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Chemistry and Industry of Forest Products ›› 2017, Vol. 37 ›› Issue (5): 68-78.doi: 10.3969/j.issn.0253-2417.2017.05.009

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Synthesis and Antifungal Activity of Verbenone-based Oxime Sulfonate Compounds

ZHANG Rui1, DUAN Wengui1, LIN Guishan1, CHEN Zhicong1, HE Ran1, LEI Fuhou2   

  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:2017-03-13 Online:2017-10-25 Published:2017-10-30

Abstract: Verbenone was prepared by the selective oxidation of α-pinene at first. Then, twenty-two novel verbenone-based oxime sulfonate compounds(4a-4v)were synthesized by the oximation and O-sulfonylation reaction of the carbonyl group in verbenone. The target compounds were analyzed and characterized by FT-IR,1H NMR,13C NMR, and ESI-MS. Antifungal activity test showed that, at the mass concentration of 50 mg/L, the target compounds exhibited certain inhibition activity against the eight tested fungi. Inhibition rate of verbenone-based n-butyl oxime sulfonate(4u,R=(CH2)3CH3) against Rhizoctonia solani was 83.2%,inhibition rate of verbenone-based 2,4-difluorophenyl oxime sulfonate(4d,R=2,4-FPh) against Fusarium graminearum was 89.6% (better than the positive control chlorothalonil),and inhibition rate of verbenone-based p-nitrophenyl oxime sulfonate(4n,R=p-NO2Ph)and 4u(R=(CH2)3CH3) against Cercospora arachidicola was 72.5%。

Key words: α-pinene, verbenone, oxime sulfonate, synthesis, antifungal activity

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