Skip to main content
SpringerLink
Log in

Synthesis, S-alkylation, and fungicidal activity of 4-(benzylideneamino)thioglycolurils

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

Abstract

A series of 1,3-disubstituted 4-benzylideneamino-5-thioxohexahydroimidazo[4,5-d]imidazol-2(1H)-ones (thioglycolurils) was synthesized via the reaction of 5,7-disubstituted 3-thioxoperhydroimidazo[4,5-e]-1,2,4-triazin-6-ones with hydroxy-, alkoxy-, and fluorocontaining benzaldehyde derivatives. An alkylation of the obtained thioglycolurils with methyl iodide or 4-bromobenzyl bromide provided the corresponding 6-benzylideneamino-5-alkylsulfanyl-3,3a,6,6a-tetrahydroimidazo[4,5-d]imidazol-2(1H)-ones. The fungicidal activity of some synthesized compounds against pathogens causing diseases of agricultural crops was studied.

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. E. A. Dlin, G. M. Averochkin, A. V. Finko, N. S. Vorobyeva, E. K. Beloglazkina, N. V. Zyk, Y. A. Ivanenkov, D. A. Skvortsov, V. E. Koteliansky, A. G. Majouga, Tetrahedron Lett., 2016, 57: 5501.

    Article  CAS  Google Scholar 

  2. M. Zuo, X. Xu, Z. Xie, R. Ge, Z. Zhang, Z. Li, J. Bian, Eur. J. Med. Chem., 2017, 125: 1002.

    Article  CAS  PubMed  Google Scholar 

  3. A. I. El-Shenawy, Rus. J. Bioorg. Chem., 2016, 42: 100.

    Article  CAS  Google Scholar 

  4. J. Thanusu, V. Kanagarajan, M. Gopalakrishnan, Bioorg. Med. Chem. Lett., 2010, 20: 713.

    Article  CAS  PubMed  Google Scholar 

  5. F. Wu, H. Jiang, B. Zheng, M. Kogiso, Y. Yao, C. Zhou, X.-N. Li, Y. Song, J. Med. Chem., 2015, 58: 6899.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. G. A. Gazieva, Yu. B. Vikharev, L. V. Anikina, T. B. Karpova, A. N. Kravchenko, E. A. Permyakov, I. V. Svitanko, Mendeleev Commun., 2013, 23: 202.

    Article  CAS  Google Scholar 

  7. G. A. Gazieva, L. V. Anikina, S. A. Pukhov, T. B. Karpova, Yu. V. Nelyubina, A. N. Kravchenko, Mol. Divers., 2016, 20: 837.

    Article  CAS  PubMed  Google Scholar 

  8. G. A. Gazieva, L. V. Anikina, T. V. Nechaeva, S. A. Pukhov, T. B. Karpova, S. V. Popkov, Yu. V. Nelyubina, N. G. Kolotyrkina, A. N. Kravchenko, Eur. J. Med. Chem., 2017, 140: 141.

    Article  CAS  PubMed  Google Scholar 

  9. L. D. Porter, T. F. Cummings, D. A. Johnson, Plant Dis., 2006, 90: 964.

    Article  CAS  Google Scholar 

  10. M. W. Ding, Y. F. Chen, N. Y. Huang, Phosphorus, Sulfur, Silicon, Relat. Elem., 2004, 179: 2287.

    Article  CAS  Google Scholar 

  11. H. R. Kim, H. J. Lee, Y. J. Choi, Y. J. Park, Y. Woo, S. J. Kim, M. H. Park, H. W. Lee, P. Chun, H. Y. Chung, H. R. Moon, Med. Chem. Commun., 2014, 5: 1410.

    Article  CAS  Google Scholar 

  12. N. I. Vorozhtsov, L. A. Sviridova, O. S. Grigorkevich, D. D. Korablina, E. K. Beloglazkina, A. G. Majouga, N. V. Zyk, Russ. Chem. Bull., 2017, 66: 506.

    Article  CAS  Google Scholar 

  13. R. Mahmood, S. Ahmad, M. Fettouhi, T. Roisnel, M. A. Gilani, K. Mehmood, G. Murtaza, A. A. Isab, J. Mol. Struct., 2018, 1156: 235.

    Article  CAS  Google Scholar 

  14. K. I. Tishchenko, E. K. Beloglazkina, M. A. Proskurnin, A. G. Mazhuga, M. E. Muratova, D. A. Skvortsov, N. V. Zyk, Russ. Chem. Bull., 2016, 65: 1254.

    Article  CAS  Google Scholar 

  15. E. K. Beloglazkina, N. I. Vorozhtsov, L. A. Sviridova, O. S. Grigorkevich, D. D. Korablina, A. A. Moiseeva, N. V. Zyk, A. G. Majouga, Inorg. Chem. Commun., 2016, 71: 86.

    Article  CAS  Google Scholar 

  16. L. D. Popov, G. A. Gazieva, A. N. Kravchenko, Yu. N. Tkachenko, O. I. Askalepova, S. I. Levchenkov, T. B. Karpova, Yu. P. Tupolova, V. V. Lukov, V. A. Kogan, Russ. J. Gen. Chem., 2015, 85: 92.

    Article  CAS  Google Scholar 

  17. G. A. Gazieva, P. A. Poluboyarov, L. D. Popov, N. G. Kolotyrkina, A. N. Kravchenko, N. N. Makhova, Synthesis, 2012, 44: 3366.

    Article  CAS  Google Scholar 

  18. G. A. Gazieva, T. B. Karpova, L. D. Popov, Yu. V. Nelyubina, and A. N. Kravchenko, J. Heterocycl. Chem., 2015, 52: 1390.

    Article  CAS  Google Scholar 

  19. G. A. Gazieva, T. B. Karpova, T. V. Nechaeva, A. N. Kravchenko, Russ. Chem. Bull., 2016, 65: 2172.

    Article  CAS  Google Scholar 

  20. Metodicheskiye rekomendatsii po opredeleniyu fungitsidnoi aktivnosti novykh soedinenii [Guidelines for Determination of Fungicidal Activity of New Compounds], NIITEKHIM, Cherkassy, 1984, 32 p. (in Russian).

  21. S. V. Popkov, A. A. Makarenko, G. I. Nikishin, Russ. Chem. Bull., 2016, 65: 513.

    Article  CAS  Google Scholar 

  22. N. M. Golyshin, Fungicidy v selskom khozyaistve [Fungicides in the agriculture], Kolos, Moscow, 1970, 167 p. (in Russian).

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    G. A. Gazieva, N. N. Kostikova, N. V. Sigay & S. A. Serkov

  2. The State Scientific-Research Institute of Chemical Reagents and High Purity Chemical Substances, National Research Center “Kurchatov Institute”, 3 ul. Bogorodskiy Val, 107076, Moscow, Russian Federation

    T. V. Nechaeva

  3. D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    S. V. Popkov

Authors
  1. G. A. Gazieva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. T. V. Nechaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. N. Kostikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. V. Sigay
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. A. Serkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. S. V. Popkov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. A. Gazieva.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1059–1064, June, 2018.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gazieva, G.A., Nechaeva, T.V., Kostikova, N.N. et al. Synthesis, S-alkylation, and fungicidal activity of 4-(benzylideneamino)thioglycolurils. Russ Chem Bull 67, 1059–1064 (2018). https://doi.org/10.1007/s11172-018-2180-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-018-2180-x

Key words

Search

Navigation