1,3-Dichloropropene Explained

1,3-Dichloropropene should not be confused with 1,3-dichloropropane.

1,3-Dichloropropene, sold under diverse trade names, is an organochlorine compound with the formula . 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).[1]

Production, chemical properties, biodegradation

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

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.[2]

Safety

The TLV-TWA for 1,3-dichloropropene (DCP) is 1 ppm.[3] It is a contact irritant. A wide range of complications have been reported.[4]

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.[5] 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.[4]

Use

1,3-Dichloropropene is used as a pesticide in the following crops:[6]

1,3-Dichloropropene Use in Crops! Crop !! Pounds (lb) !! Primary Pesticide?
Tobacco12,114,887 Yes
Potatoes12,044,736 Yes
Sugar Beets5,799,613 Yes
Cotton3,735,543 Yes
Peanuts3,463,003 Yes
Sweet Potatoes1,210,872 Yes
Onions674,183 Yes
Carrots531,752 Yes
Watermelons133,801 No
Cantaloups121,395 No
Cucumbers76,735 No
Strawberries71,753 No
Sweet Peppers28,247 No
Melons12,471 No
Blueberries3,090 No
Asparagus1,105 No

Contamination

The ATSDR has extensive contamination information available.[7]

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 has been licensed to Telos Ag Solutions and is no longer a Corteva product.[8]

References

Further reading

Notes and References

  1. https://eur-lex.europa.eu/legal-content/EN/TXT/PDF/?uri=CELEX:32022R0740&from=EN COMMISSION DECISION of 13 May 2022 concerning the non-approval of the active substance 1,3-dichloropropene
  2. 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 . Bioorganic Chemistry . Mechanistic Enzymology . en . 32 . 5 . 376–392 . 10.1016/j.bioorg.2004.05.006 . 15381403 . 0045-2068.
  3. Robert L. Metcalf "Insect Control" in Ullmann's Encyclopedia of Industrial Chemistry" Wiley-VCH, Wienheim, 2002.
  4. Web site: ToxFAQs – Letter A Toxic Substance Portal ATSDR.
  5. Web site: 2022-06-21 . Proposition 65: No Significant Risk Level for 1,3-Dichloropropene (1,3-D) . 2022-10-26 . oehha.ca.gov.
  6. Web site: National Totals of Pesticide Use (pounds applied and acres treated) by Crop and Compound . dead . https://web.archive.org/web/20070410025543/http://ca.water.usgs.gov/pnsp/crop/ . 2007-04-10 . United States Geological Survey.
  7. Web site: September 2008 . TOXICOLOGICAL PROFILE FOR DICHLOROPROPENES . Agency for Toxic Substances and Disease Registry.
  8. Web site: Telone soil fumigant to be distributed by Telos Ag Solutions . Vegetable Growers News . 2020-11-17 . 2021-07-06.