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Chemistry and Industry of Forest Products ›› 2016, Vol. 36 ›› Issue (1): 61-69.doi: 10.3969/j.issn.0253-2417.2016.01.009

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Synthesis and Antifungal Activities of 2-Sustituted Acylamino-5-(α-campholenic aldehyde)-based-1, 3, 4-thiadiazole Compounds

HUANG Duo-yun1, DUAN Wen-gui1, LIN Gui-shan1, BAI Xue1, XIAO Hao1, YANG Zhang-qi2   

  1. 1. College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China;
    2. Guangxi Academy of Forestry, Nanning 530002, China
  • Received:2014-12-15 Online:2016-02-25 Published:2016-03-18

Abstract: α-Campholenic aldehyde was prepared by the epoxidation and catalytic isomerization of α-pinene.Then, α-campholenic aldehyde-based thiadiazole was prepared by the cyclization reaction of α-campholenic aldehyde-based thiosemicarbazone, which was obtained by the reaction of thiosemicarbazide with α-campholenic aldehyde.Finally, twelve novel 2-sustituted acylamino-5-(α-campholenic aldehyde)-based-1, 3, 4-thiadiazole compounds (6a-6l) were synthesized by the N-acylation reactions of α-campholenic aldehyde-based thiadiazole with a series of acyl chlorides.The target compounds were characterized by FT-IR, 1H NMR, 13C NMR, and ESI-MS.Antifungal activity test showed that, at the concentration of 50 mg/L, the target compounds exhibited different antifungal activities against the five tested fungi.Some of them exhibited antifungal activities were close to or even better than the commercial azoxystrobin used as positive control in this study.Among them, in which compound 6j had an inhibition rate of 94.4% against Fusarium graminearum, and compound 6h had an inhibition rate of 97.7% against Physalospora piricola.

Key words: α-pinene, α-campholenic aldehyde, amide, 1, 3, 4-thiadiazole, synthesis, antifungal activity

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