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 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).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.
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.
Safety The TLV-TWA for 1,3-dichloropropene (DCP) is 1 ppm.Robert L. Metcalf "Insect Control" in Ullmann's Encyclopedia of Industrial Chemistry" Wiley-VCH, Wienheim, 2002. It is a contact irritant. A wide range of complications have been reported.
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.
Use 1,3-Dichloropropene is used as a pesticide in the following crops:
+ 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.
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.
References
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