CN1132516C - 氨基乙腈衍生物、含该衍生物的农业和园艺杀虫剂及其用途 - Google Patents

氨基乙腈衍生物、含该衍生物的农业和园艺杀虫剂及其用途 Download PDF

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CN1132516C
CN1132516C CN99105289A CN99105289A CN1132516C CN 1132516 C CN1132516 C CN 1132516C CN 99105289 A CN99105289 A CN 99105289A CN 99105289 A CN99105289 A CN 99105289A CN 1132516 C CN1132516 C CN 1132516C
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安藤亘治
三瓶修
坂田和之
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日本农药株式会社
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Abstract

式(I)所示的氨基乙腈衍生物,其中Ar

Description

氨基乙腈衍生物、含该衍生物的农业和园艺杀虫剂及其用途

发明背景相关技术说明日本专利申请公开特开平9-48750(1997)公开了作为农业和园艺杀菌剂的苯基链烷酸酰氨衍生物,日本专利申请公开特开平6-220004(1994)公开了作为产物中间体的N-苯基乙酰氨基腈,以及日本专利申请公开特开平6-263731(1994)、特开平6-271537(1994)和特开平7-252222(1995)公开了与本发明类似的式(I)所示氨基乙腈衍生物。

发明概述为了开发新农业和园艺杀虫剂,本发明人进行了广泛的研究,结果发现式(I)所示的氨基乙腈衍生物是一种新化合物并且具有显著的杀虫效果,以此完成了本发明。

发明详述本发明涉及式(I)所示的氨基乙腈衍生物和含有所述衍生物体作为活性成分的农业和园艺杀虫剂:(其中Ar1和Ar2可以相同或者不同,各表示苯基;具有至少一个取代基的取代苯基,其取代基可以相同或者不同并选自下列取代基:卤原子,硝基,氰基,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C2-C6链烯基,卤代C2-C6链烯基,C2-C6炔基,C3-C6环烷基,C2-C6链烯氧基,卤代C2-C6链烯氧基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷基磺酰氧基,卤代C1-C6烷基磺酰氧基,C1-C6烷基亚磺酰基,卤代C1-C6烷基亚磺酰基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,C2-C6链烯硫基,卤代C2-C6链烯硫基,C2-C6链烯基亚磺酰基,卤代C2-C6链烯基亚磺酰基,C2-C6链烯基磺酰基,卤代C2-C6链烯基磺酰基,C1-C6烷基氨基、二-C1-C6烷基氨基,C1-C6烷基磺酰氨基,卤代C1-C6烷基磺酰氨基,C1-C6烷基羰基,卤代C1-C6烷基羰基,C1-C6烷氧羰基,苯基,至少具有一个取代基的取代苯基,其取代基可以相同或者不同并选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基,苯氧基,在其环上具有至少一个取代基的取代苯氧基,其取代基可以相同或者不同并选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基,苯乙炔基,在其环上具有至少一个取代基的取代苯乙炔基,其取代基可以相同或者不同并选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基,吡啶氧基和在其环上具有至少一个取代基的取代吡啶氧基,其取代基可以相同或者不同并选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基和卤代C1-C6烷基磺酰基;吡啶基;在其环上具有至少一个取代基的取代吡啶基,其取代基可以相同或者不同并选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C2-C6链烯氧基、卤代C2-C6链烯氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C2-C6链烯硫基、卤代C2-C6链烯硫基、C2-C6链烯基亚磺酰基、卤代C2-C6链烯基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、C2-C6链烯基磺酰基、卤代C2-C6链烯基磺酰基、C1-C6烷基氨基和二-C1-C6烷基氨基;

