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CN1033699C - 杀虫的苯基肼衍生物 - Google Patents

杀虫的苯基肼衍生物 Download PDF

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CN1033699C
CN1033699C CN92114622A CN92114622A CN1033699C CN 1033699 C CN1033699 C CN 1033699C CN 92114622 A CN92114622 A CN 92114622A CN 92114622 A CN92114622 A CN 92114622A CN 1033699 C CN1033699 C CN 1033699C
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M·A·德凯瑟
P·T·麦克唐纳
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Abstract

具有下述结构式的化合物
其中X，Y，R和Z如公开的具体定义。本发明的化合物可有效地防治螨，线虫，稻飞虱，烟芽叶蛾，和十一星瓜叶甲。还公开了上述化合物的制备方法。

Description

杀虫的苯基肼衍生物
本申请是申请号07/796,506，1991.11.22申请，的后续申请。
本发明涉及具有杀虫剂，杀螨剂和杀线虫剂活性的新的苯基肼衍生物。本发明还涉及含上述化合物的杀虫，杀螨和杀线虫组合物，以及使用上述化合物或组合物防治昆虫，螨和线虫的方法。
昆虫，螨和线虫造成的破坏是农业中存在的严重问题，多种田间作物，其中包括那些有价值的如大豆，玉米，花生，棉花，紫花苜蓿，水稻和烟草作物，需要防止线虫，螨，和昆虫的损害。加之，如番茄，土豆，糖甜菜，胡萝卜，蜿豆，和类似的蔬菜以及水果，坚果，观赏植物和苗床作物如苹果，梨，杏，柑桔果实和葡萄也需要防止上述有害生物的侵害。
当然的，开发新的，更有效的包括杀虫剂，杀螨剂和杀线虫剂的农药是目前正在进行的一项科技活动。更具体的，开发有效的既能杀卵又能杀幼虫的农药是有价值的。
化学文摘108(19)，163280d涉及了所述的可用作杀螨剂的苯基肼羧酸烷基酯，美国专利4,725,302涉及了所述的可用作农药的取代的苯基肼和苯基噁二唑啉酮。欧洲专利0067471涉及了所述的可用作农药或化合物中间体的7-取代2，3-二氢苯并呋喃，德文特文摘88-312695/44涉及所述具有杀真菌，杀细菌，杀螨和消毒活性的三氟乙酸的芳基肼，化学文摘105(17)；152686c涉及所述的具有对抗昆虫和螨活性的多种苯基肼。
本申请涉及具有结构式(I)或(II)的化合物：
其中：
X是a)苯基；低级苯基烷氧基；苯氧基；或苯甲基；或b)一个a)组中的取代基和一或多个选自C1-C4烷氧基；卤素；低级烷基级；和低级硫烷基的取代基；或c)与其连接的苯基一起，形成多个稠合杂环，如二苯并呋喃基；
Y是H，C1-C4链烷酰基，C1-C4卤代烷酰基，二烷氧磷酰基，烷基氨基羰基，卤代烷基磺酰基，或C1-C4烷氧羰基；和
R是H，C1-C6烷基，C1-C6烷氧基，C3-C6环烷氧基，卤代烷基，烷氧烷基，芳基烷氧基，链烯基，硫烷基，烷氧羰基，烷基氨基，杂芳基，芳基烷基，卤代烷氧基，芳氧基，或C3-C6环烷基；和
Z是O或S。
进一步的，当X包括一个带苯基环(即，是苯基，苯基烷氧基，苯氧基或苯甲基)的取代基时，苯基环可任意地被一个或多个卤素，硝基，低级烷基，低级烷氧基，低级卤代烷基，或二烷基氨基取代。
本发明进一步涉及含有下述成分的农药组合物：a)作为活性成分的，有效量的具有上述式(I)或(II)结构的化合物；和(b)适于农用的载体。
本发明还涉及防治有害生物如昆虫，螨或线虫的方法，它包括把有效量的式(I)或(II)化合物或有效量的本发明的组合物施用于生长地以防止或除去有害生物。
本发明化合物具有如上述定义的结构式(I)或(II)，优选的化合物是那些其中Y是氢或COCF3的化合物。
结构式(I)的化合物的制备可通过在含有等量HCl吸收剂如吡啶的溶剂如甲苯中，使取代的苯基肼：与酰化试剂：其中Z是卤素或反应。反应的产物可进一步酰化，或用氧化剂如钯/空气通过氧化作用转化成具有结构式(II)的化合物。
本发明组合物含有(a)具有上述式(I)或(II)结构的化合物，和(b)适合的载体。上述适合的载体可以是天然的固体或液体载体。
适合的液体载体包括水，醇，酮，酚，甲苯和二甲苯。在上述制剂中，可以使用现有技术中采用的常规的添加剂，例如，一或多种表面活性剂和/或惰性稀释剂，以使施用所得组合物时容易处理。
本农药组合物可选择性的含有固体载体，以粉剂，颗粒剂，可湿性粉剂，糊剂，气雾剂，乳剂，乳油，和水溶性固体的形式存在。
例如，本发明的农药化合物当与固体载体粉末混合或吸收入固体载体粉末时可以粉剂的形式使用，固体载体粉末如矿物的硅酸盐，如云母，滑石，叶蜡石和粘土，当与表面活性分散剂一起时则获得可湿性粉剂，可湿性粉剂可直接施用于将被处理的生长地。可选择的，含有化合物的固体载体粉末的混合物，可被分散到水中形成以上述形式施用的悬浮液。
适合通过撒施，侧施，土壤混合或种子处理的方式施用的化合物的颗粒剂，适于采用颗粒或成片形式的载体制备。这些载体如颗粒粘土，硅石，木炭或玉米穗轴。
可选择的，当农药化合物用于液体载体则可以以液体或喷雾的形式使用，可以分散于含有相容的溶剂，如丙酮，苯，甲苯或煤油的溶液中或分散在适当的非溶剂介质中，例如水中。
另一种处理生长地的施用方法是用气雾剂处理，在气雾剂中化合物可溶解在气雾剂载体中，该载体在压力下是液体，但在常温(例如，20℃)和大气压力下是气体。气雾剂还可通过首先把化合物溶解在低挥发性的溶剂中，然后把所得溶液与高挥发性的液体气雾剂载体混合的方式制备。
用农药处理植物时(这期间包括植物局部)本发明化合物最好是以含有表面活性分散剂的水乳液的形式施用，表面活性分散剂可以是非离子型的，阳离子型的或阴离子型的。适合的表面活性剂包括那些现有技术中已知的，如那些公开在美国专利2,547,724(3和4栏)中的。本发明的化合物，在存在或不存在有机溶剂下可与上述的表面活性分散剂混合，得到的浓缩物用于随后添加水，而获得在所需浓度水平的化合物的水悬浮液。
另外，化合物可与本身即具有农药活性的载体如杀虫剂，杀螨剂，杀真菌剂或杀细菌剂体一起使用。
可以理解到在所给制剂中农药活性化合物的量，将取决于具体被防止的有害生物，以及使用的化合物的具体化学组成和剂型，施用化合物/制剂的方法和处理的生长地。因此化合物的有效量可以非常宽。但是，通常在有效的农药制剂中作为活性成分化合物的浓度可在大约0.1％到大约95％重量范围内。稀释的喷雾液可低到每百万分之几份，同时在相反的极限，化合物的高浓度的浓缩物，可用超低容量技术施用。在处理的植物生长地，每单位面积的浓度可在每英亩大约0.01到大约50磅范围内，当施用在如玉米，烟草，水稻和类似的作物上时，浓度在每英亩大约0.1到大约10磅范围内。
为了防治有害生物，喷施的化合物应直接施用到有害生物和/或它们生长或隐蔽的植物上。活性的农药制剂还可以施用在有害生物存在的土壤或其它介质中。
有害的昆虫，线虫和螨攻击多种植物，其中包括观赏植物和农作物，并通过吃光根和/或叶，从植物中抽取维持生命必需的汁液，分泌毒素并经常传播疾病使植物受到损害。本发明化合物可有益地用于减少或防止上述损害，具体的施用方法，以及这些化合物和浓度的选择将理所当然地依赖于环境地理位置、气候、地形、植物忍耐性，等的变化。对于具体的环境，通过常规试验，本领域的熟练者可很容易确定适当的化合物，浓度和施用方法。
本发明的化合物特别适用于作为叶面和/或土壤施用的杀虫剂，杀线虫剂和杀螨剂。
下述的实施例将要进一步地解释本发明，且不以任何方式限制本发明的范围。
实施例1
(4-甲氧基-[1，1′-二苯基]-3-基)肼氢氯化物(化学中间体)的制备
把25g5-苯基-0-茴香胺加入250ml水和450ml的浓盐酸，并把搅拌溶液冷却到0℃。然后滴加入8.6g亚硝酸钠的20ml水溶液，保持温度在0℃。添加完后在0℃，搅拌混合物1小时。把冷却至-20℃的，113g氯化亚锡的200ml浓盐酸溶液加入到反应混合物中，再搅拌混合物一小时。然后空吸过滤混合物并使所得固体干燥过夜。将固体溶于热水中，重力过滤，在冰上冷却滤液。然后空吸过滤结晶的固体，并使产物干燥过夜。获得26g(4-甲氧基-[1，1′-二苯基]-3-基)肼氢氯化物的产物。
实施例2
2-(4-甲氧基[1，2′-二苯基]-3-基)肼的丙酸化物的制备(化合物18)
把5g实施例1的产物加入到100ml水和40ml 10％氢氧化钠溶液中，并在室温下搅拌混合物1小时。然后用乙醚提取混合物，用硫酸钠充分干燥醚提取物半小时。然后过滤醚提取物并在减压下蒸发得到4.6g的中间体，(4-甲氧基-[1，1′-二苯基]-3-基)肼。
把150ml甲苯和1.58g吡啶加入到上述4.6g中间体中，搅拌溶液并冷却到0℃。然后，滴加入1.84g丙酰氯。加入丙酰氯后，在0℃搅拌溶液1小时。然后用每次100ml水洗涤溶液两次。收集水部分，用甲苯提取。合并提取的甲苯部分减压下蒸发。所得固体用己烷洗涤并过滤。获得3.4g的2-(4-甲氧基-[1，1′-二苯基]-3-基)肼的丙酸化物的产物
实施例3
2-(4-甲氧基-[1，1′-二苯基]-3-基)-2-(三氟乙酰基)肼的丙酸化物(化合物73)的制备
向2.25g的实施例2产物中加入150ml的二氯甲烷。搅拌溶液并冷却到0℃。然后滴加入1.75g的三氟乙酸酐，塞紧烧瓶，搅拌反应过夜。然后减压下蒸发溶剂，得到的固体用己烷洗涤并过滤。获得2.7g的最终产物2-(4-甲氧基-[1，1′-二苯基]-3-基)-2-(三氟乙酰基)肼的丙酸化物，熔点为126℃。
实施例4
(4-溴[1，1′-二苯基]-3-基)肼氢氯化物(化学中间体)的制备
伴随搅拌，向4g的4-溴-[1，1′-二苯基]-3-胺中加入25ml的水和50ml浓HCl中。把溶液冷却到0℃。然后滴加入1.1g亚硝酸钠的6ml水溶液，保持温度为0℃。加完后，将混合物在0℃搅拌一小时，把冷却到-20℃的20g氯化亚锡的20ml浓HCl溶液加入到反应混合物中，再搅拌混合物一小时。
然后将沉淀空吸过滤，并使所得固体干燥过夜。产物，(4-溴-[1，1′-二苯基]肼氢氯化物，不需要进一步提纯，用于随后的反应。
实施例5
2-(4-溴-[1，1′-二苯基]-3-基)肼羧酸异丙基酯(化合物139)的制备
