(Z)-1,3-Dichloropropene

Pesticides -> Fumigants

Volatile Organic Compound (VOC) (Pesticide/Volatile Organic Compound (VOC))

log Kow = 2.06

2.06

CHLOROFORM-LIKE ODOR

Sharp, sweet, penetrating irritating odor

1.217 at 68 °F (NTP, 1992) - Denser than water; will sink

1.224 @ 20 °C

less than 1 mg/mL at 68.9 °F (NTP, 1992)

Sol in ether, benzene, and chloroform

Miscible with hydrocarbons, halogenated solvents, esters, and ketones

In water, 2,700 mg/l @ 25 °C.

219.7 °F at 760 mmHg (NTP, 1992)

104.3 °C

43 mmHg at 77 °F (NTP, 1992)

28.0 [mmHg]

26.3 mm Hg @ 20 °C

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 (99.7%): 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)

SYMPTOMS: Symptoms of exposure to this compound may include local irritation of the eyes skin and respiratory tract; dermatitis, gasping, coughing, substernal pain, extreme respiratory distress, lacrimation, central nervous system depression, skin irritation, acute gastrointestinal distress with pulmonary congestion and edema. It also may cause injury to the liver, kidneys and heart.

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; Ambient Water Quality Criteria Doc: Dichloropropanes/Dichloropropenes (Draft) (1980)

WHO: Environmental Health Criteria 146: 1,3-Dichloropropene, 1,2-Dichloropropane and Mixtures (1993)

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Dichloropropenes/

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Dichloropropenes/

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Dichloropropenes/

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Dichloropropenes/

For more DOT Emergency Guidelines (Complete) data for CIS-1,3-DICHLOROPROPENE (8 total), please visit the HSDB record page.

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.

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical 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/

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/

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for CIS-1,3-DICHLOROPROPENE (6 total), please visit the HSDB record page.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/

For more Preventive Measures (Complete) data for CIS-1,3-DICHLOROPROPENE (10 total), please visit the HSDB record page.

Intermediate Inhalation: 0.008 ppm (Rabbit) (L893) Chronic Inhalation: 0.007 ppm (Rabbit) (L893)

Intermediate Inhalation: 0.008 ppm (Rabbit) (L893) Chronic Inhalation: 0.007 ppm (Rabbit) (L893)

1.0 [ppm]

8 hr Time Weighted Avg (TWA) 1 ppm, skin. /1,3-Dichloropropene/

Excursion Limit Recommendation: Excursions in worker exposure levels may exceed 3 times the TLV-TWA for no more than a total of 30 minutes during a work day, and under no circumstances should they exceed 5 times the TLV-TWA, provided that the TLV-TWA is not exceeded. /1,3-Dichloropropene/

A3: Confirmed animal carcinogen with unknown relevance to humans. /1,3-Dichloropropene/

RECOMMENDED RESPIRATOR: When working with this chemical, wear a NIOSH-approved full face chemical cartridge respirator equipped with the appropriate organic vapor cartridges. If that is not available, a half face respirator similarly equipped plus airtight goggles can be substituted. However, please note that half face respirators provide a substantially lower level of protection than do full face respirators. (NTP, 1992)

PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

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)

