Design, Synthesis, Crystal Structure, and Fungicidal Activity of L-Carvone Derivatives Containing an Oxime Ester Moiety

文献类型： 外文期刊

第一作者： Jin Can

作者： Jin Can;Zhou Xiaomao;Deng Xile;Zhou Yong;Zhou Xiaomao

作者机构：

关键词： nature product; L-carvone; synthesis; fungicidal activity

期刊名称：CHINESE JOURNAL OF ORGANIC CHEMISTRY （ 影响因子：1.652； 五年影响因子：1.2 ）

ISSN： 0253-2786

年卷期： 2021 年 41 卷 5 期

页码：

收录情况： SCI

摘要： L-Carvone is a natural product with fungicidal activity, which can be used as a lead compound for screening new fungicides. A series of L-carvone derivatives containing an oxime ester moiety were synthesized by splicing active substructure strategy with L-carvone as the lead compound. The structures of the L-carvone derivatives were characterized by IR, H-1 NMR, C-13 NMR and HRMS analyses. The antifungal activities of these compounds were evaluated against five plant pathogenic fungi, namely Sclerotinia sclerotiorum, Fusarium graminearum, Pyricularia grisea, Fusariwn oxysporum and Thanatephorus cucumeris. The results indicated that most of the compounds showed good antifungal activities. Among them, (E)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one O-(4-ethylbenzoyl)oxime (4e) had the best fungicidal activity against Fusarium graminearum (EC50=5.07 mg/L), and (S,E)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-one O-(3-methylbenzoyl)oxime (4b) had the best fungicidal activity against Sclerotinia sclerotiorum, (EC50=18.84 mg/L), which were better than the commercial fungicide enestroburin. Therefore, L-carvone derivatives have the potential to develop new fungicides.

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