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<span>Available forms</span> </div> </a> <ul id="toc-Available_forms-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Structure_and_reactivity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Structure_and_reactivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3</span> <span>Structure and reactivity</span> </div> </a> <button aria-controls="toc-Structure_and_reactivity-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Structure and reactivity subsection</span> </button> <ul id="toc-Structure_and_reactivity-sublist" class="vector-toc-list"> <li id="toc-Structure" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Structure"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.1</span> <span>Structure</span> </div> </a> <ul id="toc-Structure-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Reactivity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Reactivity"> <div class="vector-toc-text"> <span class="vector-toc-numb">3.2</span> <span>Reactivity</span> </div> </a> <ul id="toc-Reactivity-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Synthesis" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Synthesis"> <div class="vector-toc-text"> <span class="vector-toc-numb">4</span> <span>Synthesis</span> </div> </a> <ul id="toc-Synthesis-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Mechanism_of_action" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Mechanism_of_action"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Mechanism of action</span> </div> </a> <ul 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id="toc-Biotransformation" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Biotransformation"> <div class="vector-toc-text"> <span class="vector-toc-numb">6.2</span> <span>Biotransformation</span> </div> </a> <ul id="toc-Biotransformation-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Toxicity" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Toxicity</span> </div> </a> <button aria-controls="toc-Toxicity-sublist" class="cdx-button cdx-button--weight-quiet cdx-button--icon-only vector-toc-toggle"> <span class="vector-icon mw-ui-icon-wikimedia-expand"></span> <span>Toggle Toxicity subsection</span> </button> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> <li id="toc-General_toxicity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#General_toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.1</span> <span>General toxicity</span> </div> </a> <ul id="toc-General_toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Metabolite_toxicity" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Metabolite_toxicity"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.2</span> <span>Metabolite toxicity</span> </div> </a> <ul id="toc-Metabolite_toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Health_effects" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#Health_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3</span> <span>Health effects</span> </div> </a> <ul id="toc-Health_effects-sublist" class="vector-toc-list"> <li id="toc-Acute_effects" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Acute_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3.1</span> <span>Acute effects</span> </div> </a> <ul id="toc-Acute_effects-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Long-term_effects" class="vector-toc-list-item vector-toc-level-3"> <a class="vector-toc-link" href="#Long-term_effects"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.3.2</span> <span>Long-term effects</span> </div> </a> <ul id="toc-Long-term_effects-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-2024_deaths_in_South_Africa" class="vector-toc-list-item vector-toc-level-2"> <a class="vector-toc-link" href="#2024_deaths_in_South_Africa"> <div class="vector-toc-text"> <span class="vector-toc-numb">7.4</span> <span>2024 deaths in South Africa</span> </div> </a> <ul id="toc-2024_deaths_in_South_Africa-sublist" class="vector-toc-list"> </ul> </li> </ul> </li> <li id="toc-Detection" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a 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class="vector-unpinned-container"> </div> </div> </div> </nav> <h1 id="firstHeading" class="firstHeading mw-first-heading"><span class="mw-page-title-main">Terbufos</span></h1> <div id="p-lang-btn" class="vector-dropdown mw-portlet mw-portlet-lang" > <input type="checkbox" id="p-lang-btn-checkbox" role="button" aria-haspopup="true" data-event-name="ui.dropdown-p-lang-btn" class="vector-dropdown-checkbox mw-interlanguage-selector" aria-label="Go to an article in another language. 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title="Terbufós – Portuguese" lang="pt" hreflang="pt" data-title="Terbufós" data-language-autonym="Português" data-language-local-name="Portuguese" class="interlanguage-link-target"><span>Português</span></a></li><li class="interlanguage-link interwiki-sr mw-list-item"><a href="https://sr.wikipedia.org/wiki/Terbufos" title="Terbufos – Serbian" lang="sr" hreflang="sr" data-title="Terbufos" data-language-autonym="Српски / srpski" data-language-local-name="Serbian" class="interlanguage-link-target"><span>Српски / srpski</span></a></li><li class="interlanguage-link interwiki-sh mw-list-item"><a href="https://sh.wikipedia.org/wiki/Terbufos" title="Terbufos – Serbo-Croatian" lang="sh" hreflang="sh" data-title="Terbufos" data-language-autonym="Srpskohrvatski / српскохрватски" data-language-local-name="Serbo-Croatian" class="interlanguage-link-target"><span>Srpskohrvatski / српскохрватски</span></a></li> </ul> <div class="after-portlet after-portlet-lang"><span class="wb-langlinks-edit 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by Wikidata [g]" accesskey="g"><span>Wikidata item</span></a></li> </ul> </div> </div> </div> </div> </div> </div> </nav> </div> </div> </div> <div class="vector-column-end"> <div class="vector-sticky-pinned-container"> <nav class="vector-page-tools-landmark" aria-label="Page tools"> <div id="vector-page-tools-pinned-container" class="vector-pinned-container"> </div> </nav> <nav class="vector-appearance-landmark" aria-label="Appearance"> <div id="vector-appearance-pinned-container" class="vector-pinned-container"> <div id="vector-appearance" class="vector-appearance vector-pinnable-element"> <div class="vector-pinnable-header vector-appearance-pinnable-header vector-pinnable-header-pinned" data-feature-name="appearance-pinned" data-pinnable-element-id="vector-appearance" data-pinned-container-id="vector-appearance-pinned-container" data-unpinned-container-id="vector-appearance-unpinned-container" > <div class="vector-pinnable-header-label">Appearance</div> <button 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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>Terbufos </caption> <tbody><tr> <td colspan="2" style="text-align:center; padding:2px;"><figure class="mw-halign-center" typeof="mw:File"><a href="/wiki/File:Terbufos_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/6/60/Terbufos_structure.svg/200px-Terbufos_structure.svg.png" decoding="async" width="200" height="107" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/60/Terbufos_structure.svg/300px-Terbufos_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/60/Terbufos_structure.svg/400px-Terbufos_structure.svg.png 2x" data-file-width="512" data-file-height="275" /></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>S</i>-[(<i>tert</i>-Butylsulfanyl)methyl] <i>O</i>,<i>O</i>-diethyl 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;"><div><ul><li>Counter</li><li>Contraven</li><li>Aragan</li></ul></div></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=13071-79-9">13071-79-9</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=S%3DP%28OCC%29%28SCSC%28C%29%28C%29C%29OCC">Interactive image</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.23912.html">23912</a></span></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/100.032.679">100.032.679</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q2404344#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><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/25670">25670</a></span></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/M83BN0F8R9">M83BN0F8R9</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;"><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/DTXSID2022254">DTXSID2022254</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q2404344#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/C9H21O2PS3/c1-6-10-12(13,11-7-2)15-8-14-9(3,4)5/h6-8H2,1-5H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XLNZEKHULJKQBA-UHFFFAOYSA-N</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/C9H21O2PS3/c1-6-10-12(13,11-7-2)15-8-14-9(3,4)5/h6-8H2,1-5H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: XLNZEKHULJKQBA-UHFFFAOYAH</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%;">S=P(OCC)(SCSC(C)(C)C)OCC</div></li></ul> </div> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> </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>9</sub><span title="Hydrogen">H</span><sub>21</sub><span title="Oxygen">O</span><sub>2</sub><span title="Phosphorus">P</span><span title="Sulfur">S</span><sub>3</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="7002288420000000000♠"></span>288.42</span> g·mol<sup>−1</sup>   </td></tr> <tr> <td>Appearance </td> <td>clear, colorless to pale yellow or reddish-brown liquid </td></tr> <tr> <td><a href="/wiki/Density" title="Density">Density</a> </td> <td>1.105 g/mL (at 24 °C) </td></tr> <tr> <td><a href="/wiki/Melting_point" title="Melting point">Melting point</a> </td> <td>−29.2 °C (−20.6 °F; 244.0 K) </td></tr> <tr> <td><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a> </td> <td>69 °C (156 °F; 342 K) </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 mg/mL </td></tr> <tr> <td><a href="/wiki/Solubility" title="Solubility">Solubility</a> </td> <td>Freely soluble in organic compounds </td></tr> <tr> <td><a href="/wiki/Vapor_pressure" title="Vapor pressure">Vapor pressure</a> </td> <td>0.0003 mmHg </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards<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> </th></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-skull.svg" class="mw-file-description" title="GHS06: Toxic"><img alt="GHS06: Toxic" src="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/50px-GHS-pictogram-skull.svg.png" decoding="async" width="50" height="50" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/75px-GHS-pictogram-skull.