Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing Imidogen

doi:10.6023/cjoc201611028

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 987-995.DOI: 10.6023/cjoc201611028 Previous Articles Next Articles

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含亚胺基(E)-β-Farnesene类似物的设计、合成及生物活性研究

张景朋^a, 秦耀果^a, 李欣潞^a, 宋敦伦^b, 刘俊杰^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:2016-11-22 修回日期:2016-12-18 发布日期:2016-12-21
通讯作者: 杨新玲 E-mail:yangxl@cau.edu.cn
基金资助:
国家自然科学基金重点（No.21132003）资助项目.

Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing Imidogen

Zhang Jingpeng^a, Qin Yaoguo^a, Li Xinlu^a, Song Dunlun^b, Liu Junjie^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:2016-11-22 Revised:2016-12-18 Published:2016-12-21
Contact: 10.6023/cjoc201611028 E-mail:yangxl@cau.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21132003).

1. Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing Imidogen.PDF(2564KB)

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 EBF analogues containing imidogen were designed by replacing unstable conjugated double bonds of EBF with different aromatic ring. Nineteen EBF analogues were synthesized via two reaction routes of N-alkylation and reductive amination. Their structures were confirmed by ¹H NMR, ¹³C NMR, IR and HRMS analysis. The bioassay and structure-activity relationship analysis were carried out. The result indicated that title compounds containing benzene or pyridine displayed obvious repellent activity against Myzus persicae (Sulzer). Especially, compounds 3g, 3l and 3m exhibited excellent repellent activity of 62.0%, 62.5% and 64.6% respectively. Moreover, the title compounds containing 1,3,4-thiadiazole ring showed certain insecticidal activity against M. persicae. In particular, the mortality rate of compounds 3i, 3l, 3r and 3s were 70.7%, 72.6%, 70.4% and 75.5% at a concentration of 200 μg/mL, which were higher than the lead EBF. However, compound 3a, in which the conjugated double bonds were replaced with butyl, showed obviously neither repellent nor aphicidal activity.

Key words: EBF analogues, imidogen, synthesis, repellent activity, insecticidal activity, structure-activity relationship

Cite this article

Zhang Jingpeng, Qin Yaoguo, Li Xinlu, Song Dunlun, Liu Junjie, Yang Xinling. Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing Imidogen[J]. Chin. J. Org. Chem., 2017, 37(4): 987-995.

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含亚胺基(E)-β-Farnesene类似物的设计、合成及生物活性研究

Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing Imidogen

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