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Chemistry and Industry of Forest Products ›› 2019, Vol. 39 ›› Issue (4): 27-34.doi: 10.3969/j.issn.0253-2417.2019.04.004

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Synthesis and Antifungal Activity of (Z)-/(E)-Verbenone Oxime Ether Compounds

Xiaoyu WANG1,Wengui DUAN1,*(),Guishan LIN1,Guoqiang KANG1,Minghao SHANG1,Fuhou LEI2   

  1. 1. College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China
    2. Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008, China
  • Received:2019-04-15 Online:2019-08-25 Published:2019-08-23
  • Contact: Wengui DUAN E-mail:wgduan@gxu.edu.cn
  • Supported by:


Verbenone was prepared by selective oxidation of α-pinene at first. Then, by oximation of the carbonyl group (Z)-and(E)-verbenone oxime compounds were synthesized and separaed, followed by the nucleophilic substitution reaction to afford forty novel (Z)-and (E)-verbenone oxime ether compounds 4a-4t, including twenty couples of Z/E isomers. The structures of the target compounds were characterized by 1H NMR, 13C NMR, FT-IR, UV-vis, and ESI-MS. The antifungal activities of the target compounds were evaluated. The results showed that, at the mass concentration of 50 mg/L, all the target products exhibited certain inhibition activities against the eight kinds of plant pathogens. Compound(E)-4r(R=2, 6-Cl) had inhibition rates of 77.8% against Physalospora piricola. Compound(E)-4s(R=2, 6-F) had inhibition rates of 72.7% against Rhizoctonia solani. Compound (E)-4n(R=p-CN) had inhibition rates of 70.8% against Helmithosporium maydis. Certain difference were found in inhibition activity of Z-E isomers against some plant pathogens. The CoMFA model(r2=0.992, q2=0.507) of (E)-verbenone oxime ether compounds for inhibiting Rhizoctonia solani was established for the study of 3D-QSAR, and the results could provide a basis for the design of potential lead compounds with higher activity.

Key words: α-pinene, verbenone, oxime ether, Z-E isomer, antifungal activity, 3D-QSAR

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