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Toxaphene

Toxaphene. Deanna Worden. Properties. No Distinguished Structure # of Cl attachments and locations vary Toxaphene mixtures contain over 200 derivatives. Persistent Insecticide Solubility in water: 550 µg/L. Result of chlorinating Camphene with chlorine gas in the presence of UV radiation

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Toxaphene

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  1. Toxaphene Deanna Worden

  2. Properties • No Distinguished Structure • # of Cl attachments and locations vary • Toxaphene mixtures contain over 200 derivatives. • Persistent Insecticide • Solubility in water: 550 µg/L • Result of chlorinating Camphene with chlorine gas in the presence of UV radiation • Many conformations were made and the exact makeup of any particular toxaphene mixture is not known

  3. History • First produced as Hercules 3965 by Hercules Co. in 1945 • Used as an insecticide in cotton fields and as piscicide in stocked lakes • Most widely used pesticide in 1979 • Banned by EPA in 1982 • Still presumably used in Soviet areas and South America

  4. How did it Get there? • High volatility allows it to travel large distances via air and come to rest • Used as piscicide in lakes, directly placed in water • Run-off from agricultural uses • Crops • Livestock

  5. When is it going away? • Very low water solubility • Attaches to sediments • Physical half life in soil – up to 12 years • Degradation by high temps can result in removal of chlorine groups • High temperatures and UV radiation can cause total degradation to CO2 and HCl

  6. Aquatic Toxicology • Highly toxic to fish, especially saltwater species • LC50 in 96 hr study showed high range of toxic levels for different species • 1.8µg/L - 22µg/L • Has affinity for soil and sediment • Deposit feeders • Lipophilic – bioaccumulates in the fatty tissues of marine mammals

  7. Toxic Effects • Significant Weight Loss, convulsions, vomiting, and eventually death from respiratory failure in exposed animals • Reduced enzyme activity in brain • Increased liver and kidney size • Reproductive effects – reduced egg viability and deformation of embryos • Shown to have possible carcinogenic effects in comparable mammals such as guinea pigs and rats

  8. Modes of Entry • Ingestion • Animal tissues • Sediment • Uptake through gas exchange in gills • Uptake from atmosphere

  9. Toxic Interactions • Competitive inhibition of ATPases and AChE in neurons and kidneys • Induces Cytochrome P450 in liver • Has antiestrogenic effects in birds and reptiles • Mildly mimics estrogen in mammalian models

  10. Metabolism • Cytochrome P450 metabolism is induced by toxaphene in the liver • This leads to increased metabolism of other xenobiotics • Toxaphene can also be metabolized in the kidney through MFO pathways

  11. Defense • Studies have shown lipid deformations in any mammalian and fish species act as an inhibitor to toxaphene accumulation in tissues

  12. Bibliography • Andersen, G., S. Føreid, J.u. Skaare, B.m. Jenssen, C. Lydersen, and K.m. Kovacs. "Levels of Toxaphene Congeners in White Whales (Delphinapterus Leucas) From Svalbard, Norway." Science of the Total Environment 357 (2006): 128-137. • Attard Barbini, D., P. Stefanelli, S. Girolimetti, A. Di Muccio, and R. Dommarco. "Determination of Toxaphene Residues in Fish Foodstuff by GC–MS." Bulletin of Environmental Contamination and Toxicology 79 (2007): 226-230. • Bernardo, F.j., M.a. Fernandez, and M.j. Gonzalez. "Congener Specific Determination of Toxaphene Residues in Fish Liver Oil Using Gas Chromatography Coupled to Ion Trap MS/MS." Chemosphere 61 (2005): 398-404. • Blanar, C.a., M.a. Curtis, and H.m. Chan. "Environmental Dose of Toxaphene Does Not Affect the Growth, Stress Response, and Selected Physiological Parameters in Juvenile Arctic Charr, (Salvelinus alpinus)." Bulletin of Environmental Contamination and Toxicology 75 (2005): 436-442. • Clark, Clayton, Chen Xiaosong, and Seethu Babu. "Degradation of Toxaphene by Zero-Valent Iron and Bimetallic Substrates." Journal of Environmental Engineering 131 (2005): 1733-1739. • De Geus, Henk-Jan, Harry Besselink, Abraham Brouwer, Jarle Klungsøyr, Brendan McHugh, Eugene Nixon, Gerhard Rimkus, Peter Wester, and Jacob De Boer. "Environmental Occurrence, Analysis, and Toxicology of Toxaphene Compounds." Environmental Health Perspectives 107 (1999): 115-144. • Kucklick, John, and Paul Helm. "Advances in the Environmental Analysis of Polychlorinated Naphthalenes and Toxaphene." Analytical and Bioanalytical Chemistry 386 (2006): 819-836. • Lacayo-Romero, Martha, Bert Van Bavel, and Bo Mattiason. "Degradation of Toxaphene in Aged and Freshly Contaminated Soil." Chemosphere 63 (2005): 609-615. • Palecz, Danuta, Robert Komunski, and Teresa Gabryelak. "Na+K+-ATPase Activity as a Biomarker of Toxaphene Toxicity in Unio Tumidus." Toxicology in Vitro 19 (2005): 707-712. • Trukhin, Alexey, Fedor Kruchkov, Lars Hansen, Roland Kallenborn, Anastacia Kiprianova, and Vladimir Nikiforov. "Toxaphene Chemistry: Separation and Characterisation of Selected Enantiomers of the Polychloropinene Mixtures." Chemosphere 67 (2007): 1695-1700.

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