1,3-Dichloropropene

Hazardous Air Pollutants (HAPs)

Urban Hazardous Air Pollutants (HAPs) - EPA specified greatest potential health threat in urban areas

Carcinogens

Volatile Organic Compound (VOC)

Pesticide -> EPA IRIS

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Herbicides, Nematicides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Fumigants

log Kow = 2.06 (cis-isomer), 2.03 (trans-isomer) at 25 °C

1.82

Pungent odor

Sharp, sweet, irritating, chloroform-like odor

Sweet penetrating odor (technical product, 97-98% pure)

1.2 at 68 °F (USCG, 1999) - Denser than water; will sink

1.220 at 25 °C

Relative density (water = 1): 1.22

1.21

1.22 @25 °C

1.21

Colorless to straw-colored liquid

Amber liquid

less than 0.1 mg/mL at 61.7 °F (NTP, 1992)

In water, 2 g/L at 20 °C

In water at 25 °C: 2,180 mg/L (cis isomer), 2,320 mg/L (trans isomer)

Miscible with hydrocarbons, halogenated solvents, esters, and ketones

Soluble in toluene, acetone, octane

Solubility in water, g/100ml at 20 °C: 0.2

Corrosive to aluminum, magnesium, and alloys of these metals

It apparently reacts with certain materials such as rubber, leather, & fur to form a strong odor.

95 °F (NTP, 1992)

28 °C (82 °F) - closed cup

25 °C closed cup; 35 °C open cup

35 °C (open cup)

25 °C c.c.

95 °F

219 °F at 760 mmHg (NTP, 1992)

108 °C

Colorless to straw-colored liquid, pungent, sweet, penetrating odor; boiling point 104 °C; specific gravity 1.211 (25 °C); vapor pressure 28 mm Hg (20 °C) /Technical 1,3-dichloropropene/

108 °C

226 °F

108 °C @760 [mm Hg]

Danger

H226: 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)

Danger

H226 (98.4%): 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)

Chemical: 1-Propene, 1,3-dichloro-

Hazard Traits - Carcinogenicity; Dermatotoxicity; Hepatotoxicity and Digestive System Toxicity; Other Toxicological Hazard Traits

Regulation (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) 2022/740

2002/2076

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.

Flammable liquid.

A flammable liquid and dangerous fire hazard when exposed to heat, flame, or oxidizers.

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 limited; two 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]

USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration 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/NTP; Toxicology & 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 WN; Toxicology 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.

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.

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 .

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)

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/

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.

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.

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 upwind; keep 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.

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 material; Contaminated 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.

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.

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.

Following oral exposure, administer charcoal as a slurry. Monitor liver and kidney function; elevations 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 mild; keep 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)

Following oral exposure, administer charcoal as a slurry. Monitor liver and kidney function; elevations 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 mild; keep 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)

Hepatic

[in animals: cancer of the bladder, liver, lung & forestomach]

... 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.

Gastrointestinal

Eyes, skin, respiratory system, central nervous system, liver, kidneys

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 system; headache 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; headache 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).

LC50; Species: Daphnia magna (Water flea) 1st instar; Conditions: static bioassay without aeration, 21 °C, pH 7.2-7.5, water hardness 40-50 mg/L CaCO3, alkalinity 30-35 mg/L; Concentration: 90 ug/L for 48 hr (95% confidence limit: 63-129 ug/L) /Technical material, 100%/

LC50; Species: Pimephales promelas (Fathead minnow) weight 0.9 g; Conditions: static bioassay without aeration, 18 °C, pH 7.2-7.5, water hardness 40-50 mg/L CaCO3, alkalinity 30-35 mg/L; Concentration: 4100 ug/L for 96 hr (95% confidence limit: 3390-4970 ug/L) /Technical material, 100%/

LC50; Species: Micropterus salmoides (Largemouth bass) weight 1.0 g; Conditions: static bioassay, without aeration, 18 °C, pH 7.2-7.5, water hardness 272 ppm CaCO3, alkalinity 30-35 mg/L; Concentration: 3650 ug/L for 96 hr (95% confidence limit: 3520-3780 ug/L) /Technical material, 100%/

LC50; Species: Stizostedion vitreum (Walleye) weight 1.3 g; Conditions: static bioassay without aeration, 18 °C, pH 7.2-7.5, water hardness 40-50 mg/L CaCO3, alkalinity 30-35 mg/L; Concentration: 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.