把实施例4的产物加入到100ml 10％氢氧化钠水溶液中。在10℃搅拌混合物30分钟。然后用乙醚提取混合物。用硫酸钠充分干燥2小时并蒸发，剩下3g的(4-溴-[1，1′-二苯基]-3-基)肼。向这3g肼加入100ml甲苯和1.5g吡啶，并在冰浴中冷却所得混合物。滴加入12ml 1M的氯甲酸异丙酯的甲苯溶液。加入氯甲酸异丙酯后，使溶液在室温下搅拌过夜。然后洗涤溶液两次，每次用100ml水，用硫酸钠充分干燥2小时，减压条件下蒸发。
用己烷洗涤所得固体，并从甲苯中重结晶。获得3g，熔点为107-108℃的产物2-(4-溴[1，1′-二苯基]-3-基)肼羧酸异丙基酯。
实施例6
(4-溴-[1，1′-二苯基]-3-基)二氮烯羧酸异丙基酯(化合物161)的制备
向1.7g实施例4的产物加入100ml甲苯和0.4g披钯木炭，在室温下搅拌混合物过夜，然后过滤产物并在减压下蒸发甲苯。获得1.5g红色油状的产物(4-溴-[1，1′-二苯基]-3-基)二氮烯羧酸异丙基酯。
实施例7
2-甲氧基-3-二苯并呋喃基肼(化学中间体)的制备
伴随搅拌，向10g3-氨基-2-甲氧基二苯并呋喃加入100ml水和50ml浓Hcl。把溶液冷却至0℃。然后滴加入3.5g亚硝酸钠的15ml水溶液，保持温度在0℃。加完后，在0℃搅拌混合物一小时。把冷却到-20℃的40g氯化亚锡的50ml浓Hcl溶液加入到反应混合物中，搅拌混合物一小时。
空吸过滤沉淀，把所得固体加入到冰浴冷却的70g氢氧化钠的500ml水溶液中。然后用乙醚提取混合物，硫酸钠充分干燥2小时，并蒸发成固体，用己烷洗涤固体，剩下7g的2-甲氧基-3-二苯并呋喃基肼，mp113-115℃。
实施例8
2-(2-甲氧基-3-二苯并呋喃基)肼羧酸异丙酯(化合物141)的制备
向2.3g实施例7的产物中加入100ml甲苯和1g吡啶，所得混合物在冰浴中冷却。然后滴加入10ml 1M氯甲酸异丙基酯的甲苯溶液。加完后，使溶液在室温下搅拌过夜。
然后洗涤溶液两次，每次用100ml水，用硫酸钠充分干燥二小时，然后减压下蒸发。所得固体用己烷洗涤，用甲苯重结晶。获得2g的产物2-(2-甲氧基-3-二苯并呋喃基)肼羧酸异丙酯mp178℃。
实施例9
(2-甲氧基-3-二苯并呋喃基)二氮烯羧酸异丙基酯(化合物157)的制备
向1.4g实施例7的产物中加入100ml甲苯和0.3披钯木炭。在室温下搅拌混合物过夜，过滤，减压下蒸发甲苯。获得1.2g如红色油状的产物(2-甲氧基-3-二苯并呋喃基)二氮烯羧酸异丙基酯。
采用示于上述实施例中的基本相同的方法，制备归纳在表1-4B并编号为1-161的化合物。那些不能从商业上获得的起始产物，通过现有技术中已知的方法合成。每个化合物的结构特征，通过它们的核磁共振谱鉴别。
表1
Figure C9211462200161
化合物    X        R           Z         表1的NMR数据1        2-C6H5    CH3         O    s(3)1.9；m(10)6.8-7.5；bs(1)9.92        2-C6H5    OCH3        O    s(3)3.6；s(1)6.5；m(9)6.8-7.5；bs(1)9.13        2-C6H5    OCH2CH3     O    t(3)1.2；q(2)4.0；s(1)6.5；
                                m(9)6.7-7.5；bs(1)9.04        2-C6H5    C(CH3)3     O    s(9)1.2；m(10)6.8-7.5；bs(1)9.75        2-C6H5    C5H9-c      O    m(8)1.4-1.8；m(1)2.4-2.8；d(1)6.5；
                                m(9)6.7-7.5；d(1)9.86        2-C6H5    OCH2C6H5    O    s(2)5.1；s(1)6.5；m(14)6.8-7.5；s(1)9.87        2-C6H5    OCH(CH3)2   O    d(6)1.2；m(1)4.9；bs(1)5.9；bs(1)6.3；
                                m(9)6.8-7.58        3-C6H5    CH3         O    s(3)2.0；m(9)6.8-7.5；bs(1)8.7；bs(1)9.7表1(续)化合物    X               R           Z        表1的NMR数据9    2-CH3O，5-C6H5    CH2Cl         O     s(3)3.8；s(2)3.9；m(9)6.9-7.6；bs(1)9.810    2-CH3O，5-C6H5    OCH3          O     s(3)3.7；s(3)3.8；bs(1)6.2；m(9)6.7-7.511    2-CH3O，5-C6H5    OCH2CH3       O     t(3)1.2；s(3)3.8；q(2)4.2；bs(1)6.3；
                                        bs(1)6.4；m(8)6.7-7.512    2-CH3O,5-C6H5      CH2CH2CH3    O     t(3)0.9；m(2)1.5；t(2)2.2；s(3)3.8；
                                        m(9)6.8-7.5；d(1)9.813    2-CH3O，5-C6H5    CH(CH3)2      O     d(6)0.9；m(1)2.9；s(3)3.8；m(9)6.8-7.5
                                        bs(1)9.814    2-CH3O，5-C6H5    C(CH3)3       O     s(9)1.1；s(3)3.8；m(9)6.8-7.5；bs(1)9.815    2-CH3O，5-C6H5    OCH2C6H5      O     s(3)3.9；s(2)5.0；m(2)6.4；m(8)6.9-7.616    2-CH3O，5-C6H5    CH20CH3       O     s(3)3.3；s(3)3.8；s(2)4.0；bs(1)6.5；
                                        m(8)6.7-7.5；bs(1)8.317    2-CH3O，5-C6H5    C(CH3)＝CH2   O     s(3)2.0；s(3)3.8；s(1)5.2；s(1)5.7；
                                        bs(1)6.5；m(8)6.7-7.5；bs(1)8.318    2-CH3O，5-C6H5    CH2CH3        O     t(3)1.2；q(2)2.3；s(3)3.8；bs(1)6.5；
                                        m(8)6.8-7.5；bs(1)8.3表1(续)化合物        X             R         Z          表1的NMR数据19    2-CH3O，5-C6H5    O(CH2)3CH3   O     t(3)0.9；m(4)1.5；s(3)3.8；t(2)4.1；
                                        bs(1)6.5；m(8)6.8-7.520    2-CH3O，5-C6H5    OCH2CH2CH3    O     t(3)0.9;m(2)1，6；s(3)3.8；t(2)4.1；
                                        bs(1)6.3；bs(1)6.5；m(8)6.8-7.521    2-CH3O，5-C6H5    OCH2CH(CH3)2 O     d(6)0.9；m(1)1.9；s(3)3.8；d(2)3.9；
                                        bs(1)6.3；bs(1)6.6；m(8)6.8-7.522    2-CH3O，5-C6H5    NHC3H7        S     t(3)1.0；m(2)1.7；q(2)3.6；s(3)3.9；
                                        s(1)6.5；m(9)6.8-7.5；s(1)8.523    2-CH3O，5-C6H5    CO2CH2CH3     O     t(3)1.2；s(3)3.8；q(2)4.2；m(8)6.8-7.5；
                                        bs(1)8.3；bs(1)9.824    2-CH3O，5-C6H5    SCH2CH3       O     t(3)1.2；q(2)2.7；s(3)3.6；m(9)6.8-7.5；
                                        b((1)9.525    2-CH3O，5-C6H5    OCH2CH-CH2    O     (3)3.8；d(2)4.6；m(3)5.1-6.0；bs(1)6.3；
                                        bs(1)6.5；m(8) 6.8-7.526    2-CH3O，5-C6H5    OCH(CH3)2     O     d(6)1.2；s(3)3.8；m(1)5.0；bs(1)6.3；
                                        bs(1)6.5；m(8)6.8-7.5表1(续)化合物        X                R          Z        表1的NMR数据27    2-CH3O，5-C6H5    CH2C(CH3)3       O    s(9)1.0；s(2)2.1；s(3)3.8；bs(1)6.5；
