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Isobenzan

HCID 9271
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
297-78-9
Standard SMILES
ClC1=C(Cl)C2(Cl)C3C(Cl)OC(Cl)C3C1(Cl)C2(Cl)Cl
InChIKey
LRWHHSXTGZSMSN-UHFFFAOYSA-N
Molecular formula
C9H4Cl8O
Average molar mass
411.7 g/mol
Monoisotopic mass
407.777036

Overview

Crystals. The technical product is a whitish to light-brown crystalline powder with a mild chemical odor. Used as an insecticide. Not registered as a pesticide in the U.S. (EPA, 1998)

Names & identifiers

Preferred name
Isobenzan
IUPAC
1,3,5,7,8,9,10,10-octachloro-4-oxatricyclo[5.2.1.02,6]dec-8-ene
English name
Isobenzan
Molecular formula
C9H4Cl8O
Molecular weight
411.75

Names & synonyms

ISOBENZANTelodrin297-78-9Shell 4402Isobenzan [ISO:BSI]ENT 25,545-XOMS 206Bas-4402CP 14,957ENT 25,545SD 4402WL 1650
Show more names
948OMTANoms206sd4402oms-206
HSDB 6388EINECS 206-045-4R 6700EPA Pesticide Chemical Code 0585011,3,4,5,6,7,8,8-Octachloro-1,3,3a,4,7,7a-hexahydro-4,7-methanoisobenzofuranBRN 1292346UNII-8IAN133486AI3-24880

Database identifiers

CAS
297-78-9
PubChem CID
9271
DTXSID
DTXSID3021306
ChEBI
CHEBI:82099
UNII
8IAN133486
EC Number
206-045-4
Nikkaji
J2.571B

Properties

Computed structural properties

XLogP
4.6
Topological polar surface area
9.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
18
Formal charge
0
Complexity
425

Experimental & physicochemical properties

PesticidesPesticides -> Organochlorine Pesticides
LogPlog Kow = 4.51 /Estimated/
Density · 3 items

1.87 (EPA, 1998) - Denser than water; will sink

1.87

1.87 @25 °C

Color/Form · 2 items

Whitish to light brown powder

Crystals from heptane

Solubility · 4 items

Sol in ether, acetone, benzene, xylene, heavy aromatic naphtha

Greater than 1% in ethanol & kerosene

25 g/100 ml acetone at 25 °C, 38 g/100 ml benzene at 25 °C, 34 g/100 ml carbon tetrachloride at 25 °C, 2 g/100 ml fuel oil at 25 °C, 34 g/100 ml toluene at 25 °C, 29 g/100 ml xylene at 25 °C.

It is soluble in water to about 0.1 mg/L at 20 °C.

Endocrine DisruptorsPotential endocrine disrupting compound
DecompositionWhen heated to decomposition it emits toxic fumes of /hydrogen chloride/.
Melting Point · 2 items

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Danger

H300+H310 (100%): Fatal if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]

P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory InformationThe New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
DOT LabelPoison
Fire HazardsChlorine is evolved when this material is heated above 410F. Avoid acids, certain metal salts, and catalytically active carriers. (EPA, 1998)
Health Hazards · 1 item

This material is highly toxic. It is absorbed by the skin as well as by the respiratory and gastrointestinal tract. Symptoms may last for a long time because the material is eliminated slowly; its half-life in human blood is 2.77 years. (EPA, 1998)

Hazards Summary · 1 item

Highly toxic by skin absorption, inhalation, and ingestion; Very slowly eliminated by the human body, with a blood half-life of 2.77 years; May cause convulsions and seizures; [CAMEO] Over stimulates the CNS causing convulsions; Slowly eliminated by the body; [INCHEM] May cause irritation; [MSDSonline]

Reactive GroupEthers

Chemistry & industry

Pharmacology

Mechanism of Action · 2 items

The symptoms of poisoning by ... cyclodiene insecticides are characterized by hyperexcitation and convulsions followed by paralysis. ... The cyclodienes endrin, isobenzan, dieldrin and heptachlor expoxide; supressed the GABA induced chloride content /in the chloride channels of dorsal root ganglion neurons of the rat/. The initial transient component of the chloride current was blocked more than the late sustained component. The supression of the GABA mediated synaptic inhibition would cause hyperexcitation of the nervous system. The results are compatible with the convulsant action of these insecticides.

