CN101184737B - 用于对抗动物害虫的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物 - Google Patents
用于对抗动物害虫的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物 Download PDFInfo
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- CN101184737B CN101184737B CN200680018407.0A CN200680018407A CN101184737B CN 101184737 B CN101184737 B CN 101184737B CN 200680018407 A CN200680018407 A CN 200680018407A CN 101184737 B CN101184737 B CN 101184737B
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- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
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- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
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- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
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- 229910001428 transition metal ion Inorganic materials 0.000 description 1
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Abstract
本发明涉及式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物及其可农盐,其中A为式A1或A2的基团。本发明还涉及包含至少一种化合物I和/或其盐的农用组合物和种子,以及一种对抗动物害虫的方法、一种保护作物以防动物害虫侵袭或侵染的方法、一种保护非活体材料以防动物害虫侵袭或侵染的方法、一种保护种子以防动物害虫并保护秧苗的根和芽以防动物害虫的方法,其中施用杀虫有效量的至少一种1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物I和/或其盐。
Description
本发明涉及用于对抗动物害虫的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物。本发明还涉及对抗动物害虫的方法以及对抗动物害虫的农用组合物。
动物害虫,尤其是昆虫、蜘蛛和线虫破坏生长和收获的作物并侵袭木质住宅和商业结构体,对食品供应和财产造成大的经济损失。尽管已知许多杀虫试剂,但由于目标害虫能够对所述试剂产生抗性,因此仍然需要对抗昆虫、蜘蛛和线虫的新试剂。
然而,这些化合物的活性或活性谱的宽度有限。
因此,本发明的目的是提供具有良好杀虫活性并对大量不同动物害虫,尤其是难以控制的昆虫、蜘蛛和线虫具有宽活性谱的化合物。
已经发现这些目的可以由式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物及其可农用盐实现:
其中A为式A1或A2的基团:
并且其中
m为0、1、2、3、4或5;
n为0、1、2、3、4或5;
R1、R2各自独立地为
-卤素、OH、SH、NH2、SO3H、COOH、氰基、硝基、甲酰基,
-C1-C6烷基、C1-C6烷氧基、C1-C6烷基氨基、二(C1-C6烷基)氨基、C1-C8烷硫基、C2-C6链烯基、C2-C6链烯氧基、C2-C6链烯基氨基、C2-C6链烯硫基、C2-C6炔基、C2-C6炔氧基、C2-C6炔基氨基、C2-C6炔硫基、C1-C6烷基磺酰基、C1-C6烷基亚磺酰基(sulfoxyl)、C2-C6链烯基磺酰基、C2-C6炔基磺酰基、(C1-C6烷基)羰基、(C2-C6链烯基)羰基、(C2-C6炔基)羰基、(C1-C6烷氧基)羰基、(C2-C6链烯氧基)羰基、(C2-C6炔氧基)羰基、(C1-C6烷基)羰基氧基、(C2-C6链烯基)羰基氧基或(C2-C6炔基)羰基氧基,
其中上述基团的脂族基团中的碳原子可以带有1、2或3个相互独立地选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任何组合;
-C(O)NRaRb、(SO2)NRaRb、基团Y-Ar或基团Y-Cy,其中
Y为单键、氧、硫、C1-C6链烷二基(alkandiyl)或C1-C6链烷二基氧基(alkandiyloxy);
Ar为苯基、萘基或含有1、2、3或4个选自2个氧、2个硫和3个氮原子的杂原子作为环成员的单环或双环5-10员杂芳族环,其中Ar未被取代或可以带有1-5个相互独立地选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任何组合;和
Cy为C3-C12环烷基,其未被取代或被1-5个相互独立地选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团取代;
以及其中与苯基环的相邻碳原子连接的两个基团R1或两个基团R2可以与所述碳原子一起形成稠合苯环、稠合的饱和或部分不饱和5、6或7员碳环或稠合的5、6或7员杂环,该杂环含有1、2、3或4个选自2个氧、2个硫和3个氮原子的杂原子作为环成员,并且其中该稠合环未被取代或可以带有1、2、3或4个相互独立地选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团;
R3、R4各自独立地为
-氢、C1-C6烷基、C1-C6卤代烷基或C3-C6环烷基,其中后3个基团中的碳原子可以带有1、2或3个相互独立地选自氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任何组合,或
-苯基或苄基,各自未被取代或被1-5个相互独立地选自5个卤素、3个C1-C6烷基、3个C1-C6卤代烷基、3个C1-C6烷硫基、3个C1-C6卤代烷硫基、3个C1-C6烷氧基和3个C1-C6卤代烷氧基的基团取代;
R5、R6各自独立地为
-氢、氰基、硝基、甲酰基,
-C1-C6烷基、(C1-C6烷基)羰基、(C1-C6烷氧基)羰基、(C1-C6烷硫基)羰基或(C1-C6烷氧基)亚甲基,其中上述基团的脂族基团中的碳原子可以带有1、2或3个相互独立地选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任何组合,或
-C(O)NRcRd、(SO2)NRcRd、苯基、苯氧基或苄基,后提到的3个基团各自可以未被取代或被1-5个相互独立地选自5个卤素、3个C1-C6烷基、3个C1-C6卤代烷基、3个C1-C6烷硫基、3个C1-C6卤代烷硫基、3个C1-C6烷氧基和3个C1-C6卤代烷氧基的基团取代;
R7为氢、氰基、硝基、甲酰基、C1-C6烷基、(C1-C6烷基)羰基、(C1-C6烷氧基)羰基、(C1-C6烷硫基)羰基或(C1-C6烷氧基)亚甲基,其中上述基团的脂族基团中的碳原子可以带有1、2或3个相互独立地选自卤素、氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任何组合,或
R7为C(O)NReRf或(SO2)NReRf、苯基、苯氧基或苄基,后提到的3个基团各自可以未被取代或被1-5个相互独立地选自5个卤素、3个C1-C6烷基、3个C1-C6卤代烷基、3个C1-C6烷硫基、3个C1-C6卤代烷硫基、3个C1-C6烷氧基和3个C1-C6卤代烷氧基的基团取代;
R8、R9、R10、R11各自独立地为氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基氨基、C1-C6烷氧基或C3-C6环烷基,其中后5个基团的碳原子可以带有1、2或3个相互独立地选自氰基、硝基、羟基、巯基、氨基、羧基、C1-C6烷基、C1-C6烷氧基、C2-C6链烯氧基、C2-C6炔氧基、C1-C6卤代烷氧基和C1-C6烷硫基的基团的任何组合;
Ra、Rb、Rc、Rd、Re、Rf相互独立地为氢、C1-C6烷基、C1-C6卤代烷基、C2-C6链烯基或C2-C6炔基。
因此,本发明涉及式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物及其可农用盐。这些化合物具有高杀虫活性且对宽范围的动物害虫,尤其是昆虫、蜘蛛和线虫有活性。
本发明还涉及
-一种对抗动物害虫,尤其是昆虫、蜘蛛和线虫的方法,包括使动物害虫,其栖息地,繁殖地,食物供应源,动物害虫生长或可能生长于其中的植物、种子、土壤、区域、材料或环境,或需要防止动物害虫,尤其是昆虫、蜘蛛或线虫侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的至少一种式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或至少一种其可农用盐接触,
-一种保护种子以防动物害虫以及保护秧苗的根和芽以防动物害虫的方法,以及
-包含式I化合物或I的可农用盐的种子。
此外,本发明提供了一种保护作物以免动物害虫,尤其是昆虫、蜘蛛或线虫侵袭或侵染的方法,包括使作物与杀虫有效量的至少一种式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或至少一种其盐接触。
此外,本发明涉及农用组合物,其优选呈可直接喷雾溶液、乳液、糊、油分散体、粉末、撒播用材料、粉剂形式,或呈颗粒形式,其包含至少一种如上所定义的式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物或其盐,其混有一种或多种可农用惰性固体或液体载体以及需要的话至少一种表面活性剂。
式I化合物可以具有一个或多个手性中心,此时它们以立体异构体如对映体或非对映体的混合物存在。本发明提供了纯立体异构体如纯对映体或非对映体及其混合物。式I化合物还可以不同互变异构体形式存在。本发明包括单一互变异构体(若可分离的话),以及互变异构体混合物。
适于本发明用途的式I化合物的盐尤其为可农用盐。它们可以常规方法形成,例如若式I化合物具有碱性官能团则通过使该化合物与所述阴离子的酸反应,或使式I的酸性化合物与合适的碱反应。
合适的可农用盐尤其是其阳离子和阴离子分别对本发明化合物的作用没有任何不利影响的那些阳离子的盐或那些酸的酸加成盐。合适的阳离子尤其是碱金属离子,优选锂、钠和钾离子;碱土金属离子,优选钙、镁和钡离子;过渡金属离子,优选锰、铜、锌和铁离子;还有铵离子(NH4 +)和其中1-4个氢原子被C1-C4烷基、C1-C4羟基烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、羟基-C1-C4烷氧基-C1-C4烷基、苯基和/或苄基代替的取代铵离子。取代铵离子的实例包括甲基铵、异丙基铵、二甲基铵、二异丙基铵、三甲基铵、四甲基铵、四乙基铵、四丁基铵、2-羟基乙基铵、2-(2-羟基乙氧基)乙基铵、二(2-羟基乙基)铵、苄基三甲基铵和苄基三乙基铵,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。
在各变量的上述定义中提到的有机结构部分象术语卤素一样为各基团成员的各次列举的集合性术语。前缀Cn-Cm在每种情况下表示该基团中可能的碳原子数。
术语卤素在每种情况下表示氟、溴、氯或碘,尤其是氟、氯或溴。
其他含义的实例是:
本文所用以及C1-C6烷氧基、C1-C6烷基氨基、二(C1-C6烷基)氨基、C1-C6烷硫基、C1-C6烷基磺酰基、C1-C6烷基亚磺酰基、(C1-C6烷基)羰基、(C1-C6烷氧基)羰基、(C1-C6烷硫基)羰基和(C1-C6烷基)羰基氧基的烷基结构部分中的术语“C1-C6烷基”指具有1-6个碳原子,尤其是1-4个碳原子的饱和直链或支化烃基,例如甲基、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、庚基、辛基、2-乙基己基、壬基、癸基及其异构体。C1-C4烷基例如指甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基或1,1-二甲基乙基。
本文所用术语“C1-C6卤代烷基”指具有1-6个碳原子的直链或支化饱和烷基(如上所述),其中这些基团中的部分或所有氢原子可以被上述卤原子代替,例如C1-C4卤代烷基,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、五氟乙基等。
本文所用术语“C1-C6烷氧基”指经由氧原子连接的具有1-6个碳原子的直链或支化饱和烷基(如上所述)。实例包括C1-C6烷氧基,如甲氧基、乙氧基、OCH2-C2H5、OCH(CH3)2、正丁氧基、OCH(CH3)-C2H5、OCH2-CH(CH3)2、OC(CH3)3、正戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲基丁氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基、2,2-二甲基丙氧基、1-乙基丙氧基、正己氧基、1-甲基戊氧基、2-甲基戊氧基、3-甲基戊氧基、4-甲基戊氧基、1,1-二甲基丁氧基、1,2-二甲基丁氧基、1,3-二甲基丁氧基、2,2-二甲基丁氧基、2,3-二甲基丁氧基、3,3-二甲基丁氧基、1-乙基丁氧基、2-乙基丁氧基、1,1,2-三甲基丙氧基、1,2,2-三甲基丙氧基、1-乙基-1-甲基丙氧基、1-乙基-2-甲基丙氧基等。
本文所用术语“C1-C6卤代烷氧基”指其中氢原子部分或完全被氟、氯、溴和/或碘替代的上述C1-C6烷氧基,即例如C1-C6卤代烷氧基,如氯甲氧基、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、2-氟乙氧基、2-氯乙氧基、2-溴乙氧基、2-碘乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-2,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基、五氟乙氧基、2-氟丙氧基、3-氟丙氧基、2,2-二氟丙氧基、2,3-二氟丙氧基、2-氯丙氧基、3-氯丙氧基、2,3-二氯丙氧基、2-溴丙氧基、3-溴丙氧基、3,3,3-三氟丙氧基、3,3,3-三氯丙氧基、2,2,3,3,3-五氟丙氧基、七氟丙氧基、1-(氟甲基)-2-氟乙氧基、1-(氯甲基)-2-氯乙氧基、1-(溴甲基)-2-溴乙氧基、4-氟丁氧基、4-氯丁氧基、4-溴丁氧基、九氟丁氧基、5-氟-1-戊氧基、5-氯-1-戊氧基、5-溴-1-戊氧基、5-碘-1-戊氧基、5,5,5-三氯-1-戊氧基、十一氟戊氧基、6-氟-1-己氧基、6-氯-1-己氧基、6-溴-1-己氧基、6-碘-1-己氧基、6,6,6-三氯-1-己氧基或十二氟己氧基、尤其是氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、2-氟乙氧基、2-氯乙氧基或2,2,2-三氟乙氧基.
