CN1044600C - 用作杀虫剂和杀螨剂的n-芳基肼衍生物 - Google Patents

用作杀虫剂和杀螨剂的n-芳基肼衍生物 Download PDF

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CN1044600C
CN1044600C CN93121610A CN93121610A CN1044600C CN 1044600 C CN1044600 C CN 1044600C CN 93121610 A CN93121610 A CN 93121610A CN 93121610 A CN93121610 A CN 93121610A CN 1044600 C CN1044600 C CN 1044600C
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alkyl
alkoxyl group
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haloalkyl
halogenated alkoxy
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CN1089938A (zh
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J·A·弗奇
Ｄ·Ｇ·库里
D·A·享特
A·C·卢
C·E·格勒诺斯坦杰斯基
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BASF Agricultural Co.,Ltd. Almheim Netherlands Wedensville branch
Basf Open Co.,Ltd.
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American Cyanamid Co
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Abstract

结构式为
的N-芳基肼衍生物，其控制昆虫和螨虫的用途及保护庄稼不受上述虫害而造成破坏和损失的方法和组合物。

Description

用作杀虫剂和杀螨剂的N-芳基肼衍生物
某些昆虫和螨虫对农作物，贮存物品，人和动物健康有害，每年由此造成很大损失。本发明目的在于提供取代的N-芳基肼衍生物，此为控制传染性的昆虫和螨虫的有效药物。
本发明的另一目的为提供保护重要的农作物免受昆虫和螨虫侵害和破坏的方法。
本发明进一步目的为提供杀虫和杀螨的组合物。
本发明提供一种控制昆虫和螨虫的方法，此法将所述昆虫、螨虫或者它们的食物，繁殖场所或聚集处与有效杀虫剂量的结构式Ⅰ的N-芳基衍生物接触
Figure C9312161000071
其中
A是C-R4或N；
B是C-R5或N；
W是C-R6或N；同时，A,B或W中之一必须不是N；
Y为氢、卤素、CN、NO2、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基、C1-C6烷氧基或C1-C6卤代烷氧基；n为0、1或2的整数；Q为
Figure C9312161000081
R为氢，
由下列基团任意取代的C1-C10烷基：
    一个或多个卤素，C3-C6环烷基，C1-C4烷氧基，
    C1-C4卤烷氧基，(C1-C4烷基)SOx,(C1-C4卤烷
    基)SOx，由一至三个卤素、C1-C4烷基、C1-C4卤烷
    基、C1-C4烷氧基、C1-C4卤烷氧基、(C1-C4烷基)
    SOx、(C1-C4卤烷基)SOx、NO2或CN基任意取代
    的苯基，或由一至三个卤素、C1-C4烷基、C1-C4卤
    烷基、C1-C4烷氧基、C1-C4卤烷氧基、(C1-C4烷
    基)SOx、(C1-C4卤烷基)SOx、NO2或CN基任意取
    代的苯氧基，
由下列基团任意取代的C3-C12环烷基：
    一个或多个卤素，C1-C6烷基，C1-C6卤烷基，C1-
    C4烷氧基，C1-C4卤烷氧基，(C1-C4烷基)SOx，
    (C1-C4卤烷基)SOx，由一至三个卤素、C1-C4烷基、
    C1-C4卤烷基、C1-C4烷氧基、C1-C4卤烷氧基、NO2
    或CN基任意取代的苯基，或由一至三个卤素、C1-
    C4烷基、C1-C4卤烷基、C1-C4烷氧基、C1-C4卤烷
    氧基、NO2或CN基任意取代的苯氧基，或
由一个或多个卤素，C1-C4烷基，C1-C4卤烷基，C1-C4烷氧基，C1-C4卤烷氧基，NO2或CN基任意取代的苯基；R1和R2各为独立的氢或C1-C4烷基；R3和R16各为独立的氢，
由下列基团任意取代的C1-C10烷基：
    一个或多个卤素，羟基，C1-C4烷氧基，(C1-C4烷
    基)SOx,CONR7R8,CO2R9,R10,R11，由一至三个卤
    素、C1-C4烷基、C1-C4卤烷基、C1-C4烷氧基、C1-
    C4卤烷氧基、NO2或CN基任意取代的C3-C6环烷
    基，由一个或多个卤素、C1-C4烷基、C1-C4卤烷基、
    C1-C4烷氧基、C1-C4卤烷氧基、CO2或CN基任意
    取代的苯基，或由一个或多个卤素、C1-C4烷基、
    C1-C4卤烷基、C1-C4烷氧基、C1-C4卤烷氧基、
    NO2或CN基任意取代的吡啶基，
由下列基团任意取代的C3-C10链烯基：
    一个或多个卤素，羟基，C1-C4烷氧基，(C1-C4烷
    基)SOx,CONR7R8,CO2R9,R10,R11，由一至三个卤
    素、C1-C4烷基、C1-C4卤烷基、C1-C4烷氧基、C1-
    C4卤烷氧基、NO2或CN基任意取代的C3-C6环烷
    基，由一个或多个卤素，C1-C4烷基，C1-C4卤烷
    基，C1-C4烷氧基，C1-C4卤烷氧基，CO2或CN基
    任意取代的苯基，或由一个或多个卤素、C1-C4烷
    基、C1-C4卤烷基、C1-C4烷氧基、C1-C4卤烷氧基、
    NO2或CN基任意取代的吡啶基，
由下列基团任意取代的C3-C10炔基：
    一个或多个卤素，羟基，C1-C4烷氧基，(C1-C4烷
    基)SOx,CONR7R8,CO2R9,R10,R11，由一至三个卤
    素、C1-C4烷基、C1-C4卤烷基、C1-C4烷氧基、C1-
    C4卤烷氧基、NO2或CN基任意取代的C3-C6环烷
    基，由一个或多个卤素、C1-C4烷基、C1-C4卤烷基、
    C1-C4烷氧基、C1-C4卤烷氧基、CO2或CN基任意
    取代的苯基，或由一个或多个卤素、C1-C4烷基、
    C1-C4卤烷基、C1-C4烷氧基、C1-C4卤烷氧基、
    NO2或CN基任意取代的吡啶基，
由下列基团任意取代的C3-C12环烷基：
    一个或多个卤素，羟基，C1-C4烷氧基，(C1-C4烷
    基)SOx,CONR7R8,CO2R9,R10,R11，由一至三个卤
    素、C1-C4烷基、C1-C4卤烷基、C1-C4烷氧基、C1-
    C4卤烷氧基、NO2或CN基任意取代的C3-C6环烷
    基，由一个或多个卤素、C1-C4烷基、C1-C4卤烷基、
    C1-C4烷氧基、C1-C4卤烷氧基、CO2或CN基任意
    取代的苯基，或由一个或多个卤素、C1-C4烷基、
    C1-C4卤烷基、C1-C4烷氧基、C1-C4卤烷氧基、
    NO2或CN基任意取代的吡啶基或
R3和R16可连在一起形成具下列结构的环
Figure C9312161000101
R4,R5和R6各为独立的氢，卤素，CN,NO2,(C1-C4烷基)
SOx,(C1-C4卤烷基)SOx,C1-C6烷基、C1-C6卤烷基,C1-C6烷氧基或C1-C6卤烷氧基；R7,R8和R9各为独立的氢或C1-C4烷基；R10为NR12R13,或
Figure C9312161000103
R11为
Figure C9312161000111
R12,R13,R14和R15各为独立的氢或C1-C4烷基；
X为O,S或NR14；
X1为氯，溴或氟；
r为0或1的整数；
←p和m各为0,1,2或3的整数，同时p,m或r中只有一个
  可为0，而且p+m+r之和必须是4,5或6；
x为0,1或2的整数；或符合下列条件时
当Q为 ，R为C1-C5烷基，X1为氯时，则至少A,B或W之一必须是N或R4,R5,R6和Y必须不是氢，n必须为0，并且当Q为
Figure C9312161000113
，R为苯基或取代苯基，X1为氯时，则至少A,B或W之一必须为N与其酸加成盐接触。
本发明进一步提供结构式Ⅰ的N-芳氨基腙化合物，其中A,B,W,Y,n和R1如前所术，Q为
Figure C9312161000114
