Synthesis, insecticidal activities and DFT study of pyrimidin-4-amine derivatives containing the 1,2,4-oxadiazole motif

Abstract

Twenty six novel pyrimidin-4-amine derivatives containing the 1,2,4-oxadiazole motif were synthesized. Their chemical structures were confirmed by ¹H nuclear magnetic resonance (NMR), ¹³C NMR, and high-resolution mass spectrography. The insecticidal activity results indicated that some of them possessed excellent insecticidal activity (100%) against Mythimna separate, especially for compounds 6d, 6f, 6o, 6w, 6y and 6z. These compounds exhibited no activity against the insects Aphis medicagini and Tetranychus cinnabarinus. The structure- insecticidal activity relationships are discussed. Density functional theory analysis can potentially be used to design more active compounds. These results provide useful insecticide design information for further optimization.

Graphical abstract

Keywords

synthesis / pyrimidin-4-amine derivatives / 1,2,4-oxadiazole / insecticidal activity / structure-activity relationship

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Acknowledgements

This work was funded by the Zhejiang Provincial Natural Science Foundation of China (Grant No. LY19C140002), the Company of Three Win (Grant No. KYY-HX-20200746), Research Fund of Department of Education of Zhejiang Province (Grant No. Y202043162). We thank Dong-Song Hu for evaluating insecticidal activity.

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2021 Higher Education Press