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Perthane

Perthane. Brad Wong 4/22/2008 Aquatic Toxicology Dr. Mason. p,p’-ethyl DDD C 18 H 20 Cl 2 MW=307.3 Dichlorophylethane Structurally similar to DDT and DDD Chrystalline Solid as a pure compound, and wax as a technical product Melting Point: 56˚C Decomposes on distillation.

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Perthane

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  1. Perthane Brad Wong 4/22/2008 Aquatic Toxicology Dr. Mason

  2. p,p’-ethyl DDD C18H20Cl2 MW=307.3 Dichlorophylethane Structurally similar to DDT and DDD Chrystalline Solid as a pure compound, and wax as a technical product Melting Point: 56˚C Decomposes on distillation Highly insoluble in Water <0.1mg/L at 24˚C Log p=6.660 Highly soluble in organic solvents and acetone, kerosene, and diesel fuel No known taste or smell EPA tolerance level for raw agricultural commodities: 15ppm Perthane DDT Chemical and Physical Properties

  3. One of several DDT analogs administered to people for breast and prostatic cancer Causes adrenalcortical suppression Insecticidal control for pears and vegetables Also for moths and carpet beetles Organochlorine insecticide Marketed as Perthane Lower toxicity to insects and mammals than both DDT and DDD First marketed in 1950 by Rohm and Haas Inc. for use against houseflies and moths As an aerosol Discontinued in 1980 History/Uses

  4. Toxicity • LD50 tests • Oral tests • Mice- 6600 mg/kg • Rat- 6600 mg/kg • Bird- 9000mg/kg • Intravenous Tests • Rat- 73 mg/kg • Mouse- 173 mg/kg • Chronic Toxicity results (oral tests) • No effects in male or female rats and in male mice • Female mice showed significant incidences of cancerous tumors in the liver at higher dosage

  5. Toxicity to Aquatic Life • Lipophilic • Becomes associated with sediments • May dissolve with oil at surface • LD50 for fish: 3mg/L • Must be ingested • High potential to bioaccumulate • May be stored in fat cells • Detected infrequently at low levels in New Jersey study (Stackelberg) • Though similar to DDT, it can undergo biodegredation, and photolysis

  6. What it Affects • Lethal mechanism of organochlorine insecticides • Persistent opening of Na+ channels in neurons • Slows nerve repolarization • Also affected are ATPase pumps • Affects on mammary carcinoma (Leone et al. 1958) • Test on female mice • Found to have a strong inhibitory affect on tumor growth • Had a strong influence on endocrine system • Ovaries of female mice shrank • Adrenal Cortex did not respond in the same way-estrogen formation changed

  7. Study of chemical residues in fish • Caught fish, tested to see what chemicals were present in the tissues. • Focused on areas near industrial sites, agriculture, and cities. • Perthane was found over quanitification limit in only one sample, in an area where it was manufactured

  8. Metabolism • Like all lipophilic molecules, goes through 2 steps for metabolism • Phase 1-oxidation, hydrolysis, hydration or reduction • Phase 2- Forms a more H2O soluble compound

  9. Summary • Very similar structure to DDT and DDD • Less toxic • Used as an insecticide on fruit and vegetables • Also as a moth deterrent • Some positive effects of perthane treatments in humans • Affects adrenal cortex • Not very prevalent in marine systems • Biodegredation • photolysis

  10. References • ChemIDPlus Advanced website http://sis.nlm.nih.gov/ • National Toxicology Program http://ntp.niehs.nih.gov/index.cfm?objectid=070525D7-E7B6-254A-42AEE54D3C7607B3 • Center of Environmental Health UCONN http://ceh.uconn.edu/classroom/organochlor.html • Gruhl, J., (1973) Quantification of aquatic environmental impact of electrical power generation. • Leone, L. A., Hahn, H. B., Mellette, S. J., (1958) Studies of the effects of perthane on spontaneous and transplanted mammary carcinoma in the C3H mouse. Division of Cancer studies and the Department of Medicine. • National Study of Chemical Residues in Fish vol. 1 and 2. Diane Publishing 1992. • Reuber, M.D., (1980) Histopathology of carcinomas of the liver in mice fed perthane.Tumori 66(3) p. 277-83. • Sibly, R.M., Peakall, D.B., Principles f Ecotoxicology. CRC Press, 2006, Boca Raton, FL. • Stackelberg, Paul E., Presence and Distribution of Chlorinated Organic Compounds in Streambed Sediments, New Jersey. U.S. Geological Survey, Fact sheet 118-96. http://nj.usgs.gov/nawqa/linj/fs118.96.html#HDR1

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