| Revision as of 11:58, 8 March 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL.← Previous edit |
Latest revision as of 20:22, 24 November 2024 edit undoAescley Ezca (talk | contribs)50 editsm added link to parathion methylTag: Visual edit |
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{{chembox |
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{{chembox |
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| verifiedrevid = 402519056 |
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| verifiedrevid = 431610740 |
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| Name = Parathion |
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| Name = Parathion |
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| ImageFile = Methyl&Ethylparathion.png |
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| ImageFile=Methyl&Ethylparathion.png |
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| ImageFile1=Ethyl-parathion-from-AHRLS-2011-3D-balls.png |
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| ImageSize = 220px |
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| PIN = ''O'',''O''-Diethyl ''O''-(4-nitrophenyl) phosphorothioate |
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| ImageName = |
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| OtherNames = E605 |
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| IUPACName = ''O'',''O''-Diethyl ''O''-(4-nitrophenyl) phosphorothioate |
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|Section1={{Chembox Identifiers |
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| OtherNames = E605 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| Section1 = {{Chembox Identifiers |
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| SMILES = S=P(Oc1ccc(cc1)()=O)(OCC)OCC |
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| ChEBI = 27928 |
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| SMILES = S=P(Oc1ccc(cc1)()=O)(OCC)OCC |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 13844817 |
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| ChemSpiderID = 13844817 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| InChI = 1/C10H14NO5PS/c1-3-14-17(18,15-4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3 |
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| InChI = 1/C10H14NO5PS/c1-3-14-17(18,15-4-2)16-10-7-5-9(6-8-10)11(12)13/h5-8H,3-4H2,1-2H3 |
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| InChIKey = LCCNCVORNKJIRZ-UHFFFAOYAR |
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| InChIKey = LCCNCVORNKJIRZ-UHFFFAOYAR |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 261919 |
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| ChEMBL = 261919 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 56-38-2 |
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| CASNo = 56-38-2 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| RTECS = |
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| KEGG = C06604 |
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| PubChem = 991 |
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| RTECS = TF4550000 |
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| EC_number = 200-271-7 |
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| UNNumber = 3018 2783 |
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| Beilstein = 2059093 |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=10 | H=14 | N=1 | O=5 | P=1 | S=1 |
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| Formula = C<sub>10</sub>H<sub>14</sub>NO<sub>5</sub>PS |
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| Appearance = White crystals (pure form) |
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| MolarMass = 291.3 g/mol |
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| Solubility = 24 mg/L |
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| Appearance = White crystals (pure form) |
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| Solubility = 24mg/L in water, high solubility |
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| SolubleOther = high solubility |
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in ] or ] |
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in ] and ] |
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| Solvent = other solvents |
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| MeltingPt = 6 °C |
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| MeltingPtC = 6 |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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| FlashPt = 120 °C |
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| RPhrases = {{R24}}, {{R26/28}}, {{R48/25}}, {{R50/53}} |
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| SPhrases = {{S28}}, {{S36/37}}, {{S45}}, {{S60}}, {{S61}} |
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}} |
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}} |
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|Section7={{Chembox Hazards |
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| ExternalSDS = |
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| NFPA-H = 4 |
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| NFPA-F = 1 |
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| NFPA-R = 2 |
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| NFPA-S = |
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| FlashPtC = 120 |
