Names | |
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Preferred IUPAC name 1,2-Dibromo-3-chloropropane | |
Other names Dibromochloropropane | |
Identifiers | |
3D model (JSmol) | |
Abbreviations | DBCP |
ChemSpider | |
ECHA InfoCard | 100.002.255 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C3H5Br2Cl | |
Molar mass | 236.33 g/mol |
Appearance | Dense colorless liquid |
Odor | pungent odor at high concentrations |
Density | 2.05 g/mL |
Melting point | 6.1 °C (43.0 °F; 279.2 K) |
Boiling point | 195.5 °C (383.9 °F; 468.6 K) |
0.1% [1] | |
Vapor pressure | 0.8 mmHg (20 °C) [1] |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | carcinogen [1] |
GHS labelling: | |
[2] | |
H301, H340, H350, H360, H373, H412 [2] | |
P201, P273, P301+P310, P308+P313 [2] | |
NFPA 704 (fire diamond) | |
Flash point | 76.7 °C (170.1 °F; 349.8 K) |
NIOSH (US health exposure limits): | |
PEL (Permissible) | TWA 0.001 ppm [1] |
REL (Recommended) | Ca [1] |
IDLH (Immediate danger) | Ca, N.D. [1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
1,2-Dibromo-3-chloropropane (dibromochloropropane), better known as DBCP, is the organic compound with the formula BrCH(CH2Br)(CH2Cl). It is a dense colorless liquid although commercial samples often appear amber or even brown. It is the active ingredient in the nematicide Nemagon, also known as Fumazone.
It is a soil fumigant formerly used in American agriculture. In mammals, it causes male sterility at high levels of exposure. After discovery of its deleterious health effects on humans, the compound was banned from use in 1979 by the United States Environmental Protection Agency (EPA). [3] The continuing presence of the chemical as a contaminant in ground water remains a problem for many communities for years after end of use.
1,2-Dibromo-3-chloropropane (2 stereoisomers) | |
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(R)-configuration | (S)-configuration |
Human exposure to DBCP could result from the ingestion of contaminated drinking water and food. Exposure could also result from inhalation and/or skin contact with a product containing DBCP.
In the past, release of DBCP to the environment occurred primarily from its fumigant and nematocide uses; because of the cancellation of all DBCP uses, environmental exposure is expected to decline with time.
DBCP residues have persisted in contaminated soil and groundwater long after applications have ceased. For example, in agricultural areas around Turlock in the Central Valley of California, DBCP was applied to crops in the 1970s. As late as 1989, DBCP persistence was reported in groundwater that was previously used for beneficial purposes, and numerous nearby wells had to be shut down at that time. [5]
Workers at the Dow Chemical plant producing DBCP were made sterile by exposure to DBCP. These male reproductive effects were consistent with animal experiments showing that DBCP sterilizes rabbits. One contract worker at the production plant successfully sued the company. Most workers remained with the company and in a company sponsored medical program until the facility was sold in 1987. At that time, some of the workers did file suit against the company. However, the suit was denied due to statute of limitations issues.
Most uses of the chemical in the United States were banned in 1977. Amid growing concerns over DBCP's effects on male workers, Dow ceased production and reclaimed DBCP that had been shipped to its users.
