| Revision as of 15:40, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464789476 of page 2,4,5-Trichlorophenoxyacetic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 13:39, 7 November 2024 edit RustyOldShip (talk | contribs)495 editsm added ink to chlorophenoxy herbicide |
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{{More medical citations needed|date=January 2015}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443262205 |
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| verifiedrevid = 477198470 |
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| Name = 2,4,5-Trichlorophenoxyacetic acid |
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| ImageFile = 2,4,5-T.svg |
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| Name = 2,4,5-Trichlorophenoxyacetic acid |
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| ImageFile = 2,4,5-Trichlorophenoxyacetic_acid_structure_numbered.svg |
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| ImageSize = 200px |
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| ImageName = 2,4,5-Trichlorophenoxyacetic acid |
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| ImageSize = 210px |
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| ImageName = 2,4,5-Trichlorophenoxyacetic acid |
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| IUPACName = (2,4,5-Trichlorophenoxy)acetic acid |
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| ImageFile1 = 2,4,5-Trichlorophenoxyacetic-acid-3D-balls.png |
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| ImageSize1 = 220px |
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| OtherNames = 2,4,5-Trichlorophenoxyacetic acid<br />2,4,5-T<br />Trioxone |
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| ImageAlt1 = Ball-and-stick model of 2,4,5-T |
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| Section1 = {{Chembox Identifiers |
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| PIN = (2,4,5-Trichlorophenoxy)acetic acid |
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| SMILES = Clc1cc(OCC(=O)O)c(Cl)cc1Cl |
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| OtherNames = 2,4,5-Trichlorophenoxyacetic acid<br />2,4,5-T<br />Trioxone |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|Section1={{Chembox Identifiers |
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| CASNo = 93-76-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Beilstein = 2055620 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 27903 |
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| ChEBI = 27903 |
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| ChemSpiderID = 1435 |
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| ChemSpiderID = 1435 |
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| EINECS = 202-273-3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 9Q963S4YMX |
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| Gmelin = 434052 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C07100 |
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| KEGG = C07100 |
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| PubChem = 1480 |
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| RTECS = AJ8400000 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 9Q963S4YMX |
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| UNNumber = 2811 3345 3348 2765 |
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| InChI = 1/C8H5Cl3O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13/h1-2H,3H2,(H,12,13) |
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| InChI = 1/C8H5Cl3O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13/h1-2H,3H2,(H,12,13) |
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| InChIKey = SMYMJHWAQXWPDB-UHFFFAOYAR |
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| InChIKey = SMYMJHWAQXWPDB-UHFFFAOYAR |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 194458 |
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| ChEMBL = 194458 |
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| SMILES = Clc1cc(OCC(=O)O)c(Cl)cc1Cl |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C8H5Cl3O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13/h1-2H,3H2,(H,12,13) |
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| StdInChI = 1S/C8H5Cl3O3/c9-4-1-6(11)7(2-5(4)10)14-3-8(12)13/h1-2H,3H2,(H,12,13) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SMYMJHWAQXWPDB-UHFFFAOYSA-N |
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| StdInChIKey = SMYMJHWAQXWPDB-UHFFFAOYSA-N |
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| CASNo = 93-76-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| RTECS = AJ8400000 |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=8|H=5|Cl=3|O=3 |
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| C=8 | H=5 | Cl=3 | O=3 |
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| MolarMass = 255.48 g/mol |
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| MolarMass = 255.48 g/mol |
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| Appearance = Off-white to yellow crystalline solid |
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| Appearance = Off-white to yellow crystalline solid |
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| Odor = odorless |
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| Density = 1.80 g/cm³, 20 °C |
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| Solubility = 238 mg/kg (30 °C) |
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| Density = 1.80 g/cm<sup>3</sup>, 20 °C |
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| MeltingPt = 154-158 °C |
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| Solubility = 238 mg/kg (30 °C) |
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| MeltingPtC = 154 to 158 |
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| BoilingPt = |
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| MeltingPt_notes = |
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| pKa = |
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| BoilingPt = |
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| Viscosity = |
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| BoilingPt_notes = decomposes<ref name=PGCH/> |
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| pKa = |
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| Viscosity = |
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| VaporPressure = {{val|1|e=−7|ul=mmHg}}<ref name=PGCH/> |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| GHSPictograms = {{GHS07}}{{GHS09}} |
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| RPhrases = 22-36/37/38-50/53 |
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| GHSSignalWord = Warning |
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| SPhrases = 24-60-61 |
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| HPhrases = {{H-phrases|302|315|319|335|410}} |
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| PPhrases = {{P-phrases|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}} |
