TOXICOLOGICAL PROFILE FOR
ISODRIN
Criteria and Standards Division
Office of Drinking Water
U.S. Environmental Protection Agency
Washington, DC 20460
August 1989
-------
August 1989
TOXICOLOGICAL PROFILE
FOR
ISODRIN
Criteria and Standards Division
Office of Drinking Water
U.S. Environmental Protection Agency
Washington, DC 20460
-------
ISODRIN
A. GENERAL
1. CAS Number: 465-73-6
2. RTECS Number: 101925000
3. General Name/Svnonvms:
l,2,3,4,10,10-Hexachloro-l,4,4a,5,8,8a-
hexahydro-l,4-endo,endo-5,8-
dlmethanonaphthalene
l,8,9,10,ll,ll-Hexachloro-2,l-7,8-endo-
2,3-7,6-endo-tetracyclo[6.2.1.13-8.02>7]
dodeca-4,9-diene
4. Molecular Formula: C12H8CL8
5. Molecular Weight: 364.93
6. Structure:
Cl
B. PHYSICAL AND CHEMICAL PROPERTIES
1. State: Crystals Sax (1975)
2. Vaoor Pressure: No information was found.
3. Melting Point: 241°C
4. Boiling Point: Decomposes above 1008C
Sax (1975)
Sax and Lewis (1987)
-1-
-------
5. Specific Gravity: No information was found.
6. Solubility: No information was found.
7. Log Kow: No information was found.
8. UV Absorption; No information was found.
C. PHYSICAL/CHEMICAL EQUILIBRIUM FACTORS
1. Bioconcentration Factors (BCF): No information was found.
2. Kwa: No information was found.
3. K,,,.: No information was found.
D. ENVIRONMENTAL FATE
1. Photolysis: No information was found.
2. Leaching; When compared with several other chlorinated insecticides,
isodrin was considered very mobile in Congaree sandy loam soil during
a 13-year period (Nash and Wool son, 1968). Core sampling showed that
approximately 15, 25, 27, 22, and 11% of the total isodrin residues
were found at depths of 3.8, 11.5, 19.1, 26.7, and 34.3 cm below the
soil surface, respectively. The authors noted that 16% of the isodrin
in the original foliar application and 22% of isodrin incorporated
into the soil were recovered from the soil after 12 years.
3. Route of Water Contamination; Water and sediment samples collected
from 11 sites along the Mississippi River were contaminated with
isodrin, endrin, and, in one case, endrin ketone, that originated from
-2-
-------
both agricultural and industrial sources (Barthel et al., 1969).
Levels of isodrin near industrial plants were considerably higher (up
to 24,000 ppm) than those obtained at other sites (generally less than
35 ppm). However, chlorinated pesticide levels did not increase
during a 3-year observation period.
4. Hydrolysis: No information was found.
5. Plant Uptake: Very low levels (0.60 ppm or less) of endrin and endrin
ketone, byproducts of environmental degradation of isodrin, were
detected in a variety of standing agricultural crops, including
cotton, soybeans, sorghum and sorghum stalks, corn stalks, and
"pasture." Concentrations of endrin found in cotton stalks were
approximately 6.26 ppm. Samples were collected from 729 sites across
the United States (Carey et al., 1978).
6. Microbial Degradation: No information was found.
7. Persistence in Soil/Water: Nash and Woolson (1967) and Nash et al.
(1973) reported that approximately 15 to 25% of the nominal levels of
25 or 100 ppm isodrin incorporated into Congaree sandy loam soil
remained 14 to 20 years after treatment. Analysis of soil samples
1 year after insecticide application showed isodrin residues of 33.5
and 155 ppm for the low- and high-dose concentrations, respectively.
At 20 years postapplication, the corresponding residue levels
(including endrin and its derivatives) were 6.5 to 7.5 and 30 to 39
ppm. Disappearance of isodrin from the soil occurred in a linear
fashion. The authors stated that under the conditions of the
experiment, leaching, volatilization, mechanical removal, and
biological degradation were kept to a minimum. However, after 14
years, 95% of the soil residues from isodrin were present as endrin
and endrin derivatives.
-3-
-------
Using data from a series of field studies, Adams (1967) estimated that
isodrin has a half-life of 0.5 to 1.0 years when applied to soil. The
author assumed that the disappearance of isodrin followed a
logarithmic pattern and that activities normally associated with
pesticide loss from soil (e.g., volatilization, leaching, sorption,
chemical and microbial degradation, and plant removal) occurred.
Carey et al. (1978) reported that among 1,486 soil and crop samples
from 37 States, only 3 (0.2%) contained isodrin; concentrations ranged
from 0.01 to 0.02 ppm. Endrin was detected in 14 (0.9%) of the
samples at levels of 0.02 to 1.00 ppm.
Concentrations of isodrin in water and sediment collected from 11
sites along the Mississippi River did not appear to increase during a
3-year observation period despite discharges of high levels (up to
24,000 ppm) of the chlorinated pesticide from one manufacturing plant
(Barthel et al., 1969)
8. Byproducts: Essentially all (at least 95%) of the isodrin (nominal
levels of 25 and 100 ppm) applied to Congaree sandy loam soil was
degraded to endrin and endrin conjugates within 14 years (Nash and
Woolson, 1967; Nash et al., 1973). At 20 years postapplication, the
predominant metabolite, endrin ketone, accounted for about 51 and 75%
of the residues from the low- and high-dose treatments, respectively.