萘基;或在其环上具有至少一个取代基的萘基,其取代基可以相同或者不同并选自卤原子、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C2-C6链烯氧基、卤代C2-C6链烯氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、C2-C6链烯硫基、卤代C2-C6链烯硫基、C2-C6链烯基亚磺酰基、卤代C2-C6链烯基亚磺酰基、C2-C6链烯基磺酰基、卤代C2-C6链烯基磺酰基、C1-C6烷基氨基和二-C1-C6烷基氨基;Q表示基团(其中R1和R2可以相同或者不同,各表示氢原子,卤原子,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C3-C6环烷基或具有至少一个取代基的取代C3-C6环烷基,其取代基可以相同或者不同并选自卤原子和C1-C6烷基,并且R1和R2可以连在一起表示在其链上可具有至少一个取代基的C2-C6亚烷基,所述取代基选自卤原子、C1-C6烷基或C1-C6烷氧基),-CH=CH-或-C≡C-;d是0或者整数1;R3表示氢原子、C1-C6烷基、卤代C1-C6烷基、氰基C1-C6烷基、C1-C6烷硫基、卤代C1-C6烷硫基、C2-C6链烯基或C2-C6炔基;R4、R5、R6、R7和R8可以相同或者不同并且各表示氢原子,卤原子,C1-C6烷基,卤代C1-C6烷基,C3-C6环烷基或具有至少一个取代基的取代C3-C6环烷基,所述取代基可以相同或者不同并选自卤原子和C1-C6烷基,苯基或具有至少一个取代基的取代苯基,所述取代基可以相同或者不同并选自卤原子、硝基、氰基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、C1-C6烷基氨基和二-C1-C6烷基氨基,并且R4和R5一起可以形成C1-C6亚烷基;W是-O-、-S-、-SO2-、或-N(R9)-(其中R9表示氢原子或C1-C6烷基),及a和b可以相同或者不同,表示0或1-4的整数))。

在本发明中,式(I)所示氨基乙腈衍生物的优选取代基包括,例如,作为取代基Ar1和Ar2的苯基,作为Ar1和Ar2环上取代基的卤原子、卤代C1-C6烷基和卤代C1-C6烷氧基,作为取代基R1、R2、R3、R5和R6的氢原子,作为取代基R4的C1-C6烷基,作为取代基Q的-CH2-,作为取代基W的-O-,及a优选为整数1,b优选为O。

本发明式(I)所示的氨基乙腈衍生物包括具有立体异构体的化合物,本发明也包括这些立体异构体。

本发明式(I)所示的氨基乙腈衍生物例如可以通过下面的制备方法制备。其中R3、R4、R5、R6、R7、R8、Ar1、Ar2、Q、W、a、b和d的定义同上,M表示碱金属原子,Hal表示卤原子。)1.式(IV)→式(I)式(I)所示的氨基乙腈衍生物,可以在碱(例如,三乙胺、吡啶等)的存在下,通过式(IV)所示的氨基乙腈衍生物与式(III)所示的酰基卤反应制备。式(I)所示的氨基乙腈衍生物,也可以使用缩合剂(例如,二环己基碳化二亚胺、碘化2-氯-1-甲基吡啶鎓等),通过式(IV)所示的氨基乙腈化合物与式(II)所示的酸的缩合反应制备。式(II)所示的酸可以通过已知方法制备(例如,有机化学杂志(J.Org.Chem.)763,1948,有机合成(累积)(Organic SynthesisColl.),第1卷,436,有机化学杂志(J.Org.Chem.)763,1948,有机合成(累积)(Organic Synthesis Coll.),第1卷,336,拜尔斯坦手册(Beilsteins Handbuch)9,573,拜尔斯坦手册(Beilsteins Handbuch)9,633等)。2.式(VII)→式(IV)制备式(IV)所示的氨基乙腈衍生物,例如,可以通过式(VII)所示的羰基化合物与式(VI)所示的金属氰化物(例如,氰化钠、氰化钾等)和式(V)所示的胺反应。可以使用有机氰化物如三甲硅烷基腈和丙酮合氰化氢作为CN来源。这些反应被称为Strecker反应(例如,C-C键的形成(Formation of C-C Bonds)第1卷,Georg Thieme出版公司,1973年,有机合成(累积)(Organic Synthesis Coll.),第3卷,88等)。

制备式(VII)所示的羰基化合物,也可以使用(例如)下面的制备方法。 其中R3、R4、R5、R6、R7、R8、Ar1、Ar2、a和b的定义同上,L表示离去基团如卤原子、甲磺酰氧基或对甲苯磺酰氧基,W’是OH、SH或NHR9(其中R9的定义同上,Rs是相同或不同的C1-C6烷基及表示C1-C4亚烷基,或者Rs一起形成C1-C4亚烷基。

