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href="#Metabolism_and_biotransformation"> <div class="vector-toc-text"> <span class="vector-toc-numb">5</span> <span>Metabolism and biotransformation</span> </div> </a> <ul id="toc-Metabolism_and_biotransformation-sublist" class="vector-toc-list"> </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">6</span> <span>Toxicity</span> </div> </a> <ul id="toc-Toxicity-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Effects_on_animals" class="vector-toc-list-item vector-toc-level-1 vector-toc-list-item-expanded"> <a class="vector-toc-link" href="#Effects_on_animals"> <div class="vector-toc-text"> <span class="vector-toc-numb">7</span> <span>Effects on animals</span> </div> </a> <ul id="toc-Effects_on_animals-sublist" class="vector-toc-list"> </ul> </li> <li id="toc-Efficacy" class="vector-toc-list-item vector-toc-level-1 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class="noprint">From Wikipedia, the free encyclopedia</div> </div> <div id="contentSub"><div id="mw-content-subtitle"></div></div> <div id="mw-content-text" class="mw-body-content"><div class="mw-content-ltr mw-parser-output" lang="en" dir="ltr"><div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Thiosulfate insecticide against nematodes</div> <div class="shortdescription nomobile noexcerpt noprint searchaux" style="display:none">Pharmaceutical compound</div> <style data-mw-deduplicate="TemplateStyles:r1269284339">@media screen{html.skin-theme-clientpref-night .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .dark_mode_safe img{background-color:var(--background-color-inverted,#f8f9fa)}}</style> <style data-mw-deduplicate="TemplateStyles:r1257001546">.mw-parser-output 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.mw-parser-output .infobox-table th,body.skin--responsive .mw-parser-output .infobox-table td{padding-left:inherit;padding-right:inherit}}</style><table class="infobox" style="border-spacing:2px;"><caption class="infobox-title"><span title="International nonproprietary name (INN): Cadusafos">Cadusafos</span></caption><tbody><tr><td colspan="2" class="infobox-image"><span class="mw-default-size dark_mode_safe" typeof="mw:File/Frameless"><a href="/wiki/File:Cadusafos_structure.svg" class="mw-file-description"><img src="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Cadusafos_structure.svg/220px-Cadusafos_structure.svg.png" decoding="async" width="220" height="175" class="mw-file-element" srcset="//upload.wikimedia.org/wikipedia/commons/thumb/1/12/Cadusafos_structure.svg/330px-Cadusafos_structure.svg.png 1.5x, //upload.wikimedia.org/wikipedia/commons/thumb/1/12/Cadusafos_structure.svg/440px-Cadusafos_structure.svg.png 2x" data-file-width="460" data-file-height="365" /></a></span></td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Clinical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_nomenclature#Trade_names" title="Drug nomenclature">Trade names</a></th><td class="infobox-data">Cadusafos</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Legal status</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Regulation_of_therapeutic_goods" title="Regulation of therapeutic goods">Legal status</a></th><td class="infobox-data"><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><small><abbr class="country-name" title="United States">US</abbr>:</small> eligible for reregistration</li> <li><small><abbr class="country-name" title="European Union">EU</abbr>:</small> not approved</li></ul></div> </td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;"><a href="/wiki/Pharmacokinetics" title="Pharmacokinetics">Pharmacokinetic</a> data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Bioavailability" title="Bioavailability">Bioavailability</a></th><td class="infobox-data">90-100%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Drug_metabolism" title="Drug metabolism">Metabolism</a></th><td class="infobox-data">>90%</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Metabolite" title="Metabolite">Metabolites</a></th><td class="infobox-data">hydroxy sulfones, phosphorothioic and sulfonic acids</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Biological_half-life" title="Biological half-life">Elimination <span class="nowrap">half-life</span></a></th><td class="infobox-data">not available</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Excretion" title="Excretion">Excretion</a></th><td