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).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values from 20 to 42 for 1,3-dichloropropene (isomers not specified)(2), indicate that cis-1,3-dichloropropene is expected to have very high mobility in soil(SRC). Volatilization of cis-1,3-dichloropropene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.7X10-3 atm-cu m/mole(3). The potential for volatilization of cis-1,3-dichloropropene from dry soil surfaces exists(SRC). Approx 25% of field applied 1,3-dichloropropene had volatilized by 14 days post-treatment (the final sampling interval)(2). cis-1,3-Dichloropropene biodegrades rapidly in soil under aerobic and anaerobic conditions(2). Under aerobic conditions, half-life for 1,3-dichloropropene (isomer not specified) was 12 days in Catlin silt loam soil (2). The major nonvolatile degradates isolated from the soil were cis/trans-3-chloroprop-2-en-1-ol (3-chloroallyl alcohol) and cis/trans-3-chloroprop-2-enoic acid (3-chloroacrylic acid)(2). Under anaerobic conditions at 25 °C in both a silty clay loam and sandy loam soil, the half-life was 2.4 days(2). The field dissipation half-life of 1,3-dichloropropene applied at 345 lb ai/acre was one day, and a second half-life of approx seven days, in the surface 24-in of a bare-ground loamy sand soil(2).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 20 to 42 for 1,3-dichloropropene (isomers not specified)(2), indicate that cis-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 2.7X10-3 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 1.3 and 102 hours, respectively(SRC). According to a classification scheme(5), a BCF of 8(SRC), from its log Kow of 2.06(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). cis-1,3-Dichloropropene degrades rapidly by chemical hydrolysis; in buffered solutions at pH values of 5, 7, 9, the half-life of 1,3-dichloropropene (isomer not specified) was 13.5 days at 20 °C(2). cis-1,3-Dichloropropene rapidly biodegrades in soil under aerobic and anaerobic conditions(2) and is expected to in water based upon these studies(SRC). Under aerobic conditions, half-life for 1,3-dichloropropene (isomer not specified) was 12 days in Catlin silt loam soil(2). The major nonvolatile degradates isolated from the soil were cis/trans-3-chloroprop-2-en-1-ol (3-chloroallyl alcohol) and cis/trans-3-chloroprop-2-enoic acid (3-chloroacrylic acid)(2). Under anaerobic conditions at 25 °C in both a silty clay loam and sandy loam soil, the half-life was 2.4 days(2).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cis-1,3-dichloropropene, which has a vapor pressure of 26 mm Hg at 20 °C(2) is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase cis-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 46 hours(SRC), calculated from its rate constant of 8.4X10-12 cu cm/molecule-sec at 25 °C(3).

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

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

IDENTIFICATION: 1,3-Dichloropropene is a colorless to amber colored liquid with a penetrating, irritating, chloroform-like odor. It has been widely used in agriculture as a pre-plant soil fumigant for the control of nematodes in vegetables, potatoes, and tobacco. It often appears as part of a mixture also including 1,2-dichloropropane. Application is primarily by soil injection. In water, 1-3-dichloropropene is likely to disappear rapidly, because of its relatively low water solubility and high volatility. HUMAN EXPOSURE: The exposure of the general population through air, water, or food is unlikely. Occupational exposure is likely to be through inhalation and via the skin. Irritation of the eyes and the upper respiratory mucosa appears promptly after exposure. Dermal exposure caused severe skin irritations. Inhalation may result in serious signs and symptoms of poisoning with lower exposures resulting in depression of the central nervous system and irritation of the respiratory system. Some poisoning incidents have occurred in which persons were hospitalized with signs and symptoms of irritation of the mucous membrane, chest discomfort, headache, nausea, vomiting, dizziness and, occasionally, loss of consciousness and decreased libido The fertility status of workers employed in the production of chlorinated three-carbon compounds was compared with a control group. There was no indication of an assocation between decreased fertility and exposure. ANIMAL STUDIES: The acute oral toxicity of 1,3-dichloropropene in animals is moderate to high. Acute dermal exposure is moderately toxic. Acute intoxication showed central nervous and respiratory system involvement. Severe reactions were seen in rabbit skin and eye irritation tests. Degeneration of the olfactory epithelium and hyperplasia were seen in inhalation studies with mice and rats. Cis- and trans-1,3-dichloropropene and mixtures were mutagenic in bacteria with, and without, metabolic activation. In mice, increased incidences of hyperplasia of the urinary bladder, the forestomach, and the nasal mucosa were observed. There was an increase in the incidence of benign lung tumors. Some toxic changes in the olfactory mucosa of the nasal cavity were also seen in rats, but no increase in tumor incidence. The major metabolic route of elimination of 1,3-dichloropropene is via conjugation with glutathione.

The primary toxic effects of cis-1,3-dichloropropene are portal-of-entry effects resulting from the chemical reactivity of the compound and its physicochemical properties. Repeated irritation results in a hyperplastic response in the target tissues. The mutagenicity of cis-1,3-dichloropropene is attributed to its biotransformation by cytochrome P-450 to stereospecific epoxides and the hydrolysis product, 3-chloro-2-hydroxypropanal. It is likely that depletion of glutathione would block the major detoxification pathway for cis-1,3- dichloropropene, resulting in increased toxicity of organs such as the liver and kidney because of binding of reactive intermediates to macromolecules in cells. There is some evidence that cytotoxicity of hepatic cells exposed to cis-1,3-dichloropropene is preceded by increased levels of phospholipid hydroperoxides (L893).

