Design, Synthesis and Repellent Activity of (E)-β-Farnesene Analogues Containing Benzene Ring with Different Substitutions

doi:10.6023/cjoc201603021

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (8): 1883-1889.DOI: 10.6023/cjoc201603021 Previous Articles Next Articles

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含苯环(E)-β-Farnesene类似物的设计、合成及驱避活性研究

张景朋^a, 秦耀果^a, 李文浩^a, 凌云^a, 杨立波^b, 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 中国农业大学植物保护学院昆虫学系北京 100193

收稿日期:2016-03-14 修回日期:2016-04-07 发布日期:2016-04-20
通讯作者: 杨新玲 E-mail:yangxl@cau.edu.cn
基金资助:
国家重点自然科学基金（No. 21132003）资助项目.

Design, Synthesis and Repellent Activity of (E)-β-Farnesene Analogues Containing Benzene Ring with Different Substitutions

Zhang Jingpeng^a, Qin Yaoguo^a, Li Wenhao^a, Ling Yun^a, Yang Libo^b, 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 Plant Protection, China Agricultural University, Beijing 100193

Received:2016-03-14 Revised:2016-04-07 Published:2016-04-20
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21132003).

1. Design, Synthesis and Repellent Activity of (E)-β-Farnesene Analogues Containing Benzene Ring with Different Substitutions.PDF(2769KB)

Abstract

In order to discover novel compounds with high-activity to control aphid, 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 substitutions benzene ring. An N-alkylation route was optimized by using aniline and (E)-1-chloro-3,7-dimethyl-2,6-octadiene. Nineteen EBF analogues were synthesized with yields of 39%～83% in this optimization reaction condition. Their structures were confirmed by ¹H NMR, ¹³C NMR and HRMS analysis. Bioassay showed that the title compounds demonstrated repellent activity against Myzus persicae (Sulzer). In particular, 4d, 4h and 4k exhibited excellent repellent activity of 56.3%, 58.3% and 50.3% respectively. The performed structure-activity relationship indicated that introduction of halogen group at the 4 position of phenyl ring displayed relatively higher activity.

Key words: EBF analogues, benzene ring, N-alkylation, repellent activity, structure-activity relationship

Cite this article

Zhang Jingpeng, Qin Yaoguo, Li Wenhao, Ling Yun, Yang Libo, Song Dunlun, Yang Xinling. Design, Synthesis and Repellent Activity of (E)-β-Farnesene Analogues Containing Benzene Ring with Different Substitutions[J]. Chin. J. Org. Chem., 2016, 36(8): 1883-1889.

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含苯环(E)-β-Farnesene类似物的设计、合成及驱避活性研究

Design, Synthesis and Repellent Activity of (E)-β-Farnesene Analogues Containing Benzene Ring with Different Substitutions

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