。当A,B和W都不是N时，则R和R3或R16之一必须不是氢，而且当A,B或W之一是N时，则Y,R4,R5或R6必须不是C1-C10烷基。
本发明亦提供保护生长中的植物免受昆虫和螨虫攻击和侵扰的组合物和方法。
各种昆虫和螨虫能损害和破坏农作物及其他有价值的植物，帮助使植物致病的细菌，真菌和病毒的传播和生长，破坏或降低贮存食物、其他产品和物品的价值，从而造成很大的经济损失。昆虫和螨虫给农民带来了世界性的极大问题。对昆虫和螨虫选择性的，有效的控制已成为全球的需要。
现在已经发现结构式Ⅰ的取代的N-芳基腙衍生物是特别有效的杀虫剂和杀螨剂，特别是对鞘翅目，鳞翅目和蜱螨目。
本发明的氨基腙化合物结构见结构式Ⅰa
Figure C9312161000121
其中A,B,W,Y,n,R,R1,R3和R16如前所述。在说明书和权利要求书中所用的卤素这一项指氯，氟，溴或碘。酸加成盐这一项指由现有技术中通常所知的酸如盐酸，氢溴酸，硫酸，半硫酸等形成的盐。在上述定义中，当n为0时，Y为氢。
本发明的较佳化合物是其中R,R3和R16各为独立的氢或C1-C6烷基，A为C-R4,B为C-R5,W为C-R6,Y为卤素及n是1的那些化合物。特佳化合物是R1为氢，R4为卤素，R5为氢和/或R6为由一或多个卤素，取代的C1-C6烷基，以三氟甲基为更好。
本发明的其他较佳化合物为具有下列结构的化合物
Figure C9312161000122
其中R是C1-C10烷基；
R1是氢或C1-C4烷基；
R3是C1-C10烷基；
R16是氢或C1-C10烷基；
R4,R6和Y各为氢，卤素，CN,NO2,C1-C6烷基，C1-C6卤烷基，C1-C6烷氧基，或C1-C6卤烷氧基。
结构式Ⅰa的N-芳基氨基腙可以通过一种酰氯，即结构式Ⅱ的腙(肼酰氯)与胺化合物HNR3R16反应制得，见流程Ⅰ。
                  流程Ⅰ
Figure C9312161000131
结构式Ⅱ的化合物可由一合适的结构式Ⅲ的芳基肼，与一适宜的酰氯RCOCl反应，生成结构式Ⅳ的N-芳基肼，将式Ⅳ肼与卤化剂如亚硫酰卤反应，得所需的产品结构式Ⅱ的N-芳基肼酰卤。反应由下列流程Ⅱ说明。
                 流程Ⅱ
本发明的取代的N-芳基肼衍生物对控制昆虫和螨虫是有效的。所述化合物也能有效地保护正在生长的以及收获的庄稼免受这些害虫的攻击和侵扰。
本发明方法中有用的化合物包括结构式Ⅱ的N-芳基肼酰卤。本发明的具有杀虫和杀螨作用的式Ⅱ肼酰卤(结构式Ⅱ)具有如下结构式
Figure C9312161000142
其中，A,B,W,Y,n,R,R1和X1如前所述。
较佳的式Ⅰ化合物是R1为氢，A为C-R4,B为C-R5,W为C-R6,Y为卤素或硝基，n为1的那些化合物。特佳的是R4为卤素，R5为氢，R6为由一或多个卤素取代的C1-C6烷基(以三氟甲基为佳)的化合物。
其他较佳的式Ⅱ化合物是R为由C3-C12环烷基或C1-C10卤烷基(以C1-C6卤烷基为佳)任意取代的那些化合物。
如March所述(见Advanced Organic Chemistry,4版。(1992)，第438页)，结构式Ⅱ中X1为氟的化合物可以由结构式Ⅱ(其中X1是氯或溴)的化合物用氟化钠或氟化氢通过卤素交换反应制得。
本发明方法中有用的其他化合物包括取代的羧酸，结构式Ⅴ的N-芳基酰肼化合物。
本发明具杀虫杀螨作用的式ⅤN-芳基酰肼类的结构式如下
Figure C9312161000151
本发明方法中所用的较佳的式Ⅴ化合物是R为氢或C1-C6烷基，A为C-R4,B为C-R5,W为C-R6,Y为卤素或硝基，n为1的那些化合物。特佳的式ⅤN-芳基酰肼是R4为卤素，R5为氢，R6为由一或多个卤素取代的C1-C6烷基(以三氟甲基为宜)的化合物。
式Ⅴ化合物可由合适的式Ⅵ芳基肼与适宜的酰氯RCOCl反应制得，得到所要求的式ⅤN-芳基酰肼。反应由流程Ⅲ说明。
               流程Ⅲ
Figure C9312161000161
施用结构式ⅠN-芳基肼衍生物的有效杀虫剂量于作物的叶子，其生长的土壤或水，可保护正在生长的或已收获的作物不受昆虫或螨虫的攻击和侵扰。
当结构式Ⅰ化合物施用于植物或其生长的土壤或水时，实际上一般用大约10ppm至10000ppm(以大约100至5000ppm为佳)分散在水质载体中的式Ⅰ化合物，即能有效地保护植物不受昆虫和螨虫的攻击和侵扰。结构式Ⅰ化合物应用于土壤对控制鞘翅目和双翅目昆虫胚胎后发育阶段特别有效。本发明组合物的应用，如喷雾，一般以提供约0.125kg/ha至约250kg/ha的用量为有效，约10kg/ha至100kg/ha更好。当然，可以预料，根据主要的环境情况如害虫密度，传播程度，植物生长阶段，土壤条件，气候条件等，可以采用较高或较低量的N-芳基肼衍生物。
有利的是式Ⅰ化合物可与其他生物和化学控制剂包括其他的杀虫剂，杀线虫剂，杀螨剂，灭螺剂，杀真菌剂和杀菌剂如核多角体病毒，吡咯类，芳基吡咯类，卤代苯甲酰脲类，拟除虫菊酯类，氨基甲酸酯类，磷酸酯类等联合使用。
适合于结构式ⅠN-芳基肼衍生物的典型制剂为颗粒组合物，可流动组合物，可湿润粉剂，细粉，微乳，可乳化浓缩物等。凡适用于土壤，水和叶子施用和能提供有效的保护植物作用的所有组合物都合适。本发明的组合物包括与惰性固体或液体载体混合的式ⅠN-芳基肼衍生物。
如本发明组合物要与其他生物或化学剂结合使用时，可以采用它们的混合物或也可以顺序使用。
为了对本发明更清楚地了解，下面列出了一些具体的实施例。这些实施例只是说明性的，无论如何不能理解为限制本发明的范围和构成本发明的原则。
实施例12,2-二甲基丙酸，2-(2,6-二氯-α,α,α-三氟-P-甲苯基)酰肼的制备
Figure C9312161000171
于2,6-二氯-4-(三氟甲基)苯肼(50.0g,0.20mol)的二氯甲烷溶液中滴加三甲基乙酰氯(30.6g,0.254mol)，搅拌30分钟，加10％NaOH水溶液并搅拌3小时。分离出有机相用水洗，于MgSO4中干燥，真空浓缩得灰白色固体残留物。用1,2-二氯乙烷将此固体重结晶即得本品，为白色固体，55g(82％得率)，熔点140-141°，用1HNMR,13CNMR和IR光谱分析鉴定。
实施例2-42取代的N-芳基酰肼衍生物的制备
Figure C9312161000181
基本上采用实施例1所述相同的方法，取代合适的芳基肼和酰氯即可制得表1所示的化合物，用1HNMR,13CNMR和IR光谱分析鉴定。
                       表1
Figure C9312161000182
实施例号    R    B     W     Yn          R               mp℃2        C-Cl   CH  C-CF3 6-Cl    (CH3)2CHCH2   135-1363        C-Cl   CH  C-Cl   6-Cl    (CH3)3C        124-125.54        C-Cl   CH  CH     6-Cl    (CH3)3C        114-1155        C-Br   CH  C-CF3 6-8r    (CH3)3C        118-1206        C-Br   CH  C-CF3 6-Br    CH3             173-1757        C-Br   CH  C-CF3 6-Br    C6H5           181-184
               表Ⅰ(续)实施例号     A      B      W       Yn         R                  mp℃8         C-CH3   CH    C-Cl     H       (CH3)3C          103-1069         C-Cl     CH    C-CF3   6-Cl    (CH3)3CCH2     125-12710        C-Cl     CH    C-Cl     6-Cl    pClC6H5          188-19011        C-Cl     CH    C-CF3   6-Cl    (CH3)2CH        158-15912        C-Cl     CH    C-Cl     6-Cl    cyclopropyl        186-18813        C-Cl     CH    C-CF3   6-Cl    CH3CH2C(CH3)2 121-12314        C-H      CH    C-CF3   H       (CH3)3C         136-13915        C-Cl     CH    C-CF3   H       (CH3)3C         143-145
                 表Ⅰ(续)
Figure C9312161000201
