2‐Aminoselenazoles and 2‐aminothiazoles: One‐pot synthesis and control of the fungus Colletotrichum lindemuthianum in common beans

Autor: Fernanda Ac, Pereira, Vitor Sc, de Andrade, Elaine A, Souza, Marcio Cs, de Mattos, Denilson F, Oliveira
Rok vydání: 2022
Předmět:
Zdroj: Pest Management Science. 78:1665-1676
ISSN: 1526-4998
1526-498X
Popis: Anthracnose, caused by the fungus Colletotrichum lindemuthianum, increases losses in the production of common beans. As 1,3-diazoles can act against fungi by inhibiting the enzyme squalene epoxidase (SE), 2-aminoselenazoles and 2-aminothiazoles were synthesized and subjected to tests with the fungus. In addition, the interactions of the most promising substances with the enzyme SE were investigated in silico.Seventeen compounds (eight new) were prepared by a one-pot methodology. In vitro antifungal activities of these compounds against C. lindemuthianum were determined by the minimum inhibitory concentration (MIC) method. Most treatments differed from the control (water), and six azoles with the lowest MIC values underwent an assay employing common bean plants inoculated with the fungus. Among the best results were those from 2-(3-fluorophenyl)amino-4-phenyl-1,3-thiazole (16; 2857 μg mLThe results suggested that 2-(3-fluorophenyl)amino-4-phenyl-1,3-thiazole (16) could be considered a potential fungicidal lead compound for further structural optimization, which according to the in silico study acts via SE inhibition. © 2022 Society of Chemical Industry.
Databáze: OpenAIRE
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