Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing 1,2,3-Thiadiazole

doi:10.6023/cjoc202005075

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2971-2979.DOI: 10.6023/cjoc202005075 Previous Articles Next Articles

含1,2,3-噻二唑环(E)-β-farnesene类似物的设计、合成及生物活性研究

张景朋^a,b, 杨朝凯^a, 秦耀果^a, 杨新玲^a

a 中国农业大学理学院应用化学系北京 100193;
b 中国林业科学研究院木材工业研究所北京 100091

收稿日期:2020-05-28 修回日期:2020-06-12 发布日期:2020-07-01
通讯作者: 杨新玲 E-mail:yangxl@cau.edu.cn
基金资助:
国家重点研发计划基金（No.2017YFD0200504）资助项目.

Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing 1,2,3-Thiadiazole

Zhang Jingpeng^a,b, Yang Zhaokai^a, Qin Yaoguo^a, Yang Xinling^a

a Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193;
b Research Institute of Wood Industry, Chinese Academy of Forestry, Beijing 100091

Received:2020-05-28 Revised:2020-06-12 Published:2020-07-01
Supported by:
Project supported by the National Key Research and Development Plan (No. 2017YFD0200504).

1. cjoc202005075辅助材料.pdf(3360KB)

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 15 EBF analogues were designed and synthesized by replacing unstable conjugated double bond of EBF with 1,2,3-thiadiazole. Their structures were confirmed by ¹H NMR, ¹³C NMR, IR and HRMS analysis. Repellent activity results indicated that analogues displayed better repellent activity against Myzus persicae (Sulzer). Among which compounds N-((E)-3,7-dimethyl-2,6-octadien-1-yl)-N-(2-naphthyl)-4-methyl-1,2,3-thiadiazole-5-carboxamide (8d), N-((E)-3,7-dimethyl-2,6-octadien-1-yl)-N-(4-methyl-pyridine-2-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide (8l) and N-((E)-3,7-dimethyl-2,6-octadien-1-yl)-N-(5-methyl-pyridine-2-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide (8m) exhibited excellent repellent activity of 63.1%, 61.3% and 63.4% respectively. The aphicidal bioassay results showed that most analogues exhibited considerable aphicidal activity against Myzus persicae. Especially, analogues N-((E)-3,7-dimethyl-2,6-octadien-1-yl)-N-(4-CN-phenyl)-4-methyl-1,2,3-thiadiazole-5-carboxamide (8b), N-((E)-3,7-dimethyl-2,6-octadien-1-yl)-N-(6-methyl-pyridine-2-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide (8g), N-((E)-3,7-dimethyl-2,6-octadien-1-yl)-N-(2-pyridyl)-4-methyl-1,2,3-thiadiazole-5-carboxamide (8j), N-((E)-3,7-dimethyl-2,6-octadien-1-yl)-N-(3-methyl-pyridine-2-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide (8k), 8l, 8m and N-((E)-3,7-dimethyl-2,6-octadien-1-yl)-N-(5-methyl-1,3,4-thiadiazole-2-yl)-4-methyl-1,2,3-thiadiazole-5-carboxamide (8o) exhibited high activity with LC₅₀ values of 10.2, 9.0, 25.1, 31.7, 8.4, 12.8 and 9.6 μg/mL, respectively, which were higher than the lead compound (E)-β-farnesene, but lower than commercial insecticide pymetrozine with LC₅₀ of 7.1 μg/mL.

Key words: 1,2,3-thiadiazole, EBF analogues, synthesis, repellent activity, insecticidal activity

Cite this article

Zhang Jingpeng, Yang Zhaokai, Qin Yaoguo, Yang Xinling. Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing 1,2,3-Thiadiazole[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2971-2979.

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含1,2,3-噻二唑环(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 1,2,3-Thiadiazole

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