CN1056958C - 杀虫剂组合物及其应用 - Google Patents

杀虫剂组合物及其应用 Download PDF

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CN1056958C
CN1056958C CN90108265.1A CN90108265A CN1056958C CN 1056958 C CN1056958 C CN 1056958C CN 90108265 A CN90108265 A CN 90108265A CN 1056958 C CN1056958 C CN 1056958C
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methyl
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CN1050714A (zh
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石光圭一
铃木顺次
大石治仁
山田富夫
波多野连平
高草伸生
满井顺
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Nippon Soda Co Ltd
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Abstract

本发明涉及具有如下分子式的且具有优异杀虫活性的化合物和它的盐：
其中R1、R2、R3、R4、R5、X、Y、Z和n均如说明书中所描述。

Description

杀虫剂组合物及其应用
本发明涉及杀虫剂组合物及其应用，特别是涉及含新的胺衍生物的杀虫剂组合物及其应用。
经过多年对于杀虫剂的研究和发展，很多化学物质，例如有机含磷杀虫剂(如硝苯硫磷酯和马拉硫磷)和氨甲酸酯杀虫剂(如甲氨甲酸萘酯和甲氨叉威(灭多虫))已经发展并投入实际应用。这些杀虫剂为提高农业产量已经起了很大的作用。但是，近年来由于诸如因残余物或累积物引起的环境污染或由于长期使用的结果导致害虫产生抗药的问题，这些杀虫剂中的一部分被限制使用。因此，就需要发展一类新的化学物，它们对于各类害虫(包括这些有抗性的害虫)均有优良的杀虫特性，并且它们能够被安全地使用。
下面的化合物已知是本发明的化合物的类似物，但它无杀虫活性。
Figure C9010826500041
(Boll，Chim.Farm.，1979 118(11)661-666)此外，在USP4918088中所描述的下列化合物具有杀虫活性。
Figure C9010826500042
尽管该化合物显示出抗棉蚜虫的活性，但是，它对于鳞翅目昆虫和(绿色)稻微叶蝉(它们对于作物是十分有害的害虫)是没有杀虫活性的。
本发明的目的是提供能容易地进行工业合成的农用化学物，它们具有一定的效应并能安全地使用。
本发明的化合物对于鳞翅目和半翅目昆虫均具有高的杀虫活性。
本发明涉及杀虫剂组合物，它的活性成分为如下分子式表示的化合物或它的盐：
Figure C9010826500051
式中R1选自被甲基、氟、氯、溴取代的吡啶基，未取代的2-吡啶基除外；
X表示C1-3亚烃基；
R2选自氢；氨甲酰基；一或二C1-5烷基氨甲酰基；硫代氨甲酰基；一或二C1-5烷基硫代氨甲酰基；氨磺酰基；一或二C1-5烷基氨磺酰基；可被氟、甲氧基、甲硫基、乙氧基羰基、氰基、苯基、氯代苯基、甲氧基苯基、呋喃基、噻吩基、吡啶基、氯代吡啶基、噻唑基或氯代噻唑基取代的C1-5烷基；C2-5链烯基；C2-5炔基；C3-8环烯基；芳基；或-Y-R5；
其中Y表示O、S(O)n、CO、CS或CO2；n表示0、1或2；
R5代表氢、C1-5烷基、C2-5链烯基、C2-5炔基、C3-8环烷基、C3-8环烯基或芳基；
R3代表氢；可被F、Cl、甲氧基、甲硫基、乙氧基羰基、氰基、苯基、氯代苯基、甲氨基、二甲氨基、氰亚氨基、氯代吡啶甲基氨基、或N-甲基-N-氯代吡啶甲基氨基取代的C1-5烷基；C2-5链烯基；C2-5炔基；C3-8环烯基；
R4表示氰基或硝基；Z表示N。
本发明也涉及该杀虫剂组合物在控制鳞翅目和半翅目昆虫中的应用。
本发明的化合物可以根据下面的反应方法制备：
(1)制备方法1：其中r1和r2代表C1-5烷基；R1、R2、R3、R4和X如上所定义。
反应在惰性有机溶剂中进行，较佳是在芳香烃溶剂，如二甲苯、甲苯或苯中，在酸性催化剂，如对甲苯磺酸存在下进行，如果需要，可在回流条件下进行。
(2)制备方法2：
Figure C9010826500062
其中r3代表C1-5烷基；R1、R2、R3和X如上所定义。该反应在惰性有机溶剂，较佳是在醇(如甲醇、乙醇)中，在室温和所用的溶剂的沸点之间的温度下进行。(3)制备方法3：
Figure C9010826500071