实施例号    A     B       W        Yn       R                     mp℃16        C-Cl    CH    C-CF3    6-Cl    
Figure C9312161000202
             125-12717        C-Cl    C-Cl  C-Cl     5,6-diCl (CH3)3C18        N       CH    C-CF3   6-Cl     (CH3)3C             151-151.519        C-Cl    CH    C-Cl     6-Cl     
Figure C9312161000203
   138-14020        C-Cl    CH    C-CF3   6-Cl     pClC6H5OC(CH3)2  137-13921        C-CF3  CH    CH       H        (CH3)3C             98-10022        C-Cl    CH    C-CF3   6-Cl                   101-10323        C-Cl    CH    C-Cl     6-Cl     cyclohexyl            188-189
                      表Ⅰ(续)实施例号   A      B       W       Yn           R               mp℃24        C-Cl    CH    C-CF3   6-Cl    C6H5C(CH3)2     104-10525        C-Cl    CH    C-Cl     6-Cl    CF3CF2             131-13226        C-Cl    CH    C-Cl     6-Cl    (CH3)2CH           164-16527        C-Cl    CH    C-CF3   6-Cl    cyclopropyl          172-17428        C-Cl    CH    C-Cl     6-Cl    CH3CH2C(CH3)2   132-13429        C-Cl    CH    C-CF3   6-Cl                  160-16230        C-Br    CH    C-CF3   6-Br    (CH3)3C            140-14131        C-Cl    CH    C-Cl     6-Cl    CH3(CH2)5C(CH3)2
                   表Ⅰ(续)
Figure C9312161000221
实施例号  A        B    W          Yn       R                        mp℃32        N        N    C-Cl       H     (CH3)3C                  178-18233        C-Cl    CH    C-CF3    6-Cl   
Figure C9312161000222
                   121-12334        C-Cl    CH    C-CF3    6-Cl   pClC6H5C(CH3)2        105-10735        C-Cl    CH    C-CF3    6-Cl   ClCH2C(CH3)2            119-12036        C-Cl    CH    C-CF3    6-Cl   
Figure C9312161000223
                 174-17537        C-Cl    CH    C-Cl      6-Cl   ClCH2C(CH3)2            124-12538        C-Cl    CH    CH        5-CF3 (CH3)3C                  170-177.539        C-Cl    CH    C-CF3    6-Cl   1-methylcyclohexyl          105-107
                     表Ⅰ(续)
Figure C9312161000231
实施例号   A    B         W     Yn       R              mp℃40        CH    C-CF3    CH    H        (CH3)3C    158-16041        C-F   C-F       C-F   5,6-diF  (CH3)3C    154-15742        C-Br  CH        F     6-Br     (CH3)3C    118-120
实施例43
1-氯-2,2-二甲基丙醛,2-(2,6-二氯-α,α,α-三氟-P-甲苯基)腙的制备
Figure C9312161000241
于回流温度下将2,2-二甲基-2-(2,6-二氯-α,α,α-三氟-P-甲苯基)酰肼丙酸(50.0g,0.125mol)和亚硫酰氯(53.8g,0.452mol)在甲苯中的混合物加热8小时，冷却至室温，真空浓缩得油状残留物。将此油状物溶于己烷后通过硅胶滤饼。用己烷分几次洗滤饼。滤液合并，真空浓缩得本品。为黄色油状物，47.2g(90％得率)，用1HNMR,13CNMR和IR光谱分析鉴定。
实施例44-84
取代的N-芳基肼酰氯的制备
Figure C9312161000242
基本上用实施例43所述相同的方法，替换合适的酰肼作用物，制得表Ⅱ所示的化合物，用1HMR,13CHMR和IR光谱分析鉴定。
                   表    Ⅱ
Figure C9312161000251
实施例号    A   B    W         Yn        R                  mp℃44        C-Cl  CH   C-CF3    6-Cl    (CH3)2CHCH245        C-Cl  CH   C-Cl      6-Cl    (CH3)3C          44.5-45.546        C-Cl  CH   CH        6-Cl    (CH3)3C47        C-Br  CH   C-F       6-Br    (CH3)3C48        C-Br  CH   C-CF3    6-Br    CH349        C-Br  CH   C-CF3    6-Br    C6H5
                表Ⅰ(续)实施例号    A    B     W     Yn    R               mp℃50        C-CH3 CH  C-Cl    H    (CH3)3C51        C-Cl   CH  C-CF3  6-Cl (CH3)3CCH252        C-Cl   CH  C-Cl    6-Cl pClC6H5       12053        C-Cl   CH  C-CF3  6-Cl (CH3)2CH54        C-Cl   CH  C-Cl    6-Cl cyclopropyl55        C-Cl   CH  C-CF3  6-Cl CH3CH2C(CH3)256        C-H    CH  C-CF3  H    (CH3)3C
                   表Ⅰ(续)
Figure C9312161000271
实施例号   A      B      W      Yn        R                     mp℃57        C-Cl    CH    C-CF3  H        (CH3)3C58        C-Cl    CH    C-CF3  6-Cl    
Figure C9312161000272
59        C-Cl    C-Cl  C-Cl    5,6-diCl (CH3)3C60        N       CH    C-CF3  6-Cl     (CH3)3C61        C-Cl    CH    C-Cl    6-Cl      62        C-Cl    CH    C-CF3  6-Cl     pClC6H5OC(CH3)263        C-CF3  CH    CH      H        (CH3)3C
                   表Ⅰ(续)
Figure C9312161000281