制备式(VII)所示的羰基化合物,例如,可在碱的存在下,用具有离去基团L的式(VIII-1)所示化合物与式(IX-1)所示化合物反应。

类似地,也可以通过式(VIII-2)所示化合物与式(IX-2)所示化合物反应来制备制备式(VII)所示的羰基化合物。

而且,式(VII)所示的羰基化合物也可以在酸性条件下通过式(XII)所示化合物的去保护反应制备,式(XII)所示化合物是用式(X-1)所示化合物(其羰基以缩醛、缩酮等形式被保护起来)与式(IX-1)所示化合物反应得到的。类似地,式(XII)所示化合物可以通过式(X-2)所示化合物与式(IX-2)所示化合物反应来制备。此外,式(VII)所示羰基化合物可以通过使用合适的氧化剂(例如,高锰酸钾等)氧化式(XIII)所示化合物来制备,式(XIII)所示化合物是通过式(XI-1)所示醇化合物与式(IX-1)所示化合物反应得到的。类似地,式(XIII)所示化合物可以通过式(XI-2)所示醇化合物与式(IX-2)所示化合物反应制备的。

本发明式(I)所示氨基乙腈衍生物的典型化合物如表1、2和3中所示。式(I)表1(R6=R7=R8=H,Q=-C(R1)(R2)-,d=1,b=0(另有描述的除外)

表1(续)

表1(续)

表1(续)

表1(续)

表1(续)

表1(续)

表1(续)

表1(续)

表1(续)

表1(续)

表1(续)

表1(续)

表1(续)

表1(续)

表2(R6=R7=R8=H,b=0)

表3(R6=R7=R8=H,b=0,d=0)

表3(续)

表3(续)

表3(续)

表3(续)

在表1、表2和表3中,Ph表示苯基,Pyr表示吡啶基,Naph表示萘基及c-表示脂环烃。

表4显示的是表1、表2和表3中所列化合物的物理性质。表4

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

表4(续)

在表3或4中,Rf-H或Rf-L表示立体异构体;Rf-H表示在立体异构体中具有较高Rf值的异构体,Rf-L表示具有较低Rf值的异构体。

下面是本发明的典型实施例、制剂实施例和测试实施例。

将4-氯苯氧基乙醛二甲基乙缩醛(1.0g)溶解在丙酮(10ml)中,加入2N盐酸(1.0g),把混合物加热回流8小时。在浓缩反应混合物后,加入水并用乙酸乙酯萃取。用无水硫酸钠干燥萃取液。蒸去溶剂得到4-氯苯氧基乙醛粗产品。

将4-氯苯氧基乙醛粗品(0.5g)、氰化钠(0.17g)和氯化铵(0.27g)加入28%氨水(20ml)中并搅拌2天。向反应溶液中加入乙酸乙酯,用水洗涤反应混合物,用无水硫酸钠干燥并蒸去溶剂。把所得的油状物溶于THF(四氢呋喃)(5ml)中并加入4-氯苯乙酰氯(0.38g)和三乙胺(0.22g)。所得的混合物室温搅拌6小时。向反应混合物中加入水,用乙酸乙酯萃取,用无水硫酸钠干燥萃取液并蒸去溶剂。通过硅胶柱色谱法提纯残余物(乙酸乙酯-己烷),得到目标化合物(0.21g;产率24%;熔点122-128℃)。实施例2第64号化含物的制备将4-氯苯酚(10g)、氯代丙酮(10.8g)、无水碳酸钾(12.9g)和碘化钾(1.3g)加入丙酮(100ml)中并加热回流6小时。过滤反应混合物,浓缩滤液得到4-氯苯氧基丙酮(14g)。

将4-氯苯氧基丙酮(6.0g)、氰化钠(1.91g)和氯化铵(2.6g)加入28%氨水(20ml)中并剧烈搅拌24小时。向反应混合物中加入乙酸乙酯,用水洗涤反应混合物,用无水硫酸钠干燥并蒸去溶剂,得到2-氨基-2-甲基-3-(4-氯代苯氧基)丙腈(6.5g)。