其中Hal代表卤素；R1、R2、R3和X如上所定义。
该反应在惰性有机溶剂，较佳是DMF、THF、苯乙腈、丙酮、甲乙酮中，在酸受体，例如碳酸钾、NaH、三乙胺存在下，在室温和所用的溶剂的沸点之间的温度下进行。(4)制备方法4：
Figure C9010826500072
其中R1、R2、R3、X和Hal如上所定义。该反应以与制备方法3相同的方法进行。(5)制备方法5：
Figure C9010826500081
其中R1、R2、R3和X如上所定义。该反应在惰性有机溶剂，较佳是乙腈、四氯化碳、二氯乙烷中，在硝化反应剂，如四氟硼酸硝鎓存在下，在-20℃和所用溶剂的沸点之间的温度下进行。
反应完成后，经过一般的后处理而得到所需要的化合物。本发明的化合物的结构通过诸如红外(IR)、核磁(NMR)、质谱(MASS)的方法来测定。
当本发明的化合物中R2是氢时，可以存在由
Figure C9010826500082
所代表的互变异构体。由
Figure C9010826500083
(当Z代表N时)  所代表的顺式异构体和(当Z代表CH时)反式-顺式异构体。比率根据诸如仪器分析的条件而变化。
下面的实例列举了本发明。实例1：2-(2-氯-5-吡啶甲基氨基)-1-硝基-1-丁烯
Figure C9010826500091
在50ml甲苯中，将4.2g2-氯-5-吡啶甲胺、3.5g1-硝基-2-丁酮和0.1g。对甲苯磺酸相混合将该混合物回流2小时，然后蒸馏去除该溶剂，残余物通过硅胶柱层析纯化而获得4.1g化合物No.368。m.p.95-98℃。实例2：2-(2-氯-5-吡啶甲基氨基)-1-氰基-1-丙烯
Figure C9010826500092
将1.4g2-氯-5-吡啶甲胺和0.8g1-氰基-2-丙酮相混合，将混合物在室温下搅拌过夜。然后蒸馏去除溶剂，残余物通过硅胶柱层析纯化而获得1.7g化合物No.528。m.p.95-98℃。实例3：N-氰基-N′-(2-氯-5-吡啶甲基)-N′-甲基乙脒。
Figure C9010826500093
在20ml乙醇中，将1.6g N-甲基-2-氯-5-吡啶甲胺和1.2g乙基-N-氰基乙脒相混合，将混合物在室温下搅拌过夜。然后蒸馏去除溶剂，残余物通过硅胶柱层析纯化而获得1.8g化合物No.22。m.p.101-103℃。实例4：N-氰基-N′-(2-氯-5-吡啶甲基)-N′-乙基乙脒：
在冰浴温度下，将0.7g氢化钠(纯度为60％)加入至含有3.0g N-氰基-N′-(2-氯-5-吡啶甲基)乙脒的20ml N′N-二甲基甲酰胺溶液中。在将其搅拌1小时后，将2.7g乙基碘加入该混合物，接着在室温下搅拌5小时。然后将反应混合物倾倒入冰水中，用乙酸乙酯抽提，通过无水硫酸镁干燥并在减压下浓缩。所得到的残余物通过硅胶柱层析纯化而获得1.6化合物No.51。m.p.100-101℃。实例5：N-氰基-N-(2-氯-5-吡啶甲基)-N′-甲基乙脒：
Figure C9010826500102
在冰浴温度下，将0.6g氢化钠(纯度60％)加入含1.3gN-氰基-N′-甲基乙脒的20ml N，N′-二甲基甲酰胺溶液中。在相同的温度下搅拌1小时后，将2.2g2-氯-5-吡啶甲基氯加入至混合物，接着在室温下搅拌5小时。然后将反应混合物倾注入冰水中，用乙酸乙酯抽提，用无水硫酸镁干燥并在减压下浓缩。所得到的残余物通过硅胶柱层析纯化而获得1.5g化合物No.22。m.p.101-103℃。对照实例：N-(2-氯-5-吡啶甲基)-N-甲基乙脒盐酸盐：
Figure C9010826500111
在0℃下，将5.1gN-(2-氯-5-吡啶甲基)-N-甲胺加入至40ml乙醇中，然后加入4g乙基乙脒盐酸盐。搅拌1小时后，使反应混合物升温至室温并搅拌过夜。然后蒸馏去除溶剂。用二乙醚洗涤白色残余物而获得7.3g标题化合物。m.p.192-197℃。实例6：N-(2-氯-5-吡啶甲基)-N-甲基-N′-硝基乙脒
Figure C9010826500112
在氮气氛和室温下，往含1gN-(2-氯-5-吡啶甲基)-N-甲脒盐酸盐的10ml无水丙腈的悬浮液中逐滴加入0.7g DBU。搅拌30分钟后，在氮气氛和用冰水冷却下，将该溶液逐滴加入至含0.6g四氟硼酸硝鎓的5ml无水丙腈悬浮液中并搅拌4小时。此后，将混合物倾注入冰水中，然后用氯仿抽提数次。合并的氯仿层通过用硫酸镁干燥，过滤并蒸馏。通过硅胶柱层析纯化粗油而获得0.3g化合物No.236。ND 251.5808
包括上述化合物在内的本发明的典型实例列于表1中。
            表1
Figure C9010826500171
Figure C9010826500191
Figure C9010826500211
Figure C9010826500221
Figure C9010826500231