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/5/58/GHS-pictogram-skull.svg/100px-GHS-pictogram-skull.svg.png 2x" data-file-width="724" data-file-height="724" /></a></span><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="H227: Combustible liquid">H227</abbr>, <abbr class="abbr" title="H300: Fatal if swallowed">H300</abbr>, <abbr class="abbr" title="H310: Fatal in contact with skin">H310</abbr>, <abbr class="abbr" title="H330: Fatal if inhaled">H330</abbr>, <abbr class="abbr" title="H361: Suspected of damaging fertility or the unborn child">H361</abbr>, <abbr class="abbr" title="H370: Causes damage to organs">H370</abbr>, <abbr class="abbr" title="H372: Causes damage to organs through prolonged or repeated exposure">H372</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="P201: Obtain special instructions before use.">P201</abbr>, <abbr class="abbr" title="P202: Do not handle until all safety precautions have been read and understood.">P202</abbr>, <abbr class="abbr" title="P210: Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.">P210</abbr>, <abbr class="abbr" title="P233: Keep container tightly closed.">P233</abbr>, <abbr class="abbr" title="P235: Keep cool.">P235</abbr>, <abbr class="abbr" title="P260: Do not breathe dust/fume/gas/mist/vapours/spray.">P260</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="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="P281: Use personal protective equipment as required.">P281</abbr>, <abbr class="abbr" title="P284: Wear respiratory protection.">P284</abbr>, <abbr class="abbr" title="P301: IF SWALLOWED:">P301</abbr>, <abbr class="abbr" title="P302: IF ON SKIN:">P302</abbr>, <abbr class="abbr" title="P304: IF INHALED:">P304</abbr>, <abbr class="abbr" title="P307: IF exposed:">P307</abbr>, <abbr class="abbr" title="P308: IF exposed or concerned:">P308</abbr>, <abbr class="abbr" title="P310: Immediately call a POISON CENTER or doctor/physician.">P310</abbr>, <abbr class="abbr" title="P311: Call a POISON CENTER or doctor/physician.">P311</abbr>, <abbr class="abbr" title="P313: Get medical advice/attention.">P313</abbr>, <abbr class="abbr" title="P314: Get Medical advice/attention if you feel unwell.">P314</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="P340: Remove victim to fresh air and keep at rest in a position comfortable for breathing.">P340</abbr>, <abbr class="abbr" title="P350: Gently wash with soap and water.">P350</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="P370: In case of fire:">P370</abbr>, <abbr class="abbr" title="P378: Use ... to extinguish.">P378</abbr>, <abbr class="abbr" title="P391: Collect spillage.">P391</abbr>, <abbr class="abbr" title="P403: Store in a well ventilated place.">P403</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/NFPA_704" title="NFPA 704"><b>NFPA 704</b></a> (fire diamond) </td> <td><style data-mw-deduplicate="TemplateStyles:r1170367383">.mw-parser-output .nfpa-704-diamond-ref{float:right;padding:1px;text-align:right}.mw-parser-output .nfpa-704-diamond-container{width:82px;font-family:sans-serif;margin:0 auto}.mw-parser-output .nfpa-704-diamond-container-ref{float:left;margin-left:1em}.mw-parser-output .nfpa-704-diamond-images{float:left;font-size:20px;text-align:center;position:relative;height:80px;width:80px;padding:1px}.mw-parser-output .nfpa-704-diamond-map{position:absolute;height:80px;width:80px}.mw-parser-output .nfpa-704-diamond .noresize{margin:0 auto}.mw-parser-output .nfpa-704-diamond-code{line-height:1em;text-align:center;position:absolute}.mw-parser-output .nfpa-704-diamond-code>a{color:black}.mw-parser-output .nfpa-704-diamond-blue{width:13px;top:31px;left:15px}.mw-parser-output .nfpa-704-diamond-red{width:12px;top:12px;left:35px}.mw-parser-output .nfpa-704-diamond-yellow{width:13px;top:31px;left:54px}.mw-parser-output .nfpa-704-diamond-white-image{position:relative;top:51px;left:0}.mw-parser-output .nfpa-704-diamond-white-text{vertical-align:middle;text-align:center;line-height:80%;position:absolute;top:52px}.mw-parser-output .nfpa-704-diamond-white-text a>span{position:absolute;color:black}.mw-parser-output .nfpa-704-diamond-white-wors{font-size:15px;width:23px;left:29px}.mw-parser-output .nfpa-704-diamond-white-wox{font-size:15px;font-stretch:condensed;width:21px;line-height:80%;top:-4px;left:29px}.mw-parser-output .nfpa-704-diamond-white-abcp{font-size:13.5px;font-stretch:condensed;width:28px;left:26px}.mw-parser-output .nfpa-704-diamond-white-ac{font-size:10px;width:30px;left:25px}.mw-parser-output .nfpa-704-diamond-white-strike{text-decoration:line-through}</style><div class="nfpa-704-diamond notheme"><div class="nfpa-704-diamond-container"><div class="nfpa-704-diamond-images nounderlines"> <div class="nfpa-704-diamond-map"><figure class="noresize" typeof="mw:File"><span><img alt="NFPA 704 four-colored diamond" src="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/80px-NFPA_704.svg.png" decoding="async" width="80" height="80" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/120px-NFPA_704.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/6/6f/NFPA_704.svg/160px-NFPA_704.svg.png 2x" data-file-width="512" data-file-height="512" usemap="#ImageMap_2ddbcbc27824d79c" /></span><map name="ImageMap_2ddbcbc27824d79c"><area href="/wiki/NFPA_704#Blue" shape="poly" coords="23,23,47,47,23,70,0,47" alt="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" /><area href="/wiki/NFPA_704#Red" shape="poly" coords="47,0,70,23,47,47,23,23" alt="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" /><area href="/wiki/NFPA_704#Yellow" shape="poly" coords="70,23,94,47,70,70,47,47" alt="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" /><area href="/wiki/NFPA_704#White" shape="poly" coords="47,47,70,70,47,94,23,70" alt="Special hazards (white): no code" title="Special hazards (white): no code" /></map><figcaption></figcaption></figure></div><div class="nfpa-704-diamond-code nfpa-704-diamond-blue"> <a href="/wiki/NFPA_704#Blue" title="NFPA 704"><span title="Health 4: Very short exposure could cause death or major residual injury. E.g. VX gas" class="notheme mw-no-invert">4</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-red"> <a href="/wiki/NFPA_704#Red" title="NFPA 704"><span title="Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline" class="notheme mw-no-invert">3</span></a></div><div class="nfpa-704-diamond-code nfpa-704-diamond-yellow"> <a href="/wiki/NFPA_704#Yellow" title="NFPA 704"><span title="Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen" class="notheme mw-no-invert">0</span></a></div></div></div></div> </td></tr> <tr> <td><a href="/wiki/Flash_point" title="Flash point">Flash point</a> </td> <td>88 °C (190 °F; 361 K) </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><b>Lethal dose</b> or concentration (LD, LC): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LD<sub>50</sub> (<a href="/wiki/Lethal_dose#LD50" title="Lethal dose">median dose</a>)</div> </td> <td>Rat (male), Oral LD50 = 13 mg/kg <p>Rat (female), Oral LD50 = 8 mg/kg Rat (male), Dermal LD50 = 123 mg/kg Rat (female), Dermal LD50 = 71 mg/kg </p> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">LC<sub>50</sub> (<a href="/wiki/Lethal_dose#LC50" title="Lethal dose">median concentration</a>)</div> </td> <td>Rat (male), Inhalation (4 hr): 0.017 mg/L <p>Rat (female), Inhalation(4 hr): 0.015 mg/L Rat (male), Inhalation (1 hr calculated): 0.068 mg/L Rat (female), Inhalation (1 hr): 0.06 mg/L </p> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/National_Institute_for_Occupational_Safety_and_Health" title="National Institute for Occupational Safety and Health"><b>NIOSH</b></a> (US health exposure limits): </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Permissible_exposure_limit" title="Permissible exposure limit">PEL</a> (Permissible)</div> </td> <td>0 ppm <sup id="cite_ref-osha.gov_2-0" class="reference"><a href="#cite_note-osha.gov-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Recommended_exposure_limit" title="Recommended exposure limit">REL</a> (Recommended)</div> </td> <td>0 ppm <sup id="cite_ref-osha.gov_2-1" class="reference"><a href="#cite_note-osha.gov-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </td></tr> <tr> <td><a href="/wiki/Safety_data_sheet" title="Safety data sheet">Safety data sheet</a> (SDS) </td> <td><a rel="nofollow" class="external autonumber" href="http://www.villacrop.co.za/files/Terbufos%20GR_UCP_MSDS.pdf">[1]</a> </td></tr> <tr> <th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Pharmacology<sup id="cite_ref-:1_4-0" class="reference"><a href="#cite_note-:1-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </th></tr> <tr> <td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Route_of_administration" title="Route of administration">Routes of<br />administration</a></div> </td> <td><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li>Intraocular</li><li>Oral</li><li>Epicutaneous</li><li>Inhalation</li></ul></div> </td></tr> <tr> <td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetics</a>: </td></tr> <tr> <td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></div> </td> <td>Urine (86.9 - 96 %) </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> <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>Terbufos</b> is a <a href="/wiki/Chemical_compound" title="Chemical compound">chemical compound</a> used in <a href="/wiki/Insecticide" title="Insecticide">insecticides</a> and <a href="/wiki/Nematicide" title="Nematicide">nematicides</a>. It is part of the chemical family of <a href="/wiki/Organophosphate" title="Organophosphate">organophosphates</a>. It is a clear, colourless to pale yellow or reddish-brown liquid and sold commercially as granulate.