class="infobox-data">kidney, renal</td></tr><tr><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Identifiers</th></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><div><a href="/wiki/IUPAC_nomenclature_of_chemistry" title="IUPAC nomenclature of chemistry">IUPAC name</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; text-align:left; padding-left:1.5em; text-indent:-1.5em;"><li style="line-height: inherit; margin: 0"><div style="font-size: 97%;"><i>S</i>,<i>S</i>-di-<i>sec</i>-butyl <i>O</i>-ethyl phosphorodithioate</div></li></ul> </div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=95465-99-9">95465-99-9</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/PubChem#CID" title="PubChem">PubChem</a> <span style="font-weight:normal"><abbr title="Compound ID">CID</abbr></span></th><td class="infobox-data"><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/91752">91752</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChemSpider" title="ChemSpider">ChemSpider</a></th><td class="infobox-data"><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.82850.html">82850</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Unique_Ingredient_Identifier" title="Unique Ingredient Identifier">UNII</a></th><td class="infobox-data"><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/8JBJ4VO75K">8JBJ4VO75K</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/KEGG" title="KEGG">KEGG</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.kegg.jp"><a rel="nofollow" class="external text" href="https://www.kegg.jp/entry/C18395">C18395</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEBI" title="ChEBI">ChEBI</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:38588">CHEBI:38588</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ChEMBL" title="ChEMBL">ChEMBL</a></th><td class="infobox-data"><link rel="mw-deduplicated-inline-style" href="mw-data:TemplateStyles:r1126788409" /><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL2228571">ChEMBL2228571</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><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></th><td class="infobox-data"><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/DTXSID7037505">DTXSID7037505</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q421582#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><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a></th><td class="infobox-data"><a rel="nofollow" class="external text" href="https://echa.europa.eu/substance-information/-/substanceinfo/100.108.705">100.108.705</a> <span class="mw-valign-text-top noprint" typeof="mw:File/Frameless"><a href="https://www.wikidata.org/wiki/Q421582#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><th colspan="2" class="infobox-header" style="background:#ddd;color:inherit;">Chemical and physical data</th></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Chemical_formula" title="Chemical formula">Formula</a></th><td class="infobox-data"><span title="Carbon">C</span><sub>10</sub><span title="Hydrogen">H</span><sub>23</sub><span title="Oxygen">O</span><sub>2</sub><span title="Phosphorus">P</span><span title="Sulfur">S</span><sub>2</sub></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Molar_mass" title="Molar mass">Molar mass</a></th><td class="infobox-data"><span class="nowrap"><span data-sort-value="7002270390000000000♠"></span>270.39</span> g·mol<sup>−1</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;">3D model (<a href="/wiki/JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</th><td class="infobox-data"><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=CCC%28C%29SP%28%3DO%29%28OCC%29SC%28C%29CC">Interactive image</a></span></li></ul></div></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Density" title="Density">Density</a></th><td class="infobox-data">1.054 g/cm<sup>3</sup></td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Boiling_point" title="Boiling point">Boiling point</a></th><td class="infobox-data">112–114 °C (234–237 °F)</td></tr><tr><th scope="row" class="infobox-label" style="line-height:1.2em;"><a href="/wiki/Aqueous_solution" title="Aqueous solution">Solubility in water</a></th><td class="infobox-data">0.248 g/L</td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><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="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">CCC(C)SP(=O)(OCC)SC(C)CC</div></li></ul> </div></td></tr><tr><td colspan="2" class="infobox-full-data"><div class="collapsible-list