CN102066368A - 用于防治动物害虫的1,2-苯并异噻唑化合物 - Google Patents
用于防治动物害虫的1,2-苯并异噻唑化合物 Download PDFInfo
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- CN102066368A CN102066368A CN2009801232107A CN200980123210A CN102066368A CN 102066368 A CN102066368 A CN 102066368A CN 2009801232107 A CN2009801232107 A CN 2009801232107A CN 200980123210 A CN200980123210 A CN 200980123210A CN 102066368 A CN102066368 A CN 102066368A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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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
- A01N43/80—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/001—Processes for the treatment of water whereby the filtration technique is of importance
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2209/00—Controlling or monitoring parameters in water treatment
- C02F2209/03—Pressure
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2303/00—Specific treatment goals
- C02F2303/16—Regeneration of sorbents, filters
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Abstract
本发明涉及根据权利要求1的式(I)磺酰胺化合物及其N-氧化物和盐。这些化合物可用于对抗动物害虫。本发明还涉及一种制备这些化合物的方法以及用于所述方法的中间体化合物。本发明进一步涉及一种通过使用式(I)化合物、其N-氧化物或盐防治动物害虫的方法,包含所述化合物、其N-氧化物或盐的植物繁殖材料以及农用和兽用组合物。
Description
本发明涉及可用于防治动物害虫的磺酰胺化合物以及涉及制备那些化合物的方法以及用于该方法的前体化合物。本发明进一步涉及一种通过使用这些化合物防治动物害虫的方法,包含所述化合物的植物繁殖材料以及农用和兽用组合物。
发明背景
动物害虫,尤其是无脊椎动物害虫,如节肢动物和线虫以及啮齿动物害虫破坏生长或收获作物并侵袭木质住所和商业结构,导致食品供应和财产的大量经济损失。尽管大量农药试剂是已知的,由于目标害虫对所述试剂产生抗性的能力,持续需要新的用于对抗动物害虫的试剂。
因此,本发明的目的是提供对大量不同的动物害虫,尤其是对难以防治的节肢动物害虫如昆虫或蜘蛛和线虫以及啮齿动物害虫具有良好杀虫活性并显示宽活性谱的化合物。由于它们特定的捕食和社会行为,有效的杀鼠剂应该在致死浓度下美味且具有延迟的毒性作用。
WO 2006/097489描述了式(A)的联苯磺酰胺及其在防治植物病原性有害真菌和有害节肢动物中的用途。
其中RI例如为H、烷基、烷氧基、链烯基、炔基或苄基、RII-RV例如为H、卤素、烷基、卤代甲基、烷氧基或卤代甲氧基,x为0、1、2、3或4,y为0、1、2、3、4或5以及RV和RVII例如为H、卤素、羟基、氰基、烷基、卤代烷基、烷氧基、卤代烷氧基等。
WO 2008/031824描述了式(B)的联苯-4-基磺酰胺及其在防治节肢动物害虫和线虫中的用途:
其中x为1或2,y为0、1、2、3、4或5,RI和RII例如为卤素、羟基、氰基、氨基、硝基、烷基、链烯基、炔基、环烷基、环烷基烷基、烷氧基、链烯氧基、炔氧基、烷氧基烷氧基、环烷基烷氧基、C(OH)(CF3)2、卤代烷基、卤代链烯基、卤代烷氧基、卤代链烯氧基、烷硫基、卤代烷硫基、烷基亚磺酰基、卤代烷基亚磺酰基、烷基磺酰基、卤代烷基磺酰基等以及RIII-RVI例如为氢、卤素、羟基、氰基、氨基、硝基、烷基、烷氧基、卤代烷基、卤代烷氧基、烷硫基、卤代烷硫基、烷基亚磺酰基、卤代烷基亚磺酰基、烷基磺酰基、卤代烷基磺酰基等。
发明描述
本发明的目的是提供对大量不同的动物害虫,尤其是对难以防治的节肢动物害虫如昆虫或蜘蛛具有良好的农药活性,尤其是杀虫活性并显示宽活性谱的化合物。
本发明的另一目的是提供对啮齿动物和其他脊椎动物害虫具有良好杀虫活性的化合物。
令人惊讶的是,已经发现这些和其他目的通过式(I)的磺酰胺化合物及其N-氧化物和盐实现:
其中
R1选自氢、卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-C7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6烷硫基、C2-C6链烯硫基、C2-C6炔硫基、C1-C6卤代烷基和C1-C6卤代烷氧基;
R2和R3独立地选自氢、卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-C7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6烷硫基、C2-C6链烯硫基、C2-C6炔硫基、C1-C6卤代烷基和C1-C6卤代烷氧基;或
R2与R3以及与连接它们的碳原子一起形成稠合的5或6元碳环或稠合的5或6元杂环,该杂环含有1或2个选自O、N和S的杂原子作为环成员,其中各稠合的碳环或杂环未被取代或带有1、2、3或4个相互独立地选自如下的取代基:卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-C7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6烷硫基、C2-C6链烯硫基、C2-C6炔硫基、C1-C6卤代烷基和C1-C6卤代烷氧基;
R4选自卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6卤代烷硫基、C1-C6卤代烷基亚磺酰基和C1-C6卤代烷基磺酰基;
n为0、1、2或3;
R5选自苯基和5或6元杂环Het,其含有1、2或3个选自O、N和S的杂原子作为环成员,其中苯基和Het未被取代或带有1、2、3或4个相互独立地选自如下的取代基:卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6卤代烷硫基、C1-C6卤代烷基亚磺酰基和C1-C6卤代烷基磺酰基;
X为O或NRx,其中Rx选自氢、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6烷基羰基和C1-C6烷基羰氧基;
Y为N或C(Ry),其中Ry选自氢、卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6烷硫基、C2-C6链烯硫基、C2-C6炔硫基、C1-C6卤代烷基和C1-C6卤代烷氧基;和
Z为化学键、O或N(Rz),其中Rz选自C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C1-C6烷氧基、C2-C6链烯氧基、C1-C6烷基羰基和C1-C6烷基羰氧基。
因此,本发明涉及式(I)的磺酰胺化合物及其N-氧化物和盐。
本发明化合物,即式I化合物,其盐,I的N-氧化物以及N-氧化物的盐对无脊椎动物害虫,尤其是对节肢动物害虫,特别是对昆虫害虫具有良好的杀虫活性,并且对大量不同的动物害虫,特别是对难以防治的节肢动物害虫,如昆虫或蜘蛛显示宽活性谱。本发明化合物对某些脊椎动物害虫,尤其是对啮齿动物显示延迟的毒性作用,这使得它们适用于防治啮齿动物和其他脊椎动物害虫。
本发明还涉及一种制备式(I)的磺酰胺化合物的方法,该方法包括使式(II)的化合物与式R5-(Z)-B(ORb1)(ORb2)的有机硼酸(boronic acid)衍生物在碱和过渡金属催化剂存在下反应得到式(I)的磺酰胺化合物:
其中R1、R2、R3、R4、R5、X、Y、Z和n如权利要求1-15中任一项对式(I)化合物所定义,以及其中L1为合适的离去基团和Rb1和Rb2各自独立地为氢或C1-C4烷基,或Rb1和Rb2一起形成1,2-亚乙基结构部分,其碳原子可未被取代或可全部或部分被甲基取代。
式(II)的磺酰胺化合物是新的并且可用作制备本发明式(I)磺酰胺化合物的中间体:
其中R1、R2、R3、R4、n、X和Y具有本文对式(I)化合物所定义的含义之一以及其中L1为卤素。因此,本发明进一步涉及如本文所定义的式(II)化合物。
本发明进一步涉及一种组合物,尤其是农用或兽用组合物或诱饵组合物,其含有至少一种如本文所定义的式(I)的磺酰胺化合物、其N-氧化物和/或其盐,和至少一种液体或固体载体。
本发明进一步涉及一种防治动物害虫的方法,该方法包括用杀虫有效量的式(I)磺酰胺化合物或用杀虫有效量的含有至少一种如本文所定义的式(I)磺酰胺化合物的农业组合物处理害虫、其食物源、其栖息地或其繁殖地,或害虫生长或可生长的植物、种子、土壤、区域、材料或环境,或需防止害虫侵袭或侵染的材料、植物、种子、土壤、表面或空间。
本发明的另一方面涉及一种保护植物繁殖材料和/或由其长出的植物的方法,该方法包括用杀虫有效量的本发明式(I)化合物或其可农用盐或N-氧化物处理植物繁殖材料。
本发明的另一方面涉及包含至少一种本发明式(I)化合物和/或其可农用盐或N-氧化物的植物繁殖材料。
本发明进一步涉及一种处理或保护动物,如哺乳动物、鸟或鱼防止寄生虫侵袭或侵染的方法,该方法包括使动物与杀寄生虫有效量的如本文所定义的式(I)磺酰胺化合物或其可兽用盐或N-氧化物接触。使动物与式(I)化合物、其盐或本发明的兽用组合物接触是指施加或给药于动物。
本发明进一步涉及如本文所定义的式(I)磺酰胺化合物或其可兽用盐或N-氧化物在防治动物害虫中的用途。
发明详述
与式(I)化合物的骨架连接的基团可含有一个或多个手性中心。此时,取决于取代基,式(I)化合物以不同的对映异构体或非对映异构体的形式存在。本发明涉及式(I)化合物的每个可能的立体异构体,即单个对映异构体或非对映异构体,及其混合物。
本发明化合物可以为无定型或可以一种或多种不同的结晶态(多晶形物)存在,其可具有不同的宏观性能,如稳定性或显示不同的生物性能,如活性。本发明包括无定型和结晶的式I化合物,各化合物I的不同结晶态的混合物,及其无定型或结晶盐。
用于本文的术语“动物害虫”包括动物群体,尤其是无脊椎动物害虫,如昆虫、蜘蛛和线虫的群体。这些害虫可侵袭植物,由此造成被侵袭植物的显著损害。用于本文的术语“动物害虫”包括可寄生于动物,如哺乳动物、鸟或鱼由此对被侵袭的动物造成显著损害的体外寄生虫。用于本文的术语“动物害虫”还包括啮齿动物群体,其可侵袭植物或植物繁殖材料,由此造成被侵袭植物的显著损害或它们为疾病载体。
化合物(I)的可农用盐尤其包括其阳离子和阴离子分别对化合物(I)的杀虫作用没有不利影响的那些阳离子的盐或那些酸的酸加成盐。因此,合适的阳离子尤其是碱金属的离子,优选钠和钾,碱土金属的离子,优选钙、镁和钡离子,以及过渡金属的离子,优选锰、铜、锌和铁离子,以及铵离子,需要的话其可带有1-4个C1-C4烷基、羟基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基或羟基-C1-C4烷氧基-C1-C4烷基取代基和/或一个苯基或苄基取代基,实例包括铵、甲基铵、异丙基铵、二异丙基铵、四甲基铵、四乙基铵、四丁基铵、2-羟乙基铵、2-(2-羟基乙氧基)乙-1-基铵(二甘醇胺盐)、二(2-羟基乙-1-基)铵(二乙醇胺盐)、三((2-羟基乙-1-基)铵(三乙醇胺盐)、三(3-丙醇)铵、三甲基苄基铵和三乙基苄基铵,此外还有离子、锍离子,优选三(C1-C4烷基)锍和氧化锍离子,优选三(C1-C4烷基)氧化锍。
有用酸加成盐的阴离子主要是氯离子、溴离子、氟离子、硫酸氢根、硫酸根、磷酸二氢根、磷酸氢根、磷酸根、硝酸根、碳酸氢根、碳酸根、六氟硅酸根、六氟磷酸根、苯甲酸根和C1-C4链烷酸的阴离子,优选甲酸根、乙酸根、丙酸根和丁酸根。它们可以通过使式(I)化合物与对应阴离子的酸,优选盐酸、氢溴酸、硫酸、磷酸或硝酸反应而形成。
式(I)化合物的可兽用盐尤其包括本领域已知和接受用于形成兽用用途的盐的那些阳离子的盐或酸加成盐。例如由含碱性氮原子如氨基的式(I)化合物形成的适合酸加成盐包括与无机酸的盐,例如盐酸盐、硫酸盐、磷酸盐和硝酸盐,和有机酸如乙酸、马来酸的盐,以及如马来酸、二马来酸、富马酸的单酸盐或二酸盐,以及如富马酸、二富马酸、甲烷次磺酸、甲烷磺酸和琥珀酸的单酸盐或二酸盐。
在以上给出的变量定义中,使用通常表示所述取代基的集合性术语。术语Cx-Cy在每种情况下表示所述取代基或取代基结构部分中的可能碳原子数。
用于本文的术语“卤素”指氟、氯、溴和碘。
用于本文的和C1-C6烷氧基、C1-C6烷基羰基、C1-C6烷基羰氧基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6烷硫基的烷基结构部分中的术语″C1-C6烷基″是指具有1-6个碳原子的直链或支化饱和烃基,如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、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、1-乙基-2-甲基丙基等。
因此,用于本文的″C1-C6烷氧基″和″C1-C6烷硫基″是指分别经由氧原子或硫原子在烷基的任意位置连接的具有1-6个碳原子的直链或支化烷基(如上所述)。实例包括甲氧基、乙氧基、丙氧基、异丙氧基、甲硫基、乙硫基、丙硫基、异丙硫基、正丁硫基等。
因此,″C1-C6烷基亚磺酰基″和″C1-C6烷基磺酰基″是指分别经由-S(=O)-结构部分或-S(=O)2-结构部分在烷基的任意位置连接的具有1-6个碳原子的直链或支化烷基(如上所述)。实例包括甲基亚磺酰基、甲基磺酰基等。
因此,″C1-C6烷基羰基″和″C1-C6烷基羰氧基″是指分别经由-C(=O)-结构部分或-C(=O)O-结构部分在烷基的任意位置连接的具有1-6个碳原子的直链或支化烷基(如上所述)。实例包括乙酰基、乙酰氧基等。
用于本文和C1-C6卤代烷氧基、C1-C6卤代烷硫基、C1-C6卤代烷基亚磺酰基和C1-C6卤代烷基磺酰基的卤代烷基结构部分中的术语″C1-C6卤代烷基″是指具有1-6个碳原子的直链或支化烷基(如上所述),其中这些基团中的一些或全部氢原子可被上述卤原子替换,例如氯甲基、溴甲基、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、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、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、CH2-C2F5、CF2-C2F5、CF(CF3)2、1-(氟甲基)-2-氟乙基、1-(氯甲基)-2-氯乙基、1-(溴甲基)-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基、九氟丁基、5-氟-1-戊基、5-氯-1-戊基、5-溴-1-戊基、5-碘-1-戊基、5,5,5-三氯-1-戊基、十一氟戊基、6-氟-1-己基、6-氯-1-己基、6-溴-1-己基、6-碘-1-己基、6,6,6-三氯-1-己基、十二氟己基等。
因此,用于本文的″C1-C6卤代烷氧基″和″C1-C6卤代烷硫基″是指分别经由氧原子或硫原子在烷基的任意位置连接的具有1-6个碳原子的直链或支化卤代烷基(如上所述)。实例包括氯甲氧基、溴甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、二氯氟甲氧基、氯二氟甲氧基、氯甲硫基、溴甲硫基、二氯甲硫基、三氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、氯氟甲硫基、二氯氟甲硫基、氯二氟甲硫基等。
因此,″C1-C6卤代烷基亚磺酰基″和″C1-C6卤代烷基磺酰基″是指分别经由-S(=O)-结构部分或-S(=O)2-结构部分在烷基的任意位置连接的具有1-6个碳原子的直链或支化卤代烷基(如上所述)。实例包括氯甲基亚磺酰基、溴甲基亚磺酰基、二氯甲基亚磺酰基、三氯甲基亚磺酰基、氟甲基亚磺酰基、二氟甲基亚磺酰基、三氟甲基亚磺酰基、氯氟甲基亚磺酰基、二氯氟甲基亚磺酰基、氯二氟甲基亚磺酰基、氯甲基磺酰基、溴甲基磺酰基、二氯甲基磺酰基、三氯甲基磺酰基、氟甲基磺酰基、二氟甲基磺酰基、三氟甲基磺酰基、氯氟甲基磺酰基、二氯氟甲基磺酰基、氯二氟甲基磺酰基等。
用于本文和C2-C6链烯氧基和C2-C6链烯硫基的链烯基结构部分中的术语″C2-C6链烯基″是指具有2-6个碳原子和任意位置的双键的支化或未支化不饱和烃基,如乙烯基、1-丙烯基、2-丙烯基、1-甲基-乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基;1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基、1-乙基-2-甲基-2-丙烯基等。
因此,用于本文的″C2-C6链烯氧基″和″C2-C6链烯硫基″是指分别经由氧原子或硫原子在烃基的任意位置连接的具有2-6个碳原子的直链或支化链烯基(如上所述)。实例包括乙烯氧基、乙烯硫基等。
用于本文和C2-C6炔氧基和C2-C6炔硫基的炔基结构部分中的术语″C2-C6炔基″是指具有2-6个碳原子和含有至少一个叁键的支化或未支化的不饱和烃基,如乙炔基、丙炔基、1-丁炔基、2-丁炔基等。
因此,用于本文的″C2-C6炔氧基″和″C2-C6炔硫基″是指分别经由氧原子或硫原子在烃基的任意位置连接的具有2-6个碳原子的直链或支化炔基(如上所述)。实例包括乙炔氧基、乙炔硫基等。
用于本文和C3-C7环烷基-C1-C4烷基的环烷基结构部分中的术语″C3-C7环烷基″是指单环3-7元饱和碳原子环,如环丙基、环丁基、环戊基、环己基或环庚基。
用于本文的术语″C3-C7环烷基-C1-C4烷基″是指具有1-4个碳原子的烷基(如上所述),其中烷基中的一个氢原子被C3-C7环烷基替换。
用于本文的术语″5或6元杂环″是指具有5或6个环成员和1、2、3或4,优选1、2或3个杂原子作为环成员的饱和或部分不饱和杂环基(“饱和或部分不饱和杂环”)以及指具有5或6个环成员的单环杂芳基,其可稠合至5、6或7元碳环或杂环,因此具有8-10个环原子总数,其中在每种情况下1、2、3或4,优选1、2或3个这些环成员为相互独立地选自O、N和S的杂原子(杂芳基)。杂环基可经由碳环成员或经由氮环成员与分子的剩余部分连接。
饱和或部分不饱和杂环的实例包括吡咯烷基、吡唑啉基、咪唑啉基、吡咯啉基、吡唑啉基、咪唑啉基、四氢呋喃基、二氢呋喃基、1,3-二氧戊环基、二氧戊环烯基(dioxolenyl)、硫杂戊环基(thiolanyl)、二氢噻吩基、唑烷基、异唑烷基、唑啉基、异唑啉基、噻唑啉基、异噻唑啉基、噻唑烷基、异噻唑烷基、氧硫杂戊环基(oxathiolanyl)、哌啶基、哌嗪基、吡喃基、二氢吡喃基、四氢吡喃基、1,3-和1,4-二烷基、噻喃基、二氢噻喃基、四氢噻喃基、吗啉基、噻嗪基等。
用于本文的术语“稠合5或6元碳环或杂环”是指如上所定义的具有5或6个环成员的部分不饱和或芳族碳环或杂环基,其与它稠合的环状基团共享环成员之间的至少一个键,如苯与吡啶稠合为喹啉,苯与嘧啶稠合为喹唑啉,吡啶与吡啶稠合为二氮杂萘,呋喃与吡啶稠合为呋喃并吡啶(furopyridine),二氢呋喃与吡啶稠合为二氢呋喃并吡啶,噻吩与吡啶稠合为噻吩并吡啶,二氢噻吩与吡啶稠合为二氢噻吩并吡啶。
用于本文的术语“植物繁殖材料”包括所有植物生殖部分如种子,和生长植物材料如伐条和块茎(例如马铃薯)等,其可用于植物增殖。这包括种子、根、果实、块茎、球茎、根茎、枝、芽和其它植物部分。也可包括秧苗和幼小植物,其在发芽或出苗后可从土壤中移植。这些植物繁殖材料也可在种植或移植时或之前用植物保护化合物预防性处理。
术语“植物”包括任何类型的植物,包括“非栽培植物”,由其包括“栽培植物”。
术语“非栽培植物”是指任何野生类型的品种或栽培植物的相关品种或相关属。
用于本文的术语“栽培植物”包括通过育种、诱变或基因工程而修饰的植物。遗传修饰植物为其基因材料已经利用重组DNA技术加以修饰,在天然环境下不能易于由杂交育种、突变或天然重组获得的植物。通常,已将一个或多个基因整合至基因修饰植物的基因材料中,以便改进植物的某些性能。这类遗传修饰也包括但不限于通过糖基化或聚合物加成,如异戊二烯基化、乙酰基化或法呢基化结构部分或PEG结构部分而靶向后转录修饰蛋白质(寡肽或多肽)(例如,如以下文献所公开:Biotechnol Prog.2001年,7月-8月;17(4):720-8.,Protein Eng Des Sel.2004年1月;17(1):57-66,Nat.Protoc.2007;2(5):1225-35.,Curr.Opin.Chem.Biol.2006年10月;10(5):487-91.Epub 2006年8月28.,Biomaterials.2001年3月;22(5):405-17,Bioconjug Chem.2005,1月-2月;16(1):113-21)。
用于本文的术语“栽培植物”包括由于育种或基因工程的常规方法获得对施用特定种类除草剂具有耐受性的植物,这些除草剂例如为:羟基苯基丙酮酸双氧化酶(HPPD)抑制剂;乙酰乳酸合酶(ALS)抑制剂,例如磺酰脲类(例如参见US 6,222,100、WO 01/82685、WO 00/26390、WO 97/41218、WO 98/02526、WO 98/02527、WO 04/106529、WO 05/20673、WO 03/14357、WO 03/13225、WO 03/14356、WO 04/16073)或咪唑啉酮类(例如参见US6,222,100、WO 01/82685、WO 00/26390、WO 97/41218、WO 98/02526、WO 98/02527、WO 04/106529、WO 05/20673、WO 03/14357、WO 03/13225、WO 03/14356、WO 04/16073);烯醇丙酮酰莽草酸-3-磷酸合酶(EPSPS)抑制剂,例如草甘膦(glyphosate)(例如参见WO 92/00377);谷胺酰胺合成酶(GS)抑制剂,例如草铵膦(glufosinate)(例如参见EP-A-0242236、EP-A-242246)或苯腈(oxynil)除草剂。数种栽培植物已经通过常规育种(诱变)方法获得了对除草剂的耐受性,例如夏油菜(summerrape)(卡诺拉(Canola))对咪唑啉酮如咪草啶酸(imazamox)具有耐受性。基因工程方法已用于使诸如大豆、棉花、玉米、甜菜和油菜等栽培植物对除草剂具有耐受性,这类除草剂例如为草甘膦和草铵膦,其中某些可以商品名(草甘膦)和(草铵膦)购得。
用于本文的术语″栽培植物″还包括通过利用重组DNA技术能够合成一种或多种杀虫蛋白的植物,尤其是合成来自细菌属芽孢杆菌(Bacillus)的那些,特别是来自苏云金芽孢杆菌(Bacillus thuringiensis)的杀虫蛋白,例如-内毒素,如CryIA(b)、CryIA(c)、CryIF、CryIF(a2)、CryIIA(b)、CryIIIA、CryIIIB(b1)或Cry9c,植物杀虫蛋白(VIP),如VIP1、VIP2、VIP3或VIP3A;寄生在线虫上细菌,例如发光杆菌属(Photorhabdus spp.),致病杆菌属(Xenorhabdus spp.)的杀虫蛋白;由动物产生的毒素,如蝎毒素、蜘蛛类动物毒素、黄蜂毒素或其它昆虫特异性神经毒素;由真菌产生的毒素,例如链霉菌(Streptomycetes)毒素;植物凝血素(lectin),例如豌豆凝血素或大麦凝血素;凝集素;蛋白酶抑制剂,例如胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯块茎储藏蛋白(patatin)、血清半胱胺酸蛋白酶(cystatin)抑制剂、木瓜蛋白酶抑制剂;核糖体失活蛋白(RIP),例如蓖麻毒蛋白、玉蜀黍RIP、相思豆毒蛋白、丝瓜籽毒蛋白(luffin)、皂草毒蛋白(saporin)或葫芦毒蛋白(bryodin);类固醇代谢酶,如3-羟基类固醇氧化酶、蜕皮类固醇-IDP-糖基转移酶、胆固醇氧化酶、蜕皮激素抑制剂或HMG-CoA还原酶;离子通道阻断剂如钠或钙通道的阻断剂、保幼激素酯酶、利尿激素受体(helicokinin受体);1,2-苯二乙烯合酶、联苄合酶、几丁质酶或葡聚糖酶。在本发明的上下文中,这些杀虫蛋白或毒素应明确地理解为前毒素、杂化蛋白、截短或另外修饰的蛋白。杂化蛋白的特征在于具有蛋白质结构域的新组合(例如参见WO 02/015701)。例如,这些毒素或能够合成这些毒素的遗传修饰植物的其它实例公开于EP-A 374753、WO93/007278、WO 95/34656、EP-A427529、EP-A451878、WO 03/018810和WO 03/052073中。生产这些遗传修饰植物的方法通常是本领域熟练技术人员已知的,且例如描述在上文提及的出版物中。遗传修饰植物所含杀虫蛋白可向产生这些蛋白的植物赋予对来自全部分类学节肢动物种群的害虫的耐受性,尤其对甲虫(鞘翅目)、蝇(双翅目),和蝶和蛾(鳞翅目)以及植物寄生线虫(Nematoda)的耐受性。
用于本文的术语″栽培植物″应理解为还包括下述植物:其通过利用重组DNA技术能够合成一种或多种蛋白以增加这些植物的对细菌、病毒或真菌病原体的抗性或耐受性的植物。这类蛋白的实例为所谓″病原相关蛋白″(PR蛋白,例如参见EP-A 0392225)、植物病害抗性基因(例如土豆栽培品种,其表达对致病疫霉(Phytophthora infestans)起抑制活性的源自墨西哥野生土豆(Solanum bulbocastanum)的抗性基因)或T4-溶菌霉(例如能够合成具有增强的对抗细菌,如梨火疫病病菌(Erwinia amylvora)的抗性的蛋白的土豆栽培品种)。产生这些遗传修饰植物的方法对本领域熟练技术人员是已知的且描述于上文提及的出版物中。
用于本文的术语″栽培植物″应理解为还包括下述植物:其通过利用重组DNA技术能够合成一种或多种蛋白以增加这些植物的生产能力(例如生物质生产、谷物产量、淀粉含量、油含量或蛋白质含量)、对干旱、盐浓度或其它生长限制性环境因素的耐受性或对害虫和真菌、细菌或病毒性病原体的耐受性。
用于本文的术语″栽培植物″应理解为还包括下述植物:其通过利用重组DNA技术包含改变量的物质含量或新物质含量以特定地改善人类或动物营养,例如产生促进健康的长链ω-3脂肪酸或不饱和ω-9脂肪酸的油料作物(例如油菜)。
下文中对式I化合物的变量,本发明用途和方法特征以及本发明组合物的优选实施方案的说明不仅对其自身有效,而且优选对其相互组合有效。
优选如下式(I)磺酰胺化合物,其中R1选自氢、卤素、C1-C6烷基、C3-C7环烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6卤代烷基和C1-C6卤代烷氧基。更优选R1选自氢、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基。R1尤其为氢、甲氧基或甲基,特别是氢或甲基。
进一步优选如下式(I)磺酰胺化合物,其中R2和R3独立地选自氢、卤素、C1-C6烷基、C3-C7环烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6卤代烷基和C1-C6卤代烷氧基。更优选R2和R3独立地选自氢、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基。R2和R3尤其为氢或甲基,特别是氢。
同样优选如下式(I)磺酰胺化合物,其中R2与R3以及与连接它们的碳原子一起形成稠合的5或6元碳环或稠合的5或6元杂环,其含有1个选自O、N和S的杂原子作为环成员,其中各稠合的碳环或杂环未被取代或带有1或2个相互独立地选自如下的取代基:卤素、氰基、C1-C6烷基、C3-C7环烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6卤代烷基和C1-C6卤代烷氧基。更优选此时R2与R3以及与连接它们的碳原子一起形成稠合的二氢呋喃、呋喃、二氢噻吩、噻吩、苯或吡啶,其中各稠合环未被取代或带有1或2个相互独立地选自如下的取代基:C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基。R2与R3以及与连接它们的碳原子一起尤其形成稠合的苯,其未被取代或带有1或2个相互独立地选自如下的取代基:C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基,特别是甲基或甲氧基。
进一步优选如下式(I)磺酰胺化合物,其中Y为C(Ry)和Ry选自氢、卤素、C1-C6烷基、C3-C7环烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6卤代烷基和C1-C6卤代烷氧基。Ry在该实施方案中优选选自氢、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基。Ry尤其为氢。
还优选其中Y为N的式(I)磺酰胺化合物。
进一步优选其中X为O或NH的式(I)磺酰胺化合物。X尤其为O。
如果n不为0,则进一步优选其中R4选自卤素、C1-C4烷基和C1-C4卤代烷基的式(I)磺酰胺化合物。
同样优选其中n为0或1的式(I)磺酰胺化合物。更优选n为0。
进一步优选其中Z为化学键或O的式(I)磺酰胺化合物。Z尤其为化学键。
本发明的一个优选实施方案涉及如下式(I)磺酰胺化合物,其中R5选自未被取代或带有1或2如上所定义的取代基的苯基,其中所述取代基优选相互独立地选自卤素、C1-C4烷基、C3-C7环烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基和C1-C4卤代烷基磺酰基。更优选R5为未被取代或带有1或2个相互独立地选自如下的取代基的苯基:卤素、C1-C4烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基磺酰基、C1-C4卤代烷基、C1-C4卤代烷氧基和C1-C4卤代烷硫基。R5尤其为未被取代或带有1或2个相互独立地选自如下的取代基的苯基:F、Cl、CN、CH3、C2H5、CH(CH3)2、CF3、OCH3、OC2H5、OCHF2、SCH3、SCF3和SO2CH3。
如果R5为带有1个取代基的苯基,则该取代基优选在相对于键接位置的2-位或4位连接。如果R5为带有2个取代基的苯基,则这些取代基优选在相对于键接位置2和4位或2和5位连接。
特别优选其中R5为未被取代或带有1或2个如上所定义的取代基的苯基以及其中Z为化学键的式(I)磺酰胺化合物。
本发明的另一优选实施方案涉及如下式(I)磺酰胺化合物,其中R5选自5或6元杂环Het,其含有1、2或3个选自O、N和S的杂原子作为环成员,其中Het未被取代或带有1或2个如上所定义的取代基,其中取代基优选相互独立地选自卤素、C1-C4烷基、C3-C7环烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基和C1-C4卤代烷基磺酰基。
优选Het选自呋喃基(=呋喃基)、吡咯基、噻吩基(=噻吩基)、唑基、异唑基、吡唑基、咪唑基、噻唑基、异噻唑基、1,2,4-二唑基、1,3,4-二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,3-三唑基、1,2,4-三唑基、吡啶基、吡嗪基、嘧啶基和哒嗪基,其中上述各基团未被取代或带有1或2个如上所定义的取代基,其中取代基优选相互独立地选自卤素、C1-C4烷基、C3-C7环烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基和C1-C4卤代烷基磺酰基。更优选Het选自异唑-3-基、异噻唑-3-基、1,2,4-二唑-3-基、1,2,4-噻二唑-3-基、吡啶-2-基和吡啶-3-基,其中上述各基团未被取代或带有1或2个相互独立地选自如下的取代基:卤素、C1-C4烷基、C3-C7环烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基和C1-C4卤代烷基磺酰基。最优选Het选自吡啶-2-基,其未被取代或在吡啶环的3和/或5位带有1或2个上述取代基。
特别是,Het未被取代或带有1或2相互独立地选自F、Cl、CN、CH3、C2H5、CH(CH3)2、CF3、OCH3、OC2H5、OCHF2、SCH3、SCF3和SO2CH3的取代基。
进一步特别优选R5为如上所定义的Het和其中Z为O的式(I)磺酰胺化合物。
因此,本发明的一个特别优选的实施方案涉及如下式(I)磺酰胺化合物,其中R5选自吡啶-2-基和Z为O,其中吡啶未被取代或带有1或2个如上所定义的取代基,其优选位于吡啶环的3和/或5位,其中取代基如上所定义且优选相互独立地选自卤素、C1-C4烷基、C3-C7环烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基和C1-C4卤代烷基磺酰基,特别是相互独立地选自F、Cl、CN、CH3、C2H5、CH(CH3)2、CF3、OCH3、OC2H5、OCHF2、SCH3、SCF3和SO2CH3。
合适的吡啶或嘧啶结构部分(Py)的实例在下表A中给出:
在式(Py)中,*表示与磺酰胺化合物(I)的剩余部分的键接位置。
表A.
