CN1089938A - 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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CN1089938A
CN1089938A CN93121610A CN93121610A CN1089938A CN 1089938 A CN1089938 A CN 1089938A CN 93121610 A CN93121610 A CN 93121610A CN 93121610 A CN93121610 A CN 93121610A CN 1089938 A CN1089938 A CN 1089938A
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CN1044600C (zh
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J·A·弗奇
D·C·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I式。
此式的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

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，繁残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 931216109_IMG17
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卤烷基、C1-C6烷氧基或C1-C6卤烷氧基、C1-C6烷氧基或C1-C6卤烷氧基;
n为0、1或2的整数;
Q为
Figure 931216109_IMG18
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 931216109_IMG19
;
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，
Figure 931216109_IMG20
R11为
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
Figure 931216109_IMG22
，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 931216109_IMG23
，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 931216109_IMG24
。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 931216109_IMG25
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 931216109_IMG26
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。
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。
Figure 931216109_IMG28
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 931216109_IMG29
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Ⅴ  N-芳基酰肼类的结构式如下
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Ⅴ N-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。
Figure 931216109_IMG31
施用结构式Ⅰ  N-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。本发明的组合物的应用，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，气侯条件等，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Ⅰ  N-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1
2，2-二甲基丙酸，2-（2，6-二氯-α，α，α-三氟-P-甲苯基）酰肼的制备
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 931216109_IMG33
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Ⅰ
Figure 931216109_IMG34
实施例号  A  B  W  Yn  R  mp℃
2 C-Cl CH C-CF36-Cl (CH3)2CHCH2135-136
3 C-Cl CH C-Cl 6-Cl (CH3)3C 124-125.5
4 C-Cl CH CH 6-Cl (CH3)3C 114-115
5 C-Br CH C-CF36-Br (CH3)3C 118-120
6 C-Br CH C-CF36-Br CH3173-175
7 C-Br CH C-CF36-Br C6H5181-184
Figure 931216109_IMG36
Figure 931216109_IMG38
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
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 931216109_IMG41
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。
Figure 931216109_IMG42
Figure 931216109_IMG43
Figure 931216109_IMG44
Figure 931216109_IMG45
Figure 931216109_IMG47
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 931216109_IMG48
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146  N-乙基-2，2-二甲基-丙酰胺，2-（2，6-二氯-α，α，α-三氟-P-甲苯腙盐酸盐的制备
于搅拌下，在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（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℃。
Figure 931216109_IMG51
Figure 931216109_IMG52
Figure 931216109_IMG53
Figure 931216109_IMG54
Figure 931216109_IMG56
Figure 931216109_IMG57
Figure 931216109_IMG58
Figure 931216109_IMG59
Figure 931216109_IMG60
Figure 931216109_IMG61
Figure 931216109_IMG62
Figure 931216109_IMG63
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（southern  armyworm）
将一片Sieva  Limabean叶展至7-8cm长，浸入待测液，搅拌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  56-65
1  10-25  6  66-75
2  26-35  7  76-85
3  36-45  8  86-99
4  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12-斑点螨2玉米根虫3
(实施例号)  (300ppm)  (300ppm)  (50kg/ha)
85  0  0  100
86  100  0  80
87  40  90  100
88  ---  ---  ---
89  0  0  100
90  0  0  20
91  0  80  100
92  0  0  100
93  0  0  100
94  ---  80  100
95  80  0  100
96  100  40  80
97  0  0  100
98  40  0  40
100  0  40  0
101  0  0  60
102  0  60  100
103  40  0  100
104  0  90  50
105  20  0  90
106  40  0  100
107  ---  ---  100
108  90  50  100
109  0  0  50
110  0  0  100
111  100  40  90
112  40  100  20
113  20  100  100
114  40  100  100
表IV(续)
死亡百分数
化合物 行军虫12-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12-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12-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12-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12-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 (12)

1、控制昆虫或螨虫的方法，其特征在于：使所述害虫或其食物，聚集或繁殖场所与有效杀虫剂量的下列结构化合物接触
Figure 931216109_IMG2
其中
A为C-R4或N；
B为C-R5或N；
W为C-R6或N并且A，B或W中至少有一个不是N；
Y为卤素，CN，NO2，C1-C6烷基，C1-C6卤烷基，C1-C6烷氧基或C1-C6卤烷氧基；
n为0，1或2的整数；
Q为
Figure 931216109_IMG3
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 931216109_IMG4
R4，R5和R6各为5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，
R11
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
Figure 931216109_IMG7
，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 931216109_IMG8
，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
与酸加成盐接触。
2、按照权利要求1的方法，其中Q为
Figure 931216109_IMG9
3、按照权利要求2的方法，其中A为C-R4，B为CH，W为C-R6，Y为卤素，n为1，R1为氢，R4和R6各为卤素或由一个或多个卤素任意取代的C1-C6烷基，R，R3和R16为氢或C1-C10烷基。
4、按照权利要求1的方法，其中Q为
Figure 931216109_IMG10
5、按照权利要求4的方法，其中R1和R2为氢，R为C1-C6烷基，A为C-R3，B为C-R4，W为C-R5，Y为卤素，n为1，R3为卤素，R4为氢及R5为由一个或多个卤素取代的C1-C6烷基。
6、按照权利要求5的方法，其中化合物为2，2-二甲基丙酸，2-（2，6-二氯-α，α，α-三氟-P-甲苯基）酰肼。
7、具有下列结构的化合物
Figure 931216109_IMG11
其中A，B，W，Y，n，R，R1，R3和R16如权利要求1中所述，同时必须符合当A，B和W都不是N时，R和R3或R16之一不是氢，还必须符合当A，B或W之一为N时，Y，R4，R5或R6必须不是C1-C10烷基。
8、按照权利要求7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，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。
9、按照权利要求8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-P-甲苯基）腙。
10、具有下列结构化合物的制备方法
Figure 931216109_IMG13
其中A，B，W，Y，n，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
与至少1摩尔当量的胺化合物，HNR3R16进行反应。
11、控制昆虫或螨虫的组合物，它含有一惰性液体或固体截体和有效杀虫剂量的结构式Ⅰ化合物
Figure 931216109_IMG15
其中A，B，W，Y，n，R1和Q已在权利要求1中说明。
12、按照权利要求11的组合物，其中式Ⅰ化合物具有下列结构
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，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。
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AU675253B2 (en) 1997-01-30
DE69331600D1 (de) 2002-03-28
CN1044600C (zh) 1999-08-11
BG98338A (bg) 1994-07-29
ZW17693A1 (en) 1994-04-20
PL176108B1 (pl) 1999-04-30
SK281733B6 (sk) 2001-07-10
SK148493A3 (en) 1994-12-07
YU81993A (sh) 1996-08-13
PL301659A1 (en) 1994-07-11
JP2005263809A (ja) 2005-09-29
CA2112420C (en) 2007-02-13
HUT67294A (en) 1995-03-28
AU5267993A (en) 1994-07-14
RU2140738C1 (ru) 1999-11-10
BG61986B1 (bg) 1998-12-30
KR940014359A (ko) 1994-07-18
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CZ280893A3 (en) 1994-07-13
KR100314220B1 (ko) 2002-02-19
JP3816543B2 (ja) 2006-08-30
IL108188A0 (en) 1994-04-12
RO113556B1 (ro) 1998-08-28
IL108188A (en) 2001-11-25
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UA35563C2 (uk) 2001-04-16
EP0604798B1 (en) 2002-02-20

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