实施例号    A      R     W       Yn           R             mp℃64        C-Cl    CH    C-CF3   6-Cl    
Figure C9312161000282
65        C-Cl    C-CH  C-Cl     6-Cl    cyclohexyl66        C-Cl    C-CH  C-CF3   6-Cl    C6H5C(CH3)267        C-Cl    CH    C-Cl     6-Cl    CF3CF268        C-Cl    CH    C-Cl     6-Cl    (CH3)2CH69        C-Cl    CH    C-CF3   6-Cl    cyclopropyl70        C-Cl    CH    C-Cl     6-Cl    CH3CH2C(CH3)2
                    表Ⅰ(续)
Figure C9312161000291
实施例号    A      B      W        Yn       R                   mp℃71        C-Cl    CH    C-CF3    6-Cl    
Figure C9312161000292
             110-11172        C-Br    CH    C-CF3    6-Br    (CH3)3C73        C-Cl    CH    C-Cl      6-Cl    CH3(CH2)5C(CH3)274        N       N     C-Cl      H       (CH3)3C75        C-Cl    CH    C-CF3    6-Cl     76        C-Cl    CH    C-CF3    6-Cl    pClC6H5C(CH3)2  85-8877        C-Cl    CH    C-CF3    6-Cl    ClCH2C(CH3)2
                      表Ⅰ(续)
Figure C9312161000301
实施例号    A     B     W       Yn      R                     mp℃78        C-Cl    CH    CCF3   6-Cl  
Figure C9312161000302
               71-7379        C-Cl    CH    C-Cl    6-Cl  ClCH2C(CH3)280        C-Cl    CH    CH      5-CF3 (CH3)3C81        C-Cl    CH    C-CF3  6-Cl  1-methylcyclohexyl82        CH      C-CF3CH      H     (CH3)3C83        CH      CH    CH      5-F   (CH3)3C84        C-Br    CH    F       6-Br  (CH3)3C
实施例85
N-乙基-2,2-二甲基丙酰胺,2-(2,6-二氯-α,α,α-三氟-P-甲苯腙的制备
Figure C9312161000311
在室温条件下，于(2,6-二氯-α,α,α-三氟-P-甲苯基)腙1-氯-2,2-二甲基丙醛(20.0g,0.0575mol)的四呋喃溶液中滴加70％乙胺水溶液(28.0g,0.144mol)，搅拌1小时，真空浓缩得半固体残留物。将此半固体分散于乙醚和水。相分离后，用水洗有机相，于MgSO4中干燥，再真空浓缩得本品，为黄色油状物，19.8g(97％得率)，用1HNMR,13CNMR和IR光谱分析鉴定。
实施例86-169
取代的N-芳基氨基腙的制备
基本上用实施例85所述相同方法，替换合适的肼酰氯和合适的胺，制得表Ⅲ所列的化合物，用1HNMR,13CNMR和IR光谱分析鉴定。
本发明的盐酸盐可按照下面简述的步骤制得。
实施例146N-乙基-2,2-甲基丙酰胺[2-(2,6-氯-α,α,α-三氟)-对甲基]苯腙盐酸盐的制备
Figure C9312161000321
于搅拌下，在N-乙基-2,2-甲基丙酰胺，2-(2,6-氯-α,α,α-三氟)-对甲基苯腙(0.1g,2.8mmol)和己烷的混合物中通入HCl气体30分钟。将获得的反应混合物过滤即得本品，为白色固体，1.13g，熔点202-202.5℃。
                     表Ⅱ
Figure C9312161000331
实施例号
    A    B    W        Yn        R            R3            R16      mp℃86    C-Cl  CH   C-CF3   6-Cl    (CH3)3C     pClC6H5       H87    C-Cl  CH   C-Cl     6-Cl    (CH3)3C     CH3CH2CH2    H88    C-Cl  CH   C-Cl     6-Cl    (CH3)2CH    CH3CH2CH2    H      48-5089    C-Cl  CH   C-CF3   6-Cl    (CH3)3CCH2 CH3CH2CH2    H90    C-Cl  CH   C-Cl     6-Cl    (CH3)2CH    cyclopropyl      H91    C-Cl  CH   C-CF3   6-Cl    (CH3)3CCH2 CH3CH2        H
                      表Ⅱ(续)
Figure C9312161000341
实施例号    A      B      W        Yn         R           R           R16      mp℃92        C-Cl    CH    C-CF3    6-Cl    (CH3)2CH   CH3CH2      H      62-6493        C-Cl    CH    C-CF3    6-Cl    (CH3)3C    CF3CH2      H94        C-Br    CH    C-CF3    6-Br    (CH3)3C    CH3CH2      H95        C-Br    CH    C-CF3    6-Br    (CH3)3C    CH3CH2CH2  H96        C-Br    CH    C-CF3    6-Br    (CH3)3C    C6H5CH2    H97        C-Br    CH    C-CF3    6-Br    (CH3)3C    furfuryl       H
                     表Ⅱ(续)
Figure C9312161000351
实施例号    A      B      W       Yn       R             R3         R16         mp℃98        C-Br    CH    C-CF3   6-Br    CH3         CH3CH2     H99        C-Br    CH    C-CF3   6-Br    C6H5       CH3CH2     H100        C-C1    CH    C-Cl     6-Cl    (CH3)3C     H            H        131-135101        C-Cl    CH    C-Cl     6-Cl    (CH3)3C    CH3         CH3      61-63102        C-Cl    CH    C-Cl     6-Cl    (CH3)3C    CH3CH2     H103        C-Cl    CH    C-CF3   H       (CH3)3C    CH3CH2CH2 H104        C-Cl    CH    CH       6-Cl    (CH3)3C    CH3CH2CH2 H105        C-C1    CH    C-CF3   6-Cl    (CH3)3C     H            H        100-102.5
