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Synthesis of New Bis(arylsulfanyl Diketones) as Promising Building Blocks with Fungicidal Activity

  • Organic Synthesis and Industrial Organic Chemistry
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An Erratum to this article was published on 01 June 2023

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Abstract

A procedure was developed for preparing block synthons by the reaction of 2,4-pentanedione, 1,2-ethanedithiol, and aromatic aldehydes in the presence of an organic catalyst (triethylamine, piperidine, diazabicycloundecene, morpholine) to construct heterocycles derived from bis(arylmethylsulfanyl diketones). Among the bis(sulfanyl diketones) prepared, the compounds containing p-methoxyphenyl and thienyl substituents in the methinesulfanyl moiety showed the highest fungicidal activity toward phytopathogenic fungi Bipolaris sorokiniana, Fusarium oxysporum, and Rhizoctonia solani.

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REFERENCES

  1. Margalef, J. and Samec, J.S.M., ChemSusChem, 2021, vol. 14, no. 3, pp. 808–823. https://doi.org/10.1002/cssc.202002409

    Article  CAS  PubMed  Google Scholar 

  2. Akhmetova, V.R., Akhmadiev, N.S., Starikova, Z.A., Tulyabaev, A.R., Mescheryakova, E.S., and Ibragimov, A.G., Tetrahedron, 2015, vol. 71, no. 40, pp. 7722–7728. https://doi.org/10.1016/j.tet.2015.07.055

    Article  CAS  Google Scholar 

  3. Akhmetova, V.R., Akhmadiev, N.S., Meshcheryakova, E.S., Khalilov, L.M., and Ibragimov, A.G., Chem. Heterocycl. Compd., 2014, vol. 50, pp. 742–751. https://doi.org/10.1007/s10593-014-1529-9

    Article  CAS  Google Scholar 

  4. Li, L., Bokai, L., Qi, W., and Xianfu, L., Chin. J. Chem., 2011, vol. 29, no. 9, pp. 1856–1862. https://doi.org/10.1002/cjoc.201180324

    Article  CAS  Google Scholar 

  5. Ma, X., Zhang, M., Wang, B., and Min, F., Phosphorus, Sulfur Silicon Relat. Elem., 2015, vol. 190, pp. 1108–1114. https://doi.org/10.1080/10426507.2014.974091

    Article  CAS  Google Scholar 

  6. Dar, A.A., Enjamuri, N., Shadab, Md., Ali, N., and Khan, A.T., ACS Comb. Sci., 2015, vol. 17, no. 11, pp. 671–681. https://doi.org/10.1021/acscombsci.5b00044

    Article  CAS  PubMed  Google Scholar 

  7. Chen, Q., Wang, X., Wen, C., Huang, Y., Yan, X., and Zeng, J., RSC Adv., 2017, vol. 7, pp. 39758–39761. https://doi.org/10.1039/C7RA06904A

    Article  CAS  Google Scholar 

  8. Jimeno, C., Org. Biomol. Chem., 2016, vol. 14, pp. 6147–6164. https://doi.org/10.1039/C6OB00783J

    Article  CAS  PubMed  Google Scholar 

  9. Akhmadiev, N.S., Akhmetova, V.R., Boiko, T.F., and Ibragimov, A.G., Chem. Heterocycl. Compd., 2018, vol. 54, pp. 344–350. https://doi.org/10.1007/s10593-018-2271-5

    Article  CAS  Google Scholar 

  10. Ragavan, R.V., Vijayakumar, V., and Kumari, N.S., Eur. J. Med. Chem., 2009, vol. 44, pp. 3852–3857. https://doi.org/10.1016/j.ejmech.2009.04.010

    Article  CAS  Google Scholar 

  11. Akhmetova, V.R., Galimova, R.A., Akhmadiev, N.S., Galimova, A.M., Khisamutdinov, R.A., Nurtdinova, G.M., Agletdinov, E.F., and Kataev, V.A., Adv. Pharm. Bull., 2018, vol. 8, no. 2, pp. 267–275. https://doi.org/10.15171/apb.2018.031

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. Diversity-Oriented Synthesis: Basics and Applications in Organic Synthesis, Drug Discovery, and Chemical Biology, Trabocchi, A., Ed., Wiley, 2013, pp. 1–26.

    Google Scholar 

  13. Tietze, L.-F. and Eicher, T., Reactions and Syntheses in the Organic Chemistry Laboratory, New York: Wiley, 1986.

    Google Scholar 

  14. Isagulyants, V.I., Sinteticheskie dushistye veshchestva (Synthetic Fragrant Substances), Yerevan: Akad. Nauk Arm. SSR, 1946.

    Google Scholar 

  15. Bonev, B., Hooper, J., and Parisot, J., Antimicrob. Chemother., 2008, vol. 61, no. 6, pp. 1295–1301. https://doi.org/10.1093/jac/dkn090

    Article  CAS  Google Scholar 

  16. Baeva, L.A., Biktasheva, L.F., Fatykhov, A.A., and Galimzyanova, N.F., Russ. J. Appl. Chem., 2022, vol. 95, pp. 1030–1035. https://doi.org/10.1134/S1070427222070151

    Article  CAS  Google Scholar 

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Funding

The interdisciplinary study was performed in accordance with the research plan of the Institute of Petroleum Chemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences (FMRS-2022-0074 and FMRS-2022-0079) and within the framework of the government assignment of the Ministry of Science and Higher Education of the Russian Federation no. 075032021607, theme no. 122031100163-4, using the equipment of the Agidel Center for Shared Use, Ufa Federal Research Center, Russian Academy of Sciences.

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Authors and Affiliations

Authors

Contributions

N.S. Akhmadiev: experiments on synthesis, isolation, and identification of the desired bis(arylsulfanyl diketones); N.F. Galimzyanova: experiments on primary screening of the compounds synthesized for fungicidal activity; V.R. Akhmetova: task setting and discussion of the results.

Corresponding author

Correspondence to V. R. Akhmetova.

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The authors declare that they have no conflicts of interest.

Additional information

Translated from Zhurnal Prikladnoi Khimii, No. 5, pp. 528–536, August, 2023 https://doi.org/10.31857/S0044461823050029

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Akhmadiev, N.S., Galimzyanova, N.F. & Akhmetova, V.R. Synthesis of New Bis(arylsulfanyl Diketones) as Promising Building Blocks with Fungicidal Activity. Russ J Appl Chem 96, 594–601 (2023). https://doi.org/10.1134/S1070427223050129

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  • DOI: https://doi.org/10.1134/S1070427223050129

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