mw-collapsible mw-collapsed" style="text-align: left;"> <div style="line-height: 1.6em; font-weight: bold;"><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="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">InChI=1S/C10H23O2PS2/c1-6-9(4)14-13(11,12-8-3)15-10(5)7-2/h9-10H,6-8H2,1-5H3</div></li><li style="line-height: inherit; margin: 0"><div style="word-wrap:break-word; text-indent:-1.5em; text-align:left; padding-left:1.5em; font-size:97%; line-height:120%;">Key:KXRPCFINVWWFHQ-UHFFFAOYSA-N</div></li></ul> </div></td></tr></tbody></table> <p><b>Cadusafos</b> (<b>2-[butan-2-ylsulfanyl(ethoxy)phosphoryl]sulfanylbutane</b>) is a chemical <a href="/wiki/Insecticide" title="Insecticide">insecticide</a> and <a href="/wiki/Nematicide" title="Nematicide">nematicide</a> often used against <a href="/wiki/Parasitic" class="mw-redirect" title="Parasitic">parasitic</a> nematode populations. The compound acts as a <a href="/wiki/Acetylcholinesterase_inhibitor" title="Acetylcholinesterase inhibitor">acetylcholinesterase inhibitor</a>. It belongs the chemical class of synthetic organic <a href="/wiki/Thiophosphate" title="Thiophosphate">thiophosphates</a> and it is a volatile and persistent clear liquid. It is used on food crops such as tomatoes, bananas and chickpeas. It is currently not approved by the <a href="/wiki/European_Commission" title="European Commission">European Commission</a> for use in the EU. Exposure can occur through <a href="/wiki/Inhalation" title="Inhalation">inhalation</a>, <a href="/wiki/Ingestion" title="Ingestion">ingestion</a> or contact with the skin. The compound is highly toxic to <a href="/wiki/Nematodes" class="mw-redirect" title="Nematodes">nematodes</a>, <a href="/wiki/Earthworms" class="mw-redirect" title="Earthworms">earthworms</a> and birds but poses no <a href="/wiki/Carcinogenic" class="mw-redirect" title="Carcinogenic">carcinogenic</a> risk to humans.<sup id="cite_ref-pubchem_1-0" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-Donovan_2-0" class="reference"><a href="#cite_note-Donovan-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-database_3-0" class="reference"><a href="#cite_note-database-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-meher2_4-0" class="reference"><a href="#cite_note-meher2-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-anwar_5-0" class="reference"><a href="#cite_note-anwar-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup><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> </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=Cadusafos&action=edit&section=1" title="Edit section: History"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A <a href="/wiki/Patent_application" title="Patent application">patent application</a> for Cadusafos was first filed in Europe on August 13, 1982 by <a href="/wiki/FMC_Corporation" title="FMC Corporation">FMC Corporation</a>, an American chemical company which originated as an insecticide producer. In their patent application, they claimed that the compound should preferably be used to “control nematodes and soil insects, but may also control some insects which feed on the above ground portions of the plant.”<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> The patent is expired, meaning that the compound is commercially available from chemical vendors such as <a href="/wiki/Sigma_Aldrich" class="mw-redirect" title="Sigma Aldrich">Sigma Aldrich</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> However, the pesticide is not approved for use in Europe due to the lack of information on consumer exposure and the risk to groundwater.<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> </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=Cadusafos&action=edit&section=2" title="Edit section: Structure and reactivity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cadusafos is a <a href="/wiki/Organic_synthesis" title="Organic synthesis">synthetic organic</a> <a href="/wiki/Thiophosphate" title="Thiophosphate">thiophosphate</a> compound which is observed as a <a href="/wiki/Volatility_(chemistry)" title="Volatility (chemistry)">volatile</a> and persistent clear liquid. The toxin is an <a href="/wiki/Organothiophosphate" title="Organothiophosphate">organothiophosphate</a> <a href="/wiki/Insecticide" title="Insecticide">insecticide</a>.