1,2-Dibromo-3-Chloropropane

Hazardous Air Pollutants (HAPs)

Carcinogens

Pesticide -> EPA IRIS

Pesticides -> Fumigants

Volatile Organic Compound (VOC) (Pesticide)

log Kow= 2.96

2.96

PUNGENT ODOR

Pungent odor at high concentrations.

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

2.08 AT 20 °C/20 °C

Relative density (water = 1): 2.1

2.05

1.093 @ 14°C

2.05

less than 0.1 mg/mL at 64 °F (NTP, 1992)

MISCIBLE IN ALIPHATIC AND AROMATIC HYDROCARBONS

MISCIBLE WITH OILS, DICHLOROPROPANE, ISOPROPYL ALCOHOL

0.1% wt/wt in water

Miscible with acetone

In water= 1230 mg/l at 20 °C

CORRODES ALUMINUM, MAGNESIUM, TIN & ALLOYS CONTAINING THESE METALS; ATTACKS RUBBER MATERIAL & COATINGS

Will not corrode steel or copper alloys unless it contains more than 0.02% of water.

170 °F (NTP, 1992)

170 °F (OPEN CUP)

77 °C o.c.

170 °F (open cup)

(oc) 170 °F

385 °F at 760 mmHg (NTP, 1992)

164.5 °C at 300 mm Hg

196 °C

384 °F

196 °C @760 [mm Hg]

384 °F

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P264, P270, P273, P280, P301+P316, P318, P319, P321, P330, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P317, P318, P319, P320, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Hazard Traits - Carcinogenicity; Genotoxicity; Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity; Reproductive Toxicity

Status: Active Update: 13-12-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/11656

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.)

Excerpt from ERG Guide 159 [Substances (Irritating)]:

Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 77 °C explosive vapour/air mixtures may be formed.

1,2-Dibromo-3-chloropropane (DBCP) itself is classified in the USA as a combustible liq in class IIIA; formulations of DBCP incl kerosene or other flammable solvents fall into the flammable range (class IB for formulations made with kerosene).

1,2-Dibromo-3-chloropropane is a manufactured chemical and is not found naturally in the environment. It is a colorless liquid with a sharp smell. It can be tasted in water at very low concentrations. Some industries use it to make another chemical that is used to make materials that resist burning. Large amounts of 1,2-dibromo-3-chloropropane were used in the past on certain farms to kill pests that harmed crops. Farmers in all states other than Hawaii stopped using this chemical in 1979. Hawaii stopped using it in 1985. We do not know exactly how much of it is currently made or used by industry, but it is probably a small amount.

1,2-Dibromo-3-chloropropane (DBCP) was used in the past as a soil fumigant and nematocide on crops; it is no longer used except as an intermediate in chemical synthesis. Acute (short-term) exposure to DBCP in humans results in moderate depression of the central nervous system (CNS) and pulmonary congestion from inhalation, and gastrointestinal distress and pulmonary edema from oral exposure. Chronic (long-term) exposure to DBCP in humans causes male reproductive effects, such as decreased sperm counts. Testicular effects and decreased sperm counts were observed in animals chronically exposed to DBCP by inhalation. Available human data on DBCP and cancer are inadequate. High incidences of tumors of the nasal tract, tongue, adrenal cortex, and lungs of rodents were reported in a National Toxicology Program (NTP) inhalation study. EPA has classified DBCP as a Group B2, probable human carcinogen.

Strong positive data for testicular damage in animals and decreased sperm counts, azoospermia, and hormonal changes in humans; [ATSDR Case Studies # 29] Germ cell mutagens that have shown to increase the mutant frequency in the progeny of exposed mammals. [MAK]

USEPA; Drinking Water Criteria Document: 1,2-Dibromo-3-Chloropropane (1985) EPA/600/X-84/209

Saito-Suzuki R et al; Dominant lethal studies in rats with 1,2-dibromo-3-chloropropane and its structurally related compounds; Mutat Res 101: 321-7 (1982).

USEPA; Health advisories for 16 pesticides (including alachlor, aldicarb, carbofuran, chlordane, DBCP, 1,2-dichloropropane, 2,4-D, endrin, ethylene dibromide, heptachlor/heptachlor epoxide, lindane, methoxychlor, oxamyl, pentachlorophenol, toxaphene and 2,4,5-TP) p.264 (1987). A review on the health effects of 16 pesticides including: DBCP. ... Topics discussed include: general information and properties, pharmacokinetics, health effects in humans and animals, quantification of toxicological effects, other criteria guidance and standards, analytical methods, and treatment technologies.

