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id="siteSub" class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"><span class="mw-redirectedfrom">(Redirected from <a href="/w/index.php?title=Ethoprop&redirect=no" class="mw-redirect" title="Ethoprop">Ethoprop</a>)</span></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <style data-mw-deduplicate="TemplateStyles:r1268415487">.mw-parser-output .ib-chembox{border-collapse:collapse;text-align:left}.mw-parser-output .ib-chembox td,.mw-parser-output .ib-chembox th{border:1px solid #a2a9b1;width:40%}.mw-parser-output .ib-chembox td+td{width:60%}@media screen{html.skin-theme-clientpref-night .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .ib-chembox figure:not(.skin-invert-image):not(.skin-invert):not(.bg-transparent){background:var(--background-color-inverted,#f8f9fa)}}</style> <table class="infobox ib-chembox"> <caption>Ethoprophos </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ethoprophos.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Ethoprophos.svg/200px-Ethoprophos.svg.png" decoding="async" width="200" height="92" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/4/46/Ethoprophos.svg/300px-Ethoprophos.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/4/46/Ethoprophos.svg/400px-Ethoprophos.svg.png 2x" data-file-width="173" data-file-height="80" /></a><figcaption></figcaption></figure> </td></tr> <tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Ethoprophos.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Ethoprophos.png/200px-Ethoprophos.png" decoding="async" width="200" height="118" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Ethoprophos.png/300px-Ethoprophos.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6e/Ethoprophos.png/400px-Ethoprophos.png 2x" data-file-width="2902" data-file-height="1715" /></a><figcaption></figcaption></figure> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names </th></tr> <tr> <td colspan="2" style="text-align:left;"><a href="/wiki/Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a> <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;"><i>O</i>-Ethyl <i>S</i>,<i>S</i>-dipropyl phosphorodithioate</div></div> </td></tr> <tr> <td colspan="2" style="text-align:left;">Other names <div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Ethoprophos, Prophos, Mocap</div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div> </td> <td><style data-mw-deduplicate="TemplateStyles:r1126788409">.mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=13194-48-4">13194-48-4</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=O%3DP%28SCCC%29%28OCC%29SCCC">Interactive image</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=38665">CHEBI:38665</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL1894994">ChEMBL1894994</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.chemspider.com"><a rel="nofollow" class="external text" href="https://www.chemspider.com/Chemical-Structure.3173.html">3173</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a> </td> <td><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.032.851">100.032.851</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q411754#P2566" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span> </td></tr> <tr> <td><a href="/wiki/European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>236-152-1</li></ul></div> </td></tr> <tr> <td><a href="/wiki/KEGG" title="KEGG">KEGG</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C18687">C18687</a></span></li></ul></div> </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="pubchem.ncbi.nlm.nih.gov"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/3289">3289</a></span></li></ul></div> </td></tr> <tr> <td><a href="/wiki/RTECS" class="mw-redirect" title="RTECS">RTECS number</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>TE4025000</li></ul></div> </td></tr> <tr> <td><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="precision.fda.gov"><a rel="nofollow" class="external text" href="https://precision.fda.gov/uniisearch/srs/unii/765Y5683OQ">765Y5683OQ</a></span><sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></li></ul></div> </td></tr> <tr> <td><a href="/wiki/UN_number" title="UN number">UN number</a> </td> <td>3018 </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID4032611">DTXSID4032611</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q411754#P3117" title="Edit this at Wikidata"><img alt="Edit this at Wikidata" src="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/10px-OOjs_UI_icon_edit-ltr-progressive.svg.png" decoding="async" width="10" height="10" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/15px-OOjs_UI_icon_edit-ltr-progressive.