{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,19]],"date-time":"2025-12-19T21:34:28Z","timestamp":1766180068588,"version":"3.32.0"},"reference-count":33,"publisher":"Oxford University Press (OUP)","issue":"11","license":[{"start":{"date-parts":[[2006,11,1]],"date-time":"2006-11-01T00:00:00Z","timestamp":1162339200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/pages\/standard-publication-reuse-rights"},{"start":{"date-parts":[[2009,12,9]],"date-time":"2009-12-09T00:00:00Z","timestamp":1260316800000},"content-version":"vor","delay-in-days":1134,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["setac.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":[],"published-print":{"date-parts":[[2006,11,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>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.<\/jats:p>","DOI":"10.1897\/06-093r.1","type":"journal-article","created":{"date-parts":[[2006,10,20]],"date-time":"2006-10-20T22:26:19Z","timestamp":1161383179000},"page":"2884-2889","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Synthesis of low and high chlorinated toxaphene and comparison of their toxicity by zebrafish (<i>Danio rerio<\/i>) embryo test"],"prefix":"10.1093","volume":"25","author":[{"given":"Thomas","family":"Kapp","sequence":"first","affiliation":[{"name":"University of Hohenheim, Institute of Food Chemistry (170), Garbenstra\u00dfe 28, DE-70599 Stuttgart, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ulrike","family":"Kammann","sequence":"additional","affiliation":[{"name":"Federal Research Centre for Fisheries, Institute for Fishery Ecology, Palmaille 9, DE-22767 Hamburg, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael","family":"Vobach","sequence":"additional","affiliation":[{"name":"Federal Research Centre for Fisheries, Institute for Fishery Ecology, Palmaille 9, DE-22767 Hamburg, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Walter","family":"Vetter","sequence":"additional","affiliation":[{"name":"University of Hohenheim, Institute of Food Chemistry (170), Garbenstra\u00dfe 28, DE-70599 Stuttgart, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"286","published-online":{"date-parts":[[2006,11,1]]},"reference":[{"key":"2025010318064807500_bib1","first-page":"1","article-title":"Toxaphene: Chemistry, biochemistry, toxicity, and environmental fate","volume":"118","author":"Saleh","year":"1991","journal-title":"Rev Environ Contam Toxicol"},{"key":"2025010318064807500_bib2","doi-asserted-by":"crossref","first-page":"1583","DOI":"10.1351\/pac197951071583","article-title":"Toxaphene (camphechlor), a special report","volume":"51","author":"Korte","year":"1979","journal-title":"Pure Appl Chem"},{"key":"2025010318064807500_bib3","first-page":"237","volume-title":"The Handbook of Environmental Chemistry, Vol 3, Part K\u2014New Types of Persistent Halogenated Compounds","author":"Vetter","year":"2000"},{"key":"2025010318064807500_bib4","doi-asserted-by":"crossref","first-page":"179","DOI":"10.1016\/S0021-9673(03)00438-2","article-title":"Attempt to unravel the composition of toxaphene by comprehensive two-dimensional gas chromatography with selective detection","volume":"994","author":"Koryt\u00e1r","year":"2003","journal-title":"J Chromatogr A"},{"key":"2025010318064807500_bib5","doi-asserted-by":"crossref","first-page":"3902","DOI":"10.1021\/jo01022a074","article-title":"The chlorination of camphene","volume":"30","author":"Jennings","year":"1965","journal-title":"J Org Chem"},{"key":"2025010318064807500_bib6","doi-asserted-by":"crossref","first-page":"3041","DOI":"10.1021\/es991296f","article-title":"FTIR Spectroscopic characterization of chlorinated camphenes and bornenes in technical toxaphene","volume":"34","author":"Kimmel","year":"2000","journal-title":"Environ Sci Technol"},{"volume-title":"Toxicological Profile for Toxaphene","year":"1996","author":"Roney","key":"2025010318064807500_bib7"},{"key":"2025010318064807500_bib8","doi-asserted-by":"crossref","first-page":"2073","DOI":"10.1016\/0045-6535(93)90402-Q","article-title":"Global usage of toxaphene","volume":"27","author":"Voldner","year":"1993","journal-title":"Chemosphere"},{"key":"2025010318064807500_bib9","doi-asserted-by":"crossref","first-page":"238","DOI":"10.1007\/BF01721745","article-title":"Toxaphene inhibition of ATPase activity in catfish, Ictalurus