The Efficacy and Underlying Mechanism of Sulfone Derivatives Containing 1,3,4-oxadiazole on Citrus Canker

Molecules. 2015 Aug 4;20(8):14103-17. doi: 10.3390/molecules200814103.

Abstract

The objectives of the current study were to isolate and identify the pathogen responsible for citrus canker and investigate the efficacy of sulfone derivatives containing 1,3,4-oxadiazole moiety on controlling citrus canker caused by Xanthomonas citri subsp. citri (Xcc) under in vitro and field conditions. In an in vitro study, we tested eight sulfone derivatives against Xcc and the results demonstrated that compound 3 exhibited the best antibacterial activity against Xcc, with a half-maximal effective concentration (EC50) value of 1.23 μg/mL, which was even better than those of commercial bactericides Kocide 3000 (58.21 μg/mL) and Thiodiazole copper (77.04 μg/mL), respectively. Meanwhile, under field experiments, compound 3 treatments demonstrated the highest ability to reduce the disease of citrus canker in leaves and fruits in two different places relative to an untreated control as well as the commercial bactericides Kocide 3000 and Thiodiazole copper. Meanwhile, compound 3 could stimulate the increase in peroxidase (POD), polyphenol oxidase (PPO), and phenylalanine ammonia lyase (PAL) activities in the navel orange leaves, causing marked enhancement of plant resistance against citrus canker. Moreover, compound 3 could damage the cell membranes, destruct the biofilm formation, inhibit the production of extracellular polysaccharide (EPS), and affect the cell membrane permeability to restrain the growth of the bacteria.

Keywords: Xanthomonas citri subsp. citri; antibacterial bioassay; citrus canker; sulfone derivatives; underlying mechanism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biofilms / drug effects
  • Biofilms / growth & development
  • Catechol Oxidase / metabolism
  • Cell Membrane / drug effects
  • Cell Membrane / metabolism
  • Cell Membrane Permeability / drug effects
  • Citrus / microbiology*
  • Electric Conductivity
  • Microbial Sensitivity Tests
  • Oryza / drug effects
  • Oryza / microbiology
  • Oxadiazoles / pharmacology*
  • Peroxidase / metabolism
  • Phenylalanine Ammonia-Lyase / metabolism
  • Plant Diseases / microbiology*
  • Polymerase Chain Reaction
  • Polysaccharides / analysis
  • Reference Standards
  • Sulfones / pharmacology*
  • Xanthomonas / drug effects
  • Xanthomonas / physiology

Substances

  • Oxadiazoles
  • Polysaccharides
  • Sulfones
  • 1,3,4-oxadiazole
  • Catechol Oxidase
  • Peroxidase
  • Phenylalanine Ammonia-Lyase