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Fungicidal activity of thionocarbamates derivatives of alcohols

Agata Ptaszek-Budniok 1Anna E. Kasprzycka 1Przemysław Hahn 1Andrzej Dzienia 1Wiesław Szeja 1Mirosława Sioła 2Marian Zembala 2

1. Silesian University of Technology, Department of Organic Chem., Bioorganic Chem. and Biotechnol., Krzywoustego 4, Gliwice 44-100, Poland
2. Silesian Center for Heart Diseases in Zabrze (SCCS), M. Curie-Sklodowskiej 9, Zabrze 41-800, Poland

Abstract

N-Allyl and N-aryl thionocarbamates are an important class of compounds that have received considerable attention in the literature [1]. Such compounds are of interest due to their numerous biological effects including anesthetic, fungicidal, bactericidal, pesticidal, and antiviral [1-5]. Thionocarbamates as fungicides have been extensively studied since 1960 [4]. However, little attention had been given to N-allyl and N-aryl substituted thionocarbamates derivatives alcohols until Thorne [5] studied a wide variety of derivetives of thiocarbamic and carbamic acids. He found that phenyl carbamates, alkyl-phenyl carbamates, and alkyl thiophenyl carbamates have low fungitoxicity and that some thionocarbamates showed activity. To study the possibility of improving the fungicidal activity of the known thionocarbamates, in the present work a series of N-alkyl, N-phenyl and N-benzyl thionocarbamates derivatives alcohols were synthesized (Figure 1), and their fungitoxic activity was tested for yeasts (Candida albicans, Candida dubliniensis, Candida tropicalis, Candida glabrata, Candida krusei, Candida parapsilosis) isolated from clinical materials in the Laboratory of Microbiology, Silesian Center for Heart Diseases in Zabrze. Results presented in this paper reveal good fungicidal activity of certain N-allyl, N-phenyl and N-benzyl thionocarbamates.

 

Acknowledgement:

Research studies part-financed by the European Union within the European Regional Development Fund (POIG.01.01.02-14-102/09).

 References:

[1] Albores-Velasco, M. Thorne, J. Wain, R.L., J. Agric. Food Chem., 43, 2260-2261, 1995.

[2] Cesarini, S., Spalarossa A., Ranise A., Schenone S., Bruno O., Colla P., Casula L., Collu G., Sanna G., Loddo R., Bioorganic &Medicinal Chemistry, 16, 6353-6363, 2008

[3] Hart, B.W., Faiman, M.D., Biochemical Pharmacology,16,157-163, 1995

[4] Ludwig, R.A.; Thorn, G.D., Adwances in Pest Control Reserch; Interscience: New York, 1960; Vol.3.

[5] Thorne, J. Chemical structure in relation to biological activity of certain carbamic acid derivatives. Ph.D Dissertation, University of London, 1967.

 

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Presentation: Poster at IX Multidyscyplinarna Konferencja Nauki o Leku, by Agata Ptaszek-Budniok
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Submitted: 2014-03-14 13:34
Revised:   2014-05-02 17:40