Figure C9010826500241
Figure C9010826500261
Figure C9010826500271
Figure C9010826500281
Figure C9010826500291
Figure C9010826500301
Figure C9010826500311
Figure C9010826500321
Figure C9010826500331
Figure C9010826500341
Figure C9010826500371
Figure C9010826500381
Figure C9010826500401
Figure C9010826500411
Figure C9010826500421
Figure C9010826500441
Figure C9010826500451
Figure C9010826500471
Figure C9010826500481
Figure C9010826500491
Figure C9010826500511
Figure C9010826500521
Figure C9010826500531
Figure C9010826500551
Figure C9010826500591
Figure C9010826500601
Figure C9010826500611
Figure C9010826500641
Figure C9010826500651
Figure C9010826500661
Figure C9010826500671
Figure C9010826500691
Figure C9010826500701
*11H-NMR(CDCl3)δ；ppm 3.32(s，3H)，4.63(s，2H)，7.37(d，1H)，7.62(dd，1H)，
                   8.37(d，1H)
本发明的化合物显示出高的杀虫活性，可以抗各种害虫，例如切根虫、菜蛾、蚜虫、微叶蝉和飞虱。近年来，由于对杀虫剂的抗性的增加而引起的有机含磷和氨甲酸酯杀虫剂的控制效应的减少已成为严重的问题。在这种情况下，就需要发展对于具有抗性的害虫有效的新的杀虫剂。本发明的杀虫剂具有卓越的杀虫活性，不仅能抗敏感病株，而且能抗抗药性株。
本发明的杀虫剂含有作为活性成份的由通式(1)所表示的一种或多种类型的化合物。这些活性成分可以作为产品使用，通常它们以一般农药可采用的任何形式而使用，例如呈可湿性粉、粉尘剂，可乳化的浓缩物、悬浮浓缩物、烟熏化合物、熏蒸剂、颗粒剂或其它制剂。当采用固体制剂时，大豆粉、小麦粉或其它植物粉、硅藻土、磷灰石、石膏、滑石、叶蜡石、粘土或其它细矿物粉剂被用作添加剂和载体。
当采用液体制剂时，则煤油、矿物油、石油、石脑油溶剂、二甲苯、环己烷、环己酮、二甲基甲酰胺、二甲基亚砜、乙醇、丙酮、水等可用作为溶剂。如果需要的话，可加入表面活性剂以给出均相和适宜的配方。在真正喷洒到大田里的植物上以前，用水稀释这样获得的可湿性粉末、可乳化的浓缩物、悬浮浓缩物等至所规定浓度的悬浮液或乳化液。在采用粉尘剂或颗粒时，可将它们直接使用而不需要进一步加工。
这并不是说本发明的化合物即使单独使用也是有效的，但它可以通过与各类杀虫剂、杀螨剂和杀真菌剂混合而使用。
可以与本发明的化合物混合而使用的杀螨剂和杀虫剂的典型实例描述如下：杀螨剂(杀真菌剂)：氯化二(对溴苯基)乙醇酸酯、氯丙酯、双氯苯环丙醇、溴丙酯、三氯杀螨醇、敌螨通、乐杀螨、杀虫脒、二甲苯胺脒、克螨特、PPPS、苯并噁嗪酯、hexythiazox、六苯丁锡氧、多萘菌素、灭螨猛、三硫喹恶啉、chlorfenson、四氯杀螨砜、苯丙氧、阿凡曼菌素、clorfentezine、flubenzimine、fenazaquin、pyridaben、fenproximate、杀螨醇、甲基苯硫脲酯、苯菌灵、双硫胺甲酰、iprobenfos、克瘟散、fthalide、噻菌灵、富士一号、chorethalonil、克菌丹、多氧菌素B、杀稻瘟菌素、春雷菌素、有效霉素、三环唑、pyroquilon、吩嗪氧化物、溴丙巴比妥(mepronil)、flutolanil、pencycuron、二氯苯基甲乙基二氧咪唑烷羧酰胺、hymexazole、metalaxyl、triflumizole、diclomezine、tecloftalam、vinclozolin、procymidone、bitertanol、triadimefon、prochloraz、pyrifenox、fenarimal、renpropimorph、嗪氨灵、metalaxyl、氧化萎锈灵、pefrazoate、diclomedine、fluazinam、oxadixyl、ethoquinolac、TPTH、propamocarb、fosetyl、双氢链霉素、敌菌灵、二噻农、diethofencarb；有