1,3-Dichloropropene

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1,3-Dichloropropene
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 542-75-6 YesY
PubChem 24726
ChemSpider 23117
EC number 208-826-5
KEGG C06609
MeSH 1,3-dichloro-1-propene
ChEBI 18918
RTECS number UC8310000
SMILES Script error: No such module "collapsible list".
InChI Script error: No such module "collapsible list".
InChI key UOORRWUZONOOLO-OWOJBTEDBJ
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula C3H4Cl2
Molar mass 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)
Melting point

-84.5 °C

Boiling point

104 °C (cis); 112 °C (trans)

Solubility in water 2.18 g/L (cis) @ 25 °C; 2.32 g/L (trans) @ 25 °C
log P 1.82
Vapor pressure 34.4 mm Hg @ 25 °C (cis); 23.0 mm Hg @ 25 °C (trans)
style="background: #F8EABA; text-align: center;" colspan="2" | Hazards
EU Index 208-826-5
EU classification T,N
R-phrases 10-20/21-25-36/37/38-43-50/53
S-phrases (1/2-)-36/37-45-60-61
NFPA 704
3
2
0
Flash point 28 °C
Autoignition
temperature
> 500 °C
Explosive limits 5.3% - 14.5% (80 °C)
U.S. Permissible
exposure limit (PEL)
1
 YesY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 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.[1]

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]

A few workers who had skin contact with pesticides containing DCP developed blisters and an allergic reaction on their skin.[citation needed]

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.[3]

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.[2]

Use

1,3-Dichloropropene is used as a pesticide in the following crops: [4]

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 ATSDR has extensive contamination information available.[3]

File:Frequency of npl sites with DCP contam.png
Frequency of NPL Sites with 1,3-Dichloropropene Contamination

References

  1. 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.
  2. [1]
  3. [2]

Further reading

de:1,3-Dichlorpropen et:1,3-dikloropropeen fr:1,3-dichloropropène nl:1,3-dichloorpropeen ja:1,3-ジクロロプロペン