<sup id="cite_ref-:2_5-0" class="reference"><a href="#cite_note-:2-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> </p> <meta property="mw:PageProp/toc" /> <div class="mw-heading mw-heading2"><h2 id="History">History</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Terbufos is used on various crops including bananas, beans, citrus, coffee, groundnuts, sorghum, potatoes, sunflowers and maize as soil cover to combat wireworms, mossy beetles, beet flies and the black bean louse.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup><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> It is not approved for use in the <a href="/wiki/European_Union" title="European Union">European Union</a>.<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> Also the <a href="/wiki/World_Health_Organization" title="World Health Organization">World Health Organization</a> classifies terbufos as a class Ia compound, meaning that terbufos is <a href="/wiki/Toxicity_class#World_Health_Organization" title="Toxicity class">extremely hazardous</a>.<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> The <a href="/wiki/Maximum_Residue_Limit" class="mw-redirect" title="Maximum Residue Limit">maximum residue limit</a> in the European Union is 0.01 mg/kg terbufos for most crops and animal products.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> The compound was first registered in 1974 in the United States, together with a United States patent of organophosphates for use in corn fields to deter corn rootworms.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> Between 1987 and 1996, an average of about 7.5 million pounds (about 3,400 tons) of the compound was used each year.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> In November 2006, BASF sold its global Terbufos insecticide business to American AMVAC (<a href="/wiki/American_Vanguard_Corporation" title="American Vanguard Corporation">American Vanguard Corporation</a>).<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> </p><p><a href="/wiki/Organophosphate_poisoning" title="Organophosphate poisoning">Organophosphate poisoning</a> is not common in the developed world. Most cases of terbufos poisoning occur in the developing world, where protection against pesticides is scarce, but compounds such as terbufos are widespread, uncontrolled by a government and readily available for farmers.<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Available_forms">Available forms</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=2" title="Edit section: Available forms"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Terbufos is available in granules for application in the agricultural sector. The compound is applied at planting in a band or on the seed furrow directly.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Structure_and_reactivity">Structure and reactivity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=3" title="Edit section: Structure and reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Structure">Structure</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=4" title="Edit section: Structure"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Terbufos, also known as S-((<i>tert</i>-butylthio)methyl) O,O-diethyl phosphorodithioate,<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> is a compound classified as an organophosphate. Terbufos consists of a central <a href="/wiki/Phosphorus" title="Phosphorus">phosphorus</a> atom, surrounded by four different groups. This central atom is surrounded by two <a href="/wiki/Ethoxy" class="mw-redirect" title="Ethoxy">ethoxy</a> groups, one double-bonded <a href="/wiki/Sulfur" title="Sulfur">sulfur</a> atom and a (<i>tert</i>-butylthio)methanethiol group. </p> <div class="mw-heading mw-heading3"><h3 id="Reactivity">Reactivity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=5" title="Edit section: Reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Terbufos is practically insoluble in water, but can be dissolved freely in organic compounds. It decomposes after prolonged heating at 120 °C<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:3_19-0" class="reference"><a href="#cite_note-:3-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> and can be hydrolysed when exposed to strong bases (pH>9) and acids (pH<2).<sup id="cite_ref-:3_19-1" class="reference"><a href="#cite_note-:3-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <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=Terbufos&action=edit&section=6" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The three main compounds that are used for producing terbufos are <a href="/wiki/Diethyl_dithiophosphoric_acid" title="Diethyl dithiophosphoric acid">diethyl-phosphorodithioic acid</a>, <a href="/wiki/Formaldehyde" title="Formaldehyde">formaldehyde</a> and <a href="/wiki/Tert-Butylthiol" title="Tert-Butylthiol">tert-butylthiol</a>. Formaldehyde acts as a carbon donor between the diethyl-phosphorodithioic acid and tert-butylthiol groups in order to link them.<sup id="cite_ref-:2_5-1" class="reference"><a href="#cite_note-:2-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> A secondary product of this reaction is water. </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Terbufos_synthesis.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/c/c1/Terbufos_synthesis.svg/421px-Terbufos_synthesis.svg.png" decoding="async" width="421" height="109" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/c/c1/Terbufos_synthesis.svg/632px-Terbufos_synthesis.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/c/c1/Terbufos_synthesis.svg/842px-Terbufos_synthesis.svg.png 2x" data-file-width="1184" data-file-height="306" /></a><figcaption>Synthesis of terbufos using diethylphosphorodithioate, formaldehyde and tert-butylthiol</figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Mechanism_of_action">Mechanism of action</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=7" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1236090951">.mw-parser-output .hatnote{font-style:italic}.mw-parser-output div.hatnote{padding-left:1.6em;margin-bottom:0.5em}.mw-parser-output .hatnote i{font-style:normal}.mw-parser-output .hatnote+link+.hatnote{margin-top:-0.5em}@media print{body.ns-0 .mw-parser-output .hatnote{display:none!important}}</style><div role="note" class="hatnote navigation-not-searchable">See also: <a href="/wiki/Organophosphate_poisoning" title="Organophosphate poisoning">Organophosphate poisoning</a></div> <p>Terbufos, like other organophosphates, inactivates the <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">acetylcholinesterase</a> in humans by phosphorylation of the hydroxyl group of serine present at the active site of the enzyme.<sup id="cite_ref-:0_20-0" class="reference"><a href="#cite_note-:0-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Metabolism">Metabolism</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=8" title="Edit section: Metabolism"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="Metabolism_in_animals">Metabolism in animals</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=9" title="Edit section: Metabolism in animals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The major excretion route of terbufos in lactating goats is via the urine. 96.0% and 86.9% of the administered compound was excreted through this route. Neither terbufos, nor a phosphorylated metabolite of the compound was found in milk, and no phosphorylated metabolite was detected in the tissues.<sup id="cite_ref-:1_4-1" class="reference"><a href="#cite_note-:1-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> A low concentration of terbufos was detected in the liver and the kidneys. Terbufos is extensively metabolised, judging from the low levels of terbufos and its metabolites detected in goat tissues. A proposed metabolism pathway of terbufos suggests a hydrolysis of the <a href="/w/index.php?title=Thiolophosphorus&action=edit&redlink=1" class="new" title="Thiolophosphorus (page does not exist)">thiolophosphorus</a> bond, an enzymatic S-methylation, desulfuration and sulfoxidation occurred in succession.<sup id="cite_ref-:1_4-2" class="reference"><a href="#cite_note-:1-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p><p>In rats, the proposed metabolism pathway includes more steps, while the metabolic product is the same as proposed in goats. The mechanism in rats includes extra steps in the metabolism of terbufos, and includes more metabolites.