(Py) | R1 | R2 | R3 |
1 | H | H | H |
2 | Cl | H | H |
3 | CH3 | H | H |
4 | C2H5 | H | H |
5 | CH(CH3)2 | H | H |
6 | 环丙基 | H | H |
7 | CF3 | H | H |
8 | OCH3 | H | H |
9 | OCHF2 | H | H |
10 | SCH3 | H | H |
11 | H | Cl | H |
12 | Cl | Cl | H |
13 | CH3 | Cl | H |
14 | C2H5 | Cl | H |
15 | CH(CH3)2 | Cl | H |
16 | 环丙基 | Cl | H |
17 | CF3 | Cl | H |
18 | OCH3 | Cl | H |
19 | OCHF2 | Cl | H |
20 | SCH3 | Cl | H |
21 | H | CH3 | H |
22 | Cl | CH3 | H |
23 | CH3 | CH3 | H |
24 | C2H5 | CH3 | H |
25 | CH(CH3)2 | CH3 | H |
26 | 环丙基 | CH3 | H |
27 | CF3 | CH3 | H |
28 | OCH3 | CH3 | H |
29 | OCHF2 | CH3 | H |
30 | SCH3 | CH3 | H |
31 | H | C2H5 | H |
(Py) | R1 | R2 | R3 |
32 | Cl | C2H5 | H |
33 | CH3 | C2H5 | H |
34 | C2H5 | C2H5 | H |
35 | CH(CH3)2 | C2H5 | H |
36 | 环丙基 | C2H5 | H |
37 | CF3 | C2H5 | H |
38 | OCH3 | C2H5 | H |
39 | OCHF2 | C2H5 | H |
40 | SCH3 | C2H5 | H |
41 | H | CH(CH3)2 | H |
42 | Cl | CH(CH3)2 | H |
43 | CH3 | CH(CH3)2 | H |
44 | C2H5 | CH(CH3)2 | H |
45 | CH(CH3)2 | CH(CH3)2 | H |
46 | 环丙基 | CH(CH3)2 | H |
47 | CF3 | CH(CH3)2 | H |
48 | OCH3 | CH(CH3)2 | H |
49 | OCHF2 | CH(CH3)2 | H |
50 | SCH3 | CH(CH3)2 | H |
51 | H | 环丙基 | H |
52 | Cl | 环丙基 | H |
53 | CH3 | 环丙基 | H |
54 | C2H5 | 环丙基 | H |
55 | CH(CH3)2 | 环丙基 | H |
56 | 环丙基 | 环丙基 | H |
57 | CF3 | 环丙基 | H |
58 | OCH3 | 环丙基 | H |
59 | OCHF2 | 环丙基 | H |
60 | SCH3 | 环丙基 | H |
61 | H | CF3 | H |
62 | Cl | CF3 | H |
(Py) | R1 | R2 | R3 |
63 | CH3 | CF3 | H |
64 | C2H5 | CF3 | H |
65 | CH(CH3)2 | CF3 | H |
66 | 环丙基 | CF3 | H |
67 | CF3 | CF3 | H |
68 | OCH3 | CF3 | H |
69 | OCHF2 | CF3 | H |
70 | SCH3 | CF3 | H |
71 | H | OCH3 | H |
72 | Cl | OCH3 | H |
73 | CH3 | OCH3 | H |
74 | C2H5 | OCH3 | H |
75 | CH(CH3)2 | OCH3 | H |
76 | 环丙基 | OCH3 | H |
77 | CF3 | OCH3 | H |
78 | OCH3 | OCH3 | H |
79 | OCHF2 | OCH3 | H |
80 | SCH3 | OCH3 | H |
81 | H | OCHF2 | H |
82 | Cl | OCHF2 | H |
83 | CH3 | OCHF2 | H |
84 | C2H5 | OCHF2 | H |
85 | CH(CH3)2 | OCHF2 | H |
86 | 环丙基 | OCHF2 | H |
87 | CF3 | OCHF2 | H |
88 | OCH3 | OCHF2 | H |
89 | OCHF2 | OCHF2 | H |
90 | SCH3 | OCHF2 | H |
91 | H | SCH3 | H |
92 | Cl | SCH3 | H |
93 | CH3 | SCH3 | H |
94 | C2H5 | SCH3 | H |
95 | CH(CH3)2 | SCH3 | H |
(Py) | R1 | R2 | R3 |
96 | 环丙基 | SCH3 | H |
97 | CF3 | SCH3 | H |
98 | OCH3 | SCH3 | H |
99 | OCHF2 | SCH3 | H |
100 | SCH3 | SCH3 | H |
101 | H | H | Cl |
102 | Cl | H | Cl |
103 | CH3 | H | Cl |
104 | C2H5 | H | Cl |
105 | CH(CH3)2 | H | Cl |
106 | 环丙基 | H | Cl |
107 | CF3 | H | Cl |
108 | OCH3 | H | Cl |
109 | OCHF2 | H | Cl |
110 | SCH3 | H | Cl |
111 | H | H | CH3 |
112 | Cl | H | CH3 |
113 | CH3 | H | CH3 |
114 | C2H5 | H | CH3 |
115 | CH(CH3)2 | H | CH3 |
116 | 环丙基 | H | CH3 |
117 | CF3 | H | CH3 |
118 | OCH3 | H | CH3 |
119 | OCHF2 | H | CH3 |
120 | SCH3 | H | CH3 |
121 | H | H | C2H5 |
122 | Cl | H | C2H5 |
123 | CH3 | H | C2H5 |
124 | C2H5 | H | C2H5 |
125 | CH(CH3)2 | H | C2H5 |
126 | 环丙基 | H | C2H5 |
127 | CF3 | H | C2H5 |
128 | OCH3 | H | C2H5 |
(Py) | R1 | R2 | R3 |
129 | OCHF2 | H | C2H5 |
130 | SCH3 | H | C2H5 |
131 | H | H | CH(CH3)2 |
132 | Cl | H | CH(CH3)2 |
133 | CH3 | H | CH(CH3)2 |
134 | C2H5 | H | CH(CH3)2 |
135 | CH(CH3)2 | H | CH(CH3)2 |
136 | 环丙基 | H | CH(CH3)2 |
137 | CF3 | H | CH(CH3)2 |
138 | OCH3 | H | CH(CH3)2 |
139 | OCHF2 | H | CH(CH3)2 |
140 | SCH3 | H | CH(CH3)2 |
141 | H | H | 环丙基 |
142 | Cl | H | 环丙基 |
143 | CH3 | H | 环丙基 |
144 | C2H5 | H | 环丙基 |
145 | CH(CH3)2 | H | 环丙基 |
146 | 环丙基 | H | 环丙基 |
147 | CF3 | H | 环丙基 |
148 | OCH3 | H | 环丙基 |
149 | OCHF2 | H | 环丙基 |
150 | SCH3 | H | 环丙基 |
151 | H | H | CF3 |
152 | Cl | H | CF3 |
153 | CH3 | H | CF3 |
154 | C2H5 | H | CF3 |
155 | CH(CH3)2 | H | CF3 |
156 | 环丙基 | H | CF3 |
157 | CF3 | H | CF3 |
158 | OCH3 | H | CF3 |
159 | OCHF2 | H | CF3 |
160 | SCH3 | H | CF3 |
161 | H | H | OCH3 |
(Py) | R1 | R2 | R3 |
162 | Cl | H | OCH3 |
163 | CH3 | H | OCH3 |
164 | C2H5 | H | OCH3 |
165 | CH(CH3)2 | H | OCH3 |
166 | 环丙基 | H | OCH3 |
167 | CF3 | H | OCH3 |
168 | OCH3 | H | OCH3 |
169 | OCHF2 | H | OCH3 |
170 | SCH3 | H | OCH3 |
171 | H | H | OCHF2 |
172 | Cl | H | OCHF2 |
173 | CH3 | H | OCHF2 |
174 | C2H5 | H | OCHF2 |
175 | CH(CH3)2 | H | OCHF2 |
176 | 环丙基 | H | OCHF2 |
177 | CF3 | H | OCHF2 |
178 | OCH3 | H | OCHF2 |
179 | OCHF2 | H | OCHF2 |
180 | SCH3 | H | OCHF2 |
181 | H | H | SCH3 |
182 | Cl | H | SCH3 |
183 | CH3 | H | SCH3 |
184 | C2H5 | H | SCH3 |
185 | CH(CH3)2 | H | SCH3 |
186 | 环丙基 | H | SCH3 |
187 | CF3 | H | SCH3 |
188 | OCH3 | H | SCH3 |
189 | OCHF2 | H | SCH3 |
190 | SCH3 | H | SCH3 |
191 | H | Cl | Cl |
192 | H | CH3 | Cl |
193 | H | C2H5 | Cl |
194 | H | CH(CH3)2 | Cl |
(Py) | R1 | R2 | R3 |
195 | H | 环丙基 | Cl |
196 | H | CF3 | Cl |
197 | H | OCH3 | Cl |
198 | H | OCHF2 | Cl |
199 | H | SCH3 | Cl |
200 | H | Cl | CH3 |
201 | H | CH3 | CH3 |
202 | H | C2H5 | CH3 |
203 | H | CH(CH3)2 | CH3 |
204 | H | 环丙基 | CH3 |
205 | H | CF3 | CH3 |
206 | H | OCH3 | CH3 |
207 | H | OCHF2 | CH3 |
208 | H | SCH3 | CH3 |
209 | H | Cl | C2H5 |
210 | H | CH3 | C2H5 |
211 | H | C2H5 | C2H5 |
212 | H | CH(CH3)2 | C2H5 |
213 | H | 环丙基 | C2H5 |
214 | H | CF3 | C2H5 |
215 | H | OCH3 | C2H5 |
216 | H | OCHF2 | C2H5 |
217 | H | SCH3 | C2H5 |
218 | H | Cl | CH(CH3)2 |
219 | H | CH3 | CH(CH3)2 |
220 | H | C2H5 | CH(CH3)2 |
221 | H | CH(CH3)2 | CH(CH3)2 |
222 | H | 环丙基 | CH(CH3)2 |
223 | H | CF3 | CH(CH3)2 |
224 | H | OCH3 | CH(CH3)2 |
225 | H | OCHF2 | CH(CH3)2 |
226 | H | SCH3 | CH(CH3)2 |
227 | H | Cl | 环丙基 |
(Py) | R1 | R2 | R3 |
228 | H | CH3 | 环丙基 |
229 | H | C2H5 | 环丙基 |
230 | H | CH(CH3)2 | 环丙基 |
231 | H | 环丙基 | 环丙基 |
232 | H | CF3 | 环丙基 |
233 | H | OCH3 | 环丙基 |
234 | H | OCHF2 | 环丙基 |
235 | H | SCH3 | 环丙基 |
236 | H | Cl | CF3 |
237 | H | CH3 | CF3 |
238 | H | C2H5 | CF3 |
239 | H | CH(CH3)2 | CF3 |
240 | H | 环丙基 | CF3 |
241 | H | CF3 | CF3 |
242 | H | OCH3 | CF3 |
243 | H | OCHF2 | CF3 |
244 | H | SCH3 | CF3 |
245 | H | Cl | OCH3 |
246 | H | CH3 | OCH3 |
247 | H | C2H5 | OCH3 |
248 | H | CH(CH3)2 | OCH3 |
249 | H | 环丙基 | OCH3 |
250 | H | CF3 | OCH3 |
251 | H | CF3 | OCH3 |
252 | H | OCH3 | OCH3 |
253 | H | OCHF2 | OCH3 |
254 | H | SCH3 | OCH3 |
255 | H | Cl | OCHF2 |
256 | H | CH3 | OCHF2 |
257 | H | C2H5 | OCHF2 |
258 | H | CH(CH3)2 | OCHF2 |
259 | H | 环丙基 | OCHF2 |
260 | H | CF3 | OCHF2 |
合适的基团R5的实例为式(Ar)的基团:
其中R5a、R5b和R5c具有下表B中所给的含义。在式(Ar)中,*表示与磺酰胺化合物(I)的剩余部分的键接位置。
表B.
Ar | R5a | R5b | R5c |
1 | H | H | H |
2 | F | H | H |
3 | Cl | H | H |
4 | CH3 | H | H |
5 | CF3 | H | H |
6 | H | F | H |
7 | H | Cl | H |
8 | H | CN | H |
9 | H | CH3 | H |
10 | H | C2H5 | H |
11 | H | CH(CH3)2 | H |
Ar | R5a | R5b | R5c |
12 | H | CF3 | H |
13 | H | OCH3 | H |
14 | H | OC2H5 | H |
15 | H | OCHF2 | H |
16 | H | SCH3 | H |
17 | H | SCF3 | H |
18 | H | SO2CH3 | H |
19 | F | F | H |
20 | F | Cl | H |
21 | F | CN | H |
22 | F | CH3 | H |
Ar | R5a | R5b | R5c |
23 | F | C2H5 | H |
24 | F | CH(CH3)2 | H |
25 | F | CF3 | H |
26 | F | OCH3 | H |
27 | F | OC2H5 | H |
28 | F | OCHF2 | H |
29 | F | SCH3 | H |
30 | F | SCF3 | H |
31 | F | SO2CH3 | H |
32 | Cl | F | H |
33 | Cl | Cl | H |
34 | Cl | CN | H |
35 | Cl | CH3 | H |
36 | Cl | C2H5 | H |
37 | Cl | CH(CH3)2 | H |
38 | Cl | CF3 | H |
39 | Cl | OCH3 | H |
40 | Cl | OC2H5 | H |
41 | Cl | OCHF2 | H |
42 | Cl | SCH3 | H |
43 | Cl | SCF3 | H |
44 | Cl | SO2CH3 | H |
45 | CH3 | F | H |
46 | CH3 | Cl | H |
47 | CH3 | CN | H |
48 | CH3 | CH3 | H |
49 | CH3 | C2H5 | H |
50 | CH3 | CH(CH3)2 | H |
51 | CH3 | CF3 | H |
52 | CH3 | OCH3 | H |
53 | CH3 | OC2H5 | H |
54 | CH3 | OCHF2 | H |
55 | CH3 | SCH3 | H |
Ar | R5a | R5b | R5c |
56 | CH3 | SCF3 | H |
57 | CH3 | SO2CH3 | H |
58 | CF3 | F | H |
59 | CF3 | Cl | H |
60 | CF3 | CN | H |
61 | CF3 | CH3 | H |
62 | CF3 | C2H5 | H |
63 | CF3 | CH(CH3)2 | H |
64 | CF3 | CF3 | H |
65 | CF3 | OCH3 | H |
66 | CF3 | OC2H5 | H |
67 | CF3 | OCHF2 | H |
68 | CF3 | SCH3 | H |
69 | CF3 | SCF3 | H |
70 | CF3 | SO2CH3 | H |
71 | F | H | F |
72 | F | H | Cl |
73 | F | H | CN |
74 | F | H | CH3 |
75 | F | H | C2H5 |
76 | F | H | CH(CH3)2 |
77 | F | H | CF3 |
78 | F | H | OCH3 |
79 | F | H | OC2H5 |
80 | F | H | OCHF2 |
81 | F | H | SCH3 |
82 | F | H | SCF3 |
83 | F | H | SO2CH3 |
84 | Cl | H | F |
85 | Cl | H | Cl |
86 | Cl | H | CN |
87 | Cl | H | CH3 |
88 | Cl | H | C2H5 |
Ar | R5a | R5b | R5c |
89 | Cl | H | CH(CH3)2 |
90 | Cl | H | CF3 |
91 | Cl | H | OCH3 |
92 | Cl | H | OC2H5 |
93 | Cl | H | OCHF2 |
94 | Cl | H | SCH3 |
95 | Cl | H | SCF3 |
96 | Cl | H | SO2CH3 |
97 | CH3 | H | F |
98 | CH3 | H | Cl |
99 | CH3 | H | CN |
100 | CH3 | H | CH3 |
101 | CH3 | H | C2H5 |
102 | CH3 | H | CH(CH3)2 |
103 | CH3 | H | CF3 |
104 | CH3 | H | OCH3 |
105 | CH3 | H | OC2H5 |
Ar | R5a | R5b | R5c |
106 | CH3 | H | OCHF2 |
107 | CH3 | H | SCH3 |
108 | CH3 | H | SCF3 |
109 | CH3 | H | SO2CH3 |
110 | CF3 | H | F |
111 | CF3 | H | Cl |
112 | CF3 | H | CN |
113 | CF3 | H | CH3 |
114 | CF3 | H | C2H5 |
115 | CF3 | H | CH(CH3)2 |
116 | CF3 | H | CF3 |
117 | CF3 | H | OCH3 |
118 | CF3 | H | OC2H5 |
119 | CF3 | H | OCHF2 |
120 | CF3 | H | SCH3 |
121 | CF3 | H | SCF3 |
122 | CF3 | H | SO2CH3 |
合适的基团R5的其他实例为下表C中所示的基团Het。
表C
Het | R5 |
1 | 吡啶-2-基 |
2 | 3-氟吡啶-2-基 |
3 | 3-氯吡啶-2-基 |
4 | 3-氰基吡啶-2-基 |
5 | 3-甲基吡啶-2-基 |
6 | 3-乙基吡啶-2-基 |
7 | 3-异丙基吡啶-2-基 |
8 | 3-三氟甲基吡啶-2-基 |
9 | 3-甲氧基吡啶-2-基 |
10 | 3-乙氧基吡啶-2-基 |
11 | 3-二氟甲氧基吡啶-2-基 |
12 | 3-甲硫基吡啶-2-基 |
Het | R5 |
13 | 3-三氟甲硫基吡啶-2-基 |
14 | 3-甲基磺酰基吡啶-2-基 |
15 | 5-氟吡啶-2-基 |
16 | 5-氯吡啶-2-基 |
17 | 5-氰基吡啶-2-基 |
18 | 5-甲基吡啶-2-基 |
19 | 5-乙基吡啶-2-基 |
20 | 5-异丙基吡啶-2-基 |
21 | 5-三氟甲基吡啶-2-基 |
22 | 5-甲氧基吡啶-2-基 |
23 | 5-乙氧基吡啶-2-基 |
24 | 5-二氟甲氧基吡啶-2-基 |
Het | R5 |
25 | 5-甲硫基吡啶-2-基 |
26 | 5-三氟甲硫基吡啶-2-基 |
27 | 5-甲基磺酰基吡啶-2-基 |
28 | 3,5-二氟吡啶-2-基 |
29 | 3-氟-5-氯吡啶-2-基 |
30 | 3-氟-5-氰基吡啶-2-基 |
31 | 3-氟-5-甲基吡啶-2-基 |
32 | 3-氟-5-乙基吡啶-2-基 |
33 | 3-氟-5-异丙基吡啶-2-基 |
34 | 3-氟-5-三氟甲基吡啶-2-基 |
35 | 3-氟-5-甲氧基吡啶-2-基 |
36 | 3-氟-5-乙氧基吡啶-2-基 |
37 | 3-氟-5-二氟甲氧基吡啶-2-基 |
38 | 3-氟-5-甲硫基吡啶-2-基 |
39 | 3-氟-5-三氟甲硫基吡啶-2-基 |
40 | 3-氟-5-甲基磺酰基吡啶-2-基 |
41 | 3-氯-5-氟吡啶-2-基 |
42 | 3,5-二氯吡啶-2-基 |
43 | 3-氯-5-氰基吡啶-2-基 |
44 | 3-氯-5-甲基吡啶-2-基 |
45 | 3-氯-5-乙基吡啶-2-基 |
46 | 3-氯-5-异丙基吡啶-2-基 |
47 | 3-氯-5-三氟甲基吡啶-2-基 |
48 | 3-氯-5-甲氧基吡啶-2-基 |
49 | 3-氯-5-乙氧基吡啶-2-基 |
50 | 3-氯-5-二氟甲氧基吡啶-2-基 |
51 | 3-氯-5-甲硫基吡啶-2-基 |
52 | 3-氯-5-三氟甲硫基吡啶-2-基 |
53 | 3-氯-5-甲基磺酰基吡啶-2-基 |
54 | 3-氰基-5-氟吡啶-2-基 |
55 | 3-氰基-5-氯吡啶-2-基 |
56 | 3,5-二氰基吡啶-2-基 |
Het | R5 |
57 | 3-氰基-5-甲基吡啶-2-基 |
58 | 3-氰基-5-乙基吡啶-2-基 |
59 | 3-氰基-5-异丙基吡啶-2-基 |
60 | 3-氰基-5-三氟甲基吡啶-2-基 |
61 | 3-氰基-5-甲氧基吡啶-2-基 |
62 | 3-氰基-5-乙氧基吡啶-2-基 |
63 | 3-氰基-5-二氟甲氧基吡啶-2-基 |
64 | 3-氰基-5-甲硫基吡啶-2-基 |
65 | 3-氰基-5-三氟甲硫基吡啶-2-基 |
66 | 3-氰基-5-甲基磺酰基吡啶-2-基 |
67 | 3-甲基-5-氟吡啶-2-基 |
68 | 3-甲基-5-氯吡啶-2-基 |
69 | 3-甲基-5-氰基吡啶-2-基 |
70 | 3,5-二甲基吡啶-2-基 |
71 | 3-甲基-5-乙基吡啶-2-基 |
72 | 3-甲基-5-异丙基吡啶-2-基 |
73 | 3-甲基-5-三氟甲基吡啶-2-基 |
74 | 3-甲基-5-甲氧基吡啶-2-基 |
75 | 3-甲基-5-乙氧基吡啶-2-基 |
76 | 3-甲基-5-二氟甲氧基吡啶-2-基 |
77 | 3-甲基-5-甲硫基吡啶-2-基 |
78 | 3-甲基-5-三氟甲硫基吡啶-2-基 |
79 | 3-甲基-5-甲基磺酰基吡啶-2-基 |
80 | 3-乙基-5-氟吡啶-2-基 |
81 | 3-乙基-5-氯吡啶-2-基 |
82 | 3-乙基-5-氰基吡啶-2-基 |
83 | 3-乙基-5-甲基吡啶-2-基 |
84 | 3,5-二乙基吡啶-2-基 |
85 | 3-乙基-5-异丙基吡啶-2-基 |
86 | 3-乙基-5-三氟甲基吡啶-2-基 |
87 | 5-甲氧基吡啶-2-基 |
88 | 5-乙氧基吡啶-2-基 |
对于它们的用途,特别优选汇集在下表中的式(I)磺酰胺化合物。此外,在表中作为取代基提及的基团本身(与其中提及它们的组合无关)为所述取代基的特别优选的实施方案。
本发明的一个特定实施方案涉及如下的式(I)磺酰胺化合物,其中m为0,X为O,Y为CH和Z为化学键,在下文中称作式(I.A)的磺酰胺化合物:
其中R1、R2、R3和R5具有上文所给含义,特别是作为优选提及的那些含义。
表1(化合物(I.A-Ar.1-1)-(I.A-Ar.1-282))
如下式(I.A)化合物,其中R5为表B中第1行所定义的基团(Ar.1)和R1、R2和R3具有对应于表A中任意一行的含义之一。
表2-122(化合物(I.A-Ar.2-1)-(I.A-Ar.122-282))
如下式(I.A)化合物,其中R5为如表B第2-122行所定义的基团(Ar.2)-(Ar.122)之一和R1、R2和R3具有对应于表A中任意一行的含义之一。
表123(化合物(I.A-Het.1-1)-(I.A-Het.1-282))
如下式(I.A)化合物,其中R5为表C中第1行所定义的基团(Het.1)和R1、R2和R3具有对应于表A中任意一行的含义之一。
表124-388(化合物(I.A-Het.2-1)-(I.A-Het.266-282))
如下式(I.A)化合物,其中R5为如表C第2-266行所定义的基团(Het.2)-(Het.266)之一和R1、R2和R3具有对应于表A中任意一行的含义之一。
本发明的另一特定实施方案涉及如下的式(I)磺酰胺化合物,其中m为0,X为O,Y为CH和Z为O,在下文中称作式(I.B)的磺酰胺化合物:
其中R1、R2、R3和R5具有上文所给含义,特别是作为优选提及的那些含义。
表389(化合物(I.B-Ar.1-1)-(I.B-Ar.1-282))
如下式(I.B)化合物,其中R5为表B中第1行所定义的基团(Ar.1)和R1、R2和R3具有对应于表A中任意一行的含义之一。
表390-510(化合物(I.B-Ar.2-1)-(I.B-Ar.122-282))
如下式(I.B)化合物,其中R5为如表B第2-122行所定义的基团(Ar.2)-(Ar.122)之一和R1、R2和R3具有对应于表A中任意一行的含义之一。
表511(化合物(I.B-Het.1-1)-(I.B-Het.1-282))
如下式(I.B)化合物,其中R5为表C中第1行所定义的基团(Het.1)和R1、R2和R3具有对应于表A中任意一行的含义之一。
表512-776(化合物(I.B-Het.2-1)-(I.B-Het.266-282))
如下式(I.B)化合物,其中R5为如表C第2-266行所定义的基团(Het.2)-(Het.266)之一和R1、R2和R3具有对应于表A中任意一行的含义之一。
本发明的另一特定实施方案涉及如下的式(I)磺酰胺化合物,其中m为0,X为O,Y为N和Z为化学键,在下文中称作式(I.C)的磺酰胺化合物:
其中R1、R2、R3和R5具有上文所给含义,特别是作为优选提及的那些含义。
表777(化合物(I.C-Ar.1-1)-(I.C-Ar.1-282))
如下式(I.C)化合物,其中R5为表B中第1行所定义的基团(Ar.1)和R1、R2和R3具有对应于表A中任意一行的含义之一。
表778-898(化合物(I.C-Ar.2-1)-(I.C-Ar.122-282))