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/8/8a/OOjs_UI_icon_edit-ltr-progressive.svg/20px-OOjs_UI_icon_edit-ltr-progressive.svg.png 2x" data-file-width="20" data-file-height="20" /></a></span></span></li></ul></div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C8H19O2PS2/c1-4-7-12-11(9,10-6-3)13-8-5-2/h4-8H2,1-3H3<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: VJYFKVYYMZPMAB-UHFFFAOYSA-N<sup> <span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span></sup></div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C8H19O2PS2/c1-4-7-12-11(9,10-6-3)13-8-5-2/h4-8H2,1-3H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: VJYFKVYYMZPMAB-UHFFFAOYAE</div></div></li></ul> </div> </td></tr> <tr> <td colspan="2"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="/wiki/Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div> <ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.6em; word-wrap:break-word; text-indent:-1.5em; text-align:left; font-size:97%; line-height:120%;">O=P(SCCC)(OCC)SCCC</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Chemical_formula" title="Chemical formula">Chemical formula</a></div> </td> <td><span title="Carbon">C</span><sub>8</sub><span title="Hydrogen">H</span><sub>19</sub><span title="Oxygen">O</span><sub>2</sub><span title="Phosphorus">P</span><span title="Sulfur">S</span><sub>2</sub> </td></tr> <tr> <td><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a> </td> <td><span class="nowrap"><span data-sort-value="7002242330000000000♠"></span>242.33</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>Colourless to yellow clear liquid </td></tr> <tr> <td><a href="/wiki/Odor" title="Odor">Odor</a> </td> <td><a href="/wiki/Mercaptan" class="mw-redirect" title="Mercaptan">Mercaptan</a>-like </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.069 g/ml </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td><-70 °C (-94 °F, 203 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>244.3 °C (471.7 °F, 517.5 K) (decomposes) </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></div> </td> <td>1.3-1.4 mg/L (water) </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>78 mPa (20 °C), 128 mPa (25 °C) </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards </th></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b><a href="/wiki/Occupational_safety_and_health" title="Occupational safety and health">Occupational safety and health</a></b> (OHS/OSH): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Main hazards</div> </td> <td>Toxic </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div> </td> <td><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-silhouette.svg" class="mw-file-description" title="GHS08: Health hazard"><img alt="GHS08: Health hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/50px-GHS-pictogram-silhouette.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/75px-GHS-pictogram-silhouette.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/2/21/GHS-pictogram-silhouette.svg/100px-GHS-pictogram-silhouette.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><span typeof="mw:File"><a href="/wiki/File:GHS-pictogram-pollu.svg" class="mw-file-description" title="GHS09: Environmental hazard"><img alt="GHS09: Environmental hazard" src="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/50px-GHS-pictogram-pollu.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/75px-GHS-pictogram-pollu.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/b/b9/GHS-pictogram-pollu.svg/100px-GHS-pictogram-pollu.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div> </td> <td><b>Danger</b> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div> </td> <td><abbr class="abbr" title="H301: Toxic if swallowed">H301</abbr>, <abbr class="abbr" title="H310: Fatal in contact with skin">H310</abbr>, <abbr class="abbr" title="H317: May cause an allergic skin reaction">H317</abbr>, <abbr class="abbr" title="H330: Fatal if inhaled">H330</abbr>, <abbr class="abbr" title="H410: Very toxic to aquatic life with long lasting effects">H410</abbr> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div> </td> <td><abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</abbr>, <abbr class="abbr" title="P261: Avoid breathing dust/fume/gas/mist/vapours/spray.">P261</abbr>, <abbr class="abbr" title="P262: Do not get in eyes, on skin, or on clothing.">P262</abbr>, <abbr class="abbr" title="P264: Wash ... thoroughly after handling.">P264</abbr>, <abbr class="abbr" title="P270: Do not eat, drink or smoke when using this product.">P270</abbr>, <abbr class="abbr" title="P271: Use only outdoors or in a well-ventilated area.">P271</abbr>, <abbr class="abbr" title="P272: Contaminated work clothing should not be allowed out of the workplace.">P272</abbr>, <abbr class="abbr" title="P273: Avoid release to the environment.">P273</abbr>, <abbr class="abbr" title="P280: Wear protective gloves/protective clothing/eye protection/face protection.">P280</abbr>, <abbr class="abbr" title="P284: Wear respiratory protection.">P284</abbr>, <abbr class="abbr" title="P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.">P301+P310</abbr>, <abbr