本文所用术语“C1-C6烷氧基-C1-C6烷基”指其中1个碳原子带有上述C1-C6烷氧基的C1-C6烷基。实例是CH2-OCH3、CH2-OC2H5、正丙氧基甲基、CH2-OCH(CH3)2、正丁氧基甲基、(1-甲基丙氧基)甲基、(2-甲基丙氧基)甲基、CH2-OC(CH3)3、2-(甲氧基)乙基、2-(乙氧基)乙基、2-(正丙氧基)乙基、2-(1-甲基乙氧基)乙基、2-(正丁氧基)乙基、2-(1-甲基丙氧基)乙基、2-(2-甲基丙氧基)乙基、2-(1,1-二甲基乙氧基)乙基、2-(甲氧基)丙基、2-(乙氧基)丙基、2-(正丙氧基)丙基、2-(1-甲基乙氧基)丙基、2-(正丁氧基)丙基、2-(1-甲基丙氧基)丙基、2-(2-甲基丙氧基)丙基、2-(1,1-二甲基乙氧基)丙基、3-(甲氧基)丙基、3-(乙氧基)丙基、3-(正丙氧基)丙基、3-(1-甲基乙氧基)丙基、3-(正丁氧基)丙基、3-(1-甲基丙氧基)丙基、3-(2-甲基丙氧基)丙基、3-(1,1-二甲基乙氧基)丙基、2-(甲氧基)丁基、2-(乙氧基)丁基、2-(正丙氧基)丁基、2-(1-甲基乙氧基)丁基、2-(正丁氧基)丁基、2-(1-甲基丙氧基)丁基、2-(2-甲基丙氧基)丁基、2-(1,1-二甲基乙氧基)丁基、3-(甲氧基)丁基、3-(乙氧基)丁基、3-(正丙氧基)丁基、3-(1-甲基乙氧基)丁基、3-(正丁氧基)丁基、3-(1-甲基丙氧基)丁基、3-(2-甲基丙氧基)丁基、3-(1,1-二甲基乙氧基)丁基、4-(甲氧基)丁基、4-(乙氧基)丁基、4-(正丙氧基)丁基、4-(1-甲基乙氧基)丁基、4-(正丁氧基)丁基、4-(1-甲基丙氧基)丁基、4-(2-甲基丙氧基)丁基、4-(1,1-二甲基乙氧基)丁基等。
本文所用术语“(C1-C6烷基)羰基”指经由在烷基中的任何键处的羰基的碳原子键合的具有1-6个碳原子的直链或支化饱和烷基(如上所述)。实例包括C1-C6烷基羰基,如CO-CH3、CO-C2H5、正丙基羰基、1-甲基乙基羰基、正丁基羰基、1-甲基丙基羰基、2-甲基丙基羰基、1,1-二甲基乙基羰基、正戊基羰基、1-甲基丁基羰基、2-甲基丁基羰基、3-甲基丁基羰基、1,1-二甲基丙基羰基、1,2-二甲基丙基羰基、2,2-二甲基丙基羰基、1-乙基丙基羰基、正己基羰基、1-甲基戊基羰基、2-甲基戊基羰基、3-甲基戊基羰基、4-甲基戊基羰基、1,1-二甲基丁基羰基、1,2-二甲基丁基羰基、1,3-二甲基丁基羰基、2,2-二甲基丁基羰基、2,3-二甲基丁基羰基、3,3-二甲基丁基羰基、1-乙基丁基羰基、2-乙基丁基羰基、1,1,2-三甲基丙基羰基、1,2,2-三甲基丙基羰基、1-乙基-1-甲基丙基羰基或1-乙基-2-甲基丙基羰基等。
本文所用术语“(C1-C6烷氧基)羰基”指经由羰基的碳原子连接的具有1-6个碳原子的直链或支化烷氧基(如上所述),例如CO-OCH3、CO-OC2H5、COO-CH2-C2H5、CO-OCH(CH3)2、正丁氧羰基、CO-OCH(CH3)-C2H5、CO-OCH2-CH(CH3)2、CO-OC(CH3)3、正戊氧基羰基、1-甲基丁氧基羰基、2-甲基丁氧基羰基、3-甲基丁氧基羰基、2,2-二甲基丙氧基羰基、1-乙基丙氧基羰基、正己氧基羰基、1,1-二甲基丙氧基羰基、1,2-二甲基丙氧基羰基、1-甲基戊氧基羰基、2-甲基戊氧基羰基、3-甲基戊氧基羰基、4-甲基戊氧基羰基、1,1-二甲基丁氧基羰基、1,2-二甲基丁氧基羰基、1,3-二甲基丁氧基羰基、2,2-二甲基丁氧基羰基、2,3-二甲基丁氧基羰基、3,3-二甲基丁氧基羰基、1-乙基丁氧基羰基、2-乙基丁氧基羰基、1,1,2-三甲基丙氧基羰基、1,2,2-三甲基丙氧基羰基、1-乙基-1-甲基丙氧基羰基或1-乙基-2-甲基丙氧基羰基。
本文所用术语“(C1-C6烷基)羰基氧基”指经由在烷基中的任何键处的羰基氧基的碳原子键合的具有1-6个碳原子的直链或支化饱和烷基(如上所述),例如O-CO-CH3、O-CO-C2H5、正丙基羰基氧基、1-甲基乙基羰基氧基、正丁基羰基氧基、1-甲基丙基羰基氧基、2-甲基丙基羰基氧基、1,1-二甲基乙基羰基氧基、正戊基羰基氧基、1-甲基丁基羰基氧基、2-甲基丁基羰基氧基、3-甲基丁基羰基氧基、1,1-二甲基丙基羰基氧基或1,2-二甲基丙基羰基氧基。
本文所用术语“C1-C6烷硫基(C1-C6烷基硫基:C1-C6烷基-S-)”指经由硫原子连接的具有1-6个碳原子的直链或支化饱和烷基(如上所述),例如C1-C4烷硫基,如甲硫基、乙硫基、丙硫基、1-甲基乙硫基、丁硫基、1-甲基丙硫基、2-甲基丙硫基、1,1-二甲基乙硫基、正戊硫基羰基、1-甲基丁硫基、2-甲基丁硫基、3-甲基丁硫基、2,2-二甲基丙硫基、1-乙基丙硫基、正己硫基、1,1-二甲基丙硫基、1,2-二甲基丙硫基、1-甲基戊硫基、2-甲基戊硫基、3-甲基戊硫基、4-甲基戊硫基、1,1-二甲基丁硫基、1,2-二甲基丁硫基、1,3-二甲基丁硫基、2,2-二甲基丁硫基、2,3-二甲基丁硫基、3,3-二甲基丁硫基、1-乙基丁硫基、2-乙基丁硫基、1,1,2-三甲基丙硫基、1,2,2-三甲基丙硫基、1-乙基-1-甲基丙硫基或1-乙基-2-甲基丙硫基。
本文所用术语“(C1-C6烷硫基)羰基”指经由羰基碳原子连接的具有1-6个碳原子的直链或支化烷硫基(如上所述)。实例包括CO-SCH3、CO-SC2H5、CO-SCH2-C2H5、CO-SCH(CH3)2、正丁硫基羰基、CO-SCH(CH3)-C2H5、CO-SCH2-CH(CH3)2、CO-SC(CH3)3、正戊硫基羰基、1-甲基丁硫基羰基、2-甲基丁硫基羰基、3-甲基丁硫基羰基、2,2-二甲基丙硫基羰基、1-乙基丙硫基羰基、正己硫基羰基、1,1-二甲基丙硫基羰基、1,2-二甲基丙硫基羰基、1-甲基戊硫基羰基、2-甲基戊硫基羰基、3-甲基戊硫基羰基、4-甲基戊硫基羰基、1,1-二甲基丁硫基羰基、1,2-二甲基丁硫基羰基、1,3-二甲基丁硫基羰基、2,2-二甲基丁硫基羰基、2,3-二甲基丁硫基羰基、3,3-二甲基丁硫基羰基、1-乙基丁硫基羰基、2-乙基丁硫基羰基、1,1,2-三甲基丙硫基羰基、1,2,2-三甲基丙硫基羰基、1-乙基-1-甲基丙硫基羰基或1-乙基-2-甲基丙硫基羰基。
本文所用术语“C1-C6烷基亚磺酰基”(C1-C6烷基亚磺酰基:C1-C6烷基-S(=O)-)指通过在烷基中的任何键处的亚磺酰基的硫原子键合的具有1-6个碳原子的直链或支化饱和烃基(如上所述),例如SO-CH3、SO-C2H5、正丙基亚磺酰基、1-甲基乙基亚磺酰基、正丁基亚磺酰基、1-甲基丙基亚磺酰基、2-甲基丙基亚磺酰基、1,1-二甲基乙基亚磺酰基、正戊基亚磺酰基、1-甲基丁基亚磺酰基、2-甲基丁基亚磺酰基、3-甲基丁基亚磺酰基、1,1-二甲基丙基亚磺酰基、1,2-二甲基丙基亚磺酰基、2,2-二甲基丙基亚磺酰基、1-乙基丙基亚磺酰基、正己基亚磺酰基、1-甲基戊基亚磺酰基、2-甲基戊基亚磺酰基、3-甲基戊基亚磺酰基、4-甲基戊基亚磺酰基、1,1-二甲基丁基亚磺酰基、1,2-二甲基丁基亚磺酰基、1,3-二甲基丁基亚磺酰基、2,2-二甲基丁基亚磺酰基、2,3-二甲基丁基亚磺酰基、3,3-二甲基丁基亚磺酰基、1-乙基丁基亚磺酰基、2-乙基丁基亚磺酰基、1,1,2-三甲基丙基亚磺酰基、1,2,2-三甲基丙基亚磺酰基、1-乙基-1-甲基丙基亚磺酰基或1-乙基-2-甲基丙基亚磺酰基。
术语“C1-C6烷基氨基”指带有一个如上所定义的烷基的仲氨基,例如甲基氨基、乙基氨基、丙基氨基、1-甲基乙基氨基、丁基氨基、1-甲基丙基氨基、2-甲基丙基氨基、1,1-二甲基乙基氨基、戊基氨基、1-甲基丁基氨基、2-甲基丁基氨基、3-甲基丁基氨基、2,2-二甲基丙基氨基、1-乙基丙基氨基、己基氨基、1,1-二甲基丙基氨基、1,2-二甲基丙基氨基、1-甲基戊基氨基、2-甲基戊基氨基、3-甲基戊基氨基、4-甲基戊基氨基、1,1-二甲基丁基氨基、1,2-二甲基丁基氨基、1,3-二甲基丁基氨基、2,2-二甲基丁基氨基、2,3-二甲基丁基氨基、3,3-二甲基丁基氨基、1-乙基丁基氨基、2-乙基丁基氨基、1,1,2-三甲基丙基氨基、1,2,2-三甲基丙基氨基、1-乙基-1-甲基丙基氨基或1-乙基-2-甲基丙基氨基。
术语“二(C1-C6烷基)氨基”指带有两个如上所定义的烷基的叔氨基,例如二甲基氨基、二乙基氨基、二正丙基氨基、二异丙基氨基、N-乙基-N-甲基氨基、N-(正丙基)-N-甲基氨基、N-(异丙基)-N-甲基氨基、N-(正丁基)-N-甲基氨基、N-(正戊基)-N-甲基氨基、N-(2-丁基)-N-甲基氨基、N-(异丁基)-N-甲基氨基、N-(正戊基)-N-甲基氨基、N-(正丙基)-N-乙基氨基、N-(异丙基)-N-乙基氨基、N-(正丁基)-N-乙基氨基、N-(正戊基)-N-乙基氨基、N-(2-丁基)-N-乙基氨基、N-(异丁基)-N-乙基氨基或N-(正戊基)-N-乙基氨基。
本文所用术语“C1-C6烷基磺酰基”(C1-C6烷基-S(=O)2-)指通过在烷基中的任何键处的磺酰基的硫原子键合的具有1-6个碳原子的直链或支化饱和烷基(如上所述),例如SO2-CH3、SO2-C2H5、正丙基磺酰基、SO2-CH(CH3)2、正丁基磺酰基、1-甲基丙基磺酰基、2-甲基丙基磺酰基、SO2-C(CH3)3、正戊基磺酰基、1-甲基丁基磺酰基、2-甲基丁基磺酰基、3-甲基丁基磺酰基、1,1-二甲基丙基磺酰基、1,2-二甲基丙基磺酰基、2,2-二甲基丙基磺酰基、1-乙基丙基磺酰基、正己基磺酰基、1-甲基戊基磺酰基、2-甲基戊基磺酰基、3-甲基戊基磺酰基、4-甲基戊基磺酰基、1,1-二甲基丁基磺酰基、1,2-二甲基丁基磺酰基、1,3-二甲基丁基磺酰基、2,2-二甲基丁基磺酰基、2,3-二甲基丁基磺酰基、3,3-二甲基丁基磺酰基、1-乙基丁基磺酰基、2-乙基丁基磺酰基、1,1,2-三甲基丙基磺酰基、1,2,2-三甲基丙基磺酰基、1-乙基-1-甲基丙基磺酰基或1-乙基-2-甲基丙基磺酰基。
本文所用以及C2-C6链烯氧基、C2-C6链烯基氨基、C2-C6链烯硫基、C2-C6链烯基磺酰基、(C2-C6链烯基)羰基、(C2-C6链烯氧基)羰基和(C2-C6链烯基)羰基氧基的链烯基结构部分中的术语“C2-C6链烯基”指具有2-6个碳原子和在任意位置的双键的直链或支化不饱和烃基,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-丙烯基和1-乙基-2-甲基-2-丙烯基。
本文所用术语“C2-C6链烯氧基”指经由氧原子连接的具有2-6个碳原子的直链或支化饱和链烯基(如上所述),如乙烯氧基、烯丙氧基(丙烯-3-基氧基)、甲代烯丙氧基、丁烯-4-基氧基等。
本文所用术语“C2-C6链烯硫基”指经由硫原子连接的具有2-6个碳原子的直链或支化饱和链烯基(如上所述),例如乙烯基硫基、烯丙基硫基(丙烯-3-基硫基)、甲代烯丙基硫基、丁烯-4-基硫基等。
本文所用术语“C2-C6链烯基氨基”指经由硫原子连接的具有2-6个碳原子的直链或支化饱和链烯基(如上所述),例如乙烯基氨基、烯丙基氨基(丙烯-3-基氨基)、甲代烯丙基氨基、丁烯-4-基氨基等。