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).

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).

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 contact

Inhalation (L893) ; oral (L893) ; dermal (L893) ; eye contact (L893).

Inhalation (L893) ; oral (L893) ; dermal (L893) ; eye contact (L893).

U084; As 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).

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: 6/1/87; Sunset date: 6/1/97.

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: 0328; Pesticide type: Fungicide (nematicide); Registration Standard Date: 09/18/86; Case 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-Dichloropropene; Data Call-in (DCI) Date(s): 09/28/90, 02/26/91, 10/13/95, 06/11/96; AI 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.

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.

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).

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.

(FL) FLORIDA 0.4 ug/L

(MA) MASSACHUSETTS 0.4 ug/L

(ME) MAINE 4 ug/L

(MN) MINNESOTA 2 ug/L

For more State Drinking Water Guidelines (Complete) data for 1,3-DICHLOROPROPENE (6 total), please visit the HSDB record page.

1,3-Dichloropropene (1,3-D) is a soil fumigant used primarily for preplanting control of parasitic nematodes. In a previous chronic dietary exposure study, 1,3-D induced an increased incidence of hepatocellular adenomas in male rats at a dose of 25?mg/kg/day. Although the mechanism for tumor induction in the rat liver by 1,3-D has not been specifically elucidated, available data suggested that the observed liver tumorigenesis was through a nongenotoxic mode of action at the tumor promotion stage. Fischer 344 rats containing preneoplastic lesions were treated (via gavage) with 25 mg/kg/day 1,3-D or 80 mg/kg/day phenobarbital (PB) for 30 days and 60 days, or for 30 days followed by a 30-day recovery period (no compound exposure). Following treatment, placental form glutathione S-transferase (GSTP) positive and GSTP-negative liver focal lesions were quantitated as to size and number. 1,3-D treatment had no effect on GSTP-positive foci number or relative size but significantly increased the number, labeling index, and relative size of GSTP-negative focal lesions (identified by H and E staining) after 30 and 60 days of treatment. Following the 30-day recovery period, the number, labeling index, and relative size of the GSTP-negative lesions in 1,3-D-treated animals returned to control levels. As expected, PB treatment produced an increase in number and relative size of the GSTP-positive lesions. The results of this study are consistent with 1,3-D inducing liver carcinogenesis through a nongenotoxic mode of action by functioning as a tumor promoter specifically through induction of a non-GSTP staining focal hepatocyte population.

... An increase in concentration of rat-liver homogenate fraction (S9) in the metabolizing system (S9 mix) enhances mutagenicity for 1,3-dichloropropene and 2,3-dichloro-1-propene. According to the effects of the enzyme inhibitors SKF525, 1,1,1-trichloropropene-2,3-oxide and cyanamide, the allylic chloropropenes fall into 3 groups distinguished by their mode of metabolic activation by S9 mix. 1,3-Dichloropropene is hydrolyzed to the corresponding allylic alcohol which can be oxidized to the respective acroleins (hydrolytic oxidative pathway). Structural parameters like chloro substitution of the central C atom of the substituted induced polarization of the C as cis/trans isomerism might be responsible for different substrate properties for the enzymes involved in allylic chloropropene metabolism, thus determining different degrees of activation by either one or both pathways.

Computed molecular properties were compared with experimental mutagenic potentials of some allylic compounds. The computational results suggest that the primary mechanism of action involves the SN1 formation of allylic cations which then react with nucleophilic centers of nucleic acid bases. The usefulness of computed properties in estimating the degree of alkylating activity and mutagenicity was evaluated. In general, stability of the allylic carbocation intermediate and the degree of charge delocalization in the allyl system correlate well with observed mutagenic potentials.

