(E)-1,3-Dichloropropene

Pesticides -> Fumigants

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

log Kow= 2.03

2.04

CHLOROFORM-LIKE ODOR

Sharp, sweet, penetrating odor /1,3-Dichloropropene/

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

1.224 @ 20 °C/4 °C

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

Sol in ether, benzene, chloroform

In water, 2,800 mg/l @ 25 °C.

2800 mg/L @ 20 °C (exp)

234 °F at 760 mmHg (NTP, 1992)

112 °C

112.00 °C. @ 760.00 mm Hg

34 mmHg at 77 °F (NTP, 1992)

34.0 [mmHg]

34 mm Hg @ 25 °C

This chemical does not meet GHS hazard criteria for 4.8% (1 of 21) of reports.

Danger

H226 (28.6%): Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P262, P264, P264+P265, P270, P272, P273, P280, P301+P316, P301+P317, P302+P352, P303+P361+P353, P305+P351+P338, P316, P318, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P370+P378, P391, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 21 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/12976

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

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, acute gastrointestinal distress with pulmonary congestion and edema. It may also cause injury to the liver, kidneys and heart.

A skin, eye, and respiratory tract irritant; May cause burns and lacrimation; May cause injury to liver, kidneys, and heart; [Merck Index] A strong irritant; May cause lacrimation, severe respiratory distress, CNS depression, and GI distress with pulmonary congestion and edema; May cause liver, kidney, and heart damage; [CAMEO] May cause irritation; Targets kidneys and liver; [MSDSonline] See 1,3-Dichloropropene. See Dichloropropene, all isomers.

NTP; TOXICOLOGY AND CARCINOGENESIS STUDIES OF TELONE II P.24 (1985) REPORT # 269, NIH PUB # 85-2525.

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 TRANS-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 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 TRANS-1,3-DICHLOROPROPENE (6 total), please visit the HSDB record page.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. All contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

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/

For more Preventive Measures (Complete) data for TRANS-1,3-DICHLOROPROPENE (11 total), please visit the HSDB record page.

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)

The cis- and trans- isomers of 1,3-dichloropropene, in confirmation of previous reports, caused dose dependent increases in the numbers of reverse mutations in Salmonella typhimurium TA100 in the presence and absence of an S9 fraction in the livers of Aroclor treated rats. cis-1,3-Dichloropropene is efficiently detoxified in mammals by the operation of a glutathione dependent S-alkyl transferase. It is possible that such detoxification could proceed only very slowly in the microbial assays because the concn of glutathione could be severely rate limiting even in those assays fortified by the addition of S9. A dramatic reduction in the microbial mutagenicity in both cis- and trans-1,3-dichloropropene was observed when the concn of glutathione in the microbial mutagenicity assays was adjusted to a normal physiological concn (5 mM). This protective action of glutathione was at least as effective in the absence of S9 as in its presence, suggesting that it was not mediated by mammalian glutathione transferase. There appears to be little or no glutathione alkyl or aryl transferase in the cytosol of Salmonella typhimurium, however intracellular glutathioine is present at a concn similar to that found in mammalian cells. Since the uncatalyzed reaction between the 1,3-dichloropropene and glutathione is relatively slow the effect is not due simply to their destruction by glutathione. A physiological concn of extracellular glutathione could maintain the intracellular glutathione in a reduced form in which its nucleophillic thiol group competes with the nucleophillic centers in the bacterial DNA for the haloalkenes.

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), an average Koc value of 28 determined from data on 3 soils(2) indicates that trans 1,3-dichloropropene is expected to have very high mobility in soil(SRC). Volatilization of trans-1,3-dichloropropene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 8.7X10-4 atm-cu m/mole(4). The potential for volatilization of trans-1,3-dichloropropene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 34 mm Hg(5). The neutral hydrolysis half-life of trans-1,3-dichloropropene was reported as 51, 11 and 3.1 days at 10 °C, 20 °C and 30 °C, respectively(5). This data suggests that hydrolysis may be an important fate process in moist soils(SRC). The half-life of 1,3-dichloropropene (cis and trans isomers) in 13 aerobic soils at 20 °C ranged from 6-17 days(6). The average half-life in anaerobic soils was reported as 8.4 days at 15 °C and 2.4 days at 25 °C(6).

