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1,3-Dichlorpropen
D-D · TDD · 1,3-DICHLOROPROPYLENE · 3-Chloropropenyl chloride · 1,3-D · NEMATOX · 1,3-DICHLOROPENE · DICHLOROPROPYLENE
Identifikatoren & physikalische Daten
| CAS No. | 542-75-6 |
|---|---|
| Summenformel | C3H4Cl2 |
| Durchschnittliche Molmasse | 110,97 g/mol |
| Monoisotopische Masse | 109,96900549 g/mol |
| SMILES | ClC=CCCl |
| InChIKey | UOORRWUZONOOLO-UHFFFAOYSA-N |
| PubChem CID | 24883 |
| ChEMBL | CHEMBL155926 |
| EC No. | 208-826-5 |
| DTXSID | DTXSID1022057 |
| Lokaler Name | 1,3-Dichlorpropen |
Chemische & physikalische Eigenschaften
| XLogP | 1,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 31,9 |
| Stoffklassen | Hazardous Air Pollutants (HAPs)Urban Hazardous Air Pollutants (HAPs) - EPA specified greatest potential health threat in urban areasCarcinogensVolatile Organic Compound (VOC) |
| SpringerMaterials Properties | Optical coefficient |
| Pestizide | Pesticide -> EPA IRISAgrochemicals -> Pesticide active substancesActive substance -> EU Pesticides database: Not approvedHerbicides, NematicidesPesticides -> Fumigants |
| LogP (Verteilungskoeffizient) | log Kow = 2.06 (cis-isomer), 2.03 (trans-isomer) at 25 °C1.82 |
| Geruch | Pungent odorSharp, sweet, irritating, chloroform-like odorSweet penetrating odor (technical product, 97-98% pure) |
| Geschmack | Bitter |
| Dichte | 1.2 at 68 °F (USCG, 1999) - Denser than waterwill sink1.220 at 25 °CRelative density (water = 1): 1.221.211.22 @25 °C |
| Color/Form | Colorless to straw-colored liquidAmber liquid |
| Löslichkeit | less than 0.1 mg/mL at 61.7 °F (NTP, 1992)In water, 2 g/L at 20 °CIn water at 25 °C: 2,180 mg/L (cis isomer), 2,320 mg/L (trans isomer)Miscible with hydrocarbons, halogenated solvents, esters, and ketonesSoluble in toluene, acetone, octaneSolubility in water, g/100ml at 20 °C: 0.2soluble in Chloroform, Methanol<0.01 g/100 mL at 16.5 ºC |
| Corrosivity | Corrosive to aluminum, magnesium, and alloys of these metalsIt apparently reacts with certain materials such as rubber, leather, & fur to form a strong odor. |
| Flammpunkt | 95 °F (NTP, 1992)28 °C (82 °F) - closed cup25 °C closed cup35 °C open cup35 °C (open cup)25 °C c.c.78 °F |
| Siedepunkt | 219 °F at 760 mmHg (NTP, 1992)108 °CColorless to straw-colored liquid, pungent, sweet, penetrating odorboiling point 104 °Cspecific gravity 1.211 (25 °C)vapor pressure 28 mm Hg (20 °C) /Technical 1,3-dichloropropene/226 °F108 °C @760 [mm Hg]97-112 °C(lit.) |
| Schmelzpunkt | -60 °C |
| Dampfdruck | E-isomer 3700 Pa, Z-isomer 3500 Pa at 25 °C |
| Brechungsindex | n20/D 1.472(lit.) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | liquid |
| Farbe | Colorless to Light yellow to Light orange |
| Merck | 14,3075 |
| BRN | 1719556 |
| Henry-Konstante | 6.4×10-3 mol/(m3Pa) at 25℃, Wright et al. (1992) |
| Hauptanwendungen | environmental |
| InChI | 1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+ |
| InChIKey | UOORRWUZONOOLO-OWOJBTEDSA-N |
| SMILES | ClC\C=C/Cl |
| LogP (Verteilungskoeffizient) | 2.040 |
| CAS Datenbank | 542-75-6(CAS DataBase Reference) |
| NIST chemische Informationen | 1-Propene, 1,3-dichloro-(542-75-6) |
| EPA chemische Informationen | 1,3-Dichloropropene (542-75-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH226: Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P331, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)H226 (98.4%): Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: 1-Propene, 1,3-dichloro-Hazard Traits - CarcinogenicityDermatotoxicityHepatotoxicity and Digestive System ToxicityOther Toxicological Hazard TraitsRegulation (EC) No 1107/2009 (amended)1-Propene, 1,3-dichloro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1-Propene, 1,3-dichloro- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)2007/619/EC, 2011/36/EU, Reg. (EU) 2022/7402002/2076 |
| Weitere Sicherheitsinformationen | IMAP assessments - CMR chemicals not registered under REACH: Human health tier II assessment |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | FLAMMABLE. POISONOUS GASES ARE PRODUCED IN FIRE. Flashback along vapor trail may occur. Vapor may explode if ignited in an enclosed area. Toxic and irritating gases may be generated. (USCG, 1999)Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 25 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | Flammable liquid.A flammable liquid and dangerous fire hazard when exposed to heat, flame, or oxidizers. |