本文所用术语“C2-C6链烯基磺酰基”指经由磺酰基(SO2)连接的具有2-6个碳原子的直链或支化饱和链烯基(如上所述),例如乙烯基磺酰基、烯丙基磺酰基(丙烯-3-基磺酰基)、甲代烯丙基磺酰基、丁烯-4-基磺酰基等。
本文所用以及在C2-C6炔氧基、C2-C6炔基氨基、C2-C6炔硫基、C2-C6炔基磺酰基、C2-C6炔基羰基、C2-C6炔氧基羰基和C1-C6炔基羰基氧基的炔基结构部分中的术语“C2-C6炔基”指具有2-10个碳原子且含有至少一个叁键的直链或支化不饱和烃基,如乙炔基、丙-1-炔-1-基、丙-2-炔-1-基、正丁-1-炔-1-基、正丁-1-炔-3-基、正丁-1-炔-4-基、正丁-2-炔-1-基、正戊-1-炔-1-基、正戊-1-炔-3-基、正戊-1-炔-4-基、正戊-1-炔-5-基、正戊-2-炔-1-基、正戊-2-炔-4-基、正戊-2-炔-5-基、3-甲基丁-1-炔-3-基、3-甲基丁-1-炔-4-基、正己-1-炔-1-基、正己-1-炔-3-基、正己-1-炔-4-基、正己-1-炔-5-基、正己-1-炔-6-基、正己-2-炔-1-基、正己-2-炔-4-基、正己-2-炔-5-基、正己-2-炔-6-基、正己-3-炔-1-基、正己-3-炔-2-基、3-甲基戊-1-炔-1-基、3-甲基戊-1-炔-3-基、3-甲基戊-1-炔-4-基、3-甲基戊-1-炔-5-基、4-甲基戊-1-炔-1-基、4-甲基戊-2-炔-4-基或4-甲基戊-2-炔-5-基等。
本文所用术语“C2-C6炔氧基”指经由氧原子连接的具有2-6个碳原子的直链或支化饱和炔基(如上所述),如炔丙基氧基(丙炔-3-基氧基)、丁炔-3-基氧基和丁炔-4-基氧基。
本文所用术语“C2-C6炔硫基”指经由硫原子连接的具有2-6个碳原子的直链或支化饱和炔基(如上所述),如炔丙基硫基(丙炔-3-基硫基)、丁炔-3-基硫基和丁炔-4-基硫基。
本文所用术语“C2-C6炔基氨基”指经由硫原子连接的具有2-6个碳原子的直链或支化饱和炔基(如上所述),如炔丙基氨基(丙炔-3-基氨基)、丁炔-3-基氨基和丁炔-4-基氨基。
本文所用术语“C2-C6炔基磺酰基”指经由磺酰基(SO2)连接的具有2-6个碳原子的直链或支化饱和炔基(如上所述),如炔丙基磺酰基(丙炔-3-基磺酰基)、丁炔-3-基磺酰基和丁炔-4-基磺酰基。
本文所用术语“C3-C12环烷基”指具有3-12个碳原子,尤其是3-6个碳原子的单环或双环或多环烃基。单环基团的实例包括环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环壬基和环癸基。双环基团的实例包括双环[2.2.1]庚基、双环[3.1.1]庚基、双环[2.2.2]辛基和双环[3.2.1]壬基。三环基团的实例是金刚烷基和高金刚烷基。
本文所用术语“单环或双环杂芳族环”指具有5或6个环成员的单环杂芳族基团,其可以包含稠合的5、6或7员环且因此环成员总数为8-10,其中在每种情况下这些环成员中的1、2、3或4个为相互独立地选自氧、氮和硫的杂原子。杂环基团可以经由碳环成员或经由氮环成员连接到分子的其余部分。稠合的环包括C5-C7环烷基、C5-C7环烯基或5-7员杂环基和苯基。
带有稠合苯基环的5-6员杂芳族环的实例是喹啉基、异喹啉基、吲哚基、中氮茚基、异吲哚基、吲唑基、苯并呋喃基、苯并噻吩基、苯并[b]噻唑基、苯并唑基、苯并噻唑基、苯并唑基和苯并咪唑基。带有稠合环烯基环的5-6员杂芳族环的实例是二氢吲哚基、二氢中氮茚基、二氢异吲哚基、二氢喹啉基、二氢异喹啉基、苯并吡喃基、苯并二氢吡喃基等。
术语“5-7员杂环基”包括如上所定义的单环杂芳族环和具有5、6或7个环成员的非芳族饱和或部分不饱和杂环。非芳族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、二氧环戊烯基(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、二烷基、噻喃基、二氢噻喃基、四氢噻喃基、吗啉基、噻嗪基等。
考虑到式I化合物的杀虫活性,优选其中各变量相互独立地或与任何其他变量相结合地具有下列含义的那些式I化合物:
n为1、2或3;
m为1、2或3;
m+n=1、2、3、4、5或6,尤其是2、3、4或5;
R3氢或C1-C4烷基,尤其是氢或甲基,最优选氢;
R4氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基,或未被取代或被1-5个卤素、1-3个C1-C6烷基、C1-C6卤代烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基或C1-C6卤代烷氧基的任何组合取代的苯基;
R5氢、氰基、甲酰基、C1-C4烷基、C1-C6烷基羰基、C1-C4卤代烷基羰基、C1-C6烷氧基羰基、C1-C6烷硫基羰基或(C1-C6烷氧基)亚甲基;
R6氢、氰基、甲酰基、C1-C4烷基、C1-C6烷基羰基、C1-C4卤代烷基羰基、C1-C6烷氧基羰基、C1-C6烷硫基羰基或(C1-C6烷氧基)亚甲基;
R7为氢;
R8、R9、R10和R11各自为氢,这些基团中的一个还可以为C1-C4烷基;
Ra、Rb、Rc、Rd、Re、Rf相互独立地为氢或C1-C6烷基。
在本发明的非常优选实施方案中,基团R3和R4均为氢。在本发明的另一优选实施方案中,R3为氢且R4选自C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基,或未取代或被1-5个卤素、1-3个C1-C6烷基、C1-C6卤代烷基、C1-C6烷硫基、C1-C6卤代烷硫基、C1-C6烷氧基或C1-C6卤代烷氧基的任何组合取代的苯基。在该实施方案中,R4优选为甲基、乙基或尤其是未取代或取代的苯基。
在化合物I中,优选其中A为式A2的基团的那些,尤其是其中A为A2,其中R7为H的式I化合物。
若在这些化合物中R5也为氢,则它们为其中A为A1,其中R5和R6为氢的化合物I的互变异构体。这些互变异构体以其平衡混合物存在。
本发明化合物例如可以由对应的二苯基乙基胺II通过方案1和2中所示合成途径制备。
其中A为基团A2且R5和R7为氢的式I化合物可以根据方案1所示方法得到。
方案1:
根据方案1所示方法,可以通过常规方法将1,2-二苯基氨基乙烷II转化成对应的异硫氰酸酯III,例如通过使II与硫光气反应(例如参见Houben-Weyl,E4,“Methoden der Organischen Chemie”,第IIIc章,第837-842页,Georg Thieme Verlag 1983。
然后使该异硫氰酸酯III与式IV的1,2-二氨基乙烷反应,从而得到式V的硫脲化合物。该反应可以按照有机化学的标准方法进行,例如参见Tetrahedron 60,9883-9888(2004)。
如此得到的硫脲(V)可以通过常规方法环化,从而得到所需其中A为A2且R5和R7为氢的式I化合物。化合物(V)的环化可以经由中间体碳二亚胺形成和例如使用甲苯磺酰氯/NaOH的胺加成(例如参见Tetrahedron 60,9883-9888(2004))或根据Synthesis,482-484(1982)使用黄汞(II)的胺加成实现。
1,2-二苯基氨基乙烷II及其制备由文献已知或所述化合物可以通过常规方法制备。
其中A为式A2基团且R5和R7为氢的式I化合物还可以通过方案2所示方法得到。
方案2:
将异硫氰酸酯III转化成对应的硫脲VI,后者随后用碘甲烷处理而得到异硫脲盐VII。
最后使中间体VII与1,2-二氨基乙烷反应(例如参见US 2,899,426)。
式I化合物还可以按如下得到:
-使1,2-二苯基氨基乙烷II与2-取代的咪唑啉在例如如US 5,130,441中对可乐定(clonidin)的合成所述的合适溶剂中反应,
-使咪唑啉-2-磺酸与2,6-二氯苯胺在异丁醇中反应,
-使1,2-二苯基氨基乙烷II与2-甲硫基咪唑啉氢碘酸盐如EP-A 389765
所述(见实施例5)反应,
-使二苯基氨基乙烷II与2-卤代-1,3-二取代的咪唑啉或咪唑啉盐反应,例如如在T.Isobe等,Tetrahedron Asymmetry 9,1729-1735(1998)中对氯化2-氯-1,3-二甲基咪唑啉盐与胺的反应所述,该反应例如是为了制备化合物3a。
通常通过常规方法后处理特定反应混合物,例如通过除去溶剂、将残余物分配在水和合适的有机溶剂的混合物中并将产物从有机相中分离。
若中间体和终产物以固体得到,则可以通过重结晶或浸煮而将它们提纯。
1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物I可以在制备中以异构体混合物得到,然而需要的话可以通过常规方法将该混合物分离成纯异构体,例如通过结晶或层析(需要的话在旋光吸附物上进行)。纯旋光异构体例如可以由对应的旋光原料合成。
通常,式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物可以通过上述方法制备。然而,在个别的情况下某些化合物I还可以有利地通过衍生或通过上述合成途径的常规改进而由其他化合物I制备,例如通过在基团R1或R2位置处的酯水解、酰胺化、酯化、醚裂解、烯烃化、还原、氧化、交叉偶联反应或环化反应或通过在基团R5、R6或R7位置处的酯水解、酯交换、醚裂解或氧化。
由于其优异的活性,式I化合物可以用于控制动物害虫,尤其是选定的有害昆虫、蜘蛛和线虫。
因此,本发明进一步提供了用于对抗该类动物害虫的农用组合物,其包含具有杀虫作用的量的至少一种式I化合物或至少一种I的可农用盐以及至少一种惰性液体和/或固体可农用载体,和需要的话至少一种表面活性剂。
该组合物可以含有单一的式I的活性化合物或几种本发明活性化合物I的混合物。本发明的组合物可以包含单一的异构体或异构体混合物以及单一的互变异构体或互变异构体混合物。
式I化合物以及包含它们的杀虫组合物是用于防治动物害虫,尤其是选自昆虫、蜘蛛和线虫的那些的有效试剂。由式I化合物控制的动物害虫例如包括:
鳞翅目昆虫(鳞翅目(Lepidoptera)),例如小地老虎(Agrotis ypsilon)、黄地老虎(Agrotis segetum)、木棉虫(Alabama argillacea)、黎豆夜蛾(Anticarsiagemmatalis)、Argyresthia conjugella、叉纹夜蛾(Autographa gamma)、树尺蠖(Bupalus piniarius)、Cacoecia murinana、Capua reticulana、Cheimatobia brumata、云杉色卷蛾(Choristoneura fumiferana)、Choristoneura occidentalis、二化螟(Cirphis unipuncta)、苹果小卷蛾(Cydiapomonella)、松毛虫(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)、苹果巢蛾(Hyponomeuta malinellus)、番茄虫蛾(Keiferialycopersicella)、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)、黄杉毒蛾(Orgyia pseudotsugata)、玉米螟(Ostrinianubilalis)、小眼夜蛾(Panolis flammea)、棉花红铃虫(Pectinophoragossypiella)、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、绿色橡木飞蛾(Tortrix viridana)、粉纹夜蛾(Trichoplusia ni)和Zeiraphera canadensis;
