Stereoselective behaviors of the fungicide triadimefon and its metabolite triadimenol during malt storage and beer brewing

The stereoselective behaviors of triadimefon (TF) and its metabolite triadimenol (TN) during barley storage and beer brewing were studied by supercritical fluid chromatography-tandem mass spectrometry to shed light on potential security risks. Matrix-matched calibration curves were constructed for barley and beer, with determination coefficients (r2) ≥ 0.9991. Average recoveries of 77.2–107.5 % and relative standard deviations within 15.0 % were observed. The degradation of the TF enantiomers during storage followed pseudo-first-order kinetics, and S-TF was degraded in preference to R-TF with the half-life ranges 18.5–36.5 d and 20.4–69.3 d, respectively. During beer brewing, the TF enantiomers (enantiomer fraction, 0.44−0.56) were selectively metabolized into TN stereoisomers (diastereomer fraction, 0.43−0.58). The total pesticide content of beer was 93.3 % lower than that of raw grain, whereby the TF content declined by up to 100 % and the TN stereoisomers were reduced by 35.1 %. The processing factors of all the brewing steps were less than one, illustrating that beer consumption is safer after its commercial processing. Furthermore, the TF enantiomers showed different behaviors upon fermentation by two yeast strains. Thus, this work is a useful reference for assessing the food safety risk posed by individual pesticide enantiomers and their contribution to environmental pollution.