Inhibition potency of polychlorocycloalkanes ... for gamma-aminobutyric acid (GABA) dependent chlorine uptake in mouse brains was studied. Brains of male ICR mice were incubated with insecticides and initiated for assay by addition of radioactive chlorine (Cl), sodium chloride, hydrochloric acid, GABA and glucose. Potencies were estimated by determining inhibition of radioactive sulfur tagged t-butyl-bicyclophosphorothionate binding, GABA dependent Cl uptake, and testing mammalian toxicity. Potencies were expressed as concentrations producing 50% inhibition. The most potent inhibitor was 12-ketoendrin, followed by isobenzan, endrin, dieldrin, heptachlor epoxide, aldrin, heptachlor and lindane. ...

Biological Half-LifeThe biological half-life in body fat was found to be 10.9 days in male rats and 16.6 days in female rats.
Metabolism/Metabolites · 4 items

At low concn of isobenzan in medium containing the microorganism conversion to a polar metabolite A (presumably a conjugate) occurred up to 99%. A, upon hydrolysis with hydrochloric acid, gave a less polar product of unknown structure. Mosquito larvae converted isobenzan to three highly polar products. Hydrolysis of two of these with hydrochloric acid did not change their chromatographic behavior; the third, however, gave a product that in all respects was identical to the lactone ... .

Following iv injection, 13 and 16% of radioactive isobenzan was excreted /in urine/ in 48 hr by male and female rats, respectively, in the form of a hydrophillic metabolite.

Hydrophilic metabolites are formed, one of which has been identified as isobenzan lactone. ...Mosquito larvae and soil fungi metabolize isobenzan in the same way as vertebrates, yielding isobenzan lactone as a metabolite.

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

248 to 252 °F (EPA, 1998)

120-122 °C

Vapor Pressure · 5 items

1e-05 mmHg at 77 °F (EPA, 1998)

0.00000292 [mmHg]

Vapor pressure = 3X10-6 mm Hg at 20 °C

2.92X10-6 mm Hg at 20 °C

0.00001 [mm Hg] @25 °C

Henry's Law ConstantHenry's Law constant = 5.9X10-8 atm-cu m/mol at 25 °C /Estimated/
Physical Description · 2 items

Crystals. The technical product is a whitish to light-brown crystalline powder with a mild chemical odor. Used as an insecticide. Not registered as a pesticide in the U.S. (EPA, 1998)

White to light brown solid; [HSDB] Colorless crystals; [MSDSonline]

Stability/Shelf LifeRelatively stable to acids; dehydrochlorination may occur under strong akaline conditions.

Physicochemical properties

Melting point
121 ℃ · 121℃
Boiling point
421.5 · 421.5±45.0 °C(Predicted)
Density
1.87 g/cm3 · 1.87 g/cm3
Flash point
9 ℃ · 9℃
storage temp.
2 · 2-8°C
color
Crystals from heptane
Merck
13 · 13,5144
Henry's Law Constant
1.7 · 1.7×102 mol/(m3Pa) at 25℃, HSDB (2015)
EWG's Food Scores
5 · 5
FDA UNII
8 IAN133486 · 8IAN133486
EPA Substance Registry System
Isobenzan (297-78-9)
Symbol(GHS)
2 · GHS02,GHS06,GHS08
Signal word
Danger
Hazard statements
225 · H225-H301+H311+H331-H370-H412
Precautionary statements
210 · P210-P280-P302+P352+P312-P304+P340+P312-P370+P378-P403+P235
Hazard Codes
T+,N
Risk Statements
27 · 27/28-50
Safety Statements
28 · 28-36/37-45-61
RIDADR
2761 · 2761
WGK Germany
1 · 1
RTECS
1225000 · PC1225000
HazardClass
6.1 · 6.1(a)
PackingGroup
II
HS Code
29329990 · 29329990
Hazardous Substances Data
297 · 297-78-9(Hazardous Substances Data)
Toxicity
50 i.v · LD50 i.v. in rats: 1.8 mg/kg (Tauberger)
Special Reports · 5 items

USEPA; Chemical Profile: Isobenzan (1985)

WHO; Environmental Health Criteria 129: Isobenzan (1992)

Maroni M, Fait A; Toxicology 78 (1-3): 1-180 (1993). Health effects in man from long term exposure to pesticides, a review of the 1975-1991 literature.

