Original scientific paper

https://doi.org/10.5562/cca3903

Novel Synthetic Routes to Quaternary Pyridinium Salts and their Antifungal Activity

Valentina Bušić ; Josip Juraj Strossmayer University of Osijek, Faculty of Food Technology Osijek, Kuhačeva 20, HR–31000 Osijek, Croatia
Karolina Vrandečić ; Faculty of Agrobiotechnical Sciences, Josip Juraj Strossmayer University of Osijek, Vladimira Preloga 1, HR–31000 Osijek, Croatia
Tamara Siber ; Faculty of Agrobiotechnical Sciences, Josip Juraj Strossmayer University of Osijek, Vladimira Preloga 1, HR–31000 Osijek, Croatia
Sunčica Roca ; NMR Centre, Ruđer Bošković Institute, Bijenička cesta 54, HR–10000 Zagreb, Croatia
Vice Tomičić ; Josip Juraj Strossmayer University of Osijek, Faculty of Food Technology Osijek, Kuhačeva 20, HR–31000 Osijek, Croatia
Dajana Gašo Sokač ; Josip Juraj Strossmayer University of Osijek, Faculty of Food Technology Osijek, Kuhačeva 20, HR–31000 Osijek, Croatia

Abstract

Eleven pyridine derivatives were prepared by quaternization reactions by different synthetic routes: conventional, microwave, and ultrasound. Since acetone and other solvents used in conventional quaternization reactions are harmful, attempts were made to replace the organic solvents with more environmentally friendly alternative - deep eutectic solvents. The reactions were carried out using pyridine-3-aldoxime, pyridine-4-aldoxime, isonicotinamide and nicotinamide as nucleophiles and three different dihaloalkanes as electrophiles: diiodopropane, dibromopropane and diiodohexane. The results showed that the microwave method using acetone as solvent was significantly faster and gave higher yields than the conventional method. In contrast, synthesis in the eutectic solvents choline chloride : urea gave significantly lower yields. The structures of the synthesized compounds were confirmed by 1H and 13C NMR spectroscopy, mass spectrometry and elemental analysis. The antifungal activity of all compounds was tested at two different concentrations (10 and 100 µg mL–1) against Botrytis cinerea, Fusarium culmorum, Macrophomina phaseolina and Sclerotinia sclerotiorum in vitro. All tested compounds showed excellent inhibitory activity against the studied phytopathogenic fungal species at a concentration of 100 µg mL–1.

Keywords

antifungal activity; dihaloalkanes; deep eutectic solvents; microwave synthesis; quaternization; pyridine derivatives; ultrasound synthesis

Hrčak ID:

286193

URI

https://hrcak.srce.hr/286193

Publication date:

23.11.2022.

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