<sup id="cite_ref-pubchem_1-1" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> Organothiophosphorus compounds are identified as compounds which contain carbonphosphorus bonds where the <a href="/wiki/Phosphorus" title="Phosphorus">phosphorus</a> atom is also bound to <a href="/wiki/Sulphur" class="mw-redirect" title="Sulphur">sulphur</a>. Many of these compounds serve as insecticides and <a href="/wiki/Cholinergic_agents" class="mw-redirect" title="Cholinergic agents">cholinergic agents</a>.<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> Cadusafos contains the phosphorus atom bound to two sulphurs which are attached to iso-butyl substituents. The phosphorus is also connected to oxygen by a double bond and is bound to an ethyl <a href="/wiki/Ether" title="Ether">ether</a> group. The exact <a href="/wiki/Reactivity_(chemistry)" title="Reactivity (chemistry)">reactivity</a> of Cadusafos as well as that of organothiophosphate compounds in general is, as of yet, unknown. However, the <a href="/wiki/Cholinesterase" title="Cholinesterase">cholinesterase</a> enzyme inhibition mechanism of action of these compounds works similarly to other organophosphates.<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> Examples of organophosphates include <a href="/wiki/Nerve_gas" class="mw-redirect" title="Nerve gas">nerve gasses</a> such as <a href="/wiki/Sarin" title="Sarin">sarin</a> and <a href="/wiki/VX_(nerve_agent)" title="VX (nerve agent)">VX</a> as well as pesticides like <a href="/wiki/Malathion" title="Malathion">malathion</a>. <sup id="cite_ref-Brett_12-0" class="reference"><a href="#cite_note-Brett-12"><span class="cite-bracket">[</span>12<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=Cadusafos&action=edit&section=3" title="Edit section: Synthesis"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>The synthesis of Cadusafos can be performed via the <a href="/wiki/Substitution_reaction" title="Substitution reaction">substitution reaction</a> of <i>O</i>-ethyl phosphoric dichloride and two equivalents of 2-butanethiol.<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> </p> <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=Cadusafos&action=edit&section=4" title="Edit section: Mechanism of action"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cadusafos is an <a href="/wiki/Enzyme_inhibitor" title="Enzyme inhibitor">inhibitor</a> of the enzyme <a href="/wiki/Acetylcholinesterase" title="Acetylcholinesterase">acetylcholinesterase</a>. This enzyme binds to acetylcholine and cleaves it into <a href="/wiki/Choline" title="Choline">choline</a> and <a href="/wiki/Acetate" title="Acetate">acetate</a>. Acetylcholine is a <a href="/wiki/Neurotransmitter" title="Neurotransmitter">neurotransmitter</a> which is used in neurons to pass on a <a href="/wiki/Neutral_stimulus" title="Neutral stimulus">neural stimulus</a>. Cadusafos inhibits the function of acetylcholinesterase by occupying the <a href="/wiki/Active_site" title="Active site">active site</a> of the enzyme which will no longer be able to function properly, resulting in the <a href="/wiki/Bioaccumulation" title="Bioaccumulation">accumulation</a> of acetylcholine. This might result in excessive nervous stimulation, <a href="/wiki/Respiratory_failure" title="Respiratory failure">respiratory failure</a> and death.<sup id="cite_ref-WHO_14-0" class="reference"><a href="#cite_note-WHO-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Cadusafos is an organothiophosphate, which is a subclass of <a href="/wiki/Organophosphates" class="mw-redirect" title="Organophosphates">organophosphates</a>. Organophosphates can act as an inhibitor for acetylcholinesterase in a way for which the mechanism is known.<sup id="cite_ref-pubchem_1-2" class="reference"><a href="#cite_note-pubchem-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup> The active site of acetylcholinesterase contains an <a href="/wiki/Anionic" class="mw-redirect" title="Anionic">anionic</a> site and an <a href="/w/index.php?title=Esteratic&action=edit&redlink=1" class="new" title="Esteratic (page does not exist)">esteratic</a> site. This esteratic side contains a <a href="/wiki/Serine" title="Serine">serine</a> at the 200th position, which usually binds acetylcholine. Organophosphate inhibitors can <a href="/wiki/Phosphorylate" class="mw-redirect" title="Phosphorylate">phosphorylate</a> this serine and with that inhibit the enzyme.