<sup id="cite_ref-:1_4-3" class="reference"><a href="#cite_note-:1-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <figure class="mw-halign-center" typeof="mw:File/Thumb"><a href="/wiki/File:Metabolism_of_terbufos_in_goats.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Metabolism_of_terbufos_in_goats.png/406px-Metabolism_of_terbufos_in_goats.png" decoding="async" width="406" height="458" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Metabolism_of_terbufos_in_goats.png/608px-Metabolism_of_terbufos_in_goats.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/9/9b/Metabolism_of_terbufos_in_goats.png/811px-Metabolism_of_terbufos_in_goats.png 2x" data-file-width="836" data-file-height="944" /></a><figcaption>The metabolism of terbufos in goats<sup id="cite_ref-:1_4-4" class="reference"><a href="#cite_note-:1-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading3"><h3 id="Biotransformation">Biotransformation</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=10" title="Edit section: Biotransformation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Terbufos is activated by a biotransformation to a <a href="/wiki/Sulfone" title="Sulfone">sulfone</a> compound. This conversion can take place in the (cellular) environment but also in exposed organisms using the <a href="/wiki/Cytochrome_P450" title="Cytochrome P450">cytochrome P450</a> action. This conversion process makes the molecule much more efficient in binding with <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">AChE</a>. The converted form may be significantly more toxic to amphibians than the parent compound. </p> <figure typeof="mw:File/Thumb"><a href="/wiki/File:The_biotransformation_steps_of_terbufos_into_sulfone.png" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/The_biotransformation_steps_of_terbufos_into_sulfone.png/124px-The_biotransformation_steps_of_terbufos_into_sulfone.png" decoding="async" width="124" height="405" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/0/06/The_biotransformation_steps_of_terbufos_into_sulfone.png/186px-The_biotransformation_steps_of_terbufos_into_sulfone.png 1.5x, //upload.wikimedia.org/wikipedia/commons/0/06/The_biotransformation_steps_of_terbufos_into_sulfone.png 2x" data-file-width="223" data-file-height="728" /></a><figcaption> The biotransformation steps of terbufos into sulfone<sup id="cite_ref-:1_4-5" class="reference"><a href="#cite_note-:1-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup></figcaption></figure> <div class="mw-heading mw-heading2"><h2 id="Toxicity">Toxicity</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=11" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading3"><h3 id="General_toxicity">General toxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=12" title="Edit section: General toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Terbufos can enter the body through dermal absorption (skin contact), inhalation or ingestion of the compound.<sup id="cite_ref-21" class="reference"><a href="#cite_note-21"><span class="cite-bracket">[</span>21<span class="cite-bracket">]</span></a></sup> Studies have suggested that the human NOEL ≥0.009 mg/m^3.<sup id="cite_ref-22" class="reference"><a href="#cite_note-22"><span class="cite-bracket">[</span>22<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Metabolite_toxicity">Metabolite toxicity</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=13" title="Edit section: Metabolite toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Two metabolites of terbufos have been tested for toxicity. Terbufos sulfoxide and terbufos sulfone both inhibited cholinesterase activity, but did not cause any mortalities in beagle dogs.<sup id="cite_ref-:1_4-6" class="reference"><a href="#cite_note-:1-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="Health_effects">Health effects</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=14" title="Edit section: Health effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <div class="mw-heading mw-heading4"><h4 id="Acute_effects">Acute effects</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=15" title="Edit section: Acute effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Terbufos can induce death by causing an <a href="/w/index.php?title=Acute_cholinergic_crisis&action=edit&redlink=1" class="new" title="Acute cholinergic crisis (page does not exist)">acute cholinergic crisis</a> (ACC). Due to the irreversible inhibition of the AChE enzyme by the compound, <a href="/wiki/Acetylcholine" title="Acetylcholine">acetylcholine</a> (ACh) can no longer be sufficiently broken down by the AChE. This results in excess ACh, which causes overstimulation of the <a href="/wiki/Neuromuscular_junction" title="Neuromuscular junction">neuromuscular junction</a>. The inhibiting effect of terbufos on AChE works on the peripheral muscarinic, nicotinic synapses and <a href="/wiki/Central_nervous_system" title="Central nervous system">central nervous system</a>. The onset of an ACC can vary from minutes to multiple hours post-exposure.<sup id="cite_ref-23" class="reference"><a href="#cite_note-23"><span class="cite-bracket">[</span>23<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-:0_20-1" class="reference"><a href="#cite_note-:0-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup> </p><p>Symptoms of a terbufos induced ACC result in muscarinic (<a href="/wiki/Perspiration" title="Perspiration">diaphoresis</a>, vomiting, miosis, salivation), nicotinic (<a href="/wiki/Pallor" title="Pallor">pallor</a> and muscle weakness with respiratory failure) and CNS poisoning (headache, dizziness, altered level of consciousness) symptoms.<sup id="cite_ref-24" class="reference"><a href="#cite_note-24"><span class="cite-bracket">[</span>24<span class="cite-bracket">]</span></a></sup> The toxic effects can be managed by early recognition of terbufos poisoning, rapid decontamination and treatment with <a href="/wiki/Atropine" title="Atropine">atropine</a> or <a href="/wiki/Oxime" title="Oxime">oxime</a> compounds.<sup id="cite_ref-:0_20-2" class="reference"><a href="#cite_note-:0-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-25" class="reference"><a href="#cite_note-25"><span class="cite-bracket">[</span>25<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading4"><h4 id="Long-term_effects">Long-term effects</h4><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=16" title="Edit section: Long-term effects"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Long term exposure effects which are specific for terbufos (effects generally associated with organophosphates (OPs) not included) are the development of lung cancer, leukemia and non-Hodgkin lymphoma (NHL) overall, as well as specific NHL subtypes. In males an increase in aggressive prostate cancer has also been observed, while in females a non-significant increase in breast cancer can be seen.<sup id="cite_ref-26" class="reference"><a href="#cite_note-26"><span class="cite-bracket">[</span>26<span class="cite-bracket">]</span></a></sup> </p><p>No genotoxic effects were detected in vitro and in vivo. No developmental abnormalities were noted in research, but a reduced fetal body weight was observed in mammals.<sup id="cite_ref-:1_4-7" class="reference"><a href="#cite_note-:1-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading3"><h3 id="2024_deaths_in_South_Africa">2024 deaths in South Africa</h3><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=17" title="Edit section: 2024 deaths in South Africa"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Terbufos was identified as the cause of the deaths of 22 <a href="/wiki/South_Africa" title="South Africa">South African</a> residents,<sup id="cite_ref-:4_27-0" class="reference"><a href="#cite_note-:4-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> including the highly publicised deaths of six children below the age of 10 from <a href="/wiki/Naledi_Local_Municipality,_Free_State" title="Naledi Local Municipality, Free State">Naledi</a>, <a href="/wiki/Soweto" title="Soweto">Soweto</a>.<sup id="cite_ref-:5_28-0" class="reference"><a href="#cite_note-:5-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> Though restricted for agricultural and not domestic usage in South Africa, terbufos and similar highly toxic substances are considered more effective than regulated options and can be found being sold by informal connivence stores, locally referred to as "<a href="/wiki/Spaza_shops" class="mw-redirect" title="Spaza shops">spaza shops</a>".<sup id="cite_ref-:5_28-1" class="reference"><a href="#cite_note-:5-28"><span class="cite-bracket">[</span>28<span class="cite-bracket">]</span></a></sup> As of January 2025, no link had been made between a specific shop and the deaths and the investigation had not determined whether the terbufos was locally produced or illegally imported.<sup id="cite_ref-:4_27-1" class="reference"><a href="#cite_note-:4-27"><span class="cite-bracket">[</span>27<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Detection">Detection</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=18" title="Edit section: Detection"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The amount of metabolites, caused by hydrolysis in vivo of an organophosphate compound such as terbufos, can be detected in the urine using gas chromatography and combined gas chromatography/mass spectrometry (GC-MC). Usually it is necessary to preserve the sample of the urine by addition of chloroform, to concentrate or extract the metabolites and to convert them to suitably-volatile derivatives. The detection can be useful to determine patterns of exposure. However, the levels of metabolite alone cannot be considered a guide to hazard.