Triazole fungicides are widely applied in agriculture and medicine, and have gradually been proven to have potential detrimental impacts on plants, aquatic ecosystems, and human health. It is worth noting that a large portion of triazoles are chiral, which means they may exert different effects or toxicity to certain targets. To investigate the enantioselective effects of triazoles, our team has done a series of studies, and in this paper we summarized the results so far. Firstly, we have successfully realized the enantiomer separation of nine triazole fungicides with high-performance liquid chromatography. Based on this practical method, we studied the differences of paclobutrazol and uniconazole enantiomers in their growth-retardant activity in rice seedlings, where special enantiomeric selectivity was found. The results showed that (2S,3S)-(-)-paclobutrazol was more active than the (2R,3R)-(+)-paclobutrazol towards shoot growth, and S-(+)-uniconazole was more effective in retarding rice seedling growth than R-(-)-uniconazole. We have also probed the molecular interaction of several triazoles with human serum albumin (HSA) by multispectroscopic techniques and molecular modeling. Hydrophobic, electrostatic interactions, and hydrogen bonding with arginine (218/222) contributed to the binding process, and the complexation induced some conformational and microenvironmental changes of HSA. It is anticipated that these data can provide some information for possible toxicity risk of triazole fungicides to human health, especially in the enantiomer level, and more efforts should be taken in further studies.

Enantioselective separation and plant growth of triazole

248th National Meeting (2014)

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