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Isobenzan (ISO)
TELODRIN · 948 · OMTAN · oms206 · sd4402 · R 6700 · WL 1650 · OMS 206
Identifikatoren & physikalische Daten
| CAS No. | 297-78-9 |
|---|---|
| Summenformel | C9H4Cl8O |
| Durchschnittliche Molmasse | 411,7 g/mol |
| Monoisotopische Masse | 407,777036 g/mol |
| SMILES | ClC1=C(Cl)C2(Cl)C3C(Cl)OC(Cl)C3C1(Cl)C2(Cl)Cl |
| InChIKey | LRWHHSXTGZSMSN-UHFFFAOYSA-N |
| PubChem CID | 9271 |
| ChEBI | CHEBI:82099 |
| EC No. | 206-045-4 |
| DTXSID | DTXSID3021306 |
| Lokaler Name | Isobenzan (ISO) |
Chemische & physikalische Eigenschaften
| XLogP | 4,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 9,2 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 425 |
| Pestizide | Pesticides -> Organochlorine Pesticides |
| LogP (Verteilungskoeffizient) | log Kow = 4.51 /Estimated/ |
| Dichte | 1.87 (EPA, 1998) - Denser than waterwill sink1.87 @25 °C1.87 g/cm3 |
| Color/Form | Whitish to light brown powderCrystals from heptane |
| Löslichkeit | Sol in ether, acetone, benzene, xylene, heavy aromatic naphthaGreater than 1% in ethanol & kerosene25 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 Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomposition it emits toxic fumes of /hydrogen chloride/. |
| Schmelzpunkt | 248 to 252 °F (EPA, 1998)120-122 °C121℃ |
| Dampfdruck | 1e-05 mmHg at 77 °F (EPA, 1998)0.00000292 [mmHg]Vapor pressure = 3X10-6 mm Hg at 20 °C2.92X10-6 mm Hg at 20 °C0.00001 [mm Hg] @25 °C |
| Henry-Konstante | Henry's Law constant = 5.9X10-8 atm-cu m/mol at 25 °C /Estimated/1.7×102 mol/(m3Pa) at 25℃, HSDB (2015) |
| Physical Description | 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 Life | Relatively stable to acidsdehydrochlorination may occur under strong akaline conditions. |
| Siedepunkt | 421.5±45.0 °C(Predicted) |
| Flammpunkt | 9℃ |
| Lagerbedingungen | 2-8°C |
| Farbe | Crystals from heptane |
| Merck | 13,5144 |
| EPA chemische Informationen | Isobenzan (297-78-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH300: 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)H300+H310 (100%): Fatal if swallowed or in contact with skin [Danger Acute toxicity, oralacute toxicity, dermal] |
|---|---|
| Regulatorische Informationen | The 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-Kennzeichnung | Poison |
| Brandgefahren | Chlorine is evolved when this material is heated above 410F. Avoid acids, certain metal salts, and catalytically active carriers. (EPA, 1998) |
| Gesundheitsgefahren | 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 slowlyits half-life in human blood is 2.77 years. (EPA, 1998) |
| Gefahrenübersicht | Highly toxic by skin absorption, inhalation, and ingestionVery slowly eliminated by the human body, with a blood half-life of 2.77 yearsMay cause convulsions and seizures[CAMEO] Over stimulates the CNS causing convulsionsSlowly eliminated by the body[INCHEM] May cause irritation[MSDSonline] |
| Reaktive Gruppe | Ethers |
| Special Reports | USEPAChemical Profile: Isobenzan (1985)WHOEnvironmental Health Criteria 129: Isobenzan (1992)Maroni M, Fait AToxicology 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 JrOrganochlorine 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 Profile | Chlorine is evolved when ISOBENZAN is heated above 410F. Avoid acids, certain metal salts, and catalytically active carriers. [EPA, 1998]. |
| DOT Hazard Classification | IsobenzanMarine pollutant |
| Air and Water Reactions | Insoluble in water. |
| CERCLA-Meldepflichtmengen | 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 micronsor is handled in solution or in molten formor 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 | Acute Tox. 1 (100%)Acute toxicity (dermal) - category 1Acute toxicity (Oral) - Category 2 |
| Brandbekämpfung | (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. |
| Erste Hilfe | Caution: Symptoms may be long lasting because isobenzan is eliminated slowly. (Isobenzan has a half-life of |
| Freisetung ohne Brand | (Non-Specific -- Dry Insecticide) Keep upwind. Avoid bodily contact with the material. (Non-Specific -- Insecticide, Dry, n.o.s.) Keep unnecessary people awayisolate hazard area and deny entry. |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Minimum Risk Level | Intermediate Oral: 0.002 mg/kg/day (L134) Chronic Oral: 0.0003 mg/kg/day (L134) |
| Protective Action Criteria (PAC) | 0.091 [mg/m3]1.0 [mg/m3]6.0 [mg/m3] |
| Personal Protective Equipment (PPE) | 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, liquidOrganochlorine pesticide, solid, toxic/ |
| Körperbelastung | ... 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. |
| Treatment | Treatment is symptomatic, aimed at controlling convulsions, coma, and respiratory depression. If ingested, gastric lavage may be performed, followed by administering activated charcoal powder. (L150) |
| Gesundheitliche Auswirkungen | Poisoning 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) |
| Ökotoxizitätswerte | 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. |
| Umweltverhalten | 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 soilno 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 yrFor more Environmental Fate (Complete) data for ISOBENZAN (7 total), please visit the HSDB record page. |
| Lebensmitteluntersuchungswerte | Isobenzan was detected but concns not reported in the FDA program for monitoring pesticide residues in foods during 1978-198249,877 samples of raw agricultural commodities were analyzed(1). Isobenzan was detected, concns not reported, in 3 fruit samples during 1970-1971(2). |
| Unerwünschte Wirkungen | Other Poison - Organochlorine |
| Expositionspfade | Oral (L111) |
| Milk Concentrations | 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. |
| Toxizitätsübersicht | 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) |
| Ökotoxizitätsauszüge | /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 symptomswithin 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 Symptoms | Symptoms that may result from endrin poisoning are headaches, dizziness, nervousness, confusion, nausea, vomiting, and convulsions. (L112) |
| Wassergefährdungsklasse (WGK) | 1 |
| UN-Transportnummer | 2761 |
| Zollcode | 29329990 |
| RTECS-Nr. | PC1225000 |
| R-Sätze (R) | 27/28-50 |
| Toxizität | LD50 i.v. in rats: 1.8 mg/kg (Tauberger) |
| Gefahrensymbole | T+,N |
| Sicherheitshinweise (S) | 28-36/37-45-61 |
| Gefahrenklasse | 6.1(a) |
| Verpackungsgruppe | II |
| Gefahrstoffdaten | 297-78-9(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Isobenzan (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.