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 asparagi)、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 japonica)、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)、Cordylobia anthropophaga、尖音库蚊(Culexpipiens)、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(Gasterophilusintestinalis)、刺舌蝇(Glossina morsitans)、Haematobia irritans、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)、Phorbiaantiqua、萝卜蝇(Phorbia brassicae)、Phorbia coarctata、樱桃实蝇(Rhagoletis cerasi)、苹果实蝇(Rhagoletis pomonella)、Tabanus bovinus、Tipula oleracea和欧洲大蚊(Tipula paludosa);
蓟马(缨翅目(Thysanoptera)),例如兰花蓟马(Dichromothrips corbetti)、烟褐蓟马(Frankliniella fusca)、苜蓿花蓟马(Frankliniella occidentalis)、东方花蓟马(Frankliniella tritici)、桔硬蓟马(Scirtothrips citri)、稻蓟马(Thripsoryzae)、棕榈蓟马(Thrips palmi)和烟蓟马(Thrips tabaci),膜翅目昆虫(膜翅目(Hymenoptera)),例如新疆菜叶蜂(Athalia rosae)、切叶蚁(Atta cephalotes)、Atta sexdens、Atta texana、Hoplocampaminuta、Hoplocampa testudinea、小黄家蚁(Monomorium pharaonis)、热带火蚁(Solenopsis geminate)和红火蚁(Solenopsis invicta),异翅目昆虫(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)、Euschistus impictiventris、棉红铃喙缘蝽(Leptoglossusphyllopus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lygus pratensis)、稻绿蝽(Nezara viridula)、甜菜拟网蝽(Piesma quadrata)、Solubea insularis和Thyanta perditor;
同翅目昆虫(同翅目(Homoptera)),例如Acyrthosiphon onobrychis、落叶松球蚜(Adelges laricis)、Aphidula nasturtii、蚕豆蚜(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)、Aphis schneideri、卷叶蚜(Aphis spiraecola)、Aphis sambuci、豌豆蚜(Acyrthosiphon pisum)、马铃薯蚜(Aulacorthumsolani)、银叶粉虱(Bemisia argentifolii)、Brachycaudus cardui、杏圆尾蚜(Brachycaudus helichrysi)、Brachycaudus persicae、Brachycaudusprunicola、甘蓝蚜(Brevicoryne brassicae)、Capitophorus horni、Cerosiphagossypii、Chaetosiphon fragaefolii、Cryptomyzus ribis、高加索冷杉椎球蚜(Dreyfusia nordmannianae)、云杉椎球蚜(Dreyfusia piceae)、居根西圆尾蚜(Dysaphis radicola)、Dysaulacorthum pseudosolani、Dysaphisplantaginea、Dysaphis pyri、蚕豆微叶蝉(Empoasca fabae)、桃大尾蚜(Hyalopterus pruni)、Hyperomyzus lactucae、麦长管蚜(Macrosiphumavenae)、大戟长管蚜(Macrosiphum euphorbiae)、蔷薇管蚜(Macrosiphonrosae)、Megoura viciae、巢莱修尾蚜(Melanaphis pyrarius)、麦无网蚜(Metopolophium dirhodum)、Myzodes persicae、冬葱瘤额蚜(Myzusascalonicus)、Myzus cerasi、桃蚜(Myzus persicae)、李瘤蚜(Myzus varians)、Nasonovia ribis-nigri、稻飞虱(Nilaparvata lugens)、囊柄瘿绵蚜(Pemphigusbursarius)、蔗飞虱(Perkinsiella saccharicida)、忽布疣蚜(Phorodonhumuli)、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)、Rhopalosiphum insertum、Sappaphis mala、Sappaphis mali、麦二叉蚜(Schizaphis graminum)、Schizoneuralanuginosa、麦长管蚜(Sitobion avenae)、白背飞虱(Sogatella furcifera)、白粉虱(Trialeurodes vaporariorum)、Toxoptera aurantiiand和葡萄根瘤蚜(Viteus vitifolii);
白蚁(等翅目(Isoptera)),例如Calotermes flavicollis、Leucotermes flavipes、黄肢散白蚁(Reticulitermes flavipes)、欧洲散白蚁(Reticulitermes lucifugus)和Termes natalensis;
直翅目昆虫(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 femur-rubrum)、墨西哥黑蝗(Melanoplus mexieanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplus spretus)、条纹红蝗(Nomadacris septemfasciata)、美洲蟑螂(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)、蜱科(Ixodidae)和疥螨科(Sarcoptidae),如长星形壁虱(Amblyommaamericanum)、热带花蜱(Amblyomma variegatum)、波斯锐缘蜱(Argaspersicus)、牛壁虱(Boophilus annulatus)、Boophilus decoloratus、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(Dermanyssus gallinae)、绵羊疥病(Psoroptesovis)、Rhipicephalus appendiculatus、Rhipicephalus evertsi、人疥螨(Sarcoptes scabiei),瘿螨属(Eriophyidae spp.),如苹果刺锈螨(Aculusschlechtendali)、Phyllocoptrata oleivora和Eriophyes sheldoni;细螨属(Tarsonemidae spp.),如Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemus latus);细须螨属(Tenuipalpidae spp.),如紫红短须螨(Brevipalpus phoenicis);叶螨属(Tetranychidae spp.),如朱砂叶螨(Tetranychus cinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychus pacificus)、棉叶螨(Tetranychus telarius)和二点叶螨(Tetranychus urticae),苹果叶螨(Panonychus ulmi)、柑椐叶螨(Panonychuscitri)和oligonychus pratensis;
蚤目(Siphonatera),例如Xenopsylla cheopsis、角叶(Ceratophyllus)属;
组合物和式I化合物可以用于控制线虫,尤其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(Meloidogyneincognita)、爪哇根结线虫(Meloidogyne javanica)和其他根结线虫属(Meloidogyne);形成孢囊的线虫,马铃薯金线虫(Globodera rostochiensis)和其他球胞囊属(Globodera);禾谷胞囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii)、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(Bursaphelenchus xylophilus)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(Ditylenchus destructor)、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,Longidoruselongatus和其他长针线虫属(Longidorus);针线虫,针线虫属(Paratylenchus);根腐线虫,Pratylenchus neglectus、穿刺根腐线虫(Pratylenchus penetrans)、Pratylenchus curvitatus、Pratylenchus goodeyi和其他根腐线虫属(Pratylenchus);穿孔线虫,香蕉穿孔线虫(Radopholussimilis)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,Trichodorusprimitivus和其他毛刺线虫属(Trichodorus)、拟毛刺属(Paratrichodorus);阻长线虫,Tylenchorhynchus claytoni、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。
