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. 2020 Aug;76(8):2711-2719.
doi: 10.1002/ps.5817. Epub 2020 Mar 24.

Semi-synthesis and characterization of some new matrine derivatives as insecticidal agents

Xingan Cheng  1   2 , Huiqing He  1 , Wen-Xiong Wang  3 , Fangyun Dong  1 , Hanhui Zhang  1 , Jingmin Ye  1 , Chuncan Tan  1 , Yuehua Wu  1 , Xiaojing Lv  1 , Xuhong Jiang  1 , Xiangjing Qin  4
Affiliations

Semi-synthesis and characterization of some new matrine derivatives as insecticidal agents

Xingan Cheng et al. Pest Manag Sci. 2020 Aug.

Abstract

Background: Matrine is an important traditional plant-derived insecticide with broad-spectrum activity. However, due to its moderate activity, matrine is mainly applied in combination with other pesticides. In order to discover new potential natural-product-based crop protection agents, a series of matrine derivatives characterized by cyclohexylamine group were synthesized to screen their insecticidal activity against seven typically agricultural pests.

Results: The structural configurations of compounds were characterized by IR, 1 H NMR, 13 C NMR, MS and XRD, with the pure yields of 42%, 65% and 71%, respectively. Although all compounds showed poor insecticidal activity against five lepidoptera pests, the compounds 2 and 4 displayed remarkable insecticidal activities against Lipaphis erysimi and Mulberry Root-Knot Nematode with a concentration-dependent manner within 0.5~1.5 mg/ mL. Compared with matrine (60%), compounds 2 and 4 exhibited potent insecticidal activities against L. erysimi, with a corrected mortality of 83.3% and 89.7%, respectively. They also showed excellent control effects on Mulberry Root-Knot Nematode, with corrected mortality as high as 88% and 80%, respectively.

Conclusion: All four synthesized matrine derivatives showed poor insecticidal activity against five lepidoptera pests, but the compounds 2 and 4 exhibited much stronger insecticidal activities against L. erysimi and Mulberry Root-Knot Nematode than matrine. Combined with the structural characteristics of compounds 1~4, we conclude that 4-methylcyclohexylamine, not the carbon disulfide group or cyclohexylamine group alone, mainly contributed to the improvement of insecticidal activities of matrine derivatives against these two agricultural pests. This work provides a direction and foundation for structural optimization of the matrine pesticides in the future. © 2020 Society of Chemical Industry.

Keywords: insecticidal activity; matrine derivative; structural characterization; structural modification.

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References

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