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