6-烯基硫烷基-C1-C6-烷基、C3-C6-烯基亚磺酰基-C1-C6-烷基、C3-C6-烯基磺酰基-C1-C6-烷基、C3-C6-炔基硫烷基-C1-C6-烷基、C3-C6-炔基亚磺酰基-C1-C6-烷基、C3-C6-炔基磺酰基-C1-C6-烷基、C1-C6-烷氧基羰基、C1-C6-烷氧基羰基氨基、RaRbNC(O)、RcC(O)NRd、ReSO2NRf、RgO-N=CRh、4至6元非芳香族杂环环体系——其中一个或两个碳独立地被氮、氧、硫或磺酰基替代、苯基、被1至3个取代基R8取代的苯基、5或6元单环杂芳基、或被1至3个取代基R9取代的5或6元单环杂芳基;或者
X和Y一起形成到氮的双键,其被基团RmO取代;
A是氰基、C1-C6-氰基烷基、C2-C6-氰基烯基、C3-C6-氰基环烷基、C1-C6-卤代烷基、C2-C6-卤代烯基、C3-C6-卤代环烷基、C1-C6-烷氧基-C1-C6-烷基、C1-C6-烷氧基羰基、C2-C6-烯氧基羰基、C2-C6-炔氧基羰基、C1-C6-烷基硫烷基-C1-C6-烷基、C1-C6-烷基亚磺酰基-C1-C6-烷基、C1-C6-烷基磺酰基-C1-C6-烷基、RiSO2、RjRkNSO2、苯基、被1至3个取代基R10取代的苯基、杂芳基(其是5或6元单环的或9或10元二环的)、或被1至3个取代基R11取代的杂芳基(其是5或6元单环的或9或10元二环的);
Ra和Rb独立地选自氢、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-C6-环烷基和C3-C6-卤代环烷基以及C1-C6-烷基磺酰基;
Rc和Rd独立地选自氢、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-C6-环烷基和C3-C6-卤代环烷基;
Rf是氢、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-C6-环烷基或C3-C6-卤代环烷基;
Re和Ri独立地选自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-C6-环烷基和C3-C6-卤代环烷基;
Rg和Rh独立地选自氢、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-C6-环烷基和C3-C6-卤代环烷基;
Rj和Rk独立地选自氢、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-C6-环烷基和C3-C6-卤代环烷基;
Rm是氢、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-C6-环烷基或C3-C6-卤代环烷基;并且
R6、R7、R8、R9、R10、R11独立地选自卤素、氰基、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-C6-环烷基、C3-C6-卤代环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C1-C6-烷基磺酰基和C1-C6-卤代烷基硫烷基;
或所述具有式I的化合物的农用化学上可接受的盐、立体异构体、对映异构体、互变异构体和N-氧化物。
2.根据权利要求1所述的化合物,其中,p1和p2各自是0,或p1和p2各自是1。
3.根据权利要求1或权利要求2所述的化合物,其中,R1是CN或C(=S)NH2。
4.根据权利要求1至3中任一项所述的化合物,其中,R2是氢并且R4是氢或氰基。
5.根据权利要求1至4中任一项所述的化合物,其中,R5是苯基或被1至3个取代基R6取代的苯基,其中所述R6独立地选自卤素、氰基、C1-C3-烷基、C1-C3-卤代烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、C1-C3-烷基磺酰基和C1-C3-卤代烷基硫烷基。
6.根据权利要求1至5中任一项所述的化合物,其中,Q是式IIa,其中X是氢或羟基;Y是C1-C3-烷基硫烷基-甲基、C1-C3-烷基亚磺酰基-甲基、C1-C3-烷基磺酰基-甲基、C3-C4-烯基硫烷基-甲基、C3-C4-烯基亚磺酰基-甲基、C3-C4-烯基磺酰基-甲基、C3-C4-炔基硫烷基-甲基、C3-C4-炔基亚磺酰基-甲基、C3-C4-炔基磺酰基-甲基、甲磺酰胺基、乙磺酰胺基、1,1-二氧代-1,2-噻唑烷-2-基、1,2,4-噁二唑-3-基、2-吡啶基、取代的2-吡啶基或取代的1,2,4-噁二唑-3-基,其中每一个的取代基是1至3个独立地选自氯和甲基的取代基;或X和Y一起形成到氮的双键,其被甲氧基或乙氧基取代。
7.根据权利要求1、3、4和5中任一项所述的化合物,其中,q1和q2各自是1。
8.根据权利要求1、3、4、5和7中任一项所述的化合物,其中,Q是式IIb,其中A是氰基、C1-C3-氰基烷基、C1-C3-卤代烷基、C2-C3-卤代烯基、C1-C3-烷氧基-C1-C3-烷基、C1-C3-烷氧基羰基、C1-C3-烷基硫烷基-C1-C3-烷基、C1-C3-烷基亚磺酰基-C1-C3-烷基、RiSO2、或被1至3个独立地选自氟和氯的取代基取代的6元单环杂芳基。
9.一种组合物,其包含如权利要求1至8中任一项中所定义的化合物、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。
10.一种方法,其为
(i)用于对抗和控制昆虫、螨、线虫或软体动物的方法,所述方法包括向有害生物、有害生物的场所、或易受有害生物攻击的植物施用杀昆虫、杀螨、杀线虫或杀软体动物有效量的如权利要求1至8中任一项中所定义的化合物或如权利要求9中所定义的组合物;或者
(ii)用于保护植物繁殖材料免受昆虫、螨、线虫或软体动物的攻击的方法,所述方法包括用有效量的如权利要求1至8中任一项中所定义的化合物或如权利要求9中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;或者
(iii)用于控制有需要的动物体内或体表的寄生虫的方法,所述方法包括给予有效量的如权利要求1至8中任一项中所定义的化合物或如权利要求9中所定义的组合物。
11.一种植物繁殖材料,如种子,所述植物繁殖材料包含如权利要求1至8中任一项中所定义的化合物或如权利要求9中所定义的组合物、或用所述化合物或所述组合物进行处理、或其上附着有所述化合物或所述组合物。
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