| Gesundheitsgefahren | VAPOR: Irritating to eyes, nose and throat. LIQUID: Will burn skin and eyes. Harmful if swallowed. (USCG, 1999) |
| Gefahrenübersicht | 1,3-Dichloropropene is used as a component in formulations for soil fumigants. Acute (short-term) inhalation exposure of humans following a spill caused mucous membrane irritation, chest pain, and breathing difficulties. Effects on the lung have been observed in rats acutely exposed to 1,3- dichloropropene by inhalation. Chronic (long-term) dermal exposure may result in skin sensitization in humans. Damage to the nasal mucosa and urinary bladder are the primary health effects of rodents chronically exposed to 1,3-dichloropropene by inhalation. Information on the carcinogenic effects of 1,3- dichloropropene in humans is limitedtwo cases of histiocytic lymphomas and one case of leukemia have been reported in humans accidentally exposed by inhalation to concentrated vapors during cleanup of a tank truck spill. An increased incidence of bronchioalveolar adenomas has been reported in male mice exposed by inhalation but not in rats or female mice. EPA has classified 1,3-dichloropropene as a Group B2, probable human carcinogen.Liquid causes first degree burns on short exposure[CHRIS] Rats exposed to concentrations above 2700 ppm develop severe lung, nasal, liver, and kidney injury. Prolonged exposure at 1000 ppm causes unconsciousness. [ACGIH] Allergic contact dermatitis reported in farmworkers[Kanerva, p. 1780] Can cause lacrimation[HSDB] A potent nephrotoxin in experimental animals[Rosenstock, p. 576] Danger of skin sensitization[MAK] |
| DOT-Nummer und Handbuch | 2047 129 |
| Reaktive Gruppe | Halogenated Organic Compounds |
| EG-Einstufung | Symbol: T, NR: 10-20-24/25-36/37/38-43-65-50/53S: (1/2)-36/37-45-60-61Note: C, D |
| UN-Einstufung | UN Hazard Class: 3UN Pack Group: III |
| Special Reports | USEPA/Office of Prevention, Pesticides and Toxic SubstancesReregistration Eligibility Decision Document - 1,3-Dichloropropene EPA 738-R-98-016 (December 1998). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the USA.[Available from, as of June 23, 2016: http://www.epa.gov/pesticides/reregistration/status.htm]Dangerous Prop Ind Mater Rep 6 (4): 63-70 (1986). Reviews dichloropropene safety, toxicology and health hazards.DHHS/NTPToxicology & Carcinogenesis Studies of Telone II (Technical Grade 1,3-Dichloropropene Containing 1.0% Epichlorohydrin as a Stabilizer) in F344/N Rats and B6C3F1 Mice (Gavage Studies) Technical Report Series No. 269 (1985) NIH Publication No 85-2525[Available from, as of June 10, 2016: http://ntp.niehs.nih.gov/ntp/htdocs/lt_rpts/tr269.pdf]Albrecht WNToxicology and hazard assessment of 1,3-dichloropropene (Telone II). Arch Environ Health 42 (5): P292-6 (1987). Potential adverse health effects from occupational exposure to 1,3-dichloropropene are reviewed and hazards assessed.For more Special Reports (Complete) data for 1,3-DICHLOROPROPENE (9 total), please visit the HSDB record page. |
| Brandbekämpfung | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer for medical attention . |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.(General first aid procedures) |
| Sichere Lagerung | Fireproof. Separated from metals and oxidants. Well closed. Provision to contain effluent from fire extinguishing. Store in an area without drain or sewer access. |
| Firefighting Hazards | Vapors are heavier than air and may travel to a source of ignition and flash back.Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. /Dichloropropenes/ |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.Use water spray to cool unopened containers.To fight fire, use water, foam, /carbon dioxide/, dry chemical.For more Fire Fighting Procedures (Complete) data for 1,3-DICHLOROPROPENE (6 total), please visit the HSDB record page. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature 2 - 8 °C.Store in a flammable liquid storage area or approved cabinet away from ignition sources and corrosive and reactive materials. ... Before entering confined space where this chemical may be present, check to make sure that an explosive concentration does not exist. 1,3-Dichloropropene must be stored to avoid contact with aluminum or magnesium compounds, substances containing fluorine, chlorine, bromine or iodine, and alkaline or corrosive materials, since violent reactions occur. Store in tightly closed containers in a cool, well-ventilated area away from heat. Separate outside storage is preferred. Sources of ignition, such as smoking and open flames are prohibited where 1,3-dichloropropene is handled, used, or stored. Metal containers involving the transfer of 5 gallons or more of 1,3-dichloropropene should be grounded and bonded. