Enantioselective effects of the chiral fungicide tetraconazole in wheat: Fungicidal activity and degradation behavior

Tetraconazole, a chiral triazole fungicide, is widely used for the prevention of plant disease in wheat fields. However, the chirality of pesticides like tetraconazole can cause diverse biological responses. Therefore, it is important that research is conducted to investigate the enantioselective effects of chiral enantiomers in this regard. The absolute configurations of two tetraconazole enantiomers were initially confirmed by ECD (Electrostatic circular dichroism). The bioassay test showed that the fungicidal activity of (R)-(+)-tetraconazole against two pathogens (R. cerealis and F. graminearum) was approximately 1.49–1.98 times greater than that for (S)-(−)- tetraconazole. Following recovery experiments, a modified QuEchERS (Quick, easy, cheap, effective, rugged, safe) method was established using UPLC-MS/MS (ultra-performance liquid chromatography tandem mass spectrometry). The mean recoveries from plant and soil sample ranged from 78.9% to 100.5% with intraday relative standard (RSDr) values of 0.8%–6.9% and interday relative standard (RSDR) values of 3.0%–5.2% respectively. The stereoselective degradation of tetraconazole in wheat meant that (S)-(−)-tetraconazole was more rapidly degraded than (R)-(+)-tetraconazole. Conversely, (R)-(+)-tetraconazole was preferentially degraded in wheat soil. These results will provide us with a greater understanding when assessing future environmental risk assessments and strategies that invoke pesticide reduction. [Display omitted] •Absolute configurations of tetraconazole was confirmed.•A UPLC-MS/MS method for tetraconazole enantiomers was established in wheat plant and soil.•Enantioselective degradation behavior of tetraconazole in wheat plant and soil was found.•Enantioselective fungicidal activity of tetraconazole against R.cerealis and F.graminearum was investigated.