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2015 , Vol. 35 >Issue 2: 455 - 461

DOI: https://doi.org/10.6023/cjoc201408002

研究简报

不同杂环取代(E)-β-Farnesene类似物的合成及生物活性研究

  • 秦耀果 ,
  • 曲焱焱 ,
  • 张景朋 ,
  • 谭晓庆 ,
  • 宋丽芳 ,
  • 李文浩 ,
  • 宋敦伦 ,
  • 杨新玲
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  • a 中国农业大学理学院应用化学系 北京 100193;
    b 中国农业大学农学与生物技术学院昆虫学系 北京 100193

收稿日期: 2014-08-01

  修回日期: 2014-10-27

  网络出版日期: 2014-11-20

基金资助

国家自然科学基金(No. 21132003)、国家重点基础研究发展规划(973计划, No. 2010CB126104)资助项目.

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Synthesis and Biological Activity of Different Heterocyclic Substituted (E)-β-Farnesene Analogues

  • Qin Yaoguo ,
  • Qu Yanyan ,
  • Zhang Jingpeng ,
  • Tan Xiaoqing ,
  • Song Lifang ,
  • Li Wenhao ,
  • Song Dunlun ,
  • Yang Xinling
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  • a Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193;
    b Department of Entomology, College of Agriculture and Biotechnology, China Agricultural University, Beijing 100193

Received date: 2014-08-01

  Revised date: 2014-10-27

  Online published: 2014-11-20

Supported by

Projects supported by the National Natural Science Foundation of China (No. 21132003) and the National Program on Key Basic Research Project (973 Program, No. 2010CB126104).

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摘要

为了寻求新型蚜虫控制剂, 以蚜虫报警信息素(E)-β-farnesene (EBF)为先导, 引入不同类型的杂环取代EBF结构中不稳定的共轭双键, 设计合成了一系列不同杂环取代的EBF类似物. 所有化合物结构均通过1H NMR、13C NMR、IR及HRMS确证. 对化合物进行了生物活性测试及初步构效关系分析. 结果表明, 所有化合物均对桃蚜和大豆蚜表现出一定的生物活性, 部分化合物的杀虫活性优于先导EBF, 酯基的引入则对驱避活性有利.

关键词： EBF类似物; 杂环; 杀虫活性; 驱避活性; 构效关系

本文引用格式

秦耀果 , 曲焱焱 , 张景朋 , 谭晓庆 , 宋丽芳 , 李文浩 , 宋敦伦 , 杨新玲 . 不同杂环取代(E)-β-Farnesene类似物的合成及生物活性研究[J]. 有机化学, 2015 , 35(2) : 455 -461 . DOI: 10.6023/cjoc201408002

Abstract

In order to discover novel aphid control agent, aphid alarm pheromone (E)-β-farnesene (EBF) was chosen as lead compound and a series of substituted EBF analogues were designed by replacing unstable conjugated double bond of EBF with different kinds of heterocyclic rings. All the compounds were synthesized and their structures were confirmed by 1H NMR, 13C NMR, IR spectra and HRMS analysis. Biological test showed that all the compounds displayed insecticidal or repellency activity to Myzuspersicae (Sulzer) or Aphis glycines (Matsumura). Some of them exhibited higher insecticidal activity than EBF. Introducing ester group was favorable to repellent activity.

Key words： EBF analogues; heterocyclic rings; insecticidal activity; repellency activity; structure-activity relationship

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