title: Synthesis of low and high chlorinated toxaphene and comparison of their toxicity by zebrafish (Danio rerio) embryo test.
abstract: Toxaphene, also known as camphechlor, is a persistent organochlorine pesticide of complex composition. It is technically produced by photochlorination of camphene with elemental chlorine gas under ultraviolet irradiation. In the present work, a novel, laboratory-scale synthesis using sulfuryl chloride as a chlorinating reagent is described. This approach allowed the degree of chlorination of the resulting mixtures to be arbitrarily adjusted by varying the reaction conditions. Both the compositions and the chlorine contents of the low- and high-chlorinated mixtures acquired using this method were similar to those of environmentally altered toxaphene and technical toxaphene, respectively. For comparison of these mixtures regarding toxicity, they were subjected to the zebrafish (Danio rerio) embryo test. Median effective concentrations (EC50s) were calculated based on the presence of lethal and nonlethal embryonic malformations. Surprisingly, low-chlorinated toxaphene, comprising compounds that also are present in environmentally transformed toxaphene, exhibited a twofold-higher toxicity (according to the EC50 for nonlethal effects) toward the test organisms compared with high-chlorinated toxaphene, the composition of which resembled that of the technical product. Although the effective concentrations in the embryo test were much higher than those in aquatic ecosystems burdened with toxaphene, the present results lead to the assumption that toxaphene is becoming more toxic during transformation in the environment. A decrease in the total amount of toxaphene during environmental breakdown would then be compensated for, at least in part, by the higher toxicity of weathered toxaphene in sediments, soils, and biota of contaminated ecosystems.
authors.affiliation: University of Hohenheim, Institute of Food Chemistry (170), Garbenstrasse 28, DE-70599 Stuttgart, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Kapp
authors.forename: Ulrike
authors.initials: U
authors.lastname: Kammann
authors.forename: Michael
authors.initials: M
authors.lastname: Vobach
authors.forename: Walter
authors.initials: W
authors.lastname: Vetter
mesh_terms: D000818:Animals; D004625:Embryo, Nonmammalian / Q000187:drug effects; D007306:Insecticides / Q000633:toxicity*; D014112:Toxaphene / Q000031:analogs & derivatives* / Q000633:toxicity*; D014874:Water Pollutants, Chemical / Q000633:toxicity*; D015027:Zebrafish / Q000196:embryology*
chemical_list: D007306:Insecticides; D014874:Water Pollutants, Chemical; D014112:Toxaphene