将4-氯苯乙酸(0.4g)加入亚硫酰氯(1ml)中并加热回流1小时,减压蒸去过量的亚硫酰氯。在冰冷却下把所得的酰氯加入到到溶有2-氨基-2-甲基-3-(4-氯苯氧基)丙腈(0.49g)和三乙胺(0.26g)的THF溶液(5ml)中,并在室温下搅拌3小时。向反应混合物中加入水并用乙酸乙酯萃取。用无水硫酸钠干燥萃取液并蒸去溶剂。用己烷-醚洗涤固体残余物,得到目标化合物(0.56g;产率66%;熔点152℃)。实施例3第81号化合物的制备将4-氯苯氧基丙酮(1.84g)、氰化钠(0.5g)、氯化铵(0.9g)溶于甲醇(10ml)中,向其中加入过量的乙胺水溶液。室温搅拌反应混合物2天。在反应结束后,蒸去溶剂并用乙酸乙酯萃取残余物,随后通过普通方法得到2-乙氨基-2-甲基-3-(4-氯苯氧基)丙腈(2.2g)。

将2-乙氨基-2-甲基-3-(4-氯苯氧基)丙腈(0.5g)和4-氯苯乙酰氯(0.38g)溶于THF(10m1)中,向其中加入吡啶(0.16g),把反应混合物加热回流5小时。在冷却至室温后,滤去不溶物并蒸去溶剂。通过硅胶柱色谱法提纯所得的油状物(乙酸乙酯-己烷),得到目标化合物(0.16g;产率20%;熔点83-84℃)。实施例4第166号化合物的制备将4-甲氧基苯乙酸(0.67g)和碘化2-氯-1-甲基吡啶(1.10g)悬浮分散在THF(10ml)中,室温下向其中再室温滴加三乙胺(0.50g)。搅拌5分钟后,加入2-氨基-2-甲基-3-(4-氯苯氧基)丁腈(0.90g)并搅拌所得的混合物6小时。在反应结束后,滤去不溶物并蒸去溶剂。通过硅胶柱色谱法提纯残余物(乙酸乙酯-己烷),得到目标化合物(0.78g;产率52%;熔点129-131℃)。实施例5第253号化合物的制备将盐酸2-(5-三氟甲基-2-吡啶基)乙酸(0.74g)、2-氨基-2-甲基-3-(4-三氟甲基苯氧基)丙腈(0.65g)、碘化2-氯-1-甲基吡啶(1.17g)和三乙胺(0.93g)加入乙腈(10ml)中并加热回流6小时。向反应混合物中加入水并用乙酸乙酯萃取,用无水硫酸钠干燥。随后,蒸去溶剂。通过硅胶柱色谱法提纯残余物(乙酸乙酯-己烷),得到目标化合物(0.34g;产率28%;熔点97-99℃)。实施例6第288号化合物的制备将3-苯基丙炔酸(0.28g)、2-氨基-2-甲基-3-(4-氯苯氧基)丙腈(0.40g)和二环己基碳化二亚胺(0.41g)溶于二氯甲烷(5ml)中并把溶液加热回流8小时。过滤反应混合物,浓缩滤液。通过硅胶柱色谱法提纯残余物(乙酸乙酯-己烷),得到目标化合物(0.11g;产率17%;糊状)。