<sup id="cite_ref-29" class="reference"><a href="#cite_note-29"><span class="cite-bracket">[</span>29<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=Terbufos&action=edit&section=19" 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 mw-references-columns"><ol class="references"> <li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></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 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.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 class="citation web cs1"><a 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<i>www.kellysolutions.com</i>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.kellysolutions.com&rft.atitle=Material+safety+data+sheet-+Counter%C2%AE+15G+systemic+insecticide+nematicide&rft_id=http%3A%2F%2Fwww.kellysolutions.com%2Ferenewals%2Fdocumentsubmit%2FKellyData%2FVA%2Fpesticide%2FMSDS%2F7969%2F241-238%2F241-238_COUNTER_R__15G_SYSTEMIC_INSECTICIDE_NEMATICIDE_LOCKN_LOAD_R__CLOSED_LOADING_SYSTEM_11_28_2006_4_50_14_PM.pdf&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerbufos" class="Z3988"></span></span> </li> <li id="cite_note-:1-4"><span class="mw-cite-backlink">^ <a href="#cite_ref-:1_4-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:1_4-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-:1_4-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-:1_4-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-:1_4-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-:1_4-5"><sup><i><b>f</b></i></sup></a> <a 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href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFUnger" class="citation book cs1">Unger, T.A. <i>Pesticide Synthesis Handbook</i> (1st ed.). p. 368.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Abook&rft.genre=book&rft.btitle=Pesticide+Synthesis+Handbook&rft.pages=368&rft.edition=1st&rft.aulast=Unger&rft.aufirst=T.A.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerbufos" class="Z3988"></span></span> </li> <li id="cite_note-6"><span class="mw-cite-backlink"><b><a href="#cite_ref-6">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="http://www.villacrop.co.za/wp/wp-content/uploads/2016/12/Terbufos-15-GR-E_June2017_Villa.pdf">"TERBUFOS 15 GR"</a> <span class="cs1-format">(PDF)</span><span class="reference-accessdate">. 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"Review of Oximes in the Antidotal Treatment of Poisoning by Organophosphorus Nerve Agents". <i>Journal of Toxicology: Clinical Toxicology</i>. <b>40</b> (6): <span class="nowrap">803–</span>816. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1081%2FCLT-120015840">10.1081/CLT-120015840</a>. <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/12475193">12475193</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:20536869">20536869</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Journal+of+Toxicology%3A+Clinical+Toxicology&rft.atitle=Review+of+Oximes+in+the+Antidotal+Treatment+of+Poisoning+by+Organophosphorus+Nerve+Agents&rft.volume=40&rft.issue=6&rft.pages=%3Cspan+class%3D%22nowrap%22%3E803-%3C%2Fspan%3E816&rft.date=2002-11-26&rft_id=https%3A%2F%2Fapi.semanticscholar.org%2FCorpusID%3A20536869%23id-name%3DS2CID&rft_id=info%3Apmid%2F12475193&rft_id=info%3Adoi%2F10.1081%2FCLT-120015840&rft.aulast=Kassa&rft.aufirst=J.&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerbufos" class="Z3988"></span></span> </li> <li id="cite_note-26"><span class="mw-cite-backlink"><b><a href="#cite_ref-26">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFLerroKoutrosAndreottiFriesen2015" class="citation journal cs1">Lerro, Catherine C; Koutros, Stella; Andreotti, Gabriella; Friesen, Melissa C; Alavanja, Michael C; Blair, Aaron; Hoppin, Jane A; Sandler, Dale P; Lubin, Jay H; Ma, Xiaomei; Zhang, Yawei; Beane Freeman, Laura E (October 2015). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4909328">"Organophosphate insecticide use and cancer incidence among spouses of pesticide applicators in the Agricultural Health Study"</a>. <i>Occupational and Environmental Medicine</i>. <b>72</b> (10): <span class="nowrap">736–</span>744. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1136%2Foemed-2014-102798">10.1136/oemed-2014-102798</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/PMC4909328">4909328</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/26150671">26150671</a>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.jtitle=Occupational+and+Environmental+Medicine&rft.atitle=Organophosphate+insecticide+use+and+cancer+incidence+among+spouses+of+pesticide+applicators+in+the+Agricultural+Health+Study&rft.volume=72&rft.issue=10&rft.pages=%3Cspan+class%3D%22nowrap%22%3E736-%3C%2Fspan%3E744&rft.date=2015-10&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4909328%23id-name%3DPMC&rft_id=info%3Apmid%2F26150671&rft_id=info%3Adoi%2F10.1136%2Foemed-2014-102798&rft.aulast=Lerro&rft.aufirst=Catherine+C&rft.au=Koutros%2C+Stella&rft.au=Andreotti%2C+Gabriella&rft.au=Friesen%2C+Melissa+C&rft.au=Alavanja%2C+Michael+C&rft.au=Blair%2C+Aaron&rft.au=Hoppin%2C+Jane+A&rft.au=Sandler%2C+Dale+P&rft.au=Lubin%2C+Jay+H&rft.au=Ma%2C+Xiaomei&rft.au=Zhang%2C+Yawei&rft.au=Beane+Freeman%2C+Laura+E&rft_id=https%3A%2F%2Fwww.ncbi.nlm.nih.gov%2Fpmc%2Farticles%2FPMC4909328&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerbufos" class="Z3988"></span></span> </li> <li id="cite_note-:4-27"><span class="mw-cite-backlink">^ <a href="#cite_ref-:4_27-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:4_27-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.sanews.gov.za/south-africa/agriculture-conduct-inspections-terbufos-manufacturers">"Agriculture to conduct inspections of Terbufos manufacturers | SAnews"</a>. <i>www.sanews.gov.za</i>. 2024-11-21<span class="reference-accessdate">. Retrieved <span class="nowrap">2025-01-26</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.sanews.gov.za&rft.atitle=Agriculture+to+conduct+inspections+of+Terbufos+manufacturers+%7C+SAnews&rft.date=2024-11-21&rft_id=https%3A%2F%2Fwww.sanews.gov.za%2Fsouth-africa%2Fagriculture-conduct-inspections-terbufos-manufacturers&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerbufos" class="Z3988"></span></span> </li> <li id="cite_note-:5-28"><span class="mw-cite-backlink">^ <a href="#cite_ref-:5_28-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-:5_28-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite id="CITEREFMutsila2024" class="citation web cs1">Mutsila, Lerato (2024-10-28). <a rel="nofollow" class="external text" href="https://www.dailymaverick.co.za/article/2024-10-28-naledi-childrens-deaths-caused-by-restricted-pesticide-ministers/">"Naledi children's deaths caused by restricted pesticide: ministers"</a>. <i>Daily Maverick</i><span class="reference-accessdate">. Retrieved <span class="nowrap">2025-01-26</span></span>.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=Daily+Maverick&rft.atitle=Naledi+children%E2%80%99s+deaths+caused+by+restricted+pesticide%3A+ministers&rft.date=2024-10-28&rft.aulast=Mutsila&rft.aufirst=Lerato&rft_id=https%3A%2F%2Fwww.dailymaverick.co.za%2Farticle%2F2024-10-28-naledi-childrens-deaths-caused-by-restricted-pesticide-ministers%2F&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerbufos" class="Z3988"></span></span> </li> <li id="cite_note-29"><span class="mw-cite-backlink"><b><a href="#cite_ref-29">^</a></b></span> <span class="reference-text"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1238218222" /><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://www.inchem.org/pages/ehc.html">"Environ Health Criteria 63: Organophosphorus pesticides"</a>. <i>www.inchem.org</i>. 1986.</cite><span title="ctx_ver=Z39.88-2004&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=unknown&rft.jtitle=www.inchem.org&rft.atitle=Environ+Health+Criteria+63%3A+Organophosphorus+pesticides&rft.date=1986&rft_id=https%3A%2F%2Fwww.inchem.org%2Fpages%2Fehc.html&rfr_id=info%3Asid%2Fen.wikipedia.org%3ATerbufos" class="Z3988"></span></span> </li> </ol></div></div> <div class="mw-heading mw-heading2"><h2 id="External_links">External links</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Terbufos&action=edit&section=20" title="Edit section: External links"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <ul><li><i><a rel="nofollow" class="external text" href="http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/621.htm">Terbufos</a></i> in the Pesticide Properties DataBase (PPDB)</li></ul> <div class="navbox-styles"><style data-mw-deduplicate="TemplateStyles:r1129693374">.mw-parser-output .hlist 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title="Acetylcholine">Acetylcholine</a> <a href="/wiki/Metabolism" title="Metabolism">metabolism</a> and <a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">transport</a> <a href="/wiki/Receptor_modulator" title="Receptor modulator">modulators</a></div></th></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Enzyme" title="Enzyme">Enzyme</a><br /><small>(<a href="/wiki/Enzyme_modulator" title="Enzyme modulator">modulators</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Choline_acetyltransferase" title="Choline acetyltransferase"><abbr title="Choline acetyltransferase">ChAT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Choline acetyltransferase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <a