Chemistry:1,3-Dichloropropene

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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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
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 GHS05: CorrosiveGHS06: ToxicGHS07: HarmfulGHS08: Health hazardGHS09: Environmental hazard
GHS Signal word Danger
H226, H301, H302, H305, H311, H315, H317, H319, H331, H332, H335, 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 codeNFPA 704 four-colored diamond
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[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).
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Infobox references
Tracking categories (test):

1,3-Dichloropropene, sold under diverse trade names, is an organochlorine compound with the formula C
3H
4Cl
2. 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 is widely used in the US and other countries, but is banned in 34 countries (including 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. 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) has been licensed to Telos Ag Solutions and is no longer a Corteva product.[1][2]

References

  1. ↑ 1.0 1.1 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. 
  2. ↑ 2.0 2.1 "Telone soil fumigant to be distributed by Telos Ag Solutions". 2020-11-17. http://vegetablegrowersnews.com/news/telone-soil-fumigant-to-be-distributed-by-telos-ag-solutions/. 
  3. ↑ 3.0 3.1 3.2 NIOSH Pocket Guide to Chemical Hazards. "#0199". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0199.html. 
  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 (2000-06-15), Allyl Compounds, Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, doi:10.1002/14356007.a01_425, ISBN 3527306730, https://doi.org/10.1002/14356007.a01_425, retrieved 2022-03-18 
  6. ↑ Poelarends, Gerrit J.; Whitman, Christian P. (2004-10-01). "Evolution of enzymatic activity in the tautomerase superfamily: mechanistic and structural studies of the 1,3-dichloropropene catabolic enzymes" (in en). Bioorganic Chemistry. Mechanistic Enzymology 32 (5): 376–392. doi:10.1016/j.bioorg.2004.05.006. ISSN 0045-2068. PMID 15381403. https://www.sciencedirect.com/science/article/pii/S004520680400029X. 
  7. ↑ Robert L. Metcalf "Insect Control" in Ullmann's Encyclopedia of Industrial Chemistry" Wiley-VCH, Wienheim, 2002. doi:10.1002/14356007.a14_263
  8. ↑ 8.0 8.1 "ToxFAQs – Letter A | Toxic Substance Portal | ATSDR". https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsLanding.aspx?id=835&tid=163. 
  9. ↑ "Proposition 65: No Significant Risk Level for 1,3-Dichloropropene (1,3-D)". 2022-06-21. https://oehha.ca.gov/proposition-65/crnr/proposition-65-no-significant-risk-level-13-dichloropropene-13-d. 
  10. ↑ "National Totals of Pesticide Use (pounds applied and acres treated) by Crop and Compound". United States Geological Survey. http://ca.water.usgs.gov/pnsp/crop/. 
  11. ↑ "TOXICOLOGICAL PROFILE FOR DICHLOROPROPENES". September 2008. http://www.atsdr.cdc.gov/toxprofiles/tp40.pdf. 

Further reading



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