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| GHSPictograms = {{GHS06}}{{GHS08}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|300|311|330|372|410}} |
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| PPhrases = {{P-phrases|260|264|270|271|273|280|284|301+310|302+352|304+340|310|312|314|320|321|322|330|361|363|391|403+233|405|501}} |
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| PEL = none (methyl parathion),<ref name=PGCH|0427>{{PGCH|0427}}</ref> TWA 0.1 mg/m<sup>3</sup> (ethyl parathion)<ref name=PGCH|0479/> |
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| REL = TWA 0.2 mg/m<sup>3</sup> (methyl parathion)<ref name=PGCH|0427/> TWA 0.05 mg/m3 (ethyl parathion)<ref name=PGCH|0479/> |
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| IDLH = N.D. (methyl parathion)<ref name=PGCH|0427/> 10 mg/m<sup>3</sup> (ethyl parathion)<ref name=PGCH|0479>{{PGCH|0479}}</ref> |
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| LCLo = 50 mg/m<sup>3</sup> (rabbit, 2 hr)<br/>14 mg/m<sup>3</sup> (guinea pig, 2 hr)<br/>15 mg/m<sup>3</sup> (mouse)<ref name=IDLH>{{IDLH|56382|Parathion}}</ref> |
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| LC50 = 84 mg/m<sup>3</sup> (rat, 4 hr)<ref name=IDLH/> |
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| LD50 = 5 mg/kg (mouse, oral)<br/>10 mg/kg (rabbit, oral)<br/>3 mg/kg (dog, oral)<br/>0.93 mg/kg (cat, oral)<br/>5 mg/kg (horse, oral)<br/>8 mg/kg (guinea pig, oral)<br/>2 mg/kg (rat, oral)<ref name=IDLH/> |
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}}<ref>{{cite web |url=http://www.ehs.neu.edu/laboratory_safety/general_information/nfpa_hazard_rating/documents/NFPAratingJR.htm |title=Hazard Rating Information for NFPA Fire Diamonds |access-date=2015-03-13 |url-status=dead |archive-url=https://web.archive.org/web/20150217114741/http://www.ehs.neu.edu/laboratory_safety/general_information/nfpa_hazard_rating/documents/NFPAratingJR.htm |archive-date=2015-02-17 }}</ref> |
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'''Parathion''', also called '''parathion-ethyl''' or '''diethyl parathion''', is an ]. It is a potent ] and ]. It was originally developed by ] in the 1940s. It is highly toxic to non-target organisms, including humans. Its use is banned or restricted in many countries, and there are proposals to ban it from all use. Closely related is "methyl parathion" (see below). |
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==Parathion-methyl== |
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"Parathion-methyl" (CAS#298-00-0), also known as methyl parathion or dimethyl parathion, was also developed and is marketed for similar uses. It is a distinct compound with diminished toxicity. Some trade names of parathion-methyl include '''Bladan M''', '''Metaphos''', '''ME605''', and '''E601'''. |
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'''Parathion''', also called '''parathion-ethyl''' or '''diethyl parathion''', is an ] ] and ]. It was originally developed by ] in the 1940s. It is highly toxic to non-target organisms, including humans, so its use has been banned or restricted in most countries. In response to safety concerns, the less toxic but still dangerous analogue ] was later developed.<ref>{{Cite web|url=http://www.fao.org/3/w5715e/w5715e05.htm|title=Parathion|website=www.fao.org|access-date=2020-04-17}}</ref> |
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<center>]</center> |
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==History== |
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==History== |
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Parathion was developed by Dr. ] for the ] trust ] in the 1940s. After the war and the collapse of IG Farben due to the war crime trials, the Western allies seized the ], and parathion was marketed worldwide by different companies and under different brand names. The most common German brand was '''E605''' (banned in Germany after 2002); this was not a food-additive "]" as used in the EU today. "E" stands for ''Entwicklungsnummer'' (German for "development number"). |
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Parathion was developed by ] for the German trust ] in the 1940s. After ] and the collapse of IG Farben due to the war crime trials, the Western allies seized the ], and parathion was marketed worldwide by different companies and under different brand names. The most common German brand was '''E605''' (banned in Germany after 2002); this was not a food-additive "]" as used in the EU today. "E" stands for ''Entwicklungsnummer'' (German for "development number"). It is an irreversible ]. |
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Safety concerns later led to the development of ], which is somewhat less toxic. |
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In the ], Parathion was banned after 2001. <ref> </ref> In ], the substance is no longer approved as a pesticide. |
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==Handling properties== |
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==Handling properties== |
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When pure, parathion is a white crystalline solid, however it is commonly distributed as a brown ] that smells of rotting ]s or ]. The insecticide is more or less stable, although it darkens when exposed to sunlight. |
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Pure parathion is a white crystalline solid. It is commonly distributed as a brown ] that smells of rotting ]s or ]. The insecticide is somewhat stable, although it darkens when exposed to sunlight. |