                     表Ⅱ(续)实施例号    A      B       W        Yn        R          R3              R16  mp℃106        C-Cl    CH    C-CF3    6-Cl    (CH3)3C    CH3             H    78-79.5107        C-Cl    CH    C-CF3    6-Cl    (CH3)3C    CH3             CH3108        C-Cl    CH    C-CF3    6-Cl    (CH3)3C    CH3CH2CH2     H109        C-Cl    CH    C-CF3    6-Cl    (CH3)3C    (CH3)3C        H    67.5-68.5110        C-Cl    CH    C-CF3    6-Cl    (CH3)3C    (CH3)2CHCH2   H111        C-Cl    CH    C-CF3    6-Cl    (CH3)3C    -CH2CH2CH2CH2-112        C-Cl    CH    C-Cl      6-Cl    环丙基        CH3              H   65-67
                   表Ⅱ(续)
Figure C9312161000371
实施例号    A       B      W       Yn      R                      R3                R16    mp℃113        C-Cl    CH    C-CF3    6-Cl    CH3CH2C(CH3)2    CH3CH2           H114        C-Br    CH    C-CF3    6-Br    (CH3)3C            (CH3)2CH          H115        C-Cl    CH    C-CF3    H       (CH3)3C            -CH2CH2CH2CH2-116        C-Cl    CH    C-CF3    6-Cl    CH3CH2C(CH3)2    CH3CH2           CH3CH2117        C-Cl    CH    C-CF3    H       (CH3)3C            CH3CH2            H118        C-Cl    CH    C-Cl      6-Cl    CH3CH2C(CH3)2    CH3CH2            H
                     表Ⅱ(续)
Figure C9312161000381
实施例号    A      B      W         Yn        R                 R3                      R16    mp℃119        C-Cl    CH    C-CF3    6-Cl    C6H5C(CH3)2   CH3CH2                 H120        C-Cl    CH    C-CF3    H       (CH3)3C         -CH2CH2CH2CH2CH2-121        CH      CH    C-CF3    H       (CH3)3C         CH3CH2                 H122        CH      CH    C-CF3    6-Cl    (CH3)2CHCH2    CH3CH2                 H     86.5-88.5123        C-Cl    CH    C-CF3    6-Cl    (CH3)3C         -CH2CH2CH2CH2CH2-124        C-Cl    CH    C-CF3    6-Cl    (CH3)3C         cyclohexyl                H125        C-Cl    CH    C-CF3    6-Cl    (CH3)3C         C6H5CH2CH2           H
                  表Ⅱ(续)实施例号  A       B    W         Yn         R                       R3              R16    mp℃126      C-Br    CH    C-F       6-Br      (CH3)3C               CH3CH2          H127      C-Cl    C-Cl  C-Cl      5,6-diCl  (CH3)3C               CH3CH2          H      63-65128      C-Cl    CH    C-Cl      6-Cl      CH3(CH2)5C(CH3)2  CH3CH2          H129      C-Cl    CH    C-CF3    6-Cl      
Figure C9312161000392
                 CH3CH2         H130      C-Cl    CH    C-CF3    6-Cl      (CH3)3C              CH3(CH2)2CH2  H131      C-Cl    CH    C-CF3    6-Cl      (CH3)3C              (CH3)2CH         H132      C-Cl    CH    C-CF3    6-Cl      (CH3)3C                     H
                    表Ⅱ(续)
Figure C9312161000401
实施例号    A      B       W       Yn       R                 R3         R16   mp℃133        C-Cl    CH    C-Cl     6-Cl   pClC6H5       (CH3)2CH      H    124-127134        C-Cl    CH    C-Cl     6-Cl   pClC6H5       CH3CH2        H    127-132135        C-Cl    CH    C-CF3   6-Cl   C6H5C(CH3)2 C6H5CH2CH2H136        C-Cl    CH    C-CF3   6-Cl   
Figure C9312161000402
          CH3CH2       H    74-75137        C-CF3  CH    CH        H    (CH3)3C        CH3CH2        H138        C-Cl    CH    C-CF3    H    (CH3)3C        C6H5CH2CH2 H139        C-Cl    CH    C-CF3    H    (CH3)3C            H
                  表Ⅱ(续)
Figure C9312161000411
实施例号    A      B       W       Yn        R                    R3                 R16    mp℃140        CH      CH    C-CF3    H       (CH3)3C             
Figure C9312161000412
        H141        C-Cl    CH    C-CF3    6-Cl    pClC6H5C(CH3)2    CH3CH2            H142        C-Cl    CH    C-CF3    6-Cl    (CH3)3C             C6H5CH(CH3)      H143        C-Cl    CH    C-CF3    6-Cl    (CH3)3C             (CH3)2NCH2CH2   H144        C-Cl    CH    C-CF3    6-Cl    (CH3)3C             CH3CH2C(CH3)2   H145        C-Cl    CH    C-CF3    6-Cl    (CH3)3C                      H      100.5-101.5
                     表Ⅱ(续)
Figure C9312161000421