punctatus, tissues","volume":"13","author":"Desaiah","year":"1975","journal-title":"Bull Environ Contam Toxicol"},{"key":"2025010318064807500_bib10","doi-asserted-by":"crossref","first-page":"349","DOI":"10.1007\/BF01054953","article-title":"Toxicity of chlorinated bornane (toxaphene) residues isolated from Great Lakes lake trout (Salvelinus namaycush)","volume":"16","author":"Gooch","year":"1987","journal-title":"Arch Environ Contam Toxicol"},{"key":"2025010318064807500_bib11","doi-asserted-by":"crossref","first-page":"1907","DOI":"10.1016\/0045-6535(93)90386-J","article-title":"Gamma-aminobutyric acid radio-receptor assay: A confirmatory quantitative assay for toxaphene in environmental and biological samples","volume":"27","author":"Saleh","year":"1993","journal-title":"Chemosphere"},{"key":"2025010318064807500_bib12","doi-asserted-by":"crossref","first-page":"591","DOI":"10.1126\/science.377495","article-title":"Toxaphene, a complex mixture of polychloroterpenes and a major insecticide, is mutagenic","volume":"205","author":"Hooper","year":"1979","journal-title":"Science"},{"key":"2025010318064807500_bib13","doi-asserted-by":"crossref","first-page":"475","DOI":"10.1038\/257475a0","article-title":"Long-range transport of toxaphene insecticide in the atmosphere of the western North Atlantic","volume":"257","author":"Bidleman","year":"1975","journal-title":"Nature"},{"year":"2001","author":"United Nations Environment Programme.","key":"2025010318064807500_bib14"},{"key":"2025010318064807500_bib15","doi-asserted-by":"crossref","first-page":"2198","DOI":"10.1002\/etc.5620190908","article-title":"Prominent chlorobornane residues in estuarine sediments contaminated with toxaphene","volume":"19","author":"Maruya","year":"2000","journal-title":"Environ Toxicol Chem"},{"key":"2025010318064807500_bib16","doi-asserted-by":"crossref","first-page":"153","DOI":"10.1016\/S0300-483X(97)00145-5","article-title":"Toxaphene congeners differ from toxaphene mixtures in their dysmorphogenic effects on cultured rat embryos","volume":"124","author":"Calciu","year":"1997","journal-title":"Toxicology"},{"key":"2025010318064807500_bib17","doi-asserted-by":"crossref","first-page":"355","DOI":"10.1016\/S0269-7491(02)00118-5","article-title":"Sensitivity of the zebrafish (Danio rerio) early life stage test for compounds with different modes of action","volume":"120","author":"Roex","year":"2002","journal-title":"Environ Pollut"},{"key":"2025010318064807500_bib18","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1065\/jss2003.09.085","article-title":"A new sediment contact assay to assess particle-bound pollutants using zebrafish (Danio rerio) embryos","volume":"3","author":"Hollert","year":"2003","journal-title":"Journal of Soils and Sediments"},{"key":"2025010318064807500_bib19","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1016\/j.envpol.2004.04.021","article-title":"Genotoxic and teratogenic potential of marine sediment extracts investigated with comet assay and zebrafish test","volume":"132","author":"Kammann","year":"2004","journal-title":"Environ Pollut"},{"key":"2025010318064807500_bib20","first-page":"38","article-title":"DarT: The embryo test with the zebrafish Danio rerio\u2014A general model in ecotoxicology and toxicology","volume":"19","author":"Nagel","year":"2002","journal-title":"Altern Lab Anim"},{"key":"2025010318064807500_bib21","first-page":"87","article-title":"Towards an alternative for the acute fish LC50 test in chemical assessment: The fish embryo toxicity test goes multispecies\u2014An update","volume":"22","author":"Braunbeck","year":"2005","journal-title":"Altern Lab Anim"},{"key":"2025010318064807500_bib22","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1065\/jss2004.10.124.2","article-title":"Bioassay-directed fractionation of organic extracts of marine surface sediments from the North and Baltic Seas\u2014Part II: Results of the biotest battery and development of a biotest index","volume":"5","author":"Kammann","year":"2005","journal-title":"Journal of Soils and Sediments"},{"key":"2025010318064807500_bib23","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1007\/s00244-005-0152-2","article-title":"Toxic effects of brominated indoles and phenols to zebrafish embryos","volume":"51","author":"Kammann","year":"2006","journal-title":"Arch Environ Contam