如下式(I.C)化合物,其中R5为如表B第2-122行所定义的基团(Ar.2)-(Ar.122)之一和R1、R2和R3具有对应于表A中任意一行的含义之一。
表899(化合物(I.C-Het.1-1)-(I.C-Het.1-282))
如下式(I.C)化合物,其中R5为表C中第1行所定义的基团(Het.1)和R1、R2和R3具有对应于表A中任意一行的含义之一。
表900-1164(化合物(I.C-Het.2-1)-(I.C-Het.266-282))
如下式(I.C)化合物,其中R5为如表C第2-266行所定义的基团(Het.2)-(Het.266)之一和R1、R2和R3具有对应于表A中任意一行的含义之一。
本发明的另一特定实施方案涉及如下的式(I)磺酰胺化合物,其中m为0,X为O,Y为N和Z为O,在下文中称作式(I.D)的磺酰胺化合物:
其中R1、R2、R3和R5具有上文所给含义,特别是作为优选提及的那些含义。
表1165(化合物(I.D-Ar.1-1)-(I.D-Ar.1-282))
如下式(I.D)化合物,其中R5为表B中第1行所定义的基团(Ar.1)和R1、R2和R3具有对应于表A中任意一行的含义之一。
表1166-1286(化合物(I.D-Ar.2-1)-(I.D-Ar.122-282))
如下式(I.D)化合物,其中R5为如表B第2-122行所定义的基团(Ar.2)-(Ar.122)之一和R1、R2和R3具有对应于表A中任意一行的含义之一。
表1287(化合物(I.D-Het.1-1)-(I.D-Het.1-282))
如下式(I.D)化合物,其中R5为表C中第1行所定义的基团(Het.1)和R1、R2和R3具有对应于表A中任意一行的含义之一。
表1288-1552(化合物(I.D-Het.2-1)-(I.D-Het.266-282))
如下式(I.D)化合物,其中R5为如表C第2-266行所定义的基团(Het.2)-(Het.266)之一和R1、R2和R3具有对应于表A中任意一行的含义之一。
本发明的式(I)化合物可通过类似于现有技术本身已知用于制备联苯化合物的方法和本身已知用于制备磺酰亚胺化合物如邻磺酰苯甲酰亚胺衍生物的方法的各种路线制备。有利的是,它们可如方案1-5所述得到。
式(I)磺酰胺化合物通常可通过使式(II)化合物与式R5-(Z)-B(OR1a)(OR1b)的有机硼酸衍生物通过Suzuki偶合如方案1所示制备。
方案1:
在方案1中,R1、R2、R3、R4、R5、X、Y、Z和n如上所定义,Rb1和Rb2各自独立地为氢或C1-C4烷基,或Rb1和Rb2一起形成1,2-亚乙基结构部分,其碳原子可未被取代或可全部或部分被甲基取代,和L1为合适的离去基团。合适的离去基团L1为卤素,优选氯、溴或碘,烷基碳酸根、苯甲酸根、烷基磺酸根、卤代烷基磺酸根或芳基磺酸根,最优选氯或溴。
反应通常在碱和催化剂,尤其是钯催化剂存在下如下述文献所述进行:Synth.Commun.第11卷,第513页,(1981);Acc.Chem.Res.第15卷,第178-184页(1982);Chem.Rev.第95卷,第2457-2483页(1995);OrganicLetters第6卷(16),第2808页(2004);″Metal catalyzed cross couplingreactions(金属催化交叉偶合反应)″,第2版,Wiley,VCH 2005(编辑DeMeijere,Diederich);″Handbook of organopalladium chemistry for organicsynthesis(用于有机合成的有机钯化学手册)″(编辑Negishi),Wiley,Interscience,New York,2002;″Handbook of functionalizedorganometallics(官能化有机金属手册)″,(编辑P.Knochel),Wiley,VCH,2005。
合适的催化剂为四(三苯基膦)钯(O);双(三苯基膦)氯化钯(II);双(乙腈)氯化钯(II);[1,1′-双(二苯基膦基)二茂铁]-钯(II)氯化物/亚甲基氯化物(1∶1)配合物;双[双-(1,2-二苯基膦基)乙烷]钯(O);双(双-(1,2-二苯基膦基)丁烷]-氯化钯(II);乙酸钯(II);氯化钯(II);和乙酸钯(II)/三-邻甲苯基膦配合物或膦与Pd盐的混合物或膦与Pd的配合物,例如二亚苄基丙酮-钯与三叔丁基膦(或其四氟硼酸盐)、三环己基膦;或结合聚合物的Pd-三苯基膦催化剂体系。
合适的碱通常为无机化合物,例如碱金属氧化物和碱土金属氧化物,例如氧化锂、氧化钠、氧化钙和氧化镁;碱金属碳酸盐和碱土金属碳酸盐,例如碳酸锂、碳酸钠、碳酸钾、碳酸铯和碳酸钙;以及碱金属碳酸氢盐,例如碳酸氢钠;碱金属醇盐和碱土金属醇盐,例如甲醇钠、乙醇钠、乙醇钾和叔丁醇钾;还有有机碱,例如叔胺,例如三甲胺、三乙胺、二异丙基乙胺和N-甲基哌啶、吡啶、被取代的吡啶(例如可力丁、卢剔啶和4-二甲基氨基吡啶),以及双环胺。尤其优选诸如碳酸钠、碳酸钾、碳酸铯、三乙胺和碳酸氢钠的碱。
该碱相对于化合物(II)以1∶1-1∶10,优选1∶1.5-1∶5的摩尔比使用,有机硼酸相对于化合物(II)以1∶1-1∶5,优选1∶1-1∶2.5的摩尔比使用。在某些情况下,以相对于化合物(II)为0.7∶1-0.99∶1的亚化学计量的量使用有机硼酸对于易于纯化而言可能是有利的。
反应通常在惰性有机溶剂中进行。合适的溶剂为脂族烃,例如戊烷、己烷、环己烷和石油醚;芳族烃,例如甲苯、邻二甲苯、间二甲苯和对二甲苯;醚,例如二异丙基醚、叔丁基甲醚、二烷、苯甲醚和四氢呋喃和二甲氧基乙烷;酮,例如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮;以及二甲亚砜、二甲基甲酰胺和二甲基乙酰胺;尤其优选醚,例如四氢呋喃、二烷和二甲氧基乙烷。也可使用所提及溶剂的混合物或与水的混合物。
反应通常在20-180℃,优选40-120℃的温度下进行。
反应完成后,可通过使用例如将反应混合物加入水中,用有机溶剂萃取,浓缩萃取物等常规方法来分离式(I)化合物。需要的话,分离的化合物(I)可经由例如层析法、再结晶等技术来纯化。
也可将捕捉剂加入反应混合物中以通过结合副产物或未反应原料和简单过滤来除去那些副产物或未反应原料。对于细节参见″Synthesis andpurification catalog″,Argonaut,2003及其中所引用的文献。
式R5-(Z)-B(OR1a)(OR1b)的有机硼酸或酯可市购或可根据以下文献制备:″Science of Synthesis(合成科学)″,第6卷,Thieme,2005;WO02/042275;Synlett 2003,(8)第1204页;J.Org.Chem.,2003,68,第3729页;Synthesis,2000,第442页;J.Org.Chem.,1995,60,第750页;或″Handbook of functionalized organometallics(官能化有机金属手册)″,(P.Knochel编辑),Wiley,VCH,2005。
其中X为O或NH的化合物(II)可通过式(V)的磺酰胺化合物的分子内环化如方案2所示而得到:
方案2:
在方案2中,L1、R1、R2、R3、R4、Y和n如上所定义,和W为CN或-C(=O)L2,其中L2为离去基团,如卤素或烷氧基,优选C1-C4烷氧基。
磺酰胺(V)环化为其中X为NH的亚氨基邻磺酰苯甲酰亚胺(II)可根据US 5981758中所述的方法进行。反应通常在惰性有机溶剂中在碱存在下进行。合适的溶剂为脂族烃,例如戊烷、己烷、环己烷和石油醚;芳族烃,例如甲苯、邻二甲苯、间二甲苯和对二甲苯;醚,例如二异丙基醚、叔丁基甲醚、二烷、苯甲醚和四氢呋喃和二甲氧基乙烷;酮,例如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮;以及二甲亚砜、二甲基甲酰胺和二甲基乙酰胺。也可使用所提及溶剂的混合物或与水的混合物。优选使用醚,例如四氢呋喃、二烷和二甲氧基乙烷或芳族烃,如甲苯作为与水的混合物。
反应通常在0-80℃,优选10-25℃的温度下进行。
合适的碱通常为无机化合物,例如碱金属氧化物和碱土金属氧化物,例如氧化锂、氧化钠、氧化钙和氧化镁;碱金属碳酸盐和碱土金属碳酸盐,例如碳酸锂、碳酸钠、碳酸钾、碳酸铯和碳酸钙;以及碱金属碳酸氢盐,例如碳酸氢钠;碱金属醇盐和碱土金属醇盐,例如甲醇钠、乙醇钠、乙醇钾和叔丁醇钾;还有有机碱,例如叔胺,例如三甲胺、三乙胺、二异丙基乙胺和N-甲基哌啶、吡啶、被取代的吡啶(例如可力丁、卢剔啶和4-二甲基氨基吡啶),以及双环胺。尤其优选诸如碳酸钠、碳酸钾、碳酸铯、三乙胺和碳酸氢钠的碱。
其中X为NH的式(II)的亚氨基邻磺酰苯甲酰亚胺化合物随后可通过水解(参见制备实施例I.4)转化为其中X为O的式(II)的邻磺酰苯甲酰亚胺化合物或通过与式Rx-LG的烷基化剂或酰化剂反应而转化为其中X为NRx的式(II)的亚氨基邻磺酰苯甲酰亚胺化合物,其中Rx不为氢,其中LG为合适的离去基团,如卤素、烷基磺酸根或芳基磺酸根。
式(II)的亚氨基邻磺酰苯甲酰亚胺的酸水解根据US 5981758中所述的方法进行。可用于水解的酸种类例如但不限于盐酸、氢溴酸、三氟甲磺酸、三氟乙酸、乙酸和甲烷磺酸。合适的溶剂包括水性溶剂和有机溶剂。酸和溶剂的优选组合为含水二烷中的盐酸。
化合物(V)可通过使磺酰氯(III)与氨基化合物(IV)如方案3所示反应而得到。
方案3:
在方案3中,L1、L2、R1、R2、R3、R4、W、Y和n如上所定义,和L3为离去基团,如羟基或卤素,优选氯。
磺酰基化合物(III)与氨基化合物(IV)的反应可根据有机化学的标准方法进行,例如参见Lieb.Ann.Chem.,第641页,1990或WO 2005/033081。
该反应通常在惰性有机溶剂中进行。合适的溶剂为脂族烃,例如戊烷、己烷、环己烷和石油醚;芳族烃,例如甲苯、邻二甲苯、间二甲苯和对二甲苯;卤代烃,如二氯甲烷、氯仿和氯苯,醚,例如乙醚、二异丙基醚、叔丁基甲醚、二烷、苯甲醚和四氢呋喃;腈,如乙腈和丙腈;酮,例如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮;以及二甲亚砜、二甲基甲酰胺和二甲基乙酰胺,优选四氢呋喃、甲基叔丁基醚、二氯甲烷、氯仿、乙腈、甲苯或二甲基甲酰胺。也可使用所提及溶剂的混合物。
可能有利的是在碱存在下进行反应。合适的碱通常为无机化合物,例如碱金属氧化物和碱土金属氢氧化物,例如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙;碱金属氧化物和碱土金属氧化物,例如氧化锂、氧化钠、氧化钙和氧化镁;碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙;碱金属碳酸盐和碱土金属碳酸盐,例如碳酸锂、碳酸钾、和碳酸钙;以及碱金属碳酸氢盐,例如碳酸氢钠;还有有机碱,例如叔胺,例如三甲胺、三乙胺、二异丙基乙胺和N-甲基哌啶、吡啶、被取代的吡啶(例如可力丁、卢剔啶和4-二甲基氨基吡啶),以及双环胺。尤其优选吡啶、三乙基胺和碳酸钾。碱通常以等摩尔量、过量使用,或合适的话用作溶剂。相对于1摩尔化合物(IV),碱通常过量0.5-5摩尔。
反应通常在-30℃至120℃,优选-10℃至100℃的温度下进行。
原料通常以等摩尔量相互反应。
如果磺酰基化合物(III)不可市购,则它们可根据本领域已知的程序得到,例如合适的式(III)化合物可通过磺酰化替换合适的氨基前体的氨基而得到(参见制备实施例I.1.1)。
氨基化合物(IV)由文献已知或可市购,或者它们可由前体(VIa)-(VIc)通过还原制备,其中V如方案4所定义。
方案4:
该还原方法例如可在如下文献中找到或对本领域熟练技术人员是已知的:Houben-Weyl,Band 10/4,Thieme,Stuttgart,1968;Band 11/2,1957;Band E5,1985;J.Heterocycl.Chem.,1997,34(6),第1661-1667页;J.Chem.Soc.1954,第1165页;Heterocycles,41(4),第675-688页,1995;J.Org.Chem.,1982,47,第3153页;Heterocycles,1996,43(9),第1893-1900页;J.Prakt.Chem-Chem.Ztg.336(8),第695-697页,1994。
例如由如下文献所述,肟(VIa)可由相应醛(X=CHO;化合物(VId))或甲基衍生物(X=CH3;化合物(VIe))制备:Houben-Weyl,Band 10/4,Thieme,Stuttgart,1968;Band 11/2,1957;Band E5,1985;J.Prakt.Chem-Chem.Ztg.336(8),第695-697页,1994;Tetrahedron Lett.42(39),第6815-6818页,2001;或Heterocycles,29(9),第1741-1760页,1989。
醛(VId)可市购(例如,吡啶-4-甲醛、喹啉-4-甲醛、2-氯吡啶-4-甲醛)或可以类似于下述文献所述的方法由4-甲基吡啶或4-甲基嘧啶合成:J.Org.Chem.51(4),第536-537页,1986,或如在以下文献中显示,由卤代衍生物(X=卤素,化合物(VIf))合成:Eur.J.Org.Chem.,2003,(8),第1576-1588页;Tetrahedron Lett.1999,40(19),第3719-3722页;Tetrahedron,1999,55(41),第12149-12156页。
甲基衍生物(VIe)可市购(例如,4-甲基吡啶、3-氰基-2,6-二氯-4甲基吡啶、4-甲基喹啉、6-氯-4甲基喹啉、6,8-二甲氧基-喹啉、4-甲基嘧啶、4,6-二甲基嘧啶)或可根据″Science of Synthesis″,第15卷,Thieme,Stuttgart,2005合成。
例如在如下文献中描述,腈(VIb)可在有或无额外催化剂的情况下,由各卤素衍生物(VIf)(V=卤素,优选氯、溴或碘)通过与氰化物源反应来制备:Tetrahedron Lett.42(38),第6707-6710页,2001;Chem.Eur.J.,2003,9(8),第1828-1836页;Chem.Commun.(Cambridge),2004,(12),第1388-1389页;J.Organomet.Chem.2004,689(24),第4576-4583页;或J.Chem.Soc.Perk.T.,1(16),第2323-2326页,1999。或者,如在以下文献中概述,酰胺或肟可脱水成相应的腈(VIb):″Synthesis″,Stuttgart,(10),第943-944页,1992;或其中引用的文献;或Heterocycl.Chem.1997,34(6),第1661-1667页。
4-卤代喹啉(化合物VIf,其中Y为CRy以及R2与R3一起形成稠合苯环)可市购或可根据″Science of Synthesis″,第15卷,Thieme,Stuttgart,2005或例如根据以下文献或其中的引文合成:4-氯-6,7-二甲氧基喹啉:Journal Med.Chem.48(5),第1359页,2005;4-氯-5,7-二氯喹啉:Indian,187817,2002年6月29日;4-氯-7-氯喹啉:Tetrahedron,60(13),第3017页,2004;4-氯-7-三氟甲基喹啉;Tetrahedron lett.,31(8),第1093页,1990;4-氯-7,8-二甲氧基喹啉:Tetrahedron,41(15),第3033页,1985;4-氯-8-甲氧基喹啉:Chem.Berichte 118(4),第1556页,1985;4-氯-(6或7或8)-碘喹啉、4-溴-(6或7或8)-碘喹啉、4-碘-(6或7或8)-碘喹啉:J.Med.Chem.,21(3),第268页,1978。
构建合适的前体或改变取代模式的其它方法可在″Synthesis″,Stuttgart(1),第31-32页,1993;Tetrahedron,1993,49(24),第5315-5326页;″Methods in Science of Synthesis″,Band 15,及其中引用的文献;Bioorg.Med.Chem.Lett.1997,7(23),第2935-2940页;J.Am.Chem.Soc.,1946,68,第1264页;或Org.Synth.1955,III,第272页中找到。
在某些情况下,就易于后处理或纯化而言,在以一锅法(one pot)进行化合物(VI)至化合物(IV)的还原和胺(IV)与化合物(III)的反应而不分离化合物(IV)可能是有利的。
或者,式(I)化合物可如方案5所示通过首先使式(V)化合物与有机硼酸衍生物R5-(Z)-B(ORb1)(ORb2)反应,随后使所得偶合产物(VII)进行分子内环化而得到。
方案5:
该顺序反应的条件对应于之前对Suzuki偶合和分子内环化所述的条件。
在某些情况下,就易于后处理或纯化而言,在以一锅法(one pot)进行化合物(V)与有机硼酸衍生物偶合为化合物(VII),随后使化合物(VII)分子内缩合为化合物(I)而不分离化合物(VII)可能是有利的。
或者,式(I)化合物可如方案6所示通过使式(VIII)的吡啶或嘧啶化合物与式(IX)的邻磺酰苯甲酰亚胺或亚氨基邻磺酰苯甲酰亚胺衍生物反应而得到。
方案6:
在方案6中,R1、R2、R3、R4、R5、X、Y、Z和n如上所定义,和L4为合适的离去基团,如卤素、烷基磺酸根或芳基磺酸根。
如果个别化合物(I)不能通过上述路线得到,则它们可通过将其他化合物(I)衍生化或通过将所述合成路线常规改变而制备。
式(I)化合物的制备可使它们以异构体混合物(立体异构体、对映异构体)得到。需要的话,可将它们通过常用于此的方法,如结晶或色谱法,以及在光学活性吸附物进行拆分得到纯异构体。
N-氧化物可由化合物(I)根据常规氧化方法,如通过用如下物质处理化合物(I)而制备:有机过酸,如间氯过苯甲酸[Journal of MedicinalChemistry,38(11),1892-1903(1995);WO 03/64572],无机氧化剂,如过氧化氢[参见Jounal of Heterocyclic Chemistry,18(7),1305-8(1981)],或过硫酸氢钾制剂,参见Journal of the American Chemical Society,123(25),5962-5973(2001)。
因此,本发明的一个方面涉及一种制备如上所定义的式(I)磺酰胺化合物的方法,其包括使如上所定义的式(II)化合物与式R5-(Z)-B(ORb1)(ORb2)的有机硼酸衍生物在碱和过渡金属催化剂存在下反应得到式(I)磺酰胺化合物。在一个实施方案中,制备式(I)磺酰胺化合物的该方法额外包括,使如上所定义的式(III)磺酰基化合物与如上所定义的式(IV)的氨基化合物在碱存在下反应得到如上所定义的式(V)化合物,随后使式(V)化合物进行分子内环化得到如上所定义的式(II)化合物。
本发明的另一方面涉及一种制备如上所定义的式(I)磺酰胺化合物的方法,其包括使所得化合物(VII)进行分子内环化得到如上所定义的式(I)磺酰胺化合物。在一个实施方案中,制备式(I)磺酰胺化合物的该方法额外包括,使如上所定义的式(V)化合物与如上所定义的式R5-(Z)-B(ORb1)(ORb2)有机硼酸衍生物在碱和过渡金属催化剂存在下反应得到如上所定义的式(VII)的磺酰胺化合物。
本发明的另一方面涉及一种制备如上所定义的式(I)磺酰胺化合物的方法,其包括如方案6所示使式(VIII)的吡啶或嘧啶化合物与式(IX)的邻磺酰苯甲酰亚胺或亚氨基邻磺酰苯甲酰亚胺衍生物反应。
式(II)中间体是新的。因此,本发明的另一方面涉及式(II)的磺酰胺化合物:
其中L1、R1、R2、R3、R4、n、X和Y具有上文对式(I)化合物所定义的含义之一以及其中L1为合适的离去基团,如卤素,优选氯、溴或碘、烷基羧酸根、苯甲酸根、烷基磺酸根、卤代烷基磺酸根或芳基磺酸根。优选L1为卤素,特别是氯或溴。
上文对式(I)化合物变量的优选实施方案所作的说明相应适用于式(II)化合物的变量。
由于式(I)化合物的优异活性,它们可用于防治动物害虫。
因此,本发明还提供了一种防治动物害虫的方法,该方法包括用杀虫有效量的式(I)化合物或其盐或N-氧化物或本文所定义的组合物处理害虫、其食物源、其栖息地或其繁殖地或其中害虫生长或可生长的栽培植物、植物繁殖材料(如种子)、土壤、区域、材料或环境,或需防止害虫侵袭或侵染的材料、栽培植物、植物繁殖材料(如种子)、土壤、表面或空间。
在特定实施方案中,本发明方法用于保护植物繁殖材料(如种子)和由其长出的植物防止动物害虫侵袭或侵染,该方法包括用杀虫有效量的如上所定义的式(I)化合物或其可农用盐或N-氧化物或用杀虫有效量的如上或如下所定义的农业组合物处理植物繁殖材料(如种子)。本发明方法并不限于保护根据本发明处理的“基材”(植物、植物繁殖材料、土壤材料等),且根据所述保护因此对由处理的植物繁殖材料(如种子)长出的植物具有预防作用,其中植物本身未被处理。
在本发明的意义上,“动物害虫”优选选自无脊椎动物害虫,更优选选自节肢动物和线虫,更优选选自有害昆虫、蜘蛛和线虫,甚至更优选选自昆虫。在本发明的另一实施方案中,“动物害虫”选自啮齿动物和其他脊椎动物害虫,但例如不包括人类。
本发明进一步提供了一种用于对抗这类动物害虫的农业组合物,其包含使得具有杀虫活性的量的至少一种式(I)化合物或其至少一种可农用盐或N-氧化物和至少一种惰性液体和/或固体的可农用载体,以及需要的话至少一种表面活性剂。
根据本发明,这类组合物可含有单种本发明式(I)的活性化合物或其盐或N-氧化物或含有数种式(I)化合物或其盐或其N-氧化物的混合物。本发明组合物可包含单个异构体或异构体混合物以及单个互变异构体或互变异构体混合物。
式(I)化合物及其盐和N-氧化物和包含它们的杀虫组合物为防治无脊椎动物害虫,尤其是节肢动物害虫和线虫的有效试剂。由式(I)化合物防治的动物害虫例如包括:
来自鳞翅目的昆虫(鳞翅目(Lepidoptera)),例如小地老虎(Agrotisypsilon)、黄地老虎(Agrotis segetum)、Alabama argillacea、黎豆夜蛾(Anticarsia gemmatalis)、Argyresthia conjugella、Autographa gamma、树尺蠖(Bupalus piniarius)、Cacoecia murinana、Capua reticulana、Cheimatobia brumata、云杉色卷蛾(Choristoneura fumiferana)、Choristoneura occidentalis、Cirphis unipuncta、苹果小卷蛾(Cydiapomonella)、Dendrolimus pini、Diaphania nitidalis、西南玉米杆草螟(Diatraea grandiosella)、埃及钻夜蛾(Earias insulana)、南美玉米苗斑螟(Elasmopalpus lignosellus)、女贞细卷蛾(Eupoecilia ambiguella)、Evetriabouliana、Feltia subterranea、蜡螟(Galleria mellonella)、李小食心虫(Grapholitha funebrana)、梨小食心虫(Grapholitha molesta)、棉铃虫(Heliothis armigera)、烟芽夜蛾(Heliothis virescens)、玉米穗虫(Heliothiszea)、菜螟(Hellula undalis)、Hibernia defoliaria、美国白蛾(Hyphantriacunea)、Hyponomeuta malinellus、番茄虫蛾(Keiferia lycopersicella)、Lambdina fiscellaria、甜菜夜蛾(Laphygma exigua)、咖啡潜叶蛾(Leucoptera coffeella)、旋纹潜蛾(Leucoptera scitella)、Lithocolletisblancardella、葡萄浆果小卷蛾(Lobesia botrana)、甜菜网螟(Loxostegesticticalis)、舞毒蛾(Lymantria dispar)、模毒蛾(Lymantria monacha)、桃潜蛾(Lyonetia clerkella)、黄褐天幕毛虫(Malacosoma neustria)、甘蓝夜蛾(Mamestra brassicae)、Orgyia pseudotsugata、玉米螟(Ostrinia nubilalis)、小眼夜蛾(Panolis flammea)、棉花红铃虫(Pectinophora gossypiella)、疆夜蛾(Peridroma saucia)、圆掌舟蛾(Phalera bucephala)、马铃薯麦蛾(Phthorimaea operculella)、柑桔潜叶蛾(Phyllocnistis citrella)、欧洲粉蝶(Pieris brassicae)、苜蓿绿夜蛾(Plathypena scabra)、菜蛾(Plutellaxylostella)、大豆夜蛾(Pseudoplusia includens)、Rhyacionia frustrana、Scrobipalpula absoluta、麦蛾(Sitotroga cerealella)、葡萄卷叶蛾(Sparganothis pilleriana)、草地夜蛾(Spodoptera frugiperda)、海灰翅夜蛾(Spodoptera littoralis)、斜纹夜蛾(Spodoptera litura)、Thaumatopoeapityocampa、Tortrix viridana、粉纹夜蛾(Trichoplusia ni)和Zeirapheracanadensis;
甲虫(鞘翅目(Coleoptera)),例如梨窄吉丁(Agrilus sinuatus)、直条叩头虫(Agriotes lineatus)、暗色叩头虫(Agriotes obscurus)、Amphimallussolstitialis、Anisandrus dispar、墨西哥棉铃象(Anthonomus grandis)、苹花象(Anthonomus pomorum)、甜菜隐食甲(Atomaria linearis)、纵坑切梢小蠹(Blastophagus piniperda)、Blitophaga undata、蚕豆象(Bruchusrufimanus)、豌豆象(Bruchus pisorum)、欧洲兵豆象(Bruchus lentis)、苹卷象(Byctiscus betulae)、甜菜大龟甲(Cassida nebulosa)、Cerotomatrifurcata、白菜籽龟象(Ceuthorrhynchus assimilis)、芫菁龟象(Ceuthorrhynchus napi)、甜菜胫跳甲(Chaetocnema tibialis)、Conoderusvespertinus、石刁柏负泥虫(Crioceris asp aragi)、长角叶甲(Diabroticalongicornis)、Diabrotica 12-punctata、玉米根叶甲(Diabrotica virgifera)、墨西哥豆瓢虫(Epilachna varivestis)、烟草跳甲(Epitrix hirtipennis)、棉灰蒙象变种(Eutinobothrus brasiliensis)、欧洲松树皮象(Hylobius abietis)、埃及苜蓿叶象(Hypera brunneipennis)、紫苜蓿叶象(Hypera postica)、云杉八齿小蠹(Ips typographus)、烟草负泥虫(Lema bilineata)、黑角负泥虫(Lemamelanopus)、马铃薯叶甲(Leptinotarsa decemlineata)、Limoniuscalifornicus、稻水象甲(Lissorhoptrus oryzophilus)、Melanotus communis、油菜露尾甲(Meligethes aeneus)、大栗鳃金龟(Melolontha hippocastani)、五月鳃金龟(Melolontha melolontha)、水稻负泥虫(Oulema oryzae)、葡萄黑耳喙象(Ortiorrhynchus sulcatus)、草莓根象甲(Otiorrhynchus ovatus)、辣根猿叶甲(Phaedon cochleariae)、Phyllotreta chrysocephala、食叶鳃金龟属(Phyllophaga sp.)、庭园发丽金龟(Phyllopertha horticola)、大豆淡足跳甲(Phyllotreta nemorum)、黄曲条菜跳甲(Phyllotreta striolata)、日本金龟子(Popillia j aponica)、豌豆叶象(Sitona lineatus)和谷象(Sitophilusgranaria),
