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

Author:
Ballari, María Sol, Herrera Cano, Natividad, Lopez, Abel Gerardo, Wunderlin, Daniel Alberto, Feresín, Gabriela Egly, Santiago, Ana Noemí
Source:
Journal of agricultural and food chemistry 2017 v.65 no.47 pp. 10325-10331
ISSN:
1520-5118
Subject:
Aspergillus, Botrytis cinerea, Fusarium oxysporum, agrochemicals, antifungal agents, captan, organic halogen compounds, oxazoles, plant pathogenic fungi, potassium hydroxide, thiazoles
Abstract:
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.
Agid:
5864304