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Synthesis and fungicidal activity of methylsulfanylmethyl ether derivatives of levoglucosenone

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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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.

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Authors and Affiliations

  1. Ufa Institute of Chemistry, Russian Academy of Sciences, 71 Oktyabrya Ave., Ufa, 450054, Russia

    Bulat T. Sharipov, Anna N. Davidova & Farid A. Valeev

  2. Ufa Institute of Biology, Russian Academy of Sciences, 69 Oktyabrya Ave., Ufa, 450054, Russia

    Alena S. Ryabova & Nailya F. Galimzyanova

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  1. Bulat T. Sharipov
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  2. Anna N. Davidova
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  3. Alena S. Ryabova
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  4. Nailya F. Galimzyanova
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  5. Farid A. Valeev
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Correspondence to Bulat T. Sharipov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(1), 31–37

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Sharipov, B.T., Davidova, A.N., Ryabova, A.S. et al. Synthesis and fungicidal activity of methylsulfanylmethyl ether derivatives of levoglucosenone. Chem Heterocycl Comp 55, 31–37 (2019). https://doi.org/10.1007/s10593-019-02415-7

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