The primary toxic effects of trans-1,3-dichloropropene are portal-of-entry effects resulting from the chemical reactivity of the compound and its physicochemical properties. Repeated irritation results in a hyperplastic response in the target tissues. The mutagenicity of trans-1,3-dichloropropene is attributed to its biotransformation by cytochrome P-450 to stereospecific epoxides and the hydrolysis product, 3-chloro-2-hydroxypropanal. It is likely that depletion of glutathione would block the major detoxification pathway for trans-1,3dichloropropene, resulting in increased toxicity of organs such as the liver and kidney because of binding of reactive intermediates to macromolecules in cells. There is some evidence that cytotoxicity of hepatic cells exposed to trans-1,3-dichloropropene is preceded by increased levels of phospholipid hydroperoxides (L893).

Symptoms occuring after inhalation include gasping, refusal to breathe, coughing, substernal pain; lacrimation and headache are prominant. After inhalation exposures, malaise, headache, chest and abdominal discomfort and irritability can persist during weeks or years. Moreover, Irritation of eyes and upper respiratory mucosa appears promptly after exposure to concentrated vapors. Ingestion can cause cough, sore throat, headache, dizziness, nausea, vomiting, unconsciousness, and laboured breathing (T48, L893).

Symptoms occuring after inhalation include gasping, refusal to breathe, coughing, substernal pain; lacrimation and headache are prominant. After inhalation exposures, malaise, headache, chest and abdominal discomfort and irritability can persist during weeks or years. Moreover, Irritation of eyes and upper respiratory mucosa appears promptly after exposure to concentrated vapors. Ingestion can cause cough, sore throat, headache, dizziness, nausea, vomiting, unconsciousness, and laboured breathing (T48, L893).

cis-1,3-Dichloropropene was detected in 1 out of 5 samples of municipal landfill leachate from Wisconsin; the concn of the positive sample was 18 ppb(1). Influent of a textile wastewater plant contained 2 ppb of cis-1,3-dichloropropene while effluent from the plant contained 6 ppb(2). In 1978, cis-1,3-dichloropropene was detected in treated effluent from seven petroleum refineries at concns ranging from <0.1 to <0.7 ug/l(3).

PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/

The calculated Freundlich adsorption coefficients (Kd) for 1,3-dichloropropene (isomers not specified) were 0.23 and 0.32 for loamy sand and sand soils, respectively(1); Kd was 0.49 and 1.09 for clay soils(1). The avg max Koc values were 20 for sand, 25 for loamy sand, and 41 and 42 for two clay soils(1). The avg Koc of cis-1,3-dichloropropene in 3 soils with organic carbon contents of 3.19, 10.4, and 55.1% was 27(2). According to a classification scheme(3), Koc values from 25 to 42 suggest that cis-1,3-dichloropropene is expected to have very high mobility in soil(SRC). In 30-cm columns of sand, loamy sand, and Florida clay, 1,3-dichloropropene (isomers not specified) leached when more than 25 inches of water were applied(1); a total of 1.9% to 4.6% of the applied (unaged) radioactivity remained in the soils and 70% to 84% was found in the leachate(1). Aged (eg, 31 days) 1,3-dichloropropene (isomers not specified) residues were very mobile, with 25.6% to 32.0% of the applied radioactivity in the leachates of 30-cm columns of loamy sand soil(1). 1,3-Dichloropropene (isomers not specified) and the degradates 3-chloroallyl alcohol, chloroacrylic acid, and composite carboxylic acids (including acetic acid, oxalic acid, and propionic acid) were detected in both the leachates and the upper 2-cm soil segment extracts(1).

Molecular orbital calculations were used to clarify the mechanism of mutagenic action of various substituted allyl chlorides. Computed molecular properties were compared with experimental mutagenic potentials of these allylic cmpd. In agreement with the experiment, the computational results suggest that the primary mechanism of action involves the SN1 formation of allylic cations whih then react with nucleophilic centers of nucleic acid bases. The usefulness of computed propertiee 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.