To investigate the mechanism of 1,3-dichloropropene induced hepatotoxicity, we studied effects of modulation in concn or activities of glutathione, glutathione S-transferase, cytotchrome p-450 on 1,3-dichloropropene toxicity in mice. Piperonyl butoxide was used to inhibit cytochrome p-450 and buthionine sulfoximine to inhibit glutathione synthesis. 1,3-dichloropropene (300 mg/kg) administered with a stomach tube significantly increased plasma glutamate oxaloacetate transaminase and glutamate pyruvate transaminase activities as well as hepatic centrilobular swelling 15 hr after administration. No significant changes were observed at 100 mg/kg 1,3-dichloropropene. Piperonyl butoxide pretreatment significantly suppressed the elevation of glutamate oxaloacetate transaminase and glutamate pyruvate transaminase activities caused by 300 mg/kg 1,3-dichloropropene. This pretreatment significantly increased 1,3-dichloropropene concn in the liver. The piperonyl butoxide pretreatment decreased cytochrome p450 content in liver microsomes but prevented further reduction of cytochrome p-450 after 1,3-dichloropropene treatment. With buthionine sulfoximine pretreatment plasma glutamate oxaloacetate transaminase activity significantly increased in animals receiving 100 mg/kg 1,3-dichloropropene, whereas liver glutathione content and glutathione-S-transferase activity decreased. This pretreatment also significantly increased 1,3-dichloropropene concn in the liver. Cysteine administered 2 hr after 1,3-dichloropropene treatment by which time 1,3-dichloropropene in the liver had disappeared did not decrease the cytochrome p-450 content induced by 1,3-dichloropropene, although it prevented the elevation of glutamate oxaloacetate transaminase and glutamate pyruvate transaminase activities and increased hepatic glutathione concn. These results suggest 1,3-dichloropropene is biotransformed via cytochrome p450, the metabolites induced liver damage and glutathione plays an important role in the detoxification of 1,3-dichloropropene.

Whole body: 1-2 days; [TDR, p. 518]

A urinary excretion half-life of approximately 5.5 hours for DCP in rats and mice was calculated.

In rats, the initial elimination half-life for 1,3-dichloropropene in blood ranged from 3 to 27 minutes depending on dose. 1,3-Dichloropropene mercapturic acid metabolites have urinary elimination half-lives of approximately 5 hours.

(14)C-1,3-dichloropropene ((14)C-DCP) is rapidly absorbed and eliminated in both the male F344 rat and B6C3F1 mouse following oral administration of 1 or 50 mg/kg (rat) or 1 or 100 mg/kg (mouse). It is extensively metabolized in both species. Urinary excretion was the major route of elimination, accounting for 50.9-61.3 and 62.5-78.6% of the administered dose in rat and mouse, respectively. Urinary elimination half-lives ranged from 5 to 6 hr (rat) and from 7 to 10 hr (mouse). ...

Following absorption, both isomers of 1,3-dichloropropene were, at less than or equal to 300 ppm exposure levels, rapidly eliminated from the bloodstream (3-6 min half-life). In addition, data obtained in rats exposed to 300 ppm 1,3-dichloropropene revealed that this rapid elimination phase was followed by a slower elimination phase having a 33-34 min half-life. Rats exposed to 900 ppm vapors also eliminated 1,3-dichloropropene in a biphasic manner; however, in this case the blood half-life of 1,3-dichloropropene during the initial phase of excretion was 14 to 27 min.

Studies of hepatic toxicity in mice suggest that ingested 1,3-dichloropropene is biotransformed via cytochrome P-450, with metabolites inducing liver damage, and that glutathione plays an important role in the detoxification of 1,3-dichloropropene.

The major urinary metabolite in rats given 1,3-dichloro-2-propene was a mercapturic acid.

(14)C-1,3-dichloropropene ((14)C-DCP) is rapidly absorbed and eliminated in both the male F344 rat and B6C3F1 mouse following oral administration of 1 or 50 mg/kg (rat) or 1 or 100 mg/kg (mouse). It is extensively metabolized in both species. Urinary excretion was the major route of elimination, accounting for 50.9-61.3 and 62.5-78.6% of the administered dose in rat and mouse, respectively. Urinary elimination half-lives ranged from 5 to 6 hr (rat) and from 7 to 10 hr (mouse). Elimination via feces or as (14)CO2 accounted for 14.5-20.5 and 13.7-17.6% of the administered dose, respectively. Metabolites arising from glutathione conjugation account for 36-55 and 48-50% of the administered dose in excreted from rats and mice, respectively. Hydrolysis of the 3-chloro moiety of DCP accounted for 24-37 and 29% of the dose administered to rats and mice, respectively. Two novel dimercapturic acid conjugates were also identified at low levels that might arise via initial hydrolysis of DCP or of epoxidation of DCP-glutathione conjugate or of DCP itself. Structural confirmation of these dimercapturates was obtained via analysis of deuterium retention from D4-DCP in the male F344 rat. Only quantitative differences are seen between the overall metabolic profile of DCP in these two species.

