Broad Spectrum Fungicidal Activity of the Synthesised 5, 5-Dihydro-1,3,4-Thiadiazolo- [3, 2-A]- [1,3,5]-Triazin-5-Ones

Article Sidebar

PDF HTML
Published: Mar 1, 2024
DOI: https://doi.org/10.29070/xhm36g33
Keywords:
Thiadiazolotriazinone derivatives, Broad-spectrum antifungal, Fungicidal activity, SAR analysis, Antifungal resistance

Main Article Content

Authors

Ashwini Kumar

Research Scholar, P.G. Dept. of Chemistry, Magadh University, Bodh Gaya, Bihar

Abstract

It is crucial to discover new fungicidal medications since hazardous fungi are becoming increasingly resistant to the therapies that are already available. The purpose of this study was to manufacture a variety of 5,5-dihydro-1,3,4-thiadiazolo-[3,2-a]- [1,3,5]-triazin-5-one derivatives and evaluate their antifungal efficacy throughout a wide range. In order to get further information on the synthesized substances, we made use of nuclear magnetic resonance, mass spectrometry, and infrared spectroscopy instruments. The in vitro antifungal tests that were conducted included the testing of a number of different fungal strains, including Candida albicans, Aspergillus niger, Fusarium exospore, and Trichophyton mentagrophytes. These strains are significant in a variety of situations, including clinical and agricultural ones. A variety of substances had potent antifungal action, with minimum inhibitory concentrations (MICs) that were comparable to or lower than those of antifungal drugs that are already on the market. Electron-withdrawing substituents were shown to be useful in increasing the efficiency of antifungal agents, as indicated by structure-activity relationship (SAR) studies. Taking into consideration these findings, 5,5-dihydro-1,3,4-thiadiazolo-[3,2-a]-[1,3,5]-triazin-5-ones seem to be an excellent building block for the development of novel broad-spectrum fungicide medicines.

Downloads

Download data is not yet available.

Article Details

Issue

Vol. 21 No. 1 (2024): Journal of Advances in Science and Technology (JAST)

Section

Articles

References

  1. Parmar, K. (2011). A simple and efficient procedure for synthesis of biologically active 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole-2-aryl-thiazolidine-4-one derivatives. Research Journal of Chemical Sciences, 1, 18–26.
  2. Kadi, A. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M., & ElEmam, A. A. (2010). Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-1, 3, 4-thiadiazole derivatives. European journal of medicinal chemistry, 45(11), 5006–5011.
  3. Leonard, K. J., & Szabo, L. J. (2005). Stem rust of small grains and grasses caused by puccinia graminis. Molecular plant pathology, 6(2), 99–111.
  4. Foroumadi, A., Emami, S., Hassanzadeh, A., Rajaee, M., Sokhanvar, K., Moshafi, M. H., & Shafiee, A. (2005). Synthesis and antibacterial activity of n-(5-benzylthio-1, 3, 4-thiadiazol-2-yl) and n-(5-benzylsulfonyl-1, 3, 4-thiadiazol-2-yl) piperazinyl quinolone derivatives. Bioorganic & medicinal chemistry letters, 15(20), 4488– 4492.
  5. Mathew, V., Keshavayya, J., & Vaidya, V. (2006). Heterocyclic system containing bridgehead nitrogen atom: Synthesis and pharmacological activities of some substituted 1, 2, 4-triazolo [3, 4-b]-1, 3, 4-thiadiazoles. European journal of medicinal chemistry, 41(9), 1048–1058.
  6. Brea, C. (1975). U.s. patent 3,901,903 [Chemical Abstracts, 1976, 84, 17364].
  7. Chen, Z., Xu, W., Liu, K., Yang, S., Fan, H., Bhadury, P. S., Hu, D.-Y., & Zhang, Y. (2010). Synthesis and antiviral activity of 5-(4-chlorophenyl)-1, 3, 4-thiadiazole sulfonamides. Molecules, 15(12), 9046–9056.
  8. Jatav, V., Jain, S., Kashaw, S., & Mishra, P. (2006). Synthesis and antimicrobial activity of novel 2-methyl-3-(1′ 3 ′ 4 ′ -thiadiazoyl)-4-(3h) quinazolinones. Indian journal of pharmaceutical sciences, 68(3).
  9. Katritzky, A., & Rees, C. (1995). Scriven. efv eds. Pergamon Press: Oxford, 5, 469.
  10. Bird, C. W., & Katritzky, A. R. (1984). Comprehensive heterocyclic chemistry: The structure, reactions, synthesis and uses of heterocyclic compounds;[in 8 volumes]. 4. pergamon press.
  11. Azab, M. E., Youssef, M. M., & El-Bordany, E. A. (2013). Synthesis and antibacterial evaluation of novel heterocyclic compounds containing a sulfonamido moiety. Molecules, 18(1), 832–844.
  12. Husain, A., Asif, M., Bhutani, R., & Dutta, M. (2013). Triazolothiadiazoles as antimicrobial agent: A short riview. World Journal of Pharmaceutical Sciences, 1(4), 138–150.
  13. Gupta, S. K., Sharma, P., Bansal, M., & Kumar, B. (2011). Synthesis of 5-(o-hydroxy phenyl)-2-[4’aryl-3’chloro-2’azetidinon-1-yl]-1, 3, 4-thiadiazole and further evaluated antifungal activity. EJ Chem, 8(2), 594–597.
  14. Adhikari, A., Bhakta, S., & Ghosh, T. (2022). Microwave-assisted synthesis of bioactive heterocycles: An overview. Tetrahedron, 133085.
  15. Yadav, L. D. S., Misra, A. R., & Singh, H. (1988a). [4+ 2] cycloaddition of conjugated azomethines to aryl isothiocyanates and fungitoxicity of the resulting 6, 7-dihydro-1, 3, 4-oxadiazolo [3, 2-a]-s-triazine-5-thiones. Journal of Agricultural and Food Chemistry, 36(4), 828–831
  16. Yadav, L. D. S., Misra, A. R., & Singh, H. (1988a). [4+ 2] cycloaddition of conjugated azomethines to aryl isothiocyanates and fungitoxicity of the resulting 6, 7-dihydro-1, 3, 4-oxadiazolo [3, 2-a]-s-triazine-5-thiones. Journal of Agricultural and Food Chemistry, 36(4), 828–831
  17. Abdelli, A., Azzouni, S., Plais, R., Gaucher, A., Efrit, M. L., & Prim, D. (2021). Recent advances in the chemistry of 1, 2, 4-triazoles: Synthesis, reactivity and biological activities. Tetrahedron Letters, 86, 153518.
  18. Varandas, L., Fraga, C., Miranda, A., & Barreiro, E. (2005). Design, synthesis and pharmacological evaluation of new nonsteroidal antiinflammatory 1, 3, 4-thiadiazole derivatives. Letters in Drug Design & Discovery, 2(1), 62–67.
  19. Xu, P.-F., Zhang, Z.-H., Hui, X.-P., Zhang, Z.-Y., & Zheng, R.-L. (2004). Synthesis of triazoles, oxadiazoles and condensed heterocyclic compounds containing cinchopheny and studies on biological activity of representative compounds. Journal of the Chinese chemical Society, 51(2), 315–319.
  20. Yusuf, M., Khan, R. A., & Ahmed, B. (2008). Syntheses and anti-depressant activity of 5-amino-1, 3, 4-thiadiazole-2-thiol imines and thiobenzyl derivatives. Bioorganic & medicinal chemistry, 16(17), 8029–8034.