Aharonsons N; Pure Appl Chem 59 (10): 1419-46 (1987). ... The objectives of this review are to sumarize existing information on the occurrence of pesticides in groundwater and processes resulting in their detection; to identity existing technologies, and to describe missing information needed to make assessments and predicitions. ... Mobility and transformation processes that determine the amount of a pesticide actually reaching groundwater are described. Transformation processes include microbial metabolism and chemical reactions.

For more Special Reports (Complete) data for 1,2-DIBROMO-3-CHLOROPROPANE (9 total), please visit the HSDB record page.

U066; As stipulated in 40 CFR 261.33, when 1,2-dibromo-3-chloropropane, 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).

Excerpt from ERG Guide 159 [Substances (Irritating)]:

Use water spray, powder, foam, carbon dioxide.

Fresh air, rest. Refer for medical attention.

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. 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)

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/

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U066, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

No acceptable chem decontamination for 1,2-dibromo-3-chloropropane is known; destruction by incineration requires dilution with a flammable solvent and passage of the products of burning through scrubbers to remove the hydrogen chloride and hydrogen bromide produced.

Dibromochloropropane is reported to be stable to neutral and acid media. It is hydrolyzed by alkali to 2-bromoallyl alcohol. Controlled incineration with adequate scrubbing and ash disposal facilities. The Manufacturing Chemists Association suggest the following disposal procedures for bromine-containing compounds: - pour onto vermiculite, sodium bicarbonate or a sand-soda ash mixture (90-10). Mix and shovel into paper boxes. Place in an open incinerator. Cover with scrap wood and paper. Ignite with an excelsior train; stay on upwind side or dump into a closed incinerator with afterburner. - Dissolve in a flammable solvent. Spray into the firebox of an incinerator equipped with afterburner and scrubber (alkali). Recommendable methods: Adsorption & incineration. Peer review: Dilute well with hydrocarbon fuel. Adsorb on vermiculite or sodium carbonate. Incinerate with excess non halogenated waste. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

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/

For more Disposal Methods (Complete) data for 1,2-DIBROMO-3-CHLOROPROPANE (12 total), please visit the HSDB record page.

Evacuate danger area! Consult an expert! Personal protection: complete protective clothing including self-contained breathing apparatus. Ventilation. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

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.

Transfers of 1,2-dibromo-3-chloropropane (DBCP) from one container to another should be made through closed systems, with venting back to the original container or through charcoal or other absorptive or destructive arrangement that will prevent escape of DBCP into the occupational environment. No acceptable chem decontamination for DBCP is known; destruction by incineration requires dilution with a flammable solvent and passage of the products of burning through scrubbers to remove the hydrogen chloride and hydrogen bromide produced.

Protective clothing or gear that becomes contaminated should be washed at once with soap or water or discarded. If the odor of 1,2-dibromo-3-chloropropane persists on clothing or protective gear after washing & aeration, the clothing or gear should not be worn.

The material must not be allowed to remain on the skin.

For more Preventive Measures (Complete) data for 1,2-DIBROMO-3-CHLOROPROPANE (18 total), please visit the HSDB record page.

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Single subcutaneous injection of 1,2-dibromo-3-chloropropane (DBCP) produced dose-dependent injury to kidney, testis, epididymis, & liver in male rats. Pretreatment with enzyme inducer phenobarbital reduced the nephrotoxicity & hepatotoxicity of DBCP, & resulting serum creatinine and urea nitrogen concn. Cobaltous chloride pretreatment enhanced the necrogenic effect of DBCP on the kidney & potentiated DBCP-induced elevations of serum creatinine and urea nitrogen concn. The gonadotoxicity of DBCP was enhanced by cobaltous chloride and reduced by phenobarbital. The modulating effects of cobaltous chloride and phenobarbital could not be ascribed simply to changes in tissue concn of the protective conjugation substrate glutathione, since cobaltous chloride incr and phenobarbital did not alter renal & hepatic nonprotein sulfhydryl concn. A complex role of metab is indicated in determining dose-dependent toxic response to DBCP admin.

