Synthesis and Herbicidal and Antioxidant Activity of a Series of Hetero- and Carbocyclic Derivatives of Monochloroacetic Acid

Abstract

Monochloroacetic acid esters and amides containing carbo- and heterocycles and heterocyclic esters and amides derived from commercial aryloxyacetyl chlorides were synthesized. The structures of the compounds were confirmed by 1Н and 13С spectroscopy. The herbicidal activity of the substances was studied with respect to mono- and dicotyledonous plants. The relative antioxidant activity of the compounds was studied by recording the luminol-dependent chemiluminescence. The experimental data, on the whole, confirm that the development of herbicides containing acetal and gem-dichlorocyclopropane fragments is appropriate and promising.

This is a preview of subscription content, log in to check access.

Scheme
Scheme
Scheme
Scheme
Scheme

REFERENCES

  1. 1

    Ganiullina, E.R., Voronenko, B.I., Kuznetsov, V.M., Mazitov, R.M., Zlotskii, S.S., and Dekhtyar’, T.F., Bashk. Khim. Zh., 2008, vol. 15, no. 3, pp. 53–56.

    CAS  Google Scholar 

  2. 2

    Raskil’dina, G.Z., Borisova, Yu.G., Valiev, V.F., Mikhailova, N.N., Zlotskii, S.S., Zaikov, G.E., and Emelina, O.Yu., Vestn. Kazansk. Tekh. Univ., 2014, vol. 17, no. 15, pp. 166–169.

    Google Scholar 

  3. 3

    Kuznetsov, V.M., Bogomazova, A.A., Shiriazdano-va, A.R., Mikhailova, N.N., and Zlotskii, S.S., Bashk. Khim. Zh., 2010, vol. 17, no. 3, pp. 33–35.

    Google Scholar 

  4. 4

    Yakovenko, E.A., Bauburtli, A.V., and Raskil’dina, G.Z., Bashk. Khim. Zh., 2017, vol. 24, no. 2, pp. 52–56.

    CAS  Google Scholar 

  5. 5

    Yakovenko, E.A., Bulatova, Yu.I., Mirakyan, S.M., Valiev, V.F., Borisova, Yu.G., Mikhailova, N.N., and Raskil’dina, G.Z., Bashk. Khim. Zh., 2016, vol. 23, no. 4, pp. 94–98.

    CAS  Google Scholar 

  6. 6

    Timofeeva, S.A., Giniyatullina, E.Kh., Kuznetsov, V.M., Udalova, E.A., Shavshukova, S.Yu., and Zlotskii, S.S., Bashk. Khim. Zh., 2011, vol. 18, no. 3, pp. 71–73.

    CAS  Google Scholar 

  7. 7

    Kazakova, A.N., Kuznetsov, V.M., Musavirova, L.R., Mikhailova, N.N., Bogomazova, A.A., Mudrik, T.P., and Zlotskii, S.S., Bashk. Khim. Zh., 2013, vol. 20, no. 1, pp. 8–10.

    CAS  Google Scholar 

  8. 8

    Ganiev, M.M. and Nedorezkov, V.D., Khimicheskie sredstva zashchity rastenii (Chemical Agents for Plant Protection), Moscow: KolosS, 2006.

    Google Scholar 

  9. 9

    Grivennikova, V.G. and Vinogradov, A.D., Usp. Biol. Khim., 2013, vol. 53, pp. 245–296.

    Google Scholar 

  10. 10

    Koltover, V.K., Russ. Chem. Bull., 2010, vol. 59, no. 1, pp. 37–42.

    CAS  Article  Google Scholar 

  11. 11

    Burlakova, E.B. and Khrapova, N.G., Russ. Chem, Rev., 1985, vol. 54, pp. 907–917. https://doi.org/10.1070/RC1985v054n09ABEH003121

    Article  Google Scholar 

  12. 12

    Petrova, I.V., Kataev, V.A., Meshcheryakova, S.A., Nikolaeva, K.V., Munasipova, D.A., and Farkhutdi-nov, R.R., Med. Vestn. Bashk., 2013, vol. 8, no. 4, pp. 64–67.

    Google Scholar 

  13. 13

    Petrova, I.V., Kataev, V.A., Meshcheryakova, S.A., Nikolaeva, K.V., Munasipova, D.A., and Farkhutdinov, R.R., Med. Vestn. Bashk., 2013, vol. 8, no. 6, pp. 163–165.

    Google Scholar 

  14. 14

    Farkhutdinov, R.R., Procedures for studying chemiluminescence of a biological material on a KhL-003 chemiluminometer, Metody otsenki antioksidantnoi aktivnosti biologicheski aktivnykh veshchestv lechebnogo i profilakticheskogo naznacheniya: Sbornik dokladov (Methods for Evaluating the Antioxidant Activity of Biologically Active Compounds for Therapeutic and Prophylactic Purposes: Coll. of Reports), Moscow: Ross. Univ. Druzhby Narodov, 2005.

  15. 15

    Laletin, V.S. and Kolesnichenko, L.S., Sib. Khim. Zh., 2010, no. 1, pp. 72–74.

    Google Scholar 

  16. 16

    Vardanyan, R.L., Vardanyan, L.R., Airapetyan, S.A., Arutyunyan, L.R., and Arutyunyan, R.S., Khim. Rast. Syr’ya, 2015, no. 1, pp. 113–119. https://doi.org/10.14258/10.14258/jcprm.201501295

    Article  Google Scholar 

  17. 17

    Uzbekov, M.G., Sots. Klin. Psikhiatr., 2014, vol. 24, no. 4, pp. 97–103.

    Google Scholar 

Download references

ACKNOWLEDGMENTS

The authors are sincerely grateful to L.V. Spirikhin, head of Laboratory of Physicochemical Methods of Analysis, Ufa Federal Research Center, Russian Academy of Sciences, for the assistance in identification of the structures of the compounds.

Funding

The studies were supported by the Russian Foundation for Basic Research, mol_ev_a competition (Eureca! Idea), contract no. 19-33-80002\19 of December 7, 2018.

Author information

Affiliations

Authors

Corresponding author

Correspondence to G. Z. Raskil’dina.

Ethics declarations

The authors declare that they have no conflict of interest.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Yakovenko, E.A., Baimurzina, Y.L., Raskil’dina, G.Z. et al. Synthesis and Herbicidal and Antioxidant Activity of a Series of Hetero- and Carbocyclic Derivatives of Monochloroacetic Acid. Russ J Appl Chem 93, 712–720 (2020). https://doi.org/10.1134/S1070427220050122

Download citation

Keywords:

  • amines
  • monochloroacetic acid esters and amines
  • cyclic acetal and gem-dichlorocyclopropane fragments
  • herbicidal and antioxidant activity