包含本发明式(I)所示的氨基乙腈衍生物作为活性成分的农业和园艺杀虫剂,适于防治农业、林业、园艺、储藏品中的各种害虫及对水稻、果树、蔬菜、其他作物和花卉有害的寄生虫或线虫。它对各种害虫具有很强的杀虫效果,例如,鳞翅目害虫如桔黄小卷叶蛾(Adoxophyesoranafasciata)、茶小卷叶蛾(Adoxophyessp.)、苹小食心虫(Grapholitainopinata)、梨小食心虫(Grapholitamolesta)、大豆食心虫(Leguminivoraglycinivorella),桑卷叶蛾(Olethreutesmori)、茶叶细蛾(Caloptiliathevivora)、猛花细蛾Caloptiliazachrysa、窄翅潜叶蛾(Phyllonorycterringoniella)、梨潜叶细蛾(Spulerrinaastaurota)、菜粉蝶(Piersrapaecrucivora)、棉铃虫(Heliothissp.)、苹果小卷蛾(Laspeyresiapomonella)、菜蛾(Plutella xylostella)、苹果银蛾(Argyresthiaconjugella)、桃小食心虫(Carposinaniponesis)、二化螟(Chilosuppressalis)、稻纵卷叶野螟(Cnaphalocrocismedinalis)、烟草粉斑螟(Ephestiaelutella)、桑螟(Glyphodespyloalis)、三化螟(Scirpophagaincertulas)、稻苞虫(Parnaraguttata)、眉纹夜蛾(Pseudaletiaseparata)、大螟(Sesamiainferens)、斜纹夜蛾(Spodopteralitura)、甜菜夜蛾(Spodopteraexigua);半翅目害虫如紫箢叶蝉(Macrostelesfascifrons)、稻大白叶蝉(Nephotettixcincticeps)、稻褐飞虱(Nilaparvatalugens)、白背飞虱(Sogatellafurcifera)、桔木虱(Diaphorinacitri)、日本葡萄粉虱(Aleurolobustaonabae)、棉粉虱(Bemisiatabaci)、温室粉虱(Trialeurodesvaporariorum)、萝卜蚜(lipaphiserysimi)、桃蚜(Myzuspersicae)、角盘蚧(Ceroplastesceriferus)、桔绵蜡蚧(Pulvinariaaurantil)、樟圆蚧(Pseudaonidiaduplex)、梨圆蚧(Comstockaspisperniciosa)、矢尖蚧(Unaspisyanonesis);鞘翅目害虫如红铜丽金龟(Anomalarufocunrea)、日本丽金龟(Popilliajaponica)、烟草甲(Lasiodermaserricorne)、欧洲竹粉蠹(Lyctusbrunneus)、马铃薯瓢虫(Epilachaavigintiotopunctata)、绿豆象(Callosobruchuschinensis)、蔬菜象甲(Listroderescostirostris)、玉米象(Sitophiluszeamais)、棉铃象(Anthonomusgradisgradis)、稻象甲(Lissorhoptrusoryzophilus)、黄守瓜(Aulacophorafemoralis)、稻负泥虫(Oulemaoryzae)、黄曲条跳甲(Phyllotretastriolata)、纵坑切梢小蠹(Tomicuspiniperda)、马铃薯甲虫(Leptinotarsadecemlineata)、墨西哥豆瓢虫(Epilachnavarivestis)、南瓜十二星叶甲(Diabroticasp.);双翅目害虫如瓜实蝇(Dacus(Zeugodacus)cucurbitae)、桔小实蝇(Dacus(Bactrocera)dorsalis)、日本稻潜蝇(Agromyzaoryzae)、葱蝇(Deliaantiqua)、种蝇(Deliaplatura)、大豆荚瘿蚊(Asphondyliasp.)、家蝇(Muscadomestica)、库蚊(Culexpipiens);垫刃目害虫如根腐线虫(Pratylenchussp.)、马铃薯金线虫(Globoderarostochiensis)、根疣线虫属(Meloidogynesp.)、半穿刺线虫(Tylenchulussemipenetrans)、Aphelenchusavenae.菊叶芽滑刃线虫(Aphelenchoidesritzemabosi)。

含有本发明式(I)所示氨基乙腈衍生物的农业和园艺杀虫剂对上面提到的害虫具有显著的防治效果,这些害虫对稻田作物、农作物、果树、蔬菜和其他作物及花卉有害,在预计害虫会出现及害虫出现前或出现后,用本发明的农业和园艺杀虫剂适时地对诸如稻田水、茎和叶或者土壤、农场、果树、蔬菜、其他作物和花卉进行处理,会得到理想的效果。

根据农药在使用前惯用的调配方法,本发明农业和园艺杀虫剂通常被调配成适当的制剂以便于使用。

这就是,用适当量的式(I)所示氨基乙腈衍生物与合适的惰性载体混合,若需要可加入辅助剂,进行溶解、分散、悬浮、混合、浸渍、吸收或者吸附,把混合物调配成悬浮液、乳液、液体、可湿性粉剂、颗粒剂、粉剂、片剂等。

