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NaSCN–(NH4)2Ce(NO3)6 system in heterocycle thiocyanation: synthesis of novel highly potent broad-spectrum fungicides for crop protection

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Chemistry of Heterocyclic Compounds Aims and scope

A method for thiocyanation of pyrroles, indoles, pyrazolones, and pyrimidine-2,4,6-triones with the NaSCN–(NH4)2Ce(NO3)6 system was proposed. The most important result was the synthesis of dithiocyanated pyrroles with high fungicidal activity against various phytopathogenic fungi.

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References

  1. (a) Romanowski, F.; Klenk, H. In Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH, Ed.; Wiley-VCH: Weinheim, 2000, Vol. 36, p. 609. (b) Castanheiro, T.; Suffert, J.; Donnard, M.; Gulea, M. Chem. Soc. Rev. 2016, 45, 494. (c) Nikoofar, K. Chem. Sci. Trans. 2013, 2, 691.

  2. (a) Grove, J. F.; Bovington, H. H. S. Ann. Appl. Biol. 1947, 34, 113. (b) Murphy, D. F.; Peet, C. H. Ind. Eng. Chem. 1933, 25, 638.

  3. (a) Kokorekin, V. A.; Terent'ev, A. O.; Ramenskaya, G. V.; Grammatikova, N. É.; Rodionova, G. M.; Ilovaiskii, A. I. Pharm. Chem. J. 2013, 47, 422. [Khim.-Farm. Zh. 2013, 47(8), 26.] (b) Akerstrom, S. H. J. US Patent 3663701. b Terent'ev, A. O.; Kokorekin, V. A.; Petrosyan, V. A.; Grammatikova, N. E. RU Patent 2523012. c Romagnoli, C.; Vicentini, C. B.; Mares, D. Lett. Appl. Microbiol. 1995, 20, 5. d Vannini, G. L.; Dall'Olio, G.; Giori, P. Mycopathologia 1976, 59, N1. e Yaubasarova, R. R.; Kokorekin, V. A.; Ramenskaya, G. V.; Petrosyan, V. A. Mendeleev Commun. 2019, 29, 334.

  4. (a) James, N. R.; Jayakrishnan, A. Biomaterials 2003, 24, 2205. (b) Kameda, T.; Ono, M.; Grause, G.; Mizoguchi, T.; Yoshioka, T. J. Polym. Res. 2011, 18, 945.

  5. Fortes, M. P.; da Silva, P. B. N.; da Silva, T. G.; Kaufman, T. S.; Militão, G. C. G.; Silveira, C. C. Eur. J. Med. Chem. 2016, 118, 21.

    Article  CAS  Google Scholar 

  6. (a) Sae-oui, P.; Sirisinha, C.; Thepsuwan, U.; Hatthapanit, K. Eur. Polym. J. 2006, 42, 479. (b) Dishovski, N.; Mitkova, F.; Kandeva, M.; Angelov, Y.; Uzunov, I.; Ivanov, M.; Klissurski, D. Mater. Sci. Appl. 2018, 9, 412.