<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="Metabolism_and_biotransformation">Metabolism and biotransformation</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cadusafos&action=edit&section=5" title="Edit section: Metabolism and biotransformation"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>In a study, 14C <a href="/wiki/Radiolabeled" class="mw-redirect" title="Radiolabeled">radiolabeled</a> Cadusafos was administered <a href="/wiki/Oral_administration" title="Oral administration">orally</a> to rats. The excretion of feces, urine and CO<sub>2</sub> was monitored for seven days. This showed that cadusafos is readily <a href="/wiki/Absorption_(pharmacology)" title="Absorption (pharmacology)">absorbed</a> (90-100%)<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> and mainly <a href="/wiki/Clearance_(medicine)" class="mw-redirect" title="Clearance (medicine)">eliminated</a> via urine (around 75%), followed by elimination via expired air (10-15%) and via feces (5-15%). Over 90% of the administered dose was eliminated within 48 hours after administration. Analysis of tissue and blood samples collected after seven days showed a remaining radioactivity between 1-3%.<sup id="cite_ref-Donovan_2-1" class="reference"><a href="#cite_note-Donovan-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> The majority of this radioactivity was found in fat, liver, kidney and lung tissue and no evidence of accumulation was found.<sup id="cite_ref-Donovan_2-2" class="reference"><a href="#cite_note-Donovan-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-EFSA_17-0" class="reference"><a href="#cite_note-EFSA-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> A different study was performed in order to identify the <a href="/wiki/Metabolites" class="mw-redirect" title="Metabolites">metabolites</a> formed in rats after receiving either an oral or <a href="/wiki/Intravenous" class="mw-redirect" title="Intravenous">intravenous</a> dose of Cadusafos. The metabolic products were analyzed using several analysis methods (<a href="/wiki/HPLC" class="mw-redirect" title="HPLC">HPLC</a>, <a href="/wiki/Thin_layer_chromatography" class="mw-redirect" title="Thin layer chromatography">TLC</a>, <a href="/wiki/GC-MS" class="mw-redirect" title="GC-MS">GC-MS</a>, <a href="/wiki/Proton_NMR" class="mw-redirect" title="Proton NMR"><sup>1</sup>H-NMR</a> and <a href="/w/index.php?title=Liquid_scintillation&action=edit&redlink=1" class="new" title="Liquid scintillation (page does not exist)">liquid scintillation</a>). This indicated the presence of the parent compound, Cadusafos, as well as 10 other metabolites. The main pathway of metabolism involves the cleavage of the thio-(sec-butyl) group, forming two primary products: Sec-butyl mercaptan and Oethyl-S-(2-butyl) phosphorothioic acid (OSPA). These intermediate compounds are then degraded further into several metabolites. The major metabolites were <a href="/w/index.php?title=Hydroxysulfones&action=edit&redlink=1" class="new" title="Hydroxysulfones (page does not exist)">hydroxysulfones</a>, followed by <a href="/w/index.php?title=Phosphorothionic_acids&action=edit&redlink=1" class="new" title="Phosphorothionic acids (page does not exist)">phosphorothionic acids</a> and <a href="/wiki/Sulfonic_acids" class="mw-redirect" title="Sulfonic acids">sulfonic acids</a>, which then form <a href="/wiki/Bioconjugation" title="Bioconjugation">conjugates</a>.<sup id="cite_ref-Donovan_2-3" class="reference"><a href="#cite_note-Donovan-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> </p> <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=Cadusafos&action=edit&section=6" title="Edit section: Toxicity"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>A study has been conducted by the Joint <a href="/wiki/FAO" class="mw-redirect" title="FAO">FAO</a>/<a href="/wiki/WHO" class="mw-redirect" title="WHO">WHO</a> Meeting on Pesticide Residues (JMPR), on rats in which the <a href="/wiki/Lethal_dose" title="Lethal dose">lethal dose</a> of Cadusafos was investigated. The researchers found a median lethal dose via the oral pathway of 68.4 mg/kg bodyweight (bw) in male rats and 82.1 mg/kg bw in female rats. The rats died of typical symptoms of acetylcholinesterase inhibition. Via the <a href="/wiki/Dermal" class="mw-redirect" title="Dermal">dermal</a> pathway, lower median lethal doses were found; mg/kg bw in males and 41.8 mg/kg bw in females.