Skip to main content
SpringerLink
Log in

In silico rationalized novel low molecular weight 1,2,4-triazolyldithiocarbamates: Design, synthesis, and mycocidal potential

  • Various Technological Processes
  • Published:
Russian Journal of Applied Chemistry Aims and scope Submit manuscript

Abstract

1,2,4-Triazole and dithiocarbamates are proven leads in the field of phytopathological antifungal regime. In our continuous efforts to discover 1,2,4-triazoles as antifungals with augmented potential, novel hybridized molecules were designed and screened on the basis of in silico studies. The compounds were evaluated for their in vitro mycocidal potential against various phytopathogenic fungi. 40 novel molecules were passed through four stage screening process to select the most potent mycocidal compounds. The first three stages of in silico analysis viz. Lipinski filtration, docking studies and toxicity analysis approved 20 compounds and fourth stage screening involved molecular weight as vital conversion parameter. Compounds with low molecular weight viz. 4, 24 and 29, came out to be the best compounds inflicting potential comparative to standard fungicide Tilt. The vitality of low molecular weight of biomolecules was revealed as promising conversion factor with compounds inflicting antifungal potential comparative to standard fungicides used.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Worthington, P.A., Sterol Biosynthesis Inhibitors, Berg, D. and Plempel, M., Eds., London: Ellis Horwood, 1988.

  2. Zan, X.I., Lai, L.H., Ji, G.Y., and Zhon, Z.X., J. Agric. Food Chem., 2002, vol. 50, pp. 3757–3760.

    Article  Google Scholar 

  3. US Patents, 65967250 B2, 2003.

  4. US Patent, 8338338 B2, 2012.

  5. Corbaz, R., Principles of Phytopathology and Control of Plant Diseases, Lausanne: Presses Polytechniques et Universitaires Romandes, pp. 284, 1990.

    Google Scholar 

  6. Khan, H., Badshah, A., Murtaz, G., Said, M., Rehman, Z., Neuhausen, C., Todorova, M., Jean-Claude, B., and Butler, I.S., Eur. J. Med. Chem., 2011, vol. 46, pp. 4071–4077.

    Article  CAS  Google Scholar 

  7. Husain, A., Shahab, A.A.N., Singh, S.P., Oves, M., and Siddiqi, K.S., Polyhedron, 2011, vol. 30, pp. 33–40.

    Article  CAS  Google Scholar 

  8. Shahnaz, M., Namarta, Sharma, J., Parkash, J., and Parsad, D.N., J. Drug Deliv. Ther., 2013, vol. 3, pp. 110–114.

    Google Scholar 

  9. Mujawar, S., Utture, S., Fonseca, E., Matarrita, J., and Banerjee, K., Food Chem., 2014, vol. 150, pp. 175–181.

    Article  CAS  Google Scholar 

  10. Basirah, A., Hasan, M.F.A., Norliawati, M.S., Khairul, W.M., and Noraznawati, I., J. Appl. Sci. Res., 2014, vol. 9, pp. 5562–5567.

    Google Scholar 

  11. Palanisamy, J.R. and Subbiah, T., Eur. J. Med. Chem. 2013, vol. 62, pp. 139–147.

    Article  Google Scholar 

  12. Duan, Y.C., Zheng, Y.C., Li, X.C., Wang, M.M., Ye, X.W., Guan, Y.Y., Liu, G.Z., Zheng, J.X., and Liu, H.M., Eur. J. Med. Chem. 2013, vol. 64, pp. 99–110.

    Article  CAS  Google Scholar 

  13. Yavuz, T., Uzun, O., Macit, A., Comunoglu, C., Yavuz, O., Silan, C., Yuksel, H., and Yildirim, H.A., Path-Res Prac., 2013, vol. 209, pp. 302–308.

    Article  CAS  Google Scholar 

  14. Rafin, C., Veignie, E., Sancholle, M., Postal, D., Len, C., Villa, P., and Ronco, G., J. Agric. Food Chem. 2000, vol. 48, pp. 5283–5287.

    Article  CAS  Google Scholar 

  15. Leka, Z., Bulatovic, D., and Latinovic, N., Reporting for Sustainability, 2013, p.495.

    Google Scholar 

  16. Qin, Y., Liu, S., Xing, R., Yu, H., Li, K., Meng, X., Li, R., and Li, P., Carbohydrate Polymers, 2012, vol. 89, pp. 388–393.