Body Weight, Cancer, Gastrointestinal (Stomach and Intestines, part of the digestive system), Hepatic (Liver), Neurological (Nervous System), Renal (Urinary System or Kidneys), Reproductive (Producing Children), Respiratory (From the Nose to the Lungs)

Reproductive

Eyes, skin, respiratory system, central nervous system, liver, kidneys, spleen, reproductive system, digestive system

Breathing high levels of 1,2-dibromo-3-chloropropane causes reproductive damage, including reduced sperm counts, birth defects, and infertility. It may also damage the stomach, liver, kidneys, brain, spleen, blood, and lungs, and cause skin and eye damage from direct contact. (L125)

LD50 ANAS PLATYRHYNCHOS (MALLARD) 3-5 MO FEMALES ORAL 66.8 MG/KG (95% CONFIDENCE LIMIT 48.2-92.6 MG/KG) /95% ACTIVE INGREDIENT/

LD50 PHASIANUS COLCHICUS (RING-NECKED PHEASANT) 3-4 MO FEMALES ORAL 156 MG/KG (95% CONFIDENCE LIMIT 89.3-271 MG/KG) /95% ACTIVE INGREDIENT/

TERRESTRIAL FATE: 1,2-Dibromo-3-chloropropane has been applied to various types of agricultural soils in CA by injection, flooding & sprinkling. The chemical was still present 40 wk after application; and its distribution in soil was proportional to size of soil particles, with greatest distribution found in sandy soils & lowest in clay. In field experiments, 1,2-dibromo-3-chloropropane was detected in soil at levels in the mean range of 0.008-1.64 mg/kg from 1 day to 16 wk after application at the rate of 13.75 kg/ha. Volatilization is expected to be the primary fate of DBCP near the soil surface. Leaching to groundwater is also anticipated based on the demonstrated weak adsorption of DBCP to several soils. Hydrolysis in acidic and neutral soils is not expected to be significant, but may be so in alkaline soils. Although biodegradation may also be significant, it is expected to be a slow process relative to leaching and volatilization.

TERRESTRIAL FATE: Based on a recommended classification scheme(1), measured soil Koc values ranging from 40(2)-149(3) indicate that 1,2-dibromo-3-chloropropane will have very high to high mobility in soil(SRC). Clay and silt soils adsorb more 1,2-dibromo-3-chloropropane than sands; however, downward migration of this compound was observed regardless of the soil type(4). 1,2-Dibromo-3-chloropropane has been reported in well water samples(5) indicating that this compound does leach to groundwater. Koc values from 305-355 were measured for aquifer solids(6) suggesting that this compound will have moderate mobility in an aquifer system(6,SRC). Hydrolysis in acidic and neutral soils is not expected to be significant based on an estimated aqueous half-life of 38 years at pH 7(7), but may be so in alkaline soils(8,SRC). 1,2-Dibromo-3-chloropropane volatilized rapidly from soil surfaces where it had been applied in irrigation water; at least 85% of this compound was lost over 42 days in experiments using cyclic water applications meant to mimic citrus irrigation practices(9). However, air levels of this compound above shank injection-treated soil rarely exceeded 1 ppb beyond 1 day post treatment(10).

TERRESTRIAL FATE: Although biodegradation may be an important fate process in soil, it is expected to be a slow process relative to leaching and volatilization(SRC). Persistence of 1,2-dibromo-3-chloropropane was much greater when injected into soils than when applied to soils in irrigation water(1). The most rapid rate of dehalogenation (20% in 1 week) was obtained with pH 8 soil suspensions; the maximum observed dehalogenation was 63% after 4 weeks under unspecified conditions(2). Biodegradation of 1,2-dibromo-3-chloropropane in aerobic soil columns gave half-lives of 6.6, 13.0, and 1130 days for natural, nutrient-enriched, and sterile conditions, respectively(3). In other experiments however, 1,2-dibromo-3-chloropropane was not aerobically degraded in soil over a period of time ranging up to several months(4,5). Soil samples, maintained under anaerobic conditions, transformed 1,2-dibromo-3-chloropropane, at 10 and 100 mg/kg suspension, with 5.6 and 11.6% conversion, respectively, in 28 days(4)

