(2E,2′E)-2,2′-(1,2,4-Thiadiazole-3,5-diyl)bis[3-arylacrylonitriles]: Synthesis and Antidote Activity Towards 2,4-D Herbicide
P. G. Dakhnoa (https://orcid.org/0000-0002-5581-0241), V. V. Dotsenkoa, b, * (http://orcid.org/0000-0001-7163-0497), V. D. Strelkova, b (https://orcid.org/0000-0002-0682-4815), V. K. Vasilinc (http://orcid.org/0000-0003-3707-9173), N. A. Aksenovb (http://orcid.org/0000-0002-7125-9066), and I. V. Aksenovab (http://orcid.org/0000-0002-8083-1407)
aKuban State University, Krasnodar, 350040 Russia
bNorth Caucasus Federal University, Stavropol, 355009 Russia
cKuban State Technological University, Krasnodar, 350072 Russia
email: *victor_dotsenko_@mail.ru
Received 26 August, 2022
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.
Keywords:
cyanothioacetamide,
2-cyanothioacrylamides,
diethyl sulfoxide,
oxidative dimerization of thioamides,
1,2,4-thiadiazoles,
herbicide antidotes
DOI: 10.1134/S1070363222120337