href="/w/index.php?title=1-(-Benzoylethyl)pyridinium&action=edit&redlink=1" class="new" title="1-(-Benzoylethyl)pyridinium (page does not exist)">1-(-Benzoylethyl)pyridinium</a></li> <li><a href="/w/index.php?title=2-(%CE%B1-Naphthoyl)ethyltrimethylammonium&action=edit&redlink=1" class="new" title="2-(α-Naphthoyl)ethyltrimethylammonium (page does not exist)">2-(α-Naphthoyl)ethyltrimethylammonium</a></li> <li><a href="/w/index.php?title=3-Chloro-4-stillbazole&action=edit&redlink=1" class="new" title="3-Chloro-4-stillbazole (page does not exist)">3-Chloro-4-stillbazole</a></li> <li><a href="/w/index.php?title=4-(1-Naphthylvinyl)pyridine&action=edit&redlink=1" class="new" title="4-(1-Naphthylvinyl)pyridine (page does not exist)">4-(1-Naphthylvinyl)pyridine</a></li> <li><a href="/w/index.php?title=Acetylseco_hemicholinium-3&action=edit&redlink=1" class="new" title="Acetylseco hemicholinium-3 (page does not exist)">Acetylseco hemicholinium-3</a></li> <li><a href="/w/index.php?title=Acryloylcholine&action=edit&redlink=1" class="new" title="Acryloylcholine (page does not exist)">Acryloylcholine</a></li> <li><a href="/wiki/AF64A" class="mw-redirect" title="AF64A">AF64A</a></li> <li><a href="/w/index.php?title=(E)-1-Methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine&action=edit&redlink=1" class="new" title="(E)-1-Methyl-4-(1-naphthylvinyl)-1,2,3,6-tetrahydropyridine (page does not exist)">B115</a></li> <li><a href="/w/index.php?title=(2-Benzoylethyl)trimethylammonium&action=edit&redlink=1" class="new" title="(2-Benzoylethyl)trimethylammonium (page does not exist)">BETA</a></li> <li><a href="/w/index.php?title=N,N-Dimethylamino-2-ethoxyimino-2-adamantane&action=edit&redlink=1" class="new" title="N,N-Dimethylamino-2-ethoxyimino-2-adamantane (page does not exist)">CM-54,903</a></li> <li><a href="/w/index.php?title=N,N-Dimethylaminoethylacrylate&action=edit&redlink=1" class="new" title="N,N-Dimethylaminoethylacrylate (page does not exist)">N,N-Dimethylaminoethylacrylate</a></li> <li><a href="/w/index.php?title=N,N-Dimethylaminoethylchloroacetate&action=edit&redlink=1" class="new" title="N,N-Dimethylaminoethylchloroacetate (page does not exist)">N,N-Dimethylaminoethylchloroacetate</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase"><abbr title="Acetylcholinesterase">AChE</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Acetylcholinesterase</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Acetylcholinesterase_inhibitor" title="Acetylcholinesterase inhibitor">Inhibitors</a>:</b> <i>Reversible:</i> Carbamates: <a href="/wiki/Aldicarb" title="Aldicarb">Aldicarb</a></li> <li><a href="/wiki/Aminocarb" title="Aminocarb">Aminocarb</a></li> <li><a href="/wiki/Bendiocarb" title="Bendiocarb">Bendiocarb</a></li> <li><a href="/w/index.php?title=Bufencarb&action=edit&redlink=1" class="new" title="Bufencarb (page does not exist)">Bufencarb</a></li> <li><a href="/wiki/Carbaryl" title="Carbaryl">Carbaryl</a></li> <li><a href="/wiki/Carbendazim" title="Carbendazim">Carbendazim</a></li> <li><a href="/w/index.php?title=Carbetamide&action=edit&redlink=1" class="new" title="Carbetamide (page does not exist)">Carbetamide</a></li> <li><a href="/wiki/Carbofuran" title="Carbofuran">Carbofuran</a></li> <li><a href="/wiki/Carbosulfan" title="Carbosulfan">Carbosulfan</a></li> <li><a href="/w/index.php?title=Chlorbufam&action=edit&redlink=1" class="new" title="Chlorbufam (page does not exist)">Chlorbufam</a></li> <li><a href="/w/index.php?title=Chloropropham&action=edit&redlink=1" class="new" title="Chloropropham (page does not exist)">Chloropropham</a></li> <li><a href="/wiki/Dimetilan" title="Dimetilan">Dimetilan</a></li> <li><a href="/wiki/Ethienocarb" class="mw-redirect" title="Ethienocarb">Ethienocarb</a></li> <li><a href="/wiki/Ethiofencarb" title="Ethiofencarb">Ethiofencarb</a></li> <li><a href="/wiki/Fenobucarb" title="Fenobucarb">Fenobucarb</a></li> <li><a href="/wiki/Formetanate" title="Formetanate">Formetanate</a></li> <li><a href="/wiki/Formparanate" title="Formparanate">Formparanate</a></li> <li><a href="/wiki/Methiocarb" title="Methiocarb">Methiocarb</a></li> <li><a href="/wiki/Methomyl" title="Methomyl">Methomyl</a></li> <li><a href="/wiki/Metolcarb" title="Metolcarb">Metolcarb</a></li> <li><a href="/wiki/Miotine" title="Miotine">Miotine</a></li> <li><a href="/wiki/Oxamyl" title="Oxamyl">Oxamyl</a></li> <li><a href="/w/index.php?title=Phenmedipham&action=edit&redlink=1" class="new" title="Phenmedipham (page does not exist)">Phenmedipham</a></li> <li><a href="/w/index.php?title=Pinmicarb&action=edit&redlink=1" class="new" title="Pinmicarb (page does not exist)">Pinmicarb</a></li> <li><a href="/wiki/Pirimicarb" title="Pirimicarb">Pirimicarb</a></li> <li><a href="/wiki/Promecarb" title="Promecarb">Promecarb</a></li> <li><a href="/wiki/Propamocarb" title="Propamocarb">Propamocarb</a></li> <li><a href="/w/index.php?title=Propham&action=edit&redlink=1" class="new" title="Propham (page does not exist)">Propham</a></li> <li><a href="/wiki/Propoxur" title="Propoxur">Propoxur</a></li> <li><a href="/w/index.php?title=Thiodicarb&action=edit&redlink=1" class="new" title="Thiodicarb (page does not exist)">Thiodicarb</a></li> <li><a href="/wiki/Thiofanox" title="Thiofanox">Thiofanox</a>; Stigmines: <a href="/wiki/Distigmine" title="Distigmine">Distigmine</a></li> <li><a href="/w/index.php?title=Eptastigmine&action=edit&redlink=1" class="new" title="Eptastigmine (page does not exist)">Eptastigmine</a></li> <li><a href="/w/index.php?title=Ganstigmine&action=edit&redlink=1" class="new" title="Ganstigmine (page does not exist)">Ganstigmine</a></li> <li><a href="/wiki/Neostigmine" title="Neostigmine">Neostigmine</a> <a href="/wiki/Neostigmine/glycopyrronium_bromide" title="Neostigmine/glycopyrronium bromide">+glycopyrronium bromide</a></li> <li><a href="/wiki/Phenserine" title="Phenserine">Phenserine</a></li> <li><a href="/wiki/Physostigmine" title="Physostigmine">Physostigmine</a></li> <li><a href="/wiki/Pyridostigmine" title="Pyridostigmine">Pyridostigmine</a></li> <li><a href="/w/index.php?title=Quilostigmine&action=edit&redlink=1" class="new" title="Quilostigmine (page does not exist)">Quilostigmine</a></li> <li><a href="/wiki/Rivastigmine" title="Rivastigmine">Rivastigmine</a></li> <li><a href="/w/index.php?title=Terestigmine&action=edit&redlink=1" class="new" title="Terestigmine (page does not exist)">Terestigmine</a>; Others: <a href="/wiki/Acotiamide" title="Acotiamide">Acotiamide</a></li> <li><a href="/wiki/Ambenonium" class="mw-redirect" title="Ambenonium">Ambenonium</a></li> <li><a href="/wiki/Caffeine" title="Caffeine">Caffeine</a></li> <li><a href="/wiki/Donepezil" title="Donepezil">Donepezil</a></li> <li><a href="/wiki/EA-3990" title="EA-3990">EA-3990</a></li> <li><a href="/wiki/EA-4056" title="EA-4056">EA-4056</a></li> <li><a href="/wiki/Edrophonium" title="Edrophonium">Edrophonium</a></li> <li><a href="/wiki/Galantamine" title="Galantamine">Galantamine</a></li> <li><a href="/wiki/Huperzine_A" title="Huperzine A">Huperzine A</a></li> <li><a href="/w/index.php?title=Huprine_W&action=edit&redlink=1" class="new" title="Huprine W (page does not exist)">Huprine W</a></li> <li><a href="/wiki/Huprine_X" title="Huprine X">Huprine X</a></li> <li><a href="/w/index.php?title=Huprine_Y&action=edit&redlink=1" class="new" title="Huprine Y (page does not exist)">Huprine Y</a></li> <li><a href="/wiki/Ipidacrine" title="Ipidacrine">Ipidacrine</a></li> <li><a href="/wiki/Itopride" title="Itopride">Itopride</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Minaprine" title="Minaprine">Minaprine</a></li> <li><a href="/wiki/Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium_bromide)" title="Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)">Octamethylene-bis(5-dimethylcarbamoxyisoquinolinium bromide)</a></li> <li><a href="/wiki/T-1123" title="T-1123">T-1123</a></li> <li><a href="/wiki/T-1152" title="T-1152">T-1152</a></li> <li><a href="/wiki/T-1194" title="T-1194">T-1194</a></li> <li><a href="/wiki/TL-599" title="TL-599">TL-599</a></li> <li><a href="/wiki/TL-1238" title="TL-1238">TL-1238</a></li> <li><a href="/wiki/Tacrine" title="Tacrine">Tacrine</a></li> <li><a href="/w/index.php?title=Zanapezil&action=edit&redlink=1" class="new" title="Zanapezil (page does not exist)">Zanapezil</a></li></ul> <ul><li><i>Irreversible:</i> Organophosphates: <a href="/wiki/2-Ethoxycarbonyl-1-methylvinyl_cyclohexyl_methylphosphonate" title="2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate">2-Ethoxycarbonyl-1-methylvinyl cyclohexyl methylphosphonate</a></li> <li><a href="/wiki/Acephate" title="Acephate">Acephate</a></li> <li><a href="/wiki/Armine_(chemical)" title="Armine (chemical)">Armine</a></li> <li><a href="/wiki/Azinphos-ethyl" title="Azinphos-ethyl">Azinphos-ethyl</a></li> <li><a href="/wiki/Azinphos-methyl" title="Azinphos-methyl">Azinphos-methyl</a></li> <li><a href="/wiki/BAY-29952" title="BAY-29952">BAY-29952</a></li> <li><a href="/wiki/Bensulide" title="Bensulide">Bensulide</a></li> <li><a href="/wiki/Cadusafos" title="Cadusafos">Cadusafos</a></li> <li><a href="/wiki/Carbophenothion" title="Carbophenothion">Carbophenothion</a></li> <li><a href="/wiki/Chlorethoxyfos" title="Chlorethoxyfos">Chlorethoxyfos</a></li> <li><a href="/wiki/Chlorfenvinphos" title="Chlorfenvinphos">Chlorfenvinphos</a></li> <li><a href="/wiki/Chlorpyrifos" title="Chlorpyrifos">Chlorpyrifos</a></li> <li><a href="/wiki/Chlorpyrifos-methyl" class="mw-redirect" title="Chlorpyrifos-methyl">Chlorpyrifos-methyl</a></li> <li><a href="/wiki/Coumaphos" title="Coumaphos">Coumaphos</a></li> <li><a