                                           m(8)6.8-7.528    2-CH3O，5-C6H5    CF2CF3           O    s(3)3.8；m(8)6.8-7.5；bs(2)8.229    2-CH3O，5-C6H5    CF2Cl            O    s(3)3.8；bs(1)6.0；m(8)6.8-7.5；bs(1)8.230    2-CH3O，5-C6H5    2-C4H3S          O    s(3)3.8；m(13)6.7-7.931    2-C6H5            H                O    m(10)6.7-7.5；bs(1)8.1；bs(1)9.9；32    2-C6H5            CF3             O    m(11)6.7-7.533    2-CH3O，5-C6H5 H               O    s(3)3.9；m(9)6.9-7.7；bs(1)8.1；bs(1)9.834    2-CH3O，5-C6H5 CH3            O    s(3)2.0；3(3)3.8；m(10)6.8-7.735    2-CH3O，5-C6H5 CF3            O    s(3)3.8；m(10)6.8-7.736    2-CH3O，5-C6H5 CHClCH3        O    d(3)1.5；s(3)3.9；q(1)37    2-CH3O，5-C6H5 CH2C6H5     O    s(2)3.5；s(3)3.9；m(15)5.8-7.438    2-CH3O，5-C6H5 cyclohexyl      O    m(11)1.1-1.8；s(3)3.8，
                                           m(9)6.8-7.5；bs(1)9.839    2-CH3O，5-C6H5 OCH2CH2OCH3 O    s(3)3.3；t(2)3.5；s(3)3.8；t(2)4.2；
                                           bs(1)6.3；m(9)6.8-7.5表1(续)化合物         X             R               Z    表1的NMR数据40    2-CH3O，5-C6H5  OCHClCH3        O    d(3)1.8；s(3)3.8；m(1)6.5；m(10)6.8-7.641    2-CH3O，5-C6H5  OC6H5          O    s(3)3.8；m(15)6.5-7.842    2-C6H5           OC3H7          O    m(5)0.8-1.7；m(2)4.1；bs(1)5.9
                                               m(10)6.7-7.543    2-C6H5           OCH4H9         O    m(7)0.8-1.7；m(2)4.1；bs(1)5.9
                                               m(10)6.7-7.644    2-CH3O，5-C6H5  OCH＝CH2        O    s(3)3.8；m(2)4.5-5.0
                                               bs(1)6.2；m(10)6.7-7.645    2-CH3O，5-C6H5  OC(CH3)2CCl3  O    s(6)1.9；s(3)3.9；bs(1)6.2；m(9)6.8-7.646    2-CH3O，5-C6H5  O-cyclohexyl-     O    m(8)1.0-2.2；s(3)3.9；m(10)6.5-7.5
                        3-Cl47    2-CH3O，5-C6H5  OCH2CH2Cl         O    m(2)3.6；s(3)3.8；m(2)4.3；bs(1)6.2
                                               m(9)6.7-7.648    2-CH3O，5-C6H5  CCl3             O    s(3)3.9；m(10)6.8-7.849    2-CH3O，5-C6H5  OCH2CH-CH2     O    d(2)4.5；m(3)5.0-6.0；m(11)6.7-7.6表1(续)化合物        X                R        Z     表1的NMR数据50     3-C6H5          OCH(CH3)2  O     d(6)1.2；m(1)4.9；bs(1)6.0；m(10)6.7-7.551     3-C6H5          OC2H5      O     t(3)1.2；q(2)4.1；bs(1)5.9；m(10)6.7-7.652     2-CH3O，5-C6H5 OCH(CH3)2  O     m(9)1.2-1.6；m(2)4.0-4.3；m(1)4.8-5.2；
                                           bs(1)6.4；m(9)6.8-7.653     2-C6H5          OC5H11     O      m(9)0.8-1.7；m(2)3.9-4.2；bs(1)5.9
                                           m(10)6.7-7.554     2-CH3O，5-C6H5  OC5H11    O      m(9)0.8-1.7；s(3)3.8；t(2)4.1；bs(1)6.3；
                                           m(9)6.7-7.555     2-CH3O，5-C6H5 OC6H13     O      m(11)0.8-1.7；s(3)3.9；t(2)4.1；bs(1)6.3；
                                           m(9)6.7-7.5136    3-OCH2C6H5     C2H5       O     t(3)1.2；q(2)4.1；s(2)5.0；bs(2)6.3；
                                           m(9)6.9-7.4137    3-OCH2C6H5     CH(CH3)2   O     d(6)1.3；m(1)5.0；s(2)5.1；bs(2)6.5；
                                           m(9)6.9-7.5138    3-OC6H5         CH(CH3)2   O      s(9)1.4；bs(2)6.5；m(9)6.9-7.5139    2-Br，5-C6H5    CH(CH3)2   O      d(6)1.3；m(1)5.0；bs(1)6.3；m(8)6.9-7.5表1(续)化合物          X            R              Z          表1的NMR数据140    3-OC6H5          CH(CH3)2      O      d(6)1.3；m(1)5.0；bs(2)6.6；m(9)6.9-7.5143    3-OCH2C6H5      CH3            O      s(3)3.8；s(2)5.0；bs(2)6.5；m(9)7.0-7.5144    3-OCH2C6H5      CH2CH＝CH2    O      d(2)4.5；m(3)5.1-6.0；bs(2)6.5；
                                                m(9)6.9-7.5145    2-CH2C6H5       C3H7          O      t(3)0.8；m(2)1.5；s(2)3.8；m(2)3.9；
                                                bs(2)6.4；m(9)6.9-7.3146    2-CH2C6H5       CH2CH＝CH2    O      s(2)3.9；d(2)4.5；m(3)5.0-5.8；bs(2)6.6；
                                                m(9)6.8-7.3147    3-OCH2C6H5      C(CH3)3       O      s(9)1.4；s(2)5.0；bs(2)6.5；m(9)6.9-7.4148    2-CH2C6H5       C(CH3)3       O      s(9)1.4；s(2)3.9；bs(2)6.2；m(9)6.9-7.3149    3-OC6H5          CH(CH3)C2H5  O      t(3)0.8；d(3)1.2；m(2)1.5；m(1)4.8；
                                                bs(2)6.5；m(9)6.9-7.4150    2-SCH3，5-C6H5  CH(CH3)2      O      d(6)1.2；s(3)2.4；m(1)4.9；bs(2)6.6；
                                                m(8)7.0-7.5表1(续)化合物         X             R          Z     表1的NMR数据154    2-CH3，5-C6H5   CH(CH3)2  O     d(6)1.2；s(3)2.2；m(1)4.9；bs(1)5.8；
                                          bs(1)6.6；m(8)7.0-7.6155    2-OCH3，5-OC6H5 CH(CH3)2  O     d(6)1.3；s(3)3.8；m(1)4.9；m(10)6.5-7.4
表1-4B注释(1)s＝单峰，d＝双峰,t＝三峰，q＝四峰，m＝多峰，bs-宽单峰(2)括号中的数字表示质子数(3)CDCL3是氘化的氯仿
表2
Figure C9211462200241
