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(2E,2′E)-2,2′-(1,2,4-Thiadiazole-3,5-diyl)bis[3-arylacrylonitriles]: Synthesis and Antidote Activity Towards 2,4-D Herbicide

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Abstract

Oxidation of (Е)-3-aryl-2-cyanothioacrylamides under the action of the Et2S(O)–HCl system leads to the formation of (2Е,2′E)-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis[3-arylacrylonitriles] in 54–91% yields. Structure of the obtained compounds was confirmed by the two-dimensional NMR spectroscopy data. A plausible reaction mechanism was discussed. Two compounds showed a pronounced antidote effect against 2,4-D herbicide in a laboratory experiment on sunflower seedlings in the absence of growth-stimulating activity.

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ACKNOWLEDGMENTS

The studies were carried out using the equipment of the Scientific and Educational Center “Diagnostics of the Structure and Properties of Nanomaterials” and the Center for Collective Use “Ecological Analytical Center” of the Kuban State University.

Funding

This work was financially supported by the Ministry of Education and Science of the Russian Federation (project no. 0795-2020-0031) and the North Caucasus Federal University (interdisciplinary project “Synthesis and antidote activity against the herbicide 2,4-D heterocyclic derivatives of methylene active nitriles”) within the framework of the Strategic Academic Leadership Program “Priority 2030”.

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Authors and Affiliations

  1. Kuban State University, 350040, Krasnodar, Russia

    P. G. Dakhno, V. V. Dotsenko & V. D. Strelkov

  2. North Caucasus Federal University, 355009, Stavropol, Russia

    V. V. Dotsenko, V. D. Strelkov, N. A. Aksenov & I. V. Aksenova

  3. Kuban State Technological University, 350072, Krasnodar, Russia

    V. K. Vasilin

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  1. P. G. Dakhno
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Correspondence to V. V. Dotsenko.

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Dakhno, P.G., Dotsenko, V.V., Strelkov, V.D. et al. (2E,2′E)-2,2′-(1,2,4-Thiadiazole-3,5-diyl)bis[3-arylacrylonitriles]: Synthesis and Antidote Activity Towards 2,4-D Herbicide. Russ J Gen Chem 92, 2822–2831 (2022). https://doi.org/10.1134/S1070363222120337

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