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Appl Environ Microbiol. 1967 July; 15(4): 710-717
Copyright © 1967 American Society for Microbiology. All Rights Reserved.

Antifungal Activity of Isothiocyanates and Related Compounds

II. Mononuclear Aromatic Isothiocyanates

. Drobnica, M. Zemanová, P. Nemec, P. Kristián, K. Anto and A. Hulka

Department of Microbiology and Biochemistry and Department of Organic Chemistry, Faculty of Chemistry, Slovak Polytechnical University, Bratislava, SSR
Department of Microbiology, Faculty of Natural Sciences, Komensk University, Bratislava, SSR

ABSTRACT

Antifungal activity on Aspergillus niger, Penicillium cyclopium, and Rhizopus oryzae, as well as on additional saprophytic and parasitic fungi, was determined in 57 substituted derivatives of phenylisothiocyanate. Most of the investigated compounds displayed rather equal activity against the three mentioned fungi, in contradistinction to the analogues of natural benzyl- and ß-phenylethylisothiocyanate with their characteristic low activity against R. oryzae. Differences occurred in the type of activity of compounds in which the —NCS group is directly bound on the aromatic moiety, as compared with those compounds in which this group is bound to the aliphatic radical or to the aromatic moiety indirectly by means of the methyl group or by a longer aliphatic chain. The results obtained confirm the negative influence of ionized substituents on the aromatic moiety, i.e., of —COOH, —CH₂— COOH, and —SO₃H groups, as well as of substituents which cause an extreme increase in reactivity of the —NCS group resulting in a high instability of the entire isothiocyanate molecule.