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==Industrial synthesis== |
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==Industrial synthesis== |
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Parathion is synthesized from ] (C<sub>2</sub>H<sub>5</sub>O)<sub>2</sub>PS<sub>2</sub>H, which is obtained by treatment of ] with ethanol (] is used to prepare methyl parathion). Diethyl dithiophosphoric acid is chlorinated to generate diethylthiophosphoryl chloride. The diethyl dithiophosphoric acid is then treated with ] (the ] ] of ]).<ref name = fee>Fee, D. C.; Gard, D. R.; Yang, C. “Phosphorus Compounds” Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons: New York, 2005. {{DOI|10.1002/0471238961.16081519060505.a01.pub2}}.</ref> |
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Parathion is synthesized from ] {{chem2|(C2H5O)2PS2H}} by ] to generate diethylthiophosphoryl chloride ({{chem2|(C2H5O)2P(S)Cl}}), and then the chloride is treated with ] (the ] ] of ]).<ref name = fee>{{cite book |last1=Fee |first1=D. C. |last2=Gard |first2=D. R. |last3=Yang |first3=C. |chapter=Phosphorus Compounds |title=Kirk-Othmer Encyclopedia of Chemical Technology |publisher=John Wiley & Sons |location=New York |year=2005 |doi=10.1002/0471238961.16081519060505.a01.pub2 |isbn=978-0471238966 }}</ref> |
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: 2 (C<sub>2</sub>H<sub>5</sub>O)<sub>2</sub>P(S)SH + 3 Cl<sub>2</sub> → 2 (C<sub>2</sub>H<sub>5</sub>O)<sub>2</sub>P(S)Cl + S<sub>2</sub>Cl<sub>2</sub> + 2 HCl |
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:{{chem2|2 (C2H5O)2P(S)SH + 3 Cl2 → 2 (C2H5O)2P(S)Cl + S2Cl2 + 2 HCl}} |
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:{{chem2|(C2H5O)2P(S)Cl + NaOC6H4NO2 → (C2H5O)2P(S)OC6H4NO2 + NaCl}} |
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: (C2H5O)<sub>2</sub>P(S)Cl + NaOC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub> → (C<sub>2</sub>H<sub>5</sub>O)<sub>2</sub>P(S)OC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub> + NaCl |
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==Applications== |
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==Applications== |
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==Insecticidal activity== |
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==Insecticidal activity== |
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Parathion acts on the enzyme ], but indirectly. After being ingested by insects (and unintentionally, by humans), the parathion becomes oxidized by ]s to give ], replacing the double bonded sulfur with oxygen.<ref name = metcalf>Metcalf, R. L. “Insect Control” Ullman’s Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA: New York, 2002. {{DOI| 10.1002/14356007.a14_263}}.</ref> |
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Parathion acts on the enzyme ] indirectly. After an insect (or a human) ingests parathion, an ] replaces the double bonded sulfur with oxygen to give ].<ref name = metcalf>{{cite book |last=Metcalf |first=R. L. |chapter=Insect Control |title=Ullmann's Encyclopedia of Industrial Chemistry |publisher=Wiley-VCH Verlag GmbH & Co. KGaA |location=New York |year=2002 |doi=10.1002/14356007.a14_263 |isbn=978-3527306732 }}</ref> |
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:{{chem2|(C2H5O)2P(S)OC6H4NO2 + 1/2 O2 → (C2H5O)2P(O)OC6H4NO2 + S}} |
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:(C<sub>2</sub>H<sub>5</sub>O)<sub>2</sub>P(S)OC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub> + 1/2 O<sub>2</sub> → (C<sub>2</sub>H<sub>5</sub>O)<sub>2</sub>P(O)OC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub> + S |
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The phosphate ester is more reactive in organisms than the phosphorothiolate ester, as the phosphorus atoms become much more electronegative.<ref name = metcalf/> |
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The phosphate ester is more reactive in organisms than the phosphorothiolate ester, as the phosphorus atoms become much more electropositive.<ref name = metcalf/> |
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Parathion {{visible anchor|Resistance|text=resistance}} is a special case of ]. |
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==Degradation== |
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==Degradation== |
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Degradation of parathion leads to more water soluble products. ], which deactivates the molecule, occurs at the ] bond resulting in ] and ].<ref name = metcalf/> |
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Degradation of parathion leads to more water-soluble products. ], which deactivates the molecule, occurs at the ] bond resulting in ] and ].<ref name = metcalf/> |
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:{{chem2|(C2H5O)2P(S)OC6H4NO2 + H2O → HOC6H4NO2 + (C2H5O)2P(S)OH}} |
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:(C<sub>2</sub>H<sub>5</sub>O)<sub>2</sub>P(S)OC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub> + H<sub>2</sub>O → HOC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub> + (C<sub>2</sub>H<sub>5</sub>O)<sub>2</sub>P(S)OH |
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Degradation proceeds differently under ] conditions: the nitro group on parathion is reduced to the ]. |
