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Chemical Research in Chinese Universities

, Volume 33, Issue 5, pp 758–764 | Cite as

Design, synthesis and biological activities of novel 4,5-disubstituted-3-S-(β-D-acetylglycosyl)-1,2,4-triazole derivatives

  • Dandan Cheng
  • Wei Wei
  • Yuxin Li
  • Xuewen Hua
  • Yunyun Zhou
  • Jingbo Liu
  • Yonghong Li
  • Shujing Yu
  • Lixia Xiong
  • Zhengming Li
Article
  • 90 Downloads

Abstract

A series of novel 4,5-disubstituted-3-S-(β-D-acetylglycosyl)-1,2,4-triazole derivatives was designed and synthesized via the strategy of introducing S-β-D-acetylglycosyl fragments into 1,2,4-triazole ring. The structures of 17 target compounds were characterized by means of 1H NMR, 13C NMR and high-resolution mass spectrometer (HRMS). The results of insecticidal activity indicated that compound 5a displayed 60% lethality rate at 100 mg/L concentration. More importantly, the introduction of the carbohydrate fragment to the 1,2,4-triazole core could improve the insecticidal activities since the insecticidal activities of compounds 5 were better than those of compounds 4 and this result was also supported by calcium imaging technique. The antifungal activity of the target compounds showed that some novel compounds displayed moderate to good inhibition rate against Sclerotinia sclerotiorum and Botrytis cinerea, in which compound 5p exhibited 78.8% inhibition rate against Sclerotinia sclerotiorum and 68.6% inhibition rate against Botrytis cinerea. The herbicidal activities of compounds 5 against Brassica campestris indicated that most of the target compounds showed moderate to good activities, especially compound 5g which showed 52.9% herbicidal activity at the concentration of 200 mg/L.

Keywords

1,2,4-Triazole S-β-D-acetylglycosyl Biological activity 

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Copyright information

© Jilin University, The Editorial Department of Chemical Research in Chinese Universities and Springer-Verlag GmbH Germany 2017

Authors and Affiliations

  • Dandan Cheng
    • 1
  • Wei Wei
    • 1
  • Yuxin Li
    • 1
  • Xuewen Hua
    • 2
  • Yunyun Zhou
    • 3
  • Jingbo Liu
    • 1
  • Yonghong Li
    • 1
  • Shujing Yu
    • 1
  • Lixia Xiong
    • 1
  • Zhengming Li
    • 1
  1. 1.State Key Laboratory of Elemento-Organic Chemistry, Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering(Tianjin), College of ChemistryNankai UniversityTianjinP. R. China
  2. 2.College of AgricultureLiaocheng UniversityLiaochengP. R. China
  3. 3.State Key Laboratory of Molecular Engineering of Polymers, Department of Macromolecular ScienceFudan UniversityShanghaiP. R. China

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