Novel Synthetic Routes to Quaternary Pyridinium Salts and their Antifungal Activity

Bušić, Valentina; Vrandečić, Karolina; Siber, Tamara; Roca, Sunčica; Tomičić, Vice; Gašo Sokač, Dajana (2022) Novel Synthetic Routes to Quaternary Pyridinium Salts and their Antifungal Activity. Croatica Chemica Acta, 95 (1). pp. 31-38. ISSN 00111643

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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-3aldoxime, 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 & mu;g 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 & mu;g mL-1.

Item Type:	Article
Uncontrolled Keywords:	antifungal activity; dihaloalkanes; deep eutectic solvents; microwave synthesis; quaternization; pyridine derivatives; ultrasound synthesis
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	NMR Center
Depositing User:	Josipa Karadžole
Date Deposited:	05 May 2026 08:45
URI:	https://fulir.irb.hr:/id/eprint/11894
DOI:	10.5562/cca3903

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