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Revision as of 16:09, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464323412 of page 1,2-Dibromo-3-chloropropane for the Chem/Drugbox validation project (updated: '').		Latest revision as of 00:42, 22 November 2024 edit Mfernflower (talk | contribs)Extended confirmed users7,828 edits →UsesTags: Mobile edit Mobile web edit Advanced mobile edit
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			{{Redirect|DBCP|the database connection pool implementation|Apache Commons}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 443642899
			| verifiedrevid = 477203298
	| ImageFile = 1,2-Dibromo-3-chloropropane.svg
			| ImageFile = 1,2-Dibrom-3-chlorpropan Grundstruktur V1-Seite001.svg
	| ImageFile1 = 1,2-Dibromo-3-chloropropane3d.png
	| IUPACName = 1,2-Dibromo-3-chloropropane		| ImageFile1 = 1,2-Dibromo-3-chloropropane3d.png
			| PIN = 1,2-Dibromo-3-chloropropane
	| OtherNames =
			| OtherNames = Dibromochloropropane
	| Section1 = {{Chembox Identifiers
			|Section1={{Chembox Identifiers
	| Abbreviations = DBCP
			| Abbreviations = DBCP
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 7008		| ChemSpiderID = 7008
	| InChIKey = WBEJYOJJBDISQU-UHFFFAOYAN		| InChIKey = WBEJYOJJBDISQU-UHFFFAOYAN
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 96-12-8		| CASNo = 96-12-8
	| EINECS =		| EINECS =
	| PubChem =		| PubChem = 7280
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 96K0FD4803		| UNII = 96K0FD4803
	| SMILES = BrC(CBr)CCl		| SMILES = BrC(CBr)CCl
	| InChI = 1/C3H5Br2Cl/c4-1-3(5)2-6/h3H,1-2H2		| InChI = 1/C3H5Br2Cl/c4-1-3(5)2-6/h3H,1-2H2
	| RTECS =		| RTECS =
	| MeSHName =		| MeSHName =
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI =		| ChEBI =
	| KEGG_Ref = {{keggcite|correct|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C14336		| KEGG = C14336
			}}
	| ATCCode =
			|Section2={{Chembox Properties
	}}
	| Section2 = {{Chembox Properties
	| C=3 | H=5 | Br=2 | Cl=1		| C=3 | H=5 | Br=2 | Cl=1
	| MolarMass = 236.33 g/mol		| MolarMass = 236.33 g/mol
	| Appearance =		| Appearance = Dense colorless liquid
	| Density =		| Odor = pungent
	| MeltingPt =		| Density = 2.05 g/mL
	| BoilingPt =		| MeltingPtC = 6.1
	| Solubility =		| BoilingPtC = 195.5
			| Solubility = 0.1%<ref name=PGCH/>
	| SolubleOther =
	| Solvent =		| SolubleOther =
	| pKa =		| Solvent =
	| pKb =		| pKa =
	| IsoelectricPt =		| pKb =
			| IsoelectricPt =
	| SpecRotation =		| SpecRotation =
	| RefractIndex =		| RefractIndex =
	| Viscosity =		| Viscosity =
			| VaporPressure = 0.8 mmHg (20 °C)<ref name=PGCH/>
	}}		}}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| Dipole =		| CrystalStruct =
	| CrystalStruct =		| Coordination =
	| Coordination =		| MolShape =
	| MolShape =		| Dipole =
	| Dipole =
	}}		}}
	| Section4 = {{Chembox Thermochemistry		|Section4={{Chembox Thermochemistry
	| DeltaHf =		| DeltaHf =
	| DeltaHc =		| DeltaHc =
	| Entropy =		| Entropy =
	| HeatCapacity =		| HeatCapacity =
	}}		}}
	| Section5 = {{Chembox Pharmacology		|Section5={{Chembox Pharmacology
	| Bioavail =		| Bioavail =
	| Metabolism =		| Metabolism =
	| HalfLife =		| HalfLife =
	| Excretion =		| Excretion =
	| PregCat =		| Pregnancy_category =
	| AdminRoutes =		| AdminRoutes =
	}}		}}
	| Section6 = {{Chembox Explosive		|Section6={{Chembox Explosive