Detoxication of cis-1,3-dichloropropene ((Z)-DCP) by glutathione conjugation was studied in the rat. 2 rats were given an oral dose of 20 mg/kg radiolabeled cis-dichloropropene. Urine & feces were collected daily for 2 days & analyzed for radioactivity. In the urine, 82-84% of the radioactive material was recovered within 24 hr. Most of this material was present as N-acetyl-S-cis-3-chloroprop-2-enyl)cysteine. When cis-dichloropropene was incubated with glutathione & rat liver cytosol, 81% was recovered in 10 min. The product of the in vitro reaction was S-(cis-3-chloroprop-2-enyl) glutathione. The presence of glutathione in cytosol & liver supernatant was necessary to remove cis-dichlopropene the /results indicate/ that the rapid elimination of radioactivity from rats dosed with radiolabeled cis-dichloropropene is due to an efficient glutathione dependent biotransformation.

It has been shown that a minor metabolic pathway of the cis-1,3-dichloropropene is mono-oxygenase catalyzed oxygenation, leading to the possible formation of the metabolite cis-1,3-dichloropropene-oxide.

Groups of 3-9 male Fischer 344 rats (200-260g) were admin 50 mg cis-1,3-dichloropropene (94.1% cis- & 2.5% trans-) or 50 mg trans-1,3-dichloropropene (97.3% trans- & 0.8 cis-)/kg bw, by gavage. The rats were sacrificed at various intervals after dosing, to determine the tissue non-protein sulfhydryls (NPS) in the liver, kidneys, forestomach, glandular, stomach, & bladder. Blood samples were also taken to determine the presence of unchanged 1,3-dichloropropene. Cis-1,3-dichloropropene was only detected in the blood (6.58 ug/liter) 15 min after dosing, the blood levels of trans-1,3-dichloropropene were 11.72 & 8.38 ug/liter, respectively, 15 & 45 min after dosing. A statistically significant decr in the non-protein sulfhydryl contents of the liver, kidneys, forestomach, & glandular stomach was found. This depletion reached a max, approx 2 hr after dosing. No depletion was noted in the bladder. It is not possible to distinguish the effects of cis- & trans-1,3-dichloropropene on NPS, as the results for the individual isomers were not reported. The results indicated that orally admin 1,3-dichloropropene produces a rapid & significant depletion of tissue non-protein sulfhydryls in the rat.

The biotransformation to sulfur containing products of the Z-isomers & E-isomers of 1,3-dichloropropene administered ip in combination to male Wistar-rats was investigated. The presence of mercapturic acids in the urine of the animals was determined using GC with nitrogen & sulfur selective detection (GC-NDP & GC-FDP, respectively) & GC/MS with negative chemical ionization & single ion detection. Quantification of mercapturic acids in the urine of animals treated with the dichloropropene isomers in doses of 5 ug each, was achieved with the use of GC-NDP & GC-FPD, while GC/negative chemical ionization/MS detected only the mercapturic acids generated by doses = 25 ug or higher, due to the interference of endogenous products. Both products tested are metabolized via glutathione conjugation, with the generation of 2 major mercapturic acid conjugates, & that all three analytical procedures tested are useful for the determination of human exposure to low levels of 1,3-dichloropropene.