<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> Considering the toxicity in humans, there is no data available yet regarding the median lethal dose for a human. The <a href="/wiki/United_States_Environmental_Protection_Agency" title="United States Environmental Protection Agency">United States Environmental Protection Agency</a> (EPA), did publish a report on the safety concerns of Cadusafos used as a pesticide on bananas and concluded that “Potential acute and chronic dietary exposures from eating bananas treated with Cadusafos are below the level of concern for the entire U.S. population, including infants and children.”<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup> </p> <div class="mw-heading mw-heading2"><h2 id="Effects_on_animals">Effects on animals</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cadusafos&action=edit&section=7" title="Edit section: Effects on animals"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cadusafos has been proved to be toxic to fish, <a href="/wiki/Marine_invertebrates" title="Marine invertebrates">aquatic invertebrates</a>, bees, <a href="/wiki/Earthworms" class="mw-redirect" title="Earthworms">earthworms</a> and other <a href="/wiki/Arthropods" class="mw-redirect" title="Arthropods">arthropods</a>. Further research was conducted on terrestrial vertebrates, and it is expected to have toxic effects on mammals.<sup id="cite_ref-database_3-1" class="reference"><a href="#cite_note-database-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Besides its direct toxicity to multiple species, Cadusafos also has a potential to <a href="/wiki/Bioaccumulate" class="mw-redirect" title="Bioaccumulate">bioaccumulate</a> so <a href="/wiki/Secondary_poisoning" title="Secondary poisoning">secondary poisoning</a> for earthworm eating mammals and birds should also be taken into consideration.<sup id="cite_ref-EFSA_17-1" class="reference"><a href="#cite_note-EFSA-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The estimated risk to bees and aquatic organisms is low due to the application of Cadusafos, even though the toxicity to bees is high. The compound is also estimated to be highly toxic to earthworms and birds. A multigeneration study in rats has established a No Adverse Effect Level (<a href="/wiki/NOAEL" class="mw-redirect" title="NOAEL">NOAEL</a>) of 0.03 mg/kg bw per day for the inhibition of cholinesterase activity in <a href="/wiki/Blood_plasma" title="Blood plasma">plasma</a> and <a href="/wiki/Erythrocytes" class="mw-redirect" title="Erythrocytes">erythrocytes</a>.<sup id="cite_ref-Donovan_2-4" class="reference"><a href="#cite_note-Donovan-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> There has been no adequate evidence that Cadusafos could prove a <a href="/wiki/Genotoxic" class="mw-redirect" title="Genotoxic">genotoxic</a> compound. Due to this and additional research on mice and rats which proved Cadusafos as non-<a href="/wiki/Carcinogenic" class="mw-redirect" title="Carcinogenic">carcinogenic</a>, it can be concluded that Cadusafos is non-carcinogenic for humans. </p> <div class="mw-heading mw-heading2"><h2 id="Efficacy">Efficacy</h2><span class="mw-editsection"><span class="mw-editsection-bracket">[</span><a href="/w/index.php?title=Cadusafos&action=edit&section=8" title="Edit section: Efficacy"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <p>Cadusafos proved to be very effective against parasitic <a href="/wiki/Nematode" title="Nematode">nematode</a> populations such as <i><a href="/wiki/Rotylenchulus_reniformis" title="Rotylenchulus reniformis">Rotylenchulus reniformis</a></i> and <i><a href="/wiki/Meloidogyne_incognita" title="Meloidogyne incognita">Meloidogyne incognita</a></i>. It showed to be more effective against <a href="/wiki/Endoparasitic" class="mw-redirect" title="Endoparasitic">endoparasitic</a> nematodes than <a href="/wiki/Ectoparasitic" class="mw-redirect" title="Ectoparasitic">ectoparasitic</a> nematodes <sup id="cite_ref-meher2_4-1" class="reference"><a href="#cite_note-meher2-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> and when compared to other nematicides like <a href="/wiki/Triazophos" class="mw-redirect" title="Triazophos">triazophos</a>, <a href="/wiki/Methyl_bromide" class="mw-redirect" title="Methyl bromide">methyl bromide</a>, <a href="/wiki/Aldicarb" title="Aldicarb">aldicarb</a>, <a href="/wiki/Carbofuran" title="Carbofuran">carbofuran</a> and <a href="/wiki/Phorate" title="Phorate">phorate</a>, Cadusafos proved to be the most efficient. The effectiveness of Cadusafos improves when increasing the <a href="/wiki/Dose_(biochemistry)" title="Dose (biochemistry)">dosage</a> or the exposure time. <sup id="cite_ref-Meher_20-0" class="reference"><a href="#cite_note-Meher-20"><span class="cite-bracket">[</span>20<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-anwar_5-1" class="reference"><a href="#cite_note-anwar-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> <a href="/wiki/Efficacy" title="Efficacy">Efficacy</a> after application for several successive cropping seasons seemed to remain the same for up to four seasons. However, when it is used for more than 4 consecutive seasons, this can cause a linear decrease in the efficacy.