机含磷型和氨甲酸酯型杀虫剂(杀螨剂)：倍硫磷、杀螟松、二嗪农、毒死蜱、oxydeprofos、蚜灭多、稻丰散、乐果、安果、马拉硫磷、敌百虫、甲基乙拌磷、亚胺硫磷、灭蚜松、敌敌畏、高灭磷、EPBP、氯亚磷(dialifos)、甲基对硫磷、甲基砜吸磷、乙硫磷、涕灭威、残杀威、灭多虫、fenobucarb、BPMC、pyraclofos、久效磷、杀抗松、巴丹、虫螨威、benfuracarb、metolcarb、西维因、抗蚜威、杀虫丹、fenoxycarb；拟除虫菊酯类杀虫剂(杀螨剂)：苄氯菊酯、cypermethrin、deltamethrin、fenvalerate、fenpropathrin、除虫菊酯、丙烯除虫菊素、似虫菊、苄呋菊酯、parthrin、苄菊酯、扑虫菊、bifenthin、消虫菊、fluvalinate、cyfluthrin、cyhalothrin、flucythrinate、ethofenprox、环消虫菊、tralomethrin、silaneophan；苯甲酰苯基脲类和其它类杀虫剂：diflubenzuron、chlorfuazuron、triflumuron、teflubenzuron、buprofezin、pyriproxyfen、flufenoxuron、机油(Machine oil)；
下面给出了相同的制剂实例。但是所加的载体、表面活性剂等不受这些实例的限制。实例7：可乳化的浓缩物
    本发明的化合物                   10份
    烷苯基聚氧乙烯                   5份
    二甲基甲酰胺                     50份
    二甲苯                           35份
将这些组分混合并溶解，为了可喷洒使用，将液体混合物用水稀释成乳化液。实例8：可湿性粉剂
   本发明的化合物                         20份
   高级醇硫酸酯                           5份
   硅藻土                                 70份
   二氧化硅                               5份
将这些化合物混合并研磨成细粉，为了可以喷洒使用，用水将其稀释成悬浮液。          -实例9：粉尘剂
   本发明的化合物                5份
   滑石                          94.7份
   二氧化硅                      0.3份
将它们混合并研磨并以磨粉形式喷洒。实例10：颗粒
本发明的化合物                        5份
粘土                                  73份
膨润土                                20份
二辛基磺基琥珀酸钠                    1份
磷酸钠                                1份
将上述化合物制成颗粒，并以颗粒形式使用。
下面的试验显示了本发明的化合物的杀虫活性。试验1：对棉蚜的效应
用小刷子往每一个缽中将30-50条棉蚜虫接到种植于直径10cm的缽中，发芽后10天龄的黄瓜叶子上。一天后，除去伤亡的害虫，用上述杀虫剂实例中实例7中所描述的可乳化的浓缩物用水稀释至化合物的浓度为125ppm(如所描述的)所制得的化合物溶液进行喷洒。将缽置于温度为25℃，湿度65％的暖房中。7天后清点剩余的害虫的数目，通过与未经处理的缽中的害虫数相比较而计算控制效率。结果示于表2中。
                 表2
    化合物No.     控制效率(7天后)
    125ppm
    12    -34681016     100％100100100100100100100
    2021222324252729313233384448505153576062    -646668707273     100100100100100100100100100100100100100100100100100100100100100100100100100100
    747880828486889296100102115116120124130132136144145    -146148149150151152     100100100100100100100100100100100100100100100100100100100100100100100100100100
    163164169170171172173174177178188189190194203206213236366368    -381383543     100100100100100100100100100100100100100100100100100100100100100100100
