偏氯含氟菊酯异构体的合成及其杀虫活性有机化学.pdfVIP

2011 年第 31 卷 有 机 化 学 Vol. 31, 2011 第 10 期, 1624～1630 Chinese Journal of Organic Chemistry No. 10, 1624～1630 ·研究论文· 偏氯含氟菊酯异构体的合成及其杀虫活性 郑祖彪 李新军 王翠翠 邹新琢* (华东师范大学化学系 上海 200062) 摘要 α-氰基-4-氟-3-苯氧苄基-2,2-二甲基-3-(-2-氯乙烯基)-环丙烷羧酸酯(简称偏氯含氟菊酯)是一类新型拟除虫菊酯. 报道了它的 12 个异构体的合成. 生物活性测试结果表明, 这些异构体对淡色库蚊四龄孑孓都显示出杀虫活性, 其中 (αS,1R,3R)-cis-E-异构体 5aes 和(αS,1R,3R)-cis-Z-异构体 5azs 显示出比溴氰菊酯更高的杀虫活性. 关键词 偏氯含氟菊酯; 异构体; 合成; 拟除虫菊酯; 杀虫活性 Syntheses of the Isomers of α-Cyano-4-fluoro-3-phenoxybenzyl Ester of Monochlorinated Pyrethric Acid and Their Insecticidal Activity Zheng, Zubiao Li, Xinjun Wang, Cuicui Zou, Xinzhuo* (Department of Chemistry, East China Normal University, Shanghai 200062) Abstract α-Cyano-4-fluoro-3-phenoxybenzyl ester of monochlorinated pyrethric acid is a new kind of py- rethroids. Syntheses of the isomers of cis/trans-monochlorinated pyrethric acids and their esters were re- ported. The results of biological test indicated that these isomers of pyrethroids had insecticidal activities against Culex pipiens pallens (larvae). And some of the isomers, such as (αS,1R,3R)-cis-E-isomer 5aes and (αS,1R,3R)-cis-Z-isomer 5azs, exhibit higher insecticidal activities than deltamethrin. Keywords monochlorinated pyrethriod; isomer; synthesis; pyrethroid; insecticidal activity 随着全球人口和粮食的需求的增加; 气候的温暖化 定性型二卤代菊酯, 已表现出对人类和环境的潜在危害 使农作物的病虫害也随之增多; 以蚊虫为传染介质的疟 性, 被怀疑具有致畸、致突变性或环境激素作用[7,8]. 尽 疾和登革热等传染病的流行也有上升的趋势, 对人类健 管如此, 其高效低毒的特性使其暂时难以被其他品种轻 康构成了严重威胁[1,2]等因素使农药的需求增加[3]. 另一 易取代, 尤其是在卫生杀虫剂方面. 寻找新