双翅目昆虫(双翅目(Diptera)),例如埃及伊蚊(Aedes aegypti)、剌扰伊蚊(Aedes vexans)、墨西哥果蝇(Anastrepha ludens)、五斑按蚊(Anophelesmaculipennis)、地中海实蝇(Ceratitis capitata)、蛆症金蝇(Chrysomyabezziana)、Chrysomya hominivorax、Chrysomya macellaria、高粱瘿蚊(Contarinia sorghicola)、嗜人瘤蝇蛆(Cordylobia anthropophaga)、尖音库蚊(Culex pipiens)、瓜蝇(Dacus cucurbitae)、油橄榄实蝇(Dacus oleae)、油菜叶瘿蚊(Dasineura brassicae)、小毛厕蝇(Fannia canicularis)、马蝇(Gasterophilus intestinalis)、刺舌蝇(Glossina morsitans)、Haematobiairritans、Haplodiplosis equestris、花生田灰地种蝇(Hylemyia platura)、纹皮蝇(Hypoderma lineata)、蔬菜斑潜蝇(Liriomyza sativae)、美国潜叶蝇(Liriomyza trifolii)、Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata)、Lycoria pectoralis、麦瘿蚊(Mayetiola destructor)、家蝇(Musca domestica)、厩腐蝇(Muscina stabulans)、羊狂蝇(Oestrus ovis)、欧洲麦秆蝇(Oscinella frit)、天仙子泉蝇(Pegomya hysocyami)、葱蝇(Phorbiaantiqua)、萝卜蝇(Phorbia brassicae)、麦地种蝇(Phorbia coarctata)、樱桃实蝇(Rhagoletis cerasi)、苹果实蝇(Rhagoletis pomonella)、牛虻(Tabanusbovinus)、Tipula oleracea和欧洲大蚊(Tipula paludosa),
蓟马(缨翅目(Thysanoptera)),例如兰花蓟马(Dichromothripscorbetti)、烟褐蓟马(Frankliniella fusca)、苜蓿花蓟马(Frankliniellaoccidentalis)、东方花蓟马(Frankliniella tritici)、桔硬蓟马(Scirtothripscitri)、稻蓟马(Thrips oryzae)、棕榈蓟马(Thrips palmi)和烟蓟马(Thripstabaci),
膜翅目(Hymenoptera),如新疆菜叶蜂(Athalia rosae)、切叶蚁(Attacephalotes)、Atta sexdens、Atta texana、Hoplocampa minuta、Hoplocampatestudinea、小黄家蚁(Monomorium pharaonis)、热带火蚁(Solenopsisgeminate)和红火蚁(Solenopsis invicta);
异翅目(Heteroptera)例如拟绿蝽(Acrosternum hilare)、玉米长蝽(Blissus leucopterus)、黑斑烟盲蝽(Cyrtopeltis notatus)、棉红蝽(Dysdercus cingulatus)、Dysdercus intermedius、麦扁盾蝽(Eurygasterintegriceps)、烟草蝽(Euschistus impictiventris)、棉红铃喙缘蝽(Leptoglossus phyllopus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lygus pratensis)、稻绿蝽(Nezara viridula)、甜菜拟网蝽(Piesmaquadrata)、Solubea insularis和Thyanta perditor;
同翅目(Homopetera),如Acyrthosiphon onobrychis、落叶松球蚜(Adelges laricis)、Aphidula nasturtii、甜菜蚜(Aphis fabae)、草莓根蚜(Aphis forbesi)、苹果蚜(Aphis pomi)、棉蚜(Aphis gossypii)、北美茶簏子蚜(Aphis grossulariae)、希奈德蚜(Aphis schneideri)、卷叶蚜(Aphisspiraecola)、接骨木蚜(Aphis sambuci)、豌豆蚜(Acyrthosiphon pisum)、茄无网蚜(Aulacorthum solani)、银叶粉虱(Bemisia argentifolii)、飞廉短尾蚜(Brachycaudus cardui)、李短尾蚜(Brachycaudus helichrysi)、桃短尾蚜(Brachycaudus persicae)、Brachycaudus prunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorus horni、Cerosipha gossypii、草莓中瘤钉毛蚜(Chaetosiphon fragaefolii)、茶镳隐瘤蚜(Cryptomyzus ribis)、高加索冷杉椎球蚜(Dreyfusia nordmannianae)、云杉椎球蚜(Dreyfusiapiceae)、居根西圆尾蚜(Dysaphis radicola)、Dysaulacorthumpseudosolani、车前圆尾蚜(Dysaphis plantaginea)、梨西圆尾蚜(Dysaphispyri)、蚕豆微叶蝉(Empoasca fabae)、桃大尾蚜(Hyalopterus pruni)、Hyperomyzus lactucae、麦长管蚜(Macrosiphum avenae)、大戟长管蚜(Macrosiphum euphorbiae)、蔷薇管蚜(Macrosiphon rosae)、巢莱修尾蚜(Megoura viciae)、Melanaphis pyrarius、麦无网蚜(Metopolophiumdirhodum)、Myzodes persicae、冬葱瘤额蚜(Myzus ascalonicus)、Myzuscerasi、桃蚜(Myzus persicae)、李瘤蚜(Myzus varians)、黑茶镳子衲长管蚜(Nasonovia ribis-nigri)、稻飞虱(Nilaparvata lugens)、囊柄瘿绵蚜(Pemphigus bursarius)、蔗飞虱(Perkinsiella saccharicida)、忽布疣蚜(Phorodon humuli)、苹木虱(Psylla mali)、梨木虱(Psylla piri)、冬葱瘤蛾蚜(Rhopalomyzus ascalonicus)、玉米蚜(Rhopalosiphum maidis)、禾谷溢管蚜(Rhopalosiphum padi)、苹草缢管蚜(Rhopalosiphum insertum)、Sappaphis mala、Sappaphis mali、麦二叉蚜(Schizaphis graminum)、Schizoneura lanuginosa、麦长管蚜(Sitobion avenae)、Sogatella furcifera、白粉虱(Trialeurodes vaporariorum)、桔二叉蚜(Toxoptera aurantiiand)和葡萄根瘤蚜(Viteus vitifolii);
白蚁(等翅目(Isoptera)),例如Calotermes flavicollis、Leucotermesflavipes、黄肢散白蚁(Reticulitermes flavipes)、欧洲散白蚁(Reticulitermeslucifugus)和Termes natalensis;
直翅目(Orthoptera),例如居屋艾蟋(Acheta domestica)、东方蜚蠊(Blatta orientalis)、德国小蠊(Blattella germanica)、欧洲球螋(Forficulaauricularia)、蝼蛄(Gryllotalpa gryllotalpa)、飞蝗(Locusta migratoria)、双纹黑蝗(Melanoplus bivittatus)、红足黑蝗(Melanoplus femurrubrum)、墨西哥黑蝗(Melanoplus mexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplus spretus)、条纹红蝗(Nomadacris septemfasciata)、美洲大蠊(Periplaneta americana)、美洲沙漠蝗(Schistocerca americana)、Schistocerca peregrina、Stauronotus maroccanus和庭疾灶螽(Tachycinesasynamorus);
蜘蛛纲(Arachnoidea)),如蜘蛛(蜱螨目(Acarina)),例如软蜱科(Argasidae)、硬蜱科(Ixodidae)和疥螨科(Sarcoptidae),如长星形壁虱(Amblyomma americanum)、热带花蜱(Amblyomma variegatum)、波斯锐缘蜱(Argas persicus)、牛壁虱(Boophilus annulatus)、Boophilusdecoloratus、微小牛蜱(Boophilus microplus)、Dermacentor silvarum、Hyalomma truncatum、蓖子硬蜱(Ixodes ricinus)、Ixodes rubicundus、Ornithodorus moubata、Otobius megnini、鸡皮刺螨(Dermanyssusgallinae)、绵羊疥病(Psoroptes ovis)、Rhipicephalus appendiculatus、Rhipicephalus evertsi、人疥螨(Sarcoptes scabiei),瘿螨(Eriophyidae)属,如苹果刺锈螨(Aculus schlechtendali)、Phyllocoptrata oleivora和Eriophyessheldoni;细螨(Tarsonemidae)属,如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemus latus);细须螨(Tenuipalpidae)属,如紫红短须螨(Brevipalpus phoenicis);叶螨(Tetranychidae)属,如朱砂叶螨(Tetranychuscinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychuspacificus)、棉叶螨(Tetranychus telarius)和二点叶螨(Tetranychus urticae),苹果叶螨(Panonychus ulmi)、柑椐叶螨(Panonychus citri)和草地小爪螨(Oligonychus pratensis);
蚤目(Siphonatera),如印鼠客蚤(Xenopsylla cheopsis),角叶蚤属(Ceratophyllus)。
式(I)化合物及其盐和N-氧化物及其组合物也可用于防治线虫,特别是植物寄生线虫如根结线虫,北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogyne javanica)和其他根结线虫属(Meloidogyne);形成胞囊的线虫,马铃薯金线虫(Globoderarostochiensis)和其他球胞囊属(Globodera);禾谷胞囊线虫(Heteroderaavenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heteroderaschachtii)、三叶草胞囊线虫(Heterodera trifolii)和其他胞囊线虫属(Heterodera);种子肿瘿线虫,粒线虫属(Anguina);茎叶线虫,滑刃线虫属(Aphelenchoides);刺线虫,杂草刺线虫(Belonolaimus longicaudatus)和其他针刺线虫属(Belonolaimus);松线虫,松材线虫(Bursaphelenchusxylophilus)和其他伞滑刃线虫属(Bursaphelenchus);环形线虫,环纹线虫属(Criconema)、小环线虫属(Criconemella)、轮线虫属(Criconemoides)、中环线虫属(Mesocriconema);球茎线虫,腐烂茎线虫(Ditylenchusdestructor)、甘薯茎线虫(Ditylenchus dipsaci)和其他茎线虫属(Ditylenchus);锥线虫,锥线虫属(Dolichodorus);螺旋形线虫,Heliocotylenchus multicinctus和其他Helicotylenchus属;鞘线虫和鞘形(sheathoid)线虫,鞘线虫属(Hemicycliophora)和Hemicriconemoides属;Hirshmanniella属;冠线虫,Hoploaimus属;伪根结线虫,珍珠线虫属(Nacobbus);针线虫,Longidorus elongatus和其他长针线虫属(Longidorus);针线虫,针线虫属(Paratylenchus);根腐线虫,疏忽短体线虫(Pratylenchus neglectus)、穿刺根腐线虫(Pratylenchus penetrans)、Pratylenchus curvitatus、古迪短体线虫(Pratylenchus goodeyi)和其他根腐线虫属(Pratylenchus);穿孔线虫,香蕉穿孔线虫(Radopholus similis)和其他穿孔线虫属(Radopholus);肾形线虫,Rotylenchus robustus和其他盘旋线虫属(Rotylenchus);Scutellonema属;残根线虫,Trichodorus primitivus和其他毛刺线虫属(Trichodorus)、拟毛刺属(Paratrichodorus);阻长线虫,克莱顿矮化线虫(Tylenchorhynchus claytoni)、不定矮化线虫(Tylenchorhynchus dubius)和其他矮化线虫属(Tylenchorhynchus);柑桔线虫,垫刃线虫属(Tylenchulus);剑线虫,剑线虫属(Xiphinema);以及其他植物寄生线虫属。
式(I)化合物及其盐和N-氧化物及其组合物也可用于防治除了人类之外的有害脊椎动物,尤其是啮齿动物(啮齿目),包括鼠(Muridae)科,尤其是鼠亚科(Murinae)、仓鼠科(Cricetidae)和河狸鼠科(Myocastoridae)的啮齿动物,特别是家鼠属(Rattus)、小鼠属(Mus)、田鼠属(Microtus)、姬鼠属(Apodemus)、水鼠属(Arvicola)和鼠平属(Clethrionomys)属的啮齿动物,尤其是褐家鼠(Rattus norvegicus)、黑家鼠(Rattus rattus)、Rattusargentiventer、缅鼠(Rattus exulans)、小鼠属(Mus)、水鼠平(Arvicolaterrestris)、普通田鼠(Microtus arvalis)、草原田鼠(Microtuspennsylvanicus)、印度沙鼠(Tatera indica)、白足鼠(Peromyscus leucopus)、鹿鼠(Peromyscus maniculatus)、多乳鼠类(Mastomys natalensis)、刺毛棉鼠(Sigmodon hispidus)、垄鼠(Arvicanthis niloticus)、小板齿鼠(Bandicota bengalensis)、板齿鼠(Bandicota indica)、印度地鼠(Nesokia indica)、Meriones hurrinanae和Millardia meltada。非常特别关注鼠属(Rattus)和小鼠属(Mus)属的代表物,例如优选黑家鼠(Rattus rattus)、褐家鼠(R.norvegicus)、小家属(M.musculus)和海狸鼠(nutria)(Myocastor coypus)。
此外,式(I)化合物及其盐和N-氧化物及其组合物也适用于防治其他人类之外的有害脊椎动物以及害虫,例如负鼠目(didelphimorphia)的脊椎动物害虫,尤其是负鼠科(didelphidae),如负鼠(vulpes vulpes),和美洲负鼠(Didelphidae)、帚尾袋貂属(Trichosurus),尤其是普通刷尾负鼠(Trichosurus vulpecula),兔形目(lagomorpha),尤其是兔科(familyleporidae),如兔(即来自兔亚科的合适的属)和浣熊科(family procyonidae),如浣熊(raccoons),尤其是Procyon Cofor。
本发明因此还涉及一种防治脊椎动物害虫,尤其是啮齿动物害虫的方法,其中在有害脊椎动物的栖息地施加本发明诱饵配制剂。
在本发明的优选实施方案中,式(I)化合物用于防治昆虫或蜘蛛,尤其是鳞翅目(Lepidoptera)、鞘翅目(Coleoptera)、缨翅目(Thysanoptera)和同翅目的昆虫和蜱螨目(Acarina)的蜘蛛。本发明的式(I)的化合物特别可用于防治缨翅目(Thysanoptera)和同翅目的昆虫。
式(I)化合物或包含它们的杀虫组合物可通过使生长的植物/作物与杀虫有效量的式(I)化合物接触而用于保护生长的植物和作物防止动物害虫,尤其是昆虫、螨虫或蜘蛛侵袭或侵染。术语“作物”是指生长和收获的作物两者。
式I或II的化合物可转化为常规配制剂,如溶液、乳液、悬浮液、粉剂、粉末、糊和颗粒。使用形式取决于特定的意欲目的;在每种情况下,应确保本发明化合物精细且均匀的分布。
配制剂以已知方式制备(对于评论例如参见,US 3,060,084、EP-A 707445(对于液体浓缩物),Browning,″Agglomeration(聚集)″,ChemicalEngineering,1967年12月4日,147-48,Perry′s Chemical Engineer′sHandbook,第4版,McGraw-Hill,New York,1963,第8-57页以及下列文献:WO 91/13546、US 4,172,714、US 4,144,050、US 3,920,442、US5,180,587、US 5,232,701、US 5,208,030、GB 2,095,558、US 3,299,566、Klingman,Weed Control as a Science(杂草防治科学),John Wiley andSons,Inc.,New York,1961,Hance等人,Weed Control Handbook(杂草防治手册),第8版,Blackwell Scientific Publications,Oxford,1989和Mollet,H.,Grubemann,A.,Formulation technology,Wiley VCH VerlagGmbH,Weinheim(德国),2001,2.D.A.Knowles,Chemistry andTechnology of Agrochemical Formulations(农业化学配制剂的化学和技术),Kluwer Academic Publishers,Dordrecht,1998(ISBN 0-7515-0443-8)),例如通过将活性化合物与适合农业化学品配制剂的助剂如溶剂(液体载体)和/或固体载体,需要的话乳化剂、表面活性剂和分散剂,防腐剂,消泡剂,防冻剂,以及任选的用于种子处理配制剂和诱饵配制剂的着色剂和/或粘合剂和/或胶凝剂混合而制备。
合适的溶剂的实例为水、芳族溶剂(如产品、二甲苯)、石蜡(如矿物油馏分)、醇类(如甲醇、丁醇、戊醇、苄醇)、酮类(如环己酮、γ-丁内酯)、吡咯烷酮(N-甲基吡咯烷酮(NMP)、N-辛基吡咯烷酮(NOP))、乙酸酯(乙二醇二乙酸酯),二醇、脂肪酸二甲基酰胺、脂肪酸与脂肪酸酯。原则上,还可使用溶剂混合物。
合适的乳化剂尤其为非离子与阴离子乳化剂。
分散剂的实例为木素磺酸盐、木素亚硫酸盐废液,合成聚合物,如聚丙烯酸酯、聚乙烯基吡咯烷酮等,和纤维素衍生物,如甲基纤维素。
适合的表面活性剂包括上述分散剂和乳化剂,如木素磺酸、萘磺酸、苯酚磺酸、二丁基萘磺酸的碱金属盐、碱土金属盐和铵盐,烷基芳基磺酸盐,烷基硫酸盐,烷基磺酸盐,脂肪醇硫酸盐,脂肪酸和硫酸化脂肪醇乙二醇醚,还有磺化萘和萘衍生物与甲醛的缩合物,磺化酚与甲醛的缩合物,萘或萘磺酸与苯酚衍生物和甲醛的缩合物,聚乙氧基化酚,如聚氧乙烯辛基酚醚,乙氧基化异辛基酚,乙氧基化辛基酚,乙氧基化壬基酚,烷基酚聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚(乙氧基化三硬脂基酚),烷基芳基聚醚醇,醇和脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚,乙氧基化聚氧丙烯,月桂醇聚乙二醇醚缩醛,山梨醇酯,木素亚硫酸盐废液和甲基纤维素。
适于制备可直接喷雾溶液、乳液、糊或油分散体的物质为中至高沸点的矿物油馏分如煤油或柴油,还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或它们的衍生物,甲醇,乙醇,丙醇,丁醇,环己醇,环己酮,异佛尔酮,强极性溶剂如二甲亚砜、N-甲基吡咯烷酮和水。
防冻剂如甘油、乙二醇、丙二醇以及杀菌剂也可加入配制剂。
合适的消泡剂例如为基于硅或硬脂酸镁的消泡剂。
合适的防腐剂例如为双氯酚(Dichlorophen)。
种子处理配制剂可额外包含粘合剂与任选的着色剂。
可加入粘合剂以提高处理以后活性材料在种子上的粘附。适合的粘合剂为嵌段共聚物EO/PO表面活性剂,以及聚乙烯醇、聚乙烯基吡咯烷酮、聚丙烯酸酯、聚甲基丙烯酸酯、聚丁烯、聚异丁烯、聚苯乙烯、聚乙烯胺、聚乙烯酰胺、聚乙烯亚胺、聚醚、聚氨酯、聚乙酸乙烯酯、纤基乙酸钠和由这些聚合物衍生的共聚物。
任选在配制剂中也包含着色剂。适用于种子处理配制剂的着色剂或染料为若丹明B、C.I.颜料红112、C.I.溶剂红1、颜料蓝15:4、颜料蓝15:3、颜料蓝15:2、颜料蓝15:1、颜料蓝80、颜料黄1、颜料黄13、颜料红112、颜料红48:2、颜料红48:1、颜料红57:1、颜料红53:1、颜料橙43、颜料橙34、颜料橙5、颜料绿36、颜料绿7、颜料白6、颜料棕25、碱性紫10、碱性紫49、酸性红51、酸性红52、酸性红14、酸性蓝9、酸性黄23、碱性红10、碱性红108。
粉末、撒播用材料和可撒粉产品可以通过将活性物质与固体载体混合或同时研磨而制备。
颗粒如涂敷颗粒、浸渍颗粒和均质颗粒可以通过使活性化合物与固体载体粘附而制备。固体载体实例为矿土如硅胶、硅酸盐、滑石、高岭土、活性粘土(attaclay)、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁、氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵、尿素以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉和其它固体载体。
配制剂通常包含0.01-95重量%,优选0.1-90重量%的活性化合物。此时,活性化合物以90-100%,优选95-100纯度%的纯度(根据NMR谱)使用。
就种子处理而言,所述配制剂可在稀释2-10倍以后,得到即用制剂中活性化合物浓度为0.01-60重量%,优选0.1-40重量%。
式(I)化合物可以直接、以其配制剂形式或由其制备的使用形式,如可直接喷雾溶液、粉末、悬浮液或分散体、乳液、油分散体、糊、可撒粉产品、撒播用材料或颗粒,借助喷雾、雾化、撒粉、撒播或浇灌来使用。使用形式完全取决于意欲的目的;意欲在每种情况下确保本发明活性化合物的最佳可能分布。
含水使用形式可通过加入水由乳液浓缩物、糊或可湿性粉末(可喷雾粉末、油分散体)制备。为制备乳液、糊或油分散体,可借助湿润剂、增粘剂、分散剂或乳化剂将该物质直接或溶于油或溶剂中后在水中均化。然而还可以制备由活性物质、湿润剂、增粘剂、分散剂或乳化剂以及合适的话溶剂或油组成的浓缩物且该浓缩物适于用水稀释。
即用制剂中的活性成分浓度可以在相对宽范围内变化。它们通常为0.0001-10重量%,优选0.01-1重量%。
活性化合物还可极成功地用于超低容量方法(ULV),其中可以施用包含超过95重量%活性化合物的配制剂或甚至可以无添加剂而施用活性化合物。
下列为配制剂实例:
1.用水稀释的用于叶面施用的产品。对于种子处理,这些产品可稀释或不经稀释而施用于种子。
A)水溶性浓缩物(SL、LS)
将10重量份活性化合物溶于90重量份水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解,以此方式得到具有10重量%活性化合物的配制剂。
B)分散性浓缩物(DC)
将20重量份活性化合物溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体,由此得到具有20重量%活性化合物的配制剂。
C)乳油(EC)
将15重量份活性化合物溶于7重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。用水稀释得到乳液,由此得到具有15重量%活性化合物的配制剂。
D)乳液(EW、EO、ES)
将25重量份活性化合物溶于35重量份二甲苯中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。借助乳化机(如Ultraturrax)将该混合物加入30重量份水中并制成均相乳液。用水稀释得到乳液,由此得到具有25重量%活性化合物的配制剂。
E)悬浮液(SC、OD、FS)
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入10重量份分散剂和湿润剂以及70重量份水或有机溶剂,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液,由此得到具有20重量%活性化合物的配制剂。
F)水分散性颗粒和水溶性颗粒(WG、SG)
将50重量份活性化合物细碎研磨并加入50重量份分散剂和湿润剂,借助工业装置(如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性化合物分散体或溶液,由此得到具有50重量%活性化合物的配制剂。
G)水分散性粉末和水溶性粉末(WP、SP、SS、WS)
将75重量份活性化合物在转子-定子磨机中研磨并加入25重量份分散剂、湿润剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液,由此得到具有75重量%活性化合物的配制剂。
H)凝胶配制剂(GF)
在搅拌的球磨机中,将20重量份活性化合物在添加10重量份分散剂,1重量份胶凝剂以及70重量份水或有机溶剂下研磨,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液,由此得到具有20重量%活性化合物的配制剂。
2.不经稀释而叶面施用的产品。对于种子处理,这些产品可经稀释或不经稀释而施用于种子。
I)可撒粉粉末(DP、DS)
将5重量份活性化合物细碎研磨并与95重量份细碎高岭土充分混合。这得到具有5重量%活性化合物的可撒粉产品。
J)颗粒(GR、FG、GG、MG)
将0.5重量份活性化合物细碎研磨并结合99.5重量份载体,由此得到具有0.5重量%活性化合物的配制剂。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而叶面施用的颗粒。
K)ULV溶液(UL)
将10重量份活性化合物溶于90重量份有机溶剂如二甲苯中。这得到不经稀释而叶面施用的具有10重量%活性化合物的产品。
式(I)化合物也适用于处理植物繁殖材料(如种子)。常用的种子处理配制剂例如包括可流动浓缩液FS、溶液LS、干处理用粉末DS、淤浆处理用水分散性粉末WS、水溶性粉末SS和乳液ES与EC以及凝胶配制剂GF。这些配制剂可经稀释或未经稀释而施用于种子。对种子的施用在播种之前,直接对种子或种子预萌发后进行。
