View source for 1,3-Dichloropropene

{{chembox
| verifiedrevid = 322201811
| ImageFileL1 = Trans-1,3-Dichloropropene.svg
| ImageSizeL1 = 130px
| ImageNameL1 = Skeletal formula of the trans isomer
| ImageFileR1 = Cis-1,3-Dichloropropene.svg
| ImageSizeR1 = 120px
| ImageNameR1 = Skeletal formula of the cis isomer
| ImageFileL2 = Trans-1,3-Dichloropropene-3D-balls.png
| ImageSizeL2 = 120px
| ImageNameL2 = Ball-and-stick model of the trans isomer
| ImageFileR2 = Cis-1,3-Dichloropropene-3D-balls.png
| ImageSizeR2 = 120px
| ImageNameR2 = Ball-and-stick model of the cis isomer
| IUPACName = 1,3-dichloroprop-1-ene
| SystematicName = 1-Propene, 1,3-dichloro-, (1E)-
| OtherNames = 1,3-D, Dorlone, Nematox, Telone, Nemex, cis-Dichloropropene, Di-Trapex CP, Vorlex 201, dichloro-1,3-propene, 1,3-dichloro-1-propene, 1,3-dichloro-2-propene, alpha-chloroallylchloride, chloroallylchloride, gamma-chloroallylchloride, chloroallyl chloride, chloroorpropenyl chloride, 3-dichloropropylene, 3-D, DCP
| Section1 = {{Chembox Identifiers
| Abbreviations =
| ChemSpiderID = 23117
| InChIKey = UOORRWUZONOOLO-OWOJBTEDBJ
| CASNo_Ref = {{cascite}}
| CASNo = 542-75-6
| EINECS = 208-826-5
| EINECSCASNO =
| PubChem = 24726
| SMILES = Cl[C@H]=CCCl
| InChI = 1/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+
| RTECS = UC8310000
| MeSHName = 1,3-dichloro-1-propene
| ChEBI = 18918
| KEGG = C06609
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| ATCCode_suffix =
| ATC_Supplemental =}}
| Section2 = {{Chembox Properties
| Formula = C<sub>3</sub>H<sub>4</sub>Cl<sub>2</sub>
| MolarMass = 110.97 g/mol
| Appearance = Colorless to straw-colored liquid, sweet chloroform-like odor
| Density = 1.217 g/mL (cis); 1.224 g/mL (trans)
| MeltingPt = -84.5 °C
| Melting_notes =
| BoilingPt = 104 °C (cis); 112 °C (trans)
| Boiling_notes =
| Solubility = 2.18 g/L (cis) @ 25 °C; 2.32 g/L (trans) @ 25 °C
| SolubleOther =
| Solvent =
| LogP = 1.82
| VaporPressure = 34.4 mm Hg @ 25 °C (cis); 23.0 mm Hg @ 25 °C (trans)
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| Section3 = {{Chembox Structure
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| Section4 = {{Chembox Thermochemistry
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| Section5 = {{Chembox Pharmacology
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| Section6 = {{Chembox Explosive
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| Section7 = {{Chembox Hazards
| EUClass = T,N
| EUIndex = 208-826-5
| MainHazards =
| NFPA-H = 2
| NFPA-F = 3
| NFPA-R = 0
| NFPA-O =
| RPhrases = 10-20/21-25-36/37/38-43-50/53
| SPhrases = (1/2-)-36/37-45-60-61
| RSPhrases =
| FlashPt = 28 °C
| Autoignition = > 500 °C
| ExploLimits = 5.3% - 14.5% (80 °C)
| PEL = 1}}
| Section8 = {{Chembox Related
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}}

'''1,3-Dichloropropene''', also known as '''Telone''' or simply '''1,3-D''',  is a colorless liquid with a sweet smell. It exists as a mixture of the [[Cis-trans isomerism|geometric isomers]] cis-1,3-dichloropropene and trans-1,3-dichloropropene. It dissolves in water and evaporates easily. It is used mainly in farming as a pesticide, specifically  as a preplant [[fumigant]] and [[nematicide]]. It widely used in the US and other countries, but in the process of being phased out in the [[European Union]].<ref>[http://eur-lex.europa.eu/LexUriServ/site/en/oj/2007/l_249/l_24920070925en00110013.pdf COMMISSION DECISION of 20 September 2007 concerning the non-inclusion of 1,3-dichloropropene in Annex I to Council Directive 91/414/EEC and the withdrawal of authorisations for plant protection products containing that substance], ''Official Journal of the European Union'', 25 September 2007.</ref>

==Effects==
1,3-Dichloropropene (DCP) causes irritation at the point of contact. Inhalation can cause nausea, vomiting, irritation of the skin, eyes, and throat; breathing difficulties, headache, and fatigue. These effects generally occur at exposure levels that are much higher than the background levels found in air or water. Rats and mice that inhaled DCP repeatedly for about 2 weeks had damage to the lining of the nose, and mice had damage to the lung.