  7. N. V. Philips' Gloeilampenfabrieken NL Patent 6617755.

  8. Söderbäck, E. Acta Chem. Scand. 1954, 8, 1851.

    Article  Google Scholar 

  9. Wu, G.; Liu, Q.; Shen, Y.; Wu, W.; Wu, L. Tetrahedron Lett. 2005, 46, 5831.

    Article  CAS  Google Scholar 

  10. Khalili, D. New J. Chem. 2016, 40, 2547.

    Article  CAS  Google Scholar 

  11. Iranpoor, N.; Firouzabadi, H.; Khalili, D.; Shahin, R. Tetrahedron Lett. 2010, 51, 3508.

    Article  CAS  Google Scholar 

  12. Khalili, D. Chin. Chem. Lett. 2015, 26, 547.

    Article  CAS  Google Scholar 

  13. Iranpoor, N.; Firouzabadi, H.; Shahin, R.; Khalili, D. Synth. Commun. 2012, 42, 2040.

    Article  CAS  Google Scholar 

  14. Venkatesham, N.; Rajendar Reddy, K.; Rajanna, K. C.; Veerasomaiah, P. J. Sulfur Chem. 2014, 35, 606.

    Article  CAS  Google Scholar 

  15. Yadav, J. S.; Reddy, B. V. S.; Shubashree, S.; Sadashiv, K. Tetrahedron Lett. 2004, 45, 2951.

    Article  CAS  Google Scholar 

  16. Zhang, X.; Wang, C.; Jiang, H.; Sun, L. RSC Adv. 2018, 8, 22042.

    Article  CAS  Google Scholar 

  17. (a) Memarian, H. R.; Mohammadpoor-Baltork, I.; Nikoofar, K. Can. J. Chem. 2007, 85, 930. (b) Memarian, H. R.; Mohammadpoor-Baltork, I.; Nikoofar, K. Ultrason. Sonochem. 2008, 15, 456.

  18. Nair, V.; George, T. G.; Nair, L. G.; Panicker, S. B. Tetrahedron Lett. 1999, 40, 1195.

    Article  CAS  Google Scholar 

  19. (a) Nair, V.; Nair, L. G. Tetrahedron Lett. 1998, 39, 4585. (b) Nair, V.; Nair, L. G.; George, T. G.; Augustine, A. Tetrahedron 2000, 56, 7607.

  20. Kumar, A.; Pathak, S. R. Lett. Org. Chem. 2005, 2, 745.

    Article  CAS  Google Scholar 

  21. Terent'ev, A. O.; Sharipov, M. Yu.; Glinuskin, A. P.; Krylov, I. B.; Gaidarenko, D. V.; Nikishin, G. I. Mendeleev Commun. 2016, 26, 226.

    Article  CAS  Google Scholar 

  22. Jiao, J.; Nguyen, L. X.; Patterson, D. R.; Flowers, R. A. Org. Lett. 2007, 9, 1323.

    Article  CAS  Google Scholar 

  23. (a) Bellomo, A.; Gonzalez, D. Tetrahedron Lett. 2007, 48, 3047. (b) Blake, A. J.; Cooke, P. A.; Kendall, J. D.; Simpkins, N. S.; Westaway, S. M. J. Chem. Soc., Perkin Trans. 1 2000, 153.

  24. (a) Cataldo, F. Polyhedron 2000, 19, 681. (b) Burchell, C. J.; Kilian, P.; Slawin, A. M. Z.; Woollins, J. D.; Tersago, K.; Van Alsenoy, C.; Blockhuys, F. Inorg. Chem. 2006, 45, 710. (c) Vanderzee, C. E.; Quist, A. S. Inorg. Chem. 1966, 5, 1238. (d) Lambou, M. G.; Dollear, F. G. Oil Soap 1945, 22, 226. (e) Gardner, W. H.; Weinberger, H.; Englis, D. T.; Price, E. C. In Inorganic Syntheses; Booth, H. S., Ed.; John Wiley & Sons: Hoboken, 2007, Vol. 1, p. 84.

  25. Kokorekin, V. A.; Mel'nikova, E. I.; Yaubasarova, R. R.; Gorpinchenko, N. V.; Petrosyan, V. A. Russ. Chem. Bull., Int. Ed. 2019, 68, 2140. [Izv. Akad. Nauk, Ser. Khim. 2019, 2140.]

  26. Sridharan, V.; Menéndez, J. C. Chem. Rev. 2010, 110, 3805.

    Article  CAS  Google Scholar 

  27. (a) Rezayati, S.; Ramazani, A. Tetrahedron 2020, 76, 131382. (b) Kokorekin, V. A.; Yaubasarova, R. R.; Neverov, S. V.; Petrosyan, V. A. Eur. J. Org. Chem. 2019, 4233. (c) Gitkis, A.; Becker, J. Y. J. Electroanal. Chem. 2006, 593, 29.

  28. Mikhailovskii, A. G.; Peretyagin, D. A. Russ. J. Org. Chem. 2018, 54, 1815. [Zh. Org. Khim. 2018, 54, 1801.]

  29. (a) Krylov, I. B.; Paveliev, S. A.; Shelimov, B. N.; Lokshin, B. V.; Garbuzova, I. A.; Tafeenko, V. A.; Chernyshev, V. V.; Budnikov, A. S.; Nikishin, G. I.; Terent'ev, A. O. Org. Chem. Front. 2017, 4, 1947. (b) Krylov, I. B.; Budnikov, A. S.; Lopat'eva, E. R.; Nikishin, G. I.; Terent'ev, A. O. Chem.–Eur. J. 2019, 25, 5922.