1,3-Dichloropropene (1,3-DCP) is used as a soil nematocide worldwide. Technical grade 1,3-DCP is genotoxic/mutagenic and carcinogenic. /A previous study/ reported that mutagenic activity is lost after purification of 1,3-DCP samples via silica gel column chromatography. We found that mutagenicity and SOS repair in Escherichia coli, strain PM 21, are strongly reduced after purification via silica gel and that mutagenicity and induction of SOS repair depend on oxidative impurities and secondary products. Both isomers (E and Z) of 1,3-DCP are oxidized to 1,3-dichloropropene epoxide (1,3-DCP-Ox). The epoxide is subjected to rapid internal rearrangement to 2,3-dichloropropanal (2,3-DCPA), which spontaneously eliminates HCl and forms the extremely mutagenic, genotoxic, and carcinogenic 2-chloroacrolein (alpha-chloroacrolein) alpha-ClA. Thus, the genotoxic/mutagenic effects of unpurified 1,3-DCP samples mainly depend on alpha-ClA. The underlying genotoxic and mutagenic mechanism is formation of promutagenic exocyclic 1,N(2)-propanodeoxyguanosine adducts of alpha-ClA. Pure 1,3-DCP samples have only a very low S(N)1 reactivity as measured in trifluoroacetic acid solvolysis reactions, hydrolysis, and computed reactivities but possess a moderate S(N)2 reactivity as determined in alkylation tests with the nucleophiles 4-(p-nitrobenzyl)pyridine (NBP) and N-methyl-mercaptoimidazole (MMI). Evidently, the low S(N)1 reactivity is not sufficient to form necessary amounts of O(6)-alkylguanine DNA adducts required for back-mutation in Salmonella typhimurium strain TA1535. The S(N)2 reactivity may, however, lead to other DNA adducts, e.g., N7-guanine adducts, which can induce error prone repair in S. typhimurium strain TA100 and thus lead to back-mutation in this strain. Application of 1,3-DCP samples in agriculture must be considered as a mutagenic risk because the samples can be oxidized and form the extremely mutagenic alpha-ClA. As a consequence, it is questionable whether any stabilizers can prevent oxidation during application.

For more Metabolism/Metabolites (Complete) data for 1,3-DICHLOROPROPENE (12 total), please visit the HSDB record page.

The major metabolic pathway is rapid conjugation with glutathione, resulting in the formation of a mercapturic acid metabolite that is excreted in the urine. Cis-1,3-Dichoropropene may also undergo hydrolysis and dechlorination to form 1-chloroallyl alcohol, an intermediate that reacts with alcohol dehydrogenase to form 1-chloroacrolein. Another minor pathway involves reaction with cytochrome P450 to form mutagenic cis and trans epoxides that convert to the mutagen 3-chloro2- hydroxy-propanal. Conjugation with glutathione can occur in the nasal tissue, kidney, and liver. The glutathione conjugate of cis-1,3-dichloropropene is then converted to the mercapturic acid and acetylated for excretion as the N-acetyl-cysteine metabolite. Alternative metabolic pathways for cis-1,3-dichloropropenes have also been proposed. reaction with cytochrome P-450 resulted in the formation of cis-1,3-dichloropropene epoxides. The cis-1,3-dichloropropene epoxides undergo hydrolysis, possibly catalyzed by epoxide hydrolase, to 3-chloro-2-hydroxypropanal (L893).