class="abbr" title="P302+P350: IF ON SKIN: Gently wash with soap and water.">P302+P350</abbr>, <abbr class="abbr" title="P302+P352: IF ON SKIN: Wash with soap and water.">P302+P352</abbr>, <abbr class="abbr" title="P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P304+P340</abbr>, <abbr class="abbr" title="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr>, <abbr class="abbr" title="P320: Specific treatment is urgent (see ... on this label).">P320</abbr>, <abbr class="abbr" title="P321: Specific treatment (see ... on this label).">P321</abbr>, <abbr class="abbr" title="P322: Specific measures (see ... on this label).">P322</abbr>, <abbr class="abbr" title="P330: Rinse mouth.">P330</abbr>, <abbr class="abbr" title="P333+P313: If skin irritation or a rash occurs: Get medical advice/attention.">P333+P313</abbr>, <abbr class="abbr" title="P361: Remove/Take off immediately all contaminated clothing.">P361</abbr>, <abbr class="abbr" title="P363: Wash contaminated clothing before reuse.">P363</abbr>, <abbr class="abbr" title="P391: Collect spillage.">P391</abbr>, <abbr class="abbr" title="P403+P233: Store in a well ventilated place. Keep container tightly closed.">P403+P233</abbr>, <abbr class="abbr" title="P405: Store locked up.">P405</abbr>, <abbr class="abbr" title="P501: Dispose of contents/container to ...">P501</abbr> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>141 °C </td></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Autoignition_temperature" title="Autoignition temperature">Autoignition<br />temperature</a></div> </td> <td>280 °C (536 °F; 553 K) </td></tr> <tr> <td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="/wiki/Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div> <div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/12px-Yes_check.svg.png" decoding="async" width="12" height="12" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/18px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/24px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span> <span class="reflink plainlinks nourlexpansion"><a class="external text" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=445074416&page2=Ethoprophos">verify</a></span> (<a href="/wiki/Wikipedia:WikiProject_Chemicals/Chembox_validation" title="Wikipedia:WikiProject Chemicals/Chembox validation">what is</a> <sup><span typeof="mw:File"><span><img alt="check" src="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/7px-Yes_check.svg.png" decoding="async" width="7" height="7" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/11px-Yes_check.svg.png 1.5x, //upload.wikimedia.org/wikipedia/en/thumb/f/fb/Yes_check.svg/14px-Yes_check.svg.png 2x" data-file-width="600" data-file-height="600" /></span></span><span style="display:none">Y</span><span typeof="mw:File"><span><img alt="☒" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/7px-X_mark.svg.png" decoding="async" width="7" height="8" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/11px-X_mark.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/a2/X_mark.svg/14px-X_mark.svg.png 2x" data-file-width="525" data-file-height="600" /></span></span><span style="display:none">N</span></sup> ?) </div></div> <div style="margin-top: 0.3em; text-align: center;"><a href="/wiki/Wikipedia:Chemical_infobox#References" title="Wikipedia:Chemical infobox">Infobox references</a></div> </td></tr> </tbody></table><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Chemical compound</div> <p><b>Ethoprophos</b> (or <b>ethoprop</b>) is an <a href="/wiki/Organophosphate" title="Organophosphate">organophosphate ester</a> with the formula C<sub>8</sub>H<sub>19</sub>O<sub>2</sub>PS<sub>2</sub>.<sup id="cite_ref-:1_1-0" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> It is a clear yellow to colourless liquid that has a characteristic <a href="/wiki/Thiol" title="Thiol">mercaptan</a>-like odour. It is used as an <a href="/wiki/Insecticide" title="Insecticide">insecticide</a> and <a href="/wiki/Nematicide" title="Nematicide">nematicide</a><sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and it is an <a href="/wiki/Acetylcholinesterase_inhibitor" title="Acetylcholinesterase inhibitor">acetylcholinesterase inhibitor</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="Synthesis">Synthesis</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethoprophos&action=edit&section=1" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ethoprop can be synthesised by reacting <a href="/wiki/Phosphoryl_chloride" title="Phosphoryl chloride">phosphoryl chloride</a> with two equivalents of <a href="/wiki/Propanethiol" title="Propanethiol"><i>n</i>-propylmercaptan</a> and one equivalent of <a href="/wiki/Sodium_ethoxide" title="Sodium ethoxide">sodium ethoxide</a>. A second pathway is reacting <i>n</i>-propylmercaptan and sodium ethoxide with <a href="/wiki/Phosphorus_trichloride" title="Phosphorus trichloride">phosphorus trichloride</a> to yield ethoxy-bis(propylsulfanyl)phosphane, which can then be oxidized by <a href="/wiki/Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> to yield the product.