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers of 1,3-dichloropropene. A regulated, marked area should be established where this chemical is handled, used, or stored in compliance with OSHA Standard 1910.1045. /Dichloropropenes/Keep container in a well-ventilated place. Keep away from sources of ignition, no smoking. Take precautionary measures against static discharges.PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practicable to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/Outside or detached storage is preferred. Inside storage should be in a standard flammable liquids storage warehouse, room, or cabinet. Separate from oxidizing materials and active metals. |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations.Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Stay upwindkeep out of low areas. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Keep this chemical out of a confined space, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the buildup of explosive concentrations. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. /Dichloropropenes/PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/Eliminate all ignition sources. Approach release from upwind. Stop or control the leak, if this can be done without undue risk. Control runoff and isolate discharged material for proper disposal. |
| Freisetung ohne Brand | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: |
| Entsorgungsverfahren | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U084, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this materialContaminated packaging: Dispose of as unused product.Incineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formulation of phosgene. An acid scrubber is necessary to remove the halo acids produced. In accordance with 40CFR165, follow recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency or by contacting your regional EPA office. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (>/=100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. /Dichloropropenes/For more Disposal Methods (Complete) data for 1,3-DICHLOROPROPENE (11 total), please visit the HSDB record page. |
| Verschüttetes entsorgen | Ventilation. Remove all ignition sources. Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable plastic containers as far as possible. Do NOT let this chemical enter the environment. |
| Preventive Measures | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Wear respiratory protection. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.Appropriate engineering controls: Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling the product.Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.For more Preventive Measures (Complete) data for 1,3-DICHLOROPROPENE (18 total), please visit the HSDB record page. |
| Körperbelastung | Dichloropropene was detected in one of 8 samples of mother's milk from 4 urban areas in the USA but the isomer was not specified(1). /Dichloropropene/ |
| Treatment | Following oral exposure, administer charcoal as a slurry. Monitor liver and kidney functionelevations may not be seen for several days. Following eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Following inhalation, move patient to fresh air, even though initial symptoms and signs are mildkeep the victim quiet, in a semi-reclining position. Minimum physical activity limits the likehood of pulmonary edema. If victim is not breathing, clear the airway of secretions and resuscitate with positive pressure oxygen apparatus. If this is not available, use chest compression to sustain respiration. (T36, A568) |
| Cancer Sites | Hepatic[in animals: cancer of the bladder, liver, lung & forestomach] |
| Wechselwirkungen | ... Treatment /of mouse lung/ with vinyl carbamate (VC) +/- 1,3-D resulted in a 100% gross adenoma incidence. The total number of adenomas was similar between the VC group and those receiving VC and 1,3-D (976 vs. 980 adenomas per 20 mice). ...Treatment with buthionine sulfoximine (0.2 M in 0.58% NaCl, 4 mL/kg body weight (to inhibit glutathione synthesis) 4 hr before dosing with 1,3-dichloropropene or with diethyl maleate (3.1 M in corn oil, 0.4 ml/kg body weight) (to deplete glutathione) or corn oil itself 1 hour before dosing with 1,3-dichloropropene at 50 and 75 mg/kg body weight, resulted in elevations of N-acetylglucosaminidase excretion. In contrast, treatment with aminooxyacetic acid (0.125 M in 0.85 % NaCl, 4 mL/kg body weight) (which inhibits beta lyase activity) 1 hour before 1,3-dichloropropene injection prevented the 1,3-dichloropropene induced release of N-acetylglucosaminidase from the renal tubule. These results suggest that the nephrotoxic effects of 1,3-dichloropropene may be mediated through the mercapturic acid metabolites in the kidney, rather than glutathione depletion. |