A man who accidentally ingested DCP died with severe damage to his stomach and surrounding organs, but little else is known about the effects of ingesting these substances in humans. Animal studies have reported damage to the stomach lining, lung congestion, difficulty walking, and effects on the liver and kidneys from ingesting high levels of DCP.{{Citation needed|date=September 2007}}

A few workers who had skin contact with pesticides containing DCP developed blisters and an allergic reaction on their skin.{{Citation needed|date=September 2007}}

It is not known whether DCP can cause birth defects in humans. Pregnant rats that inhaled 1,3-dichloropropene gave birth to fewer pups or pups with lower body weight. This occurred at exposures high enough to be toxic to the mothers.[http://www.atsdr.cdc.gov/tfacts40.html]

DCP is testable via blood and urine tests, although it is only detectable in the body for 1-2 after exposure.  Exposure level estimates are possible with a blood sample.

==Carcinogenicity==
Evidence for the carcinogenicity of 1,3-dichloropropene in humans is inadequate, but results from several cancer bioassays provide adequate evidence of carcinogenicity in animals. The Department of Health and Human Services (DHHS) has determined that 1,3-dichloropropene may reasonably be anticipated to be a carcinogen. The International Agency for Research on Cancer (IARC) has determined that 1,3-dichloropropene is possibly carcinogenic to humans. The EPA has classified 1,3-dichloropropene as a probable human carcinogen.<ref>[http://www.atsdr.cdc.gov/tfacts40.html]</ref>

==Use==
1,3-Dichloropropene is used as a pesticide in the following crops: [http://ca.water.usgs.gov/pnsp/crop/]

{| border="1"
|+ 1,3-Dichloropropene Use in Crops
! Crop !! Pounds (lb) !! Primary Pesticide?
|-
| Tobacco
| 12,114,887 || Yes
|-
| Potatoes
| 12,044,736 || Yes
|-
| Sugar Beets
| 5,799,613 || Yes
|-
| Cotton
| 3,735,543 || Yes
|-
| Peanuts
| 3,463,003 || Yes
|-
| Sweet Potatoes
| 1,210,872 || Yes
|-
| Onions
| 674,183 || Yes
|-
| Carrots
| 531,752 || Yes
|-
| Watermelons
| 133,801 || No
|-
| Cantaloups
| 121,395 || No
|-
| Cucumbers
| 76,735 || No
|-
| Strawberries
| 71,753 || No
|-
| Sweet Peppers
| 28,247 || No
|-
| Melons
| 12,471 || No
|-
| Blueberries
| 3,090 || No
|-
| Asparagus
| 1,105 || No
|}

==Contamination==
The [[Agency for Toxic Substances and Disease Registry|ATSDR]] has extensive contamination information available.<ref>[http://www.atsdr.cdc.gov/toxprofiles/tp40.pdf]</ref>

[[Image:Frequency of npl sites with DCP contam.png|frame|none|Frequency of [[National Priorities List|NPL Sites]] with 1,3-Dichloropropene Contamination]]

==References==
<references />
*[http://www.atsdr.cdc.gov/tfacts40.html#bookmark05 ATSDR ToxFAQs: Dichloropropenes]
*[http://www.atsdr.cdc.gov/tfacts40.html#bookmark06 ATSDR ToxFAQs: Dichloropropenes]
*[http://ca.water.usgs.gov/pnsp/crop/ USGS Pesticide National Synthesis Project - Crop & Compound]

==Further reading==
*[http://www.atsdr.cdc.gov/toxprofiles/tp40.pdf ATSDR Toxicological Profile (9.2 MB)]

{{Use dmy dates|date=August 2010}}

{{DEFAULTSORT:Dichloropropene, 1,3-}}
[[Category:Pesticides]]
[[Category:Alkenes]]
[[Category:Organochlorides]]
[[Category:IARC Group 2B carcinogens]]

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[[fr:1,3-dichloropropène]]
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[[ja:1,3-ジクロロプロペン]]
[[Category:2Fix]]