2,4,5-Trichlorophenoxyacetic acid

January 2015 changed 477198470 2,4,5-Trichlorophenoxyacetic acid 2,4,5-Trichlorophenoxyacetic_acid_structure_numbered.svg 210px 2,4,5-Trichlorophenoxyacetic acid 2,4,5-Trichlorophenoxyacetic-acid-3D-balls.png 220px Ball-and-stick model of 2,4,5-T (2,4,5-Trichlorophenoxy)acetic acid 2,4,5-Trichlorophenoxyacetic acid2,4,5-TTrioxone 93-76-5 correct CAS 2055620 correct chemspider correct EBI 27903 1435 202-273-3 434052 correct kegg C07100 1480 AJ8400000 correct FDA 9Q963S4YMX 2811 3345 3348 2765 1/C8H5Cl3O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13/h1-2H,3H2,(H,12,13) SMYMJHWAQXWPDB-UHFFFAOYAR correct EBI 194458 Clc1cc(OCC(=O)O)c(Cl)cc1Cl correct chemspider 1S/C8H5Cl3O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13/h1-2H,3H2,(H,12,13) correct chemspider SMYMJHWAQXWPDB-UHFFFAOYSA-N 8 5 3 3 255.48 g/mol Off-white to yellow crystalline solid odorless 1.80 g/cm3, 20 °C 238 mg/kg (30 °C) 154 to 158 decomposes 1 −7 mmHg 07 09 Warning 302 315 319 335 410 261 264 270 271 273 280 301+312 302+352 304+340 305+351+338 312 321 330 332+313 337+313 362 391 403+233 405 501 250 mg/m30583 381 mg/kg (guinea pig, oral)300 mg/kg (rat, oral)425 mg/kg (hamster, oral)242 mg/kg (mouse, oral)93765 2,4,5-T TWA 10 mg/m3 TWA 10 mg/m3 2,4-Dauxin 2,4,5-Trichlorophenoxyacetic acid (also known as 2,4,5-T), a synthetic auxin,Rennie Richard A dictionary of chemistry Oxford university press 2020 978-0-19-884122-7 8th Oxford quick reference Oxford 43 is a chlorophenoxy acetic acid herbicide used to defoliate broad-leafed plants. It was developed in the late 1940s, synthesized by reaction of 2,4,5-trichlorophenol and chloroacetic acid. It was widely used in the agricultural industry until being phased out, starting in the late 1970s due to toxicity concerns, as it tends to become contaminated with dioxins. Agent Orange, a defoliant used by the British in the Malayan Emergency and the U.S. in the Vietnam War, was equal parts 2,4,5-T and 2,4-D (2,4-dichlorophenoxyacetic acid). 2,4,5-T itself is toxic with a NOAEL of 3 mg/kg/day and a LOAEL of 10 mg/kg/day.The US-Malaysian nexus: Themes in superpower-small state relations 284–290 Institute of Strategic and International Studies, Malaysia Pamela Sodhy 1991 Agent Pink contained 100% 2,4,5-T (dioxin contaminates included). Additionally, the manufacturing process for 2,4,5-T contaminates this chemical with trace amounts of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD).Hites Ronald A. 2010-09-03 Dioxins: An Overview and History http://dx.doi.org/10.1021/es1013664 Environmental Science & Technology 45 1 16–20 10.1021/es1013664 20815379 0013-936X subscription TCDD is a carcinogenic persistent organic pollutant with long-term effects on the environment. With proper temperature control during production of 2,4,5-T, TCDD levels can be held to about 5 ppb.January 2015 Before the TCDD risk was well understood, early production facilities lacked proper temperature controls and individual batches tested later were found to have as much as 60 ppm of TCDD.January 2015 In 1970, the United States Department of Agriculture halted the use of 2,4,5-T on all food crops except rice, and in 1985, the EPA terminated all remaining uses in the U.S. of this herbicide. In Canada, the use and sale of 2,4,5-T was prohibited after 1985.Backgrounder: 2,4,5-T Use in Ontario https://news.ontario.ca/mnr/en/2013/06/245-t-use-in-ontario.html 9 March 2018 Ministry of Natural Resources and Forestry 13 June 2013 The international trade of 2,4,5-T is restricted by the Rotterdam Convention. 