Synthesis and Pesticidal Activities of New Quinoxalines

Journal of Agricultural and Food Chemistry
Xing-Hai LiuStephen O Duke

Abstract

Natural products are a source of many novel compounds with biological activity for the discovery of new pesticides and pharmaceuticals. Quinoxaline is a fused N-heterocycle in many natural products and synthetic compounds, and seven novel quinoxaline derivatives were designed and synthesized via three steps. Pesticidal activities of title quinoxaline derivatives were bioassayed. Most of these compounds had herbicidal, fungicidal, and insecticidal activities. The compounds 2-(6-methoxy-2-oxo-3-phenylquinoxalin-1(2H)-yl)acetonitrile (3f) and 1-allyl-6-methoxy-3-phenylquinoxalin-2(1H)-one (3g) were the most active herbicides and fungicides. Mode-of-action studies indicated that 3f is a protoprophyrinogen oxidase-inhibiting herbicide. Compound 3f also possessed broad-spectrum fungicidal activity against the plant pathogen Colletotrichum species. Some of these compounds also had insecticidal activity. Molecular docking and DFT analysis can potentially be used to design more active compounds.

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Citations

Aug 6, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sen YangCheng-Xia Tan
Dec 17, 2020·Plants·Stephen O DukeJoanna Bajsa-Hirschel
Mar 7, 2021·International Journal of Molecular Sciences·Sen YangCheng-Xia Tan
Jan 29, 2022·Journal of Enzyme Inhibition and Medicinal Chemistry·Junfeng ShangBaolei Wang

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