Design, synthesis and antifungal evaluation of low bee-toxicity coumarin oxime derivatives

文献类型： 外文期刊

第一作者： Yuan, Hanxiao

作者： Yuan, Hanxiao;Liu, Yining;Zhang, Xinru;Zhang, Wenguang;Feng, Juntao;Gao, Yanqing;Liu, Xili;Ma, Zhiqing;Wang, Yong;Lei, Peng;Qu, Yanyan;Xie, Renzhuang;Xu, Xilian;Xie, Renzhuang;Feng, Juntao;Gao, Yanqing;Ma, Zhiqing;Wang, Yong;Lei, Peng;Liu, Xili;Lei, Peng

作者机构：

关键词： coumarin; green pesticide; low toxicity; natural product; rice sheath blight

期刊名称：PEST MANAGEMENT SCIENCE （ 影响因子：3.8； 五年影响因子：4.3 ）

ISSN： 1526-498X

年卷期： 2025 年 81 卷 9 期

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收录情况： SCI

摘要： BACKGROUNDStructural modification of natural products is one of the most effective approaches for discovering new agrochemical compounds. Coumarin, a natural product, is widely found in higher plants from the Brassicaceae, Umbelliferae, Leguminosae, and Orchidaceae families. Coumarin and its derivatives exhibit a wide range of biological activities. Based on our previous research, a series of novel coumarin oxime derivatives were designed and synthesized. The preliminary mechanism of action and bee toxicity of the highly active compound were also investigated.RESULTSMost of the target compounds exhibited good antifungal activities. Compound 5k demonstrated moderate to strong broad-spectrum antifungal activities against all seven tested pathogenic fungi. Notably, it showed satisfactory antifungal activity against Rhizoctonia solani (median effective concentration = 3.29 mu g/mL), surpassing the performance of the commercial coumarin fungicide osthole. In addition, the protective and curative effects of compound 5k against rice sheath blight at 200 mu g/mL were 82.1% and 91.4% on detached rice leaves, and 82.5% and 72.5% on potted rice plants, respectively, outperforming osthole. Preliminary mechanistic studies suggested that compound 5k could alter mycelial morphology and increase catalase activity, promoting antioxidant and free radical scavenging functions to activate the plant's defense system. Furthermore, the median lethal dose of compound 5k was found to exceed 200 mu g/bee based on an acute contact toxicity test conducted on honeybees.CONCLUSIONThis study demonstrates that coumarin oxime derivatives, with their novel structures, simple synthesis, excellent activity, and low bee toxicity, have the potential to become practical fungicides for plant protection, offering broad application prospects. (c) 2025 Society of Chemical Industry.

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