Endrin accounted for approximately 15 to 22%. Other compounds
identified in the 20-year-old samples were endrin aldehyde,, endrin
aldehyde,, endrin alcohol, and dieldrin.
9. Vaporization: No information was found.
-4-
-------
E. ACUTE TOXICITY IN MAMMALS
Animal/strain/sex
Rat/Sherman/M
F
Rat/Sherman/M
F
Route
Oral
Oral
Dermal
Dermal
LD50 (mg/kg)
15
7
35
23
Reference
Gaines (1969)
Gaines (1969)
F. SKIN AND EYE IRRITATION AND SENSITIZATION IN MAMMALS
No Information was found.
G. SUBCHRONIC TOXICITY IN MAMMALS
No information was found.
H. REPRODUCTION AND TERATOGENICITY IN MAMMALS
No information was found.
I. MUTAGENICITY/GENOTOXICITY
In a dominant-lethal assay, negative results were obtained in Swiss mice
administered isodrin orally (1.5 mg/kg, five doses) or intraperitoneally (1.3
or 6.4 mg/kg, single dose) (Epstein et al., 1972).
-5-
-------
J. CHRONIC/CARCINOGENICITY STUDIES IN MAMMALS
No Information was found.
K. PHARMACOKINETICS IN MAMMALS
Approximately 12.5% of a single oral dose of [14C]photoisodrin
(5 mCi/mmole), a photo conversion product of isodrin, was absorbed from the
gastrointestinal tract of two male Swiss-Webster mice within 4 days after
administration of the test material (Reddy and Khan, 1977). The 4-day
cumulative levels of radioactivity in urine and feces were 10 and 82% of the
14C administered, respectively. Individual tissue 14C levels, including those
of organs of the digestive system, were very low (i.e., less than 0.7% of the
administered dose/g tissue) at 4 days posttreatment. In the urine and feces,
about 4.6 and 75% of the administered dose, respectively, were organosoluble;
the remaining 14C (5.5 and 6.75%) was water-soluble. Organic extracts of
urine contained unchanged parent compound plus one unidentified metabolite;
fecal extracts contained photoisodrin plus five additional metabolites. The
aqueous extracts of urine and feces contained three and four metabolites,
respectively, but no [14C]photoisodrin. In subsequent in vitro studies,
microsomal fractions from the liver of male mice were incubated with
[14C]photoisodrin (1.70 x 10s dpm/mg) for 2 hours (Reddy and Khan, 1977).
Ether extracts from this experiment contained approximately 33% of the total
radioactivity, which was divided among five metabolites (1.3 to 7.2% each) and
unchanged test material (17.8%). (The authors reported that radioactivity
levels in the aqueous extract were too low for additional analysis.) Thus,
metabolism of photoisodrin appeared to be mediated by hepatic mixed-function
oxidase.
Endrin was the sole product of the in vitro metabolism of 2.5 x 10'5 M
isodrin by albino rat liver microsomes (Nakatsugawa et al., 1965). NADPH was
-6-
-------
required for optimal epoxidation of isodrin; epoxide production also was
observed in the presence of NADH2 but did not occur in the presence of other
(i.e., oxidized) cofactors such as NADP or NAD.
L. HUMAN HEALTH EFFECTS
No information was found.
M. EXISTING STANDARDS/CRITERIA
No information was found.
-7-
-------
N. REFERENCES
Adams RS. 1967. The fate of pesticide residues in soil. J. Minn. Acad. Sci.
34:44-48.
Barthel WF, Hawthorne JC, Ford JH, Bolton GC, McDowell LL, Grissinger EH,
Parsons DA. 1969. Pesticides in water. Pesticide residues in sediments of
the lower Mississippi River and its tributaries. Pestic. Monit. J. 3:8-66.
Carey AE, Gowen JA, Tai H, Mitchell WG, Wiersma GB. 1978. Soils. Pesticide
residue levels in soils and crops, 1971--National Soils Monitoring Program
(III). Pestic. Monit. J. 12:117-136.
Gaines TB. 1969. Acute toxicity of pesticides. Toxicol. Appl. Pharmacol.
14:515-534.
Epstein SS, Arnold E, Andrea J, Bass W, Bishop Y. 1972. Detection of
chemical mutagens by the dominant lethal assay in the mouse. Toxicol. Appl.
Pharmacol. 23:288-325.
Nakatsugawa T, Ishida M, Dahm PA. 1965. Microsomal epoxidation of cyclodiene
insecticides. Biochem. Pharmacol. 14:1853-1865.
Nash RG, Wool son EA. 1967. Persistence of chlorinated hydrocarbon
insecticides in soils. Science 157:924-927.
Nash RG, Woolson EA. 1968. Distribution of chlorinated insecticides in
cultivated soil. Soil Sci. Soc. Am. Proc. 32:525-527.
Nash RG, Harris WG, Ensor PD, Woolson EA. 1973. Comparative extraction of
chlorinated hydrocarbon insecticides from soils 20 years after treatment. J.
Assoc. Off. Anal. Chem. 56:728-732.
Reddy G, Khan MAQ. 1977. Metabolism of [14C]photoisodrin in mice and
houseflies. Gen. Pharmacol. 8:285-289.
Sax NI. 1975. Dangerous properties of industrial materials. 4th Ed. New
York: Van Nostrand Reinhold Co., p. 804.
Sax NI, Lewis RJ. 1987. Hawley's Condensed Chemical Dictionary, llth Ed.
New York: Van Nostrand Reinhold Co., p. 656.
-8-
------- |