Van Ert M, Sullivan JB Jr; Organochlorine Pesticides. Hazardous Materials Toxicology, Clinical Principles of Environmental Health. Sullivan JB, Krieger KB (eds.) Williams & Wilkins, 1027-52 (1992). The toxicology and adverse health effects associated with exposure to organochlorine pesticides are discussed. ...

For more Special Reports (Complete) data for ISOBENZAN (6 total), please visit the HSDB record page.

Reactivity ProfileChlorine is evolved when ISOBENZAN is heated above 410F. Avoid acids, certain metal salts, and catalytically active carriers. [EPA, 1998].
DOT Hazard Classification · 2 items

Isobenzan

Marine pollutant

Air and Water ReactionsInsoluble in water.
CERCLA Reportable Quantities · 1 item

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. isobenzan is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 or 1,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

Hazard Classes and Categories · 4 items

Acute Tox. 1 (100%)

Acute toxicity (dermal) - category 1

Acute toxicity (Oral) - Category 2

Acute Tox. 1

Safety & protection

Fire Fighting · 1 item

(Non-Specific -- Dry Insecticide) Avoid breathing dusts and fumes from burning material. Keep upwind. Avoid bodily contact with the material. Wear full protective clothing including boots, protective gloves, goggles, and wear self-contained breathing apparatus.

First AidCaution: Symptoms may be long lasting because isobenzan is eliminated slowly. (Isobenzan has a half-life of
Nonfire Spill Response(Non-Specific -- Dry Insecticide) Keep upwind. Avoid bodily contact with the material. (Non-Specific -- Insecticide, Dry, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry.
Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Isolation and EvacuationExcerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Minimum Risk LevelIntermediate Oral: 0.002 mg/kg/day (L134) Chronic Oral: 0.0003 mg/kg/day (L134)
Protective Action Criteria (PAC) · 3 items

0.091 [mg/m3]

1.0 [mg/m3]

6.0 [mg/m3]

Personal Protective Equipment (PPE) · 2 items

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

Personnel protection: ... Wear appropriate chemical protective gloves, boots and goggles. .... /Organochlorine pesticide, liquid; Organochlorine pesticide, solid, toxic/

Toxicology

Body Burden · 2 items

... Beagles developed convulsions when the concn of isobenzan in their blood ranged from 0.042 to 0.072 ppm.

When male and female rats were given a single iv injection of 14C-isobenzan (15 ug/kg bw), the radioactivity in the blood of males 48 hr later was 0.04% of the applied dose and in females was 0.37%. The radioactivity in the organs and tissues ranged between 0.01 and approximately 1.5% of the applied dose, concentrations being lower in females than in males. In abdominal fat, the concentrations were 19.2% in males and 26.6% in females and, in muscle, 12.3% and 9.3%, respectively.

TreatmentTreatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (L150)
Health EffectsPoisoning affects primarily the nerve system. Exposure causes various harmful effects including hyperexcitability, severe central nervous system damage, and death. It is also believed to cause birth defects. (T10, L112)
Ecotoxicity Values · 5 items

LD50 Mallard female, 5-7 month old, oral 4.15 mg/kg (95% confidence limit 2.47-6.97 mg/kg) /Sample purity 99%/

LD50 Coturnix quail (female) oral 4.2 mg/kg bw /from table/

LD50 Quiscalus quiscula (grackle) oral 1.3 mg/kg bw /from table/

LD50 Columba liva (pigeon) oral 10 mg/kg bw /from table/

For more Ecotoxicity Values (Complete) data for ISOBENZAN (10 total), please visit the HSDB record page.

