Green Synthesis of Potential Antifungal Agents: 2-Benzyl Substituted Thiobenzoazoles.

Autor: Ballari MS; INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, CONICET, Universidad Nacional de Córdoba, Ciudad Universitaria , 5000 Córdoba, Argentina., Herrera Cano N; Instituto de Biotecnología, Facultad de Ingeniería, Universidad Nacional de San Juan, CONICET , Av. Libertador General San Martín 1109 (O), 5400 San Juan, Argentina., Lopez AG; ICTA, Facultad de Ciencias Exactas, Físicas y Naturales, Universidad Nacional de Córdoba, Ciudad Universitaria , 5000 Córdoba, Argentina., Wunderlin DA; ICYTAC, CONICET and Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria , 5000 Córdoba, Argentina., Feresín GE; Instituto de Biotecnología, Facultad de Ingeniería, Universidad Nacional de San Juan, CONICET , Av. Libertador General San Martín 1109 (O), 5400 San Juan, Argentina., Santiago AN; INFIQC, Departamento de Química Orgánica, Facultad de Ciencias Químicas, CONICET, Universidad Nacional de Córdoba, Ciudad Universitaria , 5000 Córdoba, Argentina.
Jazyk: angličtina
Zdroj: Journal of agricultural and food chemistry [J Agric Food Chem] 2017 Nov 29; Vol. 65 (47), pp. 10325-10331. Date of Electronic Publication: 2017 Nov 09.
DOI: 10.1021/acs.jafc.7b04130
Abstrakt: A series of benzyl-substituted thiobenzoazoles were synthesized by an environmentally friendly approach, to search for new antifungal agrochemicals. Compounds were prepared starting from 2-mercaptobenzoazoles, using KOH, benzyl halides, and water, resulting in a simple and ecological method. New antifungals were tested against a group of phytopathogenic fungi. Two compounds showed an interesting activity against Botrytis cinerea, Fusarium oxysporum, and Aspergillus spp.: 2-((4-(trifluoromethyl)benzyl)thio)benzo[d]thiazole, 3ac, and 2-((4-methylbenzyl)thio)benzo[d]thiazole, 3al. Thus, 3ac and 3al can be considered as broad spectrum antifungal agents. Furthermore, two new compounds, 2-((4-iodobenzyl)thio)benzo[d]thiazole, 3aj, and 2-(benzylthio)benzo[d]oxazole, 3ba, showed better inhibitory effect against Botrytis cinerea and Fusarium oxysporum when compared to the commercial fungicide Captan. Thus, 3aj and 3ba can be considered reduced-spectrum antifungals.
Databáze: MEDLINE