Behavior of a fenhexamid photoproduct during the alcoholic fermentation of Saccharomyces cerevisiae

The fungicide fenhexamid [N-(2,3-dichloro-4-hydroxyphenyl)-1-methylcyclohexanecarboxamide] degraded rapidly by UV or sunlight irradiation, yielding 7-chloro-6-hydroxy-2-(1-methylcyclohexyl)-1,3-benzoxazole (CHB) as a main photoproduct. CHB was isolated, and its effect on alcoholic fermentation of Saccharomyces cerevisiae was studied. The results indicate that the presence of CHB does not affect the extent of alcohol production. After 12 days, the amount of CHB in the fermentation medium decreased by ca. 65%. Only 25% of the missing CHB was recovered unchanged from yeasts, most likely because it was adsorbed on the yeast wall cell. The remaining part degraded during the fermentation process. Glucan and chitin, two potential adsorbents, which constitute yeast cell walls, exhibited affinity for CHB.