在本发明中使用的惰性载体可以是任何固体或液体。使用的固体载体材料包括,例如,豆粉,谷物粉末,木粉,树皮粉末,锯屑,烟草梗粉末,胡桃壳粉,麦麸,纤维素纤维,植物提取残余物,合成聚合物如粉状合成树脂,粘土(例如,高岭土、膨润土、酸性粘土等),滑石类(例如,滑石、叶蜡石等),硅石(例如,硅藻土、石英砂、云母、白炭黑(细碎的水合二氧化硅,也称作水合硅酸,包含高分散性硅酸;一些产品是以硅酸钙为主要组分),活性炭,硫粉,浮石,煅烧过的硅藻土,碎砖,飘尘和砂,无机矿物粉末如碳酸钙、磷酸钙,化肥或者硫酸铵、磷酸铵、硝酸铵、尿素、氯化铵的混合肥料。这些载体可以单独或以两种或多种混合物的形式使用。

液体载体包括本身具有溶解作用的物质和本身虽不具有溶解作用但借助于辅助剂能够分散活性成分的物质。典型实例包括下列载体,这些载体可以单独或以两种或多种混合物的形式使用,例如,水,醇类(例如,甲醇、乙醇、异丙醇、丁醇、1,2-亚乙基二醇等),酮类(例如,丙酮、甲基乙基酮、甲基异丁基酮、二异丁基酮、环己酮等),醚类(例如,乙醚、二恶烷、乙二醇-乙醚、二丙醚、四氢呋喃等),脂族烃(例如,煤油、矿物油等),芳族烃(例如,苯、甲苯、二甲苯、溶剂石脑油、烷基萘等),卤代烃(例如,二氯乙烷、氯仿、四氯化碳、氯苯等),酯类(例如,乙酸乙酯、邻苯二甲酸酯、邻苯二甲酸二异丙酯、邻苯二甲酸二丁酯、邻苯二甲酸二辛酯等),酰胺类(例如,二甲基甲酰胺、二乙基甲酰胺、二甲基乙酰胺等),腈类(例如,乙腈等),二甲亚砜,等等。

其他辅助剂包括下面列举的这些具有代表性的辅助剂。依使用的目的而定,这些辅助剂可以单独使用,或者两种或多种结合起来使用。或者,在一些情况下也可以不用辅助剂。

使用表面活性剂的目的是为了乳化、分散、溶解和/或润湿活性成分。表面活性剂的实例包括,例如,聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯高级脂肪酸酯、聚氧乙烯树脂酸酯、聚氧乙烯脱水山梨糖醇一月桂酸酯、聚氧乙烯脱水山梨糖醇一油酸酯、烷芳基磺酸盐、萘磺酸缩合物、木素磺酸盐、高级醇硫酸盐,等等。

辅助剂也可以用于稳定活性成分化合物及粘合或束缚活性成分化合物。这样辅助剂的实例包括酪蛋白、明胶、淀粉、甲基纤维素、羧甲基纤维素、阿拉伯树胶、聚乙烯醇、松节油、米糠油、膨润土、木素亚硫酸盐废液,等等。

辅助剂可以作来改善固体产物的流动性。这样辅助剂的实例是,例如,蜡、硬脂酸酯、磷酸烷基酯,等等。

辅助剂如萘磺酸缩合物、缩聚磷酸盐等可作为悬浮产物的抗絮凝剂使用。

辅助剂如硅油可作为消泡剂使用。

如果需要,可以调整活性成分化合物的量。例如,在粉剂和颗粒剂中,其合适的含量是0.01-50wt%。在乳剂和可温性粉剂中,其合适的含量也是0.01-50wt%。

为了防治各种病害,对于预计会出现害虫的作物或不希望有害虫出现的场所,可以施用有效量的本发明农业和园艺杀虫剂(适当地用水等稀释或者悬浮在水或其类似物中)来预防虫害。

本发明农业和园艺杀虫剂施用量的变化,取决于诸如施用目的、被防治的害虫、作物生长状态、害虫出现趋势、天气、环境条件、制剂形式、施用场所、施用地点、施用时期等各种因素。然而,施用量若以活性成分化合物的量来表示,视目的而定应该适当地选择在0.1g-10kg/10acres范围内。

