EVALUATION OF THE EFFECTIVENESS OF THE USE OF (PYRIDIN-4-YL)OXY SUBSTITUTED IMIDAZO[2,1-b][1,3]THIAZINES AS GROWTH INHIBITORS OF CUCUMIS SATIVUS

Authors

DOI:

https://doi.org/10.32782/pcsd-2023-3-5

Keywords:

6-[(pyridin-4-yl)oxy]-2,3-diphenyl-6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazines, 3-[(pyridin-4-yl)oxy]- 3,4-dihydro-2H-benzo[4,5]imidazo[2,1-b][1,3]thiazines, Cucumis sativus plants, growth inhibitory activity

Abstract

In this work, the rust-inhibiting effect of new pyridine-substituted imidazo[2,1-b][1,3]thiazines was investigated. Model objects 6-[(pyridin-4-yl)oxy]-2,3-diphenyl-6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine 3a and 3-[ (pyridin-4-yl)oxy]-3,4-dihydro-2H-benzo[4,5]imidazo[2,1-b][1,3]thiazines 3b-d were synthesized by the interaction of 3-hydroxyimidazo[2,1-b][1,3]thiazines with 4-fluoropyridines. The obtained compounds were studied to identify the peculiarities of the physiological development of seedlings of the dicot plant Cucumis sativus. According to the results of the conducted experiment, it was established that the course of physiological processes in the plant organism has a multifaceted nature. The inhibitory effect depends on the structure of the compounds, the concentration of the solutions and the method of their application. It was shown that the synthesized (4-pyridinyloxy)imidazo[2,1-b][1,3]thiazines have a rather strong and stable inhibitory effect in concentrations of 0.1–0.001%. Depending on the intensity and nature of the manifestation of the inhibitory effect, the studied compounds can be placed in a series of increasing inhibitory effect: 3c<3d<3b<3a. Seed soaking in 0.01–0.0001% solutions for all compounds showed the same result with a strong inhibitory effect that caused complete embryonic death of the seeds. The investigated compounds are characterized by a certain period of intense inhibitory effect on the plant organism, therefore they are promising for studying them as components of "pre-emergence" herbicides.

References

Wehtje, G.R. Synergism of Dicamba with Diflufenzopyr with Respect to Turfgrass Weed Control. Weed Technology. 2008. 22(4). 679- 684.

Armbruster, B.L.; Molin, W.T.; Bugg M.W. Effects of the herbicide dithiopyr on cell division in wheat root tips. Pesticide Biochemistry and Physiology. 1991. 39(2). 110-120.

Wang, Q. M.; Sun, H. K.; Cao, H. Y.; Cheng, M. R.; Huang, R. Q. Synthesis and herbicidal activity of 2-cyano-3-substitutedpyridinemethylamino-acrylates. J. Agric. Food Chem. 2003. 51. 5030-5035.

Obojska, A.; Berlicki, L.; Kafarski, P.; Lejczak, B.; Chicca, M. and Forlani, G. Herbicidal Pyridyl Derivatives of Aminomethylene-bisphosphonic Acid Inhibit Plant Glutamine Synthetase. J. Agric. Food Chem. 2004. 52. 3337−3344.

Nan, J.-X.; Yang, J.-F.; Lin, H.-Y.; Yan, Y.-C.; Zhou, S-M.; Wei, X.-F. Chen, Q.; Yang, W.-C.; Qu, R.-Y. and Yang, G.-F. Synthesis and Herbicidal Activity of Triketone-Aminopyridines as Potent p‑Hydroxyphenylpyruvate Dioxygenase Inhibitors. J. Agric. Food Chem. 2021. 69. 5734-5745.

Xie, Y.; Peng, W.; Ding, F.; Liu, S.-J.; Ma, H.-J. and Liu, C.-L. Quantitative structure–activity relationship (QSAR) directed the discovery of 3-(pyridin-2-yl)benzenesulfonamide derivatives as novel herbicidal agents. Pest Manag Sci . 2018. 74(1). 189-199.

Zhao, L.-X.; Hu, J.-j.; Wang, Z.-x. Yin, M.-l.; Zou, Y.-l.; Gao, S.; Fu, Y., Ye, F. Novel phenoxy-(trifluoromethyl) pyridine-2-pyrrolidinone-based inhibitors of protoporphyrinogen oxidase: Design, synthesis, and herbicidal activity. Pesticide Biochemistry and Physiology. 2020. 170. 104684.

Li, G.; Qian, X.; Cui, J.; Huang, Q.; Zhang, R.; Guan, H. Synthesis and Herbicidal Activity of Novel 3-Aminocarbonyl-2-oxazolidinethione Derivatives Containing a Substituted Pyridine Ring. J. Agric. Food Chem. 2006. 54. 125−129.

Slyvka N, Saliyeva L., Holota S., Tkachuk V., Vaskevych A., Vaskevych A., Vovk M. Convenient Synthesis of 4-pyridinyloxy-Modified imidazo[2,1-b][1,3]thiazines as Potential Antiinflammatory Agents. Biointerface Research in Applied Chemistry. 2023, 13, 2, 183.

ДСТУ 4138-2002 Насіння сільськогосподарських культур. Методи визначення якості. Державний стандарт України. Вид. офіц. [чинний від 2004-01-01]. Київ: ДП «УкрНДНЦ», 2003. 173 с. [in Ukrainian].

Published

2023-12-26

How to Cite

СЛИВКА, Н., САЛІЄВА, Л., КАДИКАЛО, Е., БОРТНІК, Т., ТОЛМАЧОВА, В., КОВТУН, О., & ВОВК, М. (2023). EVALUATION OF THE EFFECTIVENESS OF THE USE OF (PYRIDIN-4-YL)OXY SUBSTITUTED IMIDAZO[2,1-b][1,3]THIAZINES AS GROWTH INHIBITORS OF CUCUMIS SATIVUS. Problems of Chemistry and Sustainable Development, (3), 32–40. https://doi.org/10.32782/pcsd-2023-3-5

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