Construction of spiro-1,2,4-oxadiazoline-fused matrine-type alkaloids as pesticidal agents

doi:10.1016/j.bmcl.2021.128356

Bioorganic & Medicinal Chemistry Letters

Volume 51, 1 November 2021, 128356

https://doi.org/10.1016/j.bmcl.2021.128356 Get rights and content

Abstract

In order to increase the agricultural properties of matrine, a series of novel matrine-type alkaloids containing spiro-1,2,4-oxadiazoline fragment at the C-15 position were prepared. Eight target molecules were elucidated by X-ray single-crystal diffraction. The antifeedant activities of Ig and IIIh against Mythimna separata Walker were>1.7 folds of the precursor matrine. The acaricidal activities of Ij, IIe, IIg, IIi and IIIa against Tetranychus cinnabarinus Boisduval were 2.6–3.7 folds of matrine. Especially IIg (R¹ = R² = 4-Cl) and IIi (R¹ = 4-Cl; R² = 4-Br) exhibited the pronounced antifeedant and acaricidal activities. SARs showed that their pesticidal activities were related to the substitutents and their positions on the phenyl rings at the C-3 and N-4 positions of 1,2,4-oxadiazoline skeleton.

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Declaration of Competing Interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgement

The work was supported by National Natural Science Foundation of China (No. 21877090, and 31672071).

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Construction of spiro-1,2,4-oxadiazoline-fused matrine-type alkaloids as pesticidal agents

Abstract

Graphical abstract

Section snippets

Declaration of Competing Interest

Acknowledgement

Insect Biochem Mol Biol

J Integr Agric

Bioorg Med Chem Lett

Eur J Med Chem

Bioorg Med Chem Lett

Ind Crop Prod

Bioorg Med Chem Lett

Bioorg Med Chem Lett

Toxins.

J Agric Food Chem

Biol Rev

Science