Share This Article:

Synthesis and fungicidal activity of some sulphide derivatives of O-phenyl-N-substituted phenylcarbamates

Abstract Full-Text HTML Download Download as PDF (Size:84KB) PP. 122-127
DOI: 10.4236/abc.2011.13015    5,344 Downloads   10,213 Views   Citations

ABSTRACT

Monosulphides of O-phenyl-N-substituted phenylcar- bamates were prepared by the reaction between O- phenyl-N-substituted phenylcarbamates and sulph- ur dichloride while the corresponding disulphides were prepared by the reaction between O-phenyl-N- substituted phenylcarbamates and sulphur monoch- loride. The synthesized compounds were characte-rized by elemental analysis, thin layer chromatogra-phy (TLC), Fourier-transform infrared, 1H and 13C nuclear magnetic resonance spectroscopic techniques. In vitro fungicidal assay of these sulphides against Fusarium oxysporum, Aspergillus niger, Aspergillus flavus and Rhizopus stolonifer showed that they were more fungicidal than their parent carbamates. The synthesized sulphides were more active towards As-pergillus niger and Aspergillus flavus. There was little or no variations in the fungicidal activities of the synthesized monosulphides and disulphides of O-phen- yl-N-substituted phenyl carbamates.

Conflicts of Interest

The authors declare no conflicts of interest.

Cite this paper

Adelowo, F. , Ojo, I. and Amuda, O. (2011) Synthesis and fungicidal activity of some sulphide derivatives of O-phenyl-N-substituted phenylcarbamates. Advances in Biological Chemistry, 1, 122-127. doi: 10.4236/abc.2011.13015.

References

[1] Lamberth, C. (2004) Sulfur chemistry in crop protection. Journal of Sulfur Chemistry, 25, 39-62. doi:10.1080/17415990310001612290
[2] Adelowo-Imeokparia, F., Faboya, O.O.P. and Ojo, I.A.O., (2005) Synthesis and fungicidalactivity of some phenyl carbamates. International Journal of Chemistry, 15, 101- 111.
[3] Lukens, R.J. (1971) Chemistry of fungicidal action. Chapman and Hall Ltd., London, 1-138.
[4] Metcalf, R.L. (1971) Chemistry and biology of pesticides. In: White-Stevens, R., Ed., Pesticides in The Environment, R. Dekker, New York, 1.
[5] Cremlyn, R. (1979) Pesticides: Preparation and mode of action. John Wiley and Sons, Ltd., Hoboken, 114-115.
[6] Young, D.E. (1988) U.S. Patent No. 726144.
[7] Ayodele, E.T. (1994) Studies in the synthesis and fungi-cidal activity of some substituted benzyl-2-hydroxyethyl oligosulphide and related compounds. Ph.D thesis, Uni-versity of North London, London.
[8] Sonawane L.V. and Bari, S.B. (2011) Synthesis and spectral characterization of some novel n-substituted 2, 4-Thiazolidinedione. International Journal of Biological Chemistry, 5, 68-74.doi:10.3923/ijbc.2011.68.74
[9] Rich, S. (1960) Fungicidal chemistry in plant pathology. Academy Press Ltd., New York, 588.
[10] Eyring, H., (1966) Untangling biological reactions. Science, 154, 1609-1613.thiodicarbamates. J. Agr. Food Chem, 26, 550-557.
[11] Pattan, S.R., Suresh, C., Pujari, V.D., Reddy, V.V.K., Rasal V.P. and Koti, B.C. (2005) Synthesis and antidiabetic activity of 2-amino [5’(4-sulphonylbenzylidine)-2, 4-thiazolidinedione]-7-chloro-6-fluoro-benzothiazole. In-dian Journal of Chemistry, 44, 2404-2408.
[12] Grogan, C.H.; Rice, L.M. and Reid, E.E. (1955) Dithiols and derivatives. Journal of Organic Chemistry, 20, 50- 58. doi:10.1021/jo01119a009
[13] Field, L., Owen, T.C., Crenshaw, R.R. and Bryan, A.W. (1961) Organic disulfides and related substances. IV. Thiolsulfonates and disulfides containing 2-aminoethyl moieties. Journal of the American Chemical Society, 83, 4414-4417. doi:10.1021/ja01482a027
[14] Szczepanski, C.V., Heindl, J.; Hoyer, G.A. and Schroder, E. (1977) Biologically active substances in plants. II: Synthesis and antimicrobial activity of some unsymme-trical oligosulphides. European journal of medicinal chemistry: Chimica therapeuticaI, 12, 279-284.
[15] Fahmy, M.A.H. and Fukuto, T.R. (1981) N-sulfinylated de- rivatives of methylcarbamate esters. Journal of Agri-cultural and Food Chemistry, 29, 567-572. doi:10.1021/jf00105a034
[16] Ayodele, E.T.; Hudson, H.R.; Ojo, I.A.O. and Pianka, M. (2000) Organosulfur compounds aspotential fungicides: The preparation and properties of some substituted benzyl 2-hydroxylethyl oligosulfides. Journal of Phosphorus, Sulfur and Silicon, 159, 123-142. doi:10.1080/10426500008043656
[17] Mori, M., Takagi, M., Noritake, C. and Kagabu, S. (2008) 2, 4-Dioxo-1,3-thiazolidine derivatives as a lead for new fungicides”. Journal of Pesticide Science, 33, 357-363. doi:10.1584/jpestics.G08-15
[18] Vedavathi, M., Somashekar, B, Sreenivasa, G.M. and Jayachandran, E. (2010) Synthesis, characterization and anti-microbial activity of fluoro benzothiazole incorporated with 1,3,4-Thiadiazole. Journal of Pharmaceutical Sciences and Research, 2, 53-63.
[19] Reid, E.E. (1960) Organic chemistry of bivalent sulphur. Chemical Publishing Co. Inc., New York, III, 363-367.
[20] Kharasch, N. (1961) Organic sulphur compounds. Per-gamon Press, Oxford, 30-51.
[21] Kuhle, E. (1970) One hundred years of sulfenic acid chemistry, sulfenyl halide synthesis. Synthesis, 11, 560- 580.
[22] Ayodele, E.T. (2005) Preparation and glass house screening of some substituted benzyl-2-hydroxylethyl oligosulfides. Science Focus, 10, 56-62.
[23] Adelowo-Imeokparia, F. and Ojo, I.A.O. (2006) Synthe-sis and fungicidal activity of some sulphide derivatives of O-ethyl-N-substituted phenylcarbamates. Pakistan Jour- nal of Scientific and Industrial Research, 49, 324-329.
[24] Tabakova, S. and Dodoff, N. (1995) Effect of platinum (II) complexes of benzoic and 3-methoxybenzoic acid hydrazides on Saccharomyces serevisiae. Zeitschrift für Naturforschung, 50c, 732-743.

  
comments powered by Disqus

Copyright © 2019 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.