Environmental Fate · 5 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 4,700(SRC), determined from a structure estimation method(2), indicates that isobenzan is expected to have slight mobility in soil(SRC). Volatilization of isobenzan from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.9X10-8 atm-cu m/mole(3), using a fragment constant estimation method(3). Isobenzan is not expected to volatilize from dry soil surfaces(SRC) based on a vapor pressure of 2.92X10-6 mm Hg(4). Biodegradation in soil is not expected to be an important environmental fate process(SRC). The percentage of isobenzan in soil was shown to decrease with increasing clay content in the soil; no isobenzan was recovered after 4-8 days of exposure at 45 °C. On the other hand, moist soils showed a diminished ability to degrade isobenzan after 4 days at 45 °C with the exception of sandy soils(5). A soil half-life of 20-26 weeks depending on soil content has also been calculated(6).

Terrestrial Fate: The behavior of isobenzan in soil was investigated in laboratory tests. Eight types of soil were used ranging from sand to sandy clay, the percentage of sand varying from 93 to 56% and the percentage of clay from 4 to 35%. Following percolation with hexane, the percentage of isobenzan in the eluate fraction was shown to decrease with increasing content of clay in the soil (starting at about 30% clay). Except in the case of sand with a high organic matter content (6-19%), no isobenzan was recovered from the dry soils after 4-8 days of exposure at 45 °C. When the soils were moistened with water and exposed at 45 °C for 4 days, degradation was markedly diminished, with the exception of sand with high organic matter.

Terrestrial Fate: After isobenzan is applied to the soil, a rapid initial loss occurs, after which the remaining cmpd decays at a much slower rate. It persists in soil from 2-7 yr depending on type of soil.

Terrestrial Fate: 95% /telodrin/ disappearance from soils: 2-4 yr

For more Environmental Fate (Complete) data for ISOBENZAN (7 total), please visit the HSDB record page.

Food Survey Values · 1 item

Isobenzan was detected but concns not reported in the FDA program for monitoring pesticide residues in foods during 1978-1982; 49,877 samples of raw agricultural commodities were analyzed(1). Isobenzan was detected, concns not reported, in 3 fruit samples during 1970-1971(2).

Adverse EffectsOther Poison - Organochlorine
Exposure RoutesOral (L111)
Milk Concentrations · 1 item

Three Jersey cows were fed for 28 days at concentrations of technical isobenzan of 0, 0.005, or 0.02 mg/kg in their daily ration (average ration, 20 kg per cow). Residues found in the milk of the cow fed 0.005 mg/kg increased from 0.4 ug/L to 2 ug/L at the end of the feeding period and decreased rapidly thereafter. Higher residues of up to 7.7 ug/L were present in the milk from the cow fed 0.02 mg/kg, which decreased to 1.5 ug/L whole milk 10 weeks after the last day of dosing.

Toxicity Summary · 1 item

It antagonizes the action of the neurotransmitter gamma-aminobutyric acid (GABA) acting at the GABA-A receptors, effectively blocking the GABA-induced uptake of chloride ions and causing hyperexcitability of the central nervous system. It also inhibits Na+ K+ ATPase and Ca2+ and Mg2+ ATPase which are essential for the transport of calcium across membranes. This results in the accumulation of intracellular free calcium ions, which promotes release of neurotransmitters from storage vesicles, the subsequent depolarization of adjacent neurons, and the propagation of stimuli throughout the central nervous system. It also causes increased lipid peroxidation, decreased membrane fluidity, and DNA damage in hepatocytes, but the exact mechanism is unknown. (T10, L112)

Ecotoxicity Excerpts · 5 items

/FIELD STUDIES/ Five sandy loam plots of pasture in New Zealand were treated with telodrin (15% emulsifiable concentrate) at a rate of 2 kg isobenzan/ha in June 1962. The populations of all recorded groups (grass grub, porina, collembola, diptera, hemiptera, coleoptera, mites, and earthworms), except nematodes, were drastically reduced. There was no recovery in the populations of any of the affected groups during the period of up to October 1965. In silt loam plots treated with isobenzan granules (1 kg/ha) in April 1964, the populations of coleoptera, collembola, diptera, mites, and earthworms were all reduced, but to a lesser extent than in the test using 2 kg/ha. Grass grub and hemiptera were not significantly affected,and nematode numbers were elevated 2 yr after treatment.