| Zielorgane | GastrointestinalEyes, skin, respiratory system, central nervous system, liver, kidneys |
| Gesundheitliche Auswirkungen | Ingestion of cis-1,3-D can lead to developed gastrointestinal distress, adult respiratory distress syndrome, hematological and hepatorenal functional impairment, acute gastrointestinal distress with pulmonary congestion and edema, central nervous depression, perhaps even in the absence of impaired oxygen uptake. Moreover, this can lead to death. Coma may occur rapidly after inhalation. Inhalation of cis-1,3-D at low concentration can cause central nervous depression and moderate irritation of respiratory systemheadache is frequent. After inhalation exposures, malaise, headache, chest and abdominal discomfort and irritability have been reported to persist for several weeks, and perhaps for several years. Severe skin irritation with marked inflammatory response of epidermis can underlying tissues can follow dermal exposure. By any route, possible late injuries to liver, kidneys and heart (T48).Ingestion of trans-1,3-D can lead to developed gastrointestinal distress, adult respiratory distress syndrome, hematological and hepatorenal functional impairment, acute gastrointestinal distress with pulmonary congestion and edema, central nervous depression, perhaps even in the absence of impaired oxygen uptake. Moreover, this can lead to death. Coma may occur rapidly after inhalation. Inhalation of trans-1,3-D at low concentration can cause central nervous depression and moderate irritation of respiratory system |
| Ökotoxizitätswerte | LC50Species: Daphnia magna (Water flea) 1st instarConditions: static bioassay without aeration, 21 °C, pH 7.2-7.5, water hardness 40-50 mg/L CaCO3, alkalinity 30-35 mg/LConcentration: 90 ug/L for 48 hr (95% confidence limit: 63-129 ug/L) /Technical material, 100%/Species: Pimephales promelas (Fathead minnow) weight 0.9 gConditions: static bioassay without aeration, 18 °C, pH 7.2-7.5, water hardness 40-50 mg/L CaCO3, alkalinity 30-35 mg/LConcentration: 4100 ug/L for 96 hr (95% confidence limit: 3390-4970 ug/L) /Technical material, 100%/Species: Micropterus salmoides (Largemouth bass) weight 1.0 gConditions: static bioassay, without aeration, 18 °C, pH 7.2-7.5, water hardness 272 ppm CaCO3, alkalinity 30-35 mg/LConcentration: 3650 ug/L for 96 hr (95% confidence limit: 3520-3780 ug/L) /Technical material, 100%/Species: Stizostedion vitreum (Walleye) weight 1.3 gConcentration: 1080 ug/L for 96 hr (95% confidence limit: 990-1180 ug/L) /Technical material, 100%/.For more Ecotoxicity Values (Complete) data for 1,3-DICHLOROPROPENE (14 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc values of 20-42(2), indicate that 1,3-dichloropropene is expected to have very high mobility in soil(SRC). 1,3-Dichloropropene can adsorb more strongly to soil when it is in the vapor phase than when it is dissolved in water(3). At low temperatures (2 °C), vapor-phase Koc values ranging from 450 to 750 have been measured(3) which suggest moderate to low mobility in soil. Volatilization of 1,3-dichloropropene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 3.55X10-3 atm-cu m/mole(4). 1,3-Dichloropropene is expected to volatilize from dry soil surfaces(SRC) based upon vapor pressures of 34.3 and 23.0 mm Hg for the cis- and trans-isomers of 1,3-dichloropropene(2). Field and laboratory studies have demonstrated that volatilization is an important fate process in soil(3,5). 1,3-Dichloropropene can degrade in soil through abiotic hydrolysis and biodegradation(2,3,5). A 3% of theoretical BOD using activated sludge in the Japanese MITI test suggests 1,3-dichloropropene is not readily biodegradable(6). However, 1,3-dichloropropene has been shown to degrade more rapidly in soil that has a history of treatment than in previously untreated soil indicating microbial adaptation(5). The hydrolysis rate is temperature dependent, with half-lives on the order of a few days to two weeks at temperatures of 15 to 29 °C and 90-100 days at 2 °C(2). Soil metabolism half-lives have been reported to vary from 2 to 54 days(2,7).TERRESTRIAL FATE: Although field applications of 1,3-dichloropropene have shown between 15 and 80% decomposition, the large amount that can be adsorbed (80 to 90%) can result in considerable residues existing months after application is completed. ... Fumigant mixtures of ... 