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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 9: 2971 - 2979

DOI: https://doi.org/10.6023/cjoc202005075

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

  • Zhang Jingpeng ,
  • Yang Zhaokai ,
  • Qin Yaoguo ,
  • Yang Xinling
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  • 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 date: 2020-05-28

  Revised date: 2020-06-12

  Online published: 2020-07-01

Supported by

Project supported by the National Key Research and Development Plan (No. 2017YFD0200504).

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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 . DOI: 10.6023/cjoc202005075

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