AQUATIC FATE: Based on a recommended classification scheme(1), measured Koc values from 40(2)-149(3) indicate that 1,2-dibromo-3- chloropropane should not adsorb to suspended solids and sediment in water(SRC). Due to the low measured hydrolysis rate at neutral pH (estimated half-life= 38 years at 25 °C and pH 7)(4), volatilization is expected to be the predominant fate of aqueous 1,2-dibromo-3-chloropropane (1,2-dibromo-3-chloropropane) under neutral conditions. In basic solution, however, hydrolysis is expected to compete with volatilization, forming 2-bromoallyl alcohol(5). 1,2-Dibromo-3-chloropropane should volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 1.5X10-4 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(6) and water solubility(6). Estimated volatilization half-lives for a model river and model lake are 14 hours and 9 days, respectively(1,SRC). Photodegradation is not expected to be a major fate process for this compound in water based on experimental results in natural water(7).

For more Environmental Fate (Complete) data for 1,2-DIBROMO-3-CHLOROPROPANE (6 total), please visit the HSDB record page.

/1,2-Dibromo-3-chloropropane (DBCP)/ was detected in carrot peel and pulp in concn of 0.339 and 0.607 mg/kg, respectively. After unpeeled carrots were boiled for 5 min, they still contained 0.251 mg/kg DBCP.

1,2-Dibromo-3-chloropropane residues were measured in peaches harvested from trees growing in fall-fumigated or nonfumigated soil(1). No 1,2-dibromo-3-chloropropane residues were detected in peaches from trees growing on nonfumigated soil or in soil fumigated at or below the previously recommended rate of 46.8 l/ha. An average application rate of 58 and 115 L/treated ha resulted in residues of 0.19 ppb and 0.43 ppb of 1,2-dibromo-3-chloropropane, respectively(1). Foods sampled from the FDA market basket collection contained a mean concentration of 81 and 85 ng/g 1,2-dibromo-3-chloropropane for fatty and non-fatty foods, respectively (out of 5 determinations)(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

Oral (L125) ; inhalation (L125) ; dermal (L125)

U066; As stipulated in 40 CFR 261.33, when 1,2-dibromo-3-chloropropane, 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).

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. 1,2-Dibromo-3-chloropropane 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 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.6 (section IV. D.3.b).

(CA) CALIFORNIA 0.2 ug/l

(HI) HAWAII 0.04 ug/l

(AZ) ARIZONA 0.025 ug/l

(ME) MAINE 0.25 ug/l

ADMIN OF A SINGLE ORAL DOSE OF 1,2-DIBROMO-3-CHLOROPROPANE (DBCP) TO MALE RATS DECR HEPATIC MICROSOMAL CYTOCHROME P450 & B5 TO 45 AND 65% OF CONTROLS AFTER 48 HR. INCORPORATION OF DELTA-AMINOLEVULINIC ACID INTO PROTEIN, MICROSOMES & PROTEASE-TREATED MICROSOMES WAS DECR 88, 65, AND 70% OF RESPECTIVE CONTROL VALUE IN ANIMALS TREATED FOR 12 HR. ACTIVITY OF ALA-DEHYDRATASE ALSO DECR TO 75 AND 90% OF CONTROLS AT 24 AND 48 HR. THESE DATA SUGGEST AN INHIBITION OF HEME SYNTH OR AN ALTERATION IN HEME DEGRADATION MAY PLAY A ROLE IN DECR OF THE MICROSOMAL CYTOCHROMES FOLLOWING TREATMENT WITH DBCP.

Challenge of male rats with a single dose of 1,2-dibromo-3-chloropropane resulted in significant decr in cytochrome p450 in microsomes isolated from liver, kidney, testis, lung, & small intestine mucosa 48 hr after treatment. Lipid peroxidation was not found in hepatic microsomes. In liver tissue, treatment resulted in a decr in cytochrome p450 in both rough & smooth microsomal fractions and nuclei, but not in mitochondrial fractions. Mixed-function oxidase activities in hepatic microsomes decr in parallel with cytochrome p450 content. Thus, treatment with alkyl halides may preferentially affect isozymes of cytochrome p450.

The potential for 1,2-dibromo-3-chloropropane (DBCP) to reduce male fertility by acting at a site in the genital tract beyond the testis was evaluated in male rats. Doses of 10, 20, or 40 mg/kg DBCP given sc once daily for 7 days caused a dose-dependent redn in the metab of glucose to carbon dioxide by epididymal sperm, as measured in vitro. Conversion of glucose to lactate was not reduced, indicating inhibition of energy metab at a step postglycolysis. The direct addn of DBCP to epididymal sperm being incubated in vitro also inhibited the metab of glucose to CO2. Thus, DBCP may cause a nearly immediate infertility via a direct effect on posttesticular sperm. A possible mechanism of the infertility is inhibition by DBCP of glucose metab in the ejaculated sperm.