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| IDLH = 250 mg/m<sup>3</sup><ref name=PGCH>{{PGCH|0583}}</ref> |
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| LD50 = 381 mg/kg (guinea pig, oral)<br/>300 mg/kg (rat, oral)<br/>425 mg/kg (hamster, oral)<br/>242 mg/kg (mouse, oral)<ref>{{IDLH|93765|2,4,5-T}}</ref> |
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| REL = TWA 10 mg/m<sup>3</sup><ref name=PGCH/> |
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| PEL = TWA 10 mg/m<sup>3</sup><ref name=PGCH/> |
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}} |
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| Section8 = {{Chembox Related |
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|Section8={{Chembox Related |
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| OtherCpds = ]<br />] |
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| OtherCompounds = ]<br />] |
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'''2,4,5-Trichlorophenoxyacetic acid''' (also known as '''2,4,5-T'''), a synthetic ], is a ] acetic acid ] used to ] broad-leafed plants. It was developed in the late 1940s, synthesized by reaction of ] and chloroacetic acid. It was widely used in the agricultural industry until being phased out, starting in the late 1970s due to toxicity concerns. ], a defoliant used by the British in the ] and the U.S. in the ], was equal parts 2,4,5-T and ] (2,4-dichlorophenoxyacetic acid). 2,4,5-T itself is toxic with a ] of 3 mg/kg/day and a ] of 10 mg/kg/day.<ref>{{cite book |title=The US-Malaysian nexus: Themes in superpower-small state relations |pages=284–290 |publisher=Institute of Strategic and International Studies, Malaysia |author=Pamela Sodhy |year=1991}}</ref> ] 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 ] (TCDD).<ref>{{Cite journal |last=Hites |first=Ronald A. |date=2010-09-03 |title=Dioxins: An Overview and History |url=http://dx.doi.org/10.1021/es1013664 |journal=Environmental Science & Technology |volume=45 |issue=1 |pages=16–20 |doi=10.1021/es1013664 |pmid=20815379 |issn=0013-936X}}</ref> TCDD is a ] ] 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 .005 ppm.{{citation needed|date=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.{{citation needed|date=January 2015}} |
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In 1970, the ] halted the use of 2,4,5-T on all food crops except rice, and in 1985, the ] 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.<ref>{{cite news|title=Backgrounder: 2,4,5-T Use in Ontario|url=https://news.ontario.ca/mnr/en/2013/06/245-t-use-in-ontario.html|access-date=9 March 2018|publisher=Ministry of Natural Resources and Forestry|date=13 June 2013}}</ref> The international trade of 2,4,5-T is restricted by the ]. 2,4,5-T has since largely been replaced by ] and ]. |
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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 and hepatic injury, and delayed neuropathy. Cometabolism of 2,4,5-T is possible to produce 3,5-dichlorocatechol<ref>{{citation|title=Microbial Co-Metabolism and the Degradation of Organic Compounds in Nature |pages=146–155 |publisher=Bacteriological Reviews, American Society for Microbiology, Vol. 6, No. 2 |author=Raymond S. Horvath |date=June 1972}}</ref> which, in turn, can be degraded by ''Pseudomonas'' bacteria.<ref>{{citation|title=Plasmids in Pseudomonas |pages=7–30 |publisher=Annual Review of Genetics, Vol. 10 |author=A. M. Chakrabarty |journal=Annual Review of Genetics |year=1976|volume=10 |doi=10.1146/annurev.ge.10.120176.000255 |pmid=797315 }}</ref> |
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IARC considers the chlorophenoxyacetic acids group of chemicals as ] to humans.<ref>{{Citation |
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| title = Biomonitoring Summary |
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| url = https://www.cdc.gov/biomonitoring/2,4,5-TrichlorophenoxyaceticAcid_BiomonitoringSummary.html |
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| author = CDC |
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}}</ref> |
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==Incidents== |
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{{Incomplete list|date=December 2022}} |
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In 1963 a production vessel for 2,4,5-T exploded in the Philips-Duphar plant in the Netherlands.<ref name=":0">{{Cite book|url=https://books.google.com/books?id=uyISBQAAQBAJ&q=Philips-Duphar+2%2C4%2C5+T+explosion&pg=PA281|title=Hazard Assessment of Chemicals: Current Developments|last=Saxena|first=Jitendra|date=2013-10-22|publisher=Elsevier|isbn=9781483261898|language=en}}</ref> Six workers that cleaned up afterwards got seriously intoxicated and developed ].<ref name=":0" /> After twelve years, four of the six cleaners had died.{{Citation needed|date=January 2019}} |
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==References== |
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{{reflist}} |
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==Further reading== |
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* Tschirley FH. Defoliation in Vietnam. Science. 1969;163:779-786. |
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* Orians GH, Pfeiffer EW. Ecological effects of the war in Vietnam. Science. 1970;168:544-554. |
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* Neilands JB, Orians GH, Pfeiffer EW, Vennema A, Westing AH. Harvest of Death: Chemical Warfare in Vietnam and Cambodia. New York: Free Press; 1972. |
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* Gochfeld M. The other victims of the Vietnam war. BioScience. 1975;25:540-541. |
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* Westing AH, ed. Herbicides in War. The Long Term Ecological and Human Consequences. London: Taylor and Francis; 1984. |
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* 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. |
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* 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. |
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* 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. |
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* 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. |
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* WGBH (Television station : Boston, Mass.), director. A Plague on Our Children. Time Life Multimedia, 1979.<ref>{{Cite web|url=https://archive.org/details/APlagueOnOurChildren/NOVA.S06E11.A.Plague.on.our.Children.Part1.Dioxins.1979.VHSRip.AAC2.0.x264-astro.mp4|title = A Plague on Our Children|year = 1980}}</ref> |
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== External links == |
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{{Herbicides}} |
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{{DEFAULTSORT:Trichlorophenoxyacetic acid, 2, 4, 5-}} |
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