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Bioactivity, toxicity and dissipation of hexaconazole enantiomers

Han, Jiajun, Jiang, Jiazhen, Su, Hang, Sun, Mingjing, Wang, Peng, Liu, Donghui, Zhou, Zhiqiang
Chemosphere 2013 v.93 pp. 2523-2527
Alternaria mali, Alternaria solani, Daphnia magna, Glomerella cingulata, Monilinia fructicola, acute toxicity, antifungal properties, enantiomers, fungi, half life, hexaconazole, risk assessment, sweet peppers, tomatoes
In this study, the bioactivity, acute toxicity and dissipation in vegetables of the individual enantiomers of the fungicide hexaconazole had been investigated. The optical pure single enantiomers were prepared and the bioactivity of (+)-, (−)- and rac-hexaconazole was tested using four target fungi including Colletotrichum gloeosporioides Penz, Alternaria solani, Alternaria mali Roberts and Monilinia fructicola. The results showed (−)-hexaconazole was always more active than (+)-hexaconazole with the fungicidal activity 11–13-fold higher to A. solani, A. mali Roberts and Monilinia fructicola, and 1.26-fold higher to C. gloeosporioides Penz. (−)-Hexaconazole also showed 1.3-fold higher acute toxicity to aquatic species Daphnia magna based on the 48h EC50 values. There was obvious enantioselectivity in the dissipation in tomato with (−)-hexaconazole degraded faster resulting an enrichment of (+)-form, and the half-lives of (−)-hexaconazole and (+)-hexaconazole in tomato were 2.96d and 3.38d respectively, while it was not enantioselective in green pepper, in which the both enantiomers had the half-lives about 4.36d. The findings are helpful for better environmental and ecological risk assessment of hexaconazole on an enantiomeric level.