化合物      X             R               表2的NMR数据
56    2-C6H5            H          bs(1)5.8；m(9)6.8-7.5；bs(1)8.1
57    2-C6H5            CH3        s(3)2.5；bs(1)6.0；m(9)6.8-7.5
58    2-C6H5            OCH3       s(3)3.7；bs(1)5.7；m(9)7.3-7.6
59    2-C6H5            OCH2CH3    t(3)1.2；q(2)4.2；m(9)7.3-7.7；bs(1)9.7
60    2-C6H5            C(CH3)3    s(9)1.2；m(10)6.8-7.6
61    2-C6H5            C5H9-C     m(8)1.7；m(10)6.8-7.6
62    2-C6H5            OCH2O6H5   s(2)5.2；bs(1)6.9；m(9)7.3-7.6
63    3-C6H5            CH3        s(3)2.0；m(9)7.3-7.9；bs(1)8.5
64    2-CH3O，5-C6H5    H          s(3)3.9；b(1)5.5；m(8)7.0-7.7；bs(1)8.3
65    2-CH3O，5-C6H5    CH3        s(3)2.0；s(3)3.8；bs(1)6.1；m(8)6.9-7.7
66    2-CH3O，5-C6H5    OCH3       s(3)3.7；s(3)3.9；bs(1)4.2；m(8)7.3-7.8
67    2-CH3O，5-C6H5    OCH2CH3    t(3)1.1；s(3)3.8，q(2)4.1；m(9)7.2-7.9表2(续)化合物          X            R                   表2的NMR数据68    2-CH3O，5-C6H5    N(CH3)2            s(6)3.0；s(3)3.9；m(9)7.0-7.969    2-CH3O，5-C6H5    CH2CH2CH3          t(3)1.0；m(2)1.7；t(2)3.0；s(3)3.9；
                                         m(8)7.0-7.7；bs(1)8.270    2-CH3O，5-C6H5    CH(CH3)2           d(6)1.0；m(1)2.5；s(3)3.9；bs(1)5.4；
                                         m(8)7.0-7.971    2-CH3O，5-C6H5    C(CH3)3            s(9)1.2；s(3)3.9；m(8)7.0-7.9；bs(1)8.372    2-CH3O，5-C6H5    OCH2C6H5           s(3)3.8；s(2)5.1；m(8)7.1-7.8；bs(1)9.573    2-CH3O，5-C6H5    CH2CH3             t(3)1.1；q(2)；s(3)3.8；
                                         m(8)7.0-7.8；bs(1)8.174    2-CH3O，5-C6H5    OCH2CH2CH2CH3      m(7)0.8-1.7；s(3)3.9；t(2)4.1；
                                         m(9)7.0-7.875    2-CH3O，5-C6H5    C(CH3)＝CH2        s(3)2.0；s(3)3.9；m(2)5.4-5.7；
                                         m(8)7.0-7.8；bs(1)8.376    2-CH3O，5-C6H5    CF3                s(3)3.9；m(9)7.1-7.877    2-CH3O，5-C6H5    N(CH2CH3)2         t(6)1.2；m(4)3.3；s(3)3.8；m(9)7.0-8.079    2-CH3O，5-C6H5    SCH2CH3            t(3)1.2；q(2)2.8；s(3)3.9；m(9)7.2-7.8表2(续)化合物         X                R                表2的NMR数据78    2-CH3O，5-C6H5    CO2CH2CH3          t(3)1.3；s(3)3.8；q(2)4.2；m(8)7.0-7.9；
                                        bs(1)9.580    2-CH3O，5-C6H5    OCH2CH＝CH2        s(3)3.9；d(2)4.6；m(3)5.1-5.8；
                                        m(9)7.0-7.781    2-CH3O，5-C6H5    OCH(CH3)2          d(6)1.2；s(3)3.8；m(1)4.9；m(9)7.0-7.782    2-CH3O，5-C6H5    CH2C(CH3)3         s(9)1.0；s(2)2.2；s(3)3.9；m(8)7.0-7.8；
                                        bs(1)8.683    2-CH3O，5-C6H5    CF2C1             s(3)3.9；m(9)7.0-8.084    2-CH3O，5-C6H5    2-C4H3S            s(3)3.9；m(12)7.0-8.085    2-CH3O，5-C6H5    2-C4H3O            s(3)3.9；bs(1)6.5；m(11)7.0-8.086    2-CH3O，5-C6H5    OCH2CH3          m(6)1.3；m(4)4.2；m(9)7.0-7.887    2-CH3O，5-C6H5 CH2Cl            s(3)3.9；s(2)4.0；m(9)6.9-7.788    2-CH3O，5-C6H5 CH2C6H5       s(2)3.7；s(3)3.8；m(14)6.8-7.989    2-CH3O，5-C6H5 cyclohexyl        m(11)1.1-1.9；s(3)3.9；m(9)6.8-7.9表2(续)化合物         X                R                表2的NMR数据90    2-CH3O，5-C6H5 OC3H7             t(3)1.9；m(2)1.6；s(3)3.9；t(2)4.1；
                                           m(9)6.9-7.891    2-CH3O，5-C6H5 CH2OCH3           s(3)3.4；s(3)3.9；s(2)4.0；m(9)6.9-7.992    2-CH3O，5-C6H5 OCH2CH(CH3)2     d(6)0.9；m(1)1.8；s(3)3.9；d(2)4.0；
                                           m(9)6.9-7.893    2-C6H5          OCH2CH(CH3)        d(6)0.9；m(1)1.8；d(2)3.9；bs(1)6.1；
                                           m(9)7.2-7.794    2-CH3O，5-C6H5 CH3                 t(3)1.5；s(3)2.0；s(3)4.1；m(8)6.9-7.8；
                                           bs(1)8.395    2-CH3O，5-C6H5 OCH(CH3)2         d(6)1.3；m(1)5.0；m(9)7.3-7.8；bs(1)10.796    2-CH3O，5-C6H5 OCH2CH2Cl            t(2)3.7；s(3)3.9；t(2)4.3；m(9)6.9-7.897    2-CH3O，5-C6H5 OC6H5             s(3)3.9；m(14)6.8-7.998    2-CH3O，5-C6H5 OC4H9             m(7)0.8-1.7；m(2)4.1；bs(1)6.2
                                           m(9)7.2-7.699    2-C6H5          OC3H7              m(5)0.8-1.6；m(2)4.0；bs(1)6.2；
                                           m(9)7.0-7.7表2(续)化合物         X              R                   表2的NMR数据100    2-CH3O，5-C6H5  OCH-CH2        s(3)3.9；m(2)4.5-5.0；s(1)6.2；
                                         m(10)6.8-7.8101    2-CH3O，5-C6H5  OC5H11         m(9)0.8-1.6；s(3)3.8；m(2)4.1-6.2；
                                         m(9)6.8-7.7102    2-CH3O，5-C6H5  OC6H13          m(11)0.8-1.6；s(3)3.8；m(2)4.1；m(9)
                                         6.8-7.7
表1-4B注释(1)s＝单峰，d＝双峰，t＝三峰，q＝四峰，m＝多峰，bs-宽单峰(2)括号中的数字表示质子数(3)CDCL3是氘化的氯仿