Subcutaneous administration of the nematocide, 1,2-dibromo-3-chloropropane (DBCP), to adult, male, fischer 344 rats transiently depleted hepatic and caput (head) epididymal nonprotein sulfhydryl contents. NPS concentrations in the testis and kidney were not lowered by DBCP. Liver, kidney and testis all exhibited increases in tissue nonprotein sulfhydryl concentrations 48 hr after treatment; the effects were most prominent in the outer medullary section of the kidney 24 hr after treatment with 80 mg/kg of DBCP. The glutathione depleting agent diethyl maleate transiently lowered hepatic, renal and caput epididymal nonprotein sulfhydryl concentrationsin a dose and time dependent manner. Renal and caput epididymal nonprotein sulfhydryl contents were increased relative to control 24 hr after diethyl maleate treatment. Single sc injections of DBCP produced dose dependent lesions in the kidney, testis, caput epididymis and liver. Diethyl maleate treatment 90 min before DBCP treatment enhanced the nephrotoxic potency of DBCP as indicated by greater elevations of blood urea nitrogen and serum creatinine concentrations and by more severe renal tubular necrosis in diethyl maleate pretreated thanin vehicle controls, as determined 48 hr after DBCP exposure. Seminiferous tubular degeneration, as determined 48 hr post-DBCP treatment, was greater in rats pretreated with 600 mg/kg of diethyl maleate than in nonpretreated controls. When examined 16 days after DBCP treatment, however, the severity of testicular atrophy was virtually the same in rats pretreated with a lower dose of diethyl maleate (400 mg/kg) as in nonpretreated rats. These results indicate that DBCP is a depletor of hepatic and caput epididymal NPS in the acutely toxic dose range. Inasmuch as NPS concentrations were not lowered in two of the major target organs, kidney and testis, acute DBCP injury would not appear to be dependent on local glutathione depletion. However, the greater susceptibility of kidney and testis to DBCP injury after diethyl maleate pretreatment suggests an important role for nonprotein sulfhydryl, particularly those in the liver, in modulating DBCP toxicities.

Following intraperitoneal admin of 50 mg/kg of 1,2-dibromo-3-chloropropane (DBCP) to rats in propylene glycol, S,S'-(2-hydroxypropane-1,3-diyl)bismercapturic acid & S-(2,3-dihydroxypropyl)mercapturic acid were found as metabolites in urine. The metabolic pathway for DBCP incl oxidation & hydrolysis to a series of epoxide metabolites, and formation of male anti-fertility agents alpha-chlorohydrin & alpha-bromohydrin from epoxides. Subsequent oxidative metabolism of these latter two cmpd to oxalic acid presumably causes liver damage.

Rats treated orally with 1,2-dibromo-3-chloropropane (DBCP) excrete small amt of 2-bromoacrylic acid. Rabbit liver microsomal oxidases also yield 2-bromoacrylic acid from DBCP. The conversion involves initial enzymic sulfoxidation or hydroxylation at methyl chloride moiety (-CH2Cl) substituents and then facile nonenzymic reactions to liberate 2-haloacroleins which are further oxidized to the 2-haloacrylic acids. 2-Haloacroleins as potent mutagens and intermediary metabolites may contribute to the adverse toxicologic properties of DBCP.

1,2-Dibromo-3-chloropropane is absorbed via oral, inhalation, and dermal routes. It accumulates mainly in the kidney, liver, and adipose tissues. 1,2-Dibromo-3-chloropropane is intially converted to epoxy derivatives, which are further hydrolyzed and debrominated. Glutathione (GSH) conjugation of epoxide intermediates in the liver is believed to produce precursors to toxic intermediates. The metabolites are excreted mainly in the urine. (L125)

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice.

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.

CAN BE ABSORBED PERCUTANEOUSLY IN TOXIC AMT.

