Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (5): 2008-2018.DOI: 10.6023/cjoc202010028 Previous Articles     Next Articles

ARTICLES

含肟酯基L-香芹酮衍生物的设计、合成、晶体结构及杀菌活性

金灿a, 邓希乐b, 周勇b, 周小毛a,b,*()   

  1. a 湖南大学研究生院隆平分院 长沙 410125
    b 湖南省农业科学院 湖南省农业生物技术研究所 长沙 410125
  • 收稿日期:2020-10-21 修回日期:2020-12-11 发布日期:2021-02-22
  • 通讯作者: 周小毛
  • 基金资助:
    国家自然科学基金(31672056)

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

Can Jina, Xile Dengb, Yong Zhoub, Xiaomao Zhoua,b,*()   

  1. a Long Ping Branch, Graduate School of Hunan University, Changsha 410125
    b Hunan Agricultural Biotechnology Research Institute, Hunan Academy of Agricultural Sciences, Changsha 410125
  • Received:2020-10-21 Revised:2020-12-11 Published:2021-02-22
  • Contact: Xiaomao Zhou
  • About author:
    * Corresponding author. E-mail:
  • Supported by:
    National Natural Science Foundation of China(31672056)

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, 1H NMR, 13C 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.

Key words: nature product, L-carvone, synthesis, fungicidal activity