在优选实施方案中,将FS配制剂用于种子处理。FS配制剂通常可包含1-800g/l活性成分、1-200g/l表面活性剂、0-200g/l防冻剂、0-400g/l粘合剂、0-200g/l颜料和补充至1升的溶剂,优选水。
用于种子处理的式(I)化合物的其他优选的FS配制剂包含0.1-80重量%的活性成份,0.05-5重量%的润湿剂,0.5-15重量%的分散剂,0.1-5重量%增稠剂,5-20重量%防冻剂,0.1-2重量%消泡剂,1-20重量%的颜料和/或染料,0-15重量%增粘剂/粘合剂,0-75重量%填料/载体,以及0.01-1重量%防腐剂。
可将各种类型的油、湿润剂、辅助剂、除草剂、杀真菌剂、其他农药或杀菌剂加入活性成分中,如果合适的话,恰在紧邻使用前加入(桶混合)。这些试剂与本发明试剂通常以1∶10-10∶1的重量比混合。
式(I)化合物通过接触(经由土壤、玻璃、墙壁、床网、地毯、植物部分或动物部分)和进食(诱饵或植物部分)起作用。
对于用于对抗蚂蚁、白蚁、黄蜂、蝇、蚊、蟋蟀或蟑螂而言,式(I)化合物优选以诱饵组合物使用。
诱饵可以为液体、固体或半固体制剂(例如凝胶)。固体诱饵可形成适于相应施用的各种形状和形式,例如颗粒、块、棒、片。液体诱饵可装入各种装置中以确保正确施用,例如开口容器、喷雾装置、液滴源或蒸发源。凝胶可基于含水或油质基质并且可配制成与粘性、保水性或老化特性相关的特殊需要。
用于组合物中的诱饵是具有足够的吸引力以刺激诸如蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀等的昆虫或蟑螂食用它的产品。该吸引使用进食刺激剂或性信息素进行。合适的食物刺激剂例如但不仅仅选自动物和/或植物蛋白质(肉-、鱼-或血液膳食,昆虫部分、蛋黄)、动物和/或植物来源的脂肪和油或单-、低聚-或聚有机糖类,尤其是蔗糖、乳糖、果糖、右旋糖、葡萄糖、淀粉、果胶或甚至糖蜜或蜂蜜。水果、作物、植物、动物、昆虫的新鲜或腐败部分或其特定部分也可以用作进食刺激剂。已知性信息素更具昆虫特异性。具体信息素描述于文献中并且为本领域技术人员已知的。
作为气溶胶(例如在喷雾罐中)、油喷雾或泵喷雾的式(I)化合物的配制剂高度适于非专业使用者用于防治害虫如蝇、跳蚤、壁虱、蚊或蟑螂。气溶胶配方优选包含活性化合物,溶剂如低级醇(例如甲醇、乙醇、丙醇、丁醇)、酮(例如丙酮、甲基乙基酮),沸点范围为约50-250℃的石蜡烃(例如煤油),二甲基甲酰胺,N-甲基吡咯烷酮,二甲基亚砜,芳族烃如甲苯、二甲苯,水,还有助剂,例如乳化剂如山梨糖醇单油酸酯、具有3-7摩尔氧化乙烯的油基乙氧基化物、脂肪醇乙氧基化物,芳香油如香精油,中脂肪酸与低级醇的酯,芳族羰基化合物,如果合适的话稳定剂如苯甲酸钠,两性表面活性剂,低级环氧化物,原甲酸三乙酯和如果需要的话推进剂如丙烷、丁烷、氮气、压缩空气、二甲醚、二氧化碳、一氧化二氮或这些气体的混合物。
油喷雾配制剂不同于气溶胶配方之处在于不使用推进剂。
式(I)化合物及其各自的组合物也可用于蚊香和熏蒸香、烟盒、蒸发器板或长期蒸发器以及用于粘蛾纸、粘蛾垫或其它基于热的蒸发器系统。
式(I)化合物及其各自的组合物防治由昆虫传播的传染病(例如疟疾、登革热和黄热病、淋巴丝虫病和利什曼病(leishmaniasis))的方法也包括处理房屋表面、空气喷雾和浸渍窗帘、帐篷、衣物、床网、舌蝇捕捉器或类似物。施用于纤维、织物、针织品、非织造物、网状材料或箔片和防水布的杀虫组合物优选包含包括杀虫剂、任选驱除剂和至少一种粘合剂的混合物。合适的驱除剂例如为N,N-二乙基-间-甲基苯甲酰胺(DEET)、N,N-二乙基苯基乙酰胺(DEPA)、1-(3-环己-1-基-羰基)-2-甲基胡椒碱、(2-羟甲基环己基)乙酸内酯、2-乙基-1,3-己二醇、避蚊酮(indalone)、甲基新癸酰胺(MNDA),并非用于昆虫防治的合成除虫菊酯类,如{(+/-)-3-烯丙基-2-甲基-4-氧代环戊-2-(+)烯基-(+)-反式-菊酸酯(Esbiothrin),源自植物萃取物或与其相同的驱除剂,例如苎烯、丁香酚、(+)-优卡马醇(Eucamalol)(1)、(-)-1-表-优卡马醇,或得自植物的粗制植物萃取物,例如柠檬桉(Eucalyptus maculate)、单叶蔓荆、Cymbopogan martinii、柠檬香茅(Cymbopogan citratus)(柠檬草)、Cymopogan nartdus(香茅)。合适的粘合剂例如选自脂族酸的乙烯基酯(如乙酸乙烯酯与支链烷烃羧酸乙烯酯),醇的丙烯酸与甲基丙烯酸酯,如丙烯酸丁酯、丙烯酸2-乙基己酯和丙烯酸甲酯,单-和二烯属不饱和烃类,如苯乙烯,和脂族二烯,如丁二烯的聚合物与共聚物。
窗帘与床网的浸渍通常通过将纺织材料浸没于式(I)活性化合物的乳液或分散体中,或将它们喷雾于网上而进行。
可用于种子处理的方法包括本领域已知的所有合适的种子处理,特别是拌种技术,如种子包衣(如种子造粒)、种子撒粉和种子吸收(如种子浸泡)。此处,“种子处理”是指使种子和式(I)化合物相互接触的所有方法,“拌种”是指向种子提供一定量的式(I)化合物的种子处理方法,即该方法产生包含式(I)化合物的种子。原则上,处理可施用于从种子收获至种子播种的任何时间的种子。种子例如可使用“种植箱”方法紧邻种植种子之前或种植种子的过程中处理。然而,处理也可在种植种子之前数周或数月,例如至多12个月,例如以拌种处理的形式进行处理,而没有观察到效力的显著降低。
有利的是将处理施用于未播种的种子。如本文所用的术语“未播种种子”意味着包括从种子收获到将种子播种到地面以使植物萌发和生长的任何时间中的种子。
具体而言,在处理中,程序如下进行,其中将种子在合适的装置中,例如在用于固体或固体/液体混合伴侣的混合装置中与所需量的种子处理配制剂(直接或在用水预先稀释之后)混合,直至组合物均匀分布在种子上。合适的话,随后进行干燥步骤。
式(I)化合物或其N-氧化物或可兽用盐还特别适用于防治动物体内和身上的寄生虫。
因此,本发明的另一目的为提供在动物体内和身上防治寄生虫的新方法。本发明的另一个目的为提供用于动物的较安全的杀虫剂。本发明的另一个目的进一步提供用于动物的杀虫剂,其可以比现有杀虫剂低的剂量使用。本发明的另一个目的为提供用于动物的杀虫剂,其提供对寄生虫长期残留防治。
本发明还涉及含有杀寄生虫有效量的式(I)化合物或其N-氧化物或可兽用盐和可接受的载体的用于在动物体内和身上对抗寄生虫的组合物。
本发明还提供一种处理、防治、预防或保护动物免受寄生虫侵袭或侵染的方法,其包括将杀寄生虫有效量式(I)化合物或其N-氧化物或可兽用盐或包含它们的组合物口服、局部或肠胃外给药或施用于所述动物。
本发明还提供一种制备用于处理、防治、预防或保护动物免受寄生虫侵袭或侵染的组合物的方法,该组合物包含杀寄生虫有效量的式(I)化合物或其N-氧化物或可兽用盐或包含它们的组合物。
化合物对抗农业害虫的活性并未暗示其对于在动物体内和身上防治体内-与体外寄生虫的适用性,该适用性在口服给药的情况下例如需要低、非致吐剂量,与动物的代谢相容性、低毒性和安全操作。
令人惊讶的是,现在发现式(I)化合物适合在动物体内和身上对抗体内-与体外寄生虫。
式(I)化合物或其N-氧化物或可兽用盐,和包含它们的组合物优选用于在包括温血动物(包括人)在内的动物和鱼中防治和预防侵袭和侵染。它们例如适于在哺乳动物如牛、绵羊、猪、骆驼、鹿、马、小猪、家禽、兔、山羊、狗和猫,水牛、驴、黇鹿和驯鹿,以及产皮动物如貂、灰鼠和浣熊,禽类如母鸡、鹅、火鸡和鸭以及鱼类如淡水鱼和咸水鱼如鲑鱼、鲤鱼和鳗鱼中防治和预防侵袭和侵染。
式(I)化合物或其N-氧化物或可兽用盐和包含它们的组合物优选在家畜如狗或猫中用于防治与预防侵袭和侵染。
在温血动物和鱼类中的侵袭包括但不限于虱、叮咬虱、蜱、鼻蝇、羊蜱蝇(keds)、叮咬蝇、家蝇、蝇、蝇蛆幼虫、恙螨、蚋、蚊子和跳蚤。
式(I)化合物或其N-氧化物或可兽用盐,和包含它们的组合物适于内吸和/或非内吸防治体外和/或体内寄生虫。它们对所有或部分发育阶段有效。
式(I)化合物特别可用于对抗体外寄生虫。
式(I)化合物特别可分别用于对抗下列寄生虫:
跳蚤(蚤目(Siphonaptera)),例如猫跳蚤(Ctenocephalides felis)、狗跳蚤(Ctenocephalides canis)、印鼠客蚤(Xenopsylla cheopis)、致痒蚤(Pulexirritans)、穿皮潜蚤(Tunga penetrans)和具带病蚤(Nosopsyllus fasciatus),
蟑螂(蜚蠊目(Blattaria)-Blattodea),例如德国小蠊(Blattellagermanica)、Blattella asahinae、美洲大蠊(Periplaneta americana)、日本大蠊(Periplaneta japonica)、棕色蜚蠊(Periplaneta brunnea)、Periplanetafuligginosa、澳洲蜚蠊(Periplaneta australasiae)和东方蜚蠊(Blattaorientalis),
蝇、蚊(双翅目(Diptera)),例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedes albopictus)、剌扰伊蚊(Aedes vexans)、墨西哥果蝇(Anastrephaludens)、五斑按蚊(Anopheles maculipennis)、Anopheles crucians、白足按蚊(Anopheles albimanus)、冈比亚按蚊(Anopheles gambiae)、Anophelesfreeborni、海南岛白踝按蚊(Anopheles leucosphyrus)、云南微小按蚊(Anopheles minimus)、四斑按蚊(Anopheles quadrimaculatus)、红头丽蝇(Calliphora vicina)、蛆症金蝇(Chrysomya bezziana)、Chrysomyahominivorax、Chrysomya macellaria、鹿蝇(Chrysops discalis)、Chrysopssilacea、Chrysops atlanticus、螺旋蝇(Cochliomyia hominivorax)、嗜人瘤蝇蛆(Cordylobia anthropophaga)、狂怒库蠓(Culicoides furens)、尖音库蚊(Culex pipiens)、斑蚊(Culex nigripalpus)、致倦库蚊(Culexquinquefasciatus)、媒斑蚊(Culex tarsalis)、Culiseta inornata、Culisetamelanura、Dermatobia hominis、小毛厕蝇(Fannia canicularis)、马蝇(Gasterophilus intestinalis)、刺舌蝇(Glossina morsitans)、须舌蝇(Glossina palpalis)、Glossina fuscipes、胶舌蝇(Glossina tachinoides)、Haematobia irritans、Haplodiplosis equestris、潜蝇属(Hippelates)、纹皮蝇(Hypoderma lineata)、Leptoconops torrens、美国潜叶蝇(Liriomyzatrifolii)、Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Luciliasericata)、Lycoria pectoralis、Mansonia属、家蝇(Musca domestica)、厩腐蝇(Muscina stabulans)、羊狂蝇(Oestrus ovis)、银足白蛉(Phlebotomusargentipes)、Psorophora columbiae、Psorophora discolor、Prosimuliummixtum、赤尾麻蝇(Sarcophaga haemorrhoidalis)、肉蝇属(Sarcophaga)、Simulium vittatum、厩螫蝇(Stomoxys calcitrans)、牛虻(Tab anusbovinus)、Tabanus atratus、红色原虻(Tabanus lineola)和Tabanussimilis,
虱(毛虱目(Phthiraptera)),例如人头虱(Pediculus humanus capitis)、人体虱(Pediculus humanus corporis)、阴虱(Pthirus pubis)、牛血虱(Haematopinus eurysternus)、猪血虱(Haematopinus suis)、牛颚虱(Linognathus vituli)、Bovicola bovis、鸡虱(Menopon gallinae)、Menacanthus stramineus和Solenopotes capillatus,
蜱和寄生螨(寄螨目):蜱科(Ixodidae),如黑脚硬蜱(Ixodes scapularis)、全环硬蜱(Ixodes holocyclus)、太平洋硬蜱(Ixodes pacificus)、Rhipicephalus sanguineus、安氏革蜱(Dermacentor andersoni)、美洲大革蜱(Dermacentor variabilis)、长星形壁虱(Amblyomma americanum)、Ambryomma maculatum、Ornithodorus hermsi、Ornithodorus turicata和寄生螨(Mesostigmata),如柏氏禽刺螨(Ornithonyssus bacoti)和鸡皮刺螨(Dermanyssus gallinae),
辐螨目(Actinedida)(前气门亚目(Prostigmata))和粉螨亚目(Acaridida)(无气门目(Astigmata))如蜂盾螨属(Acarapis)、姬螯螨属(Cheyletiella)、Ornithocheyletia属、鼷鼠肉螨属(Myobia)、Psorergates属、蠕形螨属(Demodex)、恙螨属(Trombicula)、Listrophorus属、粉螨属(Acarus)、食酪螨属(Tyrophagus)、嗜木螨属(Caloglyphus)、Hypodectes属、Pterolichus属、痒螨属(Psoroptes)、足螨属(Chorioptes)、耳痒螨属(Otodectes)、疥螨属(Sarcoptes)、背肛螨属(Notoedres)、膝螨属(Knemidocoptes)、Cytodites属和Laminosioptes属,
臭虫(半翅目(Hemiptera)):温带臭虫(Cimex lectularius)、热带臭虫(Cimex hemipterus)、Reduvius senilis、Triatoma属、猎蝽属(Rhodnius)、锥蝽属(Panstrongylus)和Arilus critatus。
Anoplurida如血虱属(Haematopinus)、颚虱属(Linognathus)、人虱属(Pediculus)、Phtirus属和管虱属(Solenopotes),
食毛目(Mallophagida)(Arnblycerina和Ischnocerina亚目),如Trimenopon属、鸡虱属(Menopon)、鸭虱属(Trinoton)、牛毛虱属属(Bovicola)、Werneckiella属、Lepikentron属、毛虱属(Trichodectes)和猫毛虱属(Felicola),
线虫:
Wipeworms和旋毛虫(Trichinosis)(毛管目(Trichosyringida)),例如毛形线虫科(Trichinellidae(旋毛线虫属(Trichinella)(鞭虫科(Trichuridae))))、鞭虫属(Trichuris)、毛细线虫属(Capillaria),小杆线虫目(Rhabditida),例如小杆线虫属(Rhabditis)、类圆线虫属(Strongyloides)、Helicephalobus属,
圆线虫目(Strongylida),例如圆线虫属(Strongylus)、钩口线虫属(Ancylostoma)、美洲板口线虫(Necator americanus)、仰口线虫属(Bunostomum)(钩虫)、毛圆线虫属(Trichostrongylus)、捻转血矛线虫(Haemonchus contortus.)、奥斯脱线虫属(Ostertagia)、古柏线虫属(Cooperia)、细颈线虫属(Nematodirus)、网尾线虫属(Dictyocaulus)、盅口线虫属(Cyathostoma)、结节线虫属(Oesophagostomum)、有齿肾线虫(Stephanurus dentatus)、盘头线虫属(Ollulanus)、夏伯特线虫属(Chabertia)、有齿肾线虫、气管比翼线虫(Syngamus trachea)、钩口线虫属、钩线虫属(Uncinaria)、球头线虫属(Globocephalus)、板口线虫属(Necator)、后圆线虫属(Metastrongylus)、毛细缪勒线虫(Muelleriuscapillaris)、原圆线虫属(Protostrongylus)、管圆线虫属(Angiostrongylus)、Parelaphostrongylus属、Aleurostrongylus abstrusus和肾膨结线虫(Dioctophyma renale),肠圆线虫(蛔虫目(Ascaridida)),例如似蚓蛔线虫(Ascaris lumbricoides)、猪蛔虫(Ascaris suum)、鸡蛔虫(Ascaridia galli)、马副蛔虫(Parascarisequorum)、蠕形住肠线虫(Enterobius vermicularis(蛲虫))、犬弓首线虫(Toxocara canis)、狮弓蛔虫(Toxascaris leonine)、斯线虫属(Skrjabinema)和马尖尾线虫(Oxyuris equi),驼形线虫目(Camallanida),例如Dracunculus medinensis(麦地那龙线虫),旋尾线虫目(Spirurida),例如吸吮线虫属(Thelazia)、吴策线虫属(Wuchereria)、布鲁线虫属(Brugia)、盘尾丝虫属(Onchocerca)、恶丝虫属(Dirofilari)、双瓣线虫属(Dipetalonema)、腹腔丝虫属(Setaria)、油脂线虫属(Elaeophora)、狼旋尾线虫(Spirocerca lupi)和胃线虫属(Habronema),棘头虫(棘头虫纲Acanthocephala)),例如棘头虫属(Acanthocephalus)、蛭形巨棘吻棘头虫(Macracanthorhynchus hirudinaceus)和钩居棘头虫属(Oncicola),
涡虫(Plathelminthes):
吸虫(吸虫纲(Trematoda)),例如片形吸虫属(Fasciola)、大拟片形吸虫(Fascioloides magna)、并殖吸虫属(Paragonimus)、双腔吸虫属(Dicrocoelium)、巴氏姜片吸虫(Fasciolopsis buski)、华枝睾吸虫(Clonorchissinensis)、裂体吸虫属(Schistosoma)、毛毕吸虫属(Trichobilharzia)、似翼重翼吸虫(Alaria alata)、并殖吸虫属和Nanocyetes属,
Cercomeromorpha,尤其是绦虫纲(Cestoda(多节绦虫亚纲)),例如双叶槽绦虫属(Diphyllobothrium)、Tenia属、棘球绦虫属(Echinococcus)、犬复孔绦虫(Dipylidium caninum)、多头绦虫属(Multiceps)、膜壳绦虫属(Hymenolepis)、中带绦虫属(Mesocestoides)、Vampirolepis属、莫尼茨绦虫属(Moniezia)、裸头绦虫属(Anoplocephala)、Sirometra属、裸头绦虫属和膜壳绦虫属。
式(I)化合物和含有它们的组合物特别用于防治选自双翅目、蚤目和蜱科的害虫。
此外,尤其优选利用式(I)化合物和含有它们的组合物对抗蚊子。
利用式(I)化合物和含有它们的组合物对抗蝇为本发明的另一个优选实施方案。
此外,尤其优选利用式(I)化合物和含有它们的组合物对抗蚤。
利用式(I)化合物和含有它们的组合物对抗扁蚤为本发明的另一个优选实施方案。
式(I)化合物还特别可用于对抗体内寄生虫(圆线虫、棘头虫和涡虫)。
可以预防和治疗方式进行给药。活性化合物的给药直接进行或以合适的制剂形式口服、局部/经皮或肠胃外进行。
对于温血动物的口服给药,可以将式(I)化合物配制成动物饲料、动物饲料预混物、动物饲料浓缩物、丸剂、溶液、糊、悬浮液、浸液、凝胶、片剂、大丸剂和胶囊。此外,式(I)化合物可以在其饮用水中给药于动物。对于口服给药,所选剂型应给动物提供0.01-100mg/kg动物体重/天,优选0.5-100mg/kg动物体重/天的式(I)化合物。
另外,式(I)化合物可以肠胃外给药于动物,例如通过腔内(intraruminal)、肌内、静脉内或皮下注射。式(I)化合物可以分散或溶于对于皮下注射而言生理上可接受的载体中。另外,可以将式(I)化合物配制成皮下给药用植入物。此外,式(I)化合物可以透皮给药于动物。对于肠胃外给药,所选剂型应给动物提供0.01-100mg/kg动物体重/天的式I和II化合物。
式(I)化合物还可以浸洗液、粉剂、粉末、项圈、挂牌(medallions)、喷雾剂、香波、蘸点(spot-on)和喷淋配制剂形式以及以软膏或水包油或油包水乳液局部给药于动物。对于局部施用,浸洗液和喷雾剂通常含有0.5-5000ppm,优选1-3000ppm式(I)化合物。此外,式(I)化合物可以配制成动物,特别是四足动物如牛和绵羊用耳贴。
合适的制剂是:
溶液,如口服溶液、稀释后口服给药用浓缩物、用于皮肤上或用于体腔内的溶液、喷淋配制剂、凝胶;
口服或皮肤给药乳液和悬浮液;半固体制剂;
其中将活性化合物在软膏基质中或在水包油或油包水乳液基质中加工的配制剂;
固体制剂如粉末、预混物或浓缩物、颗粒、丸剂、片剂、大丸剂、胶囊;气雾剂和吸入剂,以及含有活性化合物的成型制品。
适合注射的组合物以下述方式制备,使活性成份溶解在合适的溶剂中,且任选添加其它成份,如酸类、碱类、缓冲盐、防腐剂和增溶剂。将溶液过滤并无菌充填。
合适的溶剂为生理容许的溶剂,如水,链烷醇如乙醇、丁醇、苄醇,甘油、丙二醇、聚乙二醇、N-甲基-吡咯烷酮、2-吡咯烷酮及其混合物。
可任选将活性化合物溶于适合注射的生理上容许的植物或合成油中。
合适的增溶剂为促进活性化合物溶于主要溶剂中或防止其沉淀的溶剂。实例为聚乙烯基吡咯烷酮、聚乙烯醇、聚氧乙基化蓖麻油和聚氧乙基化山梨糖醇酯。
合适的防腐剂为苄醇、三氯丁醇、对羟苯甲酸酯和正丁醇。
口服溶液直接给药。在将浓缩物在预先稀释至使用浓度后,以口服方式给药。口服溶液与浓缩物根据现有技术和上文对注射溶液所述制备,无菌程序并非必要。
喷淋、涂抹、擦拭、淋洒或喷雾上用于皮肤的溶液。
用于皮肤上的溶液根据现有技术和上文对注射溶液所述制备,无菌程序并非必要。
其它合适的溶剂为聚丙二醇、苯基乙醇、苯氧基乙醇,酯如乙酸乙酯或丁酯、苯甲酸苄酯,醚如链烷二醇烷基醚,如二丙二醇单甲基醚,酮如丙酮、甲基乙基酮,芳族烃,植物和合成油、二甲基甲酰胺、二甲基乙酰胺、乙二醇单乙醚(transcutol)、丙酮缩甘油(solketal)、碳酸亚丙酯及其混合物。
在制备过程中可有利地添加增稠剂。合适的增稠剂为无机增稠剂,如膨润土、胶态硅酸、单硬脂酸铝,有机增稠剂如纤维素衍生物、聚乙烯醇及其共聚物、丙烯酸酯和甲基丙烯酸酯。
将凝胶施加至或涂抹于皮肤上,或引入体腔中。凝胶以下述方式制备,用足量增稠剂处理已如注射溶液情况下所述制备的溶液,得到具有膏状稠度的透明材料。所用增稠剂为上文给出的增稠剂。
将倾注配制剂倾倒或喷雾在皮肤的有限区域上,活性化合物穿透皮肤并内吸地起作用。
倾注配制剂通过将活性化合物溶解、悬浮或乳化在合适的皮肤相容性溶剂或溶剂混合物中而制备。合适的话加入其它辅助剂,如着色剂、生物吸收促进物质、抗氧化剂、光稳定剂、粘合剂。
合适的溶剂为:水、链烷醇、二醇、聚乙二醇、聚丙二醇、甘油,芳族醇如苄醇、苯基乙醇、苯氧基乙醇,酯如乙酸乙酯、乙酸丁酯、苯甲酸苄酯,醚如烷二醇烷基醚类,如二丙二醇单甲基醚、二乙二醇单丁醚,酮如丙酮、甲基乙基酮,环状碳酸酯,如碳酸亚丙酯、碳酸亚乙酯,芳族和/或脂族烃、植物或合成油、DMF、二甲基乙酰胺,N-烷基吡咯烷酮,如甲基吡咯烷酮、正丁基吡咯烷酮或正辛基吡咯烷酮、N-甲基吡咯烷酮、2-吡咯烷酮、2,2-二甲基-4-氧基亚甲基-1,3-二氧戊环和甘油缩甲醛。
合适的着色剂为允许用于动物且可溶解或悬浮的所有着色剂。
合适的吸收促进物质例如为DMSO,涂抹油类,如肉豆蔻酸异丙酯、丙二醇壬酸酯、硅油及其与聚醚的共聚物,脂肪酸酯、甘油三酸酯、脂肪醇。
合适的抗氧化剂为亚硫酸盐或偏亚硫酸氢盐,如偏亚硫酸氢钾、抗坏血酸、丁基羟基甲苯、丁基羟基甲苯醚、生育酚。
合适的光稳定剂例如为novantisolic acid。
合适的粘合剂例如为纤维素衍生物、淀粉衍生物、聚丙烯酸酯,天然聚合物,如海藻酸盐、明胶。
乳液可以口服、皮肤或注射给药。
乳液为油包水或水包油类型。
它们以下述方式制备:将使活性化合物溶解于疏水或亲水相中,并用另一相的溶剂将其均化,借助合适的乳化剂以及合适的话使用其它辅助剂,如着色剂、吸收促进物质、防腐剂、抗氧化剂、光稳定剂、粘度提高物质。合适的疏水相(油)为:
液体石蜡、硅油,天然植物油如芝麻油、杏仁油、蓖麻油,合成甘油三酸酯,如甘油二辛酸/癸酸酯,具有链长C8-C12的植物脂肪酸或其它特定选择的天然脂肪酸的甘油三酸酯混合物,可能还含有羟基的饱和或不饱和脂肪酸的部分甘油酯混合物,C8-C10脂肪酸的甘油单酯和二酯,脂肪酸酯,如硬脂酸乙酯、己二酸二正丁酰酯、月桂酸己酯、丙二醇壬酸酯、中等链长的支化脂肪酸与链长C16-C18饱和脂肪醇的酯、肉豆蔻酸异丙酯、棕榈酸异丙酯、链长C12-C18的饱和脂肪醇的辛酸/癸酸酯、硬脂酸异丙酯、油酸油酯、油酸癸酯、油酸乙酯、乳酸乙酯,蜡状脂肪酸酯,如合成鸭尾骨腺脂肪、邻苯二甲酸二丁酯、己二酸二异丙酯,以及涉及后者的酯混合物,脂肪醇,如异十三烷醇、2-辛基十二烷醇、鲸蜡基硬脂基醇、油醇,和脂肪酸,如油酸及其混合物。
合适的亲水相为:水,醇,如丙二醇、甘油、山梨醇及其混合物。合适的乳化剂为:
非离子表面活性剂,例如聚乙氧基化蓖麻油、聚乙氧基化单油酸山梨糖醇酯、单硬脂酸山梨糖醇酯、单硬脂酸甘油酯、聚氧乙基硬脂酸酯、烷基酚聚乙二醇醚;两性表面活性剂,如N-月桂基-对亚氨基二丙酸二钠或卵磷脂;阴离子表面活性剂,如月桂基硫酸钠、脂肪醇醚硫酸盐、单/二烷基聚乙二醇醚正磷酸酯单乙醇胺盐;阳离子活性表面活性剂,如鲸蜡基三甲基氯化铵。
合适的其它辅助剂为:增加粘度和使乳液稳定的物质,如羧甲基纤维素、甲基纤维素及其它纤维素与淀粉衍生物、聚丙烯酸酯、海藻酸盐、明胶、阿拉伯胶、聚乙烯基吡咯烷酮、聚乙烯醇、甲基乙烯基醚与马来酸酐的共聚物、聚乙二醇、蜡、胶态硅酸或所述物质的混合物。
悬浮液可口服或局部/皮肤给药。其以下述方式制备,将活性化合物悬浮在悬浮剂中,合适的话加入其它辅助剂,如润湿剂、着色剂、生物吸收促进物质、防腐剂、抗氧化剂、光稳定剂。
液体悬浮剂为所有均相溶剂和溶剂混合物。
合适的润湿剂(分散剂)为上文给出的乳化剂。
可提及的其它辅助剂为上文给出的那些。
半固体制剂可以口服或局部/皮肤给药。其与上述悬浮液与乳液的不同仅在于其较高粘度。
对于固体制剂的制备,将活性化合物与合适的赋形剂混合,合适的话加入辅助剂,并产生所需形式。
合适的赋形剂均为生理学上容许的固体惰性物质。所用的那些为无机与有机物质。无机物质例如为氯化钠,碳酸盐,如碳酸钙、碳酸氢盐、氧化铝、二氧化钛、硅酸、陶土、沉淀或胶态硅石或磷酸盐。有机物质例如为糖、纤维素、食物和饲料如奶粉、动物粉、谷粉与谷碎片、淀粉。
合适的辅助剂为上述防腐剂、抗氧化剂和/或着色剂。
其它合适的辅助剂为润滑剂与助流剂,如硬脂酸镁、硬脂酸、滑石、膨润土,崩解促进物质如淀粉或交联的聚乙烯基吡咯烷酮,粘合剂如淀粉、明胶或线性聚乙烯基吡咯烷酮,以及干粘合剂,如微晶纤维素。
“杀寄生虫有效量”通常指对生长获得可观察到的效果所需要活性成分的量,所述效果包括坏死、死亡、阻滞、预防和去除效果,破坏效果或减少目标生物体的出现和活动的效果。对于在本发明中使用的各种化合物/组合物,杀寄生虫有效量可以变化。组合物的杀寄生虫有效量也会根据主要条件如所需杀寄生虫效果及持续时间、目标物种、施用方式等而变化。
可用于本发明的组合物通常可包含约0.001-95%的式(I)化合物。
通常而言,有利的是以每天0.5-100mg/kg,优选每天1-50mg/kg的总量施用式(I)化合物。
即用制剂含有用于抵抗寄生虫(优选体外寄生虫)的化合物,其浓度为10ppm至80重量%,优选0.1-65重量%,更优选1-50重量%,最优选5-40重量%。
在使用之前稀释的制剂含有用于抵抗体外寄生虫的化合物,其浓度为0.5-90重量%,优选1-50重量%。