<sup id="cite_ref-meher2_4-2" class="reference"><a href="#cite_note-meher2-4"><span class="cite-bracket">[</span>4<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=Cadusafos&action=edit&section=9" title="Edit section: References"><span>edit</span></a><span class="mw-editsection-bracket">]</span></span></div> <style data-mw-deduplicate="TemplateStyles:r1239543626">.mw-parser-output .reflist{margin-bottom:0.5em;list-style-type:decimal}@media screen{.mw-parser-output .reflist{font-size:90%}}.mw-parser-output .reflist .references{font-size:100%;margin-bottom:0;list-style-type:inherit}.mw-parser-output .reflist-columns-2{column-width:30em}.mw-parser-output .reflist-columns-3{column-width:25em}.mw-parser-output .reflist-columns{margin-top:0.3em}.mw-parser-output .reflist-columns ol{margin-top:0}.mw-parser-output .reflist-columns li{page-break-inside:avoid;break-inside:avoid-column}.mw-parser-output .reflist-upper-alpha{list-style-type:upper-alpha}.mw-parser-output .reflist-upper-roman{list-style-type:upper-roman}.mw-parser-output .reflist-lower-alpha{list-style-type:lower-alpha}.mw-parser-output .reflist-lower-greek{list-style-type:lower-greek}.mw-parser-output .reflist-lower-roman{list-style-type:lower-roman}</style><div class="reflist"> <div class="mw-references-wrap mw-references-columns"><ol class="references"> <li id="cite_note-pubchem-1"><span class="mw-cite-backlink">^ <a href="#cite_ref-pubchem_1-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-pubchem_1-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-pubchem_1-2"><sup><i><b>c</b></i></sup></a></span> <span class="reference-text"><style data-mw-deduplicate="TemplateStyles:r1238218222">.mw-parser-output cite.citation{font-style:inherit;word-wrap:break-word}.mw-parser-output .citation q{quotes:"\"""\"""'""'"}.mw-parser-output .citation:target{background-color:rgba(0,127,255,0.133)}.mw-parser-output .id-lock-free.id-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/6/65/Lock-green.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-limited.id-lock-limited a,.mw-parser-output .id-lock-registration.id-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/d/d6/Lock-gray-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .id-lock-subscription.id-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/a/aa/Lock-red-alt-2.svg")right 0.1em center/9px no-repeat}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/4/4c/Wikisource-logo.svg")right 0.1em center/12px no-repeat}body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-free a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-limited a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-registration a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .id-lock-subscription a,body:not(.skin-timeless):not(.skin-minerva) .mw-parser-output .cs1-ws-icon a{background-size:contain;padding:0 1em 0 0}.mw-parser-output .cs1-code{color:inherit;background:inherit;border:none;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;color:var(--color-error,#d33)}.mw-parser-output .cs1-visible-error{color:var(--color-error,#d33)}.mw-parser-output .cs1-maint{display:none;color:#085;margin-left:0.3em}.mw-parser-output .cs1-kern-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right{padding-right:0.2em}.mw-parser-output .citation .mw-selflink{font-weight:inherit}@media screen{.mw-parser-output .cs1-format{font-size:95%}html.skin-theme-clientpref-night .mw-parser-output .cs1-maint{color:#18911f}}@media screen and (prefers-color-scheme:dark){html.skin-theme-clientpref-os .mw-parser-output .cs1-maint{color:#18911f}}</style><cite class="citation web cs1"><a rel="nofollow" class="external text" href="https://pubchem.ncbi.nlm.nih.gov/compound/Cadusafos">"Cadusafos"</a>. <i>pubchem.ncbi.nlm.nih.gov</i><span class="reference-accessdate">. 