AQUATIC FATE: Based on a classification scheme(1), an average soil Koc value of 28(2), indicates that trans-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 8.7X10-4 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 2 hours and 4.5 days, respectively(SRC). The volatilization half-life of 1,3-dichloropropene (mixture of cis- and trans-isomers) from a stirred beaker of water 6.5 cm deep was 31 min(5). According to a classification scheme(6), an estimated BCF of 7(SRC), from a log Kow of 2.03(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation data in soils under aerobic and anaerobic conditions(7) suggest that trans-1,3-dichloropropene will also biodegrade in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), trans-1,3-dichloropropene, which has a vapor pressure of 34 mm Hg at 25 deg(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase trans-1,3-dichloropropene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals and ozone molecules. The half-life for this reaction in air with hydroxyl radicals is estimated to be 1.5 days(SRC), calculated from its rate constant of 1.4X10-11 cu cm/molecule-sec at 25 deg(3). The half-life for this reaction in air with ozone is estimated to be 76 days(SRC), calculated from its rate constant of 1.5X10-19 cu cm/molecule-sec at 25 deg(3). The degradation products observed from the reaction of trans-1,3-dichloropropene with hydroxide radicals were formyl chloride and chloroacetaldehyde(4).

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 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).

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/

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.

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 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. 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. 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 under- went 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 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 major metabolic pathway is rapid conjugation with glutathione, resulting in the formation of a mercapturic acid metabolite that is excreted in the urine. Trans-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 trans-1,3-dichloropropenes have also been proposed. reaction with cytochrome P-450 resulted in the formation of trans-1,3-dichloropropene epoxides. The trans-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 body weight cis- or trans-2-(14)carbon-1,3-dichloropropene to rats, 80% of the radioactivity of the cis-isomer and 57% of the radioactivity of the trans-isomer was 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 and 23-24% of the trans-isomer were expired as (14)carbon carbondioxide; exhalation of other radioactive compounds was minor. Little fecal excretion was observed. Recovery of both isomers was about 90%.

... Rats were fed (14)carbon-labeled ... isomers of 1,3-dichloropropene and showed differences in their metabolism. With all compounds, 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.

Tomato plants absorbed labeled cis- and trans-1,3-dichloropropene through their roots with max 1,3-dichloropropene absorbed and translocated after 2-4 hr and no 1,3-dichloropropene detected by 48 hr. 1,3-Dichloropropene was metabolized to trans-3-chloroallyl alcohol, part of which was converted to trans-3-chloroacrylic acid and 3-chloropropanol. At 12 and 24 hr after treatment both cis-1,3-dichloropropene and trans-1,3-dichloropropene disrupted the organellar structure of the chloroplasts and the rough endoplasmic reticulum of some plants. However, despite the disruption of normal cellular structure, cis-1,3-dichloropropene and trans-1,3-dichloropropene do not present residue problems and cause concern about their residue fate.

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

For more Absorption, Distribution and Excretion (Complete) data for TRANS-1,3-DICHLOROPROPENE (7 total), please visit the HSDB record page.

1,3-Dichloropropene is a mixture of cis and trans isomers used as a nematocide to fumigate soil before planting; [Reference #1]

Farming (Pesticides) [Category: Industry]

Used primarily in soil fumigants for nematodes or as component of soil fumigant mixtures /for nematodes/.

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

Mixture of equal quantities of (E)- and (Z)-isomers /1,3-Dichloropropene/

1,3-DICHLOROPROPENE TRANS-ISOMER, 45.9%; CIS-ISOMER, 41.6%; 1,2-DICHLOROPROPANE, 2.5%; TRICHLOROPROPENE ISOMER, 1.5%; EPICHLOROHYDRIN, 1.0%; OTHER IMPURITIES 7.5% /TELONE II/