此外,制剂包含抵抗体内寄生虫的式(I)化合物,其浓度为10ppm至2重量%,优选0.05-0.9重量%,非常特别优选0.005-0.25重量%。
在本发明的一个优选实施方案中,包含式(I)化合物的组合物以皮肤/局部给药。
在进一步优选实施方案中,局部给药以含化合物成型制品如项圈、挂牌(medallions)、耳贴、固定在身体部分上的绷带和粘合条与箔的形式进行。
通常而言,有利的是施用在三周内释放总量为10-300mg/kg,优选20-200mg/kg,最优选25-160mg/kg被处理动物体重的式(I)化合物的固体配制剂。
对于成型制品的制备,热塑性与柔性塑料,以及弹性体与热塑性弹性体。合适的塑料与弹性体为与式(I)化合物充分相容的聚乙烯基树脂、聚氨酯、聚丙烯酸酯、环氧树脂、纤维素、纤维素衍生物、聚酰胺和聚酯。塑料与弹性体的细节以及成型制品的制备程序例如在WO 03/086075中给出。
可用于对抗啮齿动物和其他脊椎动物害虫而施加的本发明组合物尤其包括诱饵配制剂,以及种子处理配制剂,因为处理的种子本身可用作诱饵。
除了至少一种式(I)化合物、其盐或N-氧化物之外,诱饵配制剂还包括至少一种诱饵材料和任选其他成分,如引诱剂、止痛药、生物杀伤剂、辅助剂和/或其他常用于诱饵配制剂的配制添加剂。合适的诱饵配制剂例如主要描述于DE 2506769、EP 317260、US 4,190,734、GB 1053088、GB1274442、DE 4444261、WO 98/04129、WO 01/80645、WO 2003/094612、WO 2007/057393、WO 2007/031796和WO 2009/047175等及其中引用的文献中。
式(I)化合物、其盐或其N-氧化物的总量基于配制剂的总重量通常为0.001-50重量%,剩余部分包括至少一种诱饵材料和任选的本文所述的其他成分。
常用的诱饵材料为植物或动物食品和饲料。合适的实例为粗谷粉、谷粒、碎谷粒或谷粉(例如燕麦、小麦、大麦、玉米、大豆、米的那些),碎椰子,研磨的椰子、糖浆(例如通过水解淀粉而得到(葡糖糖浆),转化糖浆,甜菜糖浆,槭糖浆),糖(例如蔗糖、乳糖、果糖、葡萄糖),搓碎的坚果、研磨的坚果(例如榛子、胡桃、杏仁),植物脂肪/油(例如菜子油、大豆脂肪、向日葵油、可可脂、花生油、花生酱、玉米油),动物脂肪/油(黄油、猪油、鱼油),蛋白质(例如干的脱脂奶、干的蛋、蛋白质水解物)和矿物(如食盐)。
优选植物食品,如燕麦片、碎燕麦、小麦粒、粗小麦粉、小麦面粉、玉米粉、碎椰子、研磨的椰子、葡萄糖浆、槭糖浆、甜菜糖浆、蔗糖、葡萄糖、研磨的榛子、研磨的胡桃、杏仁、菜子油、大豆脂、花生油、玉米油;动物脂肪,如黄油;蛋白质,如干的蛋和干的脱脂奶。
特别优选植物食品,如燕麦片、玉米粉、碎的椰子、研磨的椰子、葡萄糖浆、槭糖浆、蔗糖、研磨的榛子、大豆脂、花生油、花生酱和蛋白质,如干的脱脂奶。
对本发明而言,引诱剂为诱食剂或吸引啮齿动物害虫注意力到诱饵的物质(或物质混合物),其尤其通过气味(例如性引诱剂)吸引,并且在另一方面严格来说并不是饲料。引诱剂的实例为信息素、酵母、研磨的甲壳、排泄物质、浆果、巧克力、鱼粉、肉、黑胡椒和气味增强剂,如谷氨酸盐,尤其是谷氨酸钠和甘氨酸二钠。
诱饵材料在配制剂中的量可取决于配制剂类型而变化。基于配制剂的重量,诱饵材料的量通常为1-99.99重量%。杀菌剂的实例包括异噻唑啉酮,如购自ICI的或购自ThorChemie的RS,购自Rohm&Haas的MK和购自DowElanco的
优选止痛药为镇痛药(analgesics)和镇静剂以及镇痛药和镇静剂的混合物。
镇痛药的实例包括吗啡、可待因(codeine)、双氢可待因(dihydrocodeine)、氢化吗啡、羟可酮(oxycodone)、杜冷丁(pethidine)、曲马朵(tramadol)、美沙酮(methadone)、乙酰水杨酸(acetylsalicylic acid)、二氟尼柳(diflunisal)、萘普生(naproxen)、proxicam、替诺昔康(tenoxicam)、美洛昔康(meloxicam)、扑热息痛(paracetamol)和非那宋(phenazone)。
镇静剂的实例包括二异丙酚(propofol)、可乐定(clonidine),巴比妥酸盐类(barbiturates),如苯巴比妥(Phenobarbital)和戊巴比妥(pentobarbital)和苯二氮卓类,尤其是在抗焦虑药(anxiolytics)中提及的那些。
镇痛药(analgesics)和镇静剂的优选混合物为包含一种或多种选自吗啡、可待因(codeine)、双氢可待因(dihydrocodeine)、氢化吗啡、羟可酮(oxycodone)、杜冷丁(pethidine)、曲马朵(tramadol)、美沙酮(methadone)、乙酰水杨酸、二氟尼柳(diflunisal)、萘普生(naproxen)、proxicam、替诺昔康(tenoxicam)、美洛昔康(meloxicam)、扑热息痛(paracetamol)和非那宋(phenazone)的镇痛药和一种或多种选自二异丙酚(propotol)、可乐定(clonidine)、苯巴比妥(Phenobarbital)、戊巴比妥(pentobarbital)、阿普唑仑(alprazolam)、溴西泮(bromazepam)、溴替唑仑(brotizolam)、氯氮卓(chlordiazepoxide)、氯巴占(clobazam)、氯硝西泮(clonazepam)、地西泮(diazepam)、氯拉卓酸(clorazepate)、氟硝西泮(flunitrazepam)、氟西泮(flurazepam)、氯普唑仑(loprazolam)、劳拉西泮(lorazepam)、氯甲西泮(lormetazepam)、美达西泮(medazepam)、咪达唑仑(midazolam)、硝西泮(nitrazepam)、去甲西泮(nordazepam)、奥沙西泮(oxazepam)、普拉西泮(prazepam)、替马西泮(temazepam)、四氢西泮(tetrazepam)和三唑仑(triazolam)的镇静剂的混合物。
其他常规配制添加剂包括着色剂、苦味剂、流动剂、粘合剂、用于改善耐天候老化的试剂和抗氧化剂。
经常加入着色剂,因此诱饵配制剂被显著标记而不被消费,以避免被人类或非目标动物误食。蓝色着色剂尤其用于阻止鸟类。然而,它们也可用于在啮齿动物害虫的粪便或呕吐物中检测诱饵的消费。
苦味剂用于避免被人类偶尔消费。尤其优选苯甲地那铵(denatoniumbenzoate),其在合适的浓度(通常1-200ppm,尤其是5-20ppm)下对人类具有最不愉悦的味道,而对于啮齿动物并不如此。
取决于诱饵配制剂的类型,加入流动剂和粘合剂。粘合剂能够将本发明混合物固定到诱饵组分(例如谷粒)的表面或在糊的情况下,例如用于赋予结构和粘附。流动剂,如矿土和铝硅酸盐有助于挤出,因此,它们经常用于粒料和挤出块中。
适用于改善耐天候老化的试剂例如为石蜡。
合适的抗氧化剂的实例为叔丁基氢醌(TBHQ)、丁基化羟基甲苯和丁基化羟基茴香醚,其量优选为10-20000ppm。
优选的诱饵配制剂为食物诱饵,尤其是谷种诱饵和合适的处理剂,粒料(模具形成的制品)、涂覆蜡的粒料、熔融蜡块、压缩或挤出蜡块、糊、凝胶、颗粒和泡沫。
饲料诱饵经常由谷物组成,谷物可以以不同形式存在,如谷粒或者以程度不同的细碎粉形式。
呈粉形式的诱饵的优点在于难以被动物带走或储存,但是易于处理(粉剂)并快速损害。完整谷粒的缺点在于它们也可被非目标动物,如鸟类食用,在某些情况下也可被人类食用。
本发明化合物和任选其他辅助剂可施用于饲料表面,尤其是与粘合剂结合施用于饲料表面。因此,优选用至少一种本发明化合物以种子处理的方式处理这类饲料。因此,类似于WO 2007/057393,用于处理种子以制备基于种子的诱饵的合适配制剂可包含:
(a)至少一种式(I)化合物或其盐或N-氧化物,其任选与至少一种止痛药结合;
(b)至少一种多元醇;
(c)粘合剂,以及合适的话,
(d)单糖和/或二糖和/或寡糖。
在这类组合物中,多元醇含量基于组合物的重量可为1-50重量%,优选1-20重量%。
粘合剂含量基于组合物的重量可为1-30重量%,优选1-10重量%,特别优选1-5重量%。
单糖和/或二糖和/或寡糖含量基于组合物的重量可为10-50.0重量%,优选10.0-35.0重量%,特别优选15.0-25.0重量%。
合适的多元醇包括乙二醇、聚乙二醇、甘油、丙二醇、二丙二醇,优选甘油。
作为组分c)优选使用单糖和二糖。非常特别优选使用二糖。合适的单糖为葡萄糖、果糖、半乳糖,优选果糖。合适的二糖为蔗糖、麦芽糖、乳糖,优选蔗糖(例如以纯净形式或作为糖蜜,甜菜糖)。合适的寡糖为淀粉。
合适的粘合剂为氧化乙烯/氧化丙烯共聚物,聚乙烯醇(例如4-98,Clariant,60-20,Rhone-Poulence),聚乙烯基吡咯烷酮(HP 50,BASF,25,BASF,K80,BASFA,ISP Global Techn),聚丙烯酸酯(例如PA 110S,BASF),聚甲基丙烯酸甲酯,水溶性聚烯烃衍生物,如聚丁烯衍生物,聚氧乙烯(例如聚醚)或聚异丁基衍生物(如聚烯烃和马来酸酐衍生物的共聚物(例如BASF的Densodrin),聚苯乙烯衍生物(如苯乙烯和马来酸酐衍生物的共聚物,或苯乙烯和丙烯酸衍生物的共聚物,或基于苯乙烯/丁二烯的胶乳共聚物,其例如可以Semkote E-125得自Uniqema),以及聚乙烯胺,聚乙烯酰胺,聚乙烯亚胺(例如BASF,,BASF),聚氨酯(Semkote E-105,Uniqema),聚乙酸乙烯酯、纤基乙酸钠和聚乙烯蜡(例如可以以WE 7 BASF市购,优选氧化乙烯/氧化丙烯共聚物,聚丙烯酸酯(例如PA 110S,BASF),聚甲基丙烯酸甲酯,水溶性聚烯烃衍生物,如聚丁烯衍生物,聚氧乙烯(例如聚醚)或聚异丁基衍生物(如聚烯烃和马来酸酐衍生物的共聚物(例如BASF的Densodrin),聚苯乙烯衍生物(如苯乙烯和马来酸酐衍生物的共聚物,或苯乙烯和丙烯酸衍生物的共聚物,或基于苯乙烯/丁二烯的胶乳共聚物,其例如可以Semkote E-125得自Uniqema),以及聚乙烯胺,聚乙烯酰胺,聚乙烯亚胺(例如BASF,,BASF),聚氨酯(Semkote E-105,Uniqema),聚乙酸乙烯酯和聚乙烯蜡(例如可以以WE 7BASF市购);特别优选氧化乙烯/氧化丙烯共聚物,聚丙烯酸酯(例如PA 110S,BASF),聚甲基丙烯酸甲酯,聚苯乙烯衍生物(如苯乙烯和马来酸酐衍生物的共聚物,或苯乙烯和丙烯酸衍生物的共聚物,或基于苯乙烯/丁二烯的胶乳共聚物,其例如可以Semkote E-125得自Uniqema),以及聚乙烯蜡(例如可以以WE 7BASF市购);
此外,本发明诱饵配制剂可任选包含又一辅助剂,如表面活性剂(如润湿剂、粘合剂和分散剂),消泡剂,增稠剂和着色剂。
处理可通过熟练技术人员已知的方法进行(如通过用本发明配制剂喷雾或浸渍/培育谷粒,合适的话使用合适的装置,如连续或分批操作的拌种机)。这样做时,配制剂可优选用至多7.5g 水/kg谷粒稀释。可任选将处理的谷粒干燥。
此外,优选作为诱饵配制剂的是所谓的粒料(模具形成的制品)。这类粒料包含本发明式(I)化合物或(I)的盐或N-氧化物,其呈与任选粉末化或研磨的饲料(B),尤其是谷物,和增稠剂,和其他配制添加剂(C)的混合物形式。粒料通常通过压缩、挤出和随后干燥而制备。
粒料尺寸取决于目标动物而变化。粒料通常以直径为3-5mm和长度为5-10mm的圆柱体形式制备。
本发明化合物的含量通常为粒料的0.001-30重量%。
为了增加粒料的耐天候老化,在本发明的一个实施方案中加入石蜡,然而石蜡降低了用于啮齿动物害虫的粒料的可口性。
另一优选诱饵配制剂为蜡块配制剂,其除了至少一种式(I)化合物或其盐或N-氧化物外还包含饲料,通常为谷粒,粗谷粉或谷粉末(B),以及合适的话配制添加剂(C)和石蜡的混合物。蜡块配制剂的优点在于它们具有良好的耐天候老化;然而,牺牲了对于啮齿动物害虫的可口性。蜡块配制剂通常通过浇铸、挤出或压缩而制备,在最后提及的方法中的蜡含量是较低的,并具有类似良好的耐天候老化,这增加了可口性。蜡块配制剂可以制备为许多形状,这允许它们悬挂或固定在诱饵位置。在优选实施方案中,蜡块包含多个角,这是因为动物优先啃角。
另一优选的诱饵配制剂为颗粒,其除了至少一种式(I)化合物或其盐或N-氧化物外,还包含通常粉碎,如研磨的饲料(R)以及合适的话其他添加剂和粘合剂。颗粒的制备例如描述于EP-A 0771393中。
还优选的诱饵配制剂为凝胶(例如参见WO 03/094612和其中所引用的文献)。优选这类凝胶包含:
-作为分散剂的水;
-至少一种增稠剂;
-至少一种本发明化合物;
-一种或多种饲料;
在优选实施方案中,凝胶额外包含一种或多种如下组分:
-碱;
-保湿剂;
-氧化稳定剂;
-着色剂;
-苦味剂;
-其他添加剂。
所用增稠剂为有机和无机大分子。可提及的有机大分子为纤维素衍生物,如羟丙基纤维素、羟乙基纤维素、甲基纤维素、羧甲基纤维素钠、羟丙基甲基纤维素、羟乙基甲基纤维素、羟乙基丙基纤维素,如黄原胶,藻酸盐,角叉菜胶,琼脂,聚乙烯醇,聚乙烯基吡咯烷酮,聚丙烯酸和聚甲基丙烯酸。可提及的无机大分子(无机凝胶前体)为高度分散的硅石和膨润土(例如Rudolf Voigt,Pharmazeutische Technologie[药物技术],第362-385页,Ulstein Mosby)。
所用碱例如为碱金属氢氧化物、碱土金属氢氧化物和氨基衍生物,如氢氧化钾、氢氧化钠、三乙醇胺或氢氧化铵溶液。碱可用于调节pH。
所用保湿剂例如为多元醇,如甘油、丙二醇、乙二醇、糖醇和聚丙二醇。保湿剂防止凝胶干燥从而保持其弹性并且在被啮齿动物摄取时不分散。优选保湿剂为甘油、丙二醇、聚丙二醇200、丙二醇300、聚丙二醇400、山梨糖醇、甘露糖醇和木糖醇。
可提及的氧化稳定剂为丁基羟基甲苯、丁基羟基茴香醚、生育酚(如维生素E)或抗坏血酸及其衍生物(如抗坏血酸棕榈酯、抗坏血酸钠)。食品和饲料可通过加入氧化稳定剂稳定。特别优选丁基羟基甲苯、维生素E、抗坏血酸。
可提及的着色剂为蓝色、绿色和红色颜料以及蓝色、绿色和红色可溶性染料(参见Colour Index(染料索引),第4版:Hue blue,red,green(蓝、红、绿色调),优选将蓝色着色剂用于阻止鸟类。本发明凝胶也可通过着色剂着色以用于警告目的。
优选允许用于着色化妆品的合适着色剂(例如参见,Dievon Lebensmitteln,Arzneimitteln,Kosmetika[着色食品、药物、化妆品],Behr′s Verlag,第2版,第52-57页。优选使用颜料作为着色剂。
可使用的添加剂例如为苦味剂,如苯甲地那铵以及天然和合成的芳香化学品(例如参见Hamann&Reimer,Holzminden的产品列)。
诱饵配制剂的另一优选类型为高耐久泡沫或柔性泡沫,优选柔性泡沫。可根据本发明使用的高耐久泡沫例如描述于FR-PS 2676888和US4,190,734。可根据本发明使用的柔性泡沫例如描述于GB-PS 1053088和GB1274442。
优选泡沫为描述于DE-A 4444261的柔性泡沫。这类柔性泡沫包含:
-至少一种本发明化合物,
-至少一种平均分子量为2000-60000(通过凝胶渗透色谱法(GPC)测定)的亲水聚合物,其优选选自长链聚氨酯、聚酯、聚酯多元醇、聚苯乙烯、聚丁二烯、马来酸聚合物系列的各自通过羧基和/或氨基在聚合物链中改性,
-长链脂族C6-C22脂肪酸,如棕榈酸、十二烷酸和硬脂酸,或其碱金属盐、碱土金属盐和铵盐,
-以及合适的话选自着色剂、乳化剂、溶剂、引诱剂和饲料的其他辅助剂。
亲水聚合物在本领域是已知的且例如描述于H.Kittel,Lehrbuch derLacke und Beschichtungen[漆和涂料教科书],第IV卷,第76-306页,Verlag W.A.Colomb(1096)或相同的教科书,版本(1976),第IV卷,第328-358页,作为用于漆的粘合剂。
可用于柔性泡沫的亲水聚合物为物理干燥的粘合剂,如其粘合剂为基于(i)聚酯多元醇,(ii)增链剂和(iii)二异氰酸酯和(iv)羟基羧酸的全反应的线性聚氨酯的那些。适用于制备这类聚氨酯的聚酯多元醇(i)例如为己二酸、链烷二醇、分子量为600-3000(数均)的聚酯二醇。链烷二醇例如为丁烷-1,4-二醇、己烷-1,6-二醇、新戊二醇或这类二醇的混合物。合适的增链剂(ii)例如为用于制备聚酯二醇的二醇类型,以及二胺,如六亚甲基二胺或异佛尔酮二胺。合适的二异氰酸酯(iii)的实例为4,4′-二苯基甲烷二异氰酸酯、异佛尔酮二异氰酸酯或六亚甲基二异氰酸酯。聚氨酯通过本身已知的方法通过使原料反应而制备,其中维持0.9∶1-1.1∶1的异氰酸酯基团与异氰酸酯反应性基团的当量比。
也可使用氧化干燥粘合剂(Oxidatively drying binder)。可提及的这类粘合剂为基于聚丁二烯、苯乙烯和马来酸酐且具有离子基团的那些,它们描述于申请EP 170184和EP 270795中。
亲水聚合物的平均分子量通常为2000-60000g/mol,优选2500-25000g/mol(数均)。基于配制剂的总重量,它们以2.5-40重量%,优选2.5-10重量%的浓度存在于最终配制剂中。
泡沫配制剂通常为预混物。在施用前,通常必须用0-80%的水稀释它们。
柔性泡沫可以本身已知的方式,通过搅拌或振摇而制备。另一可能性为在施用过程中使用发泡剂原位制备。
可提及的用于制备本发明配制剂的发泡剂为CO2,N2O,低级链烷烃,如丙烷或正丁烷,异丁烷,含卤素的低级链烷烃和低沸点醚,如二甲醚以及所述发泡剂的混合物。
合适的诱饵配制剂也可包括一种颗粒混合物,其除了包含饲料和至少一种本发明化合物的颗粒外还包含含有具有不同于第一饲料的气味的饲料的颗粒,该颗粒在尺寸、形状、表面结构、内部结构、颜色、密度和/或含量方面不同于首先提及的颗粒。例如,非杀鼠颗粒以2.5-10重量%(基于全部配制剂)的量存在。非杀鼠颗粒优选基于谷物且优选包含至少一种选自巧克力、干且研磨的甲壳、酵母、排泄物、鱼粉、肉和浆果的其它引诱剂。这类颗粒配制剂的实例描述于WO 2007/031796。
因此,本发明还涉及一种防治啮齿动物害虫的方法,其中将本发明诱饵配制剂施用于有害的脊椎动物的栖息地。
本发明还涉及本发明诱饵配制剂在防治啮齿动物害虫中的用途。
诱饵配制剂适合施用于房间,如地窖,储藏间,食品室,动物屋,或施用于水槽和开放施用,如用于啮齿动物害虫的路线或用于它们居住的洞穴。
本发明诱饵配制剂施用于诱饵箱中。这类诱饵箱例如描述于US3,750,326、US 4,349,982、DE-A 19501892、WO 02/102147、DE-A 102004022105和DE-A 102004022103中。
根据本发明使用的组合物可以含有其他活性成分如其它农药、杀虫剂、除草剂,杀真菌剂,其他农药或杀菌剂,肥料,如硝酸铵、尿素、钾碱与过磷酸盐、植物毒剂与植物生长调节剂、安全剂和杀线虫剂。这些其它成份可与上述组合物依次或以组合物使用,合适的话恰在紧邻使用前加入(桶混合)。例如可在用其它活性成分处理之前或之后,用本发明组合物喷雾植物。
这些试剂可与根据本发明使用的试剂以1∶10-10∶1的重量比混合。将农药使用形式的式(I)化合物或包含它们的组合物与其他农药混合,经常产生较宽的杀虫活性谱。
本发明化合物可与其一起使用,以及可能与其产生协同增效作用的下列农药M,意欲说明可能的组合,而不施加任何限制:
M.1.有机(硫代)磷酸酯类:高灭磷(acephate)、唑啶磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、谷硫磷(azinphos-methyl)、壤虫氯磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲磷(chlormephos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、苯硫磷(EPN)、乙硫磷(ethion)、灭克磷(ethoprophos)、氨磺磷(famphur)、克线磷(fenamiphos)、杀螟松(fenitrothion)、倍硫磷(fenthion)、吡氟硫磷(flupyrazophos)、噻唑酮磷(fosthiazate)、庚虫磷(heptenophos)、异唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧化乐果(omethoate)、砜吸磷(oxydemeton-methyl)、一六零五(parathion)、甲基一六零五(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、烯虫磷(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、打杀磷(pyridaphenthion)、喹恶磷(quinalphos)、治螟磷(sulfotep)、嘧丙磷(tebupirimfos)、硫甲双磷(temephos)、特丁磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(trichlorfon)、蚜灭多(vamidothion)
M.2.氨基甲酸酯类:涕灭威(aldicarb)、棉铃威(alanycarb)、虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁叉威(butocarboxim)、氧丁叉威(butoxycarboxim)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、苯虫威(ethiofencarb)、丁苯威(fenobucarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭威(metolcarb)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、特氨叉威(thiofanox)、混杀威(trimethacarb)、二甲威(XMC)、灭杀威(xylylcarb)、唑蚜威(triazamate);
M.3.合成除虫菊酯类:氟锁草醚(acifluorfen)、丙烯除虫菊(allethrin)、d-顺-反丙烯除虫菊、d-反丙烯除虫菊、氟氯菊酯(bifenthrin)、反丙烯除虫菊(bioallethrin)、反丙烯除虫菊S-环戊烯基(bioallethrin S-cylclopentenyl)、右旋反灭虫菊酯(bioresmethrin)、乙氰菊脂(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、β-氟氯氰菊酯、(RS)氯氟氰菊酯(cyhalothrin)、λ-(RS)氯氟氰菊酯、γ-(RS)氯氟氰菊酯、氯氰菊酯(cypermethrin)、甲体氯氰菊酯(alpha-cypermethrin)、乙体氯氰菊酯(beta-cypermethrin)、辛体氯氰菊酯(theta-cypermethrin)、己体氯氰菊酯(zeta-cypermethrin)、苯醚氰菊酯(cyphenothrin)、溴氰菊酯(deltamethrin)、烯炔菊酯(empenthrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(Tau-Fluvalinate)、卤醚菊酯(halfenprox)、咪炔菊酯(imiprothrin)、甲氧苄氟菊酯(metofluthrin)、氯菊酯(permethrin)、苯醚菊酯(phenothrin)、炔酮菊酯(prallethrin)、profluthrin、除虫菊酯(pyrethrin)(pyrethrum)、灭虫菊(resmethrin)、灭虫硅醚(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)、四氟菊酯(transfluthrin);
M.4.拟保幼激素(juvenile hormone mimics):蒙五一二(hydroprene)、蒙七七七(kinoprene)、蒙五一五(methoprene)、双氧威(fenoxycarb)、蚊蝇醚(pyriproxyfen);
M.5.烟碱受体激动剂/拮抗剂化合物:吡虫清(acetamiprid)、杀虫磺(bensultap)、巴丹(cartap hydrochloride)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、噻虫嗪(thiamethoxam)、硝胺烯啶(nitenpyram)、烟碱(nicotine)、艾克敌105(spinosad)(变构激动剂)、spinetoram(变构激动剂)、噻虫啉(thiacloprid)、硫环杀(thiocyclam)、杀虫双(thiosultap-sodium)和AKD1022。
M.6.GABA门控氯离子通道拮抗剂化合物:氯丹(chlordane)、硫丹(endosulfan)、林丹(gamma-HCH)、acetoprole、乙虫清(ethiprole)、锐劲特(fipronil)、pyrafluprole、pyriprole、氟吡唑虫(vaniliprole);
M.7.氯离子通道活化剂:齐墩螨素(abamectin)、甲氨基阿维菌素(emamectin benzoate)、米尔螨素(milbemectin)、lepimectin;
M.8.METI I化合物:喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧胺苯醚(pyrimidifen)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)、flufenerim、鱼藤酮(rotenone);
M.9.METI II和III化合物:灭螨醌(acequinocyl)、fluacyprim、灭蚁腙(hydramethylnon);
M.10.氧化磷酸化去偶剂(Uncoupler):氟唑虫清(chlorfenapyr),二硝甲酚(DNOC);
M.11.氧化磷酸化抑制剂:唑环锡(azocyclotin)、三环锡(cyhexatin)、杀螨硫隆(diafenthiuron)、杀螨锡(fenbutatin oxide)、克螨特(propargite)、三氯杀螨砜(tetradifon);
M.12.蜕皮干扰剂(Moulting disruptor):cryomazine、chromafenozide、特丁苯酰肼(halofenozide)、甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide);
M.13.增效剂:增效醚(piperonyl butoxide)、脱叶磷(tribufos);
M.15.熏蒸剂:甲基溴、氯化苦(chloropicrin)、磺酰氟(sulfuryl fluoride)
M.16.选择性进食阻断剂(Selective feeding blocker):氟铝酸钠(cryolite)、拒嗪酮(pymetrozine)、氟啶虫酰胺(flonicamid);
M.18.甲壳素合成抑制剂:噻嗪酮(buprofezin)、双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、伏虫隆(teflubenzuron)、杀虫隆(triflumuron);
M.19.类脂生物合成抑制剂:螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、spirotetramat;
M.20.章鱼胺激动剂(octapaminergic agonist):虫螨脒(amitraz);
M.21.鱼尼汀(ryanodine)受体调节剂:氟虫酰胺(flubendiamide)、(R)-,(S)-3-氯-N1-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-N2-(1-甲基-2-甲基磺酰基乙基)邻苯二甲酰胺(M21.1);
M.22.其它:磷化铝、amidoflumet、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、硼砂、溴螨酯(bromopropylate)、氰化物、cyenopyrafen、丁氟螨酯(cyflumetofen)、灭螨猛(chinomethionate)、开乐散(dicofol)、氟乙酸酯、膦、啶虫丙醚(pyridalyl)、pyrifluquinazon、硫、有机硫化合物、吐酒石(tartar emetic);sulfoxaflor、4-丁-2-炔氧基-6-(3,5-二甲基-哌啶-1-基)-2-氟-嘧啶(M22.1)、3-苯甲酰基氨基-N-[2,6-二甲基-4-(1,2,2,2-四氟-1-三氟甲基-乙基)-苯基]-2-氟-苯甲酰胺(M22.2)、4-[5-(3,5-二氯-苯基)-5-三氟甲基-4,5-二氢-异唑-3-基]-2-甲基-N-吡啶-2-基甲基-苯甲酰胺(M22.3)、4-[5-(3,5-二氯-苯基)-5-三氟甲基-4,5-二氢-异唑-3-基]-2-甲基-N-(2,2,2-三氟-乙基)-苯甲酰胺(M22.4)、4-[5-(3,5-二氯-苯基)-5-三氟甲基-4,5-二氢-异唑-3-基]-2-甲基-N-噻唑-2-基甲基-苯甲酰胺(M22.5)、4-[5-(3,5-二氯-苯基)-5-三氟甲基-4,5-二氢-异唑-3-基]-2-甲基-N-(四氢呋喃-2-基甲基)-苯甲酰胺(M22.6)、
