Fungicidal Properties of 2-Amino-4-nitrophenol and Its Derivatives
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.
KeywordsFungicidal activity 2-Amino-4-nitrophenol N-(2-hydroxy-5-nitrophenyl)formamide N-(2-hydroxy-5-nitrophenyl)acetamide Aldehydes Ketones
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).
- Binetti R, Costamagna FM, Marcello I (2008) Exponential growth of new chemicals and evolution of information relevant to risk control. Ann Ist Super Sanità 44:13–15Google Scholar
- Commission of the European Communitites (1991) Commission directive 91/184/EEC of 12 March 1991. Off J Eur Commun L91:59–62Google Scholar
- Dinardo J, Draelos ZD (2007) An animal model assessment of common dye-induced allergic contact dermatitis. J Cosmet Sci 58(3):209–214Google Scholar
- IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans (1993) World Health Organization, International Agency for Research on Cancer, Geneva, (Multivolume work). http://monographs.iarc.fr/ENG/Classification/index.php, p V57 174
- Struck S, Schmidt U, Gruening B, Jaeger IS, Hossbach J, Preissner R (2008) Toxicity versus potency: elucidation of toxicity properties discriminating between toxins, drugs, and natural compounds. Genome Inform 20:231–242Google Scholar
- Bohnet W (2003) Ullmann’s encyclopedia of industrial chemistry, vol 1, 6th edn. Federal Republic of Germany, Wiley-VCH Verlag GmbH & Co, WeinheimGoogle Scholar