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

Ballari, María Sol, Herrera Cano, Natividad, Lopez, Abel Gerardo, Wunderlin, Daniel Alberto, Feresín, Gabriela Egly, Santiago, Ana Noemí
Journal of agricultural and food chemistry 2017 v.65 no.47 pp. 10325-10331
Aspergillus, Botrytis cinerea, Fusarium oxysporum, agrochemicals, antifungal agents, captan, organic halogen compounds, oxazoles, plant pathogenic fungi, potassium hydroxide, thiazoles
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.