1,3-Dichloropropene

1,3-dichloropropane June 2023 changed changed 477205208 Trans-1,3-Dichloropropene.svg skin-invert-image 120px Skeletal formula of the trans isomer Cis-1,3-Dichloropropene.svg skin-invert-image 120px Skeletal formula of the cis isomer Trans-1,3-Dichloropropene-3D-balls.png bg-transparent 120px Ball-and-stick model of the trans isomer Cis-1,3-Dichloropropene-3D-balls.png bg-transparent 120px Ball-and-stick model of the cis isomer 1,3-Dichloroprop-1-ene AQL Agrocelhone, DD92, 1,3-D, Dorlone, Nematox, Telone,Martin Frank N. Development of Alternative Strategies for Management of Soilborne Pathogens Currently Controlled with Methyl Bromide Annual Review of Phytopathology Annual Reviews 41 1 2003 0066-4286 10.1146/annurev.phyto.41.052002.095514 325–350 14527332 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 correct chemspider 23117 UOORRWUZONOOLO-OWOJBTEDBJ correct chemspider 1S/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+ correct chemspider UOORRWUZONOOLO-OWOJBTEDSA-N correct CAS 542-75-6 208-826-5 correct EBI 155926 24726 correct FDA 9H780918D0 Cl[C@H]=CCCl 1/C3H4Cl2/c4-2-1-3-5/h1-2H,3H2/b2-1+ UC8310000 2047 1,3-dichloro-1-propene changed EBI 18918 correct kegg C18627 C3H4Cl2 110.97 g/mol Colorless to straw-colored liquid sweet, chloroform-like 1.217 g/mL (cis); 1.224 g/mL (trans) -84.5 104 (cis); 112 °C (trans) 2.18 g/L (cis) @ 25 °C; 2.32 g/L (trans) @ 25 °C 1.82 34.4 mm Hg @ 25 °C (cis); 23.0 mm Hg @ 25 °C (trans) 2 3 0 05 06 07 08 09 Danger 226 301 302 305 311 315 317 319 331 332 335 410 210 233 240 241 242 243 261 264 270 271 272 273 280 301+310 302+352 303+361+353 304+312 304+340 305+351+338 311 312 321 322 330 331 332+313 333+313 337+313 361 362 363 370+378 391 403+233 403+235 405 501 28 > 500 5.3% – 14.5% (80 °C) none0199 Ca TWA 1 ppm (5 mg/m3) [skin] Ca [N.D.] 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).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.Krähling Ludger Allyl Compounds 2000-06-15 https://doi.org/10.1002/14356007.a01_425 Ullmann's Encyclopedia of Industrial Chemistry Weinheim, Germany Wiley-VCH Verlag GmbH & Co. KGaA 10.1002/14356007.a01_425 2022-03-18 Krey Jürgen Jakobson Gerald Grolig Johann Miksche Leopold 3527306730 subscription 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.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 https://www.sciencedirect.com/science/article/pii/S004520680400029X Bioorganic Chemistry Mechanistic Enzymology en 32 5 376–392 10.1016/j.bioorg.2004.05.006 15381403 0045-2068 subscription 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. 10.1002/14356007.a14_263 It is a contact irritant. A wide range of complications have been reported.https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsLanding.aspx?id=835&tid=163 ToxFAQs – Letter A Toxic Substance Portal ATSDR 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:National Totals of Pesticide Use (pounds applied and acres treated) by Crop and Compound http://ca.water.usgs.gov/pnsp/crop/ dead https://web.archive.org/web/20070410025543/http://ca.water.usgs.gov/pnsp/crop/ 2007-04-10 United States Geological Survey + 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.September 2008 TOXICOLOGICAL PROFILE FOR DICHLOROPROPENES http://www.atsdr.cdc.gov/toxprofiles/tp40.pdf Agency for Toxic Substances and Disease Registry frame|class=skin-invert-image|none|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 2020 yes has been licensed to Telos Ag Solutions and is no longer a Corteva product.Telone soil fumigant to be distributed by Telos Ag Solutions Vegetable Growers News 2020-11-17 http://vegetablegrowersnews.com/news/telone-soil-fumigant-to-be-distributed-by-telos-ag-solutions/ 2021-07-06 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 Category:Pesticides Category:Chloroalkenes Category:IARC Group 2B carcinogens Category:Fumigants Category:Sweet-smelling chemicals