C–O Coupling of Hydrazones with Diacetyliminoxyl Radical Leading to Azo Oxime Ethers—Novel Antifungal Agents

C–O Coupling of Hydrazones with Diacetyliminoxyl Radical Leading to Azo Oxime Ethers—Novel Antifungal Agents Full article

Journal

Molecules
ISSN: 1420-3049

Output data

Year: 2023, Volume: 28, Number: 23, Article number : 7863, Pages count : DOI: 10.3390/molecules28237863

Authors

Budnikov Alexander S. ^1,2 , Krylov Igor B. ^1,3,2 , Shevchenko Mikhail I. ^3,2 , Segida Oleg O. ^1,2 , Lastovko Andrey V. ² , Alekseenko Anna L. ^3,2 , Ilovaisky Alexey I. ^1,2 , Nikishin Gennady I. ² , Terent’ev Alexander O. ^1,3,2

Affiliations

1	All-Russian Research Institute for Phytopathology, B. Vyazyomy, 143050 Moscow, Russia
2	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991 Moscow, Russia
3	Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, 125047 Moscow, Russia

Selective oxidative C–O coupling of hydrazones with diacetyliminoxyl is demonstrated, in which diacetyliminoxyl plays a dual role. It is an oxidant (hydrogen atom acceptor) and an O-partner for the oxidative coupling. The reaction is completed within 15–30 min at room temperature, is compatible with a broad scope of hydrazones, provides high yields in most cases, and requires no additives, which makes it robust and practical. The proposed reaction leads to the novel structural family of azo compounds, azo oxime ethers, which were discovered to be highly potent fungicides against a broad spectrum of phytopathogenic fungi (Venturia inaequalis, Rhizoctonia solani, Fusarium oxysporum, Fusarium moniliforme, Bipolaris sorokiniana, Sclerotinia sclerotiorum).

Budnikov A.S. , Krylov I.B. , Shevchenko M.I. , Segida O.O. , Lastovko A.V. , Alekseenko A.L. , Ilovaisky A.I. , Nikishin G.I. , Terent’ev A.O.
C–O Coupling of Hydrazones with Diacetyliminoxyl Radical Leading to Azo Oxime Ethers—Novel Antifungal Agents
Molecules. 2023. V.28. N23. 7863 . DOI: 10.3390/molecules28237863 WOS Scopus OpenAlex

Web of science:	WOS:001116652700001
Scopus:	2-s2.0-85179324488
OpenAlex:	W4389193206

DB	Citing
OpenAlex	2
Scopus	1
Web of science	2