Antimicrobial and Biochemical Activities of Some Arylazomorpholine Derivatives

Ahmed S. Abdel-Aty; Mohamed A. Desheesh; Ahmed M. Allam

doi:10.14233/ajchem.2015.18872

Issue

Vol. 27 No. 10 (2015): Vol 27 Issue 10

Issue Published : June 22, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Antimicrobial and Biochemical Activities of Some Arylazomorpholine Derivatives

https://doi.org/10.14233/ajchem.2015.18872

Ahmed S. Abdel-Aty

Department of Pesticide Chemistry and Technology, Faculty of Agriculture, Alexandria University, 21545-El-Shatby, Alexandria, Egypt

Mohamed A. Desheesh

Department of Pesticide Chemistry and Technology, Faculty of Agriculture, Alexandria University, 21545-El-Shatby, Alexandria, Egypt

Ahmed M. Allam

Department of Pesticide Chemistry and Technology, Faculty of Agriculture, Alexandria University, 21545-El-Shatby, Alexandria, Egypt

Corresponding Author(s) : Ahmed S. Abdel-Aty

sabry2000@yahoo.com

Asian Journal of Chemistry, Vol. 27 No. 10 (2015): Vol 27 Issue 10
Article Published : June 22, 2015

Abstract

Ten arylazomorpholines were prepared and characterized. Their fungicidal activity against Fusarium oxysporum, Rhizoctonia solani, Macrophomina phasoli, Helminthosporum sp. and Trichoderma harzianum and antibacterial effects against Erwinia amylovora were examined. Derivatives with persuasive in vitro antifungal effects, were checked in vivo on polyphenoloxidase, peroxidase DNA, RNA and sugar contents of Rhizoctonia solani as biomarkers searching their main target. 4-(4-Chlorophenyl)-, 4-(3-chlorophenyl)-, 4-(2-chlorophenyl)- and 4-(4-hydroxy-3,5-dichlorophenyl)azomorpholines highly inhibited all the tested fungi comparing with the standard fungicide metalaxyl. 4-(4-Chlorophenyl)azomorpholine and 4-(2-chlorophenyl)azomorpholine were more effective than metalaxyl inhibiting the hyphal growth of R. solani in liquid media. 4-(Phenyl)azomorpholine and 4-(3-chlorophenyl)azomorpholine completely stopped E. amylovora growth with MIC 4 × 10^-5 M similar to streptomycin. 4-(4-Chlorophenyl)azomorpholine and 4-(4-hydroxy-3,5-dichlorophenyl)azomorpholine stimulated polyphenoloxidase and peroxidase. The tested arylazomorpholine derivatives were not specific against DNA and RNA contents. 4-(4-Chlorophenyl)-azomorpholine proved to be more potent than metalaxyl in reducing total soluble sugars and reduced sugars, whereas metalaxyl was near to it on non-reducing sugars.

Keywords

Azomorpholine Fungicidal Antibacterial Polyphenoloxidase Peroxidase DNA RNA Sugars

S. Abdel-Aty, A., A. Desheesh, M., & M. Allam, A. (2015). Antimicrobial and Biochemical Activities of Some Arylazomorpholine Derivatives. Asian Journal of Chemistry, 27(10), 3579–3585. https://doi.org/10.14233/ajchem.2015.18872

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References

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References

J.A.H. Lainton, M.C. Allen, M. Burton, S. Cameron, T.R.G. Edwards, G. Harden, R. Hogg, W. Leung, S. Miller, J.J. Morrish, S.M. Rooke and B. Wendt, J. Comb. Chem., 5, 400 (2003); doi:10.1021/cc020052f.

Pesticide Manual, Basic Information on the Chemicals Used as Active Compounds of Pesticides, edn 13, Version 3.1 (2011).

G. Aridoss, S. Balasubramanian, P. Parthiban and S. Kabilan, Eur. J. Med. Chem., 42, 851 (2007); doi:10.1016/j.ejmech.2006.12.005.

Q. Zheng, K. Cheng, X. Zhang, K. Liu, Q. Jiao and H. Zhu, Eur. J. Med. Chem., 45, 3207 (2010); doi:10.1016/j.ejmech.2010.03.027.

V. Kanagarajan, J. Thanusu and M. Gopalakrishnan, Eur. J. Med. Chem., 45, 1583 (2010); doi:10.1016/j.ejmech.2009.12.068.

P. Panneerselvam, R.R. Nair, G. Vijayalakshmi, E.H. Subramanian and S.K. Sridhar, Eur. J. Med. Chem., 40, 225 (2005); doi:10.1016/j.ejmech.2004.09.003.

D. Zocco, J. Fontaine, E. Lozanova, L. Renard, C. Bivort, R. Durand, A. Grandmougin-Ferjani and S. Declerck, Mycol. Res., 112, 592 (2008); doi:10.1016/j.mycres.2007.11.010.

R.A. Henry and W.M. Dehn, J. Am. Chem. Soc., 65, 479 (1943); doi:10.1021/ja01243a504.

S. Sengupta and S.K. Sadhukhan, Org. Synth., 79, 52 (2002); doi:10.15227/orgsyn.079.0052.

M.A. Desheesh, Sh.M. Kassem, S.T. El-Deeb and M.A. El-Sebaii, Commun. Sci. Develop. Res., 13, 75 (1986).

Cohort Software Inc, Costat Users Manual, Version 3.03 Berkeley, California, USA (1986).

J.H. Topps and R.L. Wain, Ann. Appl. Biol., 45, 506 (1957); doi:10.1111/j.1744-7348.1957.tb05888.x.

O.H. Lowry, N.J. Rosebrough, A.L. Farr and R.J. Randall, J. Biol. Chem., 193, 265 (1951).

S. Broesch, Bull. Soc. Chem. Biol. (Paris), 36, 711 (1954).

H. Fehrmann and A.E. Dimond, Phytopathology, 57, 69 (1967).

E.A. Stroev and V.G. Makarova, Laboratory Manual in Biochemistry, Mir Publishers, Moscow, pp. 70-71 (1989).

W. Thomas and R.A. Dutcher, J. Am. Chem. Soc., 46, 1662 (1924); doi:10.1021/ja01672a015.

M.A. Islam, M.M. Alam, M.E. Choudhury, N. Kobayashi and M.U. Ahmed, Bangl. J. Vet. Med., 6, 121 (2008).

EUCAST Definitive Document E. Def 3.1: Antimicrobial Susceptibility Testing (EUCAST) of the European Society of Clinical Microbiology and Infectious Diseases (ESCMID), CMI, vol. 6, p. 509 (2000).

D.J. Finney, Probit Analysis, Cambridge University Press, London, edn 3, p. 138 (1971).

Issue

Vol. 27 No. 10 (2015): Vol 27 Issue 10

Antimicrobial and Biochemical Activities of Some Arylazomorpholine Derivatives

Corresponding Author(s) : Ahmed S. Abdel-Aty

Abstract

Keywords

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