实施例号    A       B      W        Yn         R                  R3          R16     mp℃146*      C-Cl    CH    C-CF3    6-Cl    (CH3)3C          CH3CH2        H      202-202.5147        C-Br    CH    C-CF3    6-Br    (CH3)3C          
Figure C9312161000422
    H148        C-Cl    CH    C-CF3    6-Cl    
Figure C9312161000423
             CH3CH2      H149        C-Cl    CH    C-CF3    6-Cl    
Figure C9312161000424
             CH3CH2      H150        C-Cl    CH    C-CF3    6-Cl    CH3CH2C(CH3)2  C6H5CH2CH2 H151        C-Cl    CH    C-CF3    6-Cl    (CH3)3C           C6H5CH2     H
          *盐酸盐
                        表Ⅱ(续)
Figure C9312161000431
实施例号    A      B      W         Yn        R                 R3              R16          mp℃152        C-Cl    CH    C-CF3    6-Cl    (CH3)3C        CH3CH2        CH3CH2153        C-Cl    CH    C-CF3    6-Cl    
Figure C9312161000432
       CH3CH2           H154        C-Cl    CH    C-CF3    6-Cl    
Figure C9312161000433
      (CH3)2CH          H155        C-Cl    CH    C-CF3    6-Cl    ClCH2C(CH3)2  pCF3OC6H5       H        203-205156        C-Cl    CH    C-CF3    6-Cl    (CH3)3C        neopentyl           H157        C-Cl    CH    C-CF3    6-Cl    (CH3)3C        H2NCOCCH(CH3)2  H        160-162158        C-Cl    CH    C-CF3    6-Cl    (CH3)3C        
Figure C9312161000434
       H159        C-Cl    CH    C-CF3    6-Cl    (CH3)3C        pClC6H5-CH2CH2 H
                   表Ⅱ(续)实施例号 A     B    W      Yn       R                    R3                         R16     mp℃
Figure C9312161000442
162    C-Cl   CH   C-CF3 6-Cl    (CH3)3C          CH3(CH2)4CH(CH3)          H163    C-Cl   CH   C-CF3 6-Cl    (CH3)3C          (C2H5)2N(CH2)3CH(CH3)  H164    C-Cl   CH   C-CF3 6-Cl    (CH3)3C          CH2=CHCH2                   H165    C-Cl   CH   C-CF3 6-Cl    1-methylcyclohexyl  CH3CH2                      H166    C-Cl   CH   CH     5-CF3  (CH3)3C          CH3CH2                      H
表Ⅱ(续)
Figure C9312161000451
实施例号 A      B     W           Yn        R           R3        R16    mp ℃167     C-F    C-F   C-F       5,6-diF  (CH3)3C    CH3CH2    H168     C-Br   CH    C-F       6-Br     (CH3)3C    CH3CH2    H169     C-Cl   CH    C-CF3   6-Cl     (CH3)3C     H
实施例170
N-芳基肼衍生物杀虫和杀螨作用的评价
将待测化合物溶于含35％丙酮的水混合液中制得浓度为10,000ppm的待测液。然后根据需要用水配成稀释液。
Spodoptera eridania，第3龄幼虫，南方行军虫(southernarmyworm)
将一片Sieva Limabean叶展至7-8cm长，浸入待测液，搅动3秒钟，于通风柜中干燥。然后将叶子放在底上有湿滤纸、内有10个第3龄幼虫的100×10mm的培养皿中。3和5天时，观察死亡率，摄食减少情况，或对正常蜕皮的任何干扰。
棉叶螨(OP-耐药菌株)，2-斑点叶螨
挑选展成7-8cm，具有初生叶的Sieva Limabean植物，修剪成每盒一株植物。将从主要群体取得的受侵叶子切成小片，放在待测植物的每一叶片上，放置2小时使螨虫移动到待测植物上产卵。切成的受侵扰叶片的大小可以改变以使每一叶片约有100个螨虫。测定时，除去用来转移螨虫的叶片。将新受螨虫侵扰的植物浸在待测液中搅拌3秒钟后放在通风柜中干燥。2天后，取一叶片进行死亡率计数。5天后，另取一叶片观察卵和/或新出现的若虫的的死亡率。
Diabrotic undecimpunctata howardi，第3龄南玉米根虫
将ICC滑石细粉放入30ml的广口螺旋盖玻璃瓶中。吸取1ml适宜的丙酮待测液于滑石粉上使每一并具有1.25mg有效成份。将玻璃并置于和缓的空气流中直到丙酮挥发掉。掏松干的滑石粉，加入1CC小米种子作昆虫的食物，再在每一瓶中加入25ml湿土。盖好瓶子，在rortex混合器上充分混匀，然后于每瓶中加入10个第3龄根虫，松松地盖上瓶盖，使能交换空气保证幼虫能生长。6天时测定死亡数。消失的幼虫作为死亡计，因为它们迅速分解。本测定所用的浓度约相当于50kg/ha。
按下表所列等级对测定进行等级评定，在表Ⅳ,Ⅴ和Ⅵ中列出所得结果。
            评价等级等级    死亡百分率    等级    死亡百分率0        无作用        5        56-651        10-25         6        66-752        26-35         7        76-853        36-45         8        86-994        46-55         9        100
表Ⅳ N-芳基氨基腙杀虫、杀螨作用评价
            死亡百分数化合物    行军虫1   2-斑点螨2  玉米根虫3(实施例号)(300ppm)   (300ppm)   (50kg/ha)85         0        0          10086        100       0          8087        40        90         10088        ---      ---         ---89        0         0          10090        0         0          2091        0         80         10092        0         0          10093        0         0          10094       ---        80         10095        80        0          10096        100       40         8097        0         0          10098        40        0          40100       0         40         0101       0         0          60102       0         60         100103       40        0          100104       0         90         50105       20        0          90106       40        0          100107      ---       ---         100108       90        50         100109       0         0          50110       0         0          100111       100       40         90112       40        100        20113       20        100        100114       40        100        100