2,4,5-T has since largely been replaced by dicamba and triclopyr. Human health effects from 2,4,5-T at low environmental doses or at biomonitored levels from low environmental exposures are unknown. Intentional overdoses and unintentional high dose occupational exposures to chlorophenoxy acid herbicides have resulted in weakness, headache, dizziness, nausea, abdominal pain, myotonia, hypotension, renal (kidney) and hepatic (liver) injury, and delayed neuropathy. Cometabolism of 2,4,5-T is possible to produce 3,5-dichlorocatechol,Microbial Co-Metabolism and the Degradation of Organic Compounds in Nature 146–155 Bacteriological Reviews, American Society for Microbiology, Vol. 6, No. 2 Raymond S. Horvath June 1972 which, in turn, can be degraded by Pseudomonas bacteria.Plasmids in Pseudomonas 7–30 Annual Review of Genetics, Vol. 10 A. M. Chakrabarty Annual Review of Genetics 1976 10 10.1146/annurev.ge.10.120176.000255 797315 IARC considers the chlorophenoxyacetic acids group of chemicals as possibly carcinogenic to humans. Biomonitoring Summary https://www.cdc.gov/biomonitoring/2,4,5-TrichlorophenoxyaceticAcid_BiomonitoringSummary.html CDC Incidents December 2022 In 1963 a production vessel for 2,4,5-T exploded in the Philips-Duphar plant in the Netherlands.https://books.google.com/books?id=uyISBQAAQBAJ&q=Philips-Duphar+2%2C4%2C5+T+explosion&pg=PA281 Hazard Assessment of Chemicals: Current Developments Saxena Jitendra 2013-10-22 Elsevier 9781483261898 en Six workers that cleaned up afterwards got seriously intoxicated and developed chloracne. References Further reading Tschirley FH. Defoliation in Vietnam. Science. 1969;163:779-786. Orians GH, Pfeiffer EW. Ecological effects of the war in Vietnam. Science. 1970;168:544-554. Neilands JB, Orians GH, Pfeiffer EW, Vennema A, Westing AH. Harvest of Death: Chemical Warfare in Vietnam and Cambodia. New York: Free Press; 1972. Gochfeld M. The other victims of the Vietnam war. BioScience. 1975;25:540-541. Westing AH, ed. Herbicides in War. The Long Term Ecological and Human Consequences. London: Taylor and Francis; 1984. Schecter AJ, Tong HY, Monson SJ, Goss ML. Levels of 2,3,7,8-TCDD in silt samples collected between 1985 and 1986 from rivers in the North and South of Vietnam. Chemosphere. 1989;19:547-550. Schecter AJM, Dai LC, Thuy LTB, et al. Agent Orange and the Vietnamese: the persistence of elevated dioxin levels in human tissues. Am J Public Health. 1995;85:516-522. Kahn PC, Gochfeld M, Nyugen M, Hansson M, Rappe C, Velez H. Dioxins and dibenzofurans in blood and adipose tissue of Agent Orange-exposed Vietnam veterans and matched controls. JAMA. 1988;259:1661-1667. Fingerhut MA, Halperin WE, Marlow DA, et al. Cancer mortality in workers exposed to 2,3,7,8-tetrachlorodibenzo-p-dioxin. N Engl J Med. 1991;324:212-218. WGBH (Television station : Boston, Mass.), director A Plague on Our Children Time Life Multimedia 1979 https://archive.org/details/APlagueOnOurChildren/NOVA.S06E11.A.Plague.on.our.Children.Part1.Dioxins.1979.VHSRip.AAC2.0.x264-astro.mp4 External links CDC - NIOSH Pocket Guide to Chemical Hazards Category:Obsolete pesticides Category:Auxinic herbicides Category:Acetic acids Category:Phenoxyacetic acids Category:Chlorobenzene derivatives Category:Group 4 herbicides