表3化合物      X            R                 表3的NMR数据103    COCH3          CF3            s(3)2.0；s(3)3.9；m(9)7.2-7.8104    COCH2Cl        CH3            s(3)2.3；s(3)3.9；s(2)4.5；m(9)7.2-7.8105    COCF2CF3       CH3            s(3)2.5；s(3)3.9；m(9)7.0-7.6106    COCF2CF3       OCH3           s(3)3.4；s(3)3.9；s(2)4.0；m(8)7.0-8.0；
                                   bs(1)8.8107    COCH2CH3       CF3            t(3)1.0；m(2)2.2；s(3)3.9；m(8)7.0-7.9；
                                   bs(1)9.0108    CO2CH2CH3      CF3            t(3)1.2；s(3)3.9；q(2)4.2；m(9)7.0-7.8109    CONHCH3        OCH2CH3        t(3)1.2；d(3)2.9；s(3)3.9；m(10)7.0-7.8110    COCH3         CH3          s(3)2.0；s(3)3.4；s(3)3.9；m(8)6.9-7.7；
                                   bs(1)9.8111    COCF2Cl       CH3          s(3)2.0；s(3)3.9；m(9)6.7-7.8表3(续)化合物     X              R                 表3的NMR数据112    COCH3          CF2CF3       s(3)2.0；s(3)3.9；m(8)6.9-7.8；bs(1)8.9113    COCH3          CF2Cl         s(3)2.0；s(3)3.9；m(8)6.9-7.8；bs(1)8.7114    COCF2CF3      CF3           s(3)3.9；m(9)6.9-7.9115    COCF2Cl        CF3           s(3)3.9；m(9)6.9-7.8116    PO(OC2H5)2    CF3           t(6)1.3；s(3)3.8；q(4)4.2；m(9)6.8-7.5117    COCH2Cl        CF3           s(3)3.9；s(2)4.1；m(9)6.8-7.8118    COCF2CF3      OCH(CH3)2   d(6)1.2；s(3)3.9；m(1)4.9；m(9)6.9-7.8119    COCF2Cl        OCH(CH3)2    d(6)1.2；s(3)3.8；m(1)4.9；m(9)6.9-7.8120    CONHCH3        OCH(CH3)2    d(6)1.2；d(3)2.8；s(3)3.8；m(1)4.9；
                                    m(1)5.3；m(9)6.9-7.8121    COCCl3         CF3           s(3)3.9；m(9)6.8-7.7122    CON(CH3)2     OCH(CH3)2   d(6)1.4；s(6)2.7；s(3)3.9；m(1)5.0；
                                    m(9)6.8-7.8123    COCF2CF3      CF2Cl         d(3)3.8；m(8)6.8-7.8；bs(1)8.5124    COCF2CF3      CF3           d(3)3.8；m(8)6.8-7.7；bs(1)8.6125    SO2CF3        CF3           d(3)3.8；m(9)6.8-7.8表3(续)化合物    X               R                  表3的NMR数据126    CO2CH3         CF3             s(3)3.8；s(3)3.9；m(9)6.8-7.8127    COCF2CF3       OCH2C6H5     s(3)3.8；s(2)5.0；m(14)6.8-7.8128    CONHCH3         CF3             bs(3)2.7；s(3)3.8；bs(1)5.5；
                                       m(8)6.8-7.8；s(1)9.2129    COCH3           OCH3            s(3)3.7；s(3)3.8；m(9)6.8-7.8130    CONHC2H5       CF3             t(3)1.1；m(2)3.1；s(3)3.8；bs(1)5.8；
                                       m(9)6.8-7.8131    CONHC2H5       OCH(CH3)2      m(9)1.2；m(2)3.2；s(3)3.8；m(1)4.9；
                                       m(9)6.8-7.8132    COCH3           OCH-CH2         s(3)2.0；s(3)3.8；m(2)4.4-4.9；m(1)6.5；
                                       m(9)6.8-7.8133    PO(OCH2H5)2   OCH(CH3)2      m(12)1.3；s(3)3.9；m(4)4.1；m(1)5.0；
                                       m(9)6.8-7.7134    PO(OC2H5)2    OCH2CH3        m(9)1.2；s(3)3.8；q(6)4.1；m(9)6.8-7.7
表1-4B注释(1)s＝单峰，d＝双峰，t＝三峰，q＝四峰，m＝多峰，bs-宽单峰(2)括号中的数字表示质子数(3)CDCl3是氘化的氯仿
表4
Figure C9211462200321
化合物        X                R                    表4的NMR数据135    2-CH3O，5-C6H5       OCH(CH3)2   d(6)1.5；s(3)4.0；m(1)5.2；m(8)7.0-7.9156    3-OC6H5           OC(CH3)3   s(9)1.6；m(9)7.0-7.5158    3-OCH2C6H5       OC2H5      t(3)1.4；q(2)4.4；s(2)5.0；m(9)7.1-7.5159    2-CH3，5-C6H5    OCH(CH3)2  d(6)1.5；s(3)2.7；m(1)5.2；m(8)7.2-7.8160    2-OCH3，5-OC6H5  OCH(CH3)2  d(6)1.4；s(3)4.0；m(1)5.2；m(8)6.9-7.4161    2-Br，5-C6H5      OCH(CH3)2  d(6)1.5；m(1)5.3；m(8)7.0-7.7表4A
Figure C9211462200331
化合物    R                        表4A的NMR数据141    CH(CH3)2         d(6)1.2；s(3)3.9；m(1)5.0；bs(2)6.5；m(6)7.0-7.6142    C(CH3)3             s(9)1.5；s(3)d.0；bs(2)6.5；m(6)7.1-7.6151    CH2CH-CH2        s(3)4.0；d(2)4.7；m(3)5.1-5.8；bs(2)6.5；m(6)7.1-7.6152    CH3               s(3)3.8；s(3)4.0；bs(2)6.5；m(6)7.0-7.6153    C3H7             t(3)1.0；m(2)1.6；s(3)4.0；m(2)4.2；bs(2)6.6；m(6)7.1-7.6
表4B化合物    R                        表4B的NMR数据(CDCL3)157    CH(CH3)2         d(6)1.4；s(3)4.1；m(6)7.1-7.7实施例10
制剂的制备
以下的实施例涉及本发明化合物的农药用途。在所有这些实施例中，3000ppm的化合物的储液的制备，是通过把0.3的供试化合物溶于10ml丙酮中，并加入滴加了山梨醇单月桂酸酯的乙氧基化物，或类似的适合的湿润剂的90ml蒸馏水。在下述的每个实施例中，使用该储液并制备具体的稀释液。在下述讨论的包括供处理的本发明化合物的所有试验中，全部用对照重复，对照中未提供活性化合物，以比较计算的防治百分率。
实施例11
杀成螨剂和杀螨卵剂/杀幼螨剂试验
处理前一天，将树粘虫胶在两个豇豆初生叶的每个叶子上涂成“8”字形，每个盆中有两株植物，在每个“8”字形中，较接近植物茎的环设计作杀螨卵剂/杀幼螨剂试验，而离茎较远的环设计作杀成螨剂试验。
处理的前一天，将数组成螨(Tetranychus urticaekoch)转移至杀卵剂环，并使雌螨产卵，直到处理前一小时再将螨移去。用从3000ppm储液稀释的1000ppm溶液喷雾冲洗处理植物。
处理后一天，大约25头一组的成螨移至杀成螨环。五天后观察这些环中，留在叶子上的活螨。以对照植物上存活螨的数目为基数评价防治百分率。
处理后九天观察杀螨卵剂/杀幼螨剂环中孵化的卵和成活的幼螨，以对照植物上孵化的卵和存活的幼螨的数目为基数评价防治百分率。当处理对卵有效，这种防治指定为是杀卵的(O)，当处理对幼螨有效，这种防治指定为是杀幼螨的(L)。
杀成螨剂(MI)和杀螨卵剂/杀幼螨剂(MIOLV)的试验结果示于表5中。
   表5
 化合物序号
   NO.          MI           MIOVL