	| ShockSens =		| ShockSens =
	| FrictionSens =		| FrictionSens =
	| ExplosiveV =		| DetonationV =
	| REFactor =		| REFactor =
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
			| MainHazards = carcinogen<ref name=PGCH/>
	| EUClass =
	| MainHazards =		| NFPA-H = 2
	| NFPA-H =		| NFPA-F = 1
	| NFPA-F =		| NFPA-R = 1
	| NFPA-R =		| NFPA-S =
			| GHSPictograms = {{GHS06}}{{GHS08}}<ref name="sigma"/>
	| NFPA-O =
			| HPhrases = {{H-phrases|301|340|350|360|373|412}}<ref name="sigma">{{Sigma-Aldrich|Aldrich|id=676713|name=1,2-Dibromo-3-chloropropane|accessdate=2013-07-20}}</ref>
	| GHSPictograms = {{GHSp|GHS06}}{{GHSp|GHS08}}<ref name = "sigma" />
	| HPhrases = {{GHSp|H301}} - {{GHSp|H340}} - {{GHSp|H350}} - {{GHSp|H360}} - {{GHSp|H373}} - {{GHSp|H412}}<ref name="sigma">{{SigmaLink		| PPhrases = {{P-phrases|201|273|301+310|308+313}}<ref name="sigma"/>
	| Productgroup = Aldrich		| FlashPtC = 76.7
			| AutoignitionPtC =
	| Productcode = 676713
			| ExploLimits =
	| Accessdate = may 20, 2011
			| PEL = TWA 0.001 ppm <ref name=PGCH>{{PGCH|0184}}</ref>
	}}</ref>
			| IDLH = Ca, N.D.<ref name=PGCH/>
	| PPhrases = {{GHSp|P201}} - {{GHSp|P273}} - {{GHSp|P301+P310}} - {{GHSp|P308+P313}}<ref name="sigma" />
	| RSPhrases =		| REL = Ca<ref name=PGCH/>
	| FlashPt =
	| Autoignition =
	| ExploLimits =
	| PEL =
	}}		}}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| OtherAnions =		| OtherAnions =
	| OtherCations =		| OtherCations =
	| OtherFunctn =		| OtherFunction =
			| OtherFunction_label =
	| Function =
	| OtherCpds =		| OtherCompounds =
	}}		}}
	}}		}}
			'''1,2-Dibromo-3-chloropropane''' ('''dibromochloropropane'''), better known as '''DBCP''', is the ] with the formula BrCH(CH{{sub|2}}Br)(CH{{sub|2}}Cl). It is a dense colorless liquid although commercial samples often appear amber or even brown. It is the active ingredient in the ] '''Nemagon''', also known as '''Fumazone'''.
			It is a soil ] formerly used in American ]. 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 ] (EPA).<ref name="EPA"> {{Webarchive|url=https://web.archive.org/web/20160322000112/https://www3.epa.gov/ttn/atw/hlthef/dibromo-.html |date=2016-03-22 }}. - ]. - EPA.gov.</ref> The continuing presence of the chemical as a ] in ] remains a problem for many communities for years after end of use.
			== Stereoisomerism ==
			{| class="wikitable" style="text-align:center"
			|- class="hintergrundfarbe6"
			! colspan="2"| 1,2-Dibromo-3-chloropropane<br /><small>(2 stereoisomers)</small>
			|-
			| ]<br /><small>(''R'')-configuration</small>
			| ]<br /><small>(''S'')-configuration</small>
			|}
			== Uses ==
			* Until 1977, DBCP was used as a soil ] and ] on over 40 different crops in the United States. It fights pests that attack the roots of fruit trees and boosts the weight of harvests by 20 percent.<ref name=SpanoJ-LAT-2007-11-15>Spano, John. - "Dole Must Pay $2.5 Million in Punitive Damages". - '']''. - November 15, 2007.</ref> From 1977 to 1979, EPA suspended registration for all DBCP-containing products except for use on pineapples in ]. In 1985, EPA issued an intent to cancel all registrations for DBCP, including use on ]s. Subsequently, the use of existing stocks of DBCP was prohibited.
			* DBCP is also sometimes used as a starting material in ].