<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <dl><dd><figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Ethoprophos_Synthesis_1.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/Ethoprophos_Synthesis_1.png/299px-Ethoprophos_Synthesis_1.png" decoding="async" width="299" height="189" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/3/37/Ethoprophos_Synthesis_1.png/449px-Ethoprophos_Synthesis_1.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/3/37/Ethoprophos_Synthesis_1.png/598px-Ethoprophos_Synthesis_1.png 2x" data-file-width="1287" data-file-height="814" /></a><figcaption>Two syntheses of ethoprop. The only difference is the order in which the alkyl groups are attached</figcaption></figure><div style="clear:left;" class=""></div></dd></dl> <dl><dd><figure class="mw-halign-left" typeof="mw:File/Thumb"><a href="/wiki/File:Ethoprophos_Synthesis_2.png" class="mw-file-description"><img alt="" src="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Ethoprophos_Synthesis_2.png/500px-Ethoprophos_Synthesis_2.png" decoding="async" width="500" height="95" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Ethoprophos_Synthesis_2.png/750px-Ethoprophos_Synthesis_2.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/a/ac/Ethoprophos_Synthesis_2.png/1000px-Ethoprophos_Synthesis_2.png 2x" data-file-width="2003" data-file-height="379" /></a><figcaption>A different synthesis of ethoprop starting from phosphorus trichloride</figcaption></figure><div style="clear:left;" class=""></div></dd></dl> <div class="mw-heading mw-heading2"><h2 id="Applications">Applications</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethoprophos&action=edit&section=2" title="Edit section: Applications"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Ethoprop is used as an <a href="/wiki/Insecticide" title="Insecticide">insecticide</a> against soil insects like <a href="/wiki/Click_beetle" title="Click beetle">wireworms</a> and as a <a href="/wiki/Nematicide" title="Nematicide">nematicide</a>. It is used on different crops, ranging from potatoes, bananas, and sugarcane to ornamental plants and tobacco.<sup id="cite_ref-:1_1-1" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Most of the ethoprop used in the United States is applied to potatoes. In the period of 1987 to 1996, an estimated total of 691,000 pounds (313,400 kg) of the pesticide were used on field crops and vegetables.<sup id="cite_ref-:0_5-0" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Toxicology">Toxicology</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethoprophos&action=edit&section=3" title="Edit section: Toxicology"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Mechanism_of_action">Mechanism of action</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethoprophos&action=edit&section=4" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When an organism is exposed to ethoprophos either via the oral, dermal or inhalation routes, it primarily inhibits carboxyl ester hydrolases, specifically <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">acetylcholinesterase</a> (AChE). This enzyme is important in degradation of the neurotransmitter <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a> (ACh). Inactivation of AChE takes place by <a href="/wiki/Phosphorylation" title="Phosphorylation">phosphorylation</a> of <a href="/wiki/Serine" title="Serine">serine</a> hydroxyl group at the active site of AChE. Later, phosphorylation is followed by one of the following scenarios:<sup id="cite_ref-:2_6-0" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p> <ul><li>endogenous hydrolysis of the phosphorylated enzyme by <a href="/wiki/Esterase" title="Esterase">esterases</a> or <a href="/wiki/Paraoxonase" title="Paraoxonase">paraoxonases</a>;</li> <li>reaction by a strong <a href="/wiki/Nucleophile" title="Nucleophile">nucleophile</a> such as <a href="/wiki/Pralidoxime" title="Pralidoxime">pralidoxime</a> (2-PAM);</li> <li>irreversible binding and permanent enzyme inactivation (also called aging).</li></ul> <p>When AChE is inactivated, ACh accumulates in the nervous system, which then results in overstimulation of <a href="/wiki/Muscarinic_acetylcholine_receptor" title="Muscarinic acetylcholine receptor">muscarinic</a> and <a href="/wiki/Nicotinic_acetylcholine_receptor" title="Nicotinic acetylcholine receptor">nicotinic</a> receptors.<sup id="cite_ref-:2_6-1" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> </p><p>Another target of ethoprophos is <a href="/wiki/Red_blood_cell" title="Red blood cell">erythrocyte</a> acetylcholinesterase. The only known location of this enzyme is on the outside of erythrocyte membranes. However, physiological functions of this AChE type are not completely known.