Inhalation studies with both humans and rats have shown that dichloropropene (DCP) is readily absorbed, conjugated with glutathione (GSH) via glutathione S-transferase (GST), and rapidly excreted in the urine as N-acetyl-S-(cis-3-chloroprop-2-enyl)-cysteine (3CNAC), a mercapturic acid metabolite. A study of six male volunteers exposed at 1 ppm commercial Telone II (50.6% cis-isomer, 45.2% trans-isomer) for 6 hours found the absorption of cis-DCP was 72% to 80%, while the absorption of trans-DCP was 77% to 82%. A similar percent absorption was found in rats exposed at 136 mg/cu m DCP for 3 hours. DCP does not bioaccumulate in the body. Half-lives were similar for both rats and humans for removal from the blood and for excretion of mercapturic acid metabolites. /A study/ found that the concentration of DCP in expired air and concentration in blood plateaued in the first hour of exposure and declined rapidly postexposure to nondetectable levels in less than an hour. A urinary excretion half-life of approximately 5.5 hours for DCP in rats and mice was calculated. Radio-labeled DCP, when dosed orally in rats, yielded 82% to 84% of the radioactivity in the urine within 24 hours after treatment. Most of this (14)C (92%) was present as N-acetyl-S-((Z), 3-chloroprop-2-enyl) cysteine (Z)-DCP mercapturic acid). Within 4 days, about 1% of the dose of each isomer was found in the carcass.

... /Some/ studies have concluded that urine collection during and after exposure may be representative of exposure to dichloropropene (DCP). Urinary excretion of thioethers was measured in 12 applicators occupationally exposed to DCP and was compared to excretion of the mercapturic acid metabolites. The 8-hour time weighted average exposures to the Z-isomer and the E-isomer of DCP ranged from 0.3 to 18.9 mg/cu m over 1- to 11-hour shifts. Cumulative urinary thioether excretions and urinary postshift levels minus preshift levels correlated well with DCP exposures. Mean urinary thioether concentrations were 1.38-fold greater than the mean DCP mercapturic acid metabolite concentration, suggesting the presence of an unidentified thioether metabolite. The thioether assay correlated well with relatively high DCP exposures.

Studies conducted on occupational and non-occupational exposure to dichloropropene (DCP) in the Dutch flower bulb culture industry found a strong correlation between inhalation exposure and the complete cumulative urinary excretion of the mercapturic acids of DCP. A possible subclinical nephrotoxic effect of subchronic DCP exposure was noted. There was a notable decrease of glutathione and GST activity in blood, suggesting that DCP exposure may affect the glutathione conjugating capacity.

In /a/ personal air monitoring study of 15 applicators of dichloropropene (DCP), excretion of the DCP metabolite, 3CNAC, and excretion of the renal tubular enzyme, NAG [N-acetyl glucosaminidase], were studied. Four workers had clinically elevated NAG in all of their urine collections after baseline. Nine workers showed greater than 25% increases in NAG excretion when compared to baseline. Dichloropropene air exposure products of >700 mg/min/cu m or excretion of >1.5 mg 3CNAC/day distinguished abnormally high daily excretion of NAG. These data indicate a positive relationship between air exposure and internal exposure and a possible subclinical nephrotoxic effect in workers. In a subsequent study using these same urine samples collected during five consecutive 6- to 8-hour intervals and stored frozen for 4 years, /the authors/ analyzed the samples for albumin and retinal binding protein (RBP). Urinary excretion of albumin and RBP during the second through fifth collection intervals was not significantly increased relative to the baseline period after correction for creatinine. Within each interval, excretion of albumin and RBP was significantly correlated with each other and the 3CNAC concentrations. NAG excretion was slightly increased in nine subjects. When the 3CNAC excretion data were dichotomized into subjects excreting less than and more than 1.5 mg/day, which corresponded to low and high DCP exposures, urinary excretion of NAG and RBP was significantly lower in the low exposure than in the high exposure group. Urinary albumin excretion was similar in both groups. Urinary excretion of RBP and albumin during the baseline period correlated best with 24 hours cumulative excretion of these proteins as indicated by logistic regression analysis. Excretion of NAG during the afternoon shift correlated best with 24-hour cumulative NAG excretion. Urinary 3CNAC excretion during the next morning correlated best with its 24-hour cumulative excretion. The conclusion made was that under the conditions used by pesticide applicators, DCP has only a slight effect on the kidney.

