4-Nitropyrazolin-5-ones as Readily Available Fungicides of the Novel Structural Type for Crop Protection: Atom-Efficient Scalable Synthesis and Key Structural Features Responsible for Activity

4-Nitropyrazolin-5-ones as Readily Available Fungicides of the Novel Structural Type for Crop Protection: Atom-Efficient Scalable Synthesis and Key Structural Features Responsible for Activity Full article

Journal

Journal of Agricultural and Food Chemistry
ISSN: 1520-5118 , E-ISSN: 0021-8561

Output data

Year: 2022, Volume: 70, Number: 15, Pages: 4572-4581 Pages count : 10 DOI: 10.1021/acs.jafc.1c07413

Authors

Budnikov Alexander S. ^1,2 , Lopat’eva Elena R. ¹ , Krylov Igor B. ^1,2 , Segida Oleg O. ^1,2 , Lastovko Andrey V. ¹ , Ilovaisky Alexey I. ^1,2 , Nikishin Gennady I. ¹ , Glinushkin Alexey P. ² , Terent’ev Alexander O. ^1,2

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky Prosp., 119991 Moscow, Russian Federation
2	All-Russian Research Institute for Phytopathology, B. Vyazyomy, Moscow Region 143050, Russian Federation

The development of new types of fungicides for agriculture and medicine is highly desirable due to the uprising fungal resistance against commonly used compounds. Herein, 4-substituted-4-nitropyrazolin-5-ones (nitropyrazolones) were proposed as highly active fungicides of the novel structural type. The first scalable and practical method for the nitropyrazolone synthesis was proposed, which is atom-efficient, is applicable for the multigram scale synthesis, and allows for production of a wide variety of nitropyrazolones with high yields and purity. The synthesized compounds demonstrated high fungicidal activity against the broad spectrum of phytopathogenic fungi (Venturia inaequalis, Rhizoctonia solani, Fusarium oxysporum, Fusarium moniliforme, Bipolaris sorokiniana, and Sclerotinia sclerotiorum). Their mycelium growth inhibiting activity was comparable or superior to that of kresoxim-methyl. In vitro activity against Staphyloccocus aureus, Candida albicans, and Aspergillus niger revealed that nitropyrazolones are promising candidates against human pathogens. The key factors for the manifestation of high fungicidal activity were established to be an aromatic substituent on the N1 atom and small substituents, such as methyl, at the C3 and C4 positions of the pyrazolone ring.

Budnikov A.S. , Lopat’eva E.R. , Krylov I.B. , Segida O.O. , Lastovko A.V. , Ilovaisky A.I. , Nikishin G.I. , Glinushkin A.P. , Terent’ev A.O.
4-Nitropyrazolin-5-ones as Readily Available Fungicides of the Novel Structural Type for Crop Protection: Atom-Efficient Scalable Synthesis and Key Structural Features Responsible for Activity
Journal of Agricultural and Food Chemistry. 2022. V.70. N15. P.4572-4581. DOI: 10.1021/acs.jafc.1c07413 WOS Scopus OpenAlex

Web of science:	WOS:000794068900007
Scopus:	2-s2.0-85128358517
OpenAlex:	W4223489028

DB	Citing
OpenAlex	8
Scopus	7
Web of science	5