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

doi:10.6023/cjoc201408002

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (2): 455-461.DOI: 10.6023/cjoc201408002 Previous Articles Next Articles

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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^a, 曲焱焱^b, 张景朋^a, 谭晓庆^a, 宋丽芳^b, 李文浩^a, 宋敦伦^b, 杨新玲^a

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 发布日期:2014-11-20
通讯作者: 宋敦伦, 杨新玲 E-mail:songdl@cau.edu.cn;yangxl@cau.edu.cn
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.

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

Qin Yaoguo^a, Qu Yanyan^b, Zhang Jingpeng^a, Tan Xiaoqing^a, Song Lifang^b, Li Wenhao^a, Song Dunlun^b, Yang Xinling^a

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:2014-08-01 Revised:2014-10-27 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).

1. Synthesis and Biological Activity of Different Heterocyclic Substituted (E)-β-Farnesene Analogues.PDF(11789KB)

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

Cite this article

Qin Yaoguo, Qu Yanyan, Zhang Jingpeng, Tan Xiaoqing, Song Lifang, Li Wenhao, Song Dunlun, Yang Xinling. Synthesis and Biological Activity of Different Heterocyclic Substituted (E)-β-Farnesene Analogues[J]. Chin. J. Org. Chem., 2015, 35(2): 455-461.

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不同杂环取代(E)-β-Farnesene类似物的合成及生物活性研究

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

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