    Article  CAS  Google Scholar 

  17. Sidhu, A. and Kukreja, S., Arab. J. Chem., 2015.

    Google Scholar 

  18. Kukreja, S., Sidhu, A., and Sharma, V.K., Res. Chem. Inter., 2016, vol. 42, pp. 1–16.

    Article  Google Scholar 

  19. Gumber, K., Sidhu, A., and Kumar, V., Russ. J. Appl. Chem. 2015, vol. 88, pp. 2065–2073

    Article  CAS  Google Scholar 

  20. Sidhu, A., Sharma, P., Gumber, K., and Sharma, V.K., Pl. Dis. Res. 2016, vol. 31, pp. 114–117.

    Google Scholar 

  21. Puratchikody, A., Doble, M., and Ramalakshmi, N., J. Pharm. Res., 2012, vol. 5, pp. 340–342.

    Google Scholar 

  22. Hafeez, A., Saify, Z.S., Naz, A., Yasmin, F., and Akhtar, N., J. Comp. Med., 2013, pp. 1–5.

    Google Scholar 

  23. Weininger, D., J. Chem. Inf. Mod., vol. 28, pp. 31–36.

  24. Devi, T.R. and Chhetry, G.K.N., Int. J. Sci. Res. Pub. 2012, vol. 2, pp. 1–4.

    Google Scholar 

  25. Finney, D.J., Probit Analysis, Cambridge: University Press, 1971.

    Google Scholar 

  26. Avram, S., Funar-Timofei, S., Barota, A., Chennamaneni, S.R., Manchala, A.K., and Muresan, S., J. Cheminf. 2014, vol. 6, pp. 42–52.

    Article  Google Scholar 

  27. Lipinski, C.A., Lombardo, F., Dominy, B.W., and Feeney, P.J., Adv. Drug Deliv. Rev., 1997, vol. 46, pp. 3–25.

    Article  Google Scholar 

  28. Tice, C.M., Pest Manag. Sci. 2001, vol. 57, pp. 3–16.

    Article  CAS  Google Scholar 

  29. Xanthopoulou, M.N., Hadjikakou, S.K., Hadjiliadis, N., Kubicki, M., Karkabounas, S., Haralabopoulos, K., Kourkoumelis, N., and Bakas, T., J. Org. Chem. 2009, vol. 691, pp. 1780–1789.

    Article  Google Scholar 

  30. Cramer, G.M., Ford, R.A., and Hall, R.L., Estimation of Toxic Hazard, Pergamon Press, 1978, vol. 16, pp. 255–276.

    CAS  Google Scholar 

  31. Benigni, R., Bossa, C., and Tcheremenskaia, O., Chem. Rev. 2013, vol. 113, pp. 2940–2957.

    Article  CAS  Google Scholar 

  32. http://ihcp.jrc.ec.europa.eu/our_labs/computational_toxicology/doc/Toxtree_start_manual.pdf

  33. Humeres, E., Debacher, N.A., Mardta, M., and Sierra, S., J. Org. Chem. 1999, vol. 64, pp. 1807.

    Article  CAS  Google Scholar 

  34. Sidhu, A., Sidhu, S.S., and Vineet, Rai, M., Pest Res. J., 2011, vol. 23, pp. 88–95.

    CAS  Google Scholar 

  35. https://indofilcc.com/wp-content/uploads/2011/12/m45.pdf

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Punjab Agricultural University, Ludhiana, 141004, India

    Khushbu Gumber & Anjali Sidhu

  2. Department of Plant Pathology, Punjab Agricultural University, Ludhiana, 141004, India

    Vineet K. Sharma

Authors
  1. Khushbu Gumber
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Anjali Sidhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Vineet K. Sharma
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Khushbu Gumber.

Additional information

The text was submitted by the authors in English.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gumber, K., Sidhu, A. & Sharma, V.K. In silico rationalized novel low molecular weight 1,2,4-triazolyldithiocarbamates: Design, synthesis, and mycocidal potential. Russ J Appl Chem 90, 993–1004 (2017). https://doi.org/10.1134/S1070427217060222

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070427217060222

Search

Navigation