    1           50           80(L)
    2           100          100
    3           100          100(L)
    4           100          100(L)
    5           30           80(L)
    6           100          100(L)
    7           100          100(O)
    8           70           0
    9           70           0
    10          100          100(O/L)
    11          100          100(O/L)
    12          95           90(L)
    13          70           70(L)
    14          100          100(L)
    15          100          100(L)
    16          100          100(L)
    17          70           0
    18          98           100(L)
    19          100          100(O)
    20          100          100(O)
    21          100          100(O)
    22          100          20(L)表五(续)
    化合物序号
                  MI             MIOVL
        23        70             0
        24        100            70(L)
        25        100            100(O)
        26        100            100(O)
        27        99             50(L)
        28        100            100(L)
        29        80             80(L)
        30        50             50(L)
        39        100            100(L)
        40        50             0
        41        80             50(L)
        42        100            100(O)
        43        100            100(O)
        44        50             30(L)
        45        70             50(L)
        46        100            30(L)
        47        100            100(L)
        49        100            100(O)
        50        100            100(O)
        51        100            100(O)
        52        1000           100(O)
        53        100            100(L)
        54        100            100(O)
        55        100            100(O)表5(续)
化合物序号
              MI         MIOVL
    56        70         0
    57        90         95(L)
    58        100        30
    59        100        0
    60        100        100(L)
    62        98         50(L)
    63        100        70(L)
    64        100        100(L)
    65        100        100(L)
    66        70         50(L)
    67        90         95(L)
    68        100        100(L)
    69        100        100(L)
    70        100        100(L)
    72        0          50(L)
    73        100        100(L)
    74        99         30(L)
    75        100        100(L)
    76        100        100(L)
    77        100        100(L)
    78        100        100(L)
    79        70         70(L)
    80        100        70(L)
    81        99         90(L)表5(续)
    化合物序号
                  MI         MIOVL
        82        95         30(L)
        83        100        100(L)
        84        100        100(L)
        85        100        100(L)
        86        100        100(L)
        93        100        80(l)
        94        100        100(L)
        95        100        100(L)
        96        100        100(L)
        97        70         30(L)
        98        100        100(L)
        99        100        100(L)
        101       70         80(L)
        102       70         0
        105       95         0
        107       100        50(L)
        108       100        100(O)
        109       100        100(O)
        112       60         0
        114       100        100(O)
        115       100        100(L)
        116       100        100(L)
        117       100        100(L)
        118       100        100(L)表5(续)
  化合物序号
    NO.        MI         MIOVL
    119        100        100(L)
    120        100        100(L)
    121        100        100(L)
    122        100        100(O)
    124        100        100(L)
    125        80         30(L)
    126        100        100(L)
    128        100        100(L)
    130        100        50(L)
    131        100        100(L)
    133        100        100(O)
    135        100        100(O)
    136        98         100(L)
    137        100        100(L)
    138        100        98(L)
    139        100        100(L)
    140        100        100(L)
    141        70         100(L)
    142        50         80(L)
    143        70         30(O)
    144        30         0
    145        100        90(L)
    146        70         50(L)
    147        100        100(L)
    148        70         30(L)
    149        30         0表5续
化合物序号
               MI       MIOVL
    150        80         0
    151        0          0
    152        0          0
    153        100        90(L)
    154        100        100(L)
