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Министерство науки и высшего образования Российской Федерации
Российская Академия Наук

Scientists of the Zelinsky Institute have proposed an electrochemical method for the synthesis of promising fungicides

27 april 2023 г.

Organic thiocyanates are a promising class of compounds for the development of plant protection products based on them. In particular, thiocyanide derivatives of 1,3-dicarbonyl compounds have high fungicidal activity against a wide range of fungal pathogens affecting agricultural crops.

In the Laboratory for the Study of Homolytic Reactions of the Zelinsky Institute has the discovery of the method for thiocyanation of 1,3-dicarbonyl compounds under the action of electric current without the use of stoichiometric amounts of "material" oxidizing agents was made. The reaction takes place in a structurally simple undivided cell at constant current. A wide range of thiocyanates were obtained in 37-82% yields. It was found that the reaction proceeded with high efficiency only in acetic acid. Presumably, thiocyanation of 1,3-dicarbonyl compounds begins with the formation of (SCN)2 from the SCN anion as a result of anodic oxidation; further addition of (SCN)2 to the double bond of the enol form of the 1,3-dicarbonyl compound leads to the target product.
 

Source:

Andrey S. Kirillov, Egor A. Semenov, Oleg V. Bityukov, Maria A. Kuznetsova, Valentina N. Demidova,  Alexander N. Rogozhin, Alexei P. Glinushkin, Vera A. Vil’, Alexander O. Terent’ev An environmentally benign way to synthesize 2-thiocyano-1,3-dicarbonyl compounds with high antifungal activity: a key role of solvent // Org. Biomol. Chem., 2023, accepted manuscript. DOI: 10.1039/d3ob00474k.