4-{[(6-溴吡啶-3-基)甲基](2-氟乙基)氨基}呋喃-2(5H)-酮(M22.7)、
4-{[(6-氟吡啶-3-基)甲基](2,2-二氟乙基)氨基}呋喃-2(5H)-酮(M22.8)、
4-{[(2-氯1,3-噻唑-5-基)甲基](2-氟乙基)氨基}呋喃-2(5H)-酮(M22.9)、
4-{[(6-氯吡啶-3-基)甲基](2-氟乙基)氨基}呋喃-2(5H)-酮(M22.10)、
4-{[(6-氯吡啶-3-基)甲基](2,2-二氟乙基)氨基}呋喃-2(5H)-酮(M22.11)、
4-{[(6-氯-5-氟吡啶-3-基)甲基](甲基)氨基}呋喃-2(5H)-酮(M22.12)、
4-{[(5,6-二氯吡啶-3-基)甲基](2-氟乙基)氨基}呋喃-2(5H)-酮(M22.13)、
4-{[(6-氯-5-氟吡啶-3-基)甲基](环丙基)氨基}呋喃-2(5H)-酮(M22.14)、
4-{[(6-氯吡啶-3-基)甲基](环丙基)氨基}呋喃-2(5H)-酮(M22.15)、
4-{[(6-氯吡啶-3-基)甲基](甲基)氨基}呋喃-2(5H)-酮(M22.16),
环丙烷乙酸、1,1′-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-环丙基乙酰基)氧基]甲基]-1,3,4,4a,5,6,6a,12,12a,12b-十氢-12-羟基-4,6a,12b-三甲基-11-氧代-9-(3-吡啶基)-2H,11H-萘并[2,1-b]吡喃并[3,4-e]吡喃-3,6-二基]酯(M22.17)、8-(2-环丙基甲氧基-4-甲基-苯氧基)-3-(6-甲基-哒嗪-3-基)-3-氮杂-双环[3.2.1]辛烷(M22.18);
M.23.N-R′-2,2-二卤代-1-R″环丙烷甲酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)腙或N-R′-2,2-二(R′″)丙酰胺-2-(2,6-二氯-α,α,α-三氟-对甲苯基)-腙,其中R′为甲基或乙基,卤代为氯或溴,R″为氢或甲基且R′″为甲基或乙基;
M.24.邻氨基苯甲酰胺(anthranilamide):chloranthraniliprole、cyantraniliprole;
5-溴-2-(3-氯-吡啶-2-基)-2H-吡唑-3-甲酸[4-氰基-2-(1-环丙基-乙基氨基甲酰基)-6-甲基-苯基]-酰胺(M24.1),
5-溴-2-(3-氯-吡啶-2-基)-2H-吡唑-3-甲酸[2-氯-4-氰基-6-(1-环丙基-乙基氨基甲酰基)-苯基]-酰胺(M24.2),
5-溴-2-(3-氯-吡啶-2-基)-2H-吡唑-3-甲酸[2-溴-4-氰基-6-(1-环丙基-乙基氨基甲酰基)-苯基]-酰胺(M24.3),
5-溴-2-(3-氯-吡啶-2-基)-2H-吡唑-3-甲酸[2-溴-4-氯-6-(1-环丙基-乙基氨基甲酰基)-苯基]-酰胺(M24.4),
5-溴-2-(3-氯-吡啶-2-基)-2H-吡唑-3-甲酸[2,4-二氯-6-(1-环丙基-乙基氨基甲酰基)-苯基]-酰胺(M24.5),
5-溴-2-(3-氯-吡啶-2-基)-2H-吡唑-3-甲酸[4-氯-2-(1-环丙基-乙基氨基甲酰基)-6-甲基-苯基]-酰胺(M24.6),
M.25.丙二腈化合物:CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF3(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,3-三氟-丙基)丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)5CF2H、(2-(2,2,3,3,4,4,5,5,6,6,7,7-十二氟-庚基)-2-(3,3,3-三氟-丙基)-丙二腈)、CF3(CH2)2C(CN)2(CH2)2C(CF3)2F(2-(3,4,4,4-四氟-3-三氟甲基-丁基)-2-(3,3,3-三氟-丙基)-丙二腈)、CF3(CH2)2C(CN)2(CH2)2(CF2)3CF3(2-(3,3,4,4,5,5,6,6,6-九氟-己基)-2-(3,3,3-三氟-丙基)-丙二腈)、CF2H(CF2)3CH2C(CN)2CH2(CF2)3CF2H(2,2-双-(2,2,3,3,4,4,5,5-八氟-戊基)-丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)3CF3(2-(2,2,3,3,4,4,5,5,5-九氟-戊基)-2-(3,3,3-三氟-丙基)-丙二腈)、CF3(CF2)2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,4-七氟-丁基)-2-(2,2,3,3,4,4,5,5-八氟-戊基)-丙二腈)、CF3CF2CH2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,5,5-八氟-戊基)-2-(2,2,3,3,3-五氟-丙基)-丙二腈)、CF2HCF2CF2CF2CH2C(CN)2CH2CH2CF2CF3(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,4,4,4-五氟丁基)-丙二腈)、CF3(CH2)2C(CN)2CH2(CF2)3CF2H(2-(2,2,3,3,4,4,5,5-八氟戊基)-2-(3,3,3-三氟-丁基)-丙二腈);
M.26.微生物干扰物(disruptor):苏云金芽孢杆菌以色列亚种(Bacillusthuringiensis subsp.Israelensi)、球形芽孢杆菌(Bacillus sphaericus)、苏云金芽胞杆菌鲇泽亚种(Bacillus thuringiensis subsp.Aizawai)、苏云金芽孢杆菌库斯克亚种(Bacillus thuringiensis subsp.Kurstaki)、苏云金芽胞杆菌拟步行甲亚种(Bacillus thuringiensis subsp.Tenebrionis);
组M的市售化合物可在The Pesticide Manual,第13版,British CropProtection Council(2003)和其它出版物中找到。
式M6.1的硫酰胺及其制备描述于WO 98/28279中。Lepimectin由Agro Proj ect,PJB Publications Ltd,2004年11月已知。Benclothiaz及其制备描述于EP-A1454621中。杀扑磷和对氧磷及其制备描述于FarmChemicals Handbook,第88卷,Meister Publishing Company,2001中。Acetoprole及其制备描述于WO 98/28277中。氰氟虫胺及其制备描述于EP-A1462456中。吡氟硫磷描述于Pesticide Science 54,1988,第237-243页和US 4822779中。Pyrafluprole及其制备描述于JP 2002193709和WO 01/00614中。Pyriprole及其制备描述于WO 98/45274和US 6335357中。Amidoflumet及其制备描述于US 6221890和JP 21010907中。Flufenerim及其制备描述于WO 03/007717和WO 03/007718中。AKD 1022及其制备描述于US 6300348中。chloranthraniliprole描述于WO 01/70671、WO 03/015519和WO 05/118552中。式M24.1的邻氨基苯甲酰胺描述于WO 01/70671、WO 04/067528和WO 05/118552中。Cyflumetofen及其制备描述于WO 04/080180中。氨基喹唑啉酮化合物pyrifluquinazon描述于EP A 1097932中。亚砜亚胺sulfoxaflor描述于WO2006/060029和WO2007/149134中。炔基醚化合物M22.1例如描述于JP 2006131529。有机硫化合物描述于WO 2007060839。羧酰胺化合物M 22.2由WO 2007/83394已知。唑啉化合物M 22.3-M 22.6描述于WO 2007/074789。呋喃化合物M 22.7-M 22.16例如描述于WO 2007/115644。Pyripyropene衍生物M22.17描述于WO 2008/66153和WO 2008/108491。哒嗪化合物M 22.18描述于JP 2008/115155。丙二睛化合物描述于WO 02/089579、WO 02/090320、WO 02/090321、WO 04/006677、WO 05/068423、WO 05/068432和WO05/063694。
杀真菌混合搭档为选自下组的那些:酰基丙氨酸类,例如苯霜灵(benalaxyl)、甲霜灵(metalaxyl)、甲呋酰胺(ofurace)或霜灵(oxadixyl),胺衍生物类,例如4-十二烷基-2,6-二甲基吗啉(aldimorph)、多果定(dodine)、吗菌灵(dodemorph)、丁苯吗啉(fenpropimorph)、苯锈啶(fenpropidin)、双胍盐(guazatine)、双胍辛醋酸盐(iminoctadine)、螺茂胺(spiroxamine)或克啉菌(tridemorph),苯胺基嘧啶类,例如二甲嘧菌胺(pyrimethanil)、嘧菌胺(mepanipyrim)或环丙嘧啶(cyprodinil),抗菌素,例如放线菌酮(cycloheximide)、灰黄霉素(griseofulvin)、春雷素(kasugamycin)、多马霉素(natamycin)、多氧霉素(polyoxin)或链霉素(streptomycin),唑类,例如双苯三唑醇(bitertanol)、糠菌唑(bromoconazole)、环唑醇(cyproconazole)、醚唑(difenoconazole)、烯唑醇(diniconazole)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、己唑醇(hexaconazole)、烯菌灵(imazalil)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙氯灵(prochloraz)、丙硫菌唑(prothioconazole)、戊唑醇(tebuconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、氟菌唑(triflumizole)、戊叉唑菌(triticonazole)、粉唑醇(flutriafol),二羧酰亚胺类,例如异丙定(iprodione)、甲菌利(myclozolin)、杀菌利(procymidone)或烯菌酮(vinclozolin),二硫代氨基甲酸盐类,例如福美铁(ferbam)、代森钠(nabam)、代森锰(maneb)、代森锰锌(mancozeb)、威百亩(metam)、代森联(metiram)、甲基代森锌(propineb)、福代锌(polycarbamate)、福美双(thiram)、福美锌(ziram)或代森锌(zineb),杂环化合物类,例如敌菌灵(anilazine)、苯菌灵(benomyl)、啶酰菌胺(boscalid)、多菌灵(carbendazim)、萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin)、氰霜唑(cyazofamid)、棉隆(dazomet)、二噻农(dithianon)、唑酮菌(famoxadone)、咪唑菌酮(fenamidone)、异嘧菌醇(fenarimol)、麦穗宁(fuberidazole)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、稻瘟灵(isoprothiolane)、丙氧灭绣胺(mepronil)、氟苯嘧啶醇(nuarimol)、氟吡菌胺(picobenzamide)、噻菌灵(probenazole)、丙氧喹啉(proquinazid)、啶斑肟(pyrifenox)、咯喹酮(pyroquilon)、喹氧灵(quinoxyfen)、硅噻菌胺(silthiofam)、涕必灵(thiabendazole)、溴氟唑菌(thifluzamide)、甲基托布津(thiophanate-methyl)、噻酰菌胺(tiadinil)、三环唑(tricyclazole)或嗪氨灵(triforine),铜杀真菌剂,例如波尔多混合液(Bordeaux mixture)、乙酸铜、王铜、碱式硫酸铜,硝基苯基衍生物,例如乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)、异丙消(nitrophthal-isopropyl),苯基吡咯类,例如拌种咯(fenpiclonil)或氟菌(fludioxonil),硫,其他杀真菌剂,例如噻二唑素(acibenzolar-S-methyl)、苯噻菌胺(benthiavalicarb)、氯环丙酰胺(carpropamid)、百菌清(chlorothalonil)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、哒菌清(diclomezine)、双氯氰菌胺(diclocymet)、乙霉威(diethofencarb)、克瘟散(edifenphos)、噻唑菌胺(ethaboxam)、环酰菌胺(fenhexamid)、薯瘟锡(fentin acetate)、氰菌胺(fenoxanil)、嘧菌腙(ferimzone)、氟啶胺(fluazinam)、藻菌磷(fosetyl)、乙膦铝(fosetyl-aluminum)、异丙菌胺(iprovalicarb)、六氯苯(hexachlorobenzene)、苯菌酮(metrafenon)、戊菌隆(pencycuron)、百维灵(propamocarb)、四氯苯酞(phthalide)、甲基立枯磷(tolclofos-methyl)、五氯硝基苯(quintozene)、苯酰菌胺(zoxamide),嗜球果伞素类(strobilurins),例如腈嘧菌酯(azoxystrobin)、醚菌胺(dimoxystrobin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、肟醚菌胺(orysastrobin)、啶氧菌酯(picoxystrobin)或肟菌酯(trifloxystrobin),次磺酸衍生物,例如敌菌丹(captafol)、克菌丹(captan)、抑菌灵(dichlofluanid)、灭菌丹(folpet)或对甲抑菌灵(tolylfluanid),肉桂酰胺及类似物,例如烯酰吗啉(dimethomorph)、氟联苯菌(flumetover)或氟吗啉(flumorph)。
动物害虫,即节肢动物和线虫,植物,其中植物正在生长的土壤或水可通过本领域已知的任何施用方法与本发明式(I)化合物或含有它们的组合物接触。这里的“接触”包括直接接触(将化合物/组合物直接施用于动物害虫和/或植物上,通常施用于植物的叶、茎或根上)和间接接触(将化合物/组合物施用于动物害虫和/或植物的场所)。
此外,可通过使目标动物害虫、其食物源、栖息地、繁殖地或其场所与杀虫有效量的式(I)化合物接触而防治动物害虫。因此,施用可在场所、生长中的作物或已收获的作物被害虫侵染之前或之后进行。
“场所”是指其中害虫或寄生虫生长或可生长的栖息地、繁殖地、栽培植物、植物繁殖材料(如种子)、土壤、区域、材料或环境。
“杀虫有效量”通常指对生长获得可观察到的效果所需要活性成分的量,所述效果包括坏死、死亡、阻滞、预防和去除效果,破坏效果或减少目标生物体的出现和活动的效果。对于在本发明中使用的各种化合物/组合物,杀虫有效量可以变化。组合物的杀虫有效量也会根据主要条件如所需杀虫效果及持续时间、天气、目标物种、场所、施用方式等而变化。
式(I)化合物及其组合物可用于保护木质材料如树、木栅栏、枕木等和建筑物如房子、外屋、工厂,以及建筑材料、家具、皮革、纤维、乙烯基制品、电线和电缆等以防蚂蚁和/或白蚁,以及用于防治蚂蚁和白蚁不损害作物或人类(例如当害虫侵入房子和公共建筑时)。化合物不仅施用于周围土壤表面上或地板下土壤中以保护木制材料,而且它可施用于木料制品如地板下混凝土、凉亭立柱、梁、胶合板、家具等的表面,木质制品如碎料板、半木板等和乙烯基制品如涂覆电线、乙烯基片材,绝热材料如苯乙烯泡沫等。在对抗蚂蚁不损害作物或人类的施用的情况下,本发明蚂蚁防治剂施用于作物或周围土壤,或直接施用于蚂蚁的巢穴等。
式(I)化合物也可以预防方式施用至害虫预期出现的地方。
式(I)化合物还可通过使植物与杀虫有效量的式(I)化合物接触而用于保护生长中的植物防止害虫侵袭或侵染。这里的“接触”包括直接接触(将化合物/组合物直接施用于害虫和/或植物上,通常施用于植物的叶、茎或根上)和间接接触(将化合物/组合物施用于害虫和/或植物的场所)。
在土壤处理或施用于害虫栖息地或巢穴的情况下,活性成分的施用量为0.0001-500g/100m2,优选0.001-20g/100m2。
材料保护中的通常施用率例如为每平方米处理材料0.01-1000g活性化合物,理想的是每平方米0.1-50g活性化合物。
用于材料浸渍的杀虫组合物通常含有0.001-95重量%,优选0.1-45重量%,更优选1-25重量%至少一种驱除剂和/或杀虫剂。
用于诱饵组合物的活性成分的典型含量为0.001-15重量%,理想的是0.001-5重量%活性化合物。
用于喷雾组合物的活性成分含量为0.001-80重量%,优选0.01-50重量%,最优选0.01-15重量%。
用于处理作物植物的本发明活性成分的施用率可为每公顷0.1-4000g,理想的是每公顷25-600g,更理想的是每公顷50-500g。
在种子处理中,活性成分的施用率通常为0.1g至10kg/100kg种子,优选1g至5kg/100kg种子,尤其是1g至200g/100kg种子。
现在,本发明通过如下实施例进一步详细说明。
I.实验程序
通过适当改变起始化合物,将合成实施例中所示的方案用于得到其他式(I)化合物。
产物通过联合的高效液相色谱/质谱(HPLC/MS),通过CDCl3或d6-DMSO中的1H-NMR(400MHz)或通过它们的熔点表征。HPLC柱:RP-18柱(Chromolith Speed ROD,购自德国Merck KgaA)。洗脱液:以5∶95-95∶5比例的乙腈+0.1%三氟乙酸(TFA)/水,并且在40℃下进行5分钟。MS:四极(Quadrupol)电喷雾离子化,80V(正模式)。
I.1制备5-(2,4-二(三氟甲基)苯基)-1,1-二氧代-2-喹啉-4-基甲基-1,2-二氢-1-苯并[d]异噻唑-3-酮(5-(2,4-二(三氟甲基)苯基)-2-(喹啉-4-基甲基)邻磺酰苯甲酰亚胺)(化合物I.1)
I.1.1制备5-溴-2-氯磺酰基-苯甲酸甲基酯
向2-氨基-5-溴-苯甲酸甲基酯(25.0g,109mmol)在盐酸水溶液(10M,100ml)中的溶液中,在0℃下缓慢加入在水(25ml)中的NaNO2(8.3g,119mmol)溶液。在0℃下搅拌1小时之后,将所得反应混合物加入冷却至0℃的SO2在1,2-二氯乙烷(75ml)中的饱和溶液中,该溶液含有CuCl2(0.50g,3.7mmol)和苄基三甲基氯化铵(1.41g,7.6mmol)。在加料之后将反应混合物加热至50℃并维持1小时,冷却至环境温度并用CH2Cl2(250ml)萃取。将有机相用NaHCO3的饱和水溶液洗涤,并经Na2SO4干燥,过滤并真空浓缩。得到作为残留物的5-溴-2-氯-磺酰基-苯甲酸甲基酯,其量为3.6g。
I.1.2制备5-溴-2-(喹啉-4-基甲基)氨基磺酰基-苯甲酸甲基酯
将喹啉-4-基甲基胺(4.50g,24mmol),粗5-溴-2-氯-磺酰基-苯甲酸甲基酯(7.59g,24mmol,根据I.1.1制备)和三乙胺(4.04ml,29mmol)在CH2Cl2(100ml)中的溶液在环境温度下搅拌10小时。在所得反应混合物中加入水(100ml)。在相分离之后,将有机相经Na2SO4干燥,过滤并真空浓缩。将残留物通过柱色谱法提纯(梯度:环己烷/乙酸乙酯,100∶1-1∶9)得到5-溴-2-(喹啉-4-基甲基-氨基磺酰基-苯甲酸甲基酯(2.48g)。
I.1.3制备5-(2,4-二(三氟甲基)苯基)-1,1-二氧代-2-喹啉-4-基甲基-1,2-二氢-1-苯并[d]异噻唑-3-酮
将5-溴-2-(喹啉-4-基甲基)氨基磺酰基-苯甲酸甲基酯(0.50g,1.2mmol,根据I.1.2制备)和2,4-二(三氟甲基)苯基-硼酸(0.34g,1.3mmol)在乙腈(5ml)和水(2ml)中的溶液在固定化的二异丙基乙基胺(1.20g,4.08mmol,购自Novabiochem的PS-DIPEA)、二叔丁基四氟硼酸盐(0.017g,0.06mmol)和二(三苯基膦基)氯化钯-II(0.025g,0.04mmol)存在下回流8小时。过滤所得反应混合物,将所得固体用乙腈(10ml)漂洗并将所得滤液真空浓缩。将残留物通过柱色谱法提纯(梯度:环己烷/乙酸乙酯,90∶10-40∶60)得到5-(2,4-二(三氟甲基)苯基)-1,1-二氧代-2-喹啉-4-基甲基-1,2-二氢-1-苯并[d]异噻唑-3-酮(0.096g)。
I.2制备5-(2,4-二氟苯基)-1,1-二氧代-2-喹啉-4-基甲基-1,2-二氢-1-苯并[d]异噻唑-3-酮(5-(2,4-二氟苯基)-2-(喹啉-4-基甲基)邻磺酰苯甲酰亚胺)(化合物1.2)
I.2.1制备5-溴-1,1-二氧代-2-喹啉-4-基甲基-1,2-二氢-1-苯并[d]-异噻唑-3-酮
将5-溴-2-(喹啉-4-基甲基)氨基磺酰基-苯甲酸甲基酯(0.90g,2.1mmol,根据I.1.2制备)在冰醋酸(50ml)中的溶液在100℃下搅拌10小时。将冰醋酸真空除去。将残留物溶于乙酸乙酯中、用NaHCO3的饱和溶液洗涤,并经Na2SO4干燥,过滤并真空浓缩。如此得到5-溴-1,1-二氧代-2-喹啉-4-基甲基-1,2-二氢-1-苯并[d]异噻唑-3-酮,其量为0.70g。
I.2.2制备5-(2,4-二氟苯基)-1,1-二氧代-2-喹啉-4-基甲基-1,2-二氢-1-苯并[d]异噻唑-3-酮
将5-溴-1,1-二氧代-2-喹啉-4-基甲基-1,2-二氢-1-苯并[d]异噻唑-3-酮(0.300g,0.7mmol,根据I.2.1制备)和2,4-二氟苯基-硼酸(0.24g,2.4mmol)在乙腈(5ml)和水(2ml)中的溶液在三乙胺(0.240g,2.4mmol),二叔丁基四氟硼酸盐(0.010g,0.04mmol)和二(三苯基膦基)氯化钯-II(0.015g,0.02mmol)存在下回流3.5小时。将反应混合物真空浓缩。将残留物溶于冰醋酸中,加热至100℃并维持10小时。将反应混合物真空浓缩。将残留物溶于乙酸乙酯中,用NaHCO3的饱和水溶液洗涤,并经Na2SO4干燥,过滤并真空浓缩。将残留物通过柱色谱法提纯(梯度:环己烷/乙酸乙酯;99∶1-30∶70)得到5-(2,4-二氟苯基)-1,1-二氧代-2-喹啉-4-基甲基-1,2-二氢-1-苯并[d]异噻唑-3-酮(45mg)。
I.3制备5-(2,4-二氟苯基)-2-(2-甲氧基吡啶-4-基甲基)-1,1-二氧代-1,2-二氢苯并[d]异噻唑-3-叉基胺(-3-ylideneamine)(化合物I.3)
I.3.1制备5-(2,4-二氟苯基)苯并[d]异噻唑
将5-溴苯并[d]异噻唑(5.0g,23mmol,根据EP454621制备),2,4-二氟苯基硼酸(5.4g,34mmol)、二叔丁基四氟硼酸盐(0.9g)、二(三苯基膦)氯化钯(II)(1.3g)和三乙胺(14ml)在乙腈(40ml)和水(20ml)中的溶液加热至75℃并维持2小时。通过蒸馏除去溶剂,加入水并用二氯甲烷萃取产物。将有机层经Na2SO4干燥,过滤并真空浓缩,得到粗5-(2,4-二氟苯基)苯并[d]异噻唑(5.8g)。
I.3.2制备2′,4′-二氟-4-巯基联苯-3-基甲腈
在室温下,向粗5-(2,4-二氟苯基)苯并[d]异噻唑(5.8g,23mmol,根据实施例I.3.1制备)在乙腈(100ml)中的溶液中加入甲醇钠(2.9g,53mmol)。将混合物加热回流2小时,然后通过蒸馏除去溶剂,加入水并用HCl水溶液(浓度为10%)酸化混合物。用二氯甲烷萃取反应混合物,将有机层经Na2SO4干燥,过滤并真空浓缩。将残留物溶于甲基叔丁基醚并加入甲醇钠(在甲醇中,浓度为30%)。将所得固体沉淀通过过滤收集、用甲基叔丁基醚洗涤并真空干燥。将干燥的固体沉淀溶于HCl水溶液(浓度为10%)中并用二氯甲烷萃取。有机层经Na2SO4干燥,过滤并真空浓缩得到粗2′,4′-二氟-4-巯基联苯-3-基甲腈(4.5g)。
I.3.3制备3-氰基-2′,4′-二氟联苯-4-磺酰氯
将氯气通过粗2′,4′-二氟-4-巯基-联苯-3-基甲腈(4.5g,18mmol,根据I.3.2制备)在乙酸(45ml)和水(3ml)中的溶液,直至反应完全。加入水,用二氯甲烷萃取产物。有机层经Na2SO4干燥,过滤并真空浓缩。将残留物通过柱色谱法提纯(洗脱液:甲苯)得到3-氰基-2′,4′-二氟联苯-4-磺酰氯(4.6g)。
I.3.4 3-氰基-2′,4′-二氟联苯-4-磺酸N-(2-甲氧基吡啶-4-基甲基)酰胺
在室温下,向(2-甲氧基吡啶-4-基)-甲基胺(705mg,5.1mmol)、吡啶(1.7ml)和二甲基氨基吡啶(12mg)在四氢呋喃(30ml)中的溶液中加入3-氰基-2′,4′-二氟联苯-4-磺酰氯(1.46g,4.6mmol,根据实施例I.3.3制备)在四氢呋喃(20ml)中的溶液,并将混合物搅拌48小时。加入水并用二氯甲烷萃取产物。将有机层用HCl水溶液(浓度为10%)和碳酸钠水溶液(浓度为10%)洗涤。有机层经Na2SO4干燥,过滤并真空浓缩,得到3-氰基-2′,4′-二氟联苯-4-磺酸N-(2-甲氧基-吡啶-4-基甲基)酰胺(1.7g)。
I.3.5制备5-(2,4-二氟苯基)-2-(2-甲氧基吡啶-4-基甲基)-1,1-二氧代-1,2-二氢-苯并[d]异噻唑-3-叉基胺
向3-氰基-2′,4′-二氟联苯-4-磺酸N-(2-甲氧基吡啶-4-基甲基)酰胺(1.0g,2.4mmol,根据实施例I.3.4制备)在甲苯(100ml)中的溶液中加入碳酸钠(0.77g,7.2mmol)在水(50ml)中的溶液。将混合物在室温下搅拌24小时。将有机相分离并用乙酸乙酯萃取水相。将合并的有机相经Na2SO4干燥,过滤并真空浓缩,得到5-(2,4-二氟-苯基)-2-(2-甲氧基吡啶-4-基甲基)-1,1-二氧代-1,2-二氢-苯并[d]异噻唑-3-叉基胺(0.9g;熔点=173℃;HPLC/MS:tr=2.9min,(m/z)=416[M+H]+)。
I.4制备5-(2,4-二氟苯基)-2-(2-甲氧基吡啶-4-基甲基)-1,1-二氧代-1,2-二氢-苯并[d]异噻唑-3-酮(化合物I.4)
向5-(2,4-二氟苯基)-2-(2-甲氧基吡啶-4-基甲基)-1,1-二氧代-1,2-二氢苯并[d]异噻唑-3-叉基胺(0.6g,1.4mmol,根据实施例I.3.5制备)在二烷(30ml)中的溶液中加入HCl水溶液(浓度为10%,5ml)。将溶液在室温下搅拌5小时。加入水并用二氯甲烷萃取产物。有机层经Na2SO4干燥,过滤并真空浓缩。将残留物通过柱色谱法提纯(洗脱液:环己烷/乙酸乙酯)得到5-(2,4-二氟苯基)-2-(2-甲氧基吡啶-4-基甲基)-1,1-二氧代-1,2-二氢-苯并[d]异噻唑-3-酮(0.73mmol,300mg)。
1H-NMR(CDCl3):=3.92(s,3H),4.86(s,2H),6.84(s,1H),7.01(m,3H),7.44(m,1H),8.02(s,2H),8.18ppm(m,2H)。
根据上述方法制备了如下式(I.A)的磺酰胺化合物,即其中m为0,X为O,Y为CH和Z为化学键的式(I)化合物:
其中R1,R2,R3和R5具有下表I中所给含义(化合物I.5-I.48)。
表I.