1,3-dichloropropene are applied to the soil in liquid form, usually by means of a chisel applicator. Small amounts of these mixtures escape into the atmosphere by natural diffusion up through the soil profile, and some may leak into the atmosphere from the soil surface through inadequately sealed chisel shank holes. An estimate of the total amount of cis-dichloropropene lost to the atmosphere after a typical application of Telone R to a 30.5 cm depth in a warm, moist, sandy loam soil would amount to approximately 5 to 10%(1).FIELD: Eight months after D-D soil fumigant was applied to muck and sandy loam soils in August during field studies, residues of 1.8 and 4.8 ppm of the cis and trans isomers were found in the muck soil and 0.03 and 0.39 ppm were found in the sandy loam(2). Residues persisted >91 days in the sandy soil of a tree nursery and were also found in neighboring irrigation wells. 1,3-Dichloropropene was injected 0.2 m deep into the soil of three flower bulb fields during summer. Based on soil samples collected at depths of 0-0.6 m, half-lives, for the cis- and trans- isomers were determined to be about 4 days(3). Half-lives of both isomers in soil at 20 °C have been estimated to range between 3 and 25 days(1).AQUATIC FATE: Based on a classification scheme(1), Kocs ranging from 20-42(2) indicate that 1,3-dichloropropene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 3.55X10-3 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3.3 hrs and 4.2 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 10(SRC), from its log Kow of 2.04 (average for the cis- and trans-isomers)(6)and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 3% of theoretical BOD using activated sludge in the Japanese MITI test suggests 1,3-dichloropropene is not readily biodegradable(8). However, 1,3-dichloropropene has been shown to degrade more rapidly in media that has previously been exposed indicating microbial adaptation(9). 1,3-Dichloropropene undergoes hydrolysis in aqueous solution producing 3-chloroallyl alcohol(2). 1,3-Dichloropropene hydrolysis half-lives measured in buffered solutions at pH 5, 7, and 9 were 13.5 days at 20 °C(2). Hydrolysis half-lives measured at pH 5.5 and 7.5 were 2 days at 29 °C, 11-13 days at 15 °C, and 90-100 days at 2 °C(2).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-dichloropropene, which has a vapor pressure of 34.3 and 23.0 mm Hg at 25 °C for the cis and trans-isomers respectively(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3-dichloropropene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 1.9 and 1.1 days for the cis and trans-isomers(SRC), calculated from their respective rate constants of 1.43X10-11 and 8.4X10-12 cu cm/molecule-sec at 25 °C(3). 1,3-Dichloropropene is also degraded in the atmosphere by reaction with ozone and nitrate radicals. The half-life for the reaction with ozone is estimated to be 76 and 17 days for the cis- and trans-isomers(SRC), calculated from their respective rate constants of 6.7X10-19 and 1.5X10-19 cu cm/molecule-sec at 22 °C(4). The half-life for the reaction with nitrate radicals is estimated to be 3.4 days for cis-1,3-dichloropropene(SRC), calculated from its rate constant of 9.5X10-15 cu cm/molecule-sec at room temperature(5). The nitrate radical (NO3) is the dominant atmospheric oxidant during the night-time in most atmospheric environments(6)therefore, night-time degradation appears to be an important fate process for 1,3-dichloropropene(SRC). Results of irradiation studies indicate direct photolysis is not an important fate process in comparison to hydroxyl radicals, ozone and nitrate radicals(2). 1,3-Dichloropropene has been detected in rainwater(7) indicating removal from air by wet deposition is possible(SRC). |
| Lebensmitteluntersuchungswerte | A variety of food samples collected from retail stores in the Kanto plain area of Japan in November 1992 did not have any positive detections for 1,3-dichloropropene (specific detection limit not reported)(1). 1,3-Dichloropropene has not been detected in food(2). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Expositionspfade | The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contactInhalation (L893)oral (L893)dermal (L893)eye contact (L893). |
