title: Separation and aquatic toxicity of enantiomers of the organophosphorus insecticide trichloronate.
abstract: Many of the organophosphorus pesticides (OPs) currently used are chiral and therefore consist of mixture of enantiomers. Despite the fact that the biological processes of chiral pesticides are enantioselective, the acute aquatic toxicity of chiral OPs with respect to enantioselectivity has so far received limited research. In this study, the enantiomeric separation and acute aquatic toxicity of trichloronate were investigated. Baseline enantioseparation of trichloronate was successfully achieved using high-performance liquid chromatography on a Chiralcel OJ column, with a mobile phase of n-hexane/n-heptane/ethanol (90/5/5, v/v/v) at the flow rate of 1.0 ml min(-1) and room temperature. The resolved enantiomers were characterized for their optical rotation and by gas chromatography coupled with mass spectrometry. Significant differences were found between the enantiomers in acute aquatic toxicity to Ceriodaphnia dubia and Daphnia magna. The (-)-trichloronate was 8-11 times more toxic to the test organisms than its (+)-form, while the racemate showed intermediate toxicity. These results suggest that assessment of the environmental safety of chiral OPs should take stereospecificity into consideration.
authors.affiliation: Research Center of Green Chirality, Zhejiang University of Technology, Hangzhou, People's Republic of China. wliu@zjut.edu.cn
authors.forename: Weiping
authors.initials: W
authors.lastname: Liu
authors.forename: Kunde
authors.initials: K
authors.lastname: Lin
authors.forename: Jianying
authors.initials: J
authors.lastname: Gan
mesh_terms: D000818:Animals; D002482:Cellulose / Q000031:analogs & derivatives / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003621:Daphnia / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*; D009946:Organothiophosphorus Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000633:toxicity*; D013237:Stereoisomerism; D023382:Toxicity Tests, Acute; D014874:Water Pollutants, Chemical / Q000633:toxicity
chemical_list: D007306:Insecticides; D009943:Organophosphorus Compounds; D009946:Organothiophosphorus Compounds; D014874:Water Pollutants, Chemical; C070231:Chiracel OJ; C004372:trichloronate; D002482:Cellulose