在本发明的优选实施方案中,将式I化合物用于控制昆虫或蜘蛛,尤其是鳞翅目、鞘翅目和同翅目昆虫以及蜱螨目蜘蛛。本发明的式I化合物特别可以用于控制鳞翅目和同翅目昆虫。
式I化合物或包含它们的杀虫组合物可以用于保护生长的植物和作物以防动物害虫,尤其是昆虫、粉螨或蜘蛛的侵袭或侵染,通过使植物/作物与杀虫有效量的式I化合物接触。术语“作物”指生长的作物和收获的作物二者。
对于本发明的应用,可以将化合物I转化成常规配制剂,例如溶液、乳液、悬浮液、粉剂、粉末、糊和颗粒。使用形式取决于特定的目的;在任何情况下意欲确保本发明化合物精细和均匀的分布。
用于对抗动物害虫,即昆虫、蜘蛛或线虫的杀虫组合物含有该量的至少一种通式I化合物或I的可农用盐和常用于配制杀虫组合物的助剂。
配制剂以已知方式制备,例如通过将活性成分与溶剂和/或载体混合而制备,若需要的话使用乳化剂和分散剂。合适的溶剂/助剂主要为:
-水、芳族溶剂(如Solvesso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(NMP、NOP)、乙酸酯(乙二醇二乙酸酯)、二元醇、脂肪酸二甲基酰胺、脂肪酸及脂肪酸酯。原则上还可以使用溶剂混合物。
-载体如磨碎的天然矿物(如高岭土、粘土、滑石、白垩)和磨碎的合成矿物(如高度分散的硅石、硅酸盐);乳化剂如非离子和阴离子乳化剂(如聚氧乙烯脂肪醇醚、烷基磺酸盐和芳基磺酸盐)以及分散剂如木素亚硫酸盐废液和甲基纤维素。
合适的表面活性剂是木素磺酸、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,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基苯基醚,乙氧基化的异辛基酚、辛基酚、壬基酚,烷基苯基聚乙二醇醚,三丁基苯基聚乙二醇醚,三硬脂基苯基聚乙二醇醚,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是中沸点到高沸点的矿物油馏分,如煤油或柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃,例如苯、甲苯、二甲苯、石蜡、四氢化萘、烷基化萘或其衍生物、甲醇、乙醇、丙醇、丁醇、氯仿、四氯化碳、环己醇、环己酮、氯苯、异佛尔酮,强极性溶剂,例如二甲基甲酰胺、二甲亚砜、N-甲基吡咯烷酮和水。
粉末、撒播用材料和粉剂可以通过将活性物质与固体载体混合或同时研磨而制备。
颗粒如涂覆颗粒、压实颗粒、浸渍颗粒和均质颗粒可以通过将活性成分与固体载体粘附而制备。固体载体的实例是矿土如硅石、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;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。
本发明的该类配制剂或组合物包括与一种或多种可农用的惰性固体或液体载体混合的本发明式I化合物(或其组合)。这些组合物含有杀虫有效量的所述化合物,该量可以随特定化合物、目标害虫和使用方法而变化。
通常,配制剂包含0.01-95重量%,优选0.1-90重量%的活性成分。活性成分以90-100%,优选95-100%的纯度(根据NMR谱)使用。
下列为配制剂实例:
1.叶部施用的用水稀释的产品。对于种子处理目的,该类产品可以稀释或不稀释地施用于种子。
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,从而得到含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,从而得到含有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,从而得到含有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(Ultraturrax)将该混合物引入30重量份水中并制成均匀乳液。用水稀释得到乳液,从而得到含有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、湿润剂和70重量份水或有机溶剂,得到微细活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液,从而得到含有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重量份活性化合物精细研磨并加入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,从而得到含有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,从而得到含有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重量份活性化合物粉碎,加入10重量份分散剂、1重量份胶凝剂润湿剂和70重量份水或有机溶剂,得到微细活性化合物悬浮液。用水稀释得到活性化合物的稳定悬浮液,从而得到含有20重量%活性化合物的配制剂。
2.叶部施用的不经稀释而施用的产品。对于种子处理目的,该类产品可以稀释或不稀释地施用于种子。
I)可撒粉粉末(DP、DS)
将5重量份活性化合物精细研磨并与95重量份细碎高岭土充分混合。这得到含有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95.5重量份载体,从而得到含有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。这得到不经稀释而用于叶部应用的颗粒。
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。这得到含有10重量%活性化合物的产品,其不经稀释而施用于叶部。
活性成分可以直接、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、粉剂、撒播用材料或颗粒形式),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;在任何情况下应确保本发明活性成分的最佳可能分布。
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。或者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。
即用产品中的活性成分浓度可在显著的范围内变化。通常,它们为0.0001-10%,优选0.01-1%。
活性成分也可成功地以超低容量法(ULV)使用,其中可以施用包含超过95重量%活性成分的配制剂,或甚至施用不含添加剂的活性成分。
各种类型的油、湿润剂、辅助剂、除草剂、杀真菌剂、其它农药或杀菌剂都可加入活性成分中,若合适的话,恰在紧临使用前加入(桶混合)。这些试剂通常与本发明试剂以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、蚊帐(bed net)、地毯、植物部分或动物部分)和摄食(诱饵或植物部分)而有效。
为了用于蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀或蟑螂,优选将式I化合物用于诱饵组合物中。
诱饵可以是液体、固体或半固体制剂(例如凝胶)。可以将固体诱饵成形为各种适合相应用途的形状和形式,如颗粒、块、棒、片。液体诱饵可以填充到各种装置中以确保适当施用,例如敞开容器、喷雾装置、液滴源或蒸发源。凝胶可以基于含水或油状基质且可以按照粘性、水分保留或老化特性的特殊要求配制。
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去吃的产品。该吸引可以通过使用进食刺激剂或性信息素调节。进食刺激剂例如选自但不仅仅选自动物和/或植物蛋白(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有机糖、低聚有机糖或聚有机糖,尤其是选自蔗糖、乳糖、果糖、右旋糖、葡糖糖、淀粉、果胶或甚至糖蜜或蜂蜜。水果、作物、植物、动物、昆虫或其特定部分的新鲜或腐败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。特异性信息素描述于文献中且对本领域熟练技术人员是已知的。
式I化合物的配制剂如气雾剂(例如在喷雾罐中)、油喷雾剂或泵喷雾剂高度适于非专业使用者来控制害虫如蝇、跳蚤、蜱、蚊子或蟑螂。气雾剂配方优选由如下组分组成:活性化合物;溶剂如低级醇(例如甲醇、乙醇、丙醇、丁醇),酮类(例如丙酮、甲基乙基酮),沸点范围为约50-250℃的链烷烃(例如煤油),二甲基甲酰胺,N-甲基吡咯烷酮,二甲亚砜,芳族烃类如甲苯、二甲苯,水;此外还有助剂,例如乳化剂如山梨糖醇单油酸酯、具有3-7mol氧化乙烯的油基乙氧基化物、脂肪醇乙氧基化物,香料油如精油,中等脂肪酸与低级醇的酯,芳族羰基化合物;合适的话还有稳定剂如苯甲酸钠,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、氧化亚氮或这些气体的混合物。
油喷雾配制剂与气雾剂配方的不同在于没有使用推进剂。
式I化合物及其相应的组合物还可以用于蚊香片和熏蒸片,发烟盒、蒸发器板或长效蒸发器以及防蛀纸、防蛀垫或其他与热无关的蒸发器体系中。