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"Persistence and nematicidal efficacy of carbosulfan, cadusafos, phorate, and triazophos in soil and uptake by chickpea and tomato crops under tropical conditions". <i>Journal of Agricultural and Food Chemistry</i>. <b>58</b> (3): <span class="nowrap">1815–</span>1822. <a href="/wiki/Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1021%2Fjf903609d">10.1021/jf903609d</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/20085277">20085277</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+Agricultural+and+Food+Chemistry&rft.atitle=Persistence+and+nematicidal+efficacy+of+carbosulfan%2C+cadusafos%2C+phorate%2C+and+triazophos+in+soil+and+uptake+by+chickpea+and+tomato+crops+under+tropical+conditions&rft.volume=58&rft.issue=3&rft.pages=%3Cspan+class%3D%22nowrap%22%3E1815-%3C%2Fspan%3E1822&rft.date=2010-02&rft_id=info%3Adoi%2F10.1021%2Fjf903609d&rft_id=info%3Apmid%2F20085277&rft.aulast=Meher&rft.aufirst=HC&rft.au=Gajbhiye%2C+VT&rft.au=Singh%2C+G&rft.au=Kamra%2C+A&rft.au=Chawla%2C+G&rfr_id=info%3Asid%2Fen.wikipedia.org%3ACadusafos" class="Z3988"></span></span> </li> </ol></div></div>    </div><noscript><img src="https://auth.wikimedia.org/loginwiki/wiki/Special:CentralAutoLogin/start?useformat=desktop&type=1x1&usesul3=1" alt="" width="1" height="1" style="border: none; position: absolute;"></noscript> <div class="printfooter" data-nosnippet="">Retrieved from "<a dir="ltr" href="https://en.wikipedia.org/w/index.php?title=Cadusafos&oldid=1245905053">https://en.wikipedia.org/w/index.php?title=Cadusafos&oldid=1245905053</a>"</div></div> <div id="catlinks" class="catlinks" data-mw="interface"><div id="mw-normal-catlinks" class="mw-normal-catlinks"><a href="/wiki/Help:Category" title="Help:Category">Categories</a>: <ul><li><a href="/wiki/Category:Nematicides" title="Category:Nematicides">Nematicides</a></li><li><a href="/wiki/Category:Ethyl_esters" title="Category:Ethyl esters">Ethyl esters</a></li><li><a href="/wiki/Category:Phosphorodithioates" title="Category:Phosphorodithioates">Phosphorodithioates</a></li><li><a href="/wiki/Category:Insecticides" title="Category:Insecticides">Insecticides</a></li><li><a href="/wiki/Category:Thioesters" title="Category:Thioesters">Thioesters</a></li><li><a href="/wiki/Category:Sec-Butyl_compounds" title="Category:Sec-Butyl compounds">Sec-Butyl compounds</a></li></ul></div><div id="mw-hidden-catlinks" class="mw-hidden-catlinks mw-hidden-cats-hidden">Hidden categories: <ul><li><a href="/wiki/Category:Articles_with_short_description" title="Category:Articles with short description">Articles with short description</a></li><li><a href="/wiki/Category:Short_description_is_different_from_Wikidata" title="Category:Short description is different from Wikidata">Short description is different from Wikidata</a></li><li><a href="/wiki/Category:Drugs_with_non-standard_legal_status" title="Category:Drugs with non-standard legal status">Drugs with non-standard legal status</a></li><li><a href="/wiki/Category:ECHA_InfoCard_ID_from_Wikidata" title="Category:ECHA InfoCard ID from Wikidata">ECHA InfoCard ID from Wikidata</a></li><li><a href="/wiki/Category:Infobox_drug_articles_with_non-default_infobox_title" title="Category:Infobox drug articles with non-default infobox title">Infobox drug articles with non-default infobox title</a></li><li><a href="/wiki/Category:Chemical_pages_without_DrugBank_identifier" title="Category:Chemical pages without DrugBank identifier">Chemical pages without DrugBank identifier</a></li><li><a href="/wiki/Category:Drugs_missing_an_ATC_code" title="Category:Drugs missing an ATC code">Drugs missing an ATC code</a></li><li><a href="/wiki/Category:Articles_containing_unverified_chemical_infoboxes" title="Category:Articles containing unverified chemical infoboxes">Articles containing unverified chemical infoboxes</a></li></ul></div></div> </div> </main> </div> <div class="mw-footer-container"> <footer id="footer" class="mw-footer" > <ul id="footer-info"> <li id="footer-info-lastmod"> This page was last edited on 15 September 2024, at 20:20<span class="anonymous-show"> (UTC)</span>.</li> <li id="footer-info-copyright">Text is available under the <a href="/wiki/Wikipedia:Text_of_the_Creative_Commons_Attribution-ShareAlike_4.0_International_License" title="Wikipedia:Text of the Creative Commons Attribution-ShareAlike 4.0 International License">Creative Commons Attribution-ShareAlike 4.0 License</a>; additional terms may apply. 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