Discovery of N-Aryl-pyridine-4-ones as Novel Potential Agrochemical Fungicides and Bactericides

J Agric Food Chem. 2019 Dec 18;67(50):13904-13913. doi: 10.1021/acs.jafc.9b06296. Epub 2019 Dec 5.

Abstract

A series of N-aryl-pyridine-4-one derivatives were designed and synthesized using maltol and antidesmone as lead compounds, and then their fungicidal/bactericidal activities and possible mechanism of action against Colletotrichum musae were explored. Most of these compounds exhibited significant fungicidal activity in vitro. Especially, compound 23 has more than 90% inhibitory activity against nine plant pathogenic fungi at 50 μg mL-1, which is superior to azoxystrobin. Moreover, an in vivo bioassay also demonstrated that compound 23 exhibited high-efficiency broad-spectrum antifungal activity and can effectively control postharvest diseases of mango. In addition, it was found that compounds 22 and 23 can also effectively control rice bacterial leaf blight in pot experiments, which was even more effective than zhongshengmycin. Preliminary mechanism studies revealed that compound 23 may cause cell membrane and mitochondria destruction. These findings indicate that compound 23 can be used to develop potential agrochemical fungicides and bactericides.

Keywords: N-aryl-pyridine-4-ones; action mechanism; bactericidal activity; fungicidal activity; maltol; postharvest diseases.

MeSH terms

  • Agrochemicals / chemical synthesis
  • Agrochemicals / chemistry*
  • Agrochemicals / pharmacology*
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Colletotrichum / drug effects
  • Fungicides, Industrial / chemical synthesis
  • Fungicides, Industrial / chemistry*
  • Fungicides, Industrial / pharmacology*
  • Mangifera / microbiology
  • Molecular Structure
  • Oryza / microbiology
  • Plant Diseases / microbiology
  • Pyridines / chemistry
  • Pyridines / pharmacology
  • Rhizoctonia
  • Structure-Activity Relationship
  • Xanthomonas / drug effects
  • Xanthomonas / growth & development

Substances

  • Agrochemicals
  • Anti-Bacterial Agents
  • Fungicides, Industrial
  • Pyridines
  • pyridine

Supplementary concepts

  • Xanthomonas oryzae