MALE WISTAR RATS WERE GIVEN ORALLY 20-400 MG/KG (14)C-LABELED 1,2-DIBROMO-3-CHLOROPROPANE. MAJOR SITES OF RADIOACTIVITY WERE FOUND IN THE LIVER & KIDNEY. IT IS SUGGESTED THAT THE MACROMOLECULAR BINDING IN VIVO IS CAUSED BY AN ACTIVATED METABOLIC INTERMEDIATE FORMED ON MICROSOME.

When a dose of 20 mg/kg 1,2-dibromo-3-chloropropane-3-(14)C was given orally ... /to/ male rats ... only traces (0.04%) of the (14)C were excreted in the expired air as unchanged 1,2-dibromo-3-chloropropane. Essentially all (98.8%) was absorbed from the gut and 90% of the activity was excreted in 3 days. During the first 24 hr, 49, 14, and 16.5% ... was excreted in the urine, feces, and expired air ... .

Until 1977, DBCP was used as a soil fumigant and nematocide on over 40 different crops in the United States. From 1977 to 1979, EPA suspended registration for all DBCP-containing products except for use on pineapples in Hawaii. In 1985, EPA issued an intent to cancel all registrations for DBCP, including use on pineapples. Subsequently, the use of existing stocks of DBCP was prohibited.

All uses except on pineapple plantations in Hawaii canceled in 1979; use on pineapples cancelled in 1985; See 29CFR1910.1044;

Farming (Pesticides) [Category: Industry]

Cancellation of all registrations of end use products except for the use on pineapples in Hawaii /as soil fumigant/ (3/31/81)

Intermediate in organic synthesis; LV (low in volatiles) commercial preparation for the flame retardant tris(2,3-dibromopropyl)phosphate

Unclassified nematocide used for soil fumigation of cucumbers, summer squash, cabbage, cauliflower, carrots, snap beans, okra, aster, shasta daisy, ornamental turf (lawns), bermuda grass, centipede grass, St Augustine grass, zoysia grass, ardisia, azalea, camellia, forsythia, gardenia, hibiscus, roses, and arborvitae. /Gro-Tone Nematode Granular/ /Former uses/

(1977) PROBABLY GREATER THAN 4.54X10+6 G

(1982) PROBABLY GREATER THAN 2.27X10+6 G

FUMAZONE 86E: 1,2-DIBROMO-3-CHLOROPROPANE AND RELATED HALOGENATED C3 HYDROCARBONS, 84.0%, INERT INGREDIENTS 16.0%, (PETROLEUM SOLVENT 9%). FUMAZONE 86: 1,2-DIBROMO-3-CHLOROPROPANE & RELATED HALOGENATED C3 ALIPHATICS 85.5%, PETROLEUM SOLVENT 14.5%.

1,2-DIBROMO-3-CHLOROPROPANE IS AVAIL IN USA AS TECHNICAL GRADE CONTAINING NOT LESS THAN 95% OF PURE CHEM, AS EMULSIFIABLE CONCENTRATES CONTAINING 70.7-87.8%, AS SOLN CONTAINING 47.2%, AS GRANULES CONTAINING 5.25-34%, & IN FERTILIZER MIXT CONTAINING 0.6-5%.

Gro-Tone Nematode Granular; granular, 17.3% Dibromo-3-chloropropane

Durham Nematocode EM 17.1, Nematocide Solution 17.1, soluble concn, 97% Dibromo-3-chloropropane

For more Formulations/Preparations (Complete) data for 1,2-DIBROMO-3-CHLOROPROPANE (7 total), please visit the HSDB record page.

Propane, 1,2-dibromo-3-chloro-: ACTIVE

MANY PERENNIAL PLANTS TOLERATE HIGH CONCN BUT OTHERS, EG TOBACCO, POTATO, ARE SENSITIVE AND LONG AERATION PERIOD PRIOR TO PLANTING MAY BE NECESSARY.

1,2-DIBROMO-3-CHLOROPROPANE IS ... EFFECTIVE AGAINST A WIDE RANGE OF NEMATODES, INCLUDING ROOT-KNOT NEMATODES, AT 10-125 KG/HA. SOIL TEMP AT 15 CM DEPTH SHOULD BE 21-27 °C FOR BEST RESULTS.

1,2-Dibromo-3-chloropropane was first produced commercially in the US in 1955.

All US usage of 1,2-dibromo-3-chloropropane was cancelled in 1979.

Manufacturers: Shell (formerly); Dow (formerly); Amvac.