Synthesis and Pesticidal Activities of New Quinoxalines.,Journal of Agricultural and Food Chemistry

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Synthesis and Pesticidal Activities of New Quinoxalines.
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2020-06-12 , DOI: 10.1021/acs.jafc.0c01042
Xing-Hai Liu ₁ , Wei Yu ₁ , Li-Jing Min ₂ , David E Wedge ₃ , Cheng-Xia Tan ₁ , Jian-Quan Weng ₁ , Hong-Ke Wu ₁ , Charles L Cantrell ₃ , Joanna Bajsa-Hirschel ₃ , Xue-Wen Hua ₄ , Stephen O Duke ₅

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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.

中文翻译：

新喹喔啉的合成和杀虫活性。

天然产物是许多具有生物活性的新型化合物的来源，可用于发现新的农药和药物。喹喔啉是许多天然产物和合成化合物中的稠合N-杂环，通过三个步骤设计并合成了七个新颖的喹喔啉衍生物。生物学分析了标题喹喔啉衍生物的杀虫活性。这些化合物大多数具有除草，杀真菌和杀虫活性。化合物2-（6-甲氧基-2-氧代-3-苯基喹喔啉-1（2 H）-基）乙腈（3f）和1-烯丙基-6-甲氧基-3-苯基喹喔啉-2（1 H）- 3g）是最活跃的除草剂和杀真菌剂。作用模式研究表明3f是抑制原卟啉原氧化酶的除草剂。化合物3f还具有针对植物病原体炭疽菌物种的广谱杀真菌活性。这些化合物中的一些还具有杀虫活性。分子对接和DFT分析可以潜在地用于设计更多活性化合物。

更新日期：2020-07-15

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