1,3-Dichloropropene

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,[1][2] 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
CAS Number	542-75-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18918 ;
ChEMBL	ChEMBL155926 ;
ChemSpider	23117 ;
ECHA InfoCard	100.008.024
EC Number	208-826-5;
KEGG	C18627 ;
MeSH	1,3-dichloro-1-propene
PubChem CID	24726;
RTECS number	UC8310000;
UNII	9H780918D0 ;
UN number	2047
CompTox Dashboard (EPA)	DTXSID1022057 ;
	InChI InChI=1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+ Key: UOORRWUZONOOLO-OWOJBTEDSA-N ; InChI=1/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+ Key: UOORRWUZONOOLO-OWOJBTEDBJ;
	SMILES Cl[C@H]=CCCl;
Properties
Chemical formula	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)
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)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H301, H302, H305, H311, H315, H317, H319, H331, H332, H335, H410
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P272, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P331, P332+P313, P333+P313, P337+P313, P361, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)	2 3 0
Flash point	28 °C (82 °F; 301 K)
Autoignition; temperature	> 500 °C (932 °F; 773 K)
Explosive limits	5.3% - 14.5% (80 °C)
	NIOSH (US health exposure limits):
PEL (Permissible)	none[3]
REL (Recommended)	Ca TWA 1 ppm (5 mg/m3) [skin][3]
IDLH (Immediate danger)	Ca [N.D.][3]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.[4]

Production, chemical properties, biodegradation

It is a byproduct in the chlorination of propene to make allyl chloride.[5]

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.[6]

Safety

The TLV-TWA for 1,3-dichloropropene (DCP) is 1 ppm.[7] It is a contact irritant. A wide range of complications have been reported.[8]

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.[8]

Use

1,3-Dichloropropene is used as a pesticide in the following crops:[9]

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.[10]

Frequency of NPL Sites with 1,3-Dichloropropene Contamination

Market history

Under the brand name Telone, 1,3-D was one of Dow AgroSciences's products until the merger into DowDuPont. Then it was spun off with Corteva, and as of 2020 has been licensed to Telos Ag Solutions and is no longer a Corteva product.[1][2]

References

Martin, Frank N. (2003). "Development of Alternative Strategies for Management of Soilborne Pathogens Currently Controlled with Methyl Bromide". Annual Review of Phytopathology. Annual Reviews. 41 (1): 325–350. doi:10.1146/annurev.phyto.41.052002.095514. ISSN 0066-4286. PMID 14527332.
"Telone soil fumigant to be distributed by Telos Ag Solutions". Vegetable Growers News. 17 November 2020. Retrieved 6 July 2021.
NIOSH Pocket Guide to Chemical Hazards. "#0199". National Institute for Occupational Safety and Health (NIOSH).
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.
Krähling, Ludger; Krey, Jürgen; Jakobson, Gerald; Grolig, Johann; Miksche, Leopold (15 June 2000), "Allyl Compounds", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, doi:10.1002/14356007.a01_425, retrieved 18 March 2022
Poelarends, Gerrit J.; Whitman, Christian P. (1 October 2004). "Evolution of enzymatic activity in the tautomerase superfamily: mechanistic and structural studies of the 1,3-dichloropropene catabolic enzymes". Bioorganic Chemistry. Mechanistic Enzymology. 32 (5): 376–392. doi:10.1016/j.bioorg.2004.05.006. ISSN 0045-2068.
Robert L. Metcalf "Insect Control" in Ullmann’s Encyclopedia of Industrial Chemistry" Wiley-VCH, Wienheim, 2002. doi:10.1002/14356007.a14_263
"ToxFAQs™ - Letter A | Toxic Substance Portal | ATSDR".
"National Totals of Pesticide Use (pounds applied and acres treated) by Crop and Compound". USGS. Archived from the original on 10 April 2007.
"TOXICOLOGICAL PROFILE FOR DICHLOROPROPENES" (PDF). Agency for Toxic Substances and Disease Registry. September 2008.