式I化合物及其相应组合物控制由昆虫传递的传染性疾病(例如疟疾、登革热和黄热病,淋巴丝虫病以及利什曼病)的方法也包括处理棚屋和房子的表面、空气喷雾和浸渍窗帘、帐篷、衣物、蚊帐、采采蝇捕捉器等。施用于纤维、织物、编织物、无纺织物、网状材料或箔以及篷布上的杀虫组合物优选包含包含杀虫剂、任选的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-间甲苯甲酰胺(DEET),N,N-二乙基苯基乙酰胺(DEPA),1-(3-环己烷-1-基羰基)-2-甲基哌啶,(2-羟基甲基环己基)乙酸内酯,2-乙基-1,3-己二醇,避蚊酮,甲基新癸酰胺(MNDA),未用于昆虫控制的拟除虫菊酯如{(+/-)-3-烯丙基-2-甲基-4-氧代环戊-2-(+)-烯基-(+)-反式-菊酸酯(Esbiothrin),衍生于植物提取物或与植物提取物相同的驱除剂如1,8-萜二烯、丁子香酚、(+)-Eucamalol(1)、(-)-1-表-eucamalol,或来自诸如花皮桉(Eucalyptus maculata)、单叶蔓荆(Vitex rotundifolia)、Cymbopogan martinii、香茅(Cymbopogan citratus)(柠檬草)、亚香茅(Cymopogan nartdus)(香茅)的植物的粗植物提取物。合适的粘合剂例如选自如下单体的聚合物和共聚物:脂族酸的乙烯基酯(如乙酸乙烯酯和支链烷烃脂肪酸(versatic)乙烯基酯),醇的丙烯酸和甲基丙烯酸酯,如丙烯酸丁酯、丙烯酸2-乙基己基酯和丙烯酸甲酯,单烯属和二烯属不饱和烃,如苯乙烯,以及脂族二烯,如丁二烯。
窗帘和蚊帐的浸渍在大多数情况下通过将织物材料浸入杀虫剂的乳液或分散体中或将它们喷雾于所述材料上而进行。
式I化合物还适于处理种子。常规种子处理剂例如包括流动剂FS、溶液LS、干拌种粉末DS、湿拌种用水分散性粉末WS、水溶性粉末SS和乳液ES。对种子的施用在播种之前进行,直接施用于种子上或在已对种子催芽之后施用。
用于种子处理的式I化合物的优选FS配制剂通常包含0.5-80%活性成分,0.05-5%润湿剂,0.5-15%分散剂,0.1-5%增稠剂,5-20%防冻剂,0.1-2%消泡剂,1-20%颜料和/或染料,0-15%粘着剂/粘附剂,0.75%的填料/赋形剂和0.01-1%防腐剂。
加入粘着剂/粘附剂以改善处理之后活性物质对种子的粘附。合适的粘合剂为EO/PO嵌段共聚物表面活性剂,还有聚乙烯醇、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(Lupasol、Polymin)、聚醚和衍生于这些聚合物的共聚物。
本发明使用的组合物还可以含有其他活性成分,例如其他农药,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、钾碱和过磷酸钙,植物毒性试剂和植物生长调节剂,安全剂和杀线虫剂。这些额外成分可以顺序使用或与上述组合物组合使用,合适的话也仅在紧临使用前加入(桶混合)。例如,植物可以在用其他活性成分处理之前或之后用本发明组合物喷雾。
这些试剂可以与本发明使用的试剂以1∶10-10∶1的重量比混合。将以杀虫剂形式使用的化合物I或包含它们的组合物与其他杀虫剂混合通常导致更宽的杀虫作用谱。
可与式I化合物一起使用的下列农药用来阐述可能的组合,而不施以任何限制:
有机(硫代)磷酸酯类:高灭磷(Acephate)、唑啶磷(Azamethiphos)、谷硫磷(Azinphos-methyl)、毒死蜱(Chlorpyrifos)、甲基毒死蜱(Chlorpyrifos-methyl)、毒虫畏(Chlorfenvinphos)、二嗪农(Diazinon)、敌敌畏(Dichlorvos)、百治磷(Dicrotophos)、乐果(Dimethoate)、乙拌磷(Disulfoton)、乙硫磷(Ethion)、杀螟松(Fenitrothion)、倍硫磷(Fenthion)、异唑磷(Isoxathion)、马拉硫磷(Malathion)、甲胺磷(Methamidophos)、杀扑磷(Methidathion)、甲基一六零五(Methyl-Parathion)、速灭磷(Mevinphos)、久效磷(Monocrotophos)、砜吸磷(Oxydemeton-methyl)、对氧磷(Paraoxon)、一六零五(Parathion)、稻丰散(Phenthoate)、伏杀磷(Phosalone)、亚胺硫磷(Phosmet)、磷胺(Phosphamidon)、甲拌磷(Phorate)、辛硫磷(Phoxim)、虫螨磷(Pirimiphos-methyl)、丙溴磷(Profenofos)、丙硫磷(Prothiofos)、乙丙硫磷(Sulprophos)、杀虫威(Tetrachlorvinphos)、特丁磷(Terbufos)、三唑磷(Triazophos)、敌百虫(Trichlorfon);
氨基甲酸酯类:棉铃威(Alanycarb)、虫威(Bendiocarb)、丙硫克百威(Benfuracarb)、甲萘威(Carbaryl)、虫螨威(Carbofuran)、丁硫克百威(Carbosulfan)、双氧威(Fenoxycarb)、呋线威(Furathiocarb)、二唑虫(Indoxacarb)、灭虫威(Methiocarb)、灭多虫(Methomyl)、甲氨叉威(Oxamyl)、抗蚜威(Pirimicarb)、残杀威(Propoxur)、硫双威(Thiodicarb)、唑蚜威(Triazamate);
拟除虫菊酯类:丙烯除虫菊(Allethrin)、氟氯菊酯(Bifenthrin)、氟氯氰菊酯(Cyfluthrin)、(RS)氯氟氰菊酯(Cyhalothrin)、苯醚氰菊酯(Cyphenothrin)、氯氰菊酯(Cypermethrin)、甲体氯氰菊酯(alpha-Cypermethrin)、乙体氯氰菊酯(beta-Cypermethrin)、己体氯氰菊酯(zeta-Cypermethrin)、溴氰菊酯(Deltamethrin)、高氰戊菊酯(Esfenvalerate)、醚菊酯(Ethofenprox)、甲氰菊酯(Fenpropathrin)、杀灭菊酯(Fenvalerate)、咪炔菊酯(Imiprothrin)、氯氟氰菊酯(Lambda-Cyhalothrin)、氯菊酯(Permethrin)、炔酮菊酯(Prallethrin)、除虫菊酯I(Pyrethrin-I)和除虫菊酯(Pyrethrin-II)、灭虫硅醚(Silafluofen)、氟胺氰菊酯(Tau-Fluvalinate)、七氟菊酯(Tefluthrin)、胺菊酯(Tetramethrin)、四溴菊酯(Tralomethrin)、四氟菊酯(Transfluthrin);
生长调节剂:a)几丁质合成抑制剂:苯甲酰脲类,如定虫隆(Chlorfluazuron)、Cyramazin、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)、伏虫隆(Teflubenzuron)、杀虫隆(Triflumuron);噻嗪酮(Buprofezin)、茂醚(Diofenolan)、噻螨酮(Hexythiazox)、特苯唑(Etoxazole)、四螨嗪(Clofentazine);b)蜕皮激素拮抗剂:例如特丁苯酰肼(Halofenozide)、甲氧苯酰肼(Methoxyfenozide)、双苯酰肼(Tebufenozide);c)保幼激素类似物:例如蚊蝇醚(Pyriproxyfen)、蒙五一五(Methoprene)、双氧威(Fenoxycarb);d)类脂生物合成抑制剂:例如螺螨酯(Spirodiclofen)、螺甲螨酯(Spiromesifen)、式VIII的季酮酸衍生物:
新烟碱类(neonieotinoid):噻虫胺(Clothianidine)、呋虫胺(Dinotefuran)、吡虫啉(Imidacloprid)、噻虫嗪(Thiamethoxam)、硝胺烯啶(Nitenpyram)、硝虫噻嗪(Nithiazine)、吡虫清(Acetamiprid)、噻虫啉(Thiacloprid);
吡唑类杀虫剂,如Acetoprole、乙虫清(Ethiprole)、锐劲特(Fipronil)、吡螨胺(Tebufenpyrad)、唑虫酰胺(Tolfenpyrad)、氟吡唑虫(Vaniliprole);
各种:齐墩螨素(Abamectin)、灭螨醌(Acequinocyl)、Amidoflumet、虫螨脒(Amitraz)、艾扎丁(Azadirachtin)、Benclothiaz、联苯肼酯(Bifenazate)、双三氟虫脲(Bistrifluron)、杀螟丹(Cartap)、氟唑虫清(Chlorfenapyr)、杀虫脒(Chlordimeform)、丁氟螨酯(Cyflumetofen)、灭蝇胺(Cyromazine)、杀螨硫隆(Diafenthiuron)、四氟甲醚菊酯(Dimefluthrin)、茂醚(Diofenolan)、埃玛菌素(Emamectin)、硫丹(Endosulfan)、喹螨醚(Fenazaquin)、氟啶虫酰胺(Flonicamid)、Fluacyprim、氟虫酰胺(Flubendiamide)、Flufeherim、吡氟硫磷(Flupyrazofos)、伐虫脒(Formetanate)、伐虫脒盐酸盐(Formetanate hydrochloride)、灭蚁腙(Hydramethylnon)、二唑虫(Indoxacarb)、Lepimectin、氰氟虫胺(Metaflumizone)、米尔螨素(Milbemectin)、增效醚(Piperonylbutoxide)、丙氟菊酯(Profluthrin)、哒螨酮(Pyridaben)、啶虫丙醚(Pyridalyl)、据嗪酮(Pymetrozine)、Pyrafluprole、Pyriprole、艾克敌105(Spinosad)、螺虫乙酯(Spirotetramat)、硫、吡螨胺(Tebufenpyrad)、硫环杀(Thiocyclam)、唑虫酰胺(Tolfenpyrad)和式IX的氨基异噻唑化合物:
其中Ri为氢或-CH2OCH3且Rii为-CF2CF2CF3,
式X的邻氨基苯甲酰胺化合物:
其中Riii为氢或氯原子,Riv为溴原子或CF3且Rv为C1-C6烷基,以及JP 2002/284608、WO 02/89579、WO 02/90320、WO 02/90321、WO04/06677、WO 04/20399或JP 2004/099597中所述的丙二腈化合物。
杀真菌混合配对为选自如下的那些:
·胺衍生物,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)、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(cyrodinyl),
·抗菌素,例如放线菌酮(cycloheximid)、灰黄霉素(griseofulvin)、春雷素霉(kasHgamycin)、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(dinitroconazole)、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(triflumizol)、戊叉唑菌(triticonazole)、粉唑醇(flutriafol),
·二羧酰亚胺类,如异丙定(iprodion)、甲菌利(myclozolin)、杀菌利(procymidon)、烯菌酮(vinclozolin),
·二硫代氨基甲酸盐类,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)、代森锌(zineb),
