title: Enantioselective bioactivity, acute toxicity and dissipation in vegetables of the chiral triazole fungicide flutriafol.
abstract: The enantioselective bioactivity, acute toxicity and stereoselective degradation of the chiral triazole fungicide flutriafol in vegetables were investigated for the first time using the (R)-, (S)- and rac-flutriafol. The order of the bioactivity against five target pathogens (Rhizoctonia solani, Alternaria solani, Pyricularia grisea, Gibberella zeae, Botrytis cinerea) was found to be (R)-flutriafol>rac-flutriafol>(S)-flutriafol. The fungicidal activity of (R)-flutriafol was 1.49-6.23 times higher than that of (S)-flutriafol. The (R)-flutriafol also showed 2.17-3.52 times higher acute toxicity to Eisenia fetida and Scenedesmus obliquus than (S)-flutriafol. The stereoselective degradation of flutriafol in tomato showed that the active (R)-flutriafol degraded faster, resulting in an enrichment of inactive (S)-form, and the half-lives were 9.23 d and 10.18 d, respectively. Inversely, the (S)-flutriafol, with a half-life of 4.76 d, was preferentially degraded in cucumber. In conclusion, the systemic assessments of the triazole fungicide flutriafol stereoisomers on the enantioselective bioactivity, acute toxicity and environmental behavior may have implications for better environmental and ecological risk assessment.
authors.affiliation: Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Key Laboratory of Integrated Management of Crop Diseases and Pests, Ministry of Education, Nanjing 210095, PR China.
authors.forename: Qing
authors.initials: Q
authors.lastname: Zhang
authors.affiliation: Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Key Laboratory of Integrated Management of Crop Diseases and Pests, Ministry of Education, Nanjing 210095, PR China.
authors.forename: Xiu-de
authors.initials: XD
authors.lastname: Hua
authors.affiliation: Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Key Laboratory of Integrated Management of Crop Diseases and Pests, Ministry of Education, Nanjing 210095, PR China.
authors.forename: Hai-yan
authors.initials: HY
authors.lastname: Shi
authors.affiliation: Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Key Laboratory of Integrated Management of Crop Diseases and Pests, Ministry of Education, Nanjing 210095, PR China.
authors.forename: Ji-song
authors.initials: JS
authors.lastname: Liu
authors.affiliation: Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Key Laboratory of Integrated Management of Crop Diseases and Pests, Ministry of Education, Nanjing 210095, PR China.
authors.forename: Ming-ming
authors.initials: MM
authors.lastname: Tian
authors.affiliation: Department of Pesticide Science, College of Plant Protection, Nanjing Agricultural University, State & Local Joint Engineering Research Center of Green Pesticide Invention and Application, Key Laboratory of Integrated Management of Crop Diseases and Pests, Ministry of Education, Nanjing 210095, PR China. Electronic address: wangmha@njau.edu.cn.
authors.forename: Ming-hua
authors.initials: MH
authors.lastname: Wang
mesh_terms: D000528:Alternaria; D000818:Animals; D020171:Botrytis; D002138:Calibration; D002851:Chromatography, High Pressure Liquid; D018553:Cucumis sativus; D004463:Ecology; D005659:Fungicides, Industrial / Q000737:chemistry* / Q000633:toxicity*; D005874:Gibberella; D018551:Solanum lycopersicum; D009835:Oligochaeta; D012232:Rhizoctonia; D018570:Risk Assessment; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry* / Q000633:toxicity; D014675:Vegetables
chemical_list: D005659:Fungicides, Industrial; D014230:Triazoles; C543009:flutriafol
keywords: Acute toxicity; Bioactivity; Enantioselective degradation; Flutriafol enantiomers