Novel Cinnamic Acid Derivatives Containing the 1,3,4-Oxadiazole Moiety: Design, Synthesis, Antibacterial Activities, and Mechanisms

  • J Agric Food Chem. 2021 Oct 13;69(40):11804-11815. doi: 10.1021/acs.jafc.1c03087.
Shaobo Wang  1 ,  Jixiang Chen  1 ,  Jing Shi  1 ,  Zhijia Wang  1 ,  Deyu Hu  1 ,  Baoan Song  1
Affiliations
  • 1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang550025, China.
PMID: 34597041 DOI: 10.1021/acs.jafc.1c03087
Abstract

There is a lack of effective Antibacterial agents against rice Bacterial leaf streak and leaf blight. Cinnamic acid derivatives containing the 1,3,4-oxadiazole moiety were synthesized, and their Antibacterial activities against Xanthomonas oryzae pv. oryzicola (Xoc) and X. oryzae pv. oryzae (Xoo) were evaluated. Based on the three-dimensional quantitative structure-activity relationship (3D-QSAR) model, compound 31 with better Antibacterial activity against Xoc was designed and synthesized, and the 50% effective concentration (EC50) value was 0.2 mg/L. The curative and protective activities of compound 31 against rice Bacterial leaf streak at 100 mg/L were 39.5 and 35.4%, respectively, which were higher than those of thiodiazole copper (28.4 and 20.7%, respectively). The Antibacterial activity of compound 31 against rice Bacterial leaf streak is closely associated with the activity of related defensive Enzymes and the increase in glutathione metabolism.

Keywords
1,3,4-oxadiazole; 3D-QSAR; Xanthomonas oryzae pv. oryzae; Xanthomonas oryzae pv. oryzicola; antibacterial activity; cinnamic acid; mechanisms of action.
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