1,3-Dichloropropene

1,3-Dichloropropene, sold under diverse trade names, is an organochlorine compound. It is colorless liquid with a sweet smell. It dissolves in water and evaporates easily. It is used mainly in farming as a pesticide, specifically as a preplant fumigant and nematicide. It is widely used in the US and other countries, but is in the process of being phased out in the European Union.[2]

Not to be confused with 1,3-dichloropropane.

1,3-Dichloropropene
Skeletal formula of the trans isomer
Skeletal formula of the cis isomer
Ball-and-stick model of the trans isomer
Ball-and-stick model of the cis isomer
Names
Preferred IUPAC name
1,3-Dichloroprop-1-ene
Other names
AQL Agrocelhone, DD92, 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, 1,3-dichloropropylene, 3-D, DCP, 3-Chloroallyl chloride
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.024
EC Number
  • 208-826-5
KEGG
MeSH 1,3-dichloro-1-propene
RTECS number
  • UC8310000
UNII
UN number 2047
Properties
C3H4Cl2
Molar mass 110.97 g/mol
Appearance Colorless to straw-colored liquid
Odor sweet, chloroform-like
Density 1.217 g/mL (cis); 1.224 g/mL (trans)
Melting point −84.5 °C (−120.1 °F; 188.7 K)
Boiling point 104 °C (219 °F; 377 K) (cis); 112 °C (trans)
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)
Hazards
GHS pictograms
GHS Signal word Danger
GHS hazard statements
 H226, H301, H304, H311, H315, H317, H319, H331, H332, H335, H400, H410
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P272, P273, P280, P301+310, P302+352, P303+361+353, P304+312, P304+340, P305+351+338, P311, P312, P321, P322, P330, P331
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point 28 °C (82 °F; 301 K)
> 500 °C (932 °F; 773 K)
Explosive limits 5.3% - 14.5% (80 °C)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 Ca TWA 1 ppm (5 mg/m3) [skin][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).
N verify (what is YN ?)
Infobox references

Production, chemical properties, biodegradation

It is a byproduct in the chlorination of propene to make allyl chloride.[3]

It is usually obtained as a mixture of the geometric isomers, called Z-1,3-dichloropropene, and E-1,3-dichloropropene. Although it was first applied in agriculture in the 1950s, at least two biodegradation pathways have evolved. One pathway degrades the chlorocarbon to acetaldehyde via chloroacrylic acid.[4]

Safety

The TLV-TWA for 1,3-dichloropropene (DCP) is 1 ppm.[5] It is a contact irritant. A wide range of complications have been reported.[6]

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. In the US, 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.[6]

Use

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

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

Contamination

The ATSDR has extensive contamination information available.[7]

Frequency of NPL Sites with 1,3-Dichloropropene Contamination
gollark: Or UK.
gollark: Alternative to plug sockets: embed wireless charging points at random places in the walls.
gollark: We have many fuses, though.
gollark: Don't think so? They are just regular switches.
gollark: Yes, the UK has such devices.

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0199". National Institute for Occupational Safety and Health (NIOSH).
  2. 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; is no longer in force, Official Journal of the European Union, 25 September 2007.
  3. Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche "Allyl Compounds" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005. Published online: 15 June 2000. doi:10.1002/14356007.a01_425
  4. Gerrit J. Poelarends, Christian P. Whitman "Evolution of enzymatic activity in the tautomerase superfamily: mechanistic and structural studies of the 1,3-dichloropropene catabolic enzymes" Bioorganic Chemistry 2004, Volume 32, Pages 376–392 doi:10.1016/j.bioorg.2004.05.006.
  5. Robert L. Metcalf "Insect Control" in Ullmann’s Encyclopedia of Industrial Chemistry" Wiley-VCH, Wienheim, 2002. doi:10.1002/14356007.a14_263

Further reading
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