title: Separation and aquatic toxicity of enantiomers of the pyrethroid insecticide lambda-cyhalothrin.
abstract: Chiral pollutants are receiving growing environmental concern due to differential biological activities of their enantiomers. In the present study, enantiomeric separation of the pyrethroid insecticide lambda-cyhalothrin (LCT) was investigated by high-performance liquid chromatography (HPLC) using the columns of Chiralpak AD (amylase tris[3,5-dimethyl-phenyl carbamate]), Chiralpak AS (amylase tris[(S)-1-phenyl carbamate]), Chiralcel OD (cellulose tris[3,5-dimethylphenyl carbamate]), and Chiralcel OJ (cellulose tris[4-methyl benzoate]) with different chiral stationary phases. The differential toxicities of the enantiomers in aquatic systems were evaluated using the acute zebrafish (Danio rerio) toxicity test and the zebrafish embryo test. The enantiomers of LCT were separated completely on all the columns tested and detected by circular dichroism at 236 nm. Better separations were achieved at lower temperatures (e.g., 20 degrees C) and lower levels of polar modifiers (</=5%) in mobile phase. Ethanol was found to be a good modifier of the mobile phase for all the columns, although isopropanol acted better for the Chiralcel OD column. The (-)-enantiomer was >162 times more toxic than its antipode to zebrafish in the acute test. The embryo test indicated that the exposure to LCT enantioselectively induced crooked body, yolk sac edema, and pericardial edema and that the (-)-enantiomer was 7.2 times stronger than the (+)-enantiomer in 96-h mortality. The malformations were induced by the racemate and its (-)-enantiomer at lower concentrations tested (e.g., 50 microg L(-1)), whereas the (+)-enantiomer induced malformations at relatively higher concentrations (>/=100 microg L(-1)). These results suggest that the toxicological effects of chiral pesticides must be evaluated using their individual enantiomers.
authors: Research Center of Environmental Science, College of Biological and Environmental Engineering, Zheijiang University of Technology, Hangzhou, People's Republic of China.
authors: Chao
authors: C
authors: Xu
authors: Jiajia
authors: J
authors: Wang
authors: Weiping
authors: W
authors: Liu
authors: G
authors: G
authors: Daniel Sheng
authors: Yunjie
authors: Y
authors: Tu
authors: Yun
authors: Y
authors: Ma
mesh_terms: D000818:Animals; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D004625:Embryo, Nonmammalian / Q000187:drug effects; D007306:Insecticides / Q000302:isolation & purification*; D009570:Nitriles / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*; D011722:Pyrethrins / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*; D013237:Stereoisomerism; D018675:Toxicity Tests; D014867:Water; D015027:Zebrafish
chemical_list: D007306:Insecticides; D009570:Nitriles; D011722:Pyrethrins; D014867:Water; C037304:cyhalothrin