However, despite warnings from Dow about its health effects, the Dole Food Company, which was using the chemical on its banana plantations in Latin America, threatened to sue Dow if it stopped DBCP shipments. Dow then shipped half a million gallons of DBCP to Dole, much of it reclaimed from other users. Plantation workers who became sterile or were stricken with other maladies subsequently sued Dow and Dole in Nicaraguan courts, alleging that their ailments were caused by DBCP exposure. Under a special law that was passed specifically for DBCP litigation, the Nicaraguan courts ruled in favor of the plaintiffs and awarded them over US$600 million in damages. When plaintiff lawyers tried to enforce one of those judgments in the United States, the U.S. District Court in Florida held that "the credible and unrefuted medical testimony in this case is that it is factually impossible for what is represented in the Judgment to have occurred," and that due process "do[es] not permit awarding damages in the face of clear scientific evidence of the absence of causation," or, as in this case, "with proof that [the defendants] are not at fault." [6] A group of workers then filed lawsuits in the United States, and on November 5, 2007, a Los Angeles jury awarded them US$3.2 million. [7] On July 15, 2010, that judgment was thrown out after the Court presiding over the case found that the claims were part of "a massive fraud perpetrated on the court". [8] On April 23, 2009, a Los Angeles judge also threw out two similar cases against Dole and Dow Chemical due to fraud and extortion by lawyers in Nicaragua recruiting fraudulent plaintiffs to make claims against the company. [9] The ruling casts doubt on US$2 billion in judgments in similar lawsuits. [10]
Workers in Côte d'Ivoire, using the Alien Tort Claims Act, and claiming sterility, crimes against humanity, and genocide, sued (in Abagninin v. AMVAC Chemical Corp. [No. 07-56326]), these manufacturers of DBCP: Amvac Chemical, Dow Chemical, Shell Oil Company, as well as Dole Food Company, who used it on overseas crops, but never used it in Côte d'Ivoire. The United States Court of Appeals for the Ninth Circuit ruled against the workers in September 2008, stating that the plaintiffs did not show that the defendants had "specific intent" to intend harm against the workers and the citizens of the country. To be found guilty of genocide the defendant must have knowingly set out to commit the offense. [11] [12]
DBCP causes a dramatic decrease in male fertility, ranging from oligospermia (low sperm count) to azoospermia (lack of sperm). [13]
Bromomethane, commonly known as methyl bromide, is an organobromine compound with formula CH3Br. This colorless, odorless, nonflammable gas is produced both industrially and biologically. It has a tetrahedral shape and it is a recognized ozone-depleting chemical. It was used extensively as a pesticide until being phased out by most countries in the early 2000s.
1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an organobromine compound with the chemical formula C
2H
4Br
2. Although trace amounts occur naturally in the ocean, where it is probably formed by algae and kelp, it is mainly synthetic. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm, and is a widely used and sometimes-controversial fumigant. The combustion of 1,2-dibromoethane produces hydrogen bromide gas that is significantly corrosive.
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Chlordecone, better known in the United States under the brand name Kepone, is an organochlorine compound and a colourless solid. It is an obsolete insecticide, now prohibited in the western world, but only after many thousands of tonnes had been produced and used. Chlordecone is a known persistent organic pollutant (POP) that was banned globally by the Stockholm Convention on Persistent Organic Pollutants in 2009.
In organic chemistry, chlorpyrifos (CPS), also known as chlorpyrifos ethyl, is an organophosphate pesticide that has been used on crops, animals, and buildings, and in other settings, to kill several pests, including insects and worms. It acts on the nervous systems of insects by inhibiting the acetylcholinesterase enzyme. Chlorpyrifos was patented in 1966 by Dow Chemical Company.
Sulfuryl fluoride (also spelled sulphuryl fluoride) is an inorganic compound with the formula SO2F2. It is an easily condensed gas and has properties more similar to sulfur hexafluoride than sulfuryl chloride, being resistant to hydrolysis even up to 150 °C. It is neurotoxic and a potent greenhouse gas, but is widely used as a fumigant insecticide to control termites.
Chloropicrin, also known as PS and nitrochloroform, is a chemical compound currently used as a broad-spectrum antimicrobial, fungicide, herbicide, insecticide, and nematicide. It was used as a poison gas in World War I. Its chemical structural formula is Cl3C−NO2.
Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted by rice plantations in small amounts. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups.
Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.
Organobromine chemistry is the study of the synthesis and properties of organobromine compounds, also called organobromides, which are organic compounds that contain carbon bonded to bromine. The most pervasive is the naturally produced bromomethane.
Sentinel Event Notification System for Occupational Risks (SENSOR)-Pesticides is a U.S. state-based surveillance program that monitors pesticide-related illness and injury. It is administered by the National Institute for Occupational Safety and Health (NIOSH), twelve state health agencies participate. NIOSH provides technical support to all participating states. It also provides funding to some states, in conjunction with the US Environmental Protection Agency.
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Naled (Dibrom) is an organophosphate insecticide. Its chemical name is dimethyl 1,2-dibromo-2,2-dichloroethylphosphate.
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