为了进一步扩展可防治的病害和害虫、最佳防治时间或者减少施用剂量,本发明的农业和园艺杀虫剂可以与其他农业和园艺病害虫害防治剂结合使用。

下面给出了本发明的典型实例和测试实例。然而,本发明决不受此限制。

在下面的制剂中,所有的份数是指重量份数。制剂实施例1

表1、2或3中所述化合物              50份二甲苯                             40份聚氧乙烯壬基苯基醚和烷基苯磺酸钙的混合物             10份将上面提到的各种组分均匀混合并溶解,制成乳剂。制剂实施例2表1、2或3中所述化合物              3份粘土粉                             82份硅藻土粉                           15份将上面提到的各种成分均匀混合并磨成粉状,制成粉剂。制剂实施例3表1、2或3中所述化合物              5份膨润土和粘土粉末                   90份木素磺酸钙                         5份将上述各种成分均匀混合并与适量的水捏合,将所得的混合物造粒并干燥得到颗粒剂。制剂实施例4表1、2或3中所述化合物              20份高岭土和高分散性合成硅酸           75份聚氧乙烯壬基苯基醚和烷基苯磺酸钙的混合物             5份将上面提到的各种成分均匀混合并磨成粉状,制成可湿性粉剂。测试实施例1对菜蛾(Plutella xylostella)的杀虫效果将菜蛾(Plutella xylostella)成虫放置在白菜幼苗上喂养并使其产卵,在喂养开始2天后,把产有虫卵的白菜幼苗用化学液浸渍30秒,这种化学液是把包含有表1、表2或表3所述化合物的化学试剂稀释至500ppm制备而成的。风干后,把幼苗放置在温度25℃的温室里。在化学溶液中浸渍后再过6天,检查孵化的昆虫。通过下式计算昆虫死亡率并根据下面标准进行判定。1组,10只昆虫,3个系列体系。

校正的昆虫的死亡率(%)未处理组孵化的昆虫的数目-处理组孵化的昆虫的数目未处理组孵化的昆虫的数目评价标准:A:昆虫死亡率  100%B:昆虫死亡率  99-90%C:昆虫死亡率  89-80%D:昆虫死亡率  79-50%得到的结果如表5中所示。测试实施例2对茶小卷叶蛾(Adoxophyes sp.)的杀虫效果将茶(品种:Yabukita)的叶子在化学液中浸渍30秒,这种化学液是把含有表1、表2或表3所述化合物的化学试剂稀释至500ppm制备而成的。风干后,将其放在直径9cm的塑料盘中,用第2龄的茶小卷叶蛾幼虫(Adoxophyes sp.)对其进行接种。此后,用盖子把塑料盘盖上并放置在温度25℃和湿度70%的温室里。接种8天后,检查昆虫的死亡数并根据测试实施例1进行评价。1组,10只昆虫,3个系列体系。

得到的结果如表5中所示。表5

表5(续)

表5(续)

表5(续)

Claims (5)