    155        0          0
    156        98         0
    157        30         80(L)
    158        100        98(O)
    159        100        100(O)
    160        100        20(O)
    161        100        100(O)
注释：MI＝杀成螨剂
      MIOVL＝杀螨卵剂/杀幼螨剂
实施例12
榆全爪螨试验
用单个化合物乳油的水溶液喷雾处理被榆全爪螨(Panonychusulmi)侵染的果园苹果树。采用103，10，11，19，20，25，26和82号化合物，在150ppm活性成份的剂量适用时，可获得大于75％的防治率。
实施例13线虫试验
将3000ppm的储液稀释到1000ppm。用25ml每个化合物的溶液浸渍盆中被根结线虫(Meloidogyne incognita)卵浸染的500克土壤，土壤中的浓度为50ppm sc。
处理后一天，每个盆中种植两颗番茄苗。种植后十九天，评价根上出现的结或瘿，以对照植物的侵染水平为基数，评价防治百分率。
线虫(NE)的实验结果示于表6。
实施例14稻飞虱试验
将3000ppm的储液稀释到1000ppm。用喷雾器喷雾每种制剂，处理每盆中含有的大约20株Mars种的水稻幼苗。处理后一天，植物用管状笼覆盖，每个笼中已移入二十只稻飞虱(Sogayode s oryzicola)成虫。移入后五天，计算每个盆中存活的飞虱数，并评价防治百分率。
稻飞虱(RPH)的试验结果示于表6。
实施例15
烟芽夜蛾试验
在本试验中采用3000ppm的储液。将每种化合物的0.2ml溶液用吸管吸至每5个饲料小室的每个的表面上，使溶液分布到小室表面并用空气干燥二小时，然后将二令烟芽夜蛾(Heliothis virescens)成虫引入每个小室。14天后，确定每个处理中存活的成虫数和防治百分率，用Abbott公式校正，并计算。
烟芽夜蛾(TB)的试验结果示于表6。
实施例16
十一星瓜叶甲试验
将3000ppm的储液稀释到100ppm。把每种化合物的2.5ml溶液用吸管吸至滤纸(Whatman#3)上，滤纸置于100mm培替式表面皿上。把两株玉米幼苗浸入100ml溶液中1小时并转移至培替氏表面皿上。24小时后，每个表面皿中放入5头二令Diabrotica undecimpunctata。五天后，记录活幼虫数，和防止百分率，用Abbott公式校正(参见J.Economic Entomology，18，265-267(1925))并计算。
结果示于表6。
表6
   化合物序号               防治百分率
                 NE         RPH      TB        SCR
        1         0         30       100        0
        2         30        100      79         75
        3         0         100      58         50
        4         70        100      100        100
        5         0         0        100        0
        6         0         100      100        0
        7         0         100      100        100
        8         50        PT       0          0
        9         85        0        0          0
        10        0         50       20         0
        11        0         10       100        0
        12        50        0        20         0
        13        0         5        100        0
        14        70        0        0          0
        17        70        0        0          0
        18        0         0        80         0
        19        70        60       0          14
        20        0         0        80         0
        23        95        0        75         0
        24        0         80       0          0
        25        30        0        56         0
        26        20        0        100        0
        27        0         0        56         0
        28        70        0        40         6表6(续)
化合物序号              防治百分率
    NO.       NE       RPH        TB        SCR
    31        50        55        100        15
    33        0         20        100        0
    34        50        15        0          0
    35        100       20        0          0
    36        50        0         0          20
    37        PT        25        80         17
    38        0         0         80         0
    42        0         100       100        100
    43        0         100       100        80
    45        0         0         100        0
    47        80        50        0          20
    48        50        25        0          0
    49        0         80        0          0
    50        30        100       0          100
    51        30        100       100        0
    53        0         100       100        0
    54        0         95        80         0
    55        0         70        40         0
    57        0         35        100        37
    58        0         25        100        0
    59        50        20        100        75
    60        0         40        60         --
    62        0         0         100        0
    64        70        25        0          21表6(续)
化合物序号               防治百分率
               NE       RPH        TB       SCR
    65         60        0         0         0
    67         0         10        100       0
    74         0         0         80        0
    78         95        0         0         14
    80         0         0         78        0
    81         0         50        78        0
    83         30        50        73        16
    84         0         50        20        6
    87         50        0         0         0
    88         50        0         100       0
    89         0         0         60        33
    90         0         0         100       0
    91         0         70        80        0
    92         0         0         75        0
    95         0         25        100       100
    96         30        0         50        20
    99         0         80        0         100
