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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (10): 1482-1491. 上一篇    下一篇

研究论文

含呋喃环双酰肼类衍生物的合成、杀虫活性及3D-QSAR研究

崔紫宁1，张莉1，黄娟1，凌云1，杨新玲*,1,2   

  1. (1中国农业大学理学院应用化学系 农业部农药化学与应用重点开放实验室 北京 100193)
    (2南开大学元素有机化学国家重点实验室 天津 300071)
  • 收稿日期:2010-01-04 修回日期:2010-03-18 发布日期:2010-05-06
  • 通讯作者: 杨新玲 E-mail:yangxl@cau.edu.cn

Synthesis, Insecticidal Activity and 3D-QSAR Studies on Diacylhy-drazine Derivatives Containing Furan

Cui Zining1 Zhang Li1 Huang Juan1 Ling Yun1 Yang Xinling*,1,2   

  1. (1 Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193)
    (2 State Key Laboratory of Elemento-organic Chemistry, Nankai Univer-sity, Tianjin 300071)
  • Received:2010-01-04 Revised:2010-03-18 Published:2010-05-06

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为发现新的昆虫生长调节剂, 经单取代苯基呋喃甲酰氯与取代苯甲酰肼反应得到22个未见文献报道的含呋喃环双酰肼类化合物, 其结构均通过了IR, 1H NMR和元素分析确认. 初步生测结果表明, 所有目标化合物对豆蚜(Aphis fabae)均有活性, 部分目标化合物表现出较好或中等的杀幼虫活性. 化合物Ia, Ib和Ic在药剂浓度为0.05%时, 对豆蚜的死亡抑制率分别为81.8%, 58.4%和52.2%, 其中化合物Ia对若蚜的蜕皮和成蚜产雌能力具有一定的抑制作用. 而大部分目标化合物在药剂浓度为0.1%, 0.05%和0.001%时, 对3龄粘虫(Mythimna separate)、棉红蜘蛛(Tetranchus urticae)和尖音淡色库蚊(Culex pipiens pallens)幼虫杀虫活性不明显. 采用比较分子力场分析(CoMFA)方法, 对22个化合物的杀蚜虫活性进行三维定量构效关系(3D-QSAR)研究. 在CoMFA研究中, 考察了不同力场和电荷下网格点步长对统计结果的影响. 建立了三维定量构效关系CoMFA模型(q2＝0.518, r2＝0.936). CoMFA模型的立体场、静电场三维等值线图不仅直观地解释了结构与活性的关系, 而且为后续优化该系列化合物提供了理论依据.

关键词: 昆虫生长调节剂, 双酰肼化合物, 呋喃, 三维定量构效关系, 比较分子立场分析

22 novel diacylhydrazine derivatives containing furan were synthesized by the reaction of 5-substituted phenyl-2-furoyl chloride with substituted benzohydrazide in anhydrous dichloromethane under reflux. Their structures were confirmed by IR, 1H NMR spectra and elemental analysis. The preliminary bioassay showed all the title compounds exhibited larvicidal activity to the Aphis fabae. At the concentration of 0.05%, compounds Ia, Ib and Ic showed 81.8%, 58.4% and 52.2% larvicidal activity to Aphis fabae respectively. The compound Ia could induce aphid larvae premature, abnormal, and lethal larval molt and poorer fecundity of adults. Most of the title compounds showed low activity to Mythimna separate, Tetranychus urticae and Culex pipiens pallens at the concentration of 0.1%, 0.05% and 0.001%. Comparative molecular field analysis (CoMFA) method was applied to the study on the three-dimensional quantitative structure activity relationship (3D-QSAR) of target compounds. Influence of the different grids on different force field with different kinds of charge form was evaluated and finally a reasonable model with predictive ability was obtained from the investigation (q2＝0.518, r2＝0.936). The con-tour maps based on the analysis of steric and electrostatic CoMFA coefficients could not only explain the re-lationship between the structures and bioactivity, but also lead to the insight into the further design of highly active compounds.

Key words: insect growth regulator, diacylhydrazine, furan, 3D-QSAR, comparative molecular field analysis (CoMFA)