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> </p><p>In cases of exposure to ethoprophos, symptoms may include vomiting, nausea, diarrhea, <a href="/wiki/Miosis" title="Miosis">miosis</a>, abdominal cramps, <a href="/wiki/Dyspnoea" class="mw-redirect" title="Dyspnoea">dyspnoea</a>, muscular weakness, bronchial hypersecretion, anxiety, confusion and convulsions. In case of ethoprophos poisoning, a combination of <a href="/wiki/Atropine" title="Atropine">atropine</a> and <a href="/wiki/Pralidoxime" title="Pralidoxime">pralidoxime</a> (2-PAM) is the most effective antidote.<sup id="cite_ref-:1_1-2" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Additionally, ethoprophos is thought to be likely carcinogenic due to the occurrence of different types of tumors in rats after exposure to the compound. Dietary exposure (the most common route of exposure to ethoprophos) is so low, however, that there is a low risk for the general U.S. population.<sup id="cite_ref-:0_5-1" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metabolism">Metabolism</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethoprophos&action=edit&section=5" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In mammals, metabolism usually proceeds by removal of one or both of the <a href="/wiki/Propyl_group" title="Propyl group">propyl</a> groups and subsequent <a href="/wiki/Drug_metabolism" title="Drug metabolism">conjugation</a>. In rats, metabolism is independent of sex, dose, <a href="/wiki/Route_of_administration" title="Route of administration">route of administration</a>, or repeated administration, and no parent compound is detectable in faeces or urine. The main metabolite in humans is EPPA, shown below, which can be used as a <a href="/wiki/Biomarker" title="Biomarker">biomarker</a> for ethoprophos. The dealkylated metabolites have similar toxic effects to the parent compound.<sup id="cite_ref-:1_1-3" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-default-size mw-halign-none" typeof="mw:File/Thumb"><a href="/wiki/File:EPPA.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/EPPA.png/220px-EPPA.png" decoding="async" width="220" height="89" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/f/f6/EPPA.png/330px-EPPA.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/f/f6/EPPA.png/440px-EPPA.png 2x" data-file-width="629" data-file-height="255" /></a><figcaption>The structure of the main metabolite in humans, EPPA.</figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Distribution_&_Excretion"><span id="Distribution_.26_Excretion"></span>Distribution & Excretion</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethoprophos&action=edit&section=6" title="Edit section: Distribution & Excretion"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In tested animals, ethoprophos is widely distributed throughout the body, with the highest concentrations in the lungs, kidneys, and liver. In blood, it is mostly associated to cells instead of being in the plasma. Excretion mainly proceeds through the urine (~60%), but faecal excretion (~10%) and expired air (~15%) are also important routes. Intravenously dosed animals showed limited biliary excretion (~8%).<sup id="cite_ref-:1_1-4" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Effects_on_animals">Effects on animals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethoprophos&action=edit&section=7" title="Edit section: Effects on animals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Experiments carried out on ethoprophos have shown that the toxin affects animals in various manners. Short-term toxicity effects in rabbits and mice, exposed through different routes include inhibition of <a href="/wiki/Erythrocyte" class="mw-redirect" title="Erythrocyte">erythrocyte</a> and brain <a href="/wiki/Cholinesterase" title="Cholinesterase">cholinesterase</a>. While experiments on dogs gave rise to cellular <a href="/wiki/Vacuolization" title="Vacuolization">vacuolisation</a> as well.<sup id="cite_ref-:1_1-5" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Acute toxicity studies on rats, in turn have resulted in more effects being observed, namely narcotic, <a href="/wiki/Cholinergic" title="Cholinergic">cholinergic</a> and respiratory. The latter was shown to be expressed after a delay of 4 days and linked to an increase in lung weight.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> Studies carried out with extended exposure of ethoprophos in mice gave the same results as research on short-term exposure had, but in rats a fall in <a href="/wiki/Hemoglobin" title="Hemoglobin">hemoglobin</a> concentrations was also observed.<sup id="cite_ref-:1_1-6" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> On the other hand, a long-term exposure experiment conducted on dogs found that the toxin led to mild liver toxicity.