    100        70        60        0         0
    102        70        0         0         0
    103        0         0         100       0
    103        0         0         100       0
    105        0         0         100       0
    106        30        55        0         0
    108        70        0         0         0
    110        0         30        100       0表6(续)
化合物序号       防治百分率
           NE    RPH    TB   SCR
    111    0      0     100   20
    112    50     0     0     0
    113    0      0     100   6
    115    70     50    16    0
    116    60     0     0     60
    117    50     0     55    33
    119    0      40    78    0
    121    50     40    0     0
    125    98     25    0     0
    127    50     50    0     0
    128    70     30    0     0
    129    50     25    0     0
    130    70     15    0     16
    131    70     25    0     16
    132    70     50    0     0
    133    0      55    60    0
    134    70     60    0     0
    135    ---    55    ---   ---
    136    100    30    20    0
    137    100    25    0     100
    138    0      90    0     0
    139    0      98    0     40
    140    0      0     0     0
    141    100    0     60    0
    142    0      0     60    0表6(续)
化合物序号        防治百分率
            NE    RPH     TB    SCR
    143     PT     0      20     20
    144     0      0      0      80
    145     0      0      0      80
    146     0      PT     0      20
    147     0      0      0      100
    148     0      0      0      100
    149     50     0      0      60
    150     0      0      36     0
    151     0      0      60     20
    152     0      0      60     0
    153     50     0      37     0
    154     0      80     58     0
    155     ---    0      75     0
    156     0      0      0      0
    157     100    0      40     0
    158     ---    ---    ---    ---
    159     0      100    58     0
    160     ---    0      0      0
    161     ---    100    100    60注释：NE＝线虫RPH＝稻飞虱TB＝烟芽夜蛾SCR＝十一星瓜叶甲PT＝药害－植物死亡，无适合记号

Claims (7)

1.农药组合物，其中包括
(A)选自下列化合物的农药有效量的化合物；
(a)具有下式的化合物
Figure C9211462200021
其中
X是a)苯基；低级苯基烷氧基；苯氧基；或苯甲基；每个取代基的苯环必要时可被一或多个卤素，硝基，C1-C6烷基，C1-C6烷氧基，C1-C6卤代烷基或二(C1-C6烷基)氨基取代；或b)一个a)组中的取代基和一个或多个选自C1-C6烷氧基；卤素；C1-C6烷基；和C1-C6烷基硫的取代基；
Y是H，C1-C6链烷酰基，C1-C6卤代烷酰基，二(C1-C6烷氧)磷酰基，(C1-C6烷基)氨基羰基，C1-C6卤代烷基磺酰基，或(C1-C6烷氧)羰基；和
R是H，C1-C6烷基，C1-C6烷氧基，C3-C6环烷氧基，C1-C6卤代烷基，C1-C6烷氧(C1-C6烷基)，苯基(C1-C6烷氧基)，C1-C6链烯基，C1-C6烷基硫，(C1-C6烷氧)羰基，C1-C6烷基氨基，硫代苯基，呋喃基，苯基(C1-C6烷基)，C1-C6卤代烷氧基，苯氧基，或C3-C6环烷基；和
Z是O或S；
(b)具有下述结构式的化合物：其中
X是a)苯基；苯基(C1-C6烷氧基)；苯氧基；或苯甲基；每个取代基的苯环必要时可被一或多个卤素，硝基，C1-C6烷基，C1-C6烷氧基，C1-C6卤代烷基或二(C1-C6烷基)氨基取代；或b)一个a)组中的取代基和一个或多个选自C1-C6烷氧基；卤素；C1-C6烷基；和C1-C6烷基硫的取代基；
R是H，C1-C6烷基，C1-C6烷氧基，C1-C6卤代烷基，或C3-C6环烷基；且
Z是O；
(c)具有下述结构式的化合物
Figure C9211462200032
其中
X是氢或C1-C6烷氧基；
R是H，C1-C6烷基，C1-C6烷氧基，C3-C6环烷氧基，C1-C6卤代烷基，C1-C6烷氧(C1-C6烷基)，苯基(C1-C6烷氧基)，C1-C6链烯基，C1-C6烷基硫，(C1-C6烷氧)羰基，C1-C6烷基氨基，硫代苯基，呋喃基，苯基(C1-C6烷基)，C1-C6卤代烷氧基，苯氧基，或C3-C6环烷基；且
Z是O或S，
(d)具有下述结构式的化合物
Figure C9211462200041
其中
X是氢或C1-C6烷氧基，
R是H，C1-C6烷基，C1-C6烷氧基，C3-C6环烷氧基，C1-C6卤代烷基，C1-C6烷氧(C1-C6烷基)，苯基(C1-C6烷氧基)，C1-C6链烯基，C1-C6烷基硫，(C1-C6烷氧)羰基，C1-C6烷氨基，硫代苯基，呋喃基，苯基(C1-C6烷基)，C1-C6卤代烷氧基，苯氧基，或C3-C6环烷基；且
Z是O或S，
(B)适合的载体。
2.根据权利要求1的农药组合物，其中化合物具有下式：其中
X是a)苯基；低级苯基(C1-C6烷氧基)；苯氧基；或苯甲基；每个取代基的苯环必要时可被一或多个卤素，硝基，C1-C6烷基，C1-C6烷氧基，C1-C6卤代烷基或二(C1-C6烷基)氨基取代；或b)一个a)组中的取代基和一个或多个选自C1-C6烷氧基；卤素；C1-C6烷基；和C1-C6烷基硫的取代基；
Y是H，C1-C6链烷酰基，C1-C6卤代烷酰基，二烷氧磷酰基，烷基氨基羰基，卤代烷基磺酰基，或C1-C6烷氧羰基；和
R是H，C1-C6烷基，C1-C6烷氧基，C3-C6环烷氧基，C1-C6卤代烷基，C1-C6烷氧(C1-C6烷基)，苯基(C1-C6烷氧基)，C1-C6链烯基，C1-C6烷基硫，(C1-C6烷氧)羰基，C1-C6烷基氨基，硫代苯基，呋喃基，苯基(C1-C6烷基)，C1-C6卤代烷氧基，苯氧基，或C3-C6环烷基；和
Z是O或S。
3.根据权利要求2的农药组合物，其中
X是苯基或苯基和C1-C6烷氧基；
Y是H或COCF3；
R是CF3，C1-C6烷基，或C1-C6烷氧基，或C3-C6环烷基；且
Z是O。
4.根据权利要求1的农药组合物，其中化合物具有下述结构式：其中
X是a)苯基；苯基(C1-C6烷氧基)；苯氧基；或苯甲基；每个取代基的苯环必要时可被一或多个卤素，硝基，C1-C6烷基，C1-C6烷氧基，C1-C6卤代烷基或二(C1-C6烷基)氨基取代；或b)一个a)组中的取代基和一个或多个选自C1-C6烷氧基；卤素；C1-C6烷基；和C1-C6烷基硫的取代基；
R是H，C1-C6烷基，C1-C6烷氧基，C1-C6卤代烷基，或C3-C6环烷基；且
Z是O。
5.根据权利要求4的化合物，其中X是苯基或C1-C6烷氧基；且R是CF3，C1-C6烷基，C1-C6烷氧基，或C3-C6环烷基。
6.根据权利要求1的农药组合物，其中该化合物具有下述结构式：其中
X是氢或C1-C6烷氧基；
R是H，C1-C6烷基，C1-C6烷氧基，C3-C6环烷氧基，C1-C6卤代烷基，C1-C6烷氧C1-C6烷基，苯基(C1-C6烷氧基)，C1-C6链烯基，C1-C6烷基硫，C1-C6烷氧羰基，C1-C6烷基氨基，硫代苯基，呋喃基，苯基C1-C6烷基，C1-C6卤代烷氧基，苯氧基，或C3-C6环烷基；且
Z是O或S。
7.根据权利要求1的农药组合物，其中化合物具有下述结构式：其中
X是氢或C1-C6烷氧基，
R是H，C1-C6烷基，C1-C6烷氧基，C3-C6环烷氧基，C1-C6卤代烷基，C1-C6烷氧C1-C6烷基，苯基C1-C6烷氧基，C1-C6链烯基，C1-C6烷基硫，C1-C6烷氧羰基，C1-C6烷氧氨基，硫代苯基，呋喃基，苯基C1-C6烷基，C1-C6卤代烷氧基，苯氧基，或C3-C6环烷基；且
Z是O或S。
CN92114622A 1991-11-22 1992-11-21 杀虫的苯基肼衍生物 Expired - Lifetime CN1033699C (zh)

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