Skip to main content
Log in

Design and synthesis of 2-alkylthio-5-(1,2,4-triazol-1-ylmethyl)-1,3,4-thiadiazoles and their fungicidal activity

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The design of 2-alkylthio-5-(1,2,4-triazol-1-ylmethyl)-1,3,4-thiadiazoles was formulated and a three-step synthesis approach was developed, their high fungicidal activity was demonstrated against six species of phytopathogenic fungi in in vitro studies.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. P. Sousa, C. Viegas, Fungal Exposure in Agricultural Environments–A Review, Encyclopedia of Mycology, Amsterdam–Elsevier, 2021, p. 116–124; DOI: https://doi.org/10.1016/B978-0-12-809633-8.21579-3.

    Google Scholar 

  2. R. A. El-Sayed, A. B. Jebur, W. Kang, M. A. El-Esawi, F. M. El-Demerdash, J. Future Foods, 2022, 2, 91; DOI: https://doi.org/10.1016/j.jfutfo.2022.03.002.

    Article  Google Scholar 

  3. T. Ming, F. Yanzhong, H. Xinmiao, Z. Dongjie, W. Wentao, L. Di, Toxicon, 2022, 214, 112; DOI: https://doi.org/10.1016/j.toxicon.2022.05.041.

    Article  Google Scholar 

  4. A. B. Engin, A. Engin, Environmental Toxicology and Pharmacology, 2019, 65, 90; DOI: https://doi.org/10.1016/j.etap.2018.12.006.

    Article  CAS  PubMed  Google Scholar 

  5. S. Luo, H. Du, H. Kebede, Y. Liu, F. Xing, Food Control, 2021, 127, 108120; DOI: https://doi.org/10.1016/j.foodcont.2021.108120.

    Article  CAS  Google Scholar 

  6. F. Massimo, G. Perrone, A. Gallo, Current Opinion in Food Science, 2022, 100923; DOI: https://doi.org/10.1016/j.cofs.2022.100923.

  7. R. P. Singh, P. K. Singh, J. Rutkoski, D. P. Hodson, X. He, L. N. Jørgensen, M. S. Hovmøller, J. Huerta-Espino, Annual Review of Phytopathology, 2016, 54, 303; DOI: https://doi.org/10.1146/annurev-phyto-080615-095835.

    Article  CAS  PubMed  Google Scholar 

  8. V. S. Brauer, C. P. Rezende, A. M. Pessoni, R. G. de Paula, K. S. Rangappam, S. C. Nayaka, V. K. Gupta, F. Almeida, Biomolecules, 2019, 9, 521; DOI: https://doi.org/10.3390/biom9100521.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. W. Żukiewicz-Sobczak, G. Cholewa, P. Sobczak, J. Zagórski, P. Wojtyia-Buciora, Agriculture and Agricultural Science Procedia, 2015, 7, 313; DOI: https://doi.org/10.1016/j.aaspro.2015.12.053.

    Article  Google Scholar 

  10. K. Roe, Microbial Pathogenesis, 2021, 161, 105200; DOI: https://doi.org/10.1016/j.micpath.2021.105200.

    Article  CAS  PubMed  Google Scholar 

  11. M. Singh, P. A. Routledge, Medicine (UK), 2020, 48, 218; DOI: https://doi.org/10.1016/j.mpmed.2019.12.020.

    Google Scholar 

  12. M. Meena, S. Samal, Toxicology Reports, 2019, 6, 745; DOI: https://doi.org/10.1016/j.toxrep.2019.06.021.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  13. V. Navale, K. R. Vamkudoth, S. Ajmera, V. Dhuri, Toxicology Reports, 2021, 8, 1008–1030; DOI: https://doi.org/10.1016/j.toxrep.2021.04.013.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. S. Z. Iqbal, Current Opinion in Food Science, 2021, 42, 237; DOI: https://doi.org/10.1016/j.cofs.2021.07.003.

    Article  CAS  Google Scholar 

  15. M. Shafiei, L. Peyton, M. Hashemzadeh, A. Foroumadi, Bioorg. Chem., 2020, 104, 104240; DOI: https://doi.org/10.1016/j.bioorg.2020.104240.

    Article  CAS  PubMed  Google Scholar 

  16. L. Bielská, S. E. Hale, L. Škulcová, Sci. Total Environment, 2021, 750, 141600; DOI: https://doi.org/10.1016/j.scitotenv.2020.141600.

    Article  Google Scholar 

  17. A. Ahmadi, E. Mohammadnejadi, P. Karami, N. Razzaghi-Asl, Inter. J. Antimicrobial Agents, 2022, 59, 106518; DOI: https://doi.org/10.1016/j.ijantimicag.2022.106518.

    Article  CAS  Google Scholar 

  18. P. E. Verweij, G. H. J. Kema, B. Zwaan, W. J. Melchers, Pest Manag. Sci., 2013, 69, 165; DOI: https://doi.org/10.1002/ps.3390.

    Article  CAS  PubMed  Google Scholar 

  19. G. V. Tsaplin, S. V. Popkov, A. L. Alekseenko, N4-Sub stituted 3-alkylsulfanyl-5-(1,2,4-triazol-1-ylmethyl)-1,2,4-triazoles, method for their preparation, fungicidal and growth-regulatory compositions based on them, RU Pat. 2 668 212 C1, 2017.