            表Ⅳ(续)
            死亡百分数化合物    行军虫1   2-斑点螨2   玉米根虫3(实施例号) (300ppm)  (300ppm)    (50kg/ha)
115       0         0           100
116       20        50          100
117       20        0           100
118       50        70          100
119       100       50          90
120       ---       30          20
121       80        40          100
122       0         0           40
123       0         0           60
124       50        80          100
125       0         30          100
126       0         80          90
128       0         0           30
129       100       40          0
130       80        80          100
131       70        0           100
132       ---       40          100
133       ---       0           0
134       0         30          0
135       0         0           0
136       0         70          100
137       0         0           100
138       0         0           100
139       0         70          100
140       0         0           50
141       100       0           0
142       0         0           100
143       0         0           100
144       0         0           100
145       0         0           100
146       0         0           100
               表Ⅳ(续)
              死亡百分数化合物    行军虫1  2-斑点螨2 玉米根虫3(实施例号) (300ppm)   (300ppm)  (50kg/ha)
147        0         0        100
148        50        0        100
149        100       80       80
150        0         60       100
152        80        0        100
153        100       0        100
156        ---       0        100
157        0         0        100
158        40        0        100
159        0         0        100
160        0         0        100
161        0         0        ---
162        0         100      100
163        0         0        100
164        0         0        100
167        0         0        100
168        0         80       90
169        0         0        100
1行军虫为第3龄幼虫，南方行军虫
22-斑点螨2-斑点叶螨(OP-耐药)
3玉米根虫为第3龄南玉米根虫
表Ⅴ N-芳基氨基腙杀虫、杀螨作用评价
                   死亡百分数
化合物    行军虫1   2-斑点螨2   玉米根虫3(实施例号)    (300ppm)   (300ppm)    (50kg/ha)
1             8          0            9
2             0          0            7
3            ---        ---           9
4             0          0            7
5             0          0            8
6             0          0            0
7             0          0            0
8             5          0            8
9             0          0            0
10            1          9            3
11            1          0            9
12            4          0            4
13            0          9            3
14            7          0            7
15            9          0            3
16            0          0            0
17            1          3            0
18            2          0            6
19            9          0            0
20            0          0            0
21            0          0            7
22            0          0            0
23            0          0            0
24            0          0            0
25            9          0            8
26            0          0            0
27            4          0            6
28            2          0            0
29            3          0            0
表Ⅴ(续)
                死亡百分数化合物    行军虫1   2-斑点螨2   玉米根虫3(实施例号)(300ppm)   (300ppm)     (50kg/ha)
30        0        2            4
31        0        0            0
32        1        0            0
33        0        0            0
34        8        0            2
