One-pot sequential synthesis and antifungal activity of 2-(benzylsulfonyl)benzothiazole derivatives

BALLARI, MARÍA SOL; HERRERA CANO, NATIVIDAD*; WUNDERLIN, DANIEL A.; FERESIN, GABRIELA E.; SANTIAGO, ANA N.

RSC Advances

Royal Society of Chemistry

Año: 2019 vol. 9 p. 29405 - 29413

New antifungal agrochemicals, derived from 2-(benzylsulfonyl)benzothiazole were synthesized by anenvironmentally friendly method, using water as reaction medium. These compounds were prepared bya one-pot, two-step synthesis, starting from 2-mercaptobenzothiazole and benzyl halides. The potentialfungicides were tested against a panel of phytopathogenic fungi, with many of them showinga significant improvement compared to the non-oxidized analogues and the commercial antifungalCaptan. The new derivatives 2-((2-chlorobenzyl)sulfonyl)benzo[d]thiazole (4f) and 2-((4-methylbenzyl)sulfonyl)benzo[d]thiazole (4k) presented remarkable properties, being able to inhibit the growth of tworesistant moulds (Aspergillus fumigatus and Aspergillus ustus). Both 4f and 4k could be classified asbroad-spectrum fungicides, emerging as possible candidates for the control of these moulds, whichhave negative impact in food production.