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

SANTIAGO, ANA NOEMÍ; LOPEZ, ABEL GERARDO; SANTIAGO, ANA NOEMÍ; LOPEZ, ABEL GERARDO; WUNDERLIN, DANIEL ALBERTO; BALLARI, MARÍA SOL; WUNDERLIN, DANIEL ALBERTO; BALLARI, MARÍA SOL; FERESÍN, GABRIELA EGLY; HERRERA CANO, NATIVIDAD; FERESÍN, GABRIELA EGLY; HERRERA CANO, NATIVIDAD

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 2017 p. 10325 - 10331

0021-8561

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.