<sup id="cite_ref-:0_5-2" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p><p>Furthermore, exposure to ethoprophos was found to affect reproduction as well. Parental toxicity in rats resulted in a drop in their body weight and food consumption. Moreover, abortion cases increased, leading to a reduction of litter sizes. On the other hand, offspring toxicity led to a decrease in body weight gain and rise in postnatal mortality.<sup id="cite_ref-:1_1-7" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p><p>Ethoprophos is considered to pose a low risk to mammals exposed to contaminated water as well as mammals feeding on contaminated fish. It is, however, extremely toxic to bees under direct exposure and also to birds which are exposed to the toxin through dietary routes. These involve ingestion of seeds or worms including residues of contaminated soil.<sup id="cite_ref-:1_1-8" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Finally, a study showed that ethoprophos, along with 4 other active substances, was responsible for 40% of the utilized pesticides in Costa Rica, yet they contributed to more than three quarters of the aquatic toxicity.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> Thus, it has also been concluded to be highly toxic to aquatic species.<sup id="cite_ref-:1_1-9" class="reference"><a href="#cite_note-:1-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Exposure">Exposure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethoprophos&action=edit&section=8" title="Edit section: Exposure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>When orally exposed to ethoprophos, absorption is fast and extensive: the time it takes to reach peak blood levels is below 1 hour and more than 90% of the substance is absorbed.<sup id="cite_ref-:2_6-2" class="reference"><a href="#cite_note-:2-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Short-term dermal exposure to liquid ethoprophos was tested in rabbits in a 21 day long study. The dermal <a href="/wiki/NOAEL" class="mw-redirect" title="NOAEL">NOAE</a>L was 0.1 mg/kg/day and the researchers found that there was <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">acetylcholinesterase</a> inhibition in plasma, <a href="/wiki/Red_blood_cell" title="Red blood cell">erythrocytes</a> and in the brain at a dose of 1.0 mg/kg/day. The short-term dermal exposure to granular ethoprophos was also studied. This study was conducted with rats and lasted for 28 days. In this case, a dermal NOAEL of 20 mg/kg/day was found. Acetylcholinesterase inhibition in plasma happened at a dose of 100 mg/kg/day. For short-term inhalation, a study was done with dogs and it lasted for 90 days. The results showed a NOAEL of 0.025 mg/kg/day and the acetylcholinesterase inhibition in plasma occurred at a dose of 0.075 mg/kg/day. No information about intermediate and long term exposure via dermal and inhalation routes is known at this moment. When rats were chronically exposed to ethoprophos with a dose of 2.81 x 10^-2 mg/kg/day, a number of rats developed malignant adrenal <a href="/wiki/Pheochromocytoma" title="Pheochromocytoma">pheochromocytomas</a>. For granular products, inhalation exposure is considered to be the main risk. In the case of liquid products dermal exposure is considered to be the main risk.<sup id="cite_ref-:0_5-3" class="reference"><a href="#cite_note-:0-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="References">References</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Ethoprophos&action=edit&section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap"><ol class="references"> <li id="cite_note-:1-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:1_1-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:1_1-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-:1_1-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-:1_1-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-:1_1-6"><sup><i><b>g</b></i></sup></a> <a href="#cite_ref-:1_1-7"><sup><i><b>h</b></i></sup></a> <a href="#cite_ref-:1_1-8"><sup><i><b>i</b></i></sup></a> <a href="#cite_ref-:1_1-9"><sup><i><b>j</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite id="CITEREFArenaAuteriBarmazBrancato2018" class="citation journal cs1">Arena, Maria; Auteri, Domenica; Barmaz, Stefania; Brancato, Alba; Brocca, Daniela; Bura, Laszlo; Cabrera, Luis Carrasco; Chiusolo, Arianna; Civitella, Consuelo (2018). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7009744">"Peer review of the pesticide risk assessment of the active substance ethoprophos"</a>. <i>EFSA Journal</i>. <b>16</b> (10): e05290. