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Synthesis and Fungicidal Activity of Bioactive 4,4'-bis[4"-(N-Benzylidinylamine)-3"-mercapto-1",2",4"-triazole-5"-yl methoxy]dibenzyl
Asian Journal of Chemistry,
Vol. 29 No. 1 (2017): Vol 29 Issue 1
Abstract
The reaction of 4,4'-diamino dibenzyl (I) with sodium nitrite and HCl at 0-5 °C followed by hydrolysis gave 4,4'-dihydroxy dibenzyl (II), which on reaction with chloroacetic acid in presence of sodium carbonate yielded 4,4'-ethylenebisphenoxyacetic acid (III). Nucleophilic substitution of compound III with hydrazine hydrate gave 4,4'-bis(methoxycarbohydrazide)dibenzyl (IV) which on condensation with CS2 and KOH gave 4'4-bis-[(3"-mercapto-1",2",4"-oxadiazole-5"-yl)methoxy]dibenzyl (V). Compound V further condensed with hydrazine hydrate and yielded 4’4-bis[4"-amino-3"-mercapto-1",2",4"-triazole-5"yl methoxy]dibenzyl (VI). It on condensation with different carbonyl compounds gave 4,4’-bis[4"-(N-benzylidinylamine)-3"-mercapto-1",2",4"-triazole-5"yl methoxy]dibenzyl (VIIa-h). Compounds (VIIa-h) were evaluated in vitro for their fungi toxicities against Aspergillus niger and Fusarium oxysporum.
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- Y. Asakawa, M. Tori, K. Takikawa, H.G. Krishnamurty and S.K. Kar, Phytochemistry, 26, 1811 (1987).
- T. Hashimoto, M. Tori and Y. Asakawa, Phytochemistry, 27, 109 (1988).
- U.V. Laddi, S.R. Desai, Y.S. Somannavar, R.S. Bennur and S.C. Bennur, Indian J. Chem., 37B, 461(1998).
- M.B. Talawar, S.R. Desai, Y.S. Somannavar, S.C. Marihal and S.C. Bennur, Indian J. Heterocycl. Chem., 5, 215 (1996).
- A.L. Barry, The Antimicrobic Susceptibility Test, Principle and Practices, ELBS, London, edn 4, (1976).
- I.R. Siddiqui, J. Singh, P.K. Singh, S. Dwivedi, P.K. Shukla and J. Singh, Indian J. Heterocycl. Chem., 14, 231 (2005).
- I.R. Siddiqui, J. Singh, P.K. Singh and J. Singh, Indian J. Chem., 44B, 1460 (2005).
- I.R. Siddiqui, P.K. Singh, J. Singh and J. Singh, Indian J. Chem., 44B, 2102 (2005).
- P.K. Singh and I.R. Siddiqui, Indian J. Chem., 48B, 1013 (2009).
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- I.R. Siddiqui, S. Dwivedi, P.K. Shukla, S. Jaiswal and N.A. Siddiqui, J. Indian Chem. Soc., 83, 89 (2006).
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- I.R. Siddiqui, P.K. Singh, J. Singh and J. Singh, J. Agric. Food Chem.,51, 7062 (2003).
- C.R. Fuson and H.O. House, J. Am. Chem. Soc., 75, 1325 (1953).
- J.G. Horsfall, Bot. Rev., 11, 357 (1945).
References
Y. Asakawa, M. Tori, K. Takikawa, H.G. Krishnamurty and S.K. Kar, Phytochemistry, 26, 1811 (1987).
T. Hashimoto, M. Tori and Y. Asakawa, Phytochemistry, 27, 109 (1988).
U.V. Laddi, S.R. Desai, Y.S. Somannavar, R.S. Bennur and S.C. Bennur, Indian J. Chem., 37B, 461(1998).
M.B. Talawar, S.R. Desai, Y.S. Somannavar, S.C. Marihal and S.C. Bennur, Indian J. Heterocycl. Chem., 5, 215 (1996).
A.L. Barry, The Antimicrobic Susceptibility Test, Principle and Practices, ELBS, London, edn 4, (1976).
I.R. Siddiqui, J. Singh, P.K. Singh, S. Dwivedi, P.K. Shukla and J. Singh, Indian J. Heterocycl. Chem., 14, 231 (2005).
I.R. Siddiqui, J. Singh, P.K. Singh and J. Singh, Indian J. Chem., 44B, 1460 (2005).
I.R. Siddiqui, P.K. Singh, J. Singh and J. Singh, Indian J. Chem., 44B, 2102 (2005).
P.K. Singh and I.R. Siddiqui, Indian J. Chem., 48B, 1013 (2009).
I.R. Siddqui and S. Dwivedi, J. Indian Chem. Soc., 86, 149 (2009).
I.R. Siddiqui, S. Dwivedi, P.K. Shukla, S. Jaiswal and N.A. Siddiqui, J. Indian Chem. Soc., 83, 89 (2006).
I.R. Siddiqui, S. Dwivedi, A. Srivastava, P.K. Shukla and P.K. Singh, Indian J. Heterocycl. Chem., 14, 251 (2005).
I.R. Siddiqui, P.K. Singh, J. Singh and J. Singh, J. Agric. Food Chem.,51, 7062 (2003).
C.R. Fuson and H.O. House, J. Am. Chem. Soc., 75, 1325 (1953).
J.G. Horsfall, Bot. Rev., 11, 357 (1945).