1.式(I)所示的氨基乙腈衍生物:其中Ar1和Ar2可以相同或者不同,各表示苯基;具有1-5个取代基的取代苯基,其取代基可以相同或者不同并选自卤原子,硝基,氰基,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C2-C6链炔基,C2-C6链烯氧基,卤代C2-C6链烯氧基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,C2-C6链烯硫基,卤代C2-C6链烯硫基,C2-C6链烯基磺酰基,卤代C2-C6链烯基磺酰基,二-C1-C6烷基氨基,C1-C6烷基磺酰氨基,卤代C1-C6烷基磺酰氨基,C1-C6烷基羰基氧基,卤代C1-C6烷基羰基氨基,C1-C6烷氧羰基,苯基,苯氧基,苯乙炔基,吡啶氧基,和在其环上具有1-4个取代基的取代吡啶氧基,其取代基可以相同或者不同并选自卤原子、卤代C1-C6烷基;吡啶基;在其环上具有1-4个取代基的取代吡啶基,其取代基可以相同或者不同并选自卤原子、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、卤代C1-C6烷硫基、C1-C6烷基磺酰基;萘基;或Q表示基团其中R1和R2可以相同或者不同,各表示氢原子,C1-C6烷基,C1-C6烷氧基,并且R1和R2可以连在一起表示C2-C6亚烷基,-CH=CH-或-C≡C-;d是0或者整数1;R3表示氢原子、C1-C6烷基、C2-C6链炔基或C3-C6环烷基;R4表示氢原子、C1-C6烷基、或三氟甲基;R5表示氢原子或C1-C6烷基;R6表示氢原子;R7表示氢原子或甲基;R8表示氢原子;并且R4和R5-起可以形成C1-C6亚烷基;W是-O-、-S-、-SO2-或-N(R9)-,其中R9表示氢原子或C1-C6烷基,以及a是1-4的整数,b是0或1-4的整数。
2.根据权利要求1的氨基乙腈衍生物,其中Ar1和Ar2表示苯基;具有1-5个取代基的取代苯基,其取代基可以相同或者不同并选自下列基团卤原子,氰基,硝基,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C2-C6链烯氧基,卤代C2-C6链烯氧基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,C2-C6链烯硫基,卤代C2-C6链烯硫基,C2-C6链烯基磺酰基,卤代C2-C6链烯基磺酰基,二-C1-C6烷基氨基,C1-C6烷基磺酰氨基,卤代C1-C6烷基磺酰氨基,C1-C6烷基羰基氧基,卤代C1-C6烷基羰基氨基,C1-C6烷氧羰基,苯基,苯氧基,苯乙炔基,吡啶氧基,和在其环上具有1-4个取代基的取代吡啶氧基,其取代基可以相同或者不同并选自卤原子、卤代C1-C6烷基;吡啶基;在其环上具有1-4个取代基的取代吡啶基,其取代基可以相同或者不同并选自卤原子、卤代C1-C6烷基、卤代C1-C6烷氧基和卤代C1-C6烷硫基,萘基;和Q表示基团其中R1和R2可以相同或者不同并且各表示氢原子,C1-C6烷基或C1-C6烷氧基,以及R1和R2可以连在一起表示C2-C6亚烷基,-CH=CH-或-C≡C-;d是0或者整数1;R3表示氢原子、C1-C6烷基、C2-C6链炔基或C3-C6环烷基;R4表示氢原子、C1-C6烷基、或三氟甲基;R5表示氢原子或C1-C6烷基;R6表示氢原子;R7表示氢原子或甲基;R8表示氢原子;W是-O-、-S-、-SO2-或-N(R9)-,其中R9表示氢原子或C1-C6烷基,以及a是1-4的整数,b是0或1-4的整数。
3.根据权利要求2的氨基乙腈衍生物,其中Ar1和Ar2表示苯基;具有1-5个取代基的取代苯基,其取代基可以相同或者不同并选自下列基团卤原子,氰基,硝基,C1-C6烷基,卤代C1-C6烷基,C1-C6烷氧基,卤代C1-C6烷氧基,C2-C6链烯氧基,卤代C2-C6链烯氧基,C1-C6烷硫基,卤代C1-C6烷硫基,C1-C6烷基磺酰基,卤代C1-C6烷基磺酰基,C2-C6链烯硫基,卤代C2-C6链烯硫基,C2-C6链烯基磺酰基,卤代C2-C6链烯基磺酰基,C1-C6烷氧羰基,苯基,苯氧基,苯乙炔基,吡啶氧基,和在其环上具有1-4个取代基的取代吡啶氧基,其取代基可以相同或者不同并选自卤原子、卤代C1-C6烷基;吡啶基;在其环上具有1-4个取代基的取代吡啶基,其取代基可以相同或者不同并选自卤原子、卤代C1-C6烷基、卤代C1-C6烷氧基、卤代C1-C6烷硫基;萘基;或Q表示基团其中R1和R2可以相同或者不同并且各表示氢原子,C1-C6烷基或C1-C6烷氧基,并且R1和R2可以连在一起表示C2-C6亚烷基,-CH=CH-或-C≡C-;d是0或者整数1;R3表示氢原子、C1-C6烷基或C2-C6链炔基;R4表示氢原子、C1-C6烷基、或三氟甲基;R5表示氢原子或C1-C6烷基;R6表示氢原子;R7表示氢原子或甲基;R8表示氢原子;W是-O-、-S-、-SO2-或-N(R9)-,其中R9表示氢原子或C1-C6烷基,以及a是1-4的整数,b是0或1-4的整数。
4.包含权利要求1-3任一项的氨基乙腈衍生物作为活性成份的农业和园艺农药。
5.所述农业和园艺农药的使用方法,该方法包括将有效量的如权利要求4所述的农业和园艺农药施用于有用植物以保护有用的植物。
CN99105289A 1998-05-01 1999-04-30 氨基乙腈衍生物、含该衍生物的农业和园艺杀虫剂及其用途 CN1132516C (zh)

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