| Milk Concentrations | ENVIRONMENTAL: Dichloropropene was detected in one of 8 samples of mother's milk from 4 urban areas in the USA but the isomer was not specified(1). /Dichloropropene/ |
| RCRA-Anforderungen | U084As stipulated in 40 CFR 261.33, when 1,3-dichloropropene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5). |
| TSCA-Anforderungen | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Propene, 1,3-dichloro- is included on this list. Effective date: 6/1/87Sunset date: 6/1/97. |
| FIFRA-Anforderungen | Tolerances are established for the combined residues of the fungicide cis- and trans-1,3-dichloropropene and its metabolites cis- and trans-3-chloroacrylic acid, and cis- and trans-3-chloroallyl alcohol in or on the following commodity: Grape.Based on the reviews of the generic data for the active ingredient 1,3-D, as well as other data generated for the 1,3-D Special Review, the Agency has sufficient information on the health effects of 1,3-D and on its potential for ground water contamination. The Agency has determined that 1,3-D products, labeled and used as specified in this Reregistration Eligibility Decision document, will not pose unreasonable adverse effects to humans or the environment. Therefore, the Agency concludes that all products containing 1,3-D, when used under the conditions specified in this document, are eligible for reregistration.As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer safety standards, such as those described in the Food Quality Protection Act of 1996. 1,3-Dichloropropene is found on List A, which contains most pesticides that are used on foods and, hence, have a high potential for human exposure. List A consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0328Pesticide type: Fungicide (nematicide)Registration Standard Date: 09/18/86Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.Active ingredient (AI): 1,3-DichloropropeneData Call-in (DCI) Date(s): 09/28/90, 02/26/91, 10/13/95, 06/11/96AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner. |
| Luftstandards | Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 1,3-Dichloropropene is included on this list. |
| CERCLA-Meldepflichtmengen | Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b). |
| Clean Water Act Anforderungen | 1,3-Dichloropropene is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance. |
| State Drinking Water Standards | (CA) CALIFORNIA 0.5 ug/L |
| Landesrichtlinien für Trinkwasser | (FL) FLORIDA 0.4 ug/L(MA) MASSACHUSETTS 0.4 ug/L(ME) MAINE 4 ug/L(MN) MINNESOTA 2 ug/LFor more State Drinking Water Guidelines (Complete) data for 1,3-DICHLOROPROPENE (6 total), please visit the HSDB record page. |
| Berufliche Expositionsstufe (OEB) | B |
| Arbeitsplatzgrenzwert (OEL) | TWA: 1 ppm (5 mg/m3) [skin] |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1992 3/PG 3 |
| Zollcode | 29032990 |
| RTECS-Nr. | UC8310000 |
| R-Sätze (R) | 10-20/21-25-36/37/38-43-50/53-65-24/25-20 |
| Gefahrensymbole | T,N |
| Sicherheitshinweise (S) | 36/37-45-60-61 |
| Gefahrenklasse | 3Acute Tox. 3 DermalAcute Tox. 3 OralAcute Tox. 4 InhalationAquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| Verpackungsgruppe | II |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 542-75-6(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
This nematocide is used as a sol fumigant prior to crop cultivation. Mainly farmers and process operators employed at pesticide plants are exposed.
Verwenden
1,3-Dichloropropene (a technical-grade mixture of the cis-and transisomers) is used as a preplanting fumigant, mainly for the control of nematodes affecting the roots of plants, selected plant diseases, garden centipedes, wireworms, and weeds; as a solvent; and as an intermediate in the manufacture of 3,3-dichloro-1-propene and other pesticides. It is registered for use on all vegetable, fruit, and nut crops, all forage crops, tobacco, all fiber crops, and all nursery crops (EPA 1998). In Hawaii, 1,3-dichloropropene is used to control nematodes on pineapples at planting (Albrecht 1987). In 2009, three products containing 1,3-dichloropropene as an active ingredient were registered for restricted, non-residential use in the United States (EPA 2009). No products containing 1,3-dichloropropene are registered for use by homeowners (EPA 1998).