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Degradation proceeds differently under ] conditions: the nitro group on parathion is reduced to the ]. |
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:{{chem2|(C2H5O)2P(S)OC6H4NO2 + 6 H → (C2H5O)2P(S)OC6H4NH2 + 2 H2O}} |
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:(C<sub>2</sub>H<sub>5</sub>O)<sub>2</sub>P(S)OC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub> + 6 H → (C<sub>2</sub>H<sub>5</sub>O)<sub>2</sub>P(S)OC<sub>6</sub>H<sub>4</sub>NH<sub>2</sub> + 2 H<sub>2</sub>O |
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==Safety== |
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==Safety== |
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Parathion is a ]. It generally disrupts the ] by inhibiting the ]. It is absorbed via skin, mucous membranes, and orally. Absorbed parathion is rapidly metabolized to paraoxon, as described above. Paraoxon exposure can result in ]s, ], poor vision, ], abdominal pain, severe ], ], ], ], and finally ] as well as respiratory arrest. Symptoms of poisoning are known to last for extended periods of time, sometimes months. The most common and very specific antidote is ] in doses of up to 100 mg daily. Because atropine may also be toxic, it is recommended that small frequently repeated doses be used in treatment. If human poisoning is detected early and the treatment is prompt (atropine and artificial respiration), fatalities are infrequent. Insufficient oxygen will lead to ] and permanent brain damage. ] including ] is noticed as late ] after recovery from acute intoxication. Parathion has been used for committing suicide and deliberately poisoning other persons. It is known as "Schwiegermuttergift" (mother-in-law poison) in Germany. For this reason most formulations contain a blue dye providing warning. |
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Parathion is a ]. It generally disrupts the ] by inhibiting ]. It is absorbed via skin, mucous membranes, and orally. Absorbed parathion is rapidly metabolized to paraoxon, as described in ]. Paraoxon exposure can result in ]s, ], poor vision, ], abdominal pain, severe ], ], ], ], and finally ] as well as respiratory arrest. Symptoms of poisoning are known to last for extended periods, sometimes months. The most common and very specific antidote is ], in doses of up to 100 mg daily. Because atropine may also be toxic, it is recommended that small frequently repeated doses be used in treatment. If human poisoning is detected early and the treatment is prompt (atropine and artificial respiration), fatalities are infrequent. Insufficient oxygen will lead to ] and permanent brain damage. ] including ] is noticed as late ] after recovery from acute intoxication. Parathion and related organophosphorus pesticides are used in hundreds of thousands of poisonings annually, especially suicides.<ref>Litchfield, M.H. "Estimates of acute pesticide poisoning in agricultural workers in less developed countries" Toxicology Reviews 2005, volume 24, pp. 271-8. {{PMID|16499408}}</ref> It is known as ''Schwiegermuttergift'' (mother-in-law poison) in Germany. For this reason, most formulations contain a blue dye providing warning. |
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Parathion was used as a ] agent, most notably by an element of the ] attached to the ] during the ]. They used it to poison clothing that was then supplied to anti-government guerrillas. When the enemy soldiers put on the clothes, they were poisoned by absorption through the skin.<ref>{{Cite web|url=https://openaccess.leidenuniv.nl/bitstream/handle/1887/68698/Poison%20in%20Rhodesia%2C%20Colm%20Wittenberg.pdf?sequence=1|title = Poison in Rhodesia|date = 31 January 2019}}</ref><ref>{{Cite web|url=http://cco.ndu.edu/News/Article/1506904/dirty-war-rhodesia-and-chemical-biological-warfare-1975-1980-book-review/|title=Dirty War: Rhodesia and Chemical Biological Warfare 1975-1980 (Book Review)|website=PRISM | National Defense University}}</ref><ref>{{cite book|title=Dirty War: Rhodesia and Chemical Biological Warfare, 1975–1980|last=Cross|first=Glenn|year=2017|location=Solihull, UK|publisher=Helion & Company|isbn=978-1-911512-12-7}}</ref> |
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Based on animal studies, parathion is considered by the ] to be a possible human ].<ref name=epa>{{cite web | title = Parathion | work = Integrated Risk Information System | publisher = ] | date = 26 January 2007 | url = http://www.epa.gov/iris/subst/0327.htm}}</ref> Studies show that parathion is toxic to fetuses, but does not cause birth defects.<ref name = extoxnet>{{cite web | work = Extension Toxicology Network | title = Pesticide Information Profiles - Parathion | publisher = ] | month = September | year = 1993 | url = http://extoxnet.orst.edu/pips/parathio.htm}}</ref> |
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Based on animal studies, parathion is considered by the ] to be a possible human ].<ref name=epa>{{cite web | title = Parathion | work = Integrated Risk Information System | publisher = ] | date = 26 January 2007 | url = http://www.epa.gov/iris/subst/0327.htm}}</ref> Studies show that parathion is toxic to fetuses, but does not cause birth defects.<ref name = extoxnet>{{cite web | work = Extension Toxicology Network | title = Pesticide Information Profiles - Parathion | publisher = ] |date=September 1993 | url = http://extoxnet.orst.edu/pips/parathio.htm}}</ref> |
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It is classified as a ] ] and ] ], "Ia, Extremely Hazardous". |