35        5        0            0
36        8        0            0
37        4        0            0
39        0        0            0
40        9        0            9
41        3        0            9
42        0        2            4
1行军虫为第3龄幼虫，南方行军虫
22-斑点螨2-斑点叶螨(OP-耐药)
3玉米根虫为第3龄南玉米根虫
表Ⅵ取代的N-芳基肼酰卤杀虫、杀螨作用评价
                死亡百分数化合物      行军虫1   2-斑点螨2   玉米根虫3(实施例号)  (300ppm)  (300ppm)    (50kg/ha)
78        90         90            0
54        80         100           0
58        0          0             0
59        0          100           0
64        ---        90            100
66        80         100           20
71        90         90            30
73        50         100           0
77        100        90            80
79        100        100           100
1行军虫为第3龄幼虫，南方行军虫
2斑点螨2-斑点叶螨(OP-耐药)
3玉米根虫为第3龄南玉米根虫

Claims (4)

1．具有下列结构的化合物其中A为C-R4或N；B为C-R5或N；W为C-R6或N；Y为卤素，CN,NO2,C1-C6烷基，C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基；n为0,1或2的整数；R为氢，
由下列基团任意取代的C1-C6烷基：
一个或多个卤素，C3-C6环烷基，C1-C6烷氧基，C1-C4卤代烷氧基，(C1-C4烷基)SOx，(C1-C4卤代烷基)SOx，由一至三个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、(C1-C4烷基)SOx、(C1-C4卤代烷基)SOx、NO2或CN基任意取代的苯基，或由一至三个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、(C1-C4烷基)SOx、(C1-C4卤代烷基)SOx、NO2或CN基任意取代的苯氧基，
由下列基团任意取代的C3-C12环烷基：
一个或多个卤素，C1-C6烷基，C1-C6卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，(C1-C4烷基)SOx，(C1-C4卤代烷基)SOx，由-至三个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、NO2或CN基任意取代的苯基，或由一至三个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、NO2或CN基任意取代的苯氧基，或
由一个或多个卤素，C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，NO2或CN基任意取代的苯基；R1为氢或C1-C4烷基；R3和R16各自独立地为氢，
由下列基团任意取代的C1-C10烷基；
一个或多个卤素，羟基，C1-C4烷氧基，(C1-C4烷基)SOx,CONR7R8,CO2R9,R10,R11，由一至三个卤素，C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、NO2或CN基任意取代的C3-C6环烷基，由一个或多个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、CO2或CN基任意取代的苯基，或由一个或多个卤素，C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、NO2或CN基任意取代的吡啶基，
由下列基团任意取代的C3-C10链烯基：
一个或多个卤素，羟基，C1-C4烷氧基，(C1-C4烷基)SOx,CONR7R8,CO2R9,R10,R11，由一至三个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、NO2或CN基任意取代的C3-C6环烷基，由一个或多个卤素，C1-C4烷基，C1-C4卤代烷基，C1-C4烷氧基，C1-C4卤代烷氧基，CO2或CN基任意取代的苯基，或由一个或多个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、NO2或CN基任意取代的吡啶基，
由下列基团任意取代的C3-C10炔基：
一个或多个卤素，羟基，C1-C4烷氧基，(C1-C4烷基)SOx,CONR7R8,CO2R9,R10,R11，由一至三个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、NO2或CN基任意取代的C3-C6环烷基，由一个或多个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、CO2或CN基任意取代的苯基，或由一个或多个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、NO2或CN基任意取代的吡啶基，由下列基团任意取代的C3-C12环烷基：
一个或多个卤素，羟基，C1-C4烷氧基，(C1-C4烷基)SOx,CONR7R8,CO2R9,R10,R11，由一至三个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、NO2或CN基任意取代的C3-C6环烷基，由一个或多个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、CO2或CN基任意取代的苯基，或由一个或多个卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、NO2或CN基任意取代的吡啶基或R3和R16可连在一起形成具有下列结构的环
Figure C9312161000041
R4和R5和R6各自独立地为氢，卤素，CN,NO2,(C1-C4烷基)SOx,(C1-C4卤代烷基)SOx,C1-C6烷基、C1-C6卤代烷基，C1-C6烷氧基或C1-C6卤代烷氧基；
R7,R8和R9各自独立地为氢或C1-C4烷基；R10为NR12R13,或
Figure C9312161000052
R11为
R12,R13,R14和R15各自独立地为氢或C1-C4烷基；
X为O,S或NR14；
X1为氯，溴或氟；
r为0或1的整数；
p和m各为0,1,2或3的整数，同时p,m或r中只有一个可为0，而且p+m+r之和必须是4,5或6；x为0,1或2的整数；
但有如下条件：
(a)A、B和W中至少一个必须不是N；
(b)当A、B和W中一个为N时，Y、R4、R5和R6中至少一个必须不是C1-C10烷基；以及
(c)当A、B和W都不是N时，R不能是苯基或取代苯基，或R3和R16中至少一个必须不是氢，或R4、R6不能是NO2。
2．按权利要求1所述的具有下列结构的化合物其中R为C1-C10烷基；
R1为氢或C1-C4烷基；
R3为C1-C10烷基；
R16为氢或C1-C10烷基；
R4为卤素、C、C1-C6烷基、C1-C4卤代烷基、C1-C6烷氧基或C1-C10卤代烷氧基；
R6和Y各为氢，卤素，CN,C1-C6烷基，C1-C6卤代烷基，C1-C6烷氧基或C1-C6卤代烷氧基。
3．按权利要求2所述的化合物，N-乙基-2,2-二甲基丙酰胺[2-(2,6-二氯-α,α,α-三氟)-对甲基]苯腙。
4．具有下列结构化合物的制备方法
Figure C9312161000061
其中A,B,W,Y,R,R1,R3和R16已在权利要求1中说明，其特征在于：将具有下列结构的化合物
Figure C9312161000062
与至少1摩尔当量的胺化合物HNR3R16进行反应。
CN93121610A 1992-12-29 1993-12-28 用作杀虫剂和杀螨剂的n-芳基肼衍生物 Expired - Fee Related CN1044600C (zh)

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