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.2903%2Fj.efsa.2018.5290">10.2903/j.efsa.2018.5290</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1831-4732">1831-4732</a>. <a href="/wiki/PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7009744">7009744</a></span>. <a href="/wiki/PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/32625701">32625701</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=EFSA+Journal&rft.atitle=Peer+review+of+the+pesticide+risk+assessment+of+the+active+substance+ethoprophos&rft.volume=16&rft.issue=10&rft.pages=e05290&rft.date=2018&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7009744%23id-name%3DPMC&rft.issn=1831-4732&rft_id=info%3Apmid%2F32625701&rft_id=info%3Adoi%2F10.2903%2Fj.efsa.2018.5290&rft.aulast=Arena&rft.aufirst=Maria&rft.au=Auteri%2C+Domenica&rft.au=Barmaz%2C+Stefania&rft.au=Brancato%2C+Alba&rft.au=Brocca%2C+Daniela&rft.au=Bura%2C+Laszlo&rft.au=Cabrera%2C+Luis+Carrasco&rft.au=Chiusolo%2C+Arianna&rft.au=Civitella%2C+Consuelo&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC7009744&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthoprophos" class="Z3988"></span></span> </li> <li id="cite_note-2"><span class="mw-cite-backlink"><b><a href="#cite_ref-2">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFBunt1975" class="citation thesis cs1">Bunt, J. 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"Investigation of the acute toxicity of some trimethyl and triethyl phosphorothioates with particular reference to those causing lung damage". <i>Archives of Toxicology</i>. <b>51</b> (3): <span class="nowrap">221–</span>231. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1007%2FBF00348854">10.1007/BF00348854</a>. <a href="/wiki/ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/1432-0738">1432-0738</a>. <a href="/wiki/S2CID_(identifier)" class="mw-redirect" title="S2CID (identifier)">S2CID</a> <a rel="nofollow" class="external text" href="https://api.semanticscholar.org/CorpusID:44188825">44188825</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Archives+of+Toxicology&rft.atitle=Investigation+of+the+acute+toxicity+of+some+trimethyl+and+triethyl+phosphorothioates+with+particular+reference+to+those+causing+lung+damage&rft.volume=51&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E221-%3C%2Fspan%3E231&rft.date=1982-12-01&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A44188825%23id-name%3DS2CID&rft.issn=1432-0738&rft_id=info%3Adoi%2F10.1007%2FBF00348854&rft.aulast=Verschoyle&rft.aufirst=R.+D.&rft.au=Cabral%2C+J.+R.+P.&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthoprophos" class="Z3988"></span></span> </li> <li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFHumbert2007" class="citation journal cs1">Humbert, Sébastien (January 2007). "Toxicity assessment of the main pesticides used in Costa Rica". <i>Agriculture, Ecosystems & Environment</i>. <b>118</b> (<span class="nowrap">1–</span>4): <span class="nowrap">183–</span>190. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.agee.2006.05.010">10.1016/j.agee.2006.05.010</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Agriculture%2C+Ecosystems+%26+Environment&rft.atitle=Toxicity+assessment+of+the+main+pesticides+used+in+Costa+Rica&rft.volume=118&rft.issue=%3Cspan+class%3D%22nowrap%22%3E1%E2%80%93%3C%2Fspan%3E4&rft.pages=%3Cspan+class%3D%22nowrap%22%3E183-%3C%2Fspan%3E190&rft.date=2007-01&rft_id=info%3Adoi%2F10.1016%2Fj.agee.2006.05.010&rft.aulast=Humbert&rft.aufirst=S%C3%A9bastien&rfr_id=info%3Asid%2Fen.wikipedia.org%3AEthoprophos" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://login.wikimedia.org/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=0" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Ethoprophos&oldid=1247206670">https://en.wikipedia.org/w/index.php?title=Ethoprophos&oldid=1247206670</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Organophosphate_insecticides" title="Category:Organophosphate insecticides">Organophosphate insecticides</a></li><li><a href="/wiki/Category:Phosphorodithioates" title="Category:Phosphorodithioates">Phosphorodithioates</a></li><li><a href="/wiki/Category:Acetylcholinesterase_inhibitors" title="Category:Acetylcholinesterase inhibitors">Acetylcholinesterase inhibitors</a></li><li><a href="/wiki/Category:Propyl_compounds" title="Category:Propyl compounds">Propyl compounds</a></li><li><a href="/wiki/Category:Ethoxy_compounds" title="Category:Ethoxy compounds">Ethoxy compounds</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_matches_Wikidata" title="Category:Short description matches Wikidata">Short description matches Wikidata</a></li><li><a href="/wiki/Category:ECHA_InfoCard_ID_from_Wikidata" title="Category:ECHA InfoCard ID from Wikidata">ECHA InfoCard ID from Wikidata</a></li><li><a href="/wiki/Category:Chembox_having_GHS_data" title="Category:Chembox having GHS data">Chembox having GHS data</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li><li><a href="/wiki/Category:Chembox_image_size_set" title="Category:Chembox image size set">Chembox image size set</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 23 September 2024, at 08:41<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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