Synthesis and antifungal activity of new salicylic acid derivatives

Author:

Wodnicka Alicja1,Huzar Elżbieta1,Krawczyk Maria2,Kwiecień Halina1

Affiliation:

1. West Pomeranian University of Technology, Szczecin, Faculty of Chemical Technology and Engineering, Institute of Organic Chemical Technology, al. Piastów 42, 71-065 , Szczecin , Poland

2. Institute of Industrial Organic Chemistry, Annopol 6, 03-236 , Warszawa , Poland

Abstract

Abstract A simple one-step procedure for synthesis of 1-methoxy-1-oxoalkan-2-yl salicylates and 1-methoxy-1-oxoalkan-2-yl 2-[(1-methoxy-1-oxoalkan-2-yl)oxy]benzoates by reaction of salicylic acid with several methyl 2-bromoalkanoates was developed. The reactions were carried out in N,N-dimethylformamide (DMF) in the presence of anhydrous potassium carbonate. Conditions for regioselective synthesis of target compounds were established. The developed procedure could be easily applied in the industrial production process. The new salicylic acid derivatives were obtained with satisfactory yields and were characterized by MS and 1H NMR spectra. The fungicidal activity of the prepared compounds was tested in vitro against seven species of plant pathogenic fungi. The best results were observed for 1-methoxy-1-oxoalkan-2-yl salicylates which showed moderate or good activity against Botrytis cinerea and Rhizoctonia solani.

Publisher

Walter de Gruyter GmbH

Subject

General Chemical Engineering,General Chemistry,Biotechnology

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