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

Chemical and Physical Properties  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  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  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 DDT Perthane

History/Uses  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  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

Toxicity  LD50 tests  Oral tests  Mice mg/kg  Rat 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  LD50 tests  Oral tests  Mice mg/kg  Rat 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

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  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

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  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

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

Metabolism  Like all lipophilic molecules, goes through 2 steps for metabolism  Phase 1-oxidation, hydrolysis, hydration or reduction  Phase 2- Forms a more H 2 O soluble compound  Like all lipophilic molecules, goes through 2 steps for metabolism  Phase 1-oxidation, hydrolysis, hydration or reduction  Phase 2- Forms a more H 2 O soluble compound

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  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

References  ChemIDPlus Advanced website  National Toxicology Program 254A-42AEE54D3C7607B3http://ntp.niehs.nih.gov/index.cfm?objectid=070525D7-E7B6- 254A-42AEE54D3C7607B3  Center of Environmental Health UCONN  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  Reuber, M.D., (1980) Histopathology of carcinomas of the liver in mice fed perthane.Tumori 66(3) p  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  ChemIDPlus Advanced website  National Toxicology Program 254A-42AEE54D3C7607B3http://ntp.niehs.nih.gov/index.cfm?objectid=070525D7-E7B6- 254A-42AEE54D3C7607B3  Center of Environmental Health UCONN  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  Reuber, M.D., (1980) Histopathology of carcinomas of the liver in mice fed perthane.Tumori 66(3) p  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