Fungicidal Properties of 2-Amino-4-nitrophenol and Its Derivatives

Bull Environ Contam Toxicol. 2019 Jun;102(6):880-886. doi: 10.1007/s00128-019-02602-4. Epub 2019 Mar 28.

Abstract

Fungicidal effect of 2-amino-4-nitrophenol and its derivates, prepared by replacing the hydrogen atom in its amino group by different organic radicals was studied. Evaluation of the biological activity of studied substances by сomputational chemistry methods was performed. Toxicity of 2-amino-4-nitrophenol and synthesized N-(2-hydroxy-5-nitrophenyl)formamide and N-(2-hydroxy-5-nitrophenyl)acetamide to six species of phytophatogen fungi were tested in the experiment. The results of the study demonstrate that replacement of the hydrogen atom in the amino group by a aldehyde group leads to an increase in fungicidal activity with respect to Rhizoctonia solani and Bipolaris sorokiniana. A replacement of the hydrogen atom by a ketone group increases the inhibitory effect on Sclerotinia sclerotiorum and Venturia inaequalis. The paper contains comparative data on the fungicide effect of commercial preparation for studied fungi also.

Keywords: 2-Amino-4-nitrophenol; Aldehydes; Fungicidal activity; Ketones; N-(2-hydroxy-5-nitrophenyl)acetamide; N-(2-hydroxy-5-nitrophenyl)formamide.

MeSH terms

  • Acetamides / chemistry
  • Acetamides / pharmacology
  • Ascomycota / drug effects*
  • Formamides / chemistry
  • Formamides / pharmacology
  • Fungicides, Industrial / chemistry
  • Fungicides, Industrial / pharmacology*
  • Ketones / chemistry
  • Ketones / pharmacology
  • Nitrophenols / chemistry
  • Nitrophenols / pharmacology*
  • Rhizoctonia / drug effects*
  • Structure-Activity Relationship

Substances

  • Acetamides
  • Formamides
  • Fungicides, Industrial
  • Ketones
  • Nitrophenols
  • 2-amino-4-nitrophenol