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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 1, pp 31–37 | Cite as

Synthesis and fungicidal activity of methylsulfanylmethyl ether derivatives of levoglucosenone

  • Bulat T. SharipovEmail author
  • Anna N. Davidova
  • Alena S. Ryabova
  • Nailya F. Galimzyanova
  • Farid A. Valeev
Article

A series of derivatives were synthesized on the basis of levoglucosenone that contained hydroxy groups at the С-4 atom or С-2 and С-4 atoms or a hydroxy and methyl group at the С-4 atom. In addition, 4-hydroxymethylbutanolides were synthesized. Derivatives containing hydroxy groups were obtained as methylsulfanylmethyl ethers. It was established that compounds containing a 6,8-dioxabicyclo[3.2.1]-octane ring exhibited fungicidal activity against Rhizoctonia solani. It was shown that the presence of a methylsulfanylmethyl moiety in the ring could increase the fungicidal activity of compounds.

Keywords

γ-butanolides levoglucosenone methylthiomethyl ethers fungicidal activity Rhizoctonia solani 

Notes

The work was performed according to the State contracts No. АААА-А17-117011910022-5, АААА-А18-118022190098-9) and with financial support from the Russian Foundation for Basic Research (grant 17-43-020166 r_a).

Analytical support was provided using equipment at the Collective Use Center “Chemistry” of the Institute of Chemistry, Ufa Federal Research Center of the Russian Academy of Sciences.

Supplementary material

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ESM 1 (PDF 1105 kb)

