The Synthesis of 1-Alkyl-3-polyfluoroalkyl- 1,3-dihydrobenzimidazole-2-selenones as Potential Plant Growth Regulators

Authors

  • Kirill I. Petko Institute of Organic Chemistry of the National Academy of Sciences of Ukraine, Ukraine https://orcid.org/0000-0002-2522-0128
  • Volodymyr S. Petrenko Institute of Organic Chemistry of the National Academy of Sciences of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.23.278660

Keywords:

N-polyfluoroalkylazoles, benzimidazole-2-selenones, plant growth regulation

Abstract

Aim. To synthesize new 1-alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones and study their biological activity as potential plant growth regulators.
Results and discussion. 1-Alkyl-3-polyfluoroalkyl-1,3-dihydrobenzimidazole-2-selenones were obtained from the corresponding 1-alkyl-3-polyfluoroalkylbenzimidazolium iodides by the action of elemental selenium in the presence of a base. The preliminary biological tests for the growth-regulating activity of the compounds obtained were conducted.
Experimental part. The structure of the compounds synthesized was proven by 1H and 19F NMR spectroscopy methods, as well as by the elemental analysis. The biological studies were done on model plants of winter wheat of the “bezosta” variety.
Conclusions. A convenient method for obtaining 1-alkyl-3-polyfluoroalkyl-1,3-dihydro-benzimidazole-2-selenones has been developed. Biological studies have shown that the compounds synthesized have a diverse effect on the plant growth.

Supporting Agency

  • The authors received no specific funding for this work

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References

  1. Stadtman, T. C., Selenium-Dependent Enzymes. Annu. Rev. Biochem. 1980, 49 (1), 93-110. https://doi.org/10.1146/annurev.bi.49.070180.000521.
  2. Sliwkowski, M. X.; Stadtman, T. C. Incorporation and distribution of selenium into thiolase from Clostridium kluyveri. Journal of biological chemistry 1985, 260 (5), 3140-3144. https://doi.org/10.1016/S0021-9258(18)89484-4.
  3. Saelinger, D. A.; Hoffman, J. L.; McConnell, K. P. Biosynthesis of selenobases in transfer RNA by Escherichia coli. J. Mol. Biol. 1972, 69 (1), 9-17. https://doi.org/10.1016/0022-2836(72)90020-4.
  4. Wittwer, A. J.; Tsai, L.; Ching, W. M.; Stadtman, T. C. Identification and synthesis of a naturally occurring selenonucleoside in bacterial tRNAs: 5-[(methylamino)methyl]-2-selenouridine. Biochemistry 1984, 23 (20), 4650-4655. https://doi.org/10.1021/bi00315a021.
  5. Carvalho, K. M.; Gallardo-Williams, M. T.; Benson, R. F.; Martin, D. F. Effects of Selenium Supplementation on Four Agricultural Crops. J. Agric. Food Chem. 2003, 51 (3), 704-709. https://doi.org/10.1021/jf0258555.
  6. Shanker, A. K. Countering UV-B Stress in Plants: Does Selenium have a Role? Plant Soil 2006, 282 (1), 21-26. https://doi.org/10.1007/s11104-005-5249-x.
  7. Finley, J. W. Selenium Accumulation in Plant Foods. Nutrition Reviews 2005, 63 (6), 196-202. https://doi.org/10.1111/j.1753-4887.2005.tb00137.x.
  8. Yagupolskii, L. M.; Sokolenko, T. M.; Petko, K. I. Chemical properties of N-polyfluoroethylimidazole and -pyrrole derivatives. Russ. Chem. Bull. 2005, 54 (3), 796-802. https://doi.org/10.1007/s11172-005-0323-3.
  9. Poludnenko, V. G.; Didinskaya, O. B.; Pozharskii, A. F. Fluorine-containing azoles. 2. Reaction of imidazole, benzimidazoles, and perimidines with difluorocarbene. Chem. Heterocycl. Comp. 1984, 20 (4), 422-425. https://doi.org/10.1007/BF00513860.
  10. Petko, K. I.; Yagupolskii, L. M. Interaction of the Azole N‐Sodium Derivatives with Freon‐113: Synthesis of N‐(2,2‐dichlorotrifluoroethyl)azoles. Synth. Commun. 2006, 36 (14), 1967-1972. https://doi.org/10.1080/00397910600634050.
  11. Sergeeva, Т. А. Metodika laboratornyih ispyitaniy gerbitsidov [Herbicide Laboratory Testing Procedure, in Russian]. Zaschita Rastenii 1963, 2, 42-43.
  12. Petrenko, V. S.; Danilenko, G. І.; Yavorovskii, P. P.; Schwartau, V. V.; Lysenko V. P.; Guzhova, S. V.; Ozerova, L. V.; Lozinskii, М. О. Norborn-5-en-2-karboksy-3-karboksylat 1-oksyd-2,6-dymetylpirydynu (Ivinor) – stymuliator rostu ta rozvytku roslyn [Norbon-5-en-2-carboxy-3-carboxylate 1-oxide-2,6-dimethylpyridine (Ivinor) plants growth and evolution stimulant, in Ukrainan]. UA Patent № 75280, Mar 15, 2006.

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Published

2023-08-30

How to Cite

(1)
Petko, K. I.; Petrenko, V. S. The Synthesis of 1-Alkyl-3-Polyfluoroalkyl- 1,3-Dihydrobenzimidazole-2-Selenones As Potential Plant Growth Regulators. J. Org. Pharm. Chem. 2023, 21, 10-14.

Issue

Vol. 21 No. 2 (2023)

Section

Original Researches

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