href="/wiki/Crotylsarin" title="Crotylsarin">Crotylsarin</a></li> <li><a href="/wiki/Cyanophos" title="Cyanophos">Cyanophos</a></li> <li><a href="/wiki/Cyclosarin" title="Cyclosarin">Cyclosarin (GF)</a></li> <li><a href="/wiki/Demephion" title="Demephion">Demephion</a></li> <li><a href="/wiki/Demeton" title="Demeton">Demeton</a></li> <li><a href="/wiki/Demeton-S-methyl" title="Demeton-S-methyl">Demeton-S-methyl</a></li> <li><a href="/wiki/Dialifor" title="Dialifor">Dialifor</a></li> <li><a href="/wiki/Diazinon" title="Diazinon">Diazinon</a></li> <li><a href="/wiki/Dichlorvos" title="Dichlorvos">Dichlorvos</a></li> <li><a href="/wiki/Dicrotophos" title="Dicrotophos">Dicrotophos</a></li> <li><a href="/wiki/Dicyclohexyl_phosphorofluoridate" title="Dicyclohexyl phosphorofluoridate">Dicyclohexyl phosphorofluoridate</a></li> <li><a href="/wiki/Diisopropylphosphate" title="Diisopropylphosphate">Diisopropylphosphate</a></li> <li><a href="/wiki/Diisopropyl_fluorophosphate" title="Diisopropyl fluorophosphate">Diisopropyl fluorophosphate</a></li> <li><a href="/wiki/Dimefox" title="Dimefox">Dimefox</a></li> <li><a href="/wiki/Dimethoate" title="Dimethoate">Dimethoate</a></li> <li><a href="/wiki/Dimethyl_4-(methylthio)phenyl_phosphate" title="Dimethyl 4-(methylthio)phenyl phosphate">Dimethyl 4-(methylthio)phenyl phosphate</a></li> <li><a href="/wiki/Dioxathion" title="Dioxathion">Dioxathion</a></li> <li><a href="/wiki/Disulfoton" title="Disulfoton">Disulfoton</a></li> <li><a href="/wiki/EA-2012" title="EA-2012">EA-2012</a></li> <li><a href="/wiki/EA-2054" title="EA-2054">EA-2054</a></li> <li><a href="/wiki/EA-2098" title="EA-2098">EA-2098</a></li> <li><a href="/wiki/EA-2192" title="EA-2192">EA-2192</a></li> <li><a href="/wiki/EA-2613" title="EA-2613">EA-2613</a></li> <li><a href="/wiki/EA-3148" title="EA-3148">EA-3148</a></li> <li><a href="/wiki/EA-4352" title="EA-4352">EA-4352</a></li> <li><a href="/wiki/Echothiophate" title="Echothiophate">Echothiophate</a></li> <li><a href="/wiki/Ethylsarin" title="Ethylsarin">Ethylsarin (GE)</a></li> <li><a href="/wiki/Endothion" title="Endothion">Endothion</a></li> <li><a href="/wiki/EPN_(insecticide)" title="EPN (insecticide)">EPN</a></li> <li><a href="/wiki/Ethion" title="Ethion">Ethion</a></li> <li><a href="/wiki/Ethoprop" class="mw-redirect" title="Ethoprop">Ethoprop</a></li> <li><a href="/wiki/Fenamiphos" title="Fenamiphos">Fenamiphos</a></li> <li><a href="/wiki/Fenitrothion" title="Fenitrothion">Fenitrothion</a></li> <li><a href="/wiki/Fenthion" title="Fenthion">Fenthion</a></li> <li><a href="/wiki/Fluorotabun" title="Fluorotabun">Fluorotabun</a></li> <li><a href="/wiki/Fonofos" title="Fonofos">Fonofos</a></li> <li><a href="/wiki/Formothion" title="Formothion">Formothion</a></li> <li><a href="/w/index.php?title=Fosthiazate&action=edit&redlink=1" class="new" title="Fosthiazate (page does not exist)">Fosthiazate</a></li> <li><a href="/wiki/GD-42" title="GD-42">GD-42</a></li> <li><a href="/wiki/GH_(nerve_agent)" title="GH (nerve agent)">GH</a></li> <li><a href="/w/index.php?title=GT-45&action=edit&redlink=1" class="new" title="GT-45 (page does not exist)">GT-45</a></li> <li><a href="/wiki/GV_(nerve_agent)" title="GV (nerve agent)">GV</a></li> <li><a href="/wiki/Guanitoxin" title="Guanitoxin">Guanitoxin</a></li> <li><a href="/wiki/Hexaethyl_tetraphosphate" title="Hexaethyl tetraphosphate">Hexaethyl tetraphosphate (HETP)</a></li> <li><a href="/wiki/Isofluorophate" class="mw-redirect" title="Isofluorophate">Isofluorophate</a></li> <li><a href="/wiki/Isoxathion" title="Isoxathion">Isoxathion</a></li> <li><a href="/wiki/Leptophos" title="Leptophos">Leptophos</a></li> <li><a href="/wiki/Malaoxon" title="Malaoxon">Malaoxon</a></li> <li><a href="/wiki/Malathion" title="Malathion">Malathion</a></li> <li><a href="/w/index.php?title=Mazidox&action=edit&redlink=1" class="new" title="Mazidox (page does not exist)">Mazidox</a></li> <li><a href="/wiki/Methamidophos" title="Methamidophos">Methamidophos</a></li> <li><a href="/wiki/Methidathion" title="Methidathion">Methidathion</a></li> <li><a href="/wiki/Methyl_phenkapton" title="Methyl phenkapton">Methyl phenkapton</a></li> <li><a href="/wiki/Methylfluorophosphonylcholine" title="Methylfluorophosphonylcholine">Methylfluorophosphonylcholine (MFPCh)</a></li> <li><a href="/wiki/Metrifonate" title="Metrifonate">Metrifonate</a></li> <li><a href="/wiki/Mevinphos" title="Mevinphos">Mevinphos</a></li> <li><a href="/wiki/Mipafox" title="Mipafox">Mipafox</a></li> <li><a href="/wiki/Monocrotophos" title="Monocrotophos">Monocrotophos</a></li> <li><a href="/wiki/MSPI_(nerve_agent)" title="MSPI (nerve agent)">MSPI</a></li> <li><a href="/wiki/Naled" title="Naled">Naled</a></li> <li><a href="/wiki/Novichok_agent" class="mw-redirect" title="Novichok agent">Novichok agent</a></li> <li><a href="/wiki/Omethoate" title="Omethoate">Omethoate</a></li> <li><a href="/wiki/Oxydemeton-methyl" title="Oxydemeton-methyl">Oxydemeton-methyl</a></li> <li><a href="/wiki/Paraoxon" title="Paraoxon">Paraoxon</a></li> <li><a href="/wiki/Parathion" title="Parathion">Parathion</a></li> <li><a href="/wiki/Parathion-methyl" class="mw-redirect" title="Parathion-methyl">Parathion-methyl</a></li> <li><a href="/wiki/Phorate" title="Phorate">Phorate</a></li> <li><a href="/wiki/Phosalone" title="Phosalone">Phosalone</a></li> <li><a href="/wiki/Phosfolan" title="Phosfolan">Phosfolan</a></li> <li><a href="/wiki/Phosmet" title="Phosmet">Phosmet</a></li> <li><a href="/wiki/Phosphamidon" title="Phosphamidon">Phosphamidon</a></li> <li><a href="/wiki/Phoxim" title="Phoxim">Phoxim</a></li> <li><a href="/wiki/Pirimiphos-methyl" title="Pirimiphos-methyl">Pirimiphos-methyl</a></li> <li><a href="/wiki/Profenofos" title="Profenofos">Profenofos</a></li> <li><a href="/wiki/Prothoate" title="Prothoate">Prothoate</a></li> <li><a href="/wiki/R-16661" title="R-16661">R-16661</a></li> <li><a href="/w/index.php?title=Ro_3-0340&action=edit&redlink=1" class="new" title="Ro 3-0340 (page does not exist)">Ro 3-0340</a></li> <li><a href="/w/index.php?title=Ro_3-0346&action=edit&redlink=1" class="new" title="Ro 3-0346 (page does not exist)">Ro 3-0346</a></li> <li><a href="/w/index.php?title=Ro_3-0347&action=edit&redlink=1" class="new" title="Ro 3-0347 (page does not exist)">Ro 3-0347</a></li> <li><a href="/w/index.php?title=Ro_3-0351&action=edit&redlink=1" class="new" title="Ro 3-0351 (page does not exist)">Ro 3-0351</a></li> <li><a href="/w/index.php?title=Ro_3-0352&action=edit&redlink=1" class="new" title="Ro 3-0352 (page does not exist)">Ro 3-0352</a></li> <li><a href="/w/index.php?title=Ro_3-0397&action=edit&redlink=1" class="new" title="Ro 3-0397 (page does not exist)">Ro 3-0397</a></li> <li><a href="/w/index.php?title=Ro_3-0411&action=edit&redlink=1" class="new" title="Ro 3-0411 (page does not exist)">Ro 3-0411</a></li> <li><a href="/wiki/Ro_3-0412" title="Ro 3-0412">Ro 3-0412</a></li> <li><a href="/w/index.php?title=Ro_3-0417&action=edit&redlink=1" class="new" title="Ro 3-0417 (page does not exist)">Ro 3-0417</a></li> <li><a href="/wiki/Ro_3-0419" title="Ro 3-0419">Ro 3-0419</a></li> <li><a href="/wiki/Ro_3-0422" title="Ro 3-0422">Ro 3-0422</a></li> <li><a href="/w/index.php?title=Ro_3-0433&action=edit&redlink=1" class="new" title="Ro 3-0433 (page does not exist)">Ro 3-0433</a></li> <li><a href="/w/index.php?title=Ronnel&action=edit&redlink=1" class="new" title="Ronnel (page does not exist)">Ronnel</a></li> <li><a href="/wiki/Sarin" title="Sarin">Sarin (GB)</a></li> <li><a href="/wiki/Schradan" title="Schradan">Schradan</a></li> <li><a href="/wiki/Soman" title="Soman">Soman (GD)</a></li> <li><a href="/wiki/Sulfotep" title="Sulfotep">Sulfotep (TEDP)</a></li> <li><a href="/wiki/Tabun_(nerve_agent)" title="Tabun (nerve agent)">Tabun (GA)</a></li> <li><a href="/wiki/Tebupirimfos" title="Tebupirimfos">Tebupirimfos</a></li> <li><a href="/wiki/Temefos" title="Temefos">Temefos</a></li> <li><a class="mw-selflink selflink">Terbufos</a></li> <li><a href="/wiki/Tetrachlorvinphos" title="Tetrachlorvinphos">Tetrachlorvinphos</a></li> <li><a href="/wiki/Tetraethyl_pyrophosphate" title="Tetraethyl pyrophosphate">Tetraethyl pyrophosphate (TEPP)</a></li> <li><a href="/wiki/Triazofos" title="Triazofos">Triazofos</a></li> <li><a href="/w/index.php?title=Tribufos&action=edit&redlink=1" class="new" title="Tribufos (page does not exist)">Tribufos</a></li> <li><a href="/wiki/Trichlorfon" class="mw-redirect" title="Trichlorfon">Trichlorfon</a></li> <li><a href="/wiki/Trichloronate" title="Trichloronate">Trichloronate</a></li> <li><a href="/wiki/Tricresyl_phosphate" title="Tricresyl phosphate">Tricresyl phosphate</a></li> <li><a href="/wiki/VE_(nerve_agent)" title="VE (nerve agent)">VE</a></li> <li><a href="/wiki/VG_(nerve_agent)" title="VG (nerve agent)">VG</a></li> <li><a href="/wiki/VM_(nerve_agent)" title="VM (nerve agent)">VM</a></li> <li><a href="/wiki/VP_(nerve_agent)" class="mw-redirect" title="VP (nerve agent)">VP</a></li> <li><a href="/wiki/VS_(nerve_agent)" title="VS (nerve agent)">VS</a></li> <li><a href="/wiki/VR_(nerve_agent)" title="VR (nerve agent)">VR</a></li> <li><a href="/wiki/VX_(nerve_agent)" title="VX (nerve agent)">VX</a>; Others: <a href="/wiki/Demecarium" class="mw-redirect" title="Demecarium">Demecarium</a></li> <li><a href="/wiki/Fasciculin" title="Fasciculin">Fasciculins (green mamba toxins)</a> (<a href="/w/index.php?title=Fasciculin_1&action=edit&redlink=1" class="new" title="Fasciculin 1 (page does not exist)">1</a>, <a href="/w/index.php?title=Fasciculin_2&action=edit&redlink=1" class="new" title="Fasciculin 2 (page does not exist)">2</a>, <a