Abstract

Two series of novel fraxinellone-based thioethers containing 1,3,4-oxadiazole moiety were prepared as insecticidal agents against the oriental armyworm, Mythimna separata Walker. The structural assignment was based on the spectroscopic and X-ray analysis data. Among all the target compounds, compounds 4b, 4k, 5b, 5j and 5k exhibited more potent insecticidal activity with final mortality rates (FMRs) of more than 65%, especially 4k with the FMR of 75.9%, when compared with toosendanin. Some interesting results of structure–activity relationships are also discussed.

Highlights

  • The oriental armyworm (Mythimna separata Walker, Lepidoptera: Noctuidae), a typical long-distance migratory insect, is one of the most serious pests of cereal crops in countries including China, India, Australia and New Zealand [1,2]

  • Two series of novel fraxinellone-based thioethers containing 1,3,4-oxadiazole moiety were prepared as insecticidal agents against the oriental armyworm, Mythimna separata Walker

  • Among all the target compounds, compounds 4b, 4k, 5b, 5j and 5k exhibited more potent insecticidal activity with final mortality rates (FMRs) of more than 65%, especially 4k with the FMR of 75.9%, when compared with toosendanin

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Summary

Introduction

The oriental armyworm (Mythimna separata Walker, Lepidoptera: Noctuidae), a typical long-distance migratory insect, is one of the most serious pests of cereal crops in countries including China, India, Australia and New Zealand [1,2] Seasonal outbreaks of this pest can cause significant economic damage to cereal crops in China and other countries [3]. They have been extensively used to control insect pest outbreaks, the overuse and improper application of synthetic chemical pesticides over the years has resulted in enhancement of pest resistance, environmental problems and negative impacts on human health [5,6,7]. In a continuation of our programme aimed at the development of fraxinellone-based insecticidal agents, we prepared two series of novel fraxiellone-based thioethers containing 1,3,4-oxadiazole moiety (VI and VII, figure 1) as insecticidal agents against M. separata

Instrument and materials
Data for 1
General procedure for synthesis of compounds 2 and 3
Data for 2
Data for 3
General procedure for synthesis of compounds 4a–k and 5a–k
Data for 4a
Data for 4b
Data for 4c
Data for 4d
Data for 5a
Data for 5b
Data for 5c
Data for 5d
X-ray crystallography
Biological assay
Synthesis
Findings
Insecticidal activity
Conclusion

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