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

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.

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Acknowledgements

The study was partly supported by Russian Foundation for Basic Research. Grant No. is 18-04-00274. The authors thank the Resource Center “Magnetic Resonance Methods of Research” of the St. Petersburg State University and the State Collection of Plant Pathogenic Microorganisms, Indicator Plants and Differential Cultivars of the All-Russian Research Institute of Phytopathology (Bolshie Vyazemy, Russia).

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Correspondence to Leonid Perelomov.

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Mukhtorov, L., Pestsov, G., Nikishina, M. et al. Fungicidal Properties of 2-Amino-4-nitrophenol and Its Derivatives. Bull Environ Contam Toxicol 102, 880–886 (2019). https://doi.org/10.1007/s00128-019-02602-4

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Keywords

  • Fungicidal activity
  • 2-Amino-4-nitrophenol
  • N-(2-hydroxy-5-nitrophenyl)formamide
  • N-(2-hydroxy-5-nitrophenyl)acetamide
  • Aldehydes
  • Ketones