href="/w/index.php?title=Fasciculin_3&action=edit&redlink=1" class="new" title="Fasciculin 3 (page does not exist)">3</a>, <a href="/w/index.php?title=Fasciculin_4&action=edit&redlink=1" class="new" title="Fasciculin 4 (page does not exist)">4</a>)</li> <li><a href="/wiki/Onchidal" title="Onchidal">Onchidal</a> (<i><a href="/wiki/Onchidella_binneyi" title="Onchidella binneyi">Onchidella binneyi</a></i>)</li> <li><a href="/wiki/Methanesulfonyl_fluoride" title="Methanesulfonyl fluoride">Methanesulfonyl fluoride</a></li></ul> <ul><li><i>Unsorted:</i> <a href="/wiki/%CE%91-Pinene" title="Α-Pinene">α-Pinene</a></li> <li><a href="/wiki/%CE%91-Viniferin" title="Α-Viniferin">α-Viniferin</a></li> <li><a href="/wiki/Affinine" title="Affinine">Affinine</a></li> <li><a href="/wiki/Affinisine" title="Affinisine">Affinisine</a></li> <li><a href="/wiki/Arisugacin_A" title="Arisugacin A">Arisugacin A</a></li> <li><a href="/wiki/Bulbocapnine" title="Bulbocapnine">Bulbocapnine</a></li> <li><a href="/wiki/Conodurine" title="Conodurine">Conodurine</a></li> <li><a href="/wiki/Coronaridine" title="Coronaridine">Coronaridine</a></li> <li><a href="/wiki/Corydaline" title="Corydaline">Corydaline</a></li> <li><a href="/wiki/Corynoline" title="Corynoline">Corynoline</a></li> <li><a href="/wiki/Crimidine" title="Crimidine">Crimidine</a></li> <li><a href="/wiki/Cyclanoline" title="Cyclanoline">Cyclanoline</a></li> <li><a href="/wiki/Cymserine" title="Cymserine">Cymserine</a></li> <li><a href="/wiki/Harmaline" title="Harmaline">Harmaline</a></li> <li><a href="/wiki/Kobophenol_A" title="Kobophenol A">Kobophenol A</a></li> <li><a href="/wiki/Lactucopicrin" title="Lactucopicrin">Lactucopicrin</a></li> <li><a href="/wiki/Lycorine" title="Lycorine">Lycorine</a></li> <li><a href="/wiki/Phosacetim" title="Phosacetim">Phosacetim</a></li> <li><a href="/wiki/Rosmarinic_acid" title="Rosmarinic acid">Rosmarinic acid</a></li> <li><a href="/wiki/Stercuronium_iodide" title="Stercuronium iodide">Stercuronium iodide</a></li> <li><a href="/wiki/Taspine" title="Taspine">Taspine</a></li> <li><a href="/wiki/Tetrahydrocannabinol" title="Tetrahydrocannabinol">Tetrahydrocannabinol</a></li> <li><a href="/wiki/Ungeremine" title="Ungeremine">Ungeremine</a></li> <li><a href="/wiki/Ungiminorine" title="Ungiminorine">Ungiminorine</a></li> <li><a href="/wiki/Dimethylcarbamoyl_fluoride" title="Dimethylcarbamoyl fluoride">Dimethylcarbamoyl fluoride</a></li> <li><a href="/wiki/BW284C51" title="BW284C51">BW284C51</a></li> <li><a href="/wiki/TMTFA" title="TMTFA">TMTFA</a></li> <li><a href="/wiki/3152_CT" title="3152 CT">3152 CT</a></li></ul> <ul><li><a href="/wiki/Cholinesterase_reactivator" title="Cholinesterase reactivator">Reactivators</a>: <a href="/wiki/Asoxime_chloride" title="Asoxime chloride">Asoxime chloride</a></li> <li><a href="/w/index.php?title=Methoxime&action=edit&redlink=1" class="new" title="Methoxime (page does not exist)">Methoxime</a></li> <li><a href="/wiki/Obidoxime" title="Obidoxime">Obidoxime</a></li> <li><a href="/wiki/Pralidoxime" title="Pralidoxime">Pralidoxime</a></li> <li><a href="/wiki/Trimedoxime_bromide" title="Trimedoxime bromide">Trimedoxime bromide</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Butyrylcholinesterase" title="Butyrylcholinesterase"><abbr title="Butyrylcholinesterase">BChE</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Butyrylcholinesterase</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <a href="/wiki/Affinine" title="Affinine">Affinine</a></li> <li><a href="/wiki/Affinisine" title="Affinisine">Affinisine</a></li> <li><a href="/wiki/Conodurine" title="Conodurine">Conodurine</a></li> <li><a href="/wiki/Cymserine" title="Cymserine">Cymserine</a></li> <li><a href="/wiki/Ladostigil" title="Ladostigil">Ladostigil</a></li> <li><a href="/wiki/Profenamine" title="Profenamine">Profenamine (ethopropazine)</a></li> <li><a href="/wiki/Rivastigmine" title="Rivastigmine">Rivastigmine</a></li> <li><a href="/wiki/Tacrine" title="Tacrine">Tacrine</a></li> <li><a href="/w/index.php?title=ZINC-12613047&action=edit&redlink=1" class="new" title="ZINC-12613047 (page does not exist)">ZINC-12613047</a></li> <li>Many of the other AChE inhibitors listed above</li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_transporter" title="Neurotransmitter transporter">Transporter</a><br /><small>(<a href="/wiki/Transporter_modulator" class="mw-redirect" title="Transporter modulator">modulators</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Choline_transporter" title="Choline transporter"><abbr title="Choline transporter">CHT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Choline transporter</span></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <a href="/wiki/Hemicholinium-3" title="Hemicholinium-3">Hemicholinium-3 (hemicholine)</a></li> <li><a href="/wiki/Triethylcholine" title="Triethylcholine">Triethylcholine</a></li></ul> <ul><li><b>Enhancers:</b> <a href="/wiki/Coluracetam" title="Coluracetam">Coluracetam</a></li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Vesicular_acetylcholine_transporter" title="Vesicular acetylcholine transporter"><abbr title="Vesicular acetylcholine transporter">VAChT</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Vesicular acetylcholine transporter</span></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b>Inhibitors:</b> <a href="/wiki/Vesamicol" title="Vesamicol">Vesamicol</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><th scope="row" class="navbox-group" style="width:1%;text-align:center;"><a href="/wiki/Neurotransmitter_release" class="mw-redirect" title="Neurotransmitter release">Release</a><br /><small>(<a href="/wiki/Release_modulator" title="Release modulator">modulators</a>)</small></th><td class="navbox-list-with-group navbox-list navbox-odd" style="width:100%;padding:0"><div style="padding:0 0.25em"></div><table class="nowraplinks navbox-subgroup" style="border-spacing:0"><tbody><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Release_inhibitor" class="mw-redirect" title="Release inhibitor">Inhibitors</a></th><td class="navbox-list-with-group navbox-list navbox-even" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Synaptosomal-associated_protein_25" class="mw-redirect" title="Synaptosomal-associated protein 25"><abbr title="Synaptosomal-associated protein 25">SNAP-25</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Synaptosomal-associated protein 25</span> inactivators:</b> <a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a> (<a href="/wiki/Botulinum_toxin_A" class="mw-redirect" title="Botulinum toxin A">A</a>, <a href="/wiki/Botulinum_toxin_C" class="mw-redirect" title="Botulinum toxin C">C</a>, <a href="/wiki/Botulinum_toxin_E" class="mw-redirect" title="Botulinum toxin E">E</a>)</li></ul> <ul><li><b><a href="/wiki/Vesicle-associated_membrane_protein" title="Vesicle-associated membrane protein"><abbr title="Vesicle-associated membrane protein">VAMP</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Vesicle-associated membrane protein</span> inactivators:</b> <a href="/wiki/Botulinum_toxin" title="Botulinum toxin">Botulinum toxin</a> (<a href="/wiki/Botulinum_toxin_B" class="mw-redirect" title="Botulinum toxin B">B</a>, <a href="/wiki/Botulinum_toxin_D" class="mw-redirect" title="Botulinum toxin D">D</a>, <a href="/wiki/Botulinum_toxin_F" class="mw-redirect" title="Botulinum toxin F">F</a>, <a href="/wiki/Botulinum_toxin_G" class="mw-redirect" title="Botulinum toxin G">G</a>)</li></ul> <ul><li><b>Others:</b> <a href="/wiki/Bungarotoxin" title="Bungarotoxin">Bungarotoxins</a> (<a href="/wiki/Beta-Bungarotoxin" class="mw-redirect" title="Beta-Bungarotoxin">β-bungarotoxin</a>, <a href="/wiki/%CE%93-bungarotoxin" class="mw-redirect" title="Γ-bungarotoxin">γ-bungarotoxin</a>)</li></ul> </div></td></tr><tr><th scope="row" class="navbox-group" style="width:6em;;text-align:center;"><a href="/wiki/Release_enhancer" class="mw-redirect" title="Release enhancer">Enhancers</a></th><td class="navbox-list-with-group navbox-list navbox-odd" style="padding:0"><div style="padding:0 0.25em"> <ul><li><b><a href="/wiki/Latrophilin" title="Latrophilin"><abbr title="Latrophilin">LPHN</abbr></a><span class="sr-only" style="border: 0; clip: rect(0, 0, 0, 0); clip-path: polygon(0px 0px, 0px 0px, 0px 0px); height: 1px; margin: -1px; overflow: hidden; padding: 0; position: absolute; width: 1px; white-space: nowrap;">Tooltip Latrophilin</span> agonists:</b> <a href="/wiki/Alpha-Latrotoxin" class="mw-redirect" title="Alpha-Latrotoxin">α-Latrotoxin</a></li></ul> <ul><li><b>Others:</b> Atracotoxins (e.g., <a href="/wiki/Robustoxin" class="mw-redirect" title="Robustoxin">robustoxin</a>, <a href="/wiki/Versutoxin" title="Versutoxin">versutoxin</a>)</li> <li><a href="/wiki/Crotoxin" title="Crotoxin">Crotoxin</a></li></ul> </div></td></tr></tbody></table><div></div></td></tr><tr><td class="navbox-abovebelow" colspan="2"><div> <dl><dt>See also</dt> <dd><a href="/wiki/Template:Receptor_modulators" title="Template:Receptor modulators">Receptor/signaling modulators</a></dd> <dd><a href="/wiki/Template:Muscarinic_acetylcholine_receptor_modulators" title="Template:Muscarinic acetylcholine receptor modulators">Muscarinic acetylcholine receptor modulators</a></dd> <dd><a href="/wiki/Template:Nicotinic_acetylcholine_receptor_modulators" title="Template:Nicotinic acetylcholine receptor modulators">Nicotinic acetylcholine receptor modulators</a></dd></dl> </div></td></tr></tbody></table></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 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