The metabolism of cysteine S-conjugates of both cis- and trans-1,3-dichloropropene in the presence of rat kidney microsomes and purified flavin-containing monooxygenase from hog liver was investigated in vitro. Preliminary studies with isolated rat kidney cells demonstrated that cysteine S-conjugates were quite toxic to the cells in a process which was consistent with a role of the flavin-containing monooxygenase in the bioactivation of the nephrotoxins. Putative S-oxide metabolites of cysteine S-conjugates were chemically synthesized, and diastereomers were separated and identified by spectroscopic means. The metabolic products of cysteine S-conjugates were identified by comparing the chemical properties of the metabolites with authentic synthetic cysteine S-conjugate S-oxides. Surprisingly, S-conjugate S-oxygenase activity was not observed with rat kidney microsomes but was present when cysteine S-conjugates were incubated with the highly purified flavin containing monooxygenase from hog liver. The kinetic parameters indicated that considerable S-oxygenase stereoselectivity and structural selectivity was observed: cis cysteine S-conjugates were preferred substrates and N-acetylation of cysteine S-conjugates decreased substrate activity. S-Oxygenation was considerably diastereoselective and diastereoselectivity was much greater for cysteine S-conjugates with higher Vmax values. Cysteine S-conjugate S-oxides were not indefinitely stable, and under certain conditions, the S-oxides underwent a (2,3)-sigmatropic rearrangement to acrolein. Formation of acrolein or other electrophilic products from S-(chloropropenyl)cysteine conjugate S-oxides may contribute to the renal effects observed for S-(chloropropenyl)cysteine conjugates. Thus, cytotoxicity studies with isolated rat proximal tubular cells or LLC-PK1 cells treated with cysteine S-conjugates showed a time and dose-dependent decrease in cell viability. Reduction of renal cytotoxicity of cysteine S-conjugates in the presence of methimazole, an alternate substrate competitive inhibitor of the flavin containing monooxygenase, suggested that this enzyme may contribute to the renal effects of 1,3-dichloropropene.

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).

Following oral admin of 8.3-13.5 mg/kg bw cis- or trans-2-(14)carbon-1,3-dichloropropene to rats, 80% of the radioactivity of the cis-isomer & 57% of the radioactivity of the trans-isomer were excreted in the urine within 24 hr. Little further urinary excretion occurred over the next 72 hr. After 96 hr, 2-5% of the cis-isomer & 23-24% of the trans-isomer were expired as (14)C, Carbon dioxide; exhalation of other radioactive cmpds was minor. Little fecal excretion was observed. Recovery of both isomers was about 90%.

Following the oral admin to rats of (14)carbon-labeled 1,2-dichloropropane, cis-1,3-dichloropropene 2, or trans-1,3-dichloropropene 3, 80-90% of the radioactivity was eliminated in the feces, urine & expired air within the first 24 hr. The urine was the major route of excretion in all 3 cases. ...

... Rats were fed (14)carbon-labeled ... isomers of 1,3-dichloropropene & showed differences in their metab. With all cmpds, 80-90% was eliminated in the first 24 hr. Major route of excretion was in the urine, where ... 56.5% of trans was found. The amount of (14)carbon dioxide excreted was 23.6%, with correspondingly less ... in the urine.

The fate of 14C-cis & 14C-trans-1,3-dichloropropene (97%; 62% cis & 38% trans) was studied after oral dosing of male B6C3F1 mice with 1 or 100 mg/kg bw (3 animals/dose level). Urine, feces expired air, tissues, & remaining carcasses were analyzed after 48 hr. Urine was the major route of excretion, with 63 & 79%, respectively, of the admin doses (1 & 100 mg/kg bw) being excreted over 48 hr. Half-lives for urinary excretion raged from 5-6 hr. Feces & expired /carbon dioxide/ accounted for 15 & 14% of the 14C-radioactivity, respectively. In the carcass, 2% was found. The tissue concns of 14C-activity were highest in the stomach wall, followed in decreasing order by kidneys, liver, bladder, fat, & skin ... .

For more Absorption, Distribution and Excretion (Complete) data for CIS-1,3-DICHLOROPROPENE (9 total), please visit the HSDB record page.

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]

Soil fumigant, nematicide

USED PRIMARILY IN SOIL FUMIGANTS OR AS COMPONENT OF SOIL FUMIGANT MIXTURES; SMALL AMT AS CHEM INTERMEDIATE.

Used as an insecticide and fumigant.

Breathing in contaminated air; drinking contaminated water; eating contaminated food; dermal and eye exposure (L893).

Liquid; mixture of approximately equal quantities of (E)- and (Z)- isomers /1,3-Dichloropropene/

Mixtures: (1,3-dichloropropene +) 1,2-dichloropropane

92-97% pure /Technical/

94% 1,3-dichloropropene (isomers not specified) and 6% inert ingredients /Telone II/

For more Formulations/Preparations (Complete) data for CIS-1,3-DICHLOROPROPENE (7 total), please visit the HSDB record page.