For more Absorption, Distribution and Excretion (Complete) data for 1,3-DICHLOROPROPENE (12 total), please visit the HSDB record page.

1,3-Dichloropropene is the predominant component of several formulations used in agriculture as soil fumigants for parasitic nematodes.

Used as a soil fumigant and in organic synthesis; [ACGIH] 1,3-Dichloropropene is a mixture of cis and trans isomers used as a nematicide to fumigate soil before planting; [Reference #1]

Use as fumigant suspended by EPA due to toxicity. [Sullivan, p. 1053]

For 1,3-dichloropropene (USEPA/OPP Pesticide Code: 029001) ACTIVE products with label matches. /SRP: Registered for use in the USA but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Organic synthesis, soil fumigants.

Soil fumigant; nematocide. In manufacture of pesticides.

Two known mutagens, epichlorohydrin and 1,3-dichloro-2-propanol have been identified as impurities in some formulations.

Other chlorinated hydrocarbons may be present as impurities and stabilizers. These include chloropicrin, isomers of dichloropropene, dichloropropane, and epichlorohydrin. /1,3-Dichloropropene mixture/

2,3-Dichloropropene may be present at up to 6.5%

2023: 25,000,000 - <75,000,000 lb

(1974) 9.1X10+9 G

(1983) 1.63X10+10 g

1-Propene, 1,3-dichloro- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 1-Propene, 1,3-dichloro-. National Production Volume: Withheld.

IT IS USED AS A NEMATOCIDE (SOIL FUMIGANT) AS FOLLOWS: 80% ON SUGAR BEETS; 8% ON TOBACCO; 7% ON POTATOES; 5% ON TOMATOES & PEACH TREES (1975)

Soil fumigant for use on cotton and potatoes-48%; vegetables, tobacco and sugar beets-38%; floral, ornamental, treefruits, turf, misc crops-14% (1984)

The California State Department of Agriculture reported that in 1971 approximately 1,285 metric tons of pesticide containing 1,3-dichloropropene were used in that state.

(1995) 17-19.5X10+6 kg active ingredient.

Usual industrial prepn is from 1,3-dichloro-2-propanol by dehydration with POCl3 /phosphorus oxychloride/ or with P2O5 /phosphorus pentaoxide/ in benzene.

Prepd from 1,2,3-trichloropropane with NaOH, ... from 3-chloro-2-propen-1-ol with PCl3; ... from acrolein with PCl5.

Made by the high temperature chlorination of propylene to yield allyl chloride as a primary product. The 1,3-dichloropropene is separated from the heavy ends after removal of allyl chloride as an overhead product in distillation. /1,3-Dichloropropene mixture/

Propylene + chlorine (high-temperature chlorination; by-product of allyl chloride production)

Pic-Clor 60 (Soil Chemicals Corporation): Active ingredient: Telone 39.0%; Chloropicrin 59.6%.

Pic-Clor 15 (Soil Chemicals Corporation): Active ingredient: Telone 82.9%; Chloropicrin 14.9%.

Pic-Clor 30 (Soil Chemicals Corporation): Active ingredient: Telone 68.3%; Chloropicrin 29.8%.

Pic-Clor 40 EC (Soil Chemicals Corporation): Active ingredient: Telone 55.6%; Chloropicrin 37.8%.

For more Formulations/Preparations (Complete) data for 1,3-DICHLOROPROPENE (30 total), please visit the HSDB record page.

Pesticide, Fertilizer, and Other Agricultural Chemical Manufacturing

1-Propene, 1,3-dichloro-: ACTIVE

1,3-Dichloropropene (introduced in 1956 as a pesticide) is marketed as a mixture containing the inactive 1,2-dichloropropane, or as the pure active substance (mixture of E and Z isomers). Dichloropropene is used purely as a soil fumigant nematicide (the Z isomer is more effective than the E isomer) and is used pre-planting to control most species of nematode in deciduous fruit and nuts, citrus fruit, berry fruit, vines, strawberries, and many other crops. The U.S. EPA has recommended it as an alternative to ethylene dibromide.