title: Single and joint acute toxicity of isocarbophos enantiomers to Daphnia magna.
abstract: Although enantioselectivity in the toxicity of chiral pesticides has received considerable attention over recent years, how coexisting enantiomers interact with each other during their toxic action remains unknown. In this study, we attempted to resolve the enantiomers of a chiral organophosphate insecticide, isocarbophos, and investigated the acute toxicity of individual enantiomers and various enantiomer mixtures. Baseline enantiomeric separation of isocarbophos was achieved on a Chiralcel OD column with the mobile phase of n-hexane/isopropanol (90/10, v/v) at a flow rate of 0.8 mL/min. The resolved enantiomers were differentiated by their responses on a circular dichroism detector. The median lethal concentrations (LC 50) of racemate, (+)-enantiomer, and (-)-enantiomer of isocarbophos toward Daphnia magna were 13.9, 7.08, and 353 microg/L, respectively, after 48 h of static exposure, displaying a 50-fold difference between the enantiomers. Toxic unit (TU) analysis was employed to evaluate the joint toxicity of isocarbophos enantiomer mixtures. The calculated TU mix for the acute toxicity (48 h test) of various binary mixtures ranged from 0.83 to 1.04, suggesting a mode of additive effect. Further evaluation of available literature data for chiral organophosphorus insecticides showed that the joint toxicity of enantiomers may be additive, synergistic, and antagonistic. Therefore, when significant enantioselectivity exists for a chiral pesticide, it is important to also evaluate the interaction of enantiomers in the joint toxicity effect when enantiomers are present in a mixture.
authors.affiliation: Research Center of Green Chirality, Zhejiang University of Technology, Hangzhou, China.
authors.forename: Kunde
authors.initials: K
authors.lastname: Lin
authors.forename: Weiping
authors.initials: W
authors.lastname: Liu
authors.forename: Ling
authors.initials: L
authors.lastname: Li
authors.forename: Jay
authors.initials: J
authors.lastname: Gan
mesh_terms: D000818:Animals; D003621:Daphnia / Q000187:drug effects*; D004347:Drug Interactions; D007306:Insecticides / Q000633:toxicity*; D008294:Malathion / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*; D013237:Stereoisomerism
chemical_list: D007306:Insecticides; D008294:Malathion