  30. Metodicheskie Rekomendatsii po Opredeleniyu Fungitsidnoi Aktivnosti Novykh Soedinenii (Guidelines for Determination of Fungicidal Activity of New Compounds [In Russian]); Cherkassy: NIITEKhIM, 1984.

  31. (a) Popkov, S. V.; Kovalenko, L. V.; Bobylev, M. M.; Molchanov, O. Yu.; Krimer, M. Z.; Tashchi, V. P.; Putsykin, Y. G. Pestic. Sci. 1997, 49, 125. (b) Itoh, H.; Kajino, H.; Tsukiyama, T.; Tobitsuka, J.; Ohta, H.; Takahi, Y.; Tsuda, M.; Takeshiba, H. Bioorg. Med. Chem. 2002, 10, 4029. (c) Xu, H.; Fan, L. Eur. J. Med. Chem. 2011, 46, 364. (d) Singh, P. K. J. Agric. Food Chem. 2012, 60, 5813. (e) Pan, L.; Li, X.; Gong, C.; Jin, H.; Qin, B. Microb. Pathog. 2016, 95, 186.

  32. Huang, K.-L.; Chen, T.-S.; Tsai, R.-W.; Chen, Y.-S. Clean Technol. Environ. Policy 2016, 18, 1043.

    Article  CAS  Google Scholar 

  33. (a) Belyakov, P. A.; Kadentsev, V. I.; Chizhov, A. O.; Kolotyrkina, N. G.; Shashkov, A. S.; Ananikov, V. P. Mendeleev Commun. 2010, 20, 125. (b) Kachala, V. V.; Khemchyan, L. L.; Kashin, A. S.; Orlov, N. V.; Grachev, A. A.; Zalesskiy, S. S.; Ananikov, V. P. Russ. Chem. Rev. 2013, 82, 648.

  34. Heaney, H.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1973, 499.

  35. D’Silva, C.; Walker, D. A. J. Org. Chem. 1998, 63, 6715.

    Article  Google Scholar 

  36. Jursic, B. S.; Stevens, E. D. Tetrahedron Lett. 2003, 44, 2203.

    Article  CAS  Google Scholar 

  37. (a) Zhang, W.; Tang, J.; Yu, W.; Huang, Q.; Fu, Y.; Kuang, G.-C.; Pan, C.; Yu, G. ACS Catal. 2018, 8, 8084. (b) Wang, L.; Wang, C.; Liu, W.; Chen, Q.; He, M. Tetrahedron Lett. 2016, 57, 1771.

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This work was supported by the Russian Science Foundation (grant 19-73-20190).

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Authors and Affiliations

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

    Mikhail Yu. Sharipov, Igor B. Krylov & Alexander O. Terent’ev

  2. D. Mendeleyev University of Chemical Technology of Russia, 9 Miusskaya Sq, Moscow, 125047, Russia

    Mikhail Yu. Sharipov, Igor B. Krylov, Ivan D. Karpov, Olga V. Vasilkova, Anna-Maria V. Oleksiienko & Alexander O. Terent’ev

  3. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky Ave, Moscow, 119991, Russia

    Mikhail Yu. Sharipov, Ivan D. Karpov, Olga V. Vasilkova & Anna-Maria V. Oleksiienko

  4. State Scientific Institution “All-Russian Research Institute of Phytopathology”, Possesion 5, Institute St., Bolshie Vyazemy, 143050, Odintsovo distr, Moskow reg, Russia

    Igor B. Krylov & Alexander O. Terent’ev

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  1. Mikhail Yu. Sharipov
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  2. Igor B. Krylov
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  3. Ivan D. Karpov
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  4. Olga V. Vasilkova
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  5. Anna-Maria V. Oleksiienko
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  6. Alexander O. Terent’ev
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Correspondence to Igor B. Krylov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(5), 531–537

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Sharipov, M.Y., Krylov, I.B., Karpov, I.D. et al. NaSCN–(NH4)2Ce(NO3)6 system in heterocycle thiocyanation: synthesis of novel highly potent broad-spectrum fungicides for crop protection. Chem Heterocycl Comp 57, 531–537 (2021). https://doi.org/10.1007/s10593-021-02938-y

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