References

  1. 1.
    (a) Miftakhov, M. S.; Valeev, F. A.; Gaisina, I. N. Russ. Chem. Rev. 1994, 63, 869. [Usp. Khim. 1994, 63, 922.] (b) Sarotti, A. M.; Zanardi, M. M.; Spanevello, R. A.; Suárez, A. G. Curr. Org. Synth. 2012, 9, 439. b Comba, M. B.; Tsai, Y-h.; Sarotti, A. M.; Mangione, M. I.; Suárez, A. G.; Spanevello, R. A. Eur. J. Org. Chem. 2018, 590.Google Scholar
  2. 2.
    (a) Matsumoto, K.; Ebata, T.; Koseki, K.; Kawakami, H.; Matsushita, H. Bull. Chem. Soc. Jpn. 1991, 64, 2309. (b) Matsumoto, K.; Ebata, T.; Koseki, K.; Kawakami, H.; Matsushita, H. Heterocycles 1991, 32, 2225.Google Scholar
  3. 3.
    (a) Kuno, H.; Niihata, S.; Ebata, T.; Matsushita, H. Heterocycles 1995, 41, 523. (b) Jung, M. E.; Kiankarimi, M. J. Org. Chem. 1998, 63, 8133.Google Scholar
  4. 4.
    Ebata, T.; Matsumoto, K.; Yoshikoshi, H.; Koseki, K.; Kawakami, H.; Matsushita, H. Heterocycles 1990, 31, 1585.CrossRefGoogle Scholar
  5. 5.
    (a) Valeev, F. A.; Gorobets, E. V.; Tsypysheva, I. P.; Singizova, G. Sh.; Kalimullina, L. Kh.; Safarov, M. G.; Shitikova, O. V.; Miftakhov, M. S. Chem. Nat. Compd. 2003, 39, 563. [Khim. Prirod. Soedin. 2003, 39, 465.] (b) Mori, M.; Chuman, T.; Kato, K.; Mori, K. Tetrahedron Lett. 1982, 23, 4593. b Witczak, Z. J.; Li, Y. Tetrahedron Lett. 1995, 36, 2595.Google Scholar
  6. 6.
    Tolstikov, G. A.; Valeev, F. A.; Gaisina, I. N.; Spirikhin, L. V.; Miftakhov, M. S. J. Org. Chem. USSR 1992, 28, 1659. [Zh. Org. Khim. 1992, 28, 2072.]Google Scholar
  7. 7.
    (a) Witczak, Z. J.; Kaplon, P.; Dey, P. M. Carbohydr. Res. 2003, 338, 11. (b) Czubatka-Bieńkowska, A.; Sarnik, J.; Macieja, A.; Galita, G.; Witczak, Z. J.; Poplawski, T. Bioorg. Med. Chem. Lett. 2017, 27, 2713. (c) Giri, G. F.; Danielli, M.; Marinelli, R. A.; Spanevello, R. A. Bioorg. Med. Chem. Lett. 2016, 26, 3955.Google Scholar
  8. 8.
    Giri, G. F.; Viarengo, G.; Furlán, R. L. E.; Suárez, A. G.; Garcia Véscovi, E.; Spanevello, R. A. Ind. Crops Prod. 2017, 105, 113.CrossRefGoogle Scholar
  9. 9.
    Henzell, R. F.; Furneaux, R. H.; Tyler, P. C. Pestic. Sci. 1990, 30, 59.CrossRefGoogle Scholar
  10. 10.
    (а) Court, G. R.; Lawrence, C. H.; Raverty, W. D.; Duncan, A. J. US Patent US20120111714. a Alves Costa Pacheco, A.; Sherwood, J.; Zhenova, A.; McElroy, C. R.; Hunt, A. J.; Parker, H. L.; Farmer, T. J.; Constantinou, A.; De bruyn, M.; Whitwood, A. C.; Raverty, W.; Clark, J. H. ChemSusChem 2016. 9. 3503.Google Scholar
  11. 11.
    (a) Sherwood, J.; De bruyn, M.; Constantinou, A.; Moity, L.; McElroy, C. R.; Farmer, T. J.; Duncan, T.; Raverty, W.; Hunta A. J.; Clark, J. H. Chem. Commun. 2014, 50, 9650. (b) Shafizadeh, F.; Chin, P. S. Carbohydr. Res. 1977, 58, 79.Google Scholar
  12. 12.
    Shafizadeh, F.; Furneaux, R. H.; Stevenson, T. T. Carbohydr. Res. 1979, 71,169.CrossRefGoogle Scholar
  13. 13.
    (a) Fantin, G.; Fogagnolo, M.; Guerzoni, M. E.; Medici, A.; Pedrini, P.; Poli, S. J. Org. Chem. 1994, 59, 924. (b) Inoue, T.; Hosomi, K.; Araki, M.; Nishide, K.; Node, M. Tetrahedron: Asymmetry 1995, 6, 31.Google Scholar
  14. 14.
    Davydova, A. N.; Sharipov, B. T.; Valeev, F. A. Russ. J. Org. Chem. 2015 , 51, 1408. [Zh. Org. Khim. 2015, 51, 1440.]Google Scholar
  15. 15.
    Tsypysheva, I. P.; Valeev, F. A.; Vasil'eva, E. V.; Spirikhin, L. V.; Tolstikov, G. A. Russ. Chem. Bull., Int. Ed. 2000, 49, 1237. [Izv. Akad. Nauk, Ser. Khim. 2000, 1240.]CrossRefGoogle Scholar
  16. 16.
    (a) Koseki, K.; Ebata, T.; Kawakami, H.; Matsushita, H.; Naoi, Y.; Itoh, K. Heterocycles 1990, 31, 423. (b) Paris, C.; Moliner, M.; Corma, A. Green Chem. 2013, 15, 2101. (c) Flourat, A. L.; Peru, A. A. M.; Teixeira, A. R. S.; Brunissena, F.; Allais, F. Green Chem. 2015, 17, 404.Google Scholar
  17. 17.
    Davydova, A. N.; Pershin, A. A.; Sharipov, B. T.; Valeev, F. A. Mendeleev Commun. 2015, 25, 271.CrossRefGoogle Scholar
  18. 18.
    Vamos, M.; Kobayashi, Y. Tetrahedron 2009, 65, 5899.CrossRefGoogle Scholar
  19. 19.
    Pojer, P. M.; Angyal, S. J. Aust. J. Chem. 1978, 31, 1031.CrossRefGoogle Scholar
  20. 20.
    Medina, J. C.; Salomon, M.; Kyler, K. S. Tetrahedron Lett. 1988, 29, 3773.CrossRefGoogle Scholar
  21. 21.
    Rimmer, D. A.; Rose, M. E. J. Chromatogr. A. 1992, 598, 251.CrossRefGoogle Scholar
  22. 22.
    Halbych, J.; Trnka, T.; Černý, M. Collect. Сzech. Chem. Commun. 1973, 38, 2151.CrossRefGoogle Scholar
  23. 23.
    Trnka, T.; Černý, M. Collect. Czech. Chem. Commun. 1972, 37, 3632.CrossRefGoogle Scholar
  24. 24.
    Pratt, J. W.; Richtmyer, N. K. J. Am. Chem. Soc. 1957, 79, 2597.CrossRefGoogle Scholar
  25. 25.
    Bonev, B.; Hooper, J.; Parisot, J. J. Antimicrob. Chemother. 2008, 61, 1295.CrossRefPubMedGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Bulat T. Sharipov
    • 1
    Email author
  • Anna N. Davidova
    • 1
  • Alena S. Ryabova
    • 2
  • Nailya F. Galimzyanova
    • 2
  • Farid A. Valeev
    • 1
  1. 1.Ufa Institute of ChemistryRussian Academy of SciencesUfaRussia
  2. 2.Ufa Institute of BiologyRussian Academy of SciencesUfaRussia

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