mp=熔点
RT=保留时间
Mw=分子量
II.对昆虫和蜘蛛的活性
通用条件
如果没有另外描述,如下制备测试溶液:将活性化合物以所需浓度溶于蒸馏水∶丙酮的1∶1体积比的混合物中。测试溶液在使用当天制备。测试溶液通常以1000、500、300、100和30ppm(重量/体积)的浓度制备。
II.1墨西哥棉铃象(Boll weevil/Anthonomus grandis)
为了评价对墨西哥棉铃象的防治,测试单元由24孔微滴定板组成,该微滴定板含有昆虫食物和20-30个墨西哥棉铃象虫卵。使用含有75%(体积∶体积)水和25%(体积∶体积)DMSO的溶液配制化合物。使用定制的微型雾化器以20μl将不同浓度的配制化合物喷雾在昆虫食物上,重复两次。在施用之后,将微滴定板在约23±1℃和约50±5%相对湿度下培养5天。然后目测评价虫卵和幼虫的死亡率。
在该测试中,与未处理对照相比,化合物I.9、I.12、I.17、I.18、I.25-I.28、I.33-I.35和I.38在2500ppm下显示超过75%的死亡率。
II.2地中海实蝇(Mediterranean fruitfly/Ceratitis capitata)
为了评价对地中海实蝇的防治,测试单元由微滴定板组成,该微滴定板含有昆虫食物和50-80个地中海实蝇虫卵。使用含有75%(体积∶体积)水和25%(体积∶体积)DMSO的溶液配制化合物。使用定制的微型雾化器以5μl将不同浓度的配制化合物喷雾在昆虫食物上,重复两次。在施用之后,将微滴定板在约28±1℃和约80±5%相对湿度下培养5天。然后目测评价虫卵和幼虫死亡率。
在该测试中,与未处理对照相比,化合物I.9、I.12、I.17、I.25、I.27、I.33-I.35和I.38在2500ppm下显示超过75%的死亡率。
II.3烟芽夜蛾(Tobacco budworm/Heliothis virescens)
为了评价对烟芽夜蛾的防治,测试单元由96孔微滴定板组成,该微滴定板含有昆虫食物和15-25个烟芽夜蛾虫卵。
使用含有75%(体积∶体积)水和25%(体积∶体积)DMSO的溶液配制化合物。使用定制的微型雾化器以10μl将不同浓度的配制化合物喷雾在昆虫食物上,重复两次。在施用之后,将微滴定板在约28±1℃和约80±5%相对湿度下培养5天。然后目测评价虫卵和幼虫死亡率。
在该测试中,与未处理对照相比,化合物I.9、I.12、I.17、I.18、I.26、I.28、I.33-I.35和I.38在2500ppm下显示超过75%的死亡率。
II.4巢菜修尾蚜(Vetch aphid/Megoura viciae)
为了评价通过接触或内吸措施对巢菜修尾蚜的防治,测试单元由含有蚕豆叶片的24孔微滴定板组成。使用含有75%(体积∶体积)水和25%(体积∶体积)DMSO的溶液配制化合物。使用定制的微型雾化器以2.5μl将不同浓度的配制化合物喷雾在叶片上,重复两次。在施用之后,将叶片风干并将5-8个巢菜修尾蚜成虫置于微滴定板孔内的叶片上。然后使蚜虫在处理的叶片上吮吸并在约23±1℃和约50±5%相对湿度下培养5天。然后目测评价蚜虫死亡率和生殖力。
在该测试中,与未处理对照相比,化合物I.9、I.12、I.17、I.18、I.25、I.27、I.34、I.35和I.38在2500ppm下显示超过75%的死亡率。II.5桃蚜(Myzus persicae)
为了评价通过内吸措施对桃蚜的防治,测试单元由96孔微滴定板组成,该微滴定板含有在人工膜下的液体人工食物。使用含有75%(体积∶体积)水和25%(体积∶体积)DMSO的溶液配制化合物。使用定制的移液管将不同浓度的配制化合物移入桃蚜食物中,重复2次。在施用之后,将5-8只桃蚜成虫置于微滴定板孔内的人工膜上。然后使蚜虫在处理的蚜虫食物上吮吸并在约23±1℃和约50±5%相对湿度下培养3天。然后目测评价蚜虫死亡率和生殖力。
在该测试中,与未处理对照相比,化合物I.9、I.12、I.17、I.18、I.26、I.27、I.34、I.35和I.38在2500ppm下显示超过75%的死亡率。
II.6兰花蓟马(Orchid thrips/Dichromothrips corbetti)
用于生物测试的兰花蓟马成虫得自在实验室条件下连续培养的群体。为了测试,在1∶1(体积∶体积)的丙酮∶水混合物加上0.01%(体积∶体积)表面活性剂中将测试化合物稀释至浓度为300ppm(化合物重量:稀释剂体积)。
使用花浸渍技术评价各化合物的蓟马效力。将塑料皮氏培养皿用作测试平台。将整个的各兰花花朵的所有花瓣浸没入处理溶液中并使其干燥。将处理的花朵与10-15只蓟马成虫一起置于各皮氏培养皿中。然后用盖子覆盖皮氏培养皿。在生物测试期间,将所有测试平台保持在持续光照和约28℃的温度下。在4天后,对各花朵和沿着各皮氏培养皿的内壁计算活的蓟马数目。由处理前的蓟马数目推算蓟马死亡率水平。
在该测试中,与未处理对照相比,化合物I.8-I.13、I.15、I.19、I.20、I.22、I.23、I.27和I.31在300ppm下显示超过75%的死亡率。
II.7豇豆蚜虫(Cowpea aphid/Aphis craccivora)
将活性化合物以所需浓度溶解在1∶1(体积∶体积)的蒸馏水∶丙酮混合物中。将测试溶液在使用当天制备。
在记录害虫数量后,对用约100-150只不同阶段的蚜虫侵入的盆栽豇豆植物进行喷雾。在24、72和120小时之后,记录减少的数量。
在该测试中,与未处理对照相比,化合物I.8-I.13、I.15、I.17-I.20、I.22-I.27、I.29和I.31在300ppm下显示超过75%的死亡率。
II.8棉蚜(Cotton aphid/Aphis gossypii)I
将活性化合物配制在50∶50(体积∶体积)的丙酮∶水和100ppm KineticTM表面活性剂中。
通过在各子叶顶部放置来自主群落的重度侵染的叶而侵染子叶阶段的棉花植物(每盆一颗植物)。使蚜虫经一整夜转移至寄主植物,除去用于转移蚜虫的叶。将子叶浸没在测试溶液中并使其干燥。在5天后,计算死亡率。
在该测试中,与未处理对照相比,化合物I.5-I.20、I.22-I.25、I.28和I.31在300ppm下显示超过75%的死亡率。
II.9银叶粉虱(Silverleaf whitefly/bemisia argentifolii)
将活性化合物配制在50∶50(体积∶体积)的丙酮∶水和100ppm KineticTM表面活性剂中。
使选取的棉花植物生长到子叶阶段(每盆一株)。将子叶浸入测试溶液中以完全覆盖叶面并放于良好通风的区域以进行干燥。将具有处理秧苗的各盆放入塑料杯中并引入10-12只银叶粉虱成虫(约3-5天龄)。使用呼吸器和连接于防渗移液管尖端的管收集昆虫。然后将含有收集的昆虫的该尖端轻轻地插入含有处理植物的土壤中,使昆虫爬出该尖端而到达叶面上取食。将杯子用可再用的筛盖覆盖。将测试植物在保持室中于约25℃和约20-40%相对湿度下保持3天,并避免直接暴露于荧光(24小时光照期)以防止在杯子内蓄积热。在处理植物3天后评价死亡率。
在该测试中,与未处理对照相比,化合物I.22-I.24和I.28在300ppm下显示超过75%的死亡率。
II.10马铃薯叶甲(Leptinotarsa decemlineata)
将土豆植物用于生物测试。将切离的植物叶浸没入活性化合物的1∶1(体积∶体积)丙酮/水稀释液中。在叶干燥之后,将它们各自置于皮氏培养皿底部的含水潮湿滤纸上。将各培养皿用5-7只幼虫侵染并用盖子覆盖。将各处理液重复4次。将测试培养皿保持在约27℃和约60%的湿度下。在处理施加5天后,评估各培养皿中的活的和病的幼虫数目,并计算死亡率百分数。
在该测试中,与未处理对照相比,化合物I.6-I.8在300ppm下显示超过75%的死亡率。
II.11桃蚜(Myzus persicae)
将活性化合物配制在50∶50(体积∶体积)的丙酮∶水和100ppm KineticTM表面活性剂中。
将第2对叶阶段的胡椒植物(品种″California Wonder″)通过将侵染的叶片部分放置在试验植物顶部而用约40只实验室饲养的蚜虫侵染。24小时后移除该叶片部分。将完整植物的叶子浸泡在测化合物的梯度溶液中并使其干燥。将测试植物在约25℃和约20-40%相对湿度下保持在荧光灯下(24小时的光周期)。5天后,相对于对照植物上的死亡率测定处理植物上的蚜虫死亡率。
在该测试中,与未处理对照相比,化合物I.8-I.17、I.20和I.22-I.24在300ppm下显示超过75%的死亡率。
II.12二点黑尾叶蝉(Rice green leafhopper/nephotettix virescens)
将稻秧苗在喷雾之前24小时清洁并洗涤。将活性化合物配制在50∶50(体积∶体积)的丙酮∶水中,并加入0.1%(体积∶体积)表面活性剂(EL620)。将盆栽稻秧苗用5ml测试溶液喷雾、风干、置于笼中并用10只成虫接种。将处理的稻植物保持在约28-29℃和约50-60%的相对湿度下。在72小时之后记录死亡率百分数。
在该测试中,与未处理对照相比,化合物I.19和I.22-I.24在300ppm下显示超过75%的死亡率。
II.13褐飞虱(nilaparvata lugens)
在喷雾之前24小时,将稻秧苗清洁并洗涤。将活性化合物配制在50∶50(体积∶体积)的丙酮∶水中,并加入0.1%(体积∶体积)表面活性剂(EL620)。将盆栽稻秧苗用5ml试验溶液喷雾,风干,置于笼中并用10只成虫接种。将处理的稻植物保持在约28-29℃和约50-60%的相对湿度下。72小时后记录死亡率百分数。
在该测试中,与未处理对照相比,化合物I.9、I.11、I.13、I.15、I.22和I.23在300ppm下显示超过75%的死亡率。
II.14菜蛾(Plutella xylostella)
将活性化合物以所需浓度溶解在1∶1(体积∶体积)的蒸馏水∶丙酮混合物中。将测试溶液在使用当天制备。将大白菜叶浸入测试溶液中并风干。将处理的叶置于衬有潮湿滤纸的皮氏培养皿中。在处理24、72和120小时之后记录死亡率。还观察处理幼虫的行为,如活动减退和活动过度,蛹茧的存在以及死亡幼虫的特征。
在该测试中,与未处理对照相比,化合物I.8-I.13、I.15、I.19、I.20、I.22-I.24、I.27和I.31在300ppm下显示超过75%的死亡率。
II.15南方灰翅夜蛾(Southern armyworm/Spodoptera eridania,2龄幼虫)
将活性化合物配制在50∶50(体积∶体积)的丙酮∶水和100ppm KineticTM表面活性剂中。
将棉豆(Sieva lima bean)的第一对真叶浸没在测试溶液中并使其干燥。然后将叶放在塑料的穿孔拉链封闭袋中然后加入10只2龄幼虫。在4天时,观察死亡率和降低的进食。
在该测试中,与未处理对照相比,化合物I.6-I.16、I.19、I.21-I.24和I.31在300ppm下显示超过75%的死亡率。
II.16叶螨(tetranychus属)
将活性化合物以所需浓度溶于1∶1(体积∶体积)的蒸馏水∶丙酮混合物中。将测试溶液在使用当天制备。
在记录害虫群口之后,对侵入约50只各种阶段的螨虫的盆栽棉花植物喷雾。在24、72和120小时后评价群口减少(或增加)。
在该测试中,与未处理对照相比,化合物I.8、I.10、I.11、I.15、I.19、I.23和I.24在300ppm下显示超过75%的死亡率。
III.对啮齿动物的活性
在急性口服鼠毒性研究中,测试了一些本发明的代表性化合物。
在这些研究中,通过口服灌胃将测试物质一次给药于成年母鼠。化合物以1%b.w.的悬浮液或以在1%羧甲基纤维素水溶液中的化合物给药。在每次研究中,使用3只鼠。用100mg/kg bw的单次剂量处理动物。对动物观察包括给药14天后死亡的临床症状,以鉴别可能的延迟毒性。在14天的观察期之后,将动物处死、解剖并检查总的病理。结果汇集在表II。
表II:
*处理后的时间
**根据表I
显然,这些化合物在它们诱发的毒性临床症状方面有所不同,然而,在紧邻处理后或在处理后的首个24小时或更长的时间内没有观察到这些临床症状。在单次口服剂量给药后的该延迟毒性以及相伴的没有立即的临床症状使得这些化合物适合用作灭鼠剂。
Claims (29)
1.式(I)的磺酰胺化合物及其N-氧化物和盐:
其中
R1选自氢、卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-C7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6烷硫基、C2-C6链烯硫基、C2-C6炔硫基、C1-C6卤代烷基和C1-C6卤代烷氧基;
R2和R3独立地选自氢、卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-C7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6烷硫基、C2-C6链烯硫基、C2-C6炔硫基、C1-C6卤代烷基和C1-C6卤代烷氧基;或
R2与R3以及与连接它们的碳原子一起形成稠合的5或6元碳环或稠合的5或6元杂环,该杂环含有1或2个选自O、N和S的杂原子作为环成员,其中各稠合的碳环或杂环未被取代或带有1、2、3或4个相互独立地选自如下的取代基:卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-C7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6烷硫基、C2-C6链烯硫基、C2-C6炔硫基、C1-C6卤代烷基和C1-C6卤代烷氧基;
R4选自卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6卤代烷硫基、C1-C6卤代烷基亚磺酰基和C1-C6卤代烷基磺酰基;
n为0、1、2或3;
R5选自苯基和5或6元杂环Het,其含有1、2或3个选自O、N和S的杂原子作为环成员,其中苯基和Het未被取代或带有1、2、3或4个相互独立地选自如下的取代基:卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、C1-C6卤代烷基、C1-C6卤代烷氧基、C1-C6卤代烷硫基、C1-C6卤代烷基亚磺酰基和C1-C6卤代烷基磺酰基;
X为O或NRx,其中Rx选自氢、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C1-C6烷氧基、C2-C6链烯氧基、C1-C6烷基羰基和C1-C6烷基羰氧基;
Y为N或C(Ry),其中Ry选自氢、卤素、氰基、C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C3-7环烷基-C1-C4烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6烷硫基、C2-C6链烯硫基、C2-C6炔硫基、C1-C6卤代烷基和C1-C6卤代烷氧基;和
Z为化学键、O或N(Rz),其中Rz选自C1-C6烷基、C2-C6链烯基、C2-C6炔基、C3-C7环烷基、C1-C6烷氧基、C2-C6链烯氧基、C1-C6烷基羰基和C1-C6烷基羰氧基。
2.根据权利要求1的式(I)磺酰胺化合物,其中R1选自氢、卤素、C1-C6烷基、C3-C7环烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6卤代烷基和C1-C6卤代烷氧基。
3.根据前述权利要求中任一项的式(I)磺酰胺化合物,其中R2和R3独立地选自氢、卤素、C1-C6烷基、C3-C7环烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6卤代烷基和C1-C6卤代烷氧基。
4.根据权利要求1-3中任一项的式(I)磺酰胺化合物,其中R2与R3以及与连接它们的碳原子一起形成稠合的5或6元碳环或稠合的5或6元杂环,其含有1个选自O、N和S的杂原子作为环成员,其中各稠合的碳环或杂环未被取代或带有1或2个相互独立地选自如下的取代基:卤素、氰基、C1-C6烷基、C3-C7环烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6卤代烷基和C1-C6卤代烷氧基。
5.根据前述权利要求中任一项的式(I)磺酰胺化合物,其中Y为C(Ry)且Ry选自氢、卤素、C1-C6烷基、C3-C7环烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6卤代烷基和C1-C6卤代烷氧基。
6.根据前述权利要求中任一项的式(I)磺酰胺化合物,其中X为O或NH。
7.根据前述权利要求中任一项的式(I)磺酰胺化合物,其中R4选自卤素、C1-C4烷基和C1-C4卤代烷基。
8.根据前述权利要求中任一项的式(I)磺酰胺化合物,其中n为0。
9.根据前述权利要求中任一项的式(I)磺酰胺化合物,其中Z为化学键或O。
10.根据前述权利要求中任一项的式(I)磺酰胺化合物,其中R5选自未被取代或带有1或2个相互独立地选自如下的取代基的苯基:卤素、C1-C4烷基、C3-C7环烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基和C1-C4卤代烷基磺酰基。
11.根据权利要求10的式(I)磺酰胺化合物,其中Z为化学键。
12.根据权利要求10或11的式(I)磺酰胺化合物,其中R5选自带有1个取代基的苯基且该取代基在相对于键接位置的2位或4位,或选自带有2个取代基的苯基且这些取代基在相对于键接位置2和4位或2和5位。
13.根据权利要求1-9中任一项的式(I)磺酰胺化合物,其中R5选自5或6元杂环Het,其含有1、2或3个选自O、N和S的杂原子作为环成员,其中Het未被取代或带有1或2个相互独立地选自如下的取代基:卤素、C1-C4烷基、C3-C7环烷基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4卤代烷基、C1-C4卤代烷氧基、C1-C4卤代烷硫基、C1-C4卤代烷基亚磺酰基和C1-C4卤代烷基磺酰基。
15.根据权利要求13或14的式(I)磺酰胺化合物,其中Z为O。
20.一种含有至少一种如权利要求1-15中任一项所定义的式(I)磺酰胺化合物、其N-氧化物和/或盐与至少一种液体或固体载体的组合物。
21.一种防治动物害虫的方法,该方法包括用如权利要求1-15中任一项所定义的式(I)磺酰胺化合物、其N-氧化物和/或盐或如权利要求20所定义的组合物处理害虫、其食物源、其栖息地或其繁殖地或其中害虫生长或可生长的植物、植物繁殖材料、土壤、区域、材料或环境,或需防止害虫侵袭或侵染的材料、植物、植物繁殖材料、土壤、表面或空间。
22.如权利要求21所述的方法,其中用于保护植物繁殖材料和/或由其长出的植物,该方法包括用如权利要求1-15中任一项所定义的式(I)磺酰胺化合物、其N-氧化物和/或可农用盐或如权利要求20所定义的农业组合物处理植物繁殖材料。
23.如权利要求21所述的方法,其中所述动物害虫选自无脊椎动物害虫。
24.如权利要求21所述的方法,其中所述动物害虫选自啮齿动物害虫。
25.包含至少一种如权利要求1-15中任一项所定义的式(I)磺酰胺化合物、其N-氧化物和/或可农用盐的植物繁殖材料。
26.一种处理或保护动物防止寄生虫侵袭或侵染的方法,该方法包括将如权利要求1-15中任一项所定义的式(I)化合物、其N-氧化物和/或可兽用盐或如权利要求20所定义的组合物给药或施用于动物或其栖息地。
27.如权利要求1-15中任一项所定义的式(I)磺酰胺化合物、其N-氧化物和/或可兽用盐或如权利要求20所定义的组合物在防治动物害虫中的用途。
28.如权利要求27所述的用途,其中所述动物害虫选自无脊椎动物害虫。
29.如权利要求27所述的用途,其中所述动物害虫选自啮齿动物害虫。
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CN102870783A (zh) * | 2012-09-11 | 2013-01-16 | 江苏正泰医药化工有限公司 | 一种灭鼠药 |
CN103619818A (zh) * | 2011-06-20 | 2014-03-05 | 纳幕尔杜邦公司 | 用于治疗蠕虫感染的杂环化合物 |
CN113598163A (zh) * | 2021-09-10 | 2021-11-05 | 姜兆伟 | 一种防儿童误食的蚊香液及原料苦精的应用 |
CN114133345A (zh) * | 2020-12-17 | 2022-03-04 | 顺毅宜昌化工有限公司 | 一种2-氯磺酰基-4-甲磺酰胺甲基苯甲酸甲酯的制备方法 |
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EP3273247A1 (en) | 2010-06-10 | 2018-01-24 | Metanomics Health GmbH | Methods for the diagnosis of liver diseases |
US8829026B2 (en) | 2010-10-01 | 2014-09-09 | Raqualia Pharma Inc. | Sulfamoyl benzoic acid heterobicyclic derivatives as TRPM8 antagonists |
US20140275502A1 (en) * | 2013-03-13 | 2014-09-18 | Dow Agrosciences Llc | Process for the preparation of certain triaryl rhamnose carbamates |
US20140275503A1 (en) * | 2013-03-13 | 2014-09-18 | Dow Agrosciences Llc | Process for the preparation of certain triaryl rhamnose carbamates |
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CN103619818A (zh) * | 2011-06-20 | 2014-03-05 | 纳幕尔杜邦公司 | 用于治疗蠕虫感染的杂环化合物 |
CN102870783A (zh) * | 2012-09-11 | 2013-01-16 | 江苏正泰医药化工有限公司 | 一种灭鼠药 |
CN114133345A (zh) * | 2020-12-17 | 2022-03-04 | 顺毅宜昌化工有限公司 | 一种2-氯磺酰基-4-甲磺酰胺甲基苯甲酸甲酯的制备方法 |
CN113598163A (zh) * | 2021-09-10 | 2021-11-05 | 姜兆伟 | 一种防儿童误食的蚊香液及原料苦精的应用 |
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