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Separation and aquatic toxicity of enantiomers of the organophosphorus insecticide trichloronate
Author(s) -
Liu Weiping,
Lin Kunde,
Gan Jianying
Publication year - 2006
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20323
Subject(s) - enantiomer , chemistry , acute toxicity , daphnia magna , ceriodaphnia dubia , chromatography , chirality (physics) , chiral column chromatography , enantioselective synthesis , toxicity , stereospecificity , daphnia , enantiomeric excess , environmental chemistry , organic chemistry , zooplankton , ecology , biology , catalysis , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
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. Chirality, 2006. © 2006 Wiley‐Liss, Inc.