/FIELD STUDIES/ When loose sandy soil in New Zealand was treated with 2.25 kg isobenzan/ha as 5% granules, the population reduction, 1-18 wk after treatment, was 90-100% for larval coleoptera and lepidoptera and 75% for diptera and earthworms. The number of surface arthropods, 5-15 days after treatment, was reduced by 45%. Six months after treatment, little effect was found on nematodes (13% reduction), bacteria (18% reduction), and fungi (7% increase).

/AQUATIC SPECIES/ Groups of 5 adult Rasbora heteromorpha (Harlequin fish) were exposed for 2 hr at a temp of 20 °C to water (pH 7.2) containing isobenzan (99%), dissolved in DMSO at a concentration of 0.01, 0.1, or 1 mg/L. The fish were then /placed in/ clean water and observed for an additional 48 hr. The treatment with 1 mg/L caused disorientation and the fish became excited by external stimuli, lost ability to swim, and finally all died within 1 hr. In some cases, they appeared to be convulsive. Isobenzan at 0.1 mg/L caused similar symptoms; within 2 hr of exposure, all five fish died. No fish died at 0.01 mg/L, but slight changes in swimming behavior were observed. When guppies (Poecilia reticulata) were tested in the same way, the symptoms of intoxication and susceptibility were similar to those in Harlequin fish, but the guppies were slower to react.

/BIRDS and MAMMALS/ Sign of intoxication /for female mallard/: Ataxia, fasciculation, tenseness, swimming backwards, tail high and fanned, loss of righting reflex, circling, opisthotonos. Signs appeared as soon as 30 min and mortalities occurred about 2 hr after treatment. Survivors appeared normal by the next day, but lost moderate amount of body wt by the end of the 14-day observation period.

/BIRDS and MAMMALS/ When groups of five male and five female Japanese quail (Coturnix coturnix japonica) were fed diets containing 2 or 10 mg isobenzan/kg, the mean survival time in the high-dose group was 6.9 days (range, 2-20 days). The residues in the liver and brain averaged 3.4 mg/kg and 1.4 mg/kg, respectively. In the low-dose group, the mean survival time was 45.9 days (range, 19-65 days) and the average residues in liver and brain were 6 mg/kg and 1.6 mg/kg, respectively. The concentration of isobenzan in the liver of birds fed 2 mg/kg was significantly higher than that in the high-dose group, but the concentration in the brain showed no difference.

Signs and SymptomsSymptoms that may result from endrin poisoning are headaches, dizziness, nervousness, confusion, nausea, vomiting, and convulsions. (L112)

Regulatory information

CERCLA Reportable Quantities · 1 item

Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. isobenzan is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 or 1,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 microns; or is handled in solution or in molten form; or meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... .

Safety data

wgk
1
rtecs
PC1225000
ridadr
2761
hs_code
29329990
Toxicity
LD50 i.v. in rats: 1.8 mg/kg (Tauberger)
risk_code
27/28-50
Signal word
Danger
Symbol(GHS)
GHS02,GHS06,GHS08
hazard_code
T+,N
safety_code
28-36/37-45-61
hazard_class
6.1(a)
packing_group
II
Hazard statements
H225-H301+H311+H331-H370-H412
Precautionary statements
P210-P280-P302+P352+P312-P304+P340+P312-P370+P378-P403+P235
Hazardous Substances Data
297-78-9(Hazardous Substances Data)

It is absorbed orally and distributed primarily to the fat and skin. The major biotransformation product is anti-l 2-hydroxyendrin and the corresponding sulfate, as well as glucuronide metabolites. Anti- and syn-12-hydroxyendrin and 12-ketoendrin are the main toxic metabolites of endrin. It and its metabolites are excreted in urine and feces. (L112)

Absorption, Distribution and Excretion · 5 items

Isobenzan is absorbed by the skin as well as by the respiratory and GI tracts. ... Following iv injection, 13 and 16% of radioactive isobenzan was excreted in 48 hr by male and female rats, respectively, in the form of a hydrophillic metabolite.