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It is classified by the ] as a ]{{cn|date=February 2018}} and by the ] as ] (extremely hazardous).{{cn|date=February 2018}} |
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Parathion is very toxic to ], ], ]s, and other forms of wildlife.<ref name = extoxnet/> Parathion can be replaced by many safer and less toxic alternatives (less toxic ]s, ]s, or synthetic ]s). |
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Parathion is toxic to ], ], ]s, and other forms of wildlife.<ref name = extoxnet/> |
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===Protection against poisoning=== |
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===Protection against poisoning=== |
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To assure human protection the end user must wear protective gloves, clothing, and a respirator of the organic-vapour. ] during the production process requires special ventilation and continuous measurement of air contamination in order not to exceed PEL levels as well as keeping personal hygiene. Frequent determination of workers' serum acetylcholinesterase activity is also helpful in regards of occupational safety, because the action of parathion is cumulative. If an area of the body is contaminated with parathion, if possible, it should be removed immediately. Also, atropine has been used as a specific antidote. |
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To provide the end user with a minimum standard of protection, suitable protective gloves, clothing, and a respirator with organic-vapour cartridges is normally worn. ] during the production process requires special ventilation and continuous measurement of air contamination in order not to exceed PEL levels, as well as careful attention to personal hygiene. Frequent analysis of workers' serum acetylcholinesterase activity is also helpful with regards to occupational safety, because the action of parathion is cumulative. Also, atropine has been used as a specific antidote.{{fact|date=January 2024}} |
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=== Use in suicides === |
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==Proposals to ban== |
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A chemist {{who?|date=March 2024}} swallowed {{convert|.00424|oz|g}} of parathion {{when?|date=March 2024}} to find the most lethal means of exposure to humans, intending to take an antidote afterwards, but was paralyzed and so died before he could reach it.<ref name=":0">{{Cite book |last=Carson |first=Rachel |url=http://worldcat.org/oclc/1346358856 |title=Silent Spring |publisher= HarperCollins|year=1962 |isbn=978-0-547-52762-8 |oclc=1346358856}}</ref> |
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According to the non-governmental organisation ] or PAN, parathion is one of the most dangerous pesticides. This organization lists parathion also as a 'bad actor chemical'.<ref name = panid>{{cite web | title = Parathion - Identification, toxicity, use, water pollution potential, ecological toxicity and regulatory information | publisher = ] | author = S. Kegley, B. Hill, S. Orme | url = http://pesticideinfo.org/Detail_Chemical.jsp?Rec_Id=PC35122}}</ref> In the US alone more than 650 agricultural workers have been poisoned since 1966, of which 100 died. In underdeveloped countries many more people have suffered fatal and nonfatal intoxications. The ], PAN and numerous environmental organisations propose a general and global ban. Its use is banned or restricted in 23 countries and its import is illegal in a total of 50 countries.<ref name=panid/> |
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Parathion was commonly used for suicides in the 1950s and 1960s.<ref name=":0" /> |
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==See also== |
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==See also== |
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* ] |
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* ] |
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* ] |
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==References== |
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==References== |
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==External links== |
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==External links== |
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* {{PPDB|506}} |
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* U.S. ] (public domain) |
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* U.S. ] (public domain) |
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* U.S. ] (public domain) |
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* Ethyl parathion: {{ICSC|0006}} |
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* Ethyl parathion: {{ICSC|0006}} |
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* Methyl parathion: {{ICSC|0626}} |
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* Methyl parathion: {{ICSC|0626}} |
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{{Insecticides}} |
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{{Insecticides}} |
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{{Acetylcholine metabolism and transport modulators}} |
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] |
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] |
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