Toxicol"},{"key":"2025010318064807500_bib24","doi-asserted-by":"crossref","first-page":"3023","DOI":"10.1021\/es970291k","article-title":"Isolation, structure elucidation, and identification of a further major toxaphene compound in environmental samples","volume":"31","author":"Vetter","year":"1997","journal-title":"Environ Sci Technol"},{"key":"2025010318064807500_bib25","doi-asserted-by":"crossref","first-page":"679","DOI":"10.1016\/S0045-6535(99)00433-6","article-title":"Synthesis, isolation, and purification of C10\u2013C13 polychloro-n-alkanes for use as standards in environmental analysis","volume":"40","author":"Tomy","year":"1999","journal-title":"Chemosphere"},{"volume-title":"German standard methods for the examination of water, wastewater, and sludge\u2014Subanimal testing (group T)\u2014Part 6: Determination of the nonacute poisonous effect of wastewater to fish eggs by dilution limits","year":"2001","author":"German Standardization Organization.","key":"2025010318064807500_bib26"},{"volume-title":"Water quality\u2014Determination of the acute lethal toxicity of substances to a freshwater fish [Brachydanio rerio Hamilton-Buchanan (Teleostei, Cyprinidae)]\u2014Part 1: Static method","year":"1998","author":"German Standardization Organization.","key":"2025010318064807500_bib27"},{"key":"2025010318064807500_bib28","doi-asserted-by":"crossref","first-page":"111","DOI":"10.1071\/EN05058","article-title":"Effect of cosolvents on toxaphene aqueous solubility","volume":"3","author":"Paan","year":"2006","journal-title":"Environ Chem"},{"key":"2025010318064807500_bib29","doi-asserted-by":"crossref","first-page":"2775","DOI":"10.1002\/etc.5620181218","article-title":"Enantioselective determination of two persistent chlorobornane congeners in sediment from a toxaphene-treated Yukon lake","volume":"18","author":"Vetter","year":"1999","journal-title":"Environ Toxicol Chem"},{"key":"2025010318064807500_bib30","doi-asserted-by":"crossref","first-page":"337","DOI":"10.1016\/0304-4203(87)90067-3","article-title":"Chlorinated hydrocarbons in the open Mediterranean ecosystem and implications for mass balance calculations","volume":"20","author":"Burns","year":"1987","journal-title":"Mar Chem"},{"key":"2025010318064807500_bib31","doi-asserted-by":"crossref","first-page":"218","DOI":"10.1007\/s002449900370","article-title":"Organochlorine pesticides and enantiomers of chiral pesticides in Arctic Ocean water","volume":"35","author":"Jantunen","year":"1998","journal-title":"Arch Environ Contam Toxicol"},{"key":"2025010318064807500_bib32","doi-asserted-by":"crossref","first-page":"2545","DOI":"10.1016\/S0045-6535(98)00307-5","article-title":"Toxaphene in the Great Lakes","volume":"37","author":"Swackhamer","year":"1998","journal-title":"Chemosphere"},{"key":"2025010318064807500_bib33","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1007\/s00244-005-1007-6","article-title":"Trends of chlorinated organic contaminants in Great Lakes Trout and Walleye from 1970 to 1998","volume":"50","author":"Hickey","year":"2006","journal-title":"Arch Environ Contam Toxicol"}],"container-title":["Environmental Toxicology and Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1897%2F06-093R.1","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/academic.oup.com\/etc\/article-pdf\/25\/11\/2884\/59677091\/5620251111.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/academic.oup.com\/etc\/article-pdf\/25\/11\/2884\/59677091\/5620251111.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,1,11]],"date-time":"2025-01-11T17:01:46Z","timestamp":1736614906000},"score":1,"resource":{"primary":{"URL":"https:\/\/academic.oup.com\/etc\/article\/25\/11\/2884\/7770737"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2006,11,1]]},"references-count":33,"journal-issue":{"issue":"11","published-online":{"date-parts":[[2006,11,1]]},"published-print":{"date-parts":[[2006,11,1]]}},"URL":"https:\/\/doi.org\/10.1897\/06-093r.1","relation":{},"ISSN":["0730-7268","1552-8618"],"issn-type":[{"type":"print","value":"0730-7268"},{"type":"electronic","value":"1552-8618"}],"subject":[],"published-other":{"date-parts":[[2006,11,1]]},"published":{"date-parts":[[2006,11,1]]},"assertion":[{"value":"2006-02-24","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2006-05-26","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2009-12-09","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}