The fate of (14)C-labeled telodrin... was followed in various tissues, blood, urine and feces of both male and female rats and in male rabbits dosed iv with insecticides. In rats telodrin was evaluated 48 hr after dosing... and in rabbits after 144 hr. Rats received telodrin at 15 ug/kg... . Rabbits received... telodrin at 241 ug/kg. Male rats excreted 13% of the telodrin radioactivity and female rats, 16% in 48 hr. Within 96 hr, rabbits excreted 13% of the telodrin radioactivity, chiefly as a hydrophilic metabolite. ...In contrast to other insecticides of this group, female rats stored markedly less telodrin... in most of the tissues analyzed, blood, liver, gonads, kidneys, gut, spleen, stomach, heart, lung, brain, abdominal and subcutaneous fat, muscle and whole body. Correspondingly, female rats excreted more of the compounds than did males in the urine and feces. As in Aedes aegypti larvae, telodrin gave a metabolite which, in hydrolysis, yielded a lactone. ...

Isobenzan is readily absorbed through the gastrointestinal wall and is transported in the blood as the unchanged compound. Hydrophilic metabolites are formed, one of which has been identified as isobenzan lactone. Isobenzan accumulates in the tissues and organs of rats and dogs in the following order: fat >liver =muscle >brain >blood. The tissue concentrations of female rats are generally higher than those of males, especially in body fat. The biological half-life in body fat was found to be 10.9 days in male rats and 16.6 days in female rats.

Isobenzan is approximately 4000 times more soluble in rabbit serum than in water, and it has been shown that, during transport in the blood of rats and rabbits, isobenzan is associated with some serum proteins (albumin and alpha-globulin in the rabbit and albumins in the rat) and with constituents of the red blood cell, mainly hemoglobin. The ratio of the distribution of the insecticide between plasma and cells was shown to be approximately 2:1, this ratio remaining constant at different intervals after administration and at different concentrations. Gas chromatography showed that unchanged isobenzan was transported in the blood.

For more Absorption, Distribution and Excretion (Complete) data for ISOBENZAN (7 total), please visit the HSDB record page.

Uses & manufacturing

Uses · 6 items

Used as insecticide; [Merck Index] Used as a broad spectrum contact and stomach insecticide; [INCHEM]

No longer registered as a pesticide for use in the US; [HSDB] Restricted due to environmental persistence and toxicity; [INCHEM]

Farming (Pesticides) [Category: Industry]

For isobenzan (USEPA/OPP Pesticide Code: 058501) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Insecticide

It is used as a pesticide. (L111)

Methods of ManufacturingIsobenzan ... is produced by photochlorination of the Diels-Alder adduct of hexachlorocyclopentadiene and 2,5-dihydrofuran.
Formulations/Preparations · 2 items

Technical Grade: Not less than 95% (wt/wt)

It was supplied in the form of emulsifiable concentrate, dust, and granules ...

General Manufacturing Information · 5 items

Cyclodiene resistance in the housefly, sheep blowfly, and mosquito is most strongly shown to dieldrin, aldrin, and chlordane and most weakly to isobenzan.

... Chlordane-resistant Blattella are strongly cross-resistant to isobenzan ...

The cross-resistance pattern of cyclodiene-resistant root maggots (Hylemya antiqua, brassicae, and liturata) has been extensively studied by tests on the adult flies. ... The cross-resistance is ... moderate to ... isobenzan ...

Isobenzan was made and sold under the trade name Telodrin. ... Isobenzan was manufactured for Shell in Holland. Production started in 1958 and was discontinued in September 1965.

Isobenzan had uses in Europe similar to heptachlor, but production was discontinued in 1966 because of its very high mammalian toxicity.

Applications · 2 items

UsesIsobenzan (telodrin) is a highly toxic organochloride insecticide. It was produced only in the period from 1958 to 1965 and its use has been since discontinued.[1] It is a persistent organic pollutant that can remain in soil for 2 to 7 years, and the biological half-life of isobenzan in human blood is estimated to be about 2.8 years.

General DescriptionCrystals. The technical product is a whitish to light-brown crystalline powder with a mild chemical odor. Used as an insecticide. Not registered as a pesticide in the U.S.

Additional notes

DefinitionChEBI: Isobenzan is a member of oxolanes.