   比较化合物A比较化合物B     27100
比较化合物A：
Figure C9010826500781
比较化合物B：
Figure C9010826500782
试验2：对于绿色稻微叶蝉的效应
将发芽后7天龄的稻秧浸入由上述杀虫剂实例的实例7中所描述的可乳化的浓缩物，并且用水稀释至化合物浓度为125ppm(如所描述的)的化合物溶液中，持续30秒。在空气中干燥后，将经处理的秧苗置于试管中，将10条第3龄期的对有机磷和氨甲酸酯有抗性的绿色稻微叶蝉的幼虫接种进去。用纱布盖住试管，将其置于温度为25℃，湿度为65％的暖房里。5天后检查死亡率。
结果示于表3中。
              表3
化合物No.     死亡率％(5天后)125ppm
    1        -24681016     100  ％100100100100100100
    1820212223242527282931323335364448505153         -576062666872     100100100100100100100100100100100100100100100100100100100100100100100100100100
    737478828486889296100102116120124130132136144146148        -150152164169170171     100100100100100100100100100100100100100100100100100100100100100100100100100100
    172173174178188190201203213236366368369381     100100100100100100100100100100100100100100
  比较化合物A比较化合物B比较化合物C     000
比较化合物A和B：与试验1中相同化合物C：
Figure C9010826500811
                    (马拉硫磷)试验3：对于稻粘虫的效应
将试验化合物以与实例8相同的方法制成可湿性粉剂。用水将化合物稀释至125ppm。将玉米叶浸入化学溶液中30秒钟。空气干燥后，将经处理的叶子置于陪替氏培养皿中，将5条第三龄期的稻粘虫接种入内。用玻璃盖盖住陪替氏培养皿，将它们放入温度为25℃，相对湿度为65％的暖房中。5天后检查死亡率。每个试验重复二次。结果示于表4中。
                    表4
化合物No.     死亡率％(5天后)125ppm
    212223242551578892148172      -381     100％100100100100100100100100100100100
  比较化合物A比较化合物B比较化合物D     0040
比较化合物A和B：与试验1中相同化合物D：

Claims (6)

1.一种杀虫剂组合物，其特征在于它的活性成分为如下通式表示的化合物或它的盐：式中R1选自被甲基、氟、氯、溴取代的吡啶基；
X表示C1-3亚烃基；
R2选自氢；氨甲酰基；一或二C1-5烷基氨甲酰基；硫代氨甲酰基；一或二C1-5烷基硫代氨甲酰基；氨磺酰基；一或二C1-5烷基氨磺酰基；可被氟、甲氧基、甲硫基、乙氧基羰基、氰基、苯基、氯代苯基、甲氧基苯基、呋喃基、噻吩基、吡啶基、氯代吡啶基、噻唑基或氯代噻唑基取代的C1-5烷基；C2-5链烯基；C2-5炔基；C3-8环烯基；芳基；或-Y-R5；
其中Y表示O、S(O)n、CO、CS或CO2；
n表示0、1或2；
R5代表氢、C1-5烷基、C2-5链烯基、C2-5炔基、C3-8环烷基、C3-8环烯基或芳基；
R3代表氢；可被F、Cl、甲氧基、甲硫基、乙氧基羰基、氰基、苯基、氯代苯基、甲氨基、二甲氨基、氰亚氨基、氯代吡啶甲基氨基、或N-甲基-N-氯代吡啶甲基氨基取代的C1-5烷基；C2-5链烯基；C2-5炔基；C3-8环烯基；
R4表示氰基或硝基；
Z表不N。
2.如权利要求1所述的组合物，其特征在于R1为被氟、氯或溴取代的吡啶基。
3.如权利要求1所述的组合物，其特征在于它的活性成分为N-氰基-N′-(2-氯-5-吡啶甲基)-N′-甲基乙脒。
4.如权利要求1所述的组合物，其特征在于它的活性成分为N-氰基-N′-(2-氯-5-吡啶甲基)-N′-乙基乙脒。
5.如权利要求1所述的组合物，其特征在于它的活性成分为N-(2-氯-5-吡啶甲基)-N-甲基-N′-乙基乙脒。
6.如权利要求1-5中所述的组合物在控制鳞翅目和半翅目昆虫中的应用。
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