  20. G. V. Tsaplin, S. V. Popkov, A. S. Orlova, A. L. Alekseenko, 2-Alkylthio-5-(1H-1,2,4,-triazol-1-yl-methyl)-1,3,4-thiadiazoles, method for their preparation and fungicidal compositions based on them, RU Pat. 2 757 808 C1, 2017.

  21. S. S. Zykova, G. V. Tsaplin, V. S. Talismanov, I. P. Bulatov, S. V. Popkov, O. G. Karmanova, Inter. J. Pharmaceutical Research, 2021, 13, 309; DOI: https://doi.org/10.31838/ijpr/2021.13.01.056.

    Google Scholar 

  22. S. S. Zykova, V. S. Talismanov, G. V. Tsaplin, I. P. Bulatov, S. V. Popkov, O. G. Karmanova, A. V. Savinkov, Inter. J. Pharmaceutical Research, 2019, 11, 1189; DOI: https://doi.org/10.31838/ijpr/2019.11.03.097.

    Google Scholar 

  23. G. V. Tsaplin, S. V. Popkov, Russ. J. Org. Chem., 2022, 58, 1; DOI: https://doi.org/10.1134/S1070428022010018.

    Article  CAS  Google Scholar 

  24. D. V. Pasyukov, A. Y. Chernenko, I. V. Lavrentev, V. A. Baydikova, M. E. Minyaev, O. A. Starovoytova, V. M. Chernyshev, Russ. Chem. Bull., 2022, 71, 993; DOI: https://doi.org/10.1007/s11172-022-3501-7.

    Article  CAS  Google Scholar 

  25. G. G. Danagulyan, A. K. Tumanyan, O. S. Attaryan, R. A. Tamazyan, A. G. Danagulyan, A. G. Ayvazyan, Chem. Heterocycl. Compd., 2015, 51, 483; DOI: https://doi.org/10.1007/s10593-015-1724-3.

    Article  CAS  Google Scholar 

  26. G. P. Yu, W. Z. Bi, G. D. Si, Y. X. Yang, H. A. Aisa, L. Z. Xu, Struct. Chem., 2009, 20, 569; DOI: https://doi.org/10.1007/s11224-008-9404-x.

    Article  CAS  Google Scholar 

  27. G. A. Gazieva, L. V. Anikina, T. V. Nechaeva, S. A. Pukhov, T. B. Karpova, S. V. Popkov, Y. V. Nelyubina, N. G. Kolotyrkina, A. N. Kravchenko, Eur. J. Med. Chem., 2017, 140, 141; DOI: https://doi.org/10.1016/j.ejmech.2017.09.009.

    Article  CAS  PubMed  Google Scholar 

  28. S. V. Popkov, L. V. Kovalenko, M. M. Bobylev, O. Y. Molchanov, M. Z. Krimer, V. P. Tashchi, Y. G. Putsykin, Pestic. Sci., 1997, 49, 125; DOI: https://doi.org/10.1002/(SICI)1096-9063(199702)49:2<125::AID-PS506>3.0.CO;2-0.

    Article  CAS  Google Scholar 

  29. S. Rondeu, N. E. Raine, Environ. International, 2022, 107311; DOI: https://doi.org/10.1016/j.envint.2022.107311.

  30. S. V. Popkov, A. L. Kovalenko, Application of substituted 1-(2-phenoxyethyl)-1,2,4-triazoles as fungicides and fungicidal composition based on them, RU Pat.2 329 646 C2, 2005.

  31. A. O. Kuptsova, E. E. Vinogradova, A. N. Kravchenko, G. A. Gazieva, Russ. Chem. Bull., 2022, 71, 885; DOI: https://doi.org/10.1007/s11172-022-3488-0.

    Article  CAS  Google Scholar 

  32. C. Ainsworth, R. G. Jones, J. Am. Chem. Soc., 1955, 77, 621; DOI: https://doi.org/10.1021/ja01608a028.

    Article  CAS  Google Scholar 

  33. S. V. Popkov, A. L. Alekseenko, Khimicheskaya promyshlennost’ segodnya [Chemical Industry Today], 2007, 5, 36 (in Russian).

    Google Scholar 

  34. S. V. Popkov, A. L. Alekseenko, D. S. Tikhomirov, Izv. VUZov. Ser. Khim. i Khim. Tekhnol. [Bull. Univ. Ser. Chem. and Chem. Technol.], 2007, 50, 98 (in Russian).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to G. V. Tsaplin.

Ethics declarations

The authors declare no competing interests.

Additional information

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 9, pp. 2125–2132, September, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tsaplin, G.V., Zolotukhina, A.S., Alekseeva, E.A. et al. Design and synthesis of 2-alkylthio-5-(1,2,4-triazol-1-ylmethyl)-1,3,4-thiadiazoles and their fungicidal activity. Russ Chem Bull 72, 2125–2132 (2023). https://doi.org/10.1007/s11172-023-4007-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-4007-7

Key words

Navigation