1,3-Dichloropropene

Not to be confused with 1,3-dichloropropane.

1,3-Dichloropropene, sold under diverse trade names, is an organochlorine compound with the formula C₃H₄Cl₂. It is a colorless liquid with a sweet smell. It is feebly soluble in water and evaporates easily. It is used mainly in farming as a pesticide, specifically as a preplant fumigant and nematicide. It acts non-specifically and is in IRAC class 8A. It is widely used in the US and other countries, but is banned in 34 countries (including the European Union).^[4]

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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18918 N
ChEMBL	ChEMBL155926 Y
ChemSpider	23117 Y
ECHA InfoCard	100.008.024
EC Number	208-826-5
KEGG	C18627 Y
MeSH	1,3-dichloro-1-propene
PubChem CID	24726
RTECS number	UC8310000
UNII	9H780918D0 Y
UN number	2047
CompTox Dashboard (EPA)	DTXSID1022057
InChI InChI=1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+ Y Key: UOORRWUZONOOLO-OWOJBTEDSA-N Y 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). N verify (what is YN ?) Infobox references

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. In California, the Office of Environmental Health Hazard Assessment has determined that 1,3-dichloropropene is a carcinogen, and in 2022 established a No Significant Risk Level (NSRL) of 3.7 micrograms/day.^[9] 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:^[10]

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.^[11]

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^[update] has been licensed to Telos Ag Solutions and is no longer a Corteva product.^[1][2]

References

1. Martin, Frank N. (2003). "Development of Alternative Strategies for Management of Soilborne Pathogens Currently Controlled with Methyl Bromide". Annual Review of Phytopathology. 41 (1). Annual Reviews: 325–350. doi:10.1146/annurev.phyto.41.052002.095514. ISSN 0066-4286. PMID 14527332.
2. "Telone soil fumigant to be distributed by Telos Ag Solutions". Vegetable Growers News. 17 November 2020. Retrieved 6 July 2021.
3. NIOSH Pocket Guide to Chemical Hazards. "#0199". National Institute for Occupational Safety and Health (NIOSH).
4. COMMISSION DECISION of 13 May 2022 concerning the non-approval of the active substance 1,3-dichloropropene, Official Journal of the European Union, 13 May 2022.
5. 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, ISBN 3527306730, retrieved 18 March 2022
6. 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. PMID 15381403.
7. Robert L. Metcalf "Insect Control" in Ullmann's Encyclopedia of Industrial Chemistry" Wiley-VCH, Wienheim, 2002. doi:10.1002/14356007.a14_263
8. "ToxFAQs – Letter A | Toxic Substance Portal | ATSDR".
9. "Proposition 65: No Significant Risk Level for 1,3-Dichloropropene (1,3-D)". oehha.ca.gov. 21 June 2022. Retrieved 26 October 2022.
10. "National Totals of Pesticide Use (pounds applied and acres treated) by Crop and Compound". United States Geological Survey. Archived from the original on 10 April 2007.
11. "TOXICOLOGICAL PROFILE FOR DICHLOROPROPENES" (PDF). Agency for Toxic Substances and Disease Registry. September 2008.

• ATSDR ToxFAQs: Dichloropropenes
• USGS Pesticide National Synthesis Project – Crop & Compound

Further reading

• ATSDR Toxicological Profile (9.2 MB)
• CDC – NIOSH Pocket Guide to Chemical Hazards