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Chemistry and Industry of Forest Products ›› 2017, Vol. 37 ›› Issue (1): 54-62.doi: 10.3969/j.issn.0253-2417.2017.01.007

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Synthesis and Biological Activities of Perillaldehyde-based Schiff Base-(thio) urea Compounds

MA Yuan1, DUAN Wengui1, LIN Guishan1, LIU Luzhi1, HUANG Zhengsong1, 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:2016-04-05 Online:2017-02-25 Published:2017-02-25

Abstract: Thirteen novel perillaldehyde-based Schiff base-(thio)urea compounds (5a-5m) were designed and synthesized by using perillaldehyde as starting material. Their structures were analyzed and characterized by FT-IR, 1H NMR, 13C NMR, and ESI-MS. The results of preliminary bioassay showed that, at the mass concentration of 50 mg/L, the inhibition rate of target compound 5f (R=p-FAr) against Physalospora piricola was 90.0% (close to that of the positive control azoxystrobin), and the inhibition rate of target compound 5d (R=Ar) against Alternaria solani was 91.8% (close to that of the positive control azoxystrobin). Besides, at the mass concentration of 100 mg/L, the target compounds 5c (R=cyclopentyl), 5i (R=p-CH3Ar) and 5a (R=CH3) exhibited 77.6%, 75.3% and 67.4% inhibition against the growth of rape (Brassica campestris) root, respectively (greater than positive control flumioxazin). Furthermore, substituted phenyl thioureas showed better antifungal and herbicidal activities than substituted phenyl ureas.

Key words: perillaldehyde, Schiff base-(thio)urea, synthesis, antifungal activity, herbicidal activity

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