·杂环化合物,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(famoxadon)、咪唑菌酮(fenamidon)、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)、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(thifluzamid)、甲基托布津(thiophanate-methyl)、噻酰菌胺(tiadinil)、三环唑(tricyclazole)、嗪氨灵(triforine),
·铜杀真菌剂,如波尔多液(Bordeaux混合物)、醋酸铜、王铜(copperoxychloride)、碱式硫酸铜,
·硝基苯基衍生物,如乐杀螨(binapacryl)、敌螨普(dinocap)、敌螨通(dinobuton)、异丙消(nitrophthalisopropyl),
·硫,
·其它杀真菌剂,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)、棉隆(dazomet)、哒菌清(diclomezin)、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)、藻菌磷(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(zoxamid),
·嗜球果伞素类(strobilurin),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,如敌菌丹(captafol)、克菌丹(captan)、抑菌灵(dichlofluanid)、灭菌丹(folpet)或对甲抑菌灵(tolylfluanid),
·肉桂酰胺及类似化合物,如烯酰吗啉(dimethomorph)、氟联苯菌(flumetover)或氟吗啉(flumorph)。
可以使动物害虫,即昆虫、蜘蛛和线虫,植物生长于其中的植物,土壤或水体与本发明化合物I或含有它们的组合物通过任何本领域已知的施用方法接触。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所在场所或植物)。
此外,动物害虫可以通过使目标害虫、其食物供应源、栖息地、繁殖地或其场所与杀虫有效量的式I化合物接触而控制。这里的施用可以在场所、生长作物或收获的作物被害虫侵染之前或之后进行。
“场所”是指害虫或寄生虫生长或可能生长于其中的栖息地、繁殖地、植物、种子、土壤、区域、材料或环境。
通常而言,“杀虫有效量”指对生长获得可观察到的效果所需的活性成分的量,所述效果包括坏死、死亡、延缓、预防和除去效果,破坏效果或目标生物体的出现和活动降低效果。对于用于本发明的各种化合物/组合物,杀虫有效量可以变化。组合物的杀虫有效量也可以根据盛行的条件如所需杀虫效果和持续时间、气候、目标种类、场所、施用方式等而改变。
式I化合物及其组合物可以用于保护木质材料,例如树、板垣、枕木等以及建筑物如房屋、附属建筑、工厂,还有建筑材料、家具、皮革、纤维、乙烯制品、电线和电缆等以防蚂蚁和/或白蚁,以及用于防止蚂蚁和白蚁危害作物或人类(例如当害虫侵入房屋和公共设备时)。式I化合物不仅施用于周围土壤表面或地下土壤以保护木质材料,而且还可以施用于木料制品如地下混凝土、邮亭、横梁、胶合板、家具等的表面,木质制品如碎料板、半成品板(half board)等以及乙烯制品如涂敷电线、乙烯板,绝热材料如苯乙烯泡沫等。在防止蚂蚁危害作物或人类的应用情况下,将本发明的蚂蚁控制剂施用于作物或周围土壤,或直接施用于蚁穴等。
本发明化合物还可以预防性地施用于预期出现害虫的地方。
式I化合物还可以用于保护生长植物以防害虫侵袭或侵染,其中使植物与杀虫有效量的式I化合物接触。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)。
上述组合物尤其可以用于保护作物植株以防所述害虫侵染或在侵染的植株中对抗这些害虫。
对于在处理作物植株中的应用,本发明活性成分的施用率可以为0.1-4000g/公顷,理想的是25-600g/公顷,更理想的是50-500g/公顷。
在土壤处理或施用于害虫居住场所或巢穴的情况下,活性成分的量为0.0001-500g/100m2,优选0.001-20g/100m2。
在材料保护中的常用施用率例如为0.01-1000g活性化合物/m2被处理材料,理想的是0.1-50g/m2。
用于材料浸渍中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。
对于诱饵组合物中的应用,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。
对于喷雾组合物中的应用,活性成分的含量为0.001-80重量%,优选0.01-50重量%,最优选0.01-15重量%。
对于处理作物植株中的应用,本发明活性成分的施用率可以为0.1-4000g/公顷,理想的是25-600g/公顷,更理想的是50-500g/公顷。
式I化合物还适合处理种子以保护种子而防止昆虫害虫,尤其是土壤昆虫害虫并保护所得植物的根和芽以防土壤害虫和叶部昆虫。
式I化合物特别可以用于保护种子以防土壤生活害虫并保护所得植物的根和芽以防土壤害虫和叶部昆虫。优选所得植物的根和芽的保护。更优选保护所得植物的芽以防刺吸式昆虫,其中最优选防止蚜虫。
本发明因此包括一种保护种子以防昆虫,尤其是土壤昆虫以及保护秧苗的根和芽以防昆虫,尤其是土壤和叶部昆虫的方法,该方法包括使种子在播种之前和/或在催芽之后与通式I的化合物或其盐接触。特别优选其中保护植物的根和芽的方法,更优选其中保护植物芽以防刺吸式昆虫的方法,最优选其中保护植物芽以防蚜虫的方法。
术语种子包括所有种类的种子和植物繁殖体,包括但不限于真正的种子、种子切片(seed piece)、吸枝、球茎、鳞茎、果实、块茎、谷粒、插条、伐条(cut shoot)等,并且在优选实施方案中指真正的种子。
尤其可以用于种子处理的组合物例如为:
A水溶性浓缩物(SL、LS)
D乳液(EW、EO、ES)
E悬浮液(SC、OD、FS)
F水分散性颗粒和水溶性颗粒(WG、SG)
G水分散性粉末和水溶性粉末(WP、SP、SS、WS)
H凝胶配制剂(GF)
I可撒粉粉末(DP、DS)
式I化合物还适于处理种子。常规种子处理剂例如包括流动剂FS、溶液LS、干拌种粉末DS、湿拌种用水分散性粉末WS、水溶性粉末SS和乳液ES。对种子的施用在播种之前进行,直接施用于种子上或在已对种子催芽之后施用。
用于种子处理的式I化合物的优选FS配制剂通常包含0.1-80重量%(1-800g/L)活性成分,0.1-20重量%(1-200g/L)至少一种表面活性剂,例如0.05-5重量%润湿剂和0.5-15重量%分散剂,至多20重量%,例如5-20%防冻剂,0-15重量%,例如1-15重量%颜料和/或染料,0-40重量%,例如1-40重量%粘合剂(粘着剂/粘附剂),任选至多5重量%,例如0.1-5重量%增稠剂,任选0.1-2%消泡剂,以及例如用量为0.01-1重量%的任选防腐剂如生物杀伤剂、抗氧化剂等,和至多100重量%的填料/赋形剂。
对种子处理配制剂合适的颜料或染料为颜料蓝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。
加入也称为粘着剂/粘附剂的粘合剂以改善处理之后活性物质对种子的粘附。合适的粘合剂为EO/PO嵌段共聚物表面活性剂,还有聚乙烯醇、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(Lupasol、Polymin)、聚醚和衍生于这些聚合物的共聚物。
在种子处理中,化合物I的施用率通常为0.1g-10kg/100kg种子,优选1g-5kg/100kg种子,尤其是1g-1000g/100kg种子。
本发明因此还涉及包含本文所定义的式I化合物或I的可农用盐的种子。化合物I或其可农用盐的量通常在0.1g-10kg/100kg种子,优选1g-5kg/100kg种子,尤其是1-1000g/100kg种子的范围内变化。
还可以施用本发明化合物以防非作物昆虫害虫,如蚂蚁、白蚁、黄蜂、蝇、蚊子、蟋蟀或蟑螂。为了用于所述非作物害虫,优选将式I化合物用于诱饵组合物中。
诱饵可以是液体、固体或半固体制剂(例如凝胶)。可以将固体诱饵成形为各种适合相应用途的形状和形式,如颗粒、块、棒、片。液体诱饵可以填充到各种装置中以确保适当施用,例如敞开容器、喷雾装置、液滴源或蒸发源。凝胶可以基于含水或油状基质且可以按照粘性、水分保留或老化特性的特殊要求配制。
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去吃的产品。该吸引可以通过使用进食刺激剂或性信息素调节。进食刺激剂例如选自但不仅仅选自动物和/或植物蛋白(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有机糖、低聚有机糖或聚有机糖,尤其是选自蔗糖、乳糖、果糖、右旋糖、葡糖糖、淀粉、果胶或甚至糖蜜或蜂蜜。水果、作物、植物、动物、昆虫或其特定部分的新鲜或腐败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。特异性信息素描述于文献中且对本领域熟练技术人员是已知的。
为了用于诱饵组合物中,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。
式I化合物的配制剂如气雾剂(例如在喷雾罐中)、油喷雾剂或泵喷雾剂高度适于非专业使用者来控制害虫如蝇、跳蚤、蜱、蚊子或蟑螂。气雾剂配方优选由如下组分组成:活性化合物;溶剂如低级醇(例如甲醇、乙醇、丙醇、丁醇),酮类(例如丙酮、甲基乙基酮),沸点范围为约50-250℃的链烷烃(例如煤油),二甲基甲酰胺,N-甲基吡咯烷酮,二甲亚砜,芳族烃类如甲苯、二甲苯,水;此外还有助剂,例如乳化剂如山梨糖醇单油酸酯、具有3-7mol氧化乙烯的油基乙氧基化物、脂肪醇乙氧基化物,香料油如精油,中等脂肪酸与低级醇的酯,芳族羰基化合物;合适的话还有稳定剂如苯甲酸钠,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、氧化亚氮或这些气体的混合物。
油喷雾配制剂与气雾剂配方的不同在于没有使用推进剂。
为了用于喷雾组合物中,活性成分的含量为0.001-80重量%,优选0.01-50重量%,最优选0.01-15重量%。
式I化合物及其相应的组合物还可以用于蚊香片和熏蒸片,发烟盒、蒸发器板或长效蒸发器以及防蛀纸、防蛀垫或其他与热无关的蒸发器体系中。
现在由下列实施例更详细说明本发明。
1.化合物制备实施例
实施例P.1:
[2-(3-氯苯基)-1-苯基乙基]-(4,5-二氢-1H-咪唑-2-基)胺氢碘酸盐
在室温下将1.22g(5.00mmol)2-甲硫基-4,5-二氢-1H-咪唑加入1.16g(5.00mmol)2-(3-氯苯基)-1-苯基乙基胺在正戊醇中的溶液中并加热到回流2小时。将反应混合物冷却并减压浓缩。用少部分乙酸乙酯处理导致沉淀。过滤沉淀物并减压干燥,得到0.85g(1.99mmol,40%)所需化合物。
