perthane brad wong 4/22/2008 aquatic toxicology dr. mason brad wong 4/22/2008 aquatic toxicology dr....
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PerthanePerthane
Brad Wong4/22/2008
Aquatic ToxicologyDr. Mason
Brad Wong4/22/2008
Aquatic ToxicologyDr. Mason
Chemical and Physical Properties
Chemical and Physical Properties
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
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
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
DDTPerthane
History/UsesHistory/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
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
ToxicityToxicity 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
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
Toxicity to Aquatic LifeToxicity 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 AffectsWhat 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
QuickTime™ and a decompressor
are needed to see this picture.
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
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
MetabolismMetabolism
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
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
QuickTime™ and a decompressor
are needed to see this picture.
SummarySummary
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
ReferencesReferences 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
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