			== Sources and potential exposure ==
			Human exposure to DBCP could result from the ingestion of contaminated ] 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.
			== Examples of persistence ==
			DBCP residues have persisted in ] and groundwater long after applications have ceased. For example, in agricultural areas around ] in the ] 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 ] had to be shut down at that time.<ref>"Environmental Screening Analysis, Tully Road Properties, Turlock, California". - Earth Metrics Incorporated. - Report 7826, San Mateo, California. - March, 1989</ref>
			== Lawsuits ==
			Workers at the ] plant producing DBCP were made ] 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 ] 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 ], which was using the chemical on its ] ]s in ], 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 not permit awarding damages in the face of clear scientific evidence of the absence of causation," or, as in this case, "with proof that are not at fault."<ref> {{Webarchive|url=https://web.archive.org/web/20151208062051/http://www.rttnews.com/1104848/u-s-court-refuses-to-enforce-nicaragua-judgment-against-dole-food-update.aspx|date=2015-12-08}}. - ''''. - October 26, 2009</ref> 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.<ref name=SpanoJ-LAT-2007-11-06>Spano, John. - {{Webarchive|url=https://web.archive.org/web/20190821110708/http://www.latimes.com/news/printedition/california/la-me-dole6nov06,1,2105565.story |date=2019-08-21 }}. - '']''. - November 6, 2007.</ref> 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".<ref> . - '']''. - July 15, 2010</ref> 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.<ref name=HallmanB-TAL-2009-4-27>Hallman, Ben. - {{Webarchive|url=https://web.archive.org/web/20121108154951/http://www.law.com/jsp/article.jsp?id=1202430211082&rss=newswire |date=2012-11-08 }}. - '']''. - April 27, 2009.</ref> The ruling casts doubt on US$2 ] in judgments in similar lawsuits.<ref name=KeatingG-Forbes-2009-4-24>Keating, Gina. - {{dead link|date=January 2022|bot=medic}}{{cbignore|bot=medic}}. - '']''. - April 24, 2009.</ref>
			Workers in ], using the ], and claiming sterility, crimes against humanity, and ], sued (in ''Abagninin v. AMVAC Chemical Corp.'' ), these manufacturers of DBCP: ], ], ], as well as ], who used it on overseas crops, but never used it in Côte d'Ivoire. The ] ruled against the workers in September 2008, stating that the plaintiffs did not show that the defendants had "specific intent" to intend harm against the workers and the citizens of the country. To be found guilty of genocide the defendant must have knowingly set out to commit the offense.<ref name=USCofA9thC-AvACC> {{Webarchive|url=https://web.archive.org/web/20081106170714/http://www.ca9.uscourts.gov/ca9/newopinions.nsf/40AB16BDDF8C33D9882574CD007E8677/$file/0756326.pdf?openelement |date=2008-11-06 }}. - ]. - September 24, 2008. - (Adobe Acrobat *.PDF document).</ref><ref name=WilliamsCJ-LAT-2008-09-24>Williams, Carol J. - "Appeals Court Rules Against Ivory Coast Farm Workers". - '']''. - September 24, 2008.</ref>
			== Safety ==
			DBCP causes a dramatic decrease in male fertility, ranging from ] (low sperm count) to ] (lack of sperm).<ref>{{Cite journal|title = DDT exposure, work in agriculture, and time to pregnancy among farmworkers in California|journal = Journal of Occupational and Environmental Medicine|date = Dec 2008|issn = 1536-5948|pmc = 2684791|pmid = 19092487|pages = 1335–1342|volume = 50|issue = 12|doi = 10.1097/JOM.0b013e31818f684d|first = Kim G.|last = Harley|first2 = Amy R.|last2 = Marks|first3 = Asa|last3 = Bradman|first4 = Dana B.|last4 = Barr|first5 = Brenda|last5 = Eskenazi}}</ref>
			== References ==
			{{Reflist}}
			== External links ==
			* {{Webarchive|url=https://web.archive.org/web/20080525090432/http://www.commondreams.org/archive/2007/05/27/1487/ |date=2008-05-25 }}
			*
			*
			*
			{{DEFAULTSORT:Dibromo-3-Chloropropane, 1, 2-}}
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			]
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			]
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			]
			]