实施例P.2:
1-[2-(1,2-二苯基乙基氨基)-4,5-二氢咪唑-1-基]乙酮(化合物2.1)
将457mg(4,5-二氢-1H-咪唑-2-基)-(1,2-二苯基乙基)胺氢碘酸盐(1.16mmol)和400mg碳酸钾(2.9mmol)在20ml二甲基甲酰胺中的混合物用83mg乙酰氯(1.06mmol)处理并加热到50℃保持6小时。用乙酸乙酯和水进行含水处理,得到粗产物,通过在硅胶上的柱层析提纯得到70mg产物(0.23mmol,22%)。
相应地可以制备式Ia和Ib化合物。这些化合物的物理化学数据列于表1和2中。
表1:
实施例 | (R1)m | (R2)n | 物理化学数据(熔点[℃];1H-NMR(CDCl3):δ[ppm]) |
1.1HI-盐 | 3-Cl | - | 熔点:162-164℃ |
1.2HI-盐 | 4-Cl | - | 3.0-3.4(m),4.85(mc),6.1(br s),7.2-7.4(m),8.4(br s),8.9(d) |
1.3HI-盐 | 2-Cl,4-F | 3.2-3.4(mc),4.85(mc),5.6(br s),6.85-7.45(m),7.7(br s),9.0(d) | |
1.4游离碱 | 3-Cl | - | 3.05(mc),3.5(m),4.8(m),7.15-7.4(m),9.0(m) |
实施例 | (R1)m | (R2)n | 物理化学数据(熔点[℃];1H-NMR(CDCl3):δ[ppm]) |
1.5 | 3-F | - | 2.8-3.1(m),3.2-4.5(m),4.75(m),6.9-7.4(m) |
表2:
实施例 | (R1)m | (R2)n | R5 | 物理化学数据(熔点[℃];1H-NMR(CDCl3):δ[ppm]) |
2.1 | - | - | 乙酰基 | 2.15(s),3.05(mc),3.55-3.8(m),5.05(mc),7.05-7.3(m),8.2(d) |
2.对害虫的作用实施例
通过下列试验证实化合物I对害虫的作用:
在试验完成之后,在每种情况下测定与未处理对照相比化合物仍引起50-100%抑制或死亡的最低浓度(极限浓度或最小浓度)。
实施例B.2.1:棉蚜(Aphis gossypii)
通过将侵染的叶片置于试验植物的顶部而将子叶阶段的棉花植物(栽培品种‘Delta Pine’)用约100只实验室饲养的蚜虫侵染。24小时后移走所述叶片。将整个植物的子叶浸入试验化合物的梯度溶液中。5天后相对于对照植物上的死亡率测定被处理植物上的蚜虫死亡率。
在该试验中,与未处理对照相比,实施例1.3的化合物在300ppm下显示出超过80%的死亡率。
实施例B.2.2:桃蚜(Myzus persicae)
通过将侵染的叶片置于试验植物的顶部而将笫2对叶阶段的辣椒植物(栽培品种为‘California Wonder’)用约40只实验室饲养的蚜虫侵染。24小时后移走所述叶片。将整个植物的叶子浸入试验化合物的梯度溶液中。5天后相对于对照植物上的死亡率测定被处理植物上的蚜虫死亡率。
在该试验中,与未处理对照相比,实施例1.3和1.5的化合物在300ppm下显示出超过60%的死亡率。
实施例B.2.3:蚕豆修尾蚜(Megoura viciae)
将活性化合物在1∶3 DMSO∶水中配制。将菜豆叶盘放入填充有0.8%琼脂和2.5ppm OPUSTM的微滴定板中。将叶盘用2.5μl试验溶液喷雾并将5-8只蚜虫成虫放入微滴定板中,然后将微滴定板封闭并在22-24℃和35-45%下保持于荧光下6天。基于活的繁殖蚜虫评价死亡率。试验重复2次。
在该试验中,与未处理对照相比,实施例1.2、1.5和2.1化合物在2500ppm下显示出超过80%的死亡率。
实施例B.2.4:美洲烟叶蛾(烟芽夜蛾(Heliothis virescens))
将活性化合物在1∶3 DMSO∶水中配制。将15-25只卵放入填充有膳食的微滴定板中。用10μl试验溶液喷雾卵,将该板用穿孔箔密封并在27-29℃和75-85%湿度下保持在荧光下6天。基于孵化的幼虫的灵活性和比较进食评价死亡率。试验重复2次。
在该试验中,与未处理对照相比,实施例1.4的化合物在2500ppm下显示出超过80%的死亡率。
Claims (24)
2.如权利要求1所要求的化合物,其中R3和R4均为氢。
3.如权利要求1所要求的化合物,其中R3为氢且R4为C1-C4烷基。
4.如权利要求1-3中任一项所要求的化合物,其中式I中的n为1或2。
5.如权利要求1-3中任一项所要求的化合物,其中式I中的m为1或2。
6.如权利要求4所要求的化合物,其中式I中的m为1或2。
7.一种对抗动物害虫的方法,包括使所述动物害虫,其栖息地,繁殖地,食物供应源,动物害虫生长或可能生长于其中的植物、种子、土壤、区域、材料或环境或需要防止昆虫、蜘蛛或线虫侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的至少一种如权利要求1所定义的式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或至少一种其可农用盐接触。
8.如权利要求7所要求的方法,其中所述害虫为昆虫、蜘蛛或线虫。
9.一种保护作物以防动物害虫侵袭或侵染的方法,包括使作物与杀虫有效量的至少一种如权利要求1-6中任一项所定义的式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或至少一种其可农用盐接触。
10.如权利要求9所要求的方法,其中所述害虫为昆虫、蜘蛛或线虫。
11.一种保护非活体材料以防动物害虫侵袭或侵染的方法,该方法包括使非活体材料与杀虫有效量的至少一种如权利要求1-6中任一项所定义的式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或其可农用盐接触。
12.如权利要求11所要求的方法,其中所述害虫为昆虫、蜘蛛或线虫。
13.如权利要求1-6中任一项所定义的式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物及其可农用盐在对抗动物害虫中的用途。
14.如权利要求1-6中任一项所定义的式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物及其可农用盐在保护作物以防动物害虫侵袭或侵染中的用途。
15.如权利要求1-6中任一项所定义的式I的1-(咪唑啉2-基)氨基-1,2-二苯基乙烷化合物及其可农用盐在保护非活体材料以防动物害虫侵袭或侵染中的用途。
16.一种农用组合物,包含呈现杀虫作用的量的至少一种如权利要求1-6中任一项所定义的式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或至少一种其可农用盐和至少一种惰性固体和/或液体载体以及需要的话至少一种表面活性剂。
17.一种保护种子以防动物害虫并保护秧苗的根和芽以防动物害虫的方法,包括使种子在播种之前和/或催芽之后与如权利要求1-6中任一项所定义的式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物和/或至少一种其可农用盐以杀虫有效量接触。
18.根据权利要求17的方法,其中式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物以0.1g-10kg/100kg种子的量施用。
19.根据权利要求17或18的方法,其中保护由所述秧苗得到的植物的根和芽。
20.根据权利要求17或18的方法,其中保护由所述秧苗得到的植物的芽以防蚜虫。
21.一种包含种子和如权利要求1-6中任一项所定义的式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物或I的可农用盐的组合物,其中每100kg种子,所述式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物或I的可农用盐的存在量为0.1g-10kg。
22.如权利要求1-6中任一项所定义的式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物在保护种子以防土壤害虫并保护所得植物的根和芽以防土壤害虫或叶部害虫中的用途。
23.根据权利要求22的用途,其中式I的1-(咪唑啉2-基)氨基-1,2-二苯基乙烷化合物以0.1g-10kg/100kg种子的量施用。
24.如权利要求1-6中任一项所定义的式I的1-(咪唑啉-2-基)氨基-1,2-二苯基乙烷化合物在保护所得植物的芽以防蚜虫中的用途。
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US68412205P | 2005-05-24 | 2005-05-24 | |
US60/684,122 | 2005-05-24 | ||
US73671405P | 2005-11-15 | 2005-11-15 | |
US60/736,714 | 2005-11-15 | ||
PCT/EP2006/062419 WO2006125748A1 (en) | 2005-05-24 | 2006-05-18 | 1-(imidazolin-2-yl)amino-1,2-diphenylethane compounds for combating animal pests |
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CN101184737B true CN101184737B (zh) | 2012-12-26 |
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DE3908814A1 (de) * | 1989-03-17 | 1990-09-20 | Bayer Ag | Mittel gegen keratinschaedlinge |
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DE3908814A1 (de) * | 1989-03-17 | 1990-09-20 | Bayer Ag | Mittel gegen keratinschaedlinge |